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DOI: 10.1039/C8PY00863A
Polymer Chemistry
REVIEW
Preparation and Application of Flavor and Fragrance Capsules

Published on 28 August 2018. Downloaded by University of Reading on 8/30/2018 9:28:00 AM.
Polymer Chemistry Accepted Manuscript

*
Lei He, Jing Hu and Weijun Deng
Received 00th January 20xx,
Accepted 00th January 20xx Flavor and fragrance as a special active material are applied widely in daily life, which can bring pleasant olfactory and
gustatory sensation. However, their many ingredients are chemically unstable and susceptible to deterioration and lost,
DOI: 10.1039/x0xx00000x
when flavor and fragrance are exposed to oxygen, light and heat. Nano and micrometer size capsules with a hollow core
www.rsc.org/ domain and a shell can effectively protect the stability of flavor and fragrance and controll their release. The structures
and properties of flavor and fragrance capsules can be interestingly tailored by choosing a variety of shell materials. In this
review, we give a brief overview with regard to the different preparation methods of flavor and fragrance capsules based
on the types of the wall materials including polymeric, inorganic and polymeric-inorganic materials. Besides, the
application of flavor and fragrance capsules in food, tobacco, care product, textile, leather and paper has been shortly
summarized. Moreover, the development trend of flavor and fragrance capsules was prospected.
to three wall materials: polymeric, inorganic, and polymeric-

1. Introduction inorganic (Fig. 1). Polymeric capsules from nano-scale to micron-
scale have become increasingly attractive and experienced a
Flavor and fragrance as an important kind of addition have been
blooming development over the past two decades. Inorganic and
applied widely in food, medicine, cosmetic, leather, textile and paper,
polymeric-inorganic shell materials were just paid more attention in
which can beautify people’s life.1, 2 However, their sensitive or
the last decade, due to their controllable morphology and special
volatile aromatic ingredients are easily to be deteriorated and lost
3, 4 aroma release way. Then we highlight the important applications of
during their storage and manufacture process. The encapsulation
flavor and fragrance capsules. Smart flavour and fragrance capsules
technique can effectively prevent from losing the volatile aromatic
span over a wide panel of applications ranging from food, tobacco,
compounds and extend their use efficacy.5-7 This is attributed to that
care product, intelligent fabrics, leather and paper. The intent is to
capsules normally have the multifunctional features of small size,
give the readers a further discussion of the synthesis and applications
high specific surface area, large inner volume, selectivity, stable and
of flavor and fragrance capsules.
ductile shells. Now, flavor and fragrance capsules can be divided
into nanocapsules (size<1 µm), and microcapsules with the size in
the range of 1~1000 µm.
Recent review articles have been well written from different
perspectives: Some focused on the synthetic methods of polymeric
capsules.8-10 Some mainly discussed the preparation and application
of essential oil microcapsules.11-14 Different flavor and fragrance
capsules may share common preparation principles or require
different fabrication strategies and may have different properties.15
What’s more, the wall materials of capsules would affect the
structures and properties of flavor and fragrance capsules
absolutely.16 Generally, the wall materials can be selected according
to the following principles. (I) Flavor and fragrance can be
completely encapsulated to avoid the environmental influence. (II)
Wall materials are inert without reacting with flavor and fragrance.
(III) Wall materials need a low viscosity at their high concentration.
(IV) Flavor and fragrance capsules can be easily separated from
solvent. (V) Wall materials are economic, safe and healthy. In order
to avoid overlap with the previous reviews, we will first discuss the
Fig. 1 A brief overview about flavor and fragrance capsules with polymeric,
main fabrication methods of flavor and fragrance capsules according
inorganic and polymeric-inorganic materials as the shell discussed in this
review.
This journal is © The Royal Society of Chemistry 20xx Polym. Chem., 2018, 00, 1-3 | 1
Polymer Chemistry Page 2 of 20
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DOI: 10.1039/C8PY00863A
REVIEW Polymer Chemistry
2. Polymeric capsules mass transfer will be affected by the time and temperature and the
highest aroma loading capacity reached 49 %. Furthermore, flavor
Polymeric capsules have aroused a vast and increasing interest in
and fragrance capsules with good morphology and improved aroma
flavor and fragrance due to their light weight, excellent mechanical
retention were prepared via SFD, which combined the advantages of
properties, extensive source and easy-process.17, 18 Polymeric
both of spray-drying and freeze-drying,53,54 Ishwarya et al. compared
capsules loaded with flavor and fragrance can be divided into two
the differences among the coffee microcapsules with whey protein
categories of natural and synthetic ones depending on their sources.
isolate as the wall obtained by the above three methods.55 The
retention ratio of the volatile compounds in coffee microcapsules
2.1 Natural polymers prepared via SFD was the highest (93 %). However, the employment
of liquid nitrogen or other cold sources during SFD process caused

Natural polysaccharides and proteins are the common wall materials,
the produced cost increasing and industrialization difficult.
which construct a variety of flavor and fragrance capsules, due to
Moreover, electrospray exhibited the unique advantage in the road of
their biocompatibility, non-toxic and extensive-source. Chitosan
industrialization, which produced a uniform spray droplet with the
(CS),19,20 gum arabic (GA),21 alginate,22 β-glucan,23 starch and its
controlled size from nanometer to micrometer based on the high-
derivative,24,25 plant protein and gelatin 26-29 have been used to
potential electric field.56 Ghayempour et al. first prepared essential
encapsulate flavor and fragrance via physical and chemical process.
oil capsules with controllable particle size (80 nm to 900 µm) by
Physical method as the most commonly used technology for
electrospray using sodium alginate as the wall material.57, 58 As
flavor and fragrance capsules with natural polymeric walls, has
shown in Fig. 2, the emulsion (o/w) of essential oil and alginate
showed the great potential in industrial productions during the past
solution flow out from the coaxial nozzles, and the inner one of the
decades, which includes spray-drying,30-36 freeze-drying,37,38 spray–
emulsion was dripped into the outer one of alginate solution. The
freeze drying (SFD),39 electrospraying,40 co-extrusion,41-43 and so
liquids disintegrated into droplets by electrical forces, which were
on.44,45 Spray-drying is the pioneer for flavor and fragrance
dripped into CaCl2 solution to form hydrogel capsules by the
capsules.46-48 In a typical procedure, spray-drying involves the
reaction bewteeen alginate and polyvalent cations under
atomization of emulsions into a drying chamber at a relatively high
continuously stirring. The encapsulation efficiency of the essential
temperature, which leads to very fast water evaporation.49 For
oil nanocapsules was as high as 96.4 %.
example, Li et al. prepared orange oil microcapsules with the size of
Another novel wall material, alyssum homolocarpum seed gum
21 µm and the encapsulation efficiency of 90 % by spray-drying
(AHSG) is used to prepare limonene nanocapsules through
using an aqueous acetic acid solution of CS as wall material.50 The
electrospraying process.59 The anionic nature of AHSG may
storage stability of orange oil by encapsulated with chitosan was
facilitate the electrospraying process due to the presence of high
improved compared to free orange oil. Free orange oil was almost
electric charges on the droplets, which compete with the surface
completely volatilized in 8 h at 45 °C, but orange oil encapsulated in
tension of solution, causing the jet to break up into droplets. The
chitosan under the same conditions volatilized over a period of
morphology of the resulting nanostructures was mainly affected by
months. However, the acetic acid solution of CS brought a sour odor
the physical properties of electrospraying solution, particularly the
for the final capsules. To avoid the above problem, the modified CS
dosage of core material, rheological behavior, surface tension and
and CS with the low molecular weights can be employed as the
electrical conductivity. The morphology of nanocapsules changed to
walls.51 Interestingly, Sultana et al. used dried Saccharomyces
nanofibers by increasing the limonene content to 30 %. From the
cerevisiae cells as the wall material to prepare d-limonene and ethyl
data of thermogravimetric analysis, limonene was began to release at
hexanoate microcapsules via spray-drying.52 Unlike the former
46 °C, while the released temperature of limonene in nanocapsules
emulsification process, the fragrance was transferred through the
improved to 59 °C, and its heat stability was significantly improved.
lipid bilayer membrane into the interior of the cell. The properties of
Fig. 2 (a) Schematic description of the encapsulation system using a coaxial jets electrospray (b) SEM micrographs of essential oil-nanocapsules. Reprinted with permission
from ref. 57. Copyright 2013 Elsevier Ltd.
2 | Polym. Chem., 2018, 00, 1-3 This journal is © The Royal Society of Chemistry 20xx
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Fig. 3 (a). Schematic illustrations of the formation process of tuberose fragrance nanocapsules with CS–TPP as the wall; (b). TEM images of tuberose fragrance
nanocapsule. Reprinted with permission from ref. 69. Copyright 2013 John Wiley & Sons, Ltd.
Although physical methods are various and easy, many heat- completely decomposed during 70-185ºC. After the encapsulation of
sensitive aroma components are easy to be lost or deteriorated at the fragrance, their degradation temperatures increased to 90-230°C.
high temperatures during the process. In order to maintain the Then they also successfully prepared osmanthus and rose CS
volatile aroma compounds completely encapsulated into the nanocapsules.70, 71 Recently, Hu et al. used the similar method to
capsules, the gentle and simple preparation methods of flavor and fabricate three cinnamon essential oil nanocapsules with different
fragrance capsules are urgently demanded. sizes (112 nm, 215 nm and 527 nm).72 The loading capacities of
Chemical methods including complex coacervation60,61 and cinnamon essential oil (12.43 % to 20.65 %) were increased with the
molecular inclusion complexation 62,63 at the mild conditions have size enhancement of these nanocapsules. When the wall materials
attracted more attention. The complex coacervation as a typical changed to gelatin-GA, the heat resistant nanocapsule loading
representative is a phase separation process based on a coacervate jasmine essential oil with the size less than 100 nm were obtained.73
between the oppositely charged materials.8 The types of the These nanocapsules could endure the water bath of 80 ºC for 7 h,
oppositely charged materials would influence the size of flavor and due to cross-linking of transglutaminase.
fragrance capsules obviously.64-67 For instance, Liu and coworker Molecular inclusion complexation as the second chemical
prepared patchouli oil microcapsules using chitosan–gelatin as wall fabrication technique was suitable for cyclodextrin (CD) with the
material by complex coacervation.68 The mean size, encapsulation special structure.74 CDs can be used as "host" to load various
efficiency and loading capacity of the microcapsules were 12.81µm, "hydrophobic guest" compounds due to their hydrophobic glycoside
50.69% and 30.31%, respectively. Interestingly, Xiao et al. prepared cavity and hydroxyl outer wall.75 Fenyvesi et al. reported that the
tuberose fragrance nanocapsules with the size of 174 nm and loading inclusion complexation of α-, β-, γ-CD and their mixtures enhanced
capacity of 29.5 % via the electrostatic interactions of sodium the thermal and storage stability of aroma components obviously.76
tripolyphosphate (TPP) and CS.69 As shown in Fig. 3, tuberose The CD and flavor molecules bound to each other depending on
fragrance was emulsified with the emulsifiers by the ultrasonic their hydrophobic interactions. Meanwhile the suitable cavity size
treatment. Then fragrance has been encapsulated into CS–TPP can promote such physicochemical effects. β-CD showed excellent
nanocapsules via the ionic gelification between the positively complexation efficiency (CE) with linalool (CE=30), while for citral
charged of CS and the negatively charged of TPP. The thermal it is very low (CE = 0.03). Ceborska et al. proved the formation of
stability of fragrance was significantly improved. Tuberose fragrance 1:1 host–guest complexes for β- and γ-CD with the two enantiomers
of highly volatile isopulegol in solution, while for the smallest α-CD,
no complex formation was observed.77 In solid state both
enantiomers of isopulegol formed 2:2 inclusion complexes with β-
CD, where the CD molecules were arranged in molecular capsules
forming molecular container able to accommodate two guest
molecules (Fig. 4). In addition, the monodispersity and solubility of
CD in solution would influence the complexation efficiency of
flavor and fragrance capsules.78-81
Besides, amylose and long branched chains of amylopectin also
have the unique feature to form helical inclusion complexes with
flavor compounds.82-85 Yeo and coworker reported the effect of the
composition, hydrophobicity and concentration of flavor on the
Fig. 4 Inclusion complex of -cyclodextrin with (+)-isopulegol (a) and (-)- retention of aroma compounds from the inclusion complexes with
isopulegol (b). Reprinted with permission from ref. 77. Copyright 2013 Elsevier the high amylose maize starch.86 The addition of menthone can
Ltd.
This journal is © The Royal Society of Chemistry 2018 Polym. Chem., 2018, 00, 1-3 | 3
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improve the synergetic interaction between limonene and starch. while their oil load ranged from 3.64 to 7.46%. Differential scanning
Then, Qiu et al. used the short linear glucan (short amylose) calorimetry analysis indicated that the melting temperature and heat
obtained by debranching native waxy corn starch with pullulanase to storage capacity of the nanoparticles were higher than that of the
fabricate menthone-loaded starch nanoparticles with the sizes pure PEG 6000. This is a desirable property as it makes the
ranging from 93 to 113nm.87 The radical scavenging activity of nanoparticle heat stable during transportation when shearing tends to
menthone reached a minimum of 28% after heating 6h at 80 ºC. increase the temperature. Getachew et al. modified the melt-
However, the activity of SNPs-M was still more than 56%. These dispersion method by using particles from gas-saturated solutions
results indicated that encapsulation of menthone in the nanoparticles (PGSS) process.97 The average size of the obtained coffee oil
greatly enhanced the antioxidative stability against temperature. microcapsules kept 78 µm and the highest encapsulation efficiency
From the above one can see that the size and loading capacity of of coffee oil was 79.78 %.

flavor and fragrance capsules with the natural polymers can be well Although physical methods have showed many advantages for the
controlled to a certain extent by using various physical and chemical preparation of the synthetic polymeric capsules, some problems such
methods. The thermal resistance of flavor and fragrance has been as the encapsulation efficacy and loading capacity of flavor and
improved some with the encapsulation of natural polymers. fragrance, capsule morphology and the stiff of capsule shell hindered
Meanwhile, natural polymeric capsules have been studied the improvement of the properties of flavor and fragrance capsules.
extensively, which can become the earliest class production of flavor Up to now, chemical method has been attracted more attention due to
and fragrance capsules. However, the aroma can be released from its universality and stability. Many elegant methods have been
these capsules by destroying the natural polymer walls with the reported towards the fabrication of flavor and fragrance capsules
mechanical treatments or through the holes on their surface. This with synthetic polymers as the wall, typically including emulsion
would hamper the controlled-release of flavor and fragrance under polymerization and interfacial reaction.98
the special environments. Emulsion polymerization is one of the most representative
methods used to create flavor and fragrance capsules and based on
2.2 Synthetic polymers the phase separation.99 The principle of this process is that the
The most attractive characteristics of synthetic polymers show the hydrophobic flavor and fragrance were first solubilized into the
excellent chemical resistance, heat resistance and weather ability.88-90 micelles by means of emulsifiers and mechanical treatment.100-102
Similar to natural polymers, the fabrication of synthetic polymeric Then the monomers solubilized in the micelle initiated to be
capsules can also be divided into physical and chemical methods. polymerized, so that the phase separation of the newly produced
Physical technique is the early developing approach for the polymers occurred from the oily mixture to obtain flavor and
preparation of flavor and fragrance capsules with synthetic polymers fragrance capsules.103-105 Theisinger et al. reported the encapsulation
as the wall materials, due to their simplicity, convenience, and low- of the hydrophobic fragrance 1,2-dimethyl-1-phenyl butyramide in
cost.91 Two methods in particular are used to fabricate flavor and PMMA, polystyrene (PS), and acrylic copolymer nanoparticles with
fragrance capsules. One is solvent evaporation method, which a miniemulsion polymerization process.106 Different types of
induces a polymer to precipitate as a film (the shell) at the oil/water homopolymers and copolymers were used as the polymeric shell
interface. In a typical process, the flavor and fragrance and polymer material with different glass-transition temperatures (Tgs) to obtain
are initially dissolved into a highly volatile solvent and emulsified fragrance-delivery systems for long delivery time of the fragrance at
into a stabilizer solution. Subsequently the volatile solvent is
extracted from the emulsion droplets.92 Polymer is precipitated to
encapsulate the core materials. For instance, Teeka et al. prepared
poly(methyl methacrylate) (PMMA) microcapsules loaded with
jasmine oil via solvent evaporation method.93 The morphology and
the encapsulation efficiency of jasmine oil of the microcapsules were
related to the weight ratio of PMMA and jasmine oil. They further
established a calculation model to predict the final morphology of
the capsules, which based on the spreading coefficients calculated
from the interfacial tensions of the three phases of water, oil and
polymers.94
Another melt-dispersion method is suitable for a special
polyethylene glycol (PEG) to prepare flavor and fragrance capsules.
PEG has a helical molecular structure that possesses hydrophilicity,
solubility in water and organic solvents and biocompatibility. PEG
was first melt at the high temperature and blended with flavor and
fragrance together. After that, PEG was solidified to encapsulate
flavor and fragrance by cooling the above mixtures.95 Kumar et al.
used PEG 6000 to prepare nanoparticles loading Mentha × piperita
essential oil with the average sizes between 226 and 331nm.96 The
encapsulation efficiency of these nanoparticles was 78.2–83.4%,
Fig. 5 (a) Schematic drawing of the release mechanism; (b) TEM images of
closed capsules and opened capsules(c). Reprinted with permission from ref.
107. Copyright 2014 American Chemical Society.
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different temperatures. It was shown that the amount of encapsulated suffers from difficulty in controlling particle size dispersity and the
volatile compound could be varied over a wide range and that the increase of the particle size caused by a large amount of emulsifiers.
amount of the fragrance directly influenced the molecular weight, The interfacial reaction can be expectedly favorable to obtain the
the kinetics of polymerization, and the Tg of the polymers. The controllable capsule morphology.108, 109 This is attributed to that the
particles consisted of a matrix composed of the fragrance in the typical polymers such as polyamide,110 polyurea,111 polyurethane,112
polymer up to about 25 % of the fragrance. Interestingly, Hofmeister urea/melamine–formaldehyde113-118 and polyester119 can produce on
et al. reported that α-pinene nanocapsules with high diffusion barrier the interface to encapsulate flavor and fragrance directly.120 Up to
and pH-responsive release property was synthesized based on a now, several types of reactions including anionic polymerization,121
miniemulsion-analogous, polymerization-induced phase separation polycondensation,122 polyaddition 123 and free radical polymerization
process.107 The copolymer composition was systematically varied, 124
have been used to prepare flavor and fragrance capsules at the

and increasing contents of methacrylic acid (MAA) as functional O/W interface in the emulsion system.
monomer in combination with high glass transition temperatures The anionic polymerization was mainly used to fabricate poly(n-
enabled unusually high encapsulation efficiencies of ≥90 % for butyl cyanoacrylate) (PBCA) capsules. For instance, Hu et al.
capsules with the average diameters of <200 nm. The carboxylic prepared rose nanocapsules with the size of 67.3 nm and the
acid groups of MAA made the polymer shell have pH encapsulation efficiency of 65.83 % via anionic polymerization with
responsiveness. Upon pH increase the carboxylic acid groups in PBCA as the wall in miniemulsion.121 Rose fragrance as a water-
glassy polymer shell became deprotonated and transferred into a insoluble monomer was emulsified by the surfactants under strong
weak polyelectrolyte structure with partial hydrogel-character, which mechanical stirring action in the aqueous phase during this process.
triggered the release of aroma (Fig. 5). The higher the MAA content, When BCA was added into the system, BCA was diffused into the
the faster was the release of aroma upon deprotonation. When the micelles through the water phase. Then, BCA will be polymerized at
nanocapsules were heated at 60 °C for 30 min, the total aroma the O/W interface to encapsulate rose fragrance initiated by OH–.
release changed from 2% to 90%, with MAA content increased from Then they similarly synthesized tuberose nanocapsules with the
2.5 to 10%. average size of 202.4 nm and the loading capacity of 50.9 %.125
The emulsion polymerization based on phase separation offers However, at the end of the interfacial anionic polymerization, the
numerous advantages such as the highly spherical particle adjusted pH of the system would destroy the flavor and fragrance.126
morphologies and mild reaction conditions. However, this method
Fig. 6 Formation of composite core/shell capsules polyurea/coacervate multilayer membranes. Reprinted with permission from ref. 132. Copyright 2017 Wiley & Sons,
Ltd.
Fig. 7 Encapsulation by Interfacial Polymerization and Release by pH Triggers. Reprinted with permission from ref. 134. Copyright 2017 American Chemical Society.
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Fig. 8 (a) Schematic drawing of the fabrication, cargo loading, and photode-gradation of the P(NIPAM-ONB-MAA) polymer nanocapsules; (b) TEM images of the
nanocapsules and (c) TEM images of the nanocapsules after photodegradation. Reproduced from Ref. 135 with permission from the Royal Society of Chemistry.
Interfacial polycondensation or polyaddition can be conveniently shells,132 combining a strong chemical barrier formed by synthetic
realized by using one hydrophobic and one hydrophilic precursor, polyurea with the outstanding adhesive properties of protein based
which dissolve in separate phases.127-129 Polyurethane is an complex coacervates (Fig. 6). The coacervates first formed via phase
appropriate candidate for microcapsule shell due to its good adhesive separation by mixing solutions of a protein and a weak polyanion,
properties and compatibility. The present work aims at the followed by interfacial deposition of this separated coacervate phase
development of polyurethane capsules based on the materials taken on the oil drops, thereby creating a coacervate shell. A polyurea
from sustainable renewable sources. Azizi et al. fabricated neroline- membrane was then synthesized in situ from the interface between
loaded microcapsules with 27 µm diameter by using the bio-based the coacervate and the oil core, resulting in a composite
isosorbide as a diol in place of the conventional diols.130 In order to polyurea/coacervate shell.
enhance both the microcapsule–substrate interactions and the Lately, the environmental responsive capsules loading flavor and
mechanical properties of the capsules to induce a burst-type release, fragrance have been attracted more attention.133 Wang et al.
the next generation of core/shell microcapsules with low- developed a polyamide microcapsule using interfacial
permeability membranes and controlled morphology for the delivery polymerization of a diester diacid chloride with diethylenetriamine
and controlled release of fragrance molecules is gradually rising.131 (DETA) and a triazine trisamine to impart high loading capacity and
Dardelle et al. synthesized limonene capsules with composite dual acid/base-responsive properties.134 As shown in Fig. 7, a
Fig. 9 (a) Schematic representation of the preparation of fragrance/silica nanocapsules; (b) TEM images of silica nanocapsules containing γ-unsecalactone. Reprinted with
permission from ref. 147. Copyright 2015 Springer-Verlag.
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saturated solution of pyromellitic diester diacid chloride and catalytic and optoelectronic properties.137-140 The inorganic capsules
coumarin in toluene was emulsified with an aqueous poly(vinyl encapsulated with active substances have significant chemical and
alcohol) solution with magnetic stirring to produce a suspension of physical stability, thereby expanding the application of chemically
O/W emulsion droplets, whose shapes and sizes determine the final unstable flavor and fragrance.141 Until now, SiO2 capsules have been
capsule dimensions. Dropwise addition of an aqueous solution of considered as the common, economical, and environmentally
triazine and DETA initiated a polycondensation reaction at the water- friendly materials. Sol-gel method and Pickering emulsion
oil interface to form a cross-linked polyamide shell. The polyamide technology are widely used to fabricate SiO2 capsules with
microcapsules with the diameters between 200 and 350 μm has the controllable morphology and monodispersity.142 In a typical sol-gel
high core content of 95%. After 18 months of storage at room process, both of PS colloid particles and emulsion as templates were
temperature the weight percent of the liquid core remained coated by controlled surface precipitation of SiO2 nanoparticles.

unchangeable, suggesting high storage stability in the dry state. When PS template particles were utilized, they should be removed
More interestingly, this microcapsules also kept stable in nonpolar by selective dissolution in an appropriate solvent or by calcination at
environment (toluene) but undergo steady, controlled release at pH elevated temperature in air, leaving behind SiO2 capsules.143 Finally,
7.4 and accelerated release at pH 5 and pH 10. SiO2 capsules were directly to load flavor and fragrance by physical
The interfacial free-radical polymerization is simple by initiating adsorption and kept the excellent morphology.144 Xue et al.
one monomer polymerized. Zhao et al. successfully prepared fabricated hollow mesoporous silica nanospheres with the size of
peppermint oil microcapsules using poly(1, 4-butanediol 233 nm using PS template by sol-gel way and loaded lemon essential
dimethacrylate)(BDDMA) as wall material.135 With the addition of oil with the loading capacity of 85.8 %.145 The amount of the lemon
ammonium persulfate, the free radicals triggered the carbon–carbon essential oil from dried nanocapsules released was only 7.9% after
double bond of BDDMA monomer to polymerize at the interface of placed 6 days at temperature of 20 °C. While, essential oil can be
the droplets. Finally, the fragrance microcapsules with spherical released at high temperature of 50 °C for more than 30 hours.
shape, good thermal stability below 100 ºC and high encapsulation Furthermore, when the flavor and fragrance emulsions were used as
efficiency of 91% were obtained. The novel photodegradable soft templates, these aroma volatile compounds can be encapsulated
polymer nanocapsules were further fabricated via free-radical into SiO2 capsules via one-step. This greatly simplified the
polymerization based on dimethyldiethoxysilane emulsion preparation process of SiO2 capsules templating against colloid PS
template.136 The light responsive cross-linker 5-(methacryloyloxy)- particles. Sousa et al. synthesized farnesol amorphous SiO2 capsules
2-nitrobenzyl methacrylate (ONB) was first synthesized from 5- (0.44–0.94 µm) using O/W/O multiple emulsions as soft template by
hydroxy-2-nitrobenzyl alcohol and methacryloyl chloride by sol-gel method.146 Tetraethoxysilane (TEOS) was initially
esterification. The dimethyldiethoxysilane (DMDES) emulsion solubilized in the oil phase and then migrated to the oil-water
droplets were mixed with the hydrophobic cross-linker ONB to be interface, where their hydrolysis and condensation occurred. After
employed as sacrificial templates. The carbon–carbon double bonds
were modified onto the surfaces of the emulsion templates from 3-
(trimethoxysilyl) propyl methacrylate (MPS) via the silane chemistry
reaction. In the presence of the initiator potassium persulfate, N-
isopropylacrylamide (NIPAM) and MAA monomers in water were
polymerized at 70 °C onto the DMDES emulsion template surface,
forming polymeric shells. Meanwhile, the hydrophobic cross-linker
ONB was applied for the crosslinking of the polymeric chains at the
interface of the oil-in-water emulsion droplets during the free radical
polymerization. Hollow P(NIPAM-ONB-MAA) polymer
nanocapsules with a size around 550 nm were obtained after the
removal of the DMDES emulsion templates and unreacted cross-
linkers by ethanol washing. (Fig. 8). Finally, the hydrophobic
coumarin 102 can be encapsulated into the hollow capsules with the
loading capacity of 14.5 %.
For synthetic polymeric capsules loaded with flavor and
fragrance, chemical reaction is the most important method to
fabricate capsules. Compare to the natural polymer wall materials,
the synthetic polymeric walls can conveniently achieve complex
structure and polyfunctionality of flavor and fragrance capsules.
Besides, the thermal resistance of flavor and fragrance in synthetic
polymeric capsules enhanced greater than that in natural polymeric Fig. 10 (a) Schematic illustration of the formation process of silica capsules; (b)
capsules. TEM of the capsules; (c) FE-SEM image of an “opened” colloidosome; (d) FE-
SEM images of of the capsule. (e)Cinnamaldehyde within the oil reacts with the
amines on the nanoparticles at the oil/water interface to create capsules.
3. Inorganic capsules (f)Confocal micrographs. The nanoparticles' cores are labeled with fluorescein
isothiocyanate (green fluorescence) and the oil phases are loaded with Nile red
Inorganic materials have their special mechanical, thermal, optical, (red fluorescence). Reprinted with permission from ref. 148. Copyright 2014
American Chemical Society; Reprinted with permission from ref. 149.
Copyright 2015 American Chemical Society.
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that, the water-soluble silica oligomers remained in the aqueous SiO2 capsules have exhibited a unique advantage for flavor and
phase continued to be reacted for the growth of an amorphous SiO2 fragrance encapsulation due to its chemical inertness, mechanical
shells. Meanwhile, the size of SiO2 capsule can be adjusted to nano- stability, biocompatibility, easy functionalization, and optical
scale by choosing a miniemulsion template.147 As shown in Fig. 9, transparency.150, 151 Another inorganic class, calcium carbonate
the droplets containing fragrance, TEOS and a small amount of (CaCO3) has become a research hot spot, which is attributed to that
hexadecane were dispersed in the continuous phase under the the release of aroma compounds from capsules can be triggered by
protection of a cationic surfactant, cetyltrimethylammonium bromide pH or mechanical force. Wang et al. prepared CaCO3-limonene
(CTAB). Only the TEOS molecules on the surface of the droplets capsules with the micro-size (15 to 20 µm) and high encapsulation
could undergo hydrolysis and subsequent condensation to form efficiency (90 %) via Pickering emulsion templates.152 Micron size
inorganic cross-linked silica species. The negatively charged silica pristine CaCO3 particles were used to stabilize the hydrophobic

species precipitated onto the surface of droplets with the electrostatic liquid in O/W emulsion. They also acted as nucleate sites for the
interaction between SiO2 and CTAB. The size of the obtained SiO2 crystallization of CaCO3 crystals that formed a dense shell around
nanocapsules loading a series of fragrances varied in the range of the droplet and fully encapsulate the droplet. The encapsulated
140–220 nm and the encapsulation efficiency of fragrance is up to limonene demonstrated a prolonged release time for more than
48.1 %. 40 min in neutralwater at 85 ºC and a triggered release at pH 2.
Another method, termed Pickering emulsion technology has Compared to polymeric capsules, inorganic capsules showed the
become an attractive topic of the investigation since it can improve excellent mechanical property, morphology and monodispersity.
the encapsulation efficiency of flavor and fragrance. The principle of However, to date, the inorganic capsules have only focused on some
this process is that the inorganic nanoparticles can be adsorbed at the special compounds such as SiO2 and CaCO3. Few properties
oil/water interface to stabilize the oil droplets. Zhao et al. first including thermal resistance, sustained-release properties of the
prepared oil /water emulsion with the hexadecyltrimethoxysilane inorganic capsules loaded with flavor and fragrance have been
modified SiO2 nanoparticles of 53.5 ± 3.9 nm as the stabilizers (Fig. reported. The release of aroma compounds from inorganic capsules
10a).148 Then, these SiO2 nanoparticles were linked by a silica was mainly achieved depending on the size of the pores of these
precursor polymer-hyperbranched polyethoxysiloxane at the capsules. Therefore, the shell compactness and their surfacial pore
oil/water interface to enclose hexyl acetate with almost 100 % sizes of the inorganic capsules would play an important role.
efficiency. More interestingly, the aroma compounds can be
ingeniously interacted with the active groups on the surface of SiO2
nanoparticles to promote the strength of the capsules shell.149 As 4. Polymeric–inorganic capsules
shown in Fig. 10e, the cationic amine functionalized SiO2 Compared to polymeric and inorganic capsules, polymeric–inorganic
nanopartilces with an average diameter of 150 nm self-assembled at capsules combine both the easy processing, wide source, flexibility,
the oil/water interface to stabilize the mixture of peppermint oil and and even environmentally responsive properties of organic
cinnamaldehyde droplets. After that, the surface amines on the components and the controllable morphology, and mechanical
nanoparticles reacted with the cinnamaldehyde within the oil phase property of inorganic counterparts.153-155 They therefore have
to form the capsules with the average diameter of 6.7 ± 1.9 µm. The potential as novel functional capsules with the long sustained-release
capsules with the core-shell morphology were determined using an or environmental responsive release property.156-158
oil core loaded nile red and nanoparticles possessing cores labeled
with fluorescein isothiocyanate.
Fig. 11 (a−d) SchemaJc diagrams and corresponding opJcal and (ai−di) electron microscopy images of the diﬀerent phases from emulsion droplet to metal coated
capsule: (a) emulsion droplet, (b) capsule, (c) capsule with adsorbed NPs, (d) metal (Au) coated capsule, (ai) emulsion droplet (optical microscopy), (bi) capsule (TEM),
(ci) capsule with adsorbed NPs (TEM), and (di) metal-coated capsule (SEM). The micrographs correspond to different samples and are chosen to illustrate the evolution
of the systems over the different steps. Reprinted with permission from ref. 161. Copyright 2015 American Chemical Society.
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DOI: 10.1039/C8PY00863A

Fig. 12 (a) Schematic representation of the MF, ripened nanoparticulate CaCO3 and double shell microcapsules. (b) ESEM (LHS) and TEM (RHS) images of the MF, ripened
NP CaCO3 and double shell composite microcapsules. Reprinted with permission from ref. 163. Copyright 2010 Royal Society of Chemistry
The most prevalent method was that the polymeric or inorganic Pickering emulsion droplets to fabricate the sunflower oil-loaded
parts could be interacted onto the surface of the obtained capsules by inorganic–organic double-shell hybrid microcapsules. Interestingly,
chemical grafting, physical adsorption or precipitation.159, 160 The Long and co-workers reported a novel methodology of the double
whole preparation processes are complex and include multistep. For shell composite microcapsules with ripened nanoparticulate CaCO3
example, Hitchcock et al. reported one method for preventing as an outer shell and melamine formaldehyde (MF) polymer as an
undesired loss of encapsulated fragrance oil under the extreme inner shell (Fig. 12).163, 164 The O/W emulsion stabilized by CaCO3
conditions using a simple three-step process.161 As shown in Fig. 11, nanoparticles was formed by mixing the core oil and the aqueous
the emulsion-dispersed phase contained PMMA dissolved in CaCO3 nanoparticle dispersion. Then the stabilized CaCO3
dichloromethane (DCM), a volatile good solvent for the polymer, nanoparticle wall was ripened. The double shell composite
and hexyl salicylate, both a poor solvent for the polymer and the microcapsules were prepared from the ripened CaCO3 microcapsules
encapsulated fragrance. Upon dilution of the emulsion in water, the by adding the pre-crosslinked MF monomer and copolymer to the
DCM is extracted from the dispersed droplets, which induces ripened CaCO3 microcapsule dispersion, and raising the temperature.
precipitation of the PMMA polymer. Under the correct wetting This results in the pre-cross-linked monomer and copolymer
conditions, as DCM is fully extracted (and evaporated), the polymer migrating through the gaps of the ripened CaCO3 nanoparticles and
precipitates at the droplet surface, thus forming a complete shell in situ polymerization at the oil–water interface to form the MF
around the oil core. In the second step, platinum (Pt) nanoparticles polymer inner shell.
were adsorbed on the shell of PMMA microcapsule. Pt nanoparticles In order to simplify the preparation process, in-situ one-step
could be used as a catalyst and nucleation site for gold growth in the method has been developed to fabricate polymeric-inorganic
presence of a reducing agent for the metal ions. Finally, a thin film capsules using different templates such as oil droplets, polymer
of solid gold was grown directly onto the adsorbed platinum colloid and micelles.165 For instance, Wu et al. fabricated organic–
nanoparticle layer using electroless plating. The metal shell was inorganic hybrid microcapsules for the encapsulation of volatile
useful for the improvement of solvent-resistance. The goad coated fragrance molecules by using oil-in-water emulsions stabilized with
PMMA microcapsules prevented loss of small, volatile oils within an the two complex SiO2 as template.166 The amorphous fumed SiO2
ethanol continuous phase for at least 21 days while PMMA capsules and amino-functionalized SiO2 were used to stabilize the volatile
lose their entire content in less than 30 min under the same fragrance and isocyanate emulsion. Subsequently, the adsorbed SiO2
conditions. particles were anchored into a robust polymer shell at the oil–water
When polymer was added into the reaction system after the interface via an interfacial reaction between the polyisocyanates and
formation of inorganic capsules, the obtained capsules kept the inner the hydroxyl groups and/or amino groups on the surface of particles
inorganic and the outer polymeric double shell. Williams et al.162 under alkaline conditions. The permeability and mechanical
first produced an effective Pickering emulsion for sunflower oil properties of the hybrid microcapsules with the mean sizes from 13.4
droplets with Magnafloc/Laponite nanoparticles. After that, to 19.6 µm depend on the ratio of both SiO2 particles. Furthermore,
melamine formaldehyde was precondensated and deposited onto the the thermal responsive hybrid nanocapsules were easily fabricated
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by using poly(n-isopropyl acrylamide-co-styrene) (P(NIPAM-S)) cost, convenient and practicability.

colloids as templates via one step, as shown in Fig. 13a.167 SiO2
nanoparticles from the hydrolysis and condensation of TEOS can be
encapsulated on the surfaces of the P(NIPAM-S) through strong 5. Applications
electrostatic and/or acid–base interactions between the ammonium The capsules are the effective vehicles to protect the flavor and
and amino groups of P(NIPAM-S) and the silanol groups of SiO2, fragrance from degradation, undesired reactions, and most
forming SiO2 shell. Because of the high osmotic pressure, the importantly, from evaporation and leakage.14, 74, 169, 170 The
ethanol in the P(NIPAM-S) gel layer further diffuse into the interior representative flavor and fragrance capsules were summarized in
of the P(NIPAM-S) spheres. Because the reaction medium is a poor Table 1. According to the various application fields, the wall
solvent for the inner polymer chains, these chains fold. Many of the
materials of flavor and fragrance capsules should be designed.

ends of P(NIPAM-S) chains are anchored at the hydrophilic gel Recently, flavor and fragrance capsules have exhibited their
layer, so the inner P(NIPAM-S) chains diffuse outward to form a superiority in food, care products, textile, leather and paper fields.171-
dense hydrophobic shell inside the gel layer. As a result, both the 173
Now we will introduce some important applications in the above
outward diffusion of the inner polymer chains and the accumulation fields, as more and more innovative cases have been reported
of free volume inside the P(NIPAM-S) cores, can cause a confluent recently.
void between the core and the shell, as in the Kirkendall effect. As
the reaction proceeds, the inner polymer chains become completely 5.1 Food and tobacco
diffused into the dense hydrophobic shells and some the chains even The intent of flavor capsules widely applied in food and tobacco
diffused into the voids between nanoparticles, causing P(NIPAM- field is to protect flavor, control the aroma release and prolong the
S)/SiO2 organic–inorganic hybrid hollow spheres with the average preservation period.174 The edible natural polymers including protein
diameter of 220 nm (Fig. 13b). Then the hybrid hollow spheres were and polysaccharide as well as SiO2 should be selected to prepare
directly used to load fragrance in ethanol solution and its loading flavor capsules.175, 176 For instance, utilization of thermal process
capacity kept 32.3 %. Lately, the tiny CS-SiO2 nanocapsules loading flavorings in food industry is expensive and difficult. The
vanillin with the size of 37 nm was prepared with the block encapsulation of flavor with maltodextrin and modified starch can
copolymer (PEO106-PPO70-PEO106) micelles templates.168 provide protection against the degradation reaction, prevent loss of
Polymeric-inorganic capsules loaded with flavor and fragrance not volatile flavors and enhance stability of the flavor core materials.177
only processed the well-defined morphology, multiscale size control Interestingly, when the beef-like flavor produced from enzymatic
from nanometer to micrometer and excellent mechanical properties, hydrolysate of mushroom (A. bisporus) protein was encapsulated
but also achieved the novel environmental-responsive release, which with GA, their sensory profile changed.178 The roasty, savoury and
provide an effective diffusion barrier for volatile and unstable aroma beefy notes of the flavor capsules showed significant increase
compounds. However, to date, polymer-inorganic capsules were first compared with those without encapsulation. Whereas, their
emerging in the field of flavor and fragrance. Most of the available sulphurous and chickeny notes showed opposite trend. In addition,
fabrication methods of polymeric-inorganic capsules encapsulated flavor capsules can be used to reduce the irritation odor of cigarettes
with flavor and fragrance were at the exploratory stage, due to their and prevent the flavor from volatilizing in advance. Cigarettes with
menthol capsules embedded in the filter were first launched in Japan
in 2007.179 The spherical menthol capsule with 3.5 or 4 mm in
diameter and blue to green colour was usually placed in the middle
of the cigarette filter. The outer shell was made from gelatin or a
similar substance.180 Since then, more brands with capsules have
been sold there, such as “Kool” and “Kent” by British American
Tobacco as well as “Marlboro” and “Lark” by Philip Morris.181,182
At the moment, menthol capsule cigarettes are available in at least
40 countries around the globe.
On the other side, the encapsulation of essential oil can effectively
decrease the lipid oxidation value, the loss of antioxidant activity
and the degradation of bioactive compounds during digestion and
extend the shelf life of fish, meat and fruit.183, 184, 185 Cinnamon oil
CS nanocapsules with three sizes of 112 nm, 215 nm and 527 nm
were prayed on the surface of low density polyethylene (LDPE)
films.72 After that, the fresh pork was wrapped with the active films
and preserved at 4 ºC for 15 day. 527 nm-treated CE-NPs exhibited
the excellent antioxidant and antimicrobial property of the pork at
the end of the refrigerated storage. In all, CE-NPs with the big size
have more potential as a natural preservative to maintain the quality
Fig. 13 (a) Schematic representation of the preparation of thermal responsive
of meat and meat products. In addition, the avocado oil and olive oil
hybrid hollow spheres; (b) TEM and (c) SEM of the spheres. Reproduced from Ref. nanocapsules with polycaprolactone and PEG–polybutylene adipate–
167 with permission from the Royal Society of Chemistry. PEG as wall materials were useful for preserving fruit.186
Page 11 of 20 Polymer
Please do not Chemistry
adjust margins
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Table 1 Summary of the representative flavor and fragrance capsules
Wall-material Synthesis method Core material Size (µm) Ref.

Orange oil 21µm 50
Spray-drying
Vanillin 8 µm 215
CS
Tuberose fragrance 174nm 69
Ionic gelification 112, 215, 527
Cinnamon oil 72
nm
Saccharomyces Cerevisiae cell Spray-drying D-limonene / Ethyl hexanoate 5.7-9.1 µm 52
Whey protein isolate Spray-Freeze-Drying Soluble coffee 91.1µm 55

Short linear glucan In situ nanoprecipitation Menthonel oils 93-113 nm 87
Alginate Electrospray Peppermint natural oil 80-900 µm 57
AHSG Electrospray D-limonene 6-18 µm 59
Thymol/vanillin NR 76
CD Inclusion complexation
Isopulegol NR 77
High amylose starch Inclusion complexation Limonene/menthone NR 86
GA-CS Complex coacervation Patchouli oil 12.81µm 68
GA-MD Spray-drying Osmanthus 7.34 µm 196
Melt-dispersion Mentha oil / Piperita oil 226-331 nm 96
PEG
Polymeic Melt-dispersion/PGSS Coffee oil 78 µm 97
Jasmine oil 5-30 µm 93
PMMA Solvent evaporation
Hexyl salicylate/cyclamen aldehyde 1-5 µm 94
PBCA Anionic polymerization Rose 67.3 nm 121
PBDDMA Interfacial polymerization Peppermint oil 261 nm 135
Polyacrylate Miniemulsion polymerization Lilial 67.78 nm 222
Isosorbide Interfacial polymerization Neroline 27 µm 130
Polyamide Interfacial polymerization Toluene 200-350 µm 134
Emulsion polymerization α-pinene 121-148 nm 217
PMMA/PS/acrylic acid Miniemulsion process 1,2-dimethyl-1-phenyl butyramide < 100 nm 106
PMMA/ BMA / MAA/ BDDMA Emulsion polymerization α-pinene < 200 nm 107
NIPAM/PMAA Interfacial polymerization Coumarin 550 nm 136
Polyuria/polyurethane In-situ polymerization Romascone 10 µm 131
Complex coacervation /
Polyuria/ Protein Fragrances oil NR 132
Interfacial polymerization
Complex coacervates/ In situ
Gelatine–CMC/MF Limonene NR 220
nanoprecipitation
Lemon oil 233 nm 145
Sol-gel method Farnesol 0.44-0.94 µm 146
SiO2 Fragrances 150-200 nm 147
Inorganic
Hexyl acetate 2.17 µm 148
Pickering emulsion
Peppermint oil 6.8 µm 149
CaCO3 Pickering emulsion Limonene 15-20 µm 152
PMMA-Au Cosolvent extraction Hexyl salicylate 4 µm 161
Laponite-MF Pickering emulsion Benzyl benzoate 54±24 µm 162
Polymeric– CaCO3 -MF Pickering emulsion Fragrance mixture 13-15 µm 163

inorganic SiO2-Isocyanates Pickering emulsion Salicynile/ Cyclosal/ 13.4-19.6 µm 166
SiO2 -P(NIPAM-S) Template Cyclamen aldehyde 220nm 167
SiO2-CS Interfacial condensation Vanillin 37nm 168
* NR, the mean is not reported in the original research article;
Recently, flavor capsules can also be used to maintain natural Ceriali et al. extracted liquid coffee essence from coffee beans as a
color and flavor, and improve water-solubility of the beverage.187 flavoring material for instant coffee beverages and then coated them
This journal is © The Royal Society of Chemistry 20xx Polym. Chem., 2018, 00, 1-3 | 11
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DOI: 10.1039/C8PY00863A
with maltodextrin.188 When the coffee capsules were added to hot their activity and may also generate degradation products that can act
water, they dissolved quickly and released the strong coffee aroma. as contact allergens.191 Encapsulation technology can provide the
And these coffee capsules would not produce oil slicks to affect the chemical stability, prevent the skin from irritation, and allows
flavor quality of the coffee beverage. A popular kitchen spice, clove control of the release of the precious and volatile aroma
bud (Syzygium aromaticum L), having strong flavour and pungency compounds.192-194
characteristics was extracted to produce Clovinol. Then Clovinol For instance, the microencapsulation of green coffee oil
capsules were prepared by encapsulated with gelatin. The capsules microcapsules with modified starches or GA with maltodextrin as
were easily soluble in a variety of beverage matrices such as juice, the walls materials not only improve the oxidative stability of the oil,
yogurt, honey and drinking water without any sedimentation and but also provide a strategy to use the green coffee oil for power
provided a very pleasant clove aftertaste with a unique feel in the cosmetic products. This reduced the allergenic effect of cinnamic

mouth.189 acid that can cause allergy when applied directly over the skin.195
Similarly, osmanthus fragrance was encapsulated into GA and
5.2 Care product maltodextrin capsules. The average size of the microcapsules was
In order to enhance the aromatic perception of care product, 7.34 ±2.41 µm. There were small openings in the shell materials, and
fragrance and essential oils are added into the formula of many the fragrance might have permeated through those small openings
consumer products such as cosmetics, shampoos, body washes, and then contacted the air and volatilized. The fragrance retention
detergents and so on.190 However, fragrances are highly volatile rate of the microcapsules after 100 days exceeded 90 % and after 6
compounds that easily evaporate during application. Meanwhile, months was still 71 % at room temperature, which exhibited a good
many fragrances, such as aldehydes and ketones, are prone to ability for extending the time of aroma reservation. Besides, the
oxidation under ambient conditions, which can lead to a rapid loss of transdermal release experiments proved that the fragrance in the
microcapsules could stay longer at the surface of the skin than in the
pure fragrance oil.196 The Procter & Gamble Company (P & G)
reported that acrylic polymer microcapsules encapsulated with a
mixture of volatile aroma substances and an additive were prepared
via emulsion polymerization. The melting point range of the mixture
was controlled from -20 to 60 ºC. Then the fragrance capsules with
7% to 20% were added into the laundry detergent, fabric softener,
cleaning products and shampoo.197. Lately, P &G manufactured a
simple laundry fragrance capsule, which was successfully launched
and well accepted in the market in 2017. PEG with the molecular
weight from 5000 to 11000 was melt and blended with fragrance,
and then the fragrance capsules with the dimension of 40mm were
obtained after cooling.198 Strictly speaking, this capsules were only
the carrier in large dimension for fragrances.
Although many works have done on the encapsulation of
fragrance in capsules, the efficient deposition of fragrance and
fragrance capsules from a shampoo medium onto hair is a
challenging task. For this reason is that the primary function of a
shampoo is to cleanse the hair surface by removing hydrophobic
molecules such as noncovalently bound lipids and dust particles.199
The hydrophobic fragrance localized inside the micelles, so that
these micelles can be easily rinsed off with water.200, 201 Recently,
phage-display-identified peptides that can bind to human hair under
shampooing conditions are first identified and subsequently used to
enhance the deposition of fragrance capsules.131 The peptide-
functionalized (10 wt%) polyurethane/polyurea-type core-shell
microcapsules containing a model perfume resulted in approximately
Fig. 14 (a) Stability against surfactant-driven leakage for encapsulated model
volatiles: side-by-side comparison of standard coacervate-only capsules and a 20-fold enhancement of their deposition onto human hair
composite coacervate/poly-urea capsules upon exposure to a surfactant solution. compared to the fragrance microcapsules without peptide.
(b) Typical adhesion force curves measured in pull-off tests for composite Interestingly, the biopolymer-based shell materials, such as those
protein/polyurea (top) and classical polyurea (bottom) capsules; the normalized
formed from protein/polysaccharide coacervates, may offer
adhesive force is shown as a function of the displacement Δz normalized with the
capsule diameter D. (c) Evaluation of the delivery of volatile fragrance compounds
favorable adhesive properties on a wide range of substrates.202, 203
from a model surfactant solution assessed by an untrained human sensory Dardelle et al. synthesized core/shell capsules with composite shells,
evaluation panel (schematic drawing shown on top). The samples were combining a strong chemical barrier formed by synthetic polyurea
formulated as follows: a. contains 1.2% w/w free fragrance oil only, b contains with the outstanding adhesive properties of protein based complex
1.2% w/w oil encapsulated in coacervate-only capsules, c. contains 1.2% w/w oil
coacervates.132 As shown in Fig. 14, the coacervate/polyurea
encapsulated in traditional polyurea-only capsules, and d. contains 1.2% w/w oi l
encapsulated in the protein-based complex coacervates/polyurea capsules. composite capsules indeed reveal strong negative adhesive force
Reprinted with permission from ref. 132. Copyright 2017 Wiley & Sons, Ltd.
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peaks in comparison to the capsules with simple polyurea shells. The

resistance of the composite capsules against leakage of the
encapsulated molecules in model solutions of the anionic surfactant
SDS was assessed (Fig. 14a). The composite capsules are
significantly more stable against loss of the encapsulated oil into the
SDS solution as compared to the coacervate-only capsules. In
particular, after 15 h the shells of the classical coacervate capsules
appear highly swollen and the core/shell structure has disintegrated.
In contrast, the shells of the composite capsules remain intact even
after extended exposure to the surfactant solution, thus preventing

the premature release of fragrance. The behavior of the fragrance
capsules under SDS solution was evaluated using human sensory
panel tests (Fig. 14c). The olfactive intensity values of the composite
capsules increased significantly from 1.1 ± 0.8 to 3.1 ± 0.6 upon
lathering among all the samples.
5.3 Textile
Recently, the aromatic textiles as one of the most attractive
functional textiles exhibited antiparasitic,173, 204 antibiotics, and
refreshment.135, 205 The key of the aroma textile is to remain the
aroma on the textile for more than 6 months and withstanding
washing cycles.206-208 Therefore, the size and chemical properties of
flavor and fragrance capsules should pay more attention. For Fig. 15. Peptide-enhanced selective surface deposition of (a) a PHPMA–peptide
instance, patchouli oil microcapsules prepared via a complex conjugate based model polymer profragrance; (b) fragrance-loaded peptide
coacervation method were grafted onto cotton fabrics with 1,2,3,4- modified polymer nanoparticles; (c) Percentage deposition of linear polymers
butanetetracarboxylic acid (BTCA) as the crosslinking agent.209 onto cotton; (d) Photograph of cotton fabric samples excited at 365 nm with an 8
W fluorescent lamp following their incubation with 0.2 mg mL−1 of PHPMA
After 30 days, the patchouli oil in the microcapsules still remained
conjugates; (e) Percentage deposition of PS-co-PAA nanoparticles onto cotton; (f)
on the fabric, and the release amount was close to 50%. Then, Headspace concentration of α-pinene following the treatment of cotton fabric
aromatic cotton fabrics were generally obtained with several samples. Reproduced from Ref. 217 with permission from the Royal Society of
chemical crosslinking agent, including BTCA, glutaraldehyde,210 Chemistry.
glyoxal,211 formaldehyde,212 and formaldehyde derivatives.213 these nanocapsules after 20 washing cycles was clearly lower than
However, these crosslinking agents produced health and that by rose fragrance alone.121
environmental problems for people.68 Interestingly, Günay et al. reported that the appropriate cotton
With the enhancement of environmental safety consciousness, the binding peptides ligand can be used to enhance the deposition of
addition of natural crosslinking agents or physical functions to fragrance nanocapsules on cotton substrates.217 As shown in Fig. 15,
textiles has exhibited superiority over the addition of chemical the first are linear, dansyl cadaverine labeled poly(N-(2-
crosslinking agent for aromatic cotton fabrics.204, 214 Yang et al. hydroxypropyl) methacrylamide) (PHPMA)–peptide conjugates,
prepared vanillin/chitosan microcapsules with a mean size of 8 µm which serve as a model for polymer profragrances (Fig. 15a). A
via spray-drying and then applied them to cotton textiles with citric second polymer-based delivery system that has been explored is α-
acid as a safety crosslinking agent.215 Besides, β-cyclodextrin(CD) pinene loaded poly(styrene-co-acrylic acid) (PS-co-PAA)
was incorporated in cotton fabric following pad-dry-cure technique nanoparticles, which have been prepared via miniemulsion
employing maleic anhydride as modifying agent under the dual polymerization (Fig. 15b). By adjusting the amount of Pep1, the
influence of free radical polymerization catalyst ammonium surface deposition of these linear polymers on cotton can be
peroxodisulfate and esterification catalyst tetrasodium increased by two to three times as compared to a control (the linear
pyrophosphate.216 The retention of fragrance for maleic anhydride PHPMA polymer) that does not contain the peptide. The increased
finished cotton fabrics are commonly found to be far higher even brightness of the substrates upon increasing the amount of Pep1 is
after 15 wash cycles. These microcapsules could not effectively consistent with an enhanced surface deposition of the conjugates.
penetrate into the fibers because of the limitation of their big size. Analogous to the linear polymer–peptide conjugates, incorporation
CS nanocapsules (130 nm) loaded with a sweet osmanthus fragrance of Pep1 into the PEGylated PS-co-PAA nanoparticles also resulted in
were applied onto the cotton fabrics directly without any an almost twofold increase in surface deposition of conjugates to the
crosslinking agents. Most components of osmanthus fragrances in cotton samples. Deposition of α-pinene loaded NP2-Pep1 particles
the cotton fabrics treated with osmanthus fragrances were lost resulted in a further increase in fragrance release from cotton fabric
completely after 20 washing cycles, compared with those with the surfaces, such that 50% higher α-pinene release was detected for
nanocapsules.71 Similarly, PBCA nanocapsules (67.3nm) NP2-Pep1 as compared to NP2-PEG.
encapsulated with a rose fragrance were applied to the cotton fabrics
directly. The fragrance released from the cotton fabrics finished by 5.4 leather and paper
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Many years ago, flavor and fragrance were utilized to cover the synergistic effect of chitosan and essential oils enhanced the
undesirable odor given out from the leather and paper.218 antimicrobial efficacy of the aroma leather.225
Nevertheless, most of aroma ingredients are easily to be lost and Recently, the aromatic wallpapers were produced by soaking HP-
degraded during the storage. The developments of flavor and β-CD microcapsules loaded with osmanthus fragrance.226 Aromatic
fragrance capsules not only solve the above problems, but also wallpaper could meet the requirements of consumers, possess a
improve the aroma retention time of the final products.219 For relative stable character and prolong the time of fragrance staying at
example, gelatine–carboxymethylcellulose (CMC) and melamine– wallpapers for more than three months.
formaldehyde (MF) resin-based microcapsules containing limonene
were prepared using complex coacervation and in situ
polymerization processes, respectively.220 Both the microcapsules 6. Conclusions and prospects

were incorporated into the leather and paperboard for footwear This review highlights the most important synthetic methods and
application. MF microcapsules showed the higher durability against applications of flavor and fragrance capsules. The relative advances
stringent thermal and mechanical conditions than CMC in the synthesis and properties of these capsules have paved the way
microcapsules. In fact, the leather was a kind of three-dimensional to a huge range of the encapsulation of sensitive and active
retiform structure, composed of collagen fiber bundles. The chrome molecules with many potential applications. In this article, we have
tanned sheep leather has an average pore diameter of 385 nm. reported selected examples of flavor and fragrance capsules
Therefore, the size of flavor and fragrance capsules would obviously according to the kinds of wall materials including (i) polymeric, (ii)
affect the aroma effect of the leather.221 The leather finished by inorganic, (iii) polymeric - inorganic. We have also reported the
polyacrylate nanocapsules loading lilial (PNLs) with the size of applications of flavor and fragrance capsules.
67.78 nm and loading capacity of 36.83% showed the excellent Polymeric capsules are the most mature and efficient vehicle to
sustained-release property.222 When the leather was treated with the protect the volatile aromatic compounds from lost, undesired
lilial emulsion and PNLs, respectively, the surface of the leather reactions, evaporation and leakage. Both physical and chemical
became coarse, and some spherical particles adhered on the surface reactions were used to fabricate flavor and fragrance capsules
of the leather fibers, as shown in Fig. 16(c,e). After they were flexed whether the wall material is natural polymer or synthetic polymer.
5000 times, small or no residual lilial emulsion particles remained on Physical method is the early developing approach to broaden the
the fiber surface [Fig. 16(d)]. However, there was a big aggregation industrial road of flavor and fragrance capsules, due to its simplicity,
of particles dispersed on the surface of the leather finished by the convenience, and low-cost. However, the morphology and
PNLs [Fig. 16(f)]. In addition, some essential oil capsules can encapsulation effect of flavor and fragrance capsules are nonetheless
provide long-lasting antibacterial property for leather. In addition, unsatisfactory. Chemical reaction has been embraced by many
some essential oil capsules can provide long-lasting antibacterial researchers in recent year for its universality and functionality.
property for leather.223 Lemongrass oil containing polyphenols can Inorganic capsules provide advantages such as significant chemical
alter metabolism, leading to death of the bacteria.224 When and physical stability and excellent controllable morphology.
lemongrass oil was encapsulated into CS nanocapsules, the However, these inorganic capsules only focus on certain special
materials such as SiO2 and CaCO3. The release of aroma from flavor
and fragrance capsules was achieved by adjusting their surface
pores.
Polymeric-inorganic capsules are a new rising category based on
the existing fabrication methods of capsules. This is due to the well-
defined morphology, multiscale size control and more importantly,
excellent mechanical properties and novel environmental-responsive
release property of flavor and fragrance capsules.
Flavor and fragrance capsules effectively protect the active
ingredients from oxidation and degradation; control the release of
aroma compounds from the products, showing the wide application
of food, tobacco, textile, care product, leather and paper fields.
Some interesting fabrication strategies and their formation
mechanisms have been proposed in the past few years, but each
method has its strengths and weaknesses. This provides us with
important research opportunities. In particular, we believe that the
following several aspects, should pay more attention in the
development of capsules for active ingredients:
i) Because flavor and fragrance capsules can be either polymeric,
inorganic, or polymeric-inorganic wall material, or the different
Fig. 16 SEM results of the (a,b) untreated leather, (c,d) leather finished by lilial properties of polymeric and inorganic components, a large number
emulsion, and (e,f) lilial nanocapsules (c,e) without flexing and (d,f) after flexing
of capsules with various chemical compositions and morphologies
5000 times. Reprinted with permission from ref. 222. Copyright 2013 Wiley
Periodicals, Inc.
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A table of contents

The preparation methods and application of flavor and fragrance capsules based on
polymeric, inorganic and polymeric-inorganic wall materials were summaried.

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Preparation and Application of Flavor and Fragrance Capsules

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to three wall materials: polymeric, inorganic, and polymeric-

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

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by using poly(n-isopropyl acrylamide-co-styrene) (P(NIPAM-S)) cost, convenient and practicability.

materials of flavor and fragrance capsules should be designed.

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Wall-material Synthesis method Core material Size (µm) Ref.

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Polymeric– CaCO3 -MF Pickering emulsion Fragrance mixture 13-15 µm 163

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peaks in comparison to the capsules with simple polyurea shells. The

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Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

Polymer Chemistry Accepted Manuscript

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