Applications of Maleic Anhydride Chemistry…

MAY 2015 • Vol. 21 No. 5
New York Society of Cosmetic Chemists
www.nyscc.org
Applications of Maleic Anhydride Chemistry
in Skin Care, Biomedical Devices, and Transdermal Delivery
Part III
… by Roger L. McMullen
I
n the first two articles of this series we discussed several applications
of maleic anhydride chemistry to phenomenon occurring in skin.
Numerous examples of the use of maleic anhydride and its derivatives
can be found in patent publications and the literature. Polymers of maleic
anhydride are especially well known for their bioadhesive properties, and
are used extensively in the biomedical industry. Somewhat related, the same
types of polymers found their way into personal care adhesive strips designed
to remove unwanted keratotic debris. In a much different application, maleic
anhydride derivatives made headway into antiperspirant formulations where
they help to reduce the concentration of aluminum salts. Transdermal drug
delivery is another explosive area where hydrogels made of maleic
anhydride polymers act as key ingredients of the delivery formulation.
In this third and last article of this series, we touch upon some of the
other applications of maleic anhydride and its derivatives in skin care. In
the first section, we focus on the chemical modification of maleic anhydride
with skin care active ingredients, which are delivered to the skin surface,
made possible by a biological binding mechanism of the maleic anhydride
portion of the molecule with the skin, followed by subsequent release of
the active. Throughout the remainder of the article, further emphasis is placed
on the use of maleic anhydride derivatives in various skin care formulations
as skin care emollients, adjuvants in skin cleansing formulations, soap bar
stability agents, antioxidant stabilizers, auxiliary agents for alpha hydroxy
acids, sunscreen formulating agents, rheology modifiers, and skin tightening
agents.
1. Delivery of active ingredients
T
here are many compounds in the cosmetic industry that are used to improve the health state of skin. These active ingredients typically
have some biological activity and can modulate important processes in the skin. Examples of such ingredients include antioxidants,
biologically active peptides, and sunless tanning agents. Other active ingredients such as sunscreens, anti-acne agents (e.g., retinol),
antiperspirant actives, whitening agents, and dandruff products are regulated by the FDA and are considered OTC drugs. The delivery of
these molecules to skin is paramount to their ability to be functional. Often times this includes choosing the correct formulation vehicle,
and sometimes can even mean encapsulating products in a variety of vesicles for effective delivery. The lack of affinity to the skin can
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G O L F
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J U LY 2 9 • C R Y S T A L S P R I N G S R E S O R T, H A M B U R G , N J
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2015 NYSCC
BOARD OF
DIRECTORS &
PROGRAM CHAIRS
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CHAIR
Kim Burch
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New York SCC 60th Anniversary
Gala Masquerade Ball
October 24, 2015
Come help us celebrate and honor our past chapter chairs
at a formal/black-tie optional Gala Masquerade Dinner/Dance
event to be held at the Marriott Glenpointe in Teaneck, NJ
on Saturday, October 24, 2015.
Cost: $100.00/person
Cocktail reception begins
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If you have any old photos
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NYSCC
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DISCOVER
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INDIA
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S YMPOSIUM
2015 Seminar Focus – India:
Tapping the Emerging Personal Care Market
Renaissance Woodbridge Hotel, Iselin, NJ
Clic
May 11, 2015
Herek
8:00 a.m. – 5:00 p.m.
Online registration: https://nyscc.org/events/nyscc-discover-india-symposium/#registration.
Event Co-chairs: Steve Herman and Kamesh Yerramilli
8:00 a.m. – 9:00 a.m.
Registration
9:00 a.m. – 9:15 a.m.
Opening remarks – Steve Herman and Kamesh Yerramilli
9:15 a.m. – 10:00 a.m.
10:00 a.m. – 10:45 a.m.
Dr. Satish Goel, Ph.D. (Unilever) –
Innovations in Personal Care: Catering to Diverse Consumer
Needs in India
10:45 a.m. – 11:00 a.m.
Break
11:00 a.m. – 11:45 a.m.
Mr. Rashmikant Mohile (CLAIMS India) –
Cosmetic Regulations in India
11:15 a.m. – 12:00 p.m.
Dr. Kumar Vedantam, Ph.D. (Givaudan) –
Fragrance Delivery and Benefits in Indian Cosmetic Products
12:00 p.m. – 1:30 p.m.
4
Mr. G. Ramakrishnan (Galaxy Surfactants) –
Growth of the Personal Care Industry in India—2015 and Beyond
Lunch
1:30 p.m. – 2:15 p.m.
Ms. Vivienne Rudd
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Spotlight on India –
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Ms. Punita Kalra
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Male Grooming Product
Markets, Innovations,
and Consumer Trends
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3:00 p.m. – 3:15 p.m.
Break
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Prof. Pratap Bahadur
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Indian Cosmetic Industry:
A Chemist’s Perspective
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Indian Cultural Event –
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About the Event
A member of the rising economic powers, otherwise
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Your Beauty.
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Applications of Maleic Anhydride Chemistry…
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(Continued from page 1)
hinder the molecule’s efficacy. A creative approach to ensuring that agents are delivered in a sustained
manner is to utilize a non-toxic, biologically compatible binding agent that has affinity for the skin and is
also capable of binding active ingredients that can then be ferried to the skin’s surface.
In the first article of this series we discussed the bioadhesive properties of maleic anhydride chemistry
with the skin, although we did not discuss the interactions or possible chemical affinity between maleic
anhydride and the skin. A likely mechanism for the enhanced affinity of maleic anhydride and its derivatives
toward skin and other biological tissue could likely stem from possible covalent interactions between the
hydrolyzed form of succinic anhydride (succinic acid) and various amino acid residues. Figure 1 provides
a possible explanation for the binding of maleic acid with proteins via side chain groups of amino acids,
such as amino, sulfhydryl, carboxyl, or hydroxyl functionalities.1
Figure 1: Reaction of succinic anhydride with side-chains of amino acids.
There are numerous examples of different types of compounds that can be bound to maleic anhydride.
For example, Figure 2 demonstrates the attachment of ascorbic acid, an important antioxidant for skin health.
Other molecules that could similarly be bound to maleic anhydride consist of glycerol and benzophenone3. In general, one would expect that with enhanced binding at the surface of the skin via the maleic
anhydride moiety of the molecule, there would be greater probability that these molecules would carry out
their function in skin. There are a number of examples in the literature of molecules that can be attached to
succinic anhydride for delivery to the skin such as humectants (e.g., glycerol) and sunscreens (e.g.,
benzophenone-3).1
Figure 2: Succinic anhydride covalently linked with ascorbic acid.
It should be noted that this type of approach, while inventive, does not discriminate as to the location
of the delivery of the cosmetic agent. For example, there may be certain compounds that would penetrate
deep into the epidermis while others would preferentially remain on the surface.
It is often desirable to deliver lipophilic ingredients to the skin, which have poor aqueous solubility.
Normally, this is accomplished by incorporating the ingredient in an oil-in-water or water-in-oil emulsion
that is directly applied to the skin in the form of a cream or lotion. In some cases, such compositions can
be aesthetically unpleasant or unstable with limited extended shelf-life. More sophisticated delivery systems
have been gaining popularity in recent years. One example is a polymer/lipid macromolecular complex that
is used to deliver oil-soluble, hydrophobic ingredients to the skin.2,3 These complexes are engineered utilizing
copolymers of poly(styrene-maleic anhydride) and phospholipids. Normally, an oil-soluble delivery agent
is solubilized in a phospholipid micelle (e.g., dilaurylphosphatidylcholine or dipalmitoylphosphatidylcholine)
and then combined with the polymer before adjusting the pH.
It has been postulated that the lipids in combination with the polymer form discoidal (disc-shaped)
micelles in which the lipids form a bilayer core. It is believed that the polymer is in an alpha-helical
conformation with one face occupied by nonpolar groups (styrene monomers) and the other with polar
groups (maleic anhydride monomers).4 Figure 3 shows an illustration of the macromolecular complex.
Evidence of such structures has been confirmed by cryo-TEM measurements.5 This technology has been
proposed for both pharmaceutical and topical cosmetic application. The copolymer can be an alternating
or block copolymer of poly(styrene-maleic anhydride); however, this will influence the secondary structure
of the polymer.
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Figure 3: Illustration of a discoidal polymer/lipid macromolecular complex containing
poly(styrene-maleic anhydride) and phospholipids. Originally printed in Reference 5.
2. Skin care formulations
Maleic anhydride derivatives are utilized in a variety of skin care formulations where they are used as
emulsifiers, emollients, gelling agents, and soap additives. Skin care formulations are usually classified as
leave-on or rinse-off. Leave-on treatments usually refer to creams, lotions, body milks, etc. They are applied
to skin and absorbed by the stratum corneum through mechanical manipulation (rubbing and massaging).
On the other hand, rinse-off skin care products may consist of soap bars, body washes, foaming cleansers,
etc. Usually, the toxicological profile for leave-on products must meet relatively strict guidelines to avoid
possible sensitization reactions during use, which could result in contact dermatitis or even more serious
skin or ocular conditions.
2.1. Applications of skin care emollients
Emollients are skin care ingredients that are used in cream, lotion, or gel formulations that, upon
treatment, make the skin more soft and supple. With respect to maleic anhydride, research activity in this
area has focused on creating adducts of vegetable oils with maleic anhydride.6,7 Specifically, the desire is to
create an adduct of maleic anhydride with the principal component of castor oil, ricinolein, which is the
triglyceride of ricinoleic acid. Castor oil is obtained from the seeds of the plant, Ricinus communis, and is
sought after for its therapeutic properties in skin care formulations.
Figure 4: Molecular structure of maleated ricinolein, the chief component of castor oil.
Figure 4 provides the structure for the maleated analogue of ricinolein where it is shown that one of the
triglyceride chains is chemically modified with maleic anhydride. A number of compositions for both rinseoff and leave-in formulations have been described in the literature.8-10 However, due to skin sensitization, it
usually recommended that maleated castor oil be used in rinse-off applications, and at concentrations that
do not exceed 0.5% (w/w). It should be noted, however, that when used in liquid surfactant systems (e.g.,
body washes) maleated castor oil helps to reduce surfactant-induced irritation and perturbation of the skin’s
lipid barrier.11 When combined with palmitic acid, maleated castor oil forms a highly ordered lamellar gel
analogous to that found in the lipid barrier (in the stratum corneum) of healthy skin.12 It is believed that
these ordered structures can fortify the lipid matrix of the stratum corneum.
Maleated soybean oil and maleated sunflower oil are also two popular cosmetic incredients. In general,
any oil that is not completely saturated can be maleated such as avocado, coconut, corn, cottonseed, jojoba,
linseed, nut, olive, palm, raisin, rapeseed, safflower, sesame, squash, and sunflower.13 There are numerous
examples in the literature demonstrating the modification of natural oils with maleic anhydride.14-17
Furthermore, maleated oils may be modified by reaction with water ultimately forming a maleic acid
derivative or with a hydroxide resulting in the corresponding salt form.13 Such chemical modification could
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lead to many additional possibilities in regard to functional moieties that could be included in the oil, while
at the same time maintaining a renewable/sustainable molecule. A major advantage of introducing the polar
functionality of maleic anhydride into the backbone is an increase the molecule’s overall water solubility.
Moreover, this lends favorably to the ability of the oil to self-emulsify.18
Figure 5: Molecular structure of (A) chitosan and (B) maleated chitosan.
Other interesting applications in skin care include modification of polysaccharides with maleic
anhydride to obtain functional moisturizing ingredients. Chitosan derivatives are a good example of
molecules that have been engineered by acylation of chitosan with maleic anhydride.19 Chitosan is derived
from chitin, which is a polysaccharide of N-acetylglucosamine units linked together by a β-1,4’ bond. Chitin
is naturally found in the exoskeleton of crustaceans and insects. Chitosan is obtained by a deacetylation
reaction of chitin; however the reaction is not complete and chitin is usually a mixture of both glucosamine
and N-acetylglucosamine units.20 Figure 5 (page 8) presents the structure of both chitosan and its maleic
anhydride derivatized counterpart. As shown in the figure, maleic anhydride is attached to chitosan via the
amine group at the 2-position on the glucosamine ring. One of the key motivations for modifying chitosan
is due to issues with solubility. Unmodified chitosan is insoluble in alkaline medium and, in fact, is only
soluble in acid medium in the form of salts.
Maleic anhydride based materials may also be used as emulsifiers in emulsions systems. An emulsion
is a heterogeneous system in which two or more immiscible liquids or semi-solid materials are dispersed in
another liquid in discrete droplets. The materials that are dispersed (or emulsified) form the dispersed or
internal phase, while the rest of materials form the continuous phase or external phase. There are a variety
of emulsion types that consist of oil-in-water (o/w), water-in-oil (w/o), multiple (oil-in-water-in-oil; water-inoil-in-water), nano-, micro-, and Pickering emulsions (a type of oil-in-water emulsion). O/W emulsions are
probably the most commonly employed vehicles in skin care formulations, which contain an oil phase
dispersed in an aqueous continuous medium. A schematic representation of a dispersed droplet in a w/o
emulsion is shown in Figure 6. An emulsifier (or emulsifying agent) is an amphipathic molecule, which
arranges itself at the interface between the two immiscible phases (o/w), thus reducing the surface (interfacial)
tension between the two phases, and is able to disperse oil droplets in water. When used with o/w emulsions,
they arrange themselves with the hydrophobic tails in the oil (internal) phase and hydrophilic heads in the
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One example of a polymeric maleic anhydridebased emulsifier is poly(isobutylene) succinic anhydride.
This polymer is obtained by reacting poly(isobutylene),
which contains vinylidene end groups, with maleic
anhydride.21 As a result, one obtains a polymer with
a hydrophobic interior and an end-capped polar
functionality. One of the benefits of this molecule is its
low degree of color. It should be noted that the
polyolefin portion of poly(isobutylene) succinic
anhydride is extremely hydrophobic, while the maleic
anhydride modified end group is only slightly polar.
Further reactions can be carried out with the maleic
anhydride portion of the molecule using more highly
polar species, resulting in greater surface activity of the
polymer.
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Figure 6: Illustration of a dispersed oil droplet in a
typical o/w emulsion stabilized with an emulsifier.
2.2 Skin cleansing formulations
In general, skin-cleansing products are manufactured in the form of solids (bars), liquids, or gels. Their
function is to clean the skin by removing excess oils, dirt, and dead, sloughed skin cells on the surface.
Historically, soap was universally used as a cleansing agent. Soaps are fatty acid salts that are manufactured
by saponification of vegetable oils or animal fats. There were many safety concerns regarding the use of
soaps and their role in causing irritation, dryness, scaling, and roughness. This led to the development of a
variety of anionic, amphoteric, and nonionic surfactants with less skin irritation potential that could be used
in skin detergents. In modern skin cleansing formulations, the most commonly used ingredients are anionic
surfactants, which often include acyl phosphates, acyl sarcosinates, alkylaryl sulfonates, alkyl ether sulfates,
alkyl sulfates, isethionates, and olefin sulfonates.22 Even with the development of this new arsenal of
ingredients, there are still many reported cases of skin irritation. Therefore, milder skin cleansing formulations
are often sought after. Terpolymers of alpha olefin and maleic anhydride were suggested irritant reducing
agents in skin cleansing formulations.23 The alpha olefin monomers consist of a shorter chain 1-alkene and
longer chain 1-alkene having at least 18 carbon atoms. Therefore, the composition consists of a maleic acid,
short chain aliphatic, and long chain aliphatic monomeric components.24 The polymer is 49-60 mole percent
of maleic anhydride, 10-40 mole percent of shorter chain olefin, and 40-10 mole percent of long chain
olefin. By adjusting the ratio of the shorter and longer aliphatic monomers, one may fine-tune the solubility
and waxiness of the polymer. The use of this polymer, which can reach as high as 50% of the total surfactant
concentration in cosmetic detergents, reportedly does not comprise its foaming and cleansing properties.25
2.3 Soap bar dimensional stability
Soap bars are used almost universally to clean the skin. There are, of course, inherent problems with
the stability of the soap bar during its life in the shower. As the soap bar ages, cracking occurs in its structure
due to the presence of water. More than likely, such an effect occurs due to changes in the crystalline phase
of the soap bar caused by residual moisture. Studies by Colgate-Palmolive have shown that incorporation
of polymers based on maleic anhydride, specifically poly(methyl vinyl ether-maleic anhydride) and its
esterified form, reduce the number of cracks in the soap bar and help to maintain its dimensional stability.26
Further, the author reports an emollient effect for such compositions coupled with a smoothening effect
when applied to skin. In general, other types of polymers have been used in similar applications.
Unfortunately, the mechanism by which soap bar dimensional stability is conserved is unknown.
2.4 Stabilization of vitamin C
Vitamin C, or ascorbic acid, is an important antioxidant in skin that prevents free radical damage,
stimulates collagen synthesis, boosts the immune response, and acts as a synergistic antioxidant with vitamin
E (alpha-tocopherol).27 Unlike other mammalians, humans lack an enzyme required for vitamin C
biosynthesis. Therefore, it must be obtained through the diet or by topical treatment. However, a major issue
with formulating ascorbic acid in skin care preparations is its inherent instability. Several approaches to
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circumvent this instability issue include: packaging that provides a more inert atmosphere thereby preventing
oxidation; creating a two phase formula in which one is a dry powder (containing vitamin C) and the other
is liquid—they are combined immediately prior to use; formulating with high concentrations of glycols or
polyols to reduce the solubility of oxygen in the formulation; and formulating ascorbic acid in an anhydrous
system based on silicones.28 There have even numerous attempts to synthesize vitamin C derivatives, such
as sodium ascorbyl phosphate or ascorbyl palmitate; however, the bioavailability of these materials is
reportedly low.29 In recent years, there has been some patent activity by L’Orèal utilizing low molecular
weight poly(styrene-maleic anhydride) chemistry to prevent oxidation of ascorbic acid in skin care
formulations.30-35 Unfortunately, the precise mechanism by which the polymer prevents oxidation is not
disclosed, or not fully understood.
2.5 Alpha hydroxy acids
Another important class of compounds for the treatment of skin is hydroxy acids.36 These consist of
alpha hydroxy acids, beta hydroxy acids, and polyhydroxy acids. Alpha hydroxy acids are the most important
in this group and have had considerable success in the personal care marketplace. Structurally, alpha refers
to the position of a hydroxyl group on the carbon adjacent to the carboxylic acid functional group in these
molecules. These agents incur biologically induced changes in skin resulting in anti-aging, anti-wrinkle
activity, and improved skin tone. The most common alpha hydroxy acids in skin care preparations are
glycolic acid, salicylic acid, citric acid, and lactic acid. After topical application, alpha hydroxy acids
function by stimulating proliferation of keratinocytes in the epidermis, which leads to enhanced skin turnover.
Treatment with alpha hydroxy acids also improves the condition of collagen and other molecules in the
dermis. The mechanism behind the overall enhanced skin renewal is still not well understood, although
strong clinical evidence demonstrates the efficacy of these materials in rejuvenating skin. In addition, current
evidence suggests that alpha hydroxy acids incite a cascade of cell signaling events involving cytokines
secreted by keratinocytes in the epidermis. The activation of cytokines in skin leads to many important
processes in skin including immune response, wound healing, and accelerated cell turnover.
In regard to maleic anhydride chemistry, skin care compositions containing poly(vinyl ether-maleic
anhydride) and poly(vinyl ether-maleic anhydride-isobutylene) are proposed as possible agents that perform
like alpha hydroxy acids.37,38 One major drawback of alpha hydroxy acids is their high irritation potential.
Treatment with polyacids to minimize negative toxicological effects may prove to be an alternative treatment
modality, although its commercial relevance has yet to be demonstrated by its incorporation into finished
consumer products. Further work to investigate the use of the polymers in conjunction with the alpha
hydroxy acids could prove interesting. Possibly, lower levels of alpha hydroxy acids could be utilized to
achieve similar results when formulated with maleic anhydride-based polymers.
2.6. Incorporation of maleic anhydride derivatives
in sunscreen formulations
Sunscreens are formulations regulated as an over-the-counter (OTC) drug by the Food and Drug
Administration in the United States. In Europe, on the other hand, they are regulated as cosmetics according
to Council Directive 76/768/EEC. Regardless, it is a critical product category for the protection of skin against
harmful ultraviolet rays from the Sun. Exposure to ultraviolet radiation could lead to sunburn reactions
characterized by erythema and edema. It is the culprit of many ailments of the skin including photoaging,
photoimmunosuppression, and photocarcinogenesis. Sunscreen actives are normally characterized as
inorganic scattering agents or organic filters. Inorganic compounds, such titanium dioxide or zinc oxide,
are particulates that reflect or scatter incoming ultraviolet rays, thereby preventing them from reaching the
surface of the skin. On the other hand, organic filters (e.g., benzophenone-4, avobenzone, etc.) absorb the
incoming light. In addition to sunscreen active ingredients, other components of a sunscreen formulation
are equally important. For example, how well the sunscreen film spreads, whether it is waterproof, and if
the formulation is stable, especially at elevated temperatures, are all important considerations when
engineering a new product.
Often, it is desirable to create sunscreen formulations with aesthetically pleasing properties, yielding a
final product that leaves a non-oily, non-tacky film that is not visible and dries quickly. Such sunscreen
products may be formulated using water-soluble maleic anhydride polymeric derivatives. One example is
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a gel based on poly(ethylene-maleic anhydride).39 In this case, the formula is thickened by the polymer and
does not require emulsifiers or surfactants. On the other hand, it is also desirable for the sunscreen formula
to have waterproofing properties allowing the treatment to remain stable during sweating or swimming. It
has been common practice to use a cross-linked terpolymer of methyl vinyl ether, tetradecene, and maleic
anhydride.40 Due to the long aliphatic chain of tetradecene, this polymer is oil soluble, thereby providing
compatibility with organic sunscreens as well as possessing waterproofing properties. More information is
provided for this type of polymer technology in the next section on rheology modifiers.
In addition to serving as formulating agents, maleic anhydride derivatives may also provide performanceboosting properties to sunscreen formulations by other means. For example, inherent problems exist with
some of the commercially available sunscreen agents. Para-aminobenzoic acid is a very polar molecule
making it water-soluble, thereby not allowing it to remain on the skin during perspiration and swimming.
Likewise, avobenzone undergoes keto-enol isomerization leading to instabilities of the molecule and ensuing
reactions that render the sunscreen less efficacious. Providing a more stable environment for the sunscreen
agent can circumvent some of these issues. Maleic anhydride functionalities within a molecule readily
undergo reactions with primary amines, opening the epoxide ring and yielding a half acid, half amide
functionality. Two amine functional aromatic compounds that can be incorporated into a maleic anhydride
functionality are 2-aminobenzoic acid and 2-aminobenzophenone.41 These molecules share similar
properties to their structural counterparts, para-aminobenzoic acid and avobenzone, which are used
universally in sunscreen formulations. At this time, these molecules are not FDA approved sunscreen
compounds; however, they could have possible applications as photostabilizers or SPF boosters.
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3. Rheology modifiers for skin care formulations
Rheology modification is extremely important for skin care. Formulations are often engineered by taking
into account the desired yield stress, sheer thinning behavior, thixotropy, viscosity, and mechanical stability.
Most of these measured parameters apply to the cosmetic composition when it is applied to the skin.
However, equally important is the rheological behavior of a given material when it is dispensed from its
packaging element. There has been much interest in the personal care industry to utilize rheology to
determine the sensorial properties of cosmetic formulations and to predict a product’s stability over long
periods of time and at elevated temperatures.42,43 A class of cross-linked maleic anhydride polymers are
particularly important in this area.44-45 They are used as rheology modifiers for many different types of
personal care formulations including topical wound healing compositions, sunscreens, surfactant-based
systems, nail treatment formulas, and hair styling gels.46-50
In the late 1980s, GAF Chemicals Corporation (later International Specialty Products; currently Ashland,
Inc.) developed a series of polymers based on the poly(methylvinyl ether-maleic anhydride) cross-linked
with 1,9-decadiene (Figure 7). Originally, there were several grades of the polymer available and sold under
the trade names Stabileze 06, Stabileze 12, and Stabileze 15, which were 2.5%, 2%, and 3–3.5% crosslinked, respectively.51 Today, only Stabilize 06 and Stabileze QM are commercially available. The difference
between these two forms of the polymer lies in the particle size of the
commercially available powder. Stabileze QM has a smaller particle size and is
more quickly dispensed in water and converted into a gel.
In the powder form, the polymer exists as an anhydride. In order to thicken
formulations, these polymers must first be hydrolyzed in order to open the
anhydride ring resulting in the diacid form of the molecule. Much effort has gone
into developing processes for hydrolyzing and simultaneously neutralizing these
cross-linked polymers. Hydrolysis can be achieved by three methods: (a)
dispersing the polymer in water at room temperature for 24–48 hours; (b) heating
the polymer in water at 65–80 °C for 30–90 minutes; or (c) heating the polymer
in dilute sodium hydroxide solution at 65 °C for 30 minutes.51-53 High viscosity
gels may be obtained when the polymer is fully neutralized with an organic or
inorganic base, typically in the pH range of 5.5–9, resulting in the expansion/
Figure 7:
Molecular structure
uncoiling of the polymer chains. The broad thickening pH range is afforded due
of poly(methylvinyl
to the two pKa values of the acid groups in the polymer. There have been
ether-maleic
proposals
of replacing the conventional organic and inorganic bases used for
anhydride) cross-linked
neutralization with basic amino acids.54 This mainly stems from concerns that
with 1,9-decadiene.
www.kinetiktech.com
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.kinetiktech.com
info@kinetiktech.com
732-335-5775
(Continued on page 12)
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traditional bases cause irritation. Nevertheless, amino acid neutralization is not a common practice
employed by formulators.
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4. Skin tightening
The modification of the rheological properties of skin by cosmetic treatments is an area of active research
and product development in the personal care industry. Often, the aim is to soften the skin by treatment
with plasticizers, such as glycerol, or by an occlusive effect of hydrophobic materials such as oils and
emollients. As a result, water accumulates in the stratum corneum resulting in plasticization, which ultimately
decreases the modulus of skin, ameliorates the stress between the stratum corneum and underlying skin
layers, and softens lines and wrinkles. Another approach to changing the mechanical behavior of skin is to
induce skin tightness, also referred to as skin firming or lifting. This can be accomplished by washing with
water or with surfactants, which removes low molecular weight materials such as amino acids, urocanic
acid, squalene, cholesterol, and lipids from skin. This results in temporary stiffening of the stratum corneum
and causes the sensation of tightness. Skin tightening can also be produced by surface deposition of certain
film-forming actives, including proteins, polysaccharides, and polymers. This area—skin tightening induced
by treatment with a film-forming polymer—is what we are most interested in for our current discussion.
Quite some time ago, it was reported that ethylene maleic anhydride copolymers were particularly useful
at smoothing the wrinkles of human skin.55 In fact, this patent was well ahead of its time. It was not until the
early 2000s that polymeric skin tightening treatments really began to make any headway in the marketplace.
While a variety of polymeric film-formers could induce a slight skin tightening effect, terpolymers of
poly(isobutylene-alt-maleic anhydride) with dimethylaminopropylamine and methoxy-PEG/PPG
propylamine (INCI: polyimide-1) have been reported to be exceptionally efficacious (see Figure 8 for
molecular structure).56 While the precise mechanism is not fully understood, it is very likely that upon drydown this particular polymer has the ability to act like a shrink-wrap while still maintaining its bioadhesive
strength.57 Therefore, the skin will experience an inward force while still maintaining good adhesion to the
polymer, overall providing a tightening sensation. Often such ingredients are used in finished products for
the temporary effects they produce. For example, many formulas, such as anti-aging and skin whitening,
require that the consumer repeatedly use the products for an extended period of time (e.g., one month or
even longer) in order to induce a quantifiable biological effect in the skin. Often times, the consumer may
quit the regimen if they do not see an immediate effect. Therefore, many skin care finished goods
manufacturers will attempt to include a secondary cue, such as skin tightening or a tingling sensation
produced from menthanol, to maintain the consumer’s interest in repeat use of the product.
Figure 8: Molecular structure of
poly(isobutylene-dimethylaminopropyl
maleimide-ethoxylated
maleimide-maleic acid). It is also
known by its INCI name: polyimide-1.
References
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5. S. Tonge, and B. Tighe, Responsive hydrophobically associating polymers: a review of structure and
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6. US 6,225,485 B1. S. Bertz, F. Miksza, and E. Zucker, High purity adduct of castor oil and maleic
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8. US 8,703,160 B2. S. Harmalker, and K. Ash, Moisturizing compositions. 2014.
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12. D. Moore, S. Orofino, and P. Antonopoulos, Maintaining moisturization from rinse-off products. HAPPI
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16. F. Seniha Güner, Y. Yağcı, and A. Tuncer Erciyes, Polymers from triglyceride oils. Prog Polym Sci 2006,
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17. US 7,361,710 B2. S. Thames, O. Smith, J. Evans, S. Dutta, and L. Chen, Functionalized vegetable oil
derivatives, latex compositions and coatings. 2008.
18. US 2013/0,210,630 A1. O. Musa, K. Narayanan, J. Shih, X. Qu, T. Zhang, and G. Onnembo, Selfemulsifying oil. 2013.
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derivative. 1976.
20. C. Zhong, J. Wu, C. Reinhart-King, and C. Chu, Synthesis, characterization and cytotoxicity of photocrosslinked maleic chitosan-polyethylene glycol diacrylate hybrid hydrogels. Acta Biomaterialia 2010,
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21. US 2006/0,223,945 A1. C. Hollingshurst, D. Price, T. Steckel, B. Filippini, and N. Huang, Low color
polyisobutylene succinic anhydride-derived emulsifiers. 2006.
22. M. Rieger, Skin cleansing products. In Harry's Cosmeticology, Rieger, M., Ed. Chemical Publishing:
New York, 2000.
23. US 4,603,005. J. Chaussee, Cleansing compositions containing alpha olefin/maleic anhydride
terpolymers. 1986.
24. US 4,358,573. C. Verbrugge, Waxy maleic anyhydride alpha olefin terpolymers. 1982.
25. EP 0 182 369 A2. J. Chaussee, Cleansing compositions containing alpha olefin/maleic anhydride
terpolymers. 1985.
26. US 4,265,778. G. Sonenstein, Soap bar. 1981.
27. R. McMullen, Antioxidants and the Skin. Allured Books: Carol Stream, IL, 2013.
28. US 2004/0,047,824 A1. B. Biatry, Oxidation-sensitive hydrophilic active principle containing
composition and use thereof. 2004.
29. K. Kameyama, C. Sakai, S. Kondoh, K. Yonemoto, S. Nishiyama, M. Tagawa, T. Murata, T. Ohnuma, J.
Quigley, A. Dorsky, D. Bucks, and K. Blanock, Inhibitory effect of magnesium l-ascorbyl-2-phosphate
(VC-PMG) on melanogenesis in vitro and in vivo. J Am Acad Dermatol 1996, 34, 29-33.
30. US 2004/0,001,792 A1. B. Biatry, Cosmetic and/or dermatological use of a composition comprising at
least one oxidation-sensitive hydrophilic active principle stabilized by at least one maleic anhydride
copolymer. 2004.
31. US 2004/0,042,990 A1. B. Biatry, Compositon containing oxidation-sensitive hydrophilic active
principle and maleic anhydride copolymer and use thereof. 2004.
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Applications of Maleic Anhydride Chemistry…
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32. US 2004/0,175,342 A1. B. Biatry, Process of making and using composition containing oxidationsensitive hydrophilic active principle and maleic anhydride copolymer. 2004.
33. US 2004/0,052,739 A1. B. Biatry, Cosmetic and/or dermatological use of a composition containing at
least one oxidation-sensitive hydrophilic active principle stabilized by at least one maleic anhydride
copolymer. 2004.
34. US 7,691,903 B2. B. Biatry, Oxidation-sensitive hydrophilic active principle containing composition
and use thereof. 2010.
35. US 7,803,354 B2. B. Biatry, Cosmetic and/or dermatological use of a composition comprising at least
one oxidation-sensitive hydrophilic active principle stabilized by at least one maleic anhydride
copolymer. 2010.
36. M. Carrera, G. Primavera, and E. Berardesca, Alpha hydroxy acids. In Handbook of Cosmetic Science
and Technology, 2nd ed.; Paye, M.; Barel, A.; Maibach, H., Eds. Taylor & Francis: New York, 2006.
37. US 5,736,128. R. Chaudhuri, and D. Bower, Cosmetic composition for rejuvenation of with out skin
irritation. 1998.
38. US 6,312,714 B1. W. Prosise, and K. Plochocka, Cosmetic composition for rejuvenation of skin without
skin irritation. 2001.
39. US 3,821,363. A. Black, and W. Feinstone, Sunscreen preparation employing ethylene-maleic anhydride
copolymers. 1974.
40. US 5,145,669. Y. Kwak, S. Kopolow, M. Helioff, and M. Tazi, Sunscreen composition. 1992.
41. US 8,557,226 B2. O. Musa, and J. Shih, Performance-boosting UV-absorbing compounds. 2013.
42. S. Ozkan, T. Gillece, L. Senak, and D. Moore, Characterization of yield stress and slip behaviour of
skin/hair care gels using steady flow and LAOS measurements and their correlation with sensorial
attributes. Int J Cosmet Sci 2012, 34, 193-201.
43. T. Tadros, Principles of emulsion stabilization with special reference to polymeric surfactants. Int J
Cosmet Sci 2006, 57, 153-169.
44. US 4,952,558. H.-H. Goertz, H.-J. Raubenheimer, and W. Denzinger, Preparation of copolymers of
ethylenically unsaturated dicarboxylic anhydrides and alkyl vinyl ethers. 1990.
45. A. Gripp, M. Helioff, and Y. Kwak, Stabileze PVM/MA decadiene crosspolymers: versatile thickeners
for skin care formulations. Cosmet Toilet Manf Worldwide 1996, 115-118.
46. US 5,744,147. D. Cauwet, and C. Dubief, Cosmetic composition containing at least one surface-active
agent of the alkylpolyglycoside and/or polyglycerolated type and at least one crosslinked copolymer of
maleic anhydride (C1-C5) alkylvinyl ether. 1998.
47. US 2013/0,205,514 A1. J. Evison, and S. Rhowbotham, Depilatory compositions. 2013.
48. US 5,024,779. M. Helioff, M. Tazi, Y. Kwak, and R. Login, Creamy nail polish remover containing
hydrolyzed and neutralized maleic anhydride C1-C4 alkyl vinyl ether copolymer. 1991.
49. US 5,032,391. M. Helioff, M. Tazi, R. Login, and Y. Kwak, Hair styling gel composition. 1991.
50. EP 0,987,019 A1. D. Osborne, Topical antibiotic composition for rapid wound healing. 2000.
51. US 5,254,636. Y. Kwak, and S. Kopolow, Rapid hydrolysis of crosslinked maleic anhydride/lower alkyl
vinyl ether copolymers. 1993.
52. US 5,521,256. Y. Kwak, and S. Kopolow, Process for hydrolyzing and neutralizing a crosslinked polymer
of maleic anhydride and a C1–C5 alkyl vinyl ether, optionally with a hydrophobic monomer,
substantially instantly at room temperature. 1996.
53. US 5,516,828. Y. Kwak, S. Kopolow, and R. Login, Process for the preparation of stable water based stock
solutions of crosslinked lower alkyl vinyl ether and maleic anhydride copolymers and hydrogel product
of the process. 1996.
54. US 4,010,254. C. Koulbanis, A. Zabotto, and J.-C. Contamin, Gels based on vinyl ether-maleic anhydride
copolymer neutralized by a basic amino acid. 1977.
55. US 3,523,998. W. Feinstone, and A. Black, Method of wrinkle smoothing. 1970.
56. J. Jachowicz, R. McMullen, Y. Zolotarsky, and D. Prettypaul, Skin tightening with polymer-containing
formulations. Mechanical skin indentation, photography-image analysis, and panel testing. In Cosmetic
Science Technology, T Four Group: London, 2005; pp 206-215.
57. J. Jachowicz, R. McMullen, and D. Prettypaul, Alteration of skin mechanics by thin polymer films. Skin
Res Technol 2008, 14, 312-319.
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The Safety in Regulatory Framework of
the Cosmetic Industry: Simplified and Practical
September 29, 2015
Location: Seasons, Washington Township, NJ
Organizer and Moderator: Nava Dayan, Ph.D.
Program overview:
T
he Cosmetics and Personal Care Industry has gone through major changes in the past
several decades. Regulators are in the process of a framework establishment to
outline guidance for the protection of the consumer and the environment. There
are three key factors for compliance: ethics, law, and science; combined to establish
a launch to the marketplace. This workshop is put together with the aim of providing
industry professionals with knowledge and basic guidance to this established
framework in safety assessment and to examine the limitations and opportunities.
We believe that new market regulation should not be looked upon as a hindrance
for market entrance, but rather as an opportunity to enter it!
______________________________________________________________
Agenda:
8:00 a.m. – 9:00 a.m.
Registration and breakfast
___________________________________________________________________________________
9:00 a.m. – 10:00 a.m.
Safety assessment approach to comply with the animal testing ban
– Nava Dayan
Key aspect in skin toxicology:
• Skin barrier and innate immunity
• Site of application
• Level of exposure
• Duration of application
• Skin condition
___________________________________________________________________________________
10:00 a.m. – 11:00 a.m.
Legislation for Cosmetic Products in the European Union –
Regulation (EC) 1223/2009
– Annelie Struessmann
Key Aspects of Regulation (EC) 1223/2009
• Area of applicability
• The Regulation’s key goals and regulatory tools
• Roles of responsibility
• Pre-market requirements/in-market control
The Product Information File (PIF) as primary tool for product compliance
• PIF contents
• Establishing and maintenance of the PIF
• Specifics of the Cosmetic Product Safety Report (CPSR)
• PIF function in regulatory compliance processes – benefits from
diligent PIFs
___________________________________________________________________________________
11:00 a.m. – 11:15 a.m.
Break
11:15 a.m. – 12:15 p.m.
North America Regulatory Status – Cosmetic Safety
– Wen Schroeder
• Market, consumers, and trendsetting milestones
• Cosmetic safety in North America (U.S., Canada, Mexico)
• Regulatory definition and requirements
• What, who, why, when, and how?
• Self-regulatory framework
• Compliance tools and strategy
(Continued on page 16
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The Safety in Regulatory Framwork of the Cosmetic Industry…(Continued from page 15)
12:15 p.m. – 1:15 p.m.
Lunch break
___________________________________________________________________________________
1:15 p.m. – 2:00 p.m.
Key endpoint in testing
– Nava Dayan
• Skin irritation and sensitization
• Photo-toxicity
• Skin absorption
___________________________________________________________________________________
2:00 p.m. – 2:45 p.m.
Status on Implementation of Regulation (EC) 1223/2009
and Impact on Innovation
– Annelie Struessmann
• After the Regulation’s implementation deadline of July 2013
• Open issues
• Solo activities by Member States
• Future deadlines built into the regulatory text
• Further future regulatory activities to be expected
• Working with the Cosmetics Product Regulation
• The Animal Testing Ban’s impact on product innovation
• Overall judgment of the new regulatory framework
___________________________________________________________________________________
2:45 p.m. – 3:00 p.m.
Break
3:00 p.m. – 3:45 p.m.
Asian Cosmetic Regulatory Status – Cosmetic Safety
– Wen Schroeder
• Market, consumers, and trendsetting milestones
• Cosmetic safety in Asia (key regional representative countries)
• Regulatory definition and requirements
• What, who, why, when, and how?
• Self-regulatory framework
• Compliance tools and strategy
___________________________________________________________________________________
___________________________________________________________________________________
3:45 p.m. – 4:30 p.m.
Panel discussion – questions and answers
Educators’ Biographies
Nava Dayan, Ph.D.
Nava Dayan is the owner of Dr. Nava Dayan L.L.C, a skin science and
research consultancy serving the pharmaceutical, cosmetic, and personal care
industries; dermal and transdermal. Dr. Dayan offers consulting for product
feasibility in skin care, composition of R&D plans covering efficacy and
toxicology; planning, execution, and data interpretation into claims of experiments
during the processes of drug discovery as well as formulations, delivery for
improved efficacy and attenuated toxicity. Sample of expertise includes: drug-skin
interaction, bio-markers (genomics and proteomics), skin/age related sensitivities,
inflammatory skin disorders, innate immunity, and biota. She also conducts
customized education classes. Dr. Dayan has 25 years of experience in the skin
care segment, and has more than 150 publication credits in numerous industryrespected journals and in four books. She has been awarded the In-Cosmetics
Gold Award for innovation and commensurate recognition from the NYSCC and
the CRS for excellence.
Annelie Struessmann, Ph.D.
Dr. Annelie Struessmann is Technical Regulatory Director with CONUSBAT,
a provider of internationalization regulatory services for the Fine Chemicals,
Cosmetics, and Toiletries industries: www.conusbat.com. She joined the firm in
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2003, and, based on many years of experience gained while working in the international cosmetics and
ingredients industry, she established the service area for regulatory affairs, which became the core area for
CONUSBAT. Focusing on the European regulatory frameworks for cosmetic products and for chemicals
(REACH), she provides clients with compliance strategies, safety assessments, registrations, notifications,
direct representations, etc. With a worldwide network of partners, the compliance services are expanded to
a global scale. Dr. Struessmann publishes with various recognized journals in her area of expertise and
provides workshops on a worldwide scale, as well as e-trainings. Before joining CONUSBAT she worked in
various managerial functions at international locations of global companies, such as IFF, Akzo Nobel, Rewo
(now Evonik), and DHW GmbH. Her educational background includes a Master’s Degree in Chemistry and
a B.S. in Food Chemistry from the Technical University, RWTH, Aachen, Germany. Additionally, she received
a Doctorate in Biopolymer Chemistry from the German Wool Research Institute (DWI) in Aachen, working
on projects for Schwarzkopf (Germany) and Clairol (Stamford, CT, U.S.). From Clairol she was awarded the
Company’s prestigious Gelb Foundation Fellowship.
Making Personal
Personal Car
Caree Beautiful®
Specialty Silicones & Actives
Skin Car
Caree
Caree
Hair Car
Color Cosmetics
®
www.biosiltech.com
Wen Schroeder
Wen Schroeder is the founder and president of SEKI Cosmeticals. She is key
expert for the ASEAN-EU Program for Regional Integration Support in cosmetic
and pharmaceutical GMP and testing. Ms. Schroeder is scientific advisor to Taiwan
External Trade Development Council and served for the Personal Care Products
Council. She is active in the Society of Cosmetic Chemists and the Regulatory
Affairs Professional Society. With 20+ years of industrial experience, 30 U.S.
patents, and numerous publications, Ms. Schroeder is an internationally recognized
lecturer on cosmetic science and regulatory affairs. Her lecture topics cover a wide
range of areas including chemical management and biocide regulations to food,
drug, and cosmetic law. Ms. Schroeder is the editor of the recently released book, Sustainable Cosmetic
Product Development, published by Allured Books, which is the first comprehensive technical reference
work in this field for the personal care industry.
DWI Leibniz-Institut für Interaktive Materialien
HairS’15
19th International Hair Science Syposium
Trier, Germany
September 2-4, 2015
Symposium Fee
Early bird fees for registration and payment by August 1, 2015 are:
• 770€ for participants
• 590€ for DWI member companies
• 330€ for speakers (one presenting author per oral presentation,
no reduction for poster authors)
Fee includes meals, coffee breaks, excursion,
conference dinner, book of abstracts, and conference proceedings.
For more info: www.dwi.rwth-aachen.de.
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Inspire
E
T
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Imagine
P
E
Innovate
The US Society of Cosmetic Chemists hosts the 29th IFSCC Congress
O
NE
WF
RONTIERS
OND DREAM
SI
NT
October 23-26, 2016
Lake Buena Vista, Florida
BEY
Walt Disney World Dolphin Resort
29TH CONGRESS
O R L A N D O, F L 2 016
I N S PIRE I MAGINE INNOVATE
Beyond Dreams into New Frontiers: Inspire, Imagine, Innovate
Make note of it…
Send news of interest, guest editorials, and comments to
Roger McMullen, Editor • E-mail: roger_mcmullen@fdu.edu
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22nd Annual
NYSCC Golf Outing!
Wednesday, July 29th
• Registration 11:00 a.m-12:30 p.m. • Shotgun Start 1:00 p.m.
SILAB creates and
manufactures unique,
consistently safe, natural
active ingredients with
proven efficacy.
You need more information about our
products?
Please contact our subsidiary SILAB Inc.:
email: silabinc@silabinc.com
phone: 732-335-1030
engineering natural active ingredients
Crystal Springs Resort
1 Wild Turkey Way, Hamburg, NJ 07419
Course Phone: (855) 977-6473
Registe!r
Early
Golf 180
$
per person.
Limited
Space!
Includes: Box lunch, 18 holes of golf
with cart, cocktail reception and dinner
…plus door and skill prizes and gifts.
The outing is open on a first come first serve basis (the course has a limit).
You do not have to be an SCC member to play. Foursome reservations
are now being accepted (but a foursome is not required).
Non-refundable payments must be received by July 15th.
The best and easiest way to register and make payment is using a
credit card online at www.nyscc.org. Otherwise, please use the
registration form below and checks should be made be payable to NYSCC.
For information on the golf outing contact Hamel Dave at (973) 727-9916.
22nd Annual NYSCC Golf Outing!
Payment enclosed ($180.00 per player) n Yes n No
Please complete this form and send it along with checks payable to NYSCC c/o:
Hamel Dave, SummitReheis, 40 Baldwin Road, Parsippany, NJ 07054
Name(s) ______________________________________________________________________________________________________________________________________________________________________________________________________________________________________
E-mail Address _________________________________________________________________________________________ Phone # _______________________________________________________________________________________________________
Company ___________________________________________________________________________________________________________________________________________________________________________________________________________________________________
GOLF: Name #1 _____________________________________________________________________________________ Name #1 _____________________________________________________________________________________________________
Name #2 _____________________________________________________________________________________ Name #2 _____________________________________________________________________________________________________
Name #3 _____________________________________________________________________________________ Name #3 _____________________________________________________________________________________________________
Name #4 _____________________________________________________________________________________ Name #4 _____________________________________________________________________________________________________
NOTE: A foursome is not required as we will combine groups if needed.
Please be sure to indicate your e-mail address if you would like to receive confirmation of your registration.
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Upcoming 2015 NYSCC Events Calendar
• For updated NYSCC information, visit us on the web at: www.nyscc.org
• For National SCC information: www.scconline.org
June 10
NYSCC Monthly Meeting, Green Chemistry, Aqua Azul Yacht, Weehawken, NJ
July 29
NYSCC Golf Outing, Crystal Springs Resort, Hamburg, NJ
September 18
Culinary Event, Midtown Loft, New York, NY
September 29
Safety and Regulatory Workshop, Seasons, Washington Township, NJ
October 24
November 11-12
November TBD
December 10
NYSCC 60th Anniversary Party, Glennpointe Marriott, Teaneck NJ
NYSCC Color Cosmetics Symposium, Location TBD
NYSCC Board Transition Meeting
NYSCC Social Media Holiday Party, New York, NY
Employment Opportunities
For complete ads please go to the NYSCC website: https://nyscc.org/employment/employment-listings/
n Product Development Manager
StriVectin
United States
n Quality Control Supervisor/Manager
Kobo Products, Inc.
South Plainfield, NJ
n Applications Engineering &
Technical Support Scientist
BioAmber, Inc.
United States
20
n Account Manager – Northeast
Presperse Corporation
Home Office (one day a week in Somerset, NJ)
n Director – Sales
Presperse Corporation
Somerset, NJ
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