Jun 02, 2015
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SUMMARY
� Similar structure as the polar group of phospholipid in human cell membrane
o Epidure-MF and CF contain polymers obtained from 2-methacryloyloxyethyl phosphorylcholine (MPC). MPC
polymers are applied to coating agent for medical devices, moisturizer for cosmetics, contact lenses and soaking
solution for contact lenses. We are now supplying new biocompatible and hydrophilic skincare agents for fibers,
fabrics and textiles.
� Hydrogel formation
o MPC polymers form hydrogels contacting with water on fibers surface.
o The hydrogels has high hygroscopicity and durability against home laundry.
� Skin protection, antistatic
o The textiles modified by Epidure-MF and CF protects any skin from any irritants.
o The textiles support the self-healing ability repairing damaged skin.
o Epidure-MF and CF work also as an antistatic agent and an SR agent.
� Safety
o Epidure-MF and CF are formed with safety compounds. They have no skin irritation.
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PROPERTIES OF EPIDURE-MF AND CF
� Epidure-MF3
o Properties: mild anionic
o Effect: skin protection, soil release, antistatic, hygroscopic, water absorbing
o For PET or T/C
� Epidure-MF5
o Properties: mild anionic
o Effect: skin protection, soil release, antistatic, hygroscopic, water absorbing
o For PET
� Epidure-CF72
o Properties: mild cationic
o Effect: skin protection, antistatic, hygroscopic, water absorbing
o For Nylon or Cotton
*Each product contains 10-25% ethanol to prevent the gel formation.
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EPIDURE (MPC)
EPIDURE is a water-soluble polymer derived from 2-methacryloyloxy ethyl phosphorylcholine (MPC). MPC is a compound, which has the similar structure as the polar group of phospholipid in cell membrance. Various materials can be obtained with using MPC.
MPC polymer can be useful for artificial organs with forming cell membrane-like structure on the surface. Blood coagulation test of MPC polymer :
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PROPERTIES OF EPIDURE-MF AND CF BASED ON HYDROGEL
� Problem of existing hydrophilic agents o Less Hydrophilicity o Less Softness o Less Durability against home laundry
MPC Polymers forms hydrogel on fibers.
Hydrogel
High water
content
Neutral
Soft
Antistatic
Hydrogel Layer
Fiber
� Fabrics with Epidure o Hydrophilicity o Durability o Softness o Hygroscopicity o Antistaticity o Soil guard
property o Safety
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Textile: T/C Agent: Epidure -MF3
Conc. of agent: 5% Method
Soak textile in the dilution ↓ Pick-up: 80% ↓
Drying(100℃, 2min) ↓
Curing(150℃, 3min) Surface analysis of textile
X-ray photoelectron Spectroscopy
ESCA3300、SHIMAZU P/C value
DURABILITY OF EPIDURE ON T/C AGAINST HOME LAUNDRY
Epidure-MF has good durability against home laundry.
T/C(65/35) modified by Epidure-MF3
C1s Spectrum P2p Spectrum
390395400405410
After 30 HL
Initial
None-
modified
280285 290295 300
After 30 HL
Initial
None-
modified
Binding Energy / eV Binding Energy / eV
P/C value:
Initial 1.79×10-2
After 30 HL 1.51×10-2
Eighty% of initial
Epidure has
remained after 30 HL
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CYTOTOXICITY TEST FOR EPIDURE
Cytotoxicity test (Neutral red assay) Subjects were added to SIRC cells from cornea of rabbit. The neutral red solution was added to the cells after incubation. The cell living rate was calculated from the data of UV absorption spectrum.
Epidure-MF and CF have high biological safety.
0204060
80
100
120
0.0001 0.001 0.01 0.1 1 10 100Concentration (%)
Cel
l li
vin
g r
ate (
%)
Epidure-MF3
Epidure-MF5
Epidure-
Ethano
Detergen
Shampoo
SDS (surfactant)
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SKIN IRRITATION TESTS FOR EPIDURE
Patch test using human of Epidure-MF and CF: � Test methods (This tests were done by dermatologist.)
� Subjects: Age:19 to 61, Male and Female, Members: 43~45
� Test sample and amount: undiluted Epidure, 0.01g
� Patch test: A fin chamber having 0.01g of sample was put on the upper parts of their arms for 24 hours.
� After 24 hours, the chamber was removed. Then the skin surface was observed by naked eyes one hour and 24 hours later.
� Evaluation: ICDRG standards
2. Results: All of Epidure were negative in this tests.
Epidure-MF and CF have no irritation to human skin.
MF3 MF5 CF72
1hr 24hr 1hr 24hr 1hr 24hr
Negative - No reaction 44 45 43 43 43 43 ± Only redness 1 0 0 0 0 0 Positive + Redness, Infiltration, Small rash 0 0 0 0 0 0 ++ Redness, Infiltration, Rash, Blister 0 0 0 0 0 0 +++ Big blister 0 0 0 0 0 0
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SKIN PROTECTION BY EPIDURE-MF
Inhibition of skin irritation based on SDS by Epidure-MF3
Methods:
Following test solutions were put on the skin of hairless mice twice a day. After five days, the skin was observed and the
condition was scored.
Test Solution I : 1% Epidure-MF3Test Solution II : 7.5% SDS aqueous solution and 1% Epidure-MF3
Test Solution III : 7.5% SDS aqueous solution Results: No skin irritation was observed on Test Solution I. The skin irritation
of Test Solution II was less than that of Test Solution III.
*SDS means sodium dodecyl sulfate.
Epidure-MF inhibits skin irritation based on SDS
MF3 SDS+MF3 SDS
Sk
in I
rrit
atio
n
Sco
re
00.511.522.5 Skin Irritation Score after 5 days
Ⅰ Ⅱ Ⅲ
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SKIN PROTECTION
The textile modified by Epidure protects human skin from irritants.
0
10
20
30
40
50
60
70
80
90
0.10.10.10.1% SDSSDSSDSSDS 0.3% SSSSDSDSDSDS 0.5SDSSDSSDSSDS 0.1%SDSSDSSDSSDS 0.3%SDSSDSSDSSDS 0.5%SDSSDSSDSSDS
;;;;1 hour later1 hour later1 hour later1 hour later;;;;24 hours 24 hours 24 hours 24 hours
No irritation
Irritation Textile and Test method Textile: Cotton 100% and Cotton modified by 5% of Epidure-MF3 Irritant: Sodium dodecyl sulfate (SDS) ① Textiles (6 mmφ) were put in the test ②Ten micro litters of 0.1~0.5% aqueous SDS solution were dropped on the textiles. The textiles were applied on the back of human (5 members). ③ After 24 hours the textiles were taken off the back,
The redness was measured by naked eye one hour and 24 hours later.
Evaluation: Redness was scored based on Japanese skin irritation evaluation. ★Irritation index=total score/number of patients×100 Results In the cases of any concentration of SDS, textiles modified by Epidure show smaller irritation index than control textiles. The textile modified by Epidure protects human skin from irritants.
Control Textile modified by MF3
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RECOVERY OF ROUGH SKIN BY WEARING OF FABRICS TREATED WITH
EPIDURE
Fabrics treated with Epidure support natural healing of rough skin. 0.00.00.00.010.010.010.010.020.020.020.020.030.030.030.030.040.040.040.040.050.050.050.050.060.060.060.060.070.070.070.070.0
0000 1111 2222 3333 4444 Wearing Time / Day
T
E
W
L
In
de
x
:::: Non treatmentNon treatmentNon treatmentNon treatment:::: SqualaneSqualaneSqualaneSqualane:::: EpidureEpidureEpidureEpidure----CF72CF72CF72CF72
Normal
100
0.00.00.00.05.05.05.05.010.010.010.010.015.015.015.015.020.020.020.020.025.025.025.025.030.030.030.030.0
0000 1111 2222 3333 4444
WCKL Index
:::: SqualaneSqualaneSqualaneSqualane :::: EpidureEpidureEpidureEpidure----CF72CF72CF72CF72
Normal
100
Damaged
Improvement of TEWL Index Improvement of WCKL Index
Wearing Time / Day
Recovered
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SUPPRESSING ROUGH SKIN FORMATION
The experimental rough skin formation and suppression test was performed using the cultured keratinocyte. Applying a sodium dodecyl sulfate solution (SDS) for 24h caused Inflammation of IL-1 α such as rough skin, however these phenomena were prevented by applying EPIDURE simultaneously.
SDS : 30µµµµ g/l
0
200
400
600
800
1000
1200
1400
1600
SDS SDS+0.1% Epidure SDS+0.5% Epidure 0.5% Epidure
IL -
1αα αα
(p
g/m
l)
Cultured keratinocyte add SDS and
(NHEK) Medium change Epidure
Measurement of
Extra IL - 1α
48 h 24 h 24h
Inflammation
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PROTECTION THE SURFACE OF CUTICLE FROM DAMAGE
When shampooed hair was tied up, the surface of the cuticle was lifted. On the other hand, the surface of the cuticle whose hair was applied with EPIDURE was not lifted up. EPIDURE is effective for protecting hair, with developing smoothness.
(A) After shampoo (B) Applying Epidure after shampoo
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PREVENTION OF THE CUTICLE SURFACE FROM DAMAGE
Hair damaged by 10 times of bleaching and EPIDURE-C treated hair, which was prepared by soaking the damaged hair in 1% EPIDURE solution, were observed under SEM (Photographs 1 and 2). Lifting up of cuticle was prevented effectively by EPIDURE-C .
Picture 1. Damaged Hair
Picture 2. EPIDURE-C treated Hair
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WATER RETENTION CAPABILITY
Though EPIDURE has a high hygroscopicity and moisture retention capability, the biggest difference compared with
Hyaluronic acid is that the hygroscopicity and moisture retention capability are retained even after rinsing with water.
0
0.5
1
1.5
2
2.5
Wa
ter
ho
ldin
g c
ap
ac
ity
(re
lati
ve
va
lue
)
Hyaluronic acid Epidure
After washing
1 hour after washing with water
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SUSTAINABILITY
EPIDURE is not easily removed from the surface of the skin. This was demonstrated that coating of EPIDURE labeled by fluorescence to the skin equivalent remained even 3 hours after rinsing with large amounts of PBS solution.
EPIDURE has been proven for safe with conducting following tests.
1. Acute toxicity test 2. Continuous skin irritation test 3. Phototoxicity test 4. Acute eye irritation test 5. Human patch test 6. Skin primary irritation test 7. Maximization sensitization test 8. Skin photosensitization test 9. Mutagenicity test
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EPIDURE-HM, PMB: Homopolymer made from MPC monomer. NOF has two types of 40% and 5% aqueous solution (EPIDURE-HM-500). INCI Name: F Polyphosphorylcholine Glycol Acrylate
EPIDURE-HM-500: Copolymer made from MPC and butylmethacrylate of hydrophobic monomer; 5% aqueous solution INCI Name: F Polyquaternium-51
Chemical structure of EPIDURE-HM,HM-500
Chemical structure of EPIDURE-PMB
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QUALITY STANDARD
Items
Standard
Testing method EPIDURE-HM
EPIDURE-PMB
Properties Colorless liquid, scentless or a slight peculiar odor
Visual observation
Residue on drying
43-48% 4-6% General testing method for JSCI
pH 4 -6 General testing method for JSCI
Viscosity *500�`3000cps **6�`60cst
General testing method for JSCI *: the 2nd method, **: the 1st method
Heavy metals
20ppm or less General testing method for JSCI, the 2nd method, 1g
As 2ppm or less General testing method for JSCI, the 3rd method, apparatus B, 1g
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EPIDURE-A,C We introduce " EPIDURE-A " and " EPIDURE-C ", which are new products of the EPIDURE series and were developed for hair-care products. New EPIDURE can restore damaged hair (damage caused by repetitive bleaching etc.) into healthy hair by adhering to the hair fibers and moisturizing the hair since the EPIDURE polymers contain all cationic, anionic and hydrophobic monomers as shown in Figure 1.
EIPIDURE-A
EIPIDURE-C
Figure 1. Chemical structures of EPIDURE-A and EPIDURE-C
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FRICTION COEFFICIENT OF HAIR
Friction coefficients were measured using a friction tester KSE-SE (Kato Tech Co,ltd.) for healthy hair, hair damaged by 10 times of bleaching,
and EPIDURE-A and -C treated hair, which was prepared by soaking the damaged hair in 1% solution of EPIDUREA or C (Figure 2). From the
resultant friction coefficients, which show the smoothness of hair, EPIDURE-A and -C treatment was found to improve the smoothness up to
that of the healthy hair.
Friction coefficient of hair
2.7
2.75
2.8
2.85
2.9
2.95
3
3.05
Healthy hair Damaged hair Epidure-A Epidure-C
MIU
Figure 2. Friction coefficient of Hair
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TENSILE PROPERTY OF HAIR
Tensile strength test of the test samples was conducted using the same treatment methods as in the friction test (Figure 3). The strength of damaged hair was recovered by EPIDURE-A and -C treatment
Tensile property of hair
0
20
40
60
80
100
120
140
Healthy hair Damaged hair Epidure-A Epidure-C
Ten
sile s
tren
gth
/gf
Figure 3. Tensile Property of Hair
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ANTISTATIC EFFECT OF HAIR
For healthy hair, hair damaged by 10 times of bleaching, and EPIDURE-A treated hair, which was prepared by soaking the damaged hair in 1% EPIDURE solution, the static charges of the hair specimens were measured using SIMCO electrostatic field meter after rubbing the specimens with PET film for 30 times; and we monitored decreases in static charge in the course of time. (Figure 4) EPIDURE-A treatment reduced the static charge of the hair, thus it is expected to prevent static flyaway of the hair.
Antistatic effect of hair
0
0.5
1
1.5
2
2.5
3
3.5
4
4.5
0 10 20 30 40 50 60 70 80 90
Time/sec
sta
tic c
harg
e /kv
Healthy hair
Damaged hair
Epidure-A
Figure 4. Antistatic effect of Hair
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PRODUCTS
EPIDURE-A Copolymer made from MPC, sodium methacrylate (anionic monomer) and butyl methacrylate; 5% aqueous solution. INCI name: polyquaternium-65
EPIDURE-C Copolymer made form MPC and -2-hydroxv-3-methacryloyloxypropyltrimethylammnonium chloride (cationic monomer) ; 5% aqueous solution. INCI name: polyquaternium-64
EPIDURE-NR-NA NOF Corporation started the sales of “EPIDURE-NR” and “EPIDURE-NA”, which have new functions and concepts. Produced using EPIDURE-S (Fig.1) as the main ingredient, EPIDURE-NR is a solution of polymers in multivalent alcohol. EPIDURE-NA is dispersion of nano-particles of polymer (Ave. particle size: 50nm) in water.
Figure 1.
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“EPIDURE-NR” and “EPIDURE-NA” have unique characteristics. They form nano scale lamella structures on an applied surface when they dry.
Lamella phase formation
Figure 2
Dispersion of Epidure-NR or
Epidure-NA
Skin, hair
treatmen
t
dry
ing
Skin, hair
25
TRANSMISSION ELECTRON MICROSCOPIC OBSERVATION OF A CASTING FILM OF EPIDURE-NA SHOWS FORMATION OF LAMELLA STRUCTURE.
Figure 3.
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The new products are effective cosmetic ingredients for skin care and hair care. They restore and protect healthy skin and hair.
EPIDURE-NR
5% EPIDURE-S solution in multivalent alcohol, which is a mixture of Butylene Glycol and Glycerin INCI names: Glycerin, Butylene Glycol, and Polyquaternium-61 Characteristics EPIDURE-NR: Encloses and reserves active components stably, Forms lamella structure on the skin surface and protects the skin, and Increases the penetration efficiency of active components. (Demonstration of Reserving effect) EPIDURE-NR can enclose oily active components such as Vitamins. The enclosed ingredients were confirmed to remain on
the hair surface. Here, the model material used as an active component was florescent oil. Fluorescence was incorporated in
EPIDURE-NR. Observations under a fluorescent microscope of damaged hair that was immersed into the EPIDURE-NR
showed fluorescence.
Inclusion of the fluorescent probe (active components) into EPIDURE-NR. It dissolves into water by mixing for 30 min at 50
to 60°C. While stirring water of 50 to 60°C, just add EPIDURE-NR to which fluorescence is included. With this simple
method, nano particles are formed. There is no need to use ultra high-presser homogenizer (ex. microfluidizer).
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Mix 30 mins at Mix 10 mins Fluorescent probe at 50-60ºC at 50-60ºC
1. Add Fluorescent probe 2. While stirring water of 50-60ºC 3. Inclusion of fluorescence with to to Epidure-NR add Epidure-NR with in Epidure-NR
fluorescence included
Figure 4
Fluorescence Epidure-NR with
fluorescence included
Epidure-NR
Water
Water
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Microscopic photographs of: 1) non-treated damaged hair, 2) fluorescence dissolving in water from surfactant-treated hair, and 3) inclusion of fluorescence in EPIDURE-NR treated hair.
1. Immerse hair on Epidure-NA 2. Rinse off with water 4. Observation under a microscope
3. Dry up
100 gm 100 gm 100 gm
Figure 5.
Epidure-NA with fluorescent probe
Non-treated Treated with fluorescent
probe only
Treated with Epidure-NR and
fluorescent probe
Epidure-NR with active components remains on hair even after rinsing with water
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Only EPIDURE-NR treated hair showed strong fluorescence. This shows that EPIDURE-NR with active components remained on the hair even after the hair was rinsed with water. This is likely because the active component in EPIDURE-NR was included in the newly formed lamella structure on the hair.
2.EPIDURE-NA 1% EPIDURE-S water dispersion. EPIDURE-S is added to 9.5% Glycerin, 9.5% Butylene Glycol and 0.25% PCA Ethyl Cocoylarginate, which is a preservative. INCI names: Water, Glycerin, Butylene Glycol, Polyquaternium-61 and PCA Ethyl Cocoylarginate
(Characteristics) EPIDURE-NA Repairs damaged hair by forming lamella structure on the hair, Makes the hair antistatic, and Protects the hair from discoloring.
(Demonstration of the repair efficacy of damaged hair) We observed the wetting effect under a high power microscope. A drop of water on the surface of a healthy hair fiber Damaged hair by bleaching Damaged hair that was treated with hair care ingredient solutions (active conc. 0.05%)
Epidure-NA treated
hair
Figure 6.
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Damaged hair showed decreases in contact angle with water from that of healthy hair. Because the lipid phase at the outermost surface on the hair fiber was damaged, the hair surface became hydrophilic. On the other hand, EPIDURE-NA treated hair showed high repellency similar to that of healthy hair. EPIDURE-NA restored the hair fiber to be hydrophobic again by forming a lamella structure on the hair. The damaged hair was restored into healthy hair.
3.Safety
Safety of EPIDURE(R)-NR and EPIDURE(R)-NA
Item Result
EPIDURE-NR EPIDURE-NA
Acute oral toxicity test >2000mg/kg >2000mg/kg
Skin primary irritation test Non-irritation Non-irritation
Human patch test negative negative
Table 1.
Item Result
Acute oral toxicity test >2000mg/kg
Mutagenicity test negative
Skin primary irritation test Non-irritation
Continuous skin irritation test Non-irritation
ocular irritation testing Very slight
Skin sensitization testing Non-sensitization
Human patch test negative
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METHODS FOR USE
1111. Contents and Storage
Contents: 16 kg
Storage: Store in a dark and cool place.
2222. Caution for use
Check compatibility with other agents before using Epidure.
Do the laboratory test before using Epidure in the factory.
3333. Examples of use
Padding (MF3、MF5) Epidure conc.: 3-10%
Pick –up: 70-100%
Drying: 100℃, 2 min.
Setting: more than 140℃, 2 min.
Soaking (CF72) Epidure conc.: 3-10%owf
Temp: 30-40℃
pH control: 4-7
Anionic water-soluble PET finishing agents in
addition give the textile softness and durability.