METHOD FOR TREATING KERATIN MATERIALS USING AN ACRYLIC ANHYDRIDE POLYMER IN OILY DISPERSION AND AN AMINE COMPOUND

Abstract

The present invention relates to a process for treating keratin materials, preferably human skin, in particular the lips, preferably in at least two steps involving, in a first stage, the application to said materials of an oily dispersion (A) comprising i) particles of copolymers of alkyl acrylates and of anhydride acrylics, ii) stabilizers, iii) one or more hydrocarbon-based oils; and then, in a second stage, the application to said materials of a composition (B) comprising iv) one or more amine compounds, it being understood that the process of the invention uses v) one or more cosmetic active agents chosen from a) pigments, b) active agents for caring for the skin, and c) UV-screening agents and also d) mixtures thereof; ingredients a) to d) possibly being found in composition (A), and/or in composition (B), and/or in another composition (C).

The process of the invention makes it possible to obtain a treatment of said keratin materials that is notably resistant to sweat, to shower gels, to water and to fatty substances, in particular plant or animal food oils, and more particularly plant oils such as olive oil, sunflower oil, walnut oil, hazelnut oil, etc.

The keratin material treatment process of the present patent application is also suitable for making up the skin or the lips, such as foundations and lipsticks.

Claims

1. A process for treating keratin materials comprising: 1) the application to said materials of an oily dispersion (A) comprising: i) one or more particles consisting of one or more ethylenic copolymers: a) of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and b) of ethylenically unsaturated anhydride compound; and ii) one or more stabilizers consisting of ethylenic polymers chosen from: c) polymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate monomers; and d) copolymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate and (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and iii) one or more hydrocarbon-based oils; 2) the application to said materials of a composition (B) comprising: iv) one or more amine compound(s) chosen from: e) polyamine compounds bearing several primary amine and/or secondary amine groups, and f) amino alkoxysilanes, it being understood that: the process uses v) one or more cosmetic active agents chosen from a) pigments, b) active agents for caring for keratin materials and c) UV-screening agents, and also d) mixtures thereof, ingredients a) to d) possibly being found in composition (A), and/or in composition (B), and/or in another composition (C); and compositions (A), (B) and (C) may be applied together or separately.

2. A process for treating keratin materials according to claim 1, comprising: 1) the application to said materials of an oily dispersion (A), comprising: i) one or more particles consisting of one or more ethylenic copolymers: a) of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and b) of ethylenically unsaturated anhydride compound; and ii) one or more stabilizers consisting of ethylenic polymers chosen from: c) polymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate monomers; and d) copolymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate and (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and iii) one or more hydrocarbon-based oil(s).

3. The process as claimed in claim 1 in which the oily dispersion (A) comprises one or more particles constituted of one or more ethylenic copolymers a) of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate, of formula H.sub.2C=C(R)—C(O)—O—R′, with R representing a hydrogen atom or a (C.sub.1-C.sub.4)alkyl group, and R.sup.1 representing a linear or branched (C.sub.1-C.sub.4)alkyl.

4. The process as claimed in claim 1, in which the oily dispersion (A) comprises one or more particles constituted of one or more ethylenic copolymers of b) ethylenically unsaturated anhydride compound b) chosen from derivatives of maleic anhydride (Ib) and of itaconic anhydride (IIb): ##STR00013## in which formulae (Ib) and (IIb) R.sub.a, R.sub.b and R.sub.c, which may be identical or different, represent a hydrogen atom or a (C.sub.1-C.sub.4)alkyl group.

5. The process as claimed in claim 1, in which the polymer(s) of the particles i) of dispersion (A) comprise, or consist essentially of, from 80% to 99.99% by weight of ingredient a) relative to the total weight of the polymer(s) and from 0.01% to 20% by weight of ingredient b), relative to the total weight of the polymer.

6. The process as claimed in claim 1, in which the copolymer(s) of the particles i) consist of polymers a) and b) with an a)/b) weight ratio inclusively between 5.5 and 20.

7. The process as claimed in claim 1, in which the polymer of the particles i) is present in dispersion (A) in an amount ranging from 20% to 60% by weight relative to the total weight of dispersion (A).

8. The process as claimed in claim 1, in which the stabilizer(s) ii) of dispersion (A) are constituted of ethylenic polymers chosen from: c) polymers of monomers of formula H.sub.2C=C(R)—C(O)—O—R″ with R representing a hydrogen atom or (C.sub.1-C.sub.4)alkyl group, and R″ representing a (C.sub.5-C.sub.10)cycloalkyl group; and d) copolymers of H.sub.2C=C(R)—C(O)—O—R′ and of H.sub.2C=C(R)—C(O)—O—R″ with R, R′ and R″ as defined previously.

9. The process as claimed in claim 1, in which the sum of i) the particle(s)+ii) stabilizer(s) present in dispersion (A) comprises from 10% to 50% by weight of copolymers d and from 50% to 90% by weight of polymer c) relative to the total weight of the sum of i) stabilizer(s) and ii) of polymer particle(s).

10. The process as claimed in claim 1, in which the hydrocarbon-based oil(s) iii) of dispersion (A) are apolar, i.e. formed solely of carbon and hydrogen atoms.

11. The process as claimed in claim 1, in which dispersion (A) is in inverse emulsion, i.e. of water-in-oil (W/O) type, and comprises one or more surfactants.

12. The process as claimed in claim 1, in which the amine compound(s) of composition (B) are chosen from the amino alkoxysilanes f).

13. The process as claimed in claim 1, in which the a compound(s) of composition (B) are chosen from e) polyamine compounds bearing several primary amine and/or secondary amine groups ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022##

14. The process as claimed in claim 1, in which composition (B) comprises one or more hydrocarbon-based oil(s) iii).

15. The process as claimed in claim 1, in which composition (B) is aqueous.

16. The process as claimed in claim 1, in which composition (B) is anhydrous.

17. The process as claimed in claim 1, in which v) the cosmetic agent(s) are chosen from pigments.

18. The process as claimed in claim 1, in which v) the cosmetic agent(s) are in dispersion (A).

19. The process as claimed in claim 1, in which v) the cosmetic active agent(s) are in composition (B).

20. The process as claimed in claim 1, which uses one or more plasticizers vi), which are present in composition (A), and/or in composition (B), and/or in another composition (C).

21. The process as claimed in claim 1, comprising: 1) the application to said materials of an oily dispersion (A); followed by 2) the application to said materials of a composition (C) comprising v) one or more cosmetic active agents, preferably pigments; followed by 3) the application to said materials of a composition (B).

22. The process as claimed in claim 1, comprising: 1) the application to said materials of a composition (C) comprising v) one or more cosmetic active agents; followed by 2) the application to said materials of an oily dispersion (A); followed by 3) the application to said materials of a composition (B).

23. The process as claimed in claim 1, in which, between step 1) and step 2), there is no rinsing, and the keratin materials are dried naturally before applying composition (B).

24. A kit or device with several separate compartments, comprising: in a first compartment: an oily dispersion (A) comprising: i) one or more particles consisting of one or more ethylenic copolymers: a) of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and b) of ethylenically unsaturated anhydride compound; and ii) one or more stabilizers consisting of ethylenic polymers chosen from: c) polymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate monomers; and d) copolymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate and (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and iii) one or more hydrocarbon-based oils: in a second, separate compartment: a composition (B) comprising: iv) one or more amine compound(s) chosen from: e) polyamine compounds bearing several primary amine and/or secondary amine groups, and f) amino alkoxysilanes, and optionally in a third compartment separate from the other two: a composition (C) comprising one or more cosmetic agents chosen from a) pigments, b) active agents for caring for keratin materials and e) UV-screening agents, and also d) mixtures thereof.

25. The oily dispersion (A) as defined in claim 1, comprising v) one or more cosmetic active agents it being understood that, when v) represents one or more pigment(s), then the dispersion is anhydrous and does not comprise any polyamine compound bearing several primary amine and/or secondary amine groups and does not comprise any amino alkoxysilanes.

26. An oily dispersion (A) comprising: i) one or more particles consisting of one or more ethylenic copolymers: a) of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and b) of ethylenically unsaturated anhydride compound; and ii) one or more stabilizers consisting of ethylenic polymers chosen from: c) polymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate monomers; and d) copolymers of (C.sub.3-C.sub.12)cycloalkyl acrylate or (C.sub.1-C.sub.6)(alkyl)acrylate and (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate; and iii) one or more hydrocarbon-based oils, and wherein the dispersion (A) is in inverse emulsion, i.e. of water-in-oil (W/O) type, and comprises one or more surfactants.

Description

EXAMPLES

Example 1

[0477] The oily dispersions (A) are formed as a whole [particles i)+stabilizer ii)] containing: [0478] 70% by weight of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate a) (such as ethyl acrylate), [0479] 10% by weight of ethylenically unsaturated anhydride compound b) (such as maleic anhydride), and [0480] 20% by weight of polymers of (C.sub.3-C.sub.12)cycloalkyl (C.sub.1-C.sub.6)(alkyl)acrylate monomers c) (such as isobornyl acrylate).

[0481] The preparation of these oily dispersions was performed in a 1 liter pilot reactor. The synthesis is performed in two steps:

[0482] In a first step, isobornyl acrylate is polymerized in isododecane/ethyl acetate (60/40) in the presence of a small amount of ethyl acrylate and of a radical initiator (T21S). In the first step, the isobornyl acrylate/ethyl acrylate mass ratio is 92/8.

[0483] In the second step, the rest of the ethyl acrylate and the maleic anhydride are added in the presence of isododecane/ethyl acetate (60/40) and of the radical initiator Trigonox 21S (T21S).

[0484] After stripping, the polymer is at a solids content of 52% in the isododecane. The ratios employed to obtain the stabilizer and the particulate core are summarized in the table below:

TABLE-US-00001 Mass percentage Mass percentage in Stabilizer - the stabilizer and Particulate core Monomer the particulate core Stabilizer ii) 22 Isobornyl acrylate 92 Ethyl acrylate 8 Particulate 78 Ethyl acrylate 87 core i) Maleic anhydride 13

[0485] Amount of Reagents:

[0486] Step 1:

TABLE-US-00002 Reagents: Mass (g) Isobornyl acrylate 50 Ethyl acrylate 4 T21S 0.54 Isododecane/EtOAc (60/40) 98

[0487] Isododecane added between the two steps:

TABLE-US-00003 Reagent Mass (g) Isododecane/EtOAc (60/40) 80

[0488] Step 2:

TABLE-US-00004 Mass added to the beaker Reagents: Mass (g) for the addition (g) Ethyl acrylate 171 196.65 Maleic anhydride 25 28.7 T21S 1.96 2.25 isododecane/EtOAc 196 225.4 (60/40)

[0489] Experimental Protocol:

[0490] Isododecane/ethyl acetate (60/40), isobornyl acrylate, ethyl acrylate and T21S are introduced as feedstock into a reactor. The medium is heated to 90° C. under argon and with stirring. The solids content during this first step is 35.9%.

[0491] After heating for 2 hours, NMR indicates an isobornyl acrylate consumption of 97% (ethyl acrylate consumption: 97%).

[0492] After 2 hours of reaction, isododecane/ethyl acetate (60/40) are introduced into the feedstock. The medium is heated to 90° C.

[0493] Once the medium is at 90° C., ethyl acrylate/maleic anhydride, isododecane/ethyl acetate (60/40) and T21S are introduced over 2 hours by pouring. At the end of the introduction by pouring, the medium is milky. The solids content is 40%.

[0494] After 7 hours of synthesis, traces of the starting monomers remain.

[0495] 1 L of isododecane and of ethyl acetate are then stripped out (NMR indicates that there are no more monomers and that the ethyl acetate has been totally removed from the dispersion). The solids content is about 52%.

Example 2

[0496] The combination of particles i)+stabilizer ii) was prepared in the following manner: [0497] 75% by weight of (C.sub.1-C.sub.4)alkyl (C.sub.1-C.sub.4)(alkyl)acrylate a) (such as ethyl acrylate), [0498] 5% by weight of ethylenically unsaturated anhydride compound b) (such as maleic anhydride), and [0499] 20% by weight of polymers of (C.sub.3-C.sub.12)cycloalkyl (C.sub.1-C.sub.6)(alkyl)acrylate monomers c) (such as isobornyl acrylate).

[0500] The synthesis was performed in a 1 liter pilot reactor in two steps:

[0501] In a first step, isobornyl acrylate is polymerized in isododecane/ethyl acetate (60/40) in the presence of a small amount of ethyl acrylate and of a radical initiator (T21S). In the first step, the isobornyl acrylate/ethyl acrylate mass ratio is 92/8.

[0502] In the second step, the rest of the ethyl acrylate and the maleic anhydride are added in the presence of isododecane/ethyl acetate (60/40) and of the radical initiator Trigonox 21S (T21S).

[0503] After stripping, the polymer is at a solids content of 49% in the isododecane.

[0504] The ratios employed to obtain the stabilizer and the particulate core are summarized in the table below:

TABLE-US-00005 Mass percentage Mass percentage in Stabilizer - the stabilizer and Particulate core Monomer the particulate core Stabilizer ii) 22 Isobornyl acrylate 92 Ethyl acryiate 8 Particulate 78 Ethyl acrylate 94 core i) Maleic anhydride 6

[0505] Amount of Reagents:

[0506] Step 1:

TABLE-US-00006 Reagents: Mass (g) Isobornyl acrylate 50 Ethyl acrylate 4 T21S 0.52 Isododecane/EtOAc (60/40) 96

[0507] Isododecane added between the two steps:

TABLE-US-00007 Reagent Mass (g) Isododecane/EtOAc (60/40) 80

[0508] Step 2:

TABLE-US-00008 Mass added to the beaker Reagents: Mass (g) for the addition (g) Ethyl acrylate 183.5 211.03 Maleic anhydride 12.5 14.38 T21S 1.96 2.25 Isododecane/EtOAc 196 225.4 (60/40)

[0509] Experimental Protocol:

[0510] Isododecane/ethyl acetate (60/40), isobornyl acrylate, ethyl acrylate and T21S are introduced as feedstock into the reactor. The medium is heated to 90° C. (nominal medium temperature) under argon and with stirring. The solids content during this first step is 35.9%. After heating for 2 hours, NMR indicates an isobornyl acrylate consumption of 98% (ethyl acrylate consumption: 97%).

[0511] After 2 hours of reaction, isododecane/ethyl acetate (60/40) are introduced into the feedstock. The medium is heated to 90° C.

[0512] Once the medium is at 90° C., ethyl acrylate/maleic anhydride, isododecane/ethyl acetate (60/40) and T21S are introduced over 2 hours by pouring. At the end of the introduction by pouring, the medium is milky. The solids content is 40%.

[0513] After 7 hours of synthesis, traces of the starting monomers remain.

[0514] 1 L of isododecane and of ethyl acetate are then stripped out (NMR indicates that there are no more monomers and that the ethyl acetate has been totally removed from the dispersion). The solids content is about 49%.

[0515] Amine Compounds Used:

TABLE-US-00009 Amine compound 1 Amine compound 2 Poly(dimethylsiloxane),bis(3- Bis-cetearyl amodimethicone, aminopropyl) 2-[(2-aminoethyl)amino]propyl Me, terminated (PDMS-diNH.sub.2) di-Me, [(C.sub.14-.sub.20- (CAS Number: 106214-84-0) alkyldimethylsilyl)oxy]-terminated (Mn = 50 000 g/mol) (CAS Number: 1126942-72-0)

[0516] Reaction of these amine compounds with the anhydride functions of the copolymer makes it possible to trap the nonvolatile oils and nevertheless to obtain deposits that do not transfer, that are not tacky and that are resistant to food oils and are glossy and comfortable.

[0517] Process for Application to Keratin Materials:

[0518] In a first stage, a formulation containing an oily dispersion of particles (A) was prepared (examples 1 and 2). The evaluations are performed on BioSkin or on a contrast card.

[0519] In this case, the contrast card reference is: Byk company—Product: Black scrub panels P121-10N, category number: 5015—dimension 165×432 mm. The formulations were then applied onto a glass support of the type such as byko-charts, black scrub panels from the company Byk and were left to dry for 24 hours.

[0520] In a first stage, a film of each formulation is deposited on a BioSkin sample by means of a film spreader. The BioSkin sample has the following approximate dimensions: (L: 10 cm; l: 6 cm; e: 2.5 mm). The thickness of the wet deposit is 50 μm. The films are dried for 24 hours at room temperature. The dry mass of formulation deposited on the BioSkin ranges between 60 and 100 mg. Once the films are dry, the tests may be performed.

[0521] After drying for 24 hours, formulation (B) containing an amine compound (compound 1 or 2) was applied.

[0522] After drying for 24 hours, evaluations of the deposits are performed: [0523] Deposition of 0.5 mL of olive oil or of water over 5 minutes onto the deposit. After 5 minutes of contact, cotton wool is wiped over 15 times and the degradation of the deposit is observed*. [0524] Feel of the deposit to observe the tacky nature and the transfer

[0525] For each combination, the evaluations were performed for composition (A) after drying and after application of composition (A) and (B) after drying. [0526] 0.5 mL of olive oil is applied to the film of formulation. After 5 minutes, the olive oil is removed by wiping 15 times with cotton wool. The deterioration of the film following contact with the olive oil and the transfer onto the cotton wool are thus examined.

[0527] If a deposit shows good resistance, the cotton wool remains white and the deposit has not degraded. Conversely, if substantial transfer is observed, the cotton wool is red and the film is completely degraded. The same protocol is applied with water

[0528] Thus, a grade is given for the resistance to olive oil/water but also for the transfer resistance ranging from: [0529] very good resistance: ++ to poor resistance: −− [0530] Transfer resistance: No transfer: ++ to substantial transfer: −−

[0531] Below are two examples of a good candidate for very good resistance to olive oil and for transfer resistance and of a poor candidate:

[0532] The evaluation and grading are performed in the following manner: [0533] very good resistance: ++ to poor resistance: −− [0534] Transfer resistance: No transfer: ++ to substantial transfer: −−

[0535] Fragmentation Test of the Formulations on BioSkin

[0536] As for the tests of resistance to olive oil and to Scotch, films are applied only on a sample of BioSkin. After drying for one day, the BioSkin plate is removed, by hand force, 10 times in the same manner.

[0537] The result may then be observed on the formulation film (fragmentation or otherwise).

[0538] In this case, a grade is given ranging from No fragmentation: ++ to substantial fragmentation: −−

[0539] Two response examples are presented below:

[0540] Protocol for Measuring the Gloss

[0541] Protocol for Measuring the Gloss

[0542] A film with a wet thickness of 50 μm is deposited on a contrast card.

[0543] The contrast card reference is: Byk company—Product: Byko-charts opacity 2A, category number: 2810—dimension 140×254 mm

[0544] The gloss is subsequently measured using a reference glossmeter: Lange company—Product: REFO 3D Portable glossmeter with three-angle geometry

Example 1: Formula Containing Only Volatile Oils—Polymer of Example 1+Amine Compound 1

[0545] Composition (A1)

TABLE-US-00010 Ingredients Amount (g) Combination of particle example 1, ingredients i), ii) 25 (a.m.) Pigment paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) Isododecane, ingredient iii) qs 100 a.m. = active material

[0546] Composition (B1)

TABLE-US-00011 Ingredients Amount (g) Amine compound 1, ingredient iv) 50 (a.m.) Isododecane, ingredient iii) 50

[0547] After application of compositions (A1) and (B1), deposits that are not tacky (++), transfer-resistant and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B1) is not applied, the tackiness is very much present and unsatisfactory (−−).

Example 2: Formula Containing Only Volatile Oils—Polymer of Example 1+Amine Compound 2

[0548] Composition (A2)

TABLE-US-00012 Ingredients Amount (g) Combination of particle example 1, ingredients i), ii) 25 (a.m.) Pigment paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) Isododecane, ingredient iii) qs 100

[0549] Composition (B2.

TABLE-US-00013 Ingredients Amount (g) Amine compound 2, ingredient iv) 10 (a.m.) Isododecane, ingredient iii) 90

[0550] After application of compositions (A2) and (B2), deposits that are not tacky (++), transfer-resistant (++) and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B2) is not applied, the tackiness is very much present and unsatisfactory (−−).

Example 3: Formula Containing Only Volatile Oils—Polymer of Example 2+Amine Compound 1

[0551] Composition (A3)

TABLE-US-00014 Ingredients Amount (g) Combination of particle example 2, ingredients i), ii) 25 (a.m.) Pigment paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) Isododecane, ingredient iii) qs 100

[0552] Compostion (B3)

TABLE-US-00015 Ingredients Amount (g) Amine compound 1, ingredient iv) 50 (a.m.) Isododecane, ingredient iii) 50

[0553] After application of compositions (A3) and (B3), deposits that are not tacky (++), transfer-resistant (++) and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B3) is not applied, the tackiness is very much present and unsatisfactory (−−) and the resistance to oil is less correct (−).

Example 4: Formula Containing Nonvolatile Oils: Polymer of Example 1+Amine Compound 1−Nonvolatile Oil: Pentaphenyl Silicone DC 555

[0554] Composition (A4)

TABLE-US-00016 Ingredients Amount (g) Combination of particle example 1, ingredients i), ii) 20 (a.m.) Pigment paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) DC 555 ingredient iii) 20  Isododecane, ingredient iii) qs 100

[0555] Composition (B4)

TABLE-US-00017 Ingredients Amount (g) Amine compound 1, ingredient iv) 50 (a.m.) Isododecane, ingredient iii) 50

[0556] After application of compositions (A4) and (B4), deposits that are not tacky (++), transfer-resistant (++) and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B4) is not applied, the tackiness is very much present and unsatisfactory (−−) and the resistance to oil is not satisfactory either (−−).

Example 5: Formula Containing Nonvolatile Oils: Polymer of Example 2+Amine Compound 1−Nonvolatile Oil: Pentaphenyl Silicone DC 555

[0557] Composition (A5)

TABLE-US-00018 Ingredients Amount (g) Combination of particle example 2, ingredients i), ii) 20 (a.m.) Pigment paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) DC 555 ingredient iii) 20  Isododecane, ingredient iii) qs

[0558] Composition (B5)

TABLE-US-00019 Ingredients Amount (g) Amine compound 1, ingredient iv) 50 (a.m.) Isododecane, ingredient iii) 50

[0559] After application of compositions (A5) and (B5), deposits that are not tacky (++), transfer-resistant (++) and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B5) is not applied, the tackiness is very much present and unsatisfactory (−−) and the resistance to oil is not satisfactory either (−−).

Example 6: Formula Containing Nonvolatile Oils: Polymer of Example 1+Amine Compound 1−Nonvolatile Oils: Octyldodecanol and Isododecane

[0560] Composition (A6)

TABLE-US-00020 Ingredients Amount (g) Combination of particle example 1, ingredients i), ii) 20 (a.m.) Pigmentary paste 40 wt % of DC Red 7 in isododecane, 5 ingredient v) Octyldodecanol, ingredient iii) 20  Isododecane, ingredient iii) qs

[0561] Composition (B6)

TABLE-US-00021 Ingredients Amount (g) Amine compound 1, ingredient iv) 50 (a.m.) Isododecane, ingredient iii) 50

[0562] After application of compositions (A6) and (B6), deposits that are not tacky (++), transfer-resistant (++) and resistant to daily attacking factors such as food oil (olive oil) and water (++) are finally observed, whereas when composition (B6) is not applied, the tackiness is very much present (−−) and unsatisfactory and the resistance to oil is not satisfactory either (−−).