Cosmetic and/or pharmaceutical composition comprising at least one copolymer comprising at least one ionizable group, and cosmetic treatment process

• US 20070264208A1
• Filed: 12/18/2006
• Published: 11/15/2007
• Est. Priority Date: 12/16/2005
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Mougin, Nathalie, Schultze, Xavier, Chodorowski-Kimmes, Sandrine
• Application Number:
  US11/640,420
• Publication Number:
  US 20070264208A1
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 8/8147 Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/87 Polyurethanes
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 3/02 Nail coatings
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring

Abstract

Disclosed herein is a cosmetic and/or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one (co)polymer comprising a polymer backbone and at least one junction group linked to the polymer backbone and capable of establishing H bonds with at least one partner junction group, each pairing of a junction group involving at least 3 H bonds, wherein the at least one (co)polymer comprises at least one ionizable group. Also disclosed herein is a cosmetic treatment process comprising applying the composition to keratin materials.

Claims

1. A cosmetic and/or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one (co)polymer comprising:

(a) a polymer backbone -POL- comprising at least two repeating units,

(b) at least one junction group (A) bonded to the polymer backbone and capable of establishing H bonds with at least one partner junction group, of identical or different chemical nature, each pairing of a junction group involving at least 3 H bonds,

wherein the at least one (co)polymer comprises at least one ionizable group.

2. The composition of claim 1, wherein each pairing of a junction group involves 4 H bonds.

3. The composition of claim 1, wherein the at least one (co)polymer results from the polymerization of at least one monomer of formula (I) and optionally of at least one monomer of formula (II) according to the reaction scheme:

wherein;

the groups G₁, which may be identical or different, are (co)polymerizable groups capable of forming a covalent bond with another (co)polymerizable group G₁ of another monomer (I) and/or with a (co)polymerizable group borne by a monomer G₂;

the groups A, which may be identical or different, are junction groups capable of forming at least three H bonds;

the arms L, which may be identical or different, are divalent linker arms, including a single covalent bond, linking a junction group A to a group G₁;

x is an integer greater than or equal to 1;

y is an integer greater than or equal to 1;

z is an integer greater than or equal to 1;

G₂, which may be identical or different, are monomers free of a junction group A and comprising at least one (co)polymerizable group capable of forming a covalent bond with a (co)polymerizable group G₁ of a monomer (I) and/or with a (co)polymerizable group borne by another identical or different monomer G₂;

m is the number of moles of identical or different, homopolymerized or copolymerized monomers of formula (I) and is an integer ranging from 1 to 12;

n is the number of moles of identical or different, homopolymerized or copolymerized monomers of formula (II), and is an integer ranging from 0 to 20 000; and

m+n≧

2;

wherein at least one of the groups A and/or groups G₁ and/or arms L and/or monomer G₂ comprises at least one ionizable group.

4. The composition of claim 3, wherein the groups A, which may be identical or different, are junction groups capable of forming 4 H bonds.

5. The composition of claim 3, wherein, in the at least one monomer of formula (I),

x is equal to 1 or 2,

y is equal to 1 or 2, and

z is equal to 1.

6. The composition of claim 3, wherein, in the at least one monomer of formula (I), m is an integer ranging from 2 to 6.

7. The composition of claim 3, wherein, in the at least one monomer of formula (II), n is an integer ranging from 1 to 5000.

8. The composition of claim 3, wherein the at least one (co)polymer is formed by reacting at least one monomer of formula G₁-L-A and/or G₁-L-A-L-G₁ and/or G₁-L(A)-G₁ with at least one monomer of formula G₂, wherein the groups G₁, the linker arms L, the junction groups A, and the monomers G₂ may be identical or different.

9. The composition of claim 1, wherein the at least one (co)polymer comprises at least 2 junction groups.

10. The composition of claim 9, wherein the at least one (co)polymer comprises at least 6 junction groups.

11. The composition of claim 1, wherein the at least one junction group (A) is a chemical group comprising at least 3 identical or different heteroatoms chosen from O, N, S, P, and F.

12. The composition of claim 11, wherein said at least one junction group (A) is a carbon-based group.

13. The composition of claim 12, wherein said at least one junction group (A) comprises four identical or different heteroatoms.

14. The composition of claim 1, wherein the at least one junction group (A) comprises at least 3 functional groups chosen from:

15. The composition of claim 1, wherein the at least one junction group (A) comprises 5- or 6-atom aromatic or unsaturated heterocyclic rings comprising C and/or N atoms, with conjugated double bonds.

16. The composition of claim 1, wherein the at least one junction group (A) is chosen from the following families and the tautomeric forms thereof:

(i) aminopyrimidones of formula;

(ii) ureidopyrimidones of formula;

(iii) acylaminopyridines chosen from;

monoacylaminopyridines of structure;

di(acylamino)pyridines of structure;

(iv) aminopyrimidines chosen from;

aminopyrimidine compounds;

diaminopyrimidine compounds of structures;

triaminopyrimidine compounds; and

ureidotriazines and ureidoaminotriazines of structure;

(vi) (acylamino)triazines chosen from;

di(acylamino)triazines of structure;

acylamino, aminotriazines, (mono- or diacylamino, and mono- or diamino) and compounds of structure;

acylaminotriazines of structure;

triaclaminotriazines,

(vii) aminotriazines chosen from;

monoaminotriazines,

2,6-diamino-s-triazines of structure;

triamino-s-triazine compounds of structure;

(viii) acylaminotriazoles of structure;

(ix) compounds of the urazoylbenzoic acid family of structure;

(x) phthalhydrazides of structure;

(xi) uracils of structure;

(xii) thymines of structure;

(xiii) succinimides of structure;

(xiv) glutarimides of structure;

(xv) compounds of the cyanuric acid family of structure;

(xvi) maleimides;

(xvii) compounds of the barbituric acid family of structure;

(xviii) compounds of structures;

(xix) compounds of the trimellitic family, of formula;

(xx) ureidopyridines of formulas;

(xxi) carbamoylpyridines of formulas;

(xxii) adenines of formula;

(xxiii) guanines of formula;

(xxiv) cytidines of formula;

wherein in groups (i)-(xxiv);

(a) the radicals R¹, which may be identical or different, are chosen from H, halogen, and monovalent linear, branched, or cyclic, saturated or unsaturated, optionally aromatic C₁-C₆₀₀₀ carbon-based groups, which may optionally comprise at least one heteroatom chosen from O, S, N, P, Cl, Br, and F;

or a combination of these meanings;

(b) the radicals R², which may be identical or different, are chosen from H, halogen, —

OH, —

N(R)₂, wherein R is chosen from H and linear or branched C₁-C₁₂ alkyl radicals; and

monovalent linear, branched, or cyclic, saturated or unsaturated, optionally aromatic C₁-C₆₀₀₀ hydrocarbon-based groups, which may optionally comprise at least one heteroatom chosen from O, S, N, P, and F;

or a combination of these meanings;

(c) the radicals R³, which may be identical or different, are chosen from H and monovalent linear, branched, or cyclic, saturated or unsaturated, optionally aromatic C₁-C₆₀₀₀ hydrocarbon-based groups, which may optionally comprise at least one heteroatom chosen from O, S, N, P, and F;

or a combination of these meanings;

with the proviso that at least one of the groups R¹ and R² is the point of attachment of the junction group A to the polymer backbone -POL-.

17. The composition of claim 16, wherein R¹ is chosen from C₄-C₁₂ cycloalkyl groups, linear or branched C₁-C₃₀ alkyl group, and C₄-C₁₂ aryl groups, which are optionally substituted with at least one function chosen from amino, ester, and hydroxyl functions.

18. The composition of claim 16, in which:

i) R¹ is chosen from C₄H₉, phenyl, 1,4-nitrophenyl, 1,2-ethylene, 1,6-hexylene, 1,4-butylene, 1,6-(2,4,4-trimethyl-hexylene), 1,4-(4-methylpentylene), 1,5-(5-methyl-hexylene), 1,6-(6-methylheptylene), 1,5-(2,2,5-trimethylhexylene), 1,7-(3,7-dimethyloctylene);

-isophorone-, 4,4′

-methylenebiscyclohexylene, 2-methyl-1,3-phenylene, 4-methyl-1,3-phenylene, and 4,4-biphenylenemethylene groups; and

/or

ii) R² is chosen from

H, CN, and NH₂,;

C₁-C₃₀ alkyl groups,

C₄-C₁₂ cycloalkyl groups,

C₄-C₁₂ aryl groups,

(C₄-C₁₂)aryl(C₁-C₃₀)alkyl groups,

C₁-C₄ alkoxy groups,

arylalkoxy groups,

C₄-C₁₂ heterocycles,

thioalkoxy groups,

sulfoxy groups, and

mixtures thereof;

wherein these groups may be optionally substituted with at least one function chosen from amino, ester, and hydroxyl functions; and

/or

iii) R³ is chosen from C₄-C₁₂ cycloalkyl groups;

linear or branched C₁-C₃₀ alkyl groups, and C₄-C₁₂ aryl groups;

optionally substituted with at least one function chosen from amino, ester, and hydroxyl functions; and

/or

iv) the point of attachment is borne by R₁ and/or R₂.

19. The composition of claim 16, wherein the at least one junction group (A) is chosen from:

(a) self-complementary and identical junction groups (A) chosen from;

aminopyrimidones and ureidopyrimidones,

compounds of the trimellitic acid family and of urazoylbenzoic acid,

acylaminopyridines, ureidopyridines, and carbamoylpyridines,

acylaminotriazines, ureidotriazines, and diaminotriazines,

acylaminotriazoles,

phthalhydrazides, and

compounds of formulas;

wherein R¹ is chosen from H and monovalent linear, branched, or cyclic, saturated or unsaturated, optionally aromatic, C₁-C₆₀₀₀ hydrocarbon-based groups, which may optionally comprise at least one heteroatom chosen from O, S, N, P, and F.

(b) complementary but different junction groups (A) chosen from;

adenine, which is complementary to guanine,

cytidine, which is complementary to thymine,

triamino-s-triazine, which is complementary to uracil, succinimide, glutarimide, cyanuric acid, thymine, maleimide, (di)aminopyrimidine, and barbituric acid; and

acylaminoamino-s-triazine, which is complementary to uracil, succinimide, glutarimide, cyanuric acid, thymine, maleimide, (di)aminopyrimidine, and barbituric acid.

20. The composition of claim 16, wherein the at least one junction group (A) is chosen from groups capable of establishing at least three H bonds with each other (self-complementary), chosen from:

ureidopyrimidones;

ureidopyridines and carbamoylpyridines;

acylamino-s-triazines;

ureidotriazines;

phthalhydrazines; and

compounds of formulas;

21. The composition of claim 16, wherein the at least one junction group (A) is chosen from:

2-ureidopyrimidone;

6-methyl, 2-ureidopyrimidone;

diacyl-2,6-diamino-s-triazine;

ureido-s-triazine; and

compounds of formulas;

wherein R¹ is chosen from H and monovalent, linear, branched, or cyclic, saturated or unsaturated, optionally aromatic C₁-C₆₀₀₀ hydrocarbon-based groups which may optionally comprise at least one heteroatom chosen from O, S, N, P, and F.

22. The composition of claim 1, wherein the at least one junction group (A) bears at least one ionizable group.

23. The composition of claim 3, wherein the linker arm L is chosen from single covalent bonds and saturated or unsaturated, linear, branched, or cyclic, and aromatic divalent carbon-based groups, and combinations thereof, comprising from 1 to 6000 carbon atoms, and optionally comprising at least one identical or different heteroatom chosen from O, N, S, P, and F.

24. The composition of claim 23, wherein the divalent carbon based groups comprise from 1 to 30 carbon atoms.

25. The composition of claim 23, wherein the linker arms L are carbon-based groups optionally comprising at least one functional group chosen from:

26. The composition of claim 23, wherein the linker arm L, when it is not a single bond, bears at least one ionizable group.

27. The composition of claim 3, wherein the (co)polymerizable group G₁ is chosen from:

(co)polymerizable groups comprising at least one ethylenic double bond capable of undergoing radical, anionic, or cationic (co)polymerization;

groups that may be (co)polymerized via nucleophilic or electrophilic substitution or addition, or radical addition, chosen from groups comprising at least one function chosen from hydroxyl (OH), activated hydroxyl, thiol (SH), halide (Br and Cl), primary and secondary amine (NH₂ and NHR), ester (COOR), carboxylic acid (COOH), activated acid, protected or unprotected isocyanate (NCO), isothiocyanate (NCS), —

C═

C—

, —

C(O)H, —

SiH, succinimide, oxazoline, acetal, hemiacetal, chlorotriazine, —

SO₂Cl, and epoxide functions;

wherein the radical R is chosen from C₁-C₆ alkyls; and

groups that may be (co)polymerized via anionic or cationic ring opening, chosen from groups comprising at least one group chosen from cyclic ether, cyclic ester, cyclic amide, and cyclic carbonate groups.

28. The composition of claim 3, wherein the group G₁ bears at least one ionizable group.

29. The composition of claim 3, wherein the at least one monomer of formula (I) is chosen from:

i) monomers that may undergo radical, anionic, or cationic (co)polymerization, represented by the formula;

wherein P, Q, and T, which may be identical or different, are chosen from hydrogen, linear or branched, cyclic or non-cyclic, saturated or unsaturated, or aromatic, hydrocarbon-based radicals comprising from 1 to 12 carbon atoms, and a group -L-A;

ii) monomers that may be (co)polymerized via addition or polycondensation, comprising at least one group G₁, which can (co)polymerize via addition or polycondensation;

iii) monomers that (co)polymerize via ring opening, and comprising groups G₁ chosen from;

cyclic ethers of formula;

wherein R is chosen from H and linear or branched, cyclic or non-cyclic, saturated or unsaturated, or aromatic, hydrocarbon-based radicals, and n is an integer ranging from 1 to 3;

cyclic amides of formula;

wherein R is —

(CH₂)_m— and

m is an integer ranging from 3 to 12, and n is an integer ranging from 1 to 3;

cyclic esters of formula;

wherein R is —

(CH₂)_m— and

m is an integer ranging from 3 to 12, and n is an integer ranging from 1 to 3;

cyclic carbonates of formula;

wherein R is —

(CH₂)_m— and

m is an integer ranging from 3 to 12, and n is an integer ranging from 1 to 3;

cyclic perfluoroethers, lactides, oxazolines, and norbornene, and derivatives thereof; and

combinations thereof.

30. The composition of claim 29, wherein the monomers that may be (co)polymerized via addition or polycondensation comprise one group chosen from A-L- and -L-A-L-.

31. The composition of claim 29, wherein the at least one monomer (I) is chosen from:

monomers that may undergo radical, anionic, or cationic (co)polymerization, of formula;

the acrylate derived from 6-methyl-2-ureidopyrimidone of formula;

monomers of formulas;

wherein

Z is chosen from —

O—

C(O)— and

—

NH—

C(O)—

;

n is an integer ranging from 1 to 500;

R^b is chosen from H and CH₃; and

A is the group;

wherein R², which may be identical or different, is chosen from H, halogen, —

OH, —

N(R)₂, wherein R is chosen from H and linear or branched C₁-C₁₂ alkyl radicals; and

monovalent linear, branched, or cyclic, saturated or unsaturated, optionally aromatic C₁-C₆₀₀₀ hydrocarbon-based groups, which may optionally comprise at least one heteroatom chosen from O, S, N, P, and F;

or a combination of these meanings;

monomers that may be (co)polymerized via polyaddition or polycondensation, of formulas;

32. The composition of claim 3, wherein the at least one monomer (II) G₂ is an ethylenic monomer chosen from:

i) (meth)acrylates of formulas CH₂═

CHCOOR⁴ and CH₂═

C(CH₃)COOR⁴ in which R⁴ is chosen from;

hydrogen,

linear, cyclic, or branched alkyl groups comprising from 1 to 30 carbon atoms, in which is optionally intercalated at least one heteroatom chosen from O, N, S, and P, the alkyl groups also optionally being substituted with at least one substituent chosen from hydroxyl groups, halogen atoms, and groups Si(R₇)(R₈) wherein R₇ and R₈, which may be identical or different, are chosen from C₁-C₆ alkyl groups and phenyl groups;

C₃ to C₂₀ aryl groups;

C₄ to C₃₀ aralkyl and alkylaryl groups, wherein the alkyl group is C₁ to C₈;

C₄-C₁₂ heterocycloalkyl groups comprising at least one heteroatom chosen from O, N, P, and S, the ring being aromatic or non-aromatic;

C₄-C₃₀ alkylheterocycloalkyl groups, wherein the alkyl group is C₁ to C₈,

wherein the aryl and aralkyl groups may optionally comprise at least one intercalated heteroatom chosen from O, N, S, and P, and/or may be substituted with at least one substituent chosen from hydroxyl groups, halogen atoms, and linear or branched C₁-C₄ alkyl groups, which may themselves comprise at least one intercalated heteroatom chosen from O, N, S, and P and/or which may be substituted with at least one substituent chosen from hydroxyl groups, halogen atoms and groups Si(R₇)(R₈), wherein R₇ and R₈, which may be identical or different, are chosen from C₁ to C₆ alkyl groups and phenyl groups;

ii) (meth)acrylamides of formulas CH₂═

CHCONR⁶R⁵ and CH₂—

C(CH₃)CONR⁶R⁵ wherein R⁵ and R⁶, which may be identical or different, have the same meanings as for the groups R⁴ above;

iii) vinyl monomers of formulas;

CH₂═

CH—

R⁹, CH₂═

CH—

CH₂—

R⁹, and CH₂═

C(CH₃)—

CH₂—

R⁹ wherein R⁹ is chosen from hydroxyl, halogen (Cl and F), NH₂, acetamide (—

NHCOCH₃), —

OR₁₀ (vinyl ether) groups wherein R₁₀ is chosen from phenyl groups and C₁-C₁₂ alkyl groups;

—

OCOR₁₁, (vinyl ester) groups wherein R₁₁ is chosen from;

(i) linear or branched C₂ to C₁₂ alkyl groups,

(ii) C₃ to C₁₂ cycloalkyl groups,

(iii) C₃ to C₂₀ aryl groups,

(iv) C₄ to C₃₀ aralkyl groups, wherein the alkyl group is C₁ to C₈,

(v) saturated or unsaturated, aromatic or non-aromatic, 4- to 12-membered heterocycloalkyl groups comprising at least one heteroatom chosen from O, N, and S, and

(vi) C₁ to C₄ alkylheterocycloalkyl groups,

wherein the alkyl, cycloalkyl, aryl, aralkyl, heterocycloalkyl, and alkylheterocycloalkyl groups are optionally substituted with at least one substituent chosen from hydroxyl groups, halogen atoms, and linear or branched C₁ to C₄ alkyl groups in which is optionally intercalated at least one heteroatom chosen from O, N, S, and P, the alkyl groups also optionally being substituted with at least one substituent chosen from hydroxyl groups, halogen atoms and groups Si(R₇)(R₈) wherein R₇ and R₈, which may be identical or different, are chosen from C₁ to C₆ alkyl groups and phenyl groups; and

iv) (meth)acrylate, (meth)acrylamide, and vinyl monomers comprising at least one group chosen from fluoro and perfluoro groups.

33. The composition of claim 32, wherein R⁴ is chosen from methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, stearyl, isooctyl, isodecyl, and dodecyl groups;

alkyl-based groups chosen from C₁-C₄ hydroxyalkyl groups;

(C_1-4)alkoxy(C_1-4)alkyl groups;

C₃ to C₁₂ cycloalkyl groups;

t-butylbenzyl, phenyl, furfurylmethyl, tetrahydrofurfurylmethyl, and 2-ethylperfluorohexyl groups;

the groups —

(OC₂H₄)_q—

OR, wherein q=5 to 500 and R is chosen from H and C₁ to C₃₀ alkyl radicals.

34. The composition of claim 32, wherein the at least one monomer (II) is chosen from (meth)acrylamide, N-ethyl(meth)acrylamide, N-butylacrylamide, N-t-butylacrylamide, N-isopropylacrylamide, N,N-dimethyl(meth)acrylamide, N,N-dibutylacrylamide, N-octylacrylamide, N-dodecylacrylamide, undecylacrylamide and N-(2-hydroxypropylmethacrylamide);

vinylcyclohexane, styrene, N-vinylpyrrolidone, N-vinylcaprolactam;

vinyl acetate, vinyl propionate, vinyl butyrate, vinyl ethylhexanoate, vinyl neononanoate, vinyl neododecanoate;

methyl vinyl ether, ethyl vinyl ether, and isobutyl vinyl ether.

35. The composition of claim 32, wherein the at least one monomer (II) G₂ bears at least one ionizable group.

36. The composition of claim 3, wherein in the at least one monomer (I):

the group G-L-A-L-G is of the type;

and/or

the group A-L-G is of the type;

wherein the radicals R′

₁, R′

₂, and R′

₃, which may be identical or different, are divalent carbon-based groups chosen from 1,2-ethylene, 1,6-hexylene, 1,4-butylene, 1,6-(2,4,4-trimethylhexylene), 1,4-(4-methylpentylene), 1,5-(5-methylhexylene), 1,6-(6-methylheptylene), 1,5-(2,2,5-trimethylhexylene), 1,7-(3,7-dimethyloctylene);

-isophorone-, 4,4′

-methylenebis(cyclohexylene), tolylene, 2-methyl-1,3-phenylene, 4-methyl-1,3-phenylene, and 4,4-bis(phenylene)methylene.

37. The composition of claim 36, wherein the radicals R′

₁, R′

₂, and R′

₃, which may be identical or different, are chosen from isophorone, —

(CH₂)₂—

, —

(CH₂)₆—

, —

CH₂CH(CH₃)—

CH₂—

C(CH₃)₂—

CH₂—

CH₂, 4,4′

-methylenebis(cyclohexylene), and 2-methyl-1,3-phenylene.

38. The composition of claim 3, wherein the at least one ionizable group is borne by a linker arm L of the monomer (I) when L is not a single bond, or by the monomer (II) G₂ when it is present in the (co)polymer.

39. The composition of claim 3, wherein:

the at least one ionizable group is present in the (co)polymer in an amount ranging from 0.1% to 50% by weight relative to the total weight of the (co)polymer; and

/or

the at least one monomer bearing the at least one ionizable group is present in the (co)polymer in an amount ranging from 3% to 20% by weight relative to the total weight of the (co)polymer.

40. The composition of claim 39, wherein the at least one ionizable group is present in the (co)polymer in an amount ranging from 1% to 15% by weight relative to the total weight of the (co)polymer.

41. The composition of claim 39, wherein the at least one monomer is present in the (co)polymer in an amount ranging from 8% to 15% by weight relative to the total weight of the (co)polymer.

42. The composition of claim 1, wherein the at least one ionizable group is chosen from:

i) anionizable groups, and salts thereof; and

ii) cationizable groups, and salts thereof.

43. The composition of claim 42, wherein said anionizable groups are chosen from groups comprising an acid function chosen from:

carboxylic radicals;

—

COOH,

sulfonic radicals;

—

SO₃H, —

OSO₃H radicals,

phosphonic radicals;

—

(O)P(OH)₂,

phosphoric radicals;

—

OP(O)(OH)₂, and

organic or mineral salified forms thereof.

44. The composition according to claim 42, wherein said cationizable groups are chosen from groups comprising a function chosen from:

a) amine radicals of formula —

N(R₁₅)(R₁₆) and organic or mineral salts thereof, wherein R₁₅ and R₁₆, which may be identical or different, are chosen from;

(i) hydrogen,

(ii) linear, branched, or cyclic, saturated or unsaturated, optionally aromatic alkyl groups comprising from 1 to 30 carbon atoms and optionally comprising from 1 to 10 heteroatoms chosen from O, N, S, and P;

(iii) alkylene oxide groups of formula —

(R₁₇O)_rR₁₈ wherein R₁₇ is chosen from linear or branched C₂-C₄ alkyl radicals, R₁₈ is chosen from hydrogen and linear or branched C₁ to C₃₀ alkyl radicals, and r is a number ranging from 1 to 250;

wherein R₁₅ and R₁₆ may form, together with the nitrogen atom, a saturated or unsaturated, optionally aromatic ring comprising from 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

the ring also optionally being fused with at least one other saturated or unsaturated, optionally aromatic ring comprising from 5 to 7 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

b) —

R′

₁₅—

N—

R′

₁₆—

groups wherein R′

₁₅ and R′

₁₆ form, together with the nitrogen atom, a saturated or unsaturated, optionally aromatic ring comprising 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

the ring optionally being fused with at least one other saturated or unsaturated, optionally aromatic ring comprising from 5 to 7 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

c) guanidino groups and amidino groups;

d) quaternary ammonium radicals of formula;

—

N⁺(R²)₃Z⁻

wherein R¹², which may be identical or different, is chosen from linear or branched C₁ to C₂₀ alkyl radicals; and

Z is chosen from halogen atoms and —

OSO₃CH₃;

e) and mixtures thereof.

45. The composition of claim 1, wherein the at least one ionizable group is chosen from:

anionizable groups;

monovalent groups —

COOH, —

CH₂COOH, —

(CH₂)₂COOH, —

(CH₂)₃COOH, —

(CH₂)SO₃H, —

(CH₂)₂SO₃H, —

(CH₂)₃SO₃H, and —

O(CH₂)₃SO₃H; and

divalent groups —

C(COOH)(CH₃)— and

—

CH₂—

C(COOH)(CH₃)—

CH₂—

; and

cationizable groups;

monovalent groups —

(CH₂)₂—

N(CH₃)₂, —

N(CH₃)₂, (CH₂)₃—

N(CH₃)₂, —

O—

(CH₂)₃—

N(CH₂CH₃)₂, and —

(CH₂)₂—

N(CH₂CH₃)₂; and

divalent groups —

(CH₂)₂—

N(CH₃)—

(CH₂)₂— and

—

(CH₂)₃—

N(CH₃)—

(CH₂)₃—

.

46. The composition of claim 3, wherein the group G₁ bears at least one ionizable group and is chosen from the groups CH₂═

C(COOH)—

COO— and

HOC(CH₃)(COOH)—

.

47. The composition of claim 46, wherein the group G₁-L-A is chosen from:

the group CH₂═

C(COOH)—

COO—

CH₂OCONH(CH₂)₆—

ureidopyrimidone of formula;

the group HOC(CH₃)(COOH)—

CH₂CH₂OC(O)—

NH(CH₂)₆—

ureidopyrimidone of formula;

48. The composition of claim 3, wherein the at least one monomer (II) G₂ comprises at least one ionizable group and is chosen from:

(i) ethylenically unsaturated monomers comprising at least one function chosen from carboxylic acid (COOH), phosphonic acid (PO₃H₂), and sulfonic acid (SO₃H) functions,

(ii) ethylenically unsaturated monomers comprising at least one function chosen from primary, secondary, and tertiary amine functions,

(iii) monomers of formula;

wherein;

R₁₉ is chosen from hydrogen and linear, cyclic, or branched hydrocarbon-based radicals of the type C_pH_2p+1, wherein p is an integer ranging from 1 to 12;

Z₁ is a divalent group chosen from —

COO—

, —

CONH—

, —

CONCH₃—

, —

OCO—

, and —

O—

;

z₁ is equal to 0 or 1;

Z₂ is chosen from linear, branched, or cyclic, optionally aromatic, saturated or unsaturated divalent carbon-based radicals comprising from 1 to 30 carbon atoms, which may optionally comprise from 1 to 30 heteroatoms chosen from O, N, S, and P;

z₂ is equal to 0 or 1;

Z₅ has the same meaning as that given for Z₂, but may be different from Z₂,

z₅=0 or 1,

X′

⁺ is a divalent group of formula —

N⁺(R₆)(R₇)—

wherein (i) R₆ and R₇, which may be identical or different, are chosen from hydrogen and linear, branched, or cyclic, optionally aromatic alkyl groups comprising from 1 to 25 carbon atoms, and optionally comprising from 1 to 20 heteroatoms chosen from O, N, S, and P; and

(ii) R₆ and R₇ may form, together with the nitrogen atom, a first saturated or unsaturated, optionally aromatic ring comprising from 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, N and S;

the first ring optionally being fused with at least one other saturated or unsaturated, optionally aromatic ring comprising from 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, N, and S; and

Y′

⁻

is a group chosen from —

COO⁻

, —

SO₃⁻

, —

OSO₃⁻

, —

PO₃²⁻

, and —

OPO₃²⁻

;

(iv) monomers of formula HX″

—

B—

X″

H, wherein;

X″

, which may be identical or different, is chosen from O, S, NH, and NR, wherein R is chosen from C_1-6 alkyl groups,

B is chosen from linear, branched, or cyclic, saturated or unsaturated, optionally aromatic alkylene radicals comprising from 1 to 6000 carbon atoms, optionally comprising at least one heteroatom chosen from O, S, P, and N, and/or optionally substituted with at least one atom chosen from fluorine and silicon atoms;

with the proviso that at least one of the radicals B bears at least one ionizable group.

49. The composition of claim 48, wherein said ethylenically unsaturated monomers comprising at least one function chosen from carboxylic acid (COOH), phosphonic acid (PO₃H₂), and sulfonic acid (SO₃H) functions is chosen from compounds of the following formula:

CH₂═

C(R₁₉)-(Z₁)_z1-(Z₂)_z2-Y

wherein;

R₁₉ is chosen from hydrogen and linear, cyclic, or branched hydrocarbon-based radicals of the type C_pH_2p+1, wherein p is an integer ranging from 1 to 12;

Z₁ is a divalent group chosen from —

COO—

, —

CONH—

, —

CONCH₃—

, —

OCO—

, and —

O—

;

z₁ is 0 or 1;

Z₂ is chosen from linear, branched, or cyclic, optionally aromatic, saturated or unsaturated divalent carbon-based radicals comprising from 1 to 30 carbon atoms, which may optionally comprise from 1 to 30 heteroatoms chosen from O, N, S, and P;

z₂ is 0 or 1; and

Y is a group chosen from —

COOH, —

SO₃H, —

OSO₃H, —

PO(OH)₂, and —

OPO(OH)₂.

50. The composition of claim 48, wherein the ethylenically unsaturated monomers comprising at least one primary, secondary, or tertiary function are chosen from those of the following formula:

wherein;

R₁₉ is chosen from hydrogen and linear, cyclic, or branched hydrocarbon-based radicals of the type C_pH_2p+1, wherein p is an integer ranging from 1 to 12;

Z₁ is a divalent group chosen from —

COO—

, —

CONH—

, —

CONCH₃—

, —

OCO—

, and —

O—

;

z₁ is 0 or 1;

Z₂ is chosen from linear, branched, or cyclic, optionally aromatic, saturated or unsaturated divalent carbon-based radicals comprising from 1 to 30 carbon atoms, which may optionally comprise from 1 to 30 heteroatoms chosen from O, N, S, and P;

z₂ is 0 or 1; and

X is a group of formula —

N—

R₁₇R₁₈ wherein R₁₇ and R₁₈, which may be identical or different, are chosen from,

(i) hydrogen;

(ii) linear, branched, or cyclic, saturated or unsaturated, optionally aromatic alkyl groups comprising from 1 to 30 carbon atoms, which may optionally comprise from 1 to 10 heteroatoms chosen from O, N, S, and P;

(iii) alkylene oxide groups of formula —

(R₂₀O)_yR₂₁ wherein R₂₀ is chosen from linear or branched C₂-C₄ alkyl radicals, R₂₁ is chosen from hydrogen and linear or branched C₂-C₃₀ alkyl radicals, and y is a number ranging from 1 to 250;

(iv) R₁₇ and R₁₈ may form, together with the nitrogen atom, a saturated or unsaturated optionally aromatic ring comprising from 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

the ring also optionally being fused with at least one other saturated or unsaturated, optionally aromatic ring comprising from 5 to 7 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

or alternatively X is a group —

R′

₁₅—

N—

R′

₁₆—

wherein R′

₁₅ and R′

₁₆ form, together with the nitrogen atom, a saturated or unsaturated, optionally aromatic ring, comprising from 5 to 8 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N;

the ring optionally being fused with at least one other saturated or unsaturated, optionally aromatic ring comprising from 5 to 7 atoms chosen from carbon atoms and heteroatoms chosen from O, S, and N.

51. The composition of claim 48, wherein:

i) Z₂ is chosen from;

alkylene radicals chosen from methylene, ethylene, propylene, n-butylene, isobutylene, tert-butylene, n-hexylene, n-octylene, n-dodecylene, n-octadecylene, n-tetradecylene, and n-docosanylene;

phenylene radicals —

C₆H₄-(ortho, meta, or para), which may be optionally substituted with a C₁-C₁₂ alkyl radical optionally comprising from 1 to 8 heteroatoms chosen from O, N, S, and P;

benzylene radicals —

C₆H₄—

CH₂—

, which may be optionally substituted with a C₁-C₁₂ alkyl radical optionally comprising from 1 to 8 heteroatoms chosen from O, N, S, and P;

radicals of formulas —

CH₂—

CH(OH)—

, —

CH₂—

CH₂—

CH(OH)—

, —

CH₂—

CH₂—

CH(NH₂)—

, —

CH₂—

CH(NH₂)—

, —

CH₂—

CH₂—

CH(NHR′

)—

, —

CH₂—

CH(NHR′

)—

, —

CH₂—

CH₂—

CH(NR′

R″

)—

, —

CH₂—

CH(NR′

R″

)—

, and —

CH₂—

CH═

CH—

wherein R′ and

R″

, which may be identical or different, are chosen from C₁-C₁₈ alkyl radicals;

and/or

ii) X is chosen from aromatic or non-aromatic rings comprising a cationizable tertiary amine group and from aromatic or non-aromatic heterocycles comprising a cationizable tertiary nitrogen; and

/or

iii) Z₂ and Z₅, which may be identical or different, are chosen from saturated or unsaturated linear, branched, or cyclic (aromatic or non-aromatic) alkylene groups comprising from 1 to 30 carbon atoms, and optionally including at least one heteroatom chosen from O, N, S, and P; and

/or

iv) B is chosen from;

alkylene radicals comprising from 1 to 40 carbon atoms and cycloalkylene radicals comprising from 3 to 16 carbon atoms, optionally substituted with a C₁-C₁₂ alkyl radical and/or optionally comprising from 1 to 8 heteroatoms chosen from O, N, S, F, Si, and P;

C₁-C₃₀ arylene radicals;

C₁ to C₃₀ alkylarylene and arylalkylene radicals optionally substituted with a C₁-C₁₂ alkyl radical optionally comprising from 1 to 25 heteroatoms chosen from O, N, S, F, Si, and P;

and B may comprise at least one radical chosen from;

radicals of formulas —

O—

CO—

O—

, —

CO—

O—

, —

OCO—

, —

O—

CO—

NH—

, anhydride, —

NH—

CO—

NH—

, and NHCO;

radicals —

Si(R₄)(R₅)O—

wherein R₄ and R₅, which may be identical or different, are chosen from H and linear or branched, cyclic or non-cyclic, saturated or unsaturated, or aromatic hydrocarbon-based radicals optionally comprising at least one identical or different heteroatom chosen from O, N, S, P, F, and Si; and

/or

oxyalkylene and aminoalkylene radicals.

52. The composition of claim 48, wherein the at least one monomer (II) G₂ is chosen from:

a) acrylic acid, methacrylic acid, crotonic acid, itaconic acid, fumaric acid, maleic acid, diacrylic acid, dimethylfumaric acid, citraconic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, vinylbenzoic acid, vinylphosphoric acid, vinylsulfonic acid, vinylbenzenesulfonic acid, acrylamidoglycolic acid of formula CH₂═

CH—

CONHCH(OH)COOH, vinylphosphonic acid;

2-carboxyethyl (meth)acrylate, sulfopropyl methacrylate or acrylate (CH₂═

C(CH₃)CO₂(CH₂)₃SO₃H), sulfoethyl(meth)acrylate, vinyl methyl sulfone, 2-(methacryloyloxy)ethyl phosphate of formula CH₂═

C(CH₃)COOC₂H₄OP(O)(OH)₂;

diallyl maleate of formula C₃H₅—

CO₂—

CH═

CH—

CO₂—

C₂H₅;

carboxylic anhydrides bearing a vinyl bond, and the salts thereof;

b) 2-vinylpyridine, 4-vinylpyridine, allylamine, and allylpyridine;

aminoalkyl(meth)acrylates;

aminoalkyl(meth)acrylamides;

vinylamine, vinylimidazole, and 2-(diethylamino)ethylstyrene;

N-vinylimidazole, N-vinyl-2-methylimidazole, and N-vinylcarbazole; and

the salts thereof and/or the quaternized forms thereof;

c) N,N-dimethyl-N-(2-methacryloyloxyethyl)-N-(3-sulfopropyl)ammonium betaine, N,N-dimethyl-N-(3-methacrylamidopropyl)-N-(3-sulfopropyl)ammonium betaine, and 1-(3-sulfopropyl)-2-vinylpyridinium betaine;

d) dimethylolpropionic acid, dimethylaminopropionic acid, N-ethylsulfonicdimethanolamine, N-ethylsulfonicdiethanolamine, benzenesulfonic acid diol, diaminopyridine, N-methyldiethanolamine, N-ethyldiethanolamine, and N-tert-butyldiethanolamine, and

e) mixtures thereof.

53. The composition of claim 1, wherein the at least one (co)polymer is chosen from those of the following structures:

linear (co)polymers α

,ω

-functionalized with junction groups (A);

linear (co)polymers comprising more than two junction groups, located in the chain and/or at one or both ends and/or as branches; and

/or

branched (co)polymers with junction groups in the chain and/or as branches and/or at one or both ends.

54. The composition of claim 1, wherein the at least one (co)polymer is chosen, with the proviso that it comprises at least one ionizable group, from:

polyurethanes, polyureas, aliphatic or aromatic polyesters, aliphatic or aromatic polyamides, and copolymers thereof;

ethylenic (co)polymers chosen from (meth)acrylic copolymers, (meth)acrylamide copolymers, allylic copolymers, copolyolefins, and mixtures thereof;

(co)polymers obtained via ring opening;

polycaprolactams and polypyrrolidones;

siloxane (co)polymers;

polythioethers, polycarbonates, polyacetals, and perfluoropolyethers;

(co)polymers obtained via metathesis;

copolymers of these various types of polymers;

the salts thereof and derivatives thereof; and

mixtures thereof.

55. The composition of claim 54, wherein the (co)polymers obtained via ring opening are chosen from polyethylene oxide, polypropylene oxide and copolymers thereof (polyethylene oxide/polypropylene oxides);

polylactides, polyesters, and polyoxazolines.

56. The composition of claim 1, wherein the at least one (co)polymer has a number-average molecular mass (Mn) ranging from 1000 to 3 000 000.

57. The composition of claim 56, wherein the at least one (co)polymer has a number-average molecular mass (Mn) ranging from 8000 to 500 000.

58. The composition of claim 1, wherein the at least one (co)polymer is soluble and/or dispersible in the medium of the composition.

59. The composition of claim 58, wherein the at least one (co)polymer is soluble in aqueous media, carbon-based oils, silicone oils, and/or cosmetic solvents.

60. The composition of claim 1, wherein the at least one (co)polymer is present in the composition in an amount ranging from 0.01% to 90% by weight of solids relative to the total weight of the composition.

61. The composition of claim 60, wherein the at least one (co)polymer is present in the composition in an amount ranging from 1% to 50% by weight of solids relative to the total weight of the composition.

62. The composition of claim 1, wherein the physiologically acceptable medium comprises a compound chosen from water, alcohols, polyols, esters, liquid ketones, propylene glycol ethers that are liquid at room temperature, ethers that are liquid at 25°

C., alkanes that are liquid at 25°

C., aldehydes that are liquid at 25°

C., cyclic aromatic compounds that are liquid at 25°

C., carbon-based oils, silicone oils, fluorosilicone oils, waxes, gums, surfactants, thickeners, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic cosmetic active agents, preserving agents, antioxidants, fragrances, nacreous agents, fillers, neutralizers, polymers other than the at least one (co)polymer, film-forming polymers, emulsifiers, co-emulsifiers, pigments, dyestuffs, nacres, and mixtures thereof.

63. The composition of claim 1, wherein the composition is in a form chosen from aqueous, alcoholic, or aqueous-alcoholic solutions, dispersions, and suspensions and oily solutions, which are optionally thickened or gelled;

oil-in-water emulsions, water-in-oil emulsions, and multiple emulsions, of liquid or semi-liquid consistency of the milk type or of soft consistency of cream type;

aqueous or anhydrous gels and mousses;

oily or emulsified gels;

dispersions of vesicles;

two-phase or multiphase lotions;

sprays; and

any other cosmetic form.

64. The composition of claim 1, wherein the composition is in a form chosen from products for caring for, cleansing, and/or making up bodily and/or facial skin, the lips, and/or the hair, antisun and/or self-tanning products, body hygiene products, and hair products for caring for, cleansing, styling, and/or dyeing the hair.

65. The composition of claim 1, wherein the composition is chosen from:

hair compositions chosen from shampoos, hair conditioners, styling and/or care gels, care lotions and creams, conditioning agents, hairsetting lotions, blow-drying lotions, fixing and/or styling compositions;

hair coloring products;

compositions for permanent-waving, relaxing, and/or bleaching the hair;

rinse-out compositions to be applied before and/or after dyeing, bleaching, permanent-waving, and/or relaxing the hair or alternatively between the two steps of a permanent-waving or hair-relaxing operation;

care compositions chosen from moisturizing compositions for the skin, the lips, and/or the integuments,

skin cleansing compositions chosen from makeup-removing products and bath or shower gels;

uncolored care products for treating the skin, moisturizing the skin, smoothing the skin out, depigmenting the skin, nourishing the skin, protecting the skin from sunlight, and/or giving the skin a specific treatment;

body hygiene compositions chosen from deodorants, antiperspirant products, and hair-removing compositions;

makeup products for bodily and/or facial skin and/or the hair chosen from foundations, optionally having care properties, blushers, makeup rouges, eyeshadows, concealer products, eyeliners;

lip makeup products, optionally with care properties, lip gloss;

lip pencils;

makeup products for the integuments; and

temporary tattoo products for bodily skin.

66. A cosmetic treatment process for making up, caring for, cleansing, and/or coloring keratin materials comprising applying to the materials at least one cosmetic and/or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one (co)polymer comprising:

(a) a polymer backbone -POL- comprising at least two repeating units,

(b) at least one junction group (A) bonded to the polymer backbone and capable of establishing H bonds with at least one partner junction group, of identical or different chemical nature, each pairing of a junction group involving at least 3 H bonds,

wherein the at least one (co)polymer comprises at least one ionizable group.

67. A process for improving both the persistence of at least one effect provided after deposition by a cosmetic composition and the adhesion of the composition applied to keratin materials, and for allowing rapid, total, and selective removal of the deposit, comprising adding to the composition an effective amount of at least one (co)polymer comprising:

(a) a polymer backbone -POL- comprising at least two repeating units,

(b) at least one junction group (A) bonded to the polymer backbone and capable of establishing H bonds with at least one partner junction group, of identical or different chemical nature, each pairing of a junction group involving at least 3 H bonds,

wherein the at least one (co)polymer comprises at least one ionizable group.