Cationic Comb Copolymers, Preparation Thereof And Use Thereof In Cosmetic, Pharmaceutical And Dermatological Formulations

• US 20120114571A1
• Filed: 03/27/2010
• Published: 05/10/2012
• Est. Priority Date: 04/01/2009
• Status: Abandoned Application

• Current Assignee: Clariant International AG (Clariant AG)
• Original Assignee: Clariant Finance (Bvi) Limited
• Inventors: Klug, Peter, Loeffler, Matthias, Mildner, Carina, Lo Vasco, Sebastiano, Lindner, Thomas, Fischer, Dirk, Kunze, Matthias, Cerny, Tomas
• Application Number:
  US13/262,382
• Publication Number:
  US 20120114571A1
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 8/81 obtained by reactions involving only carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61K 8/86 Polyethers
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: A61Q 90/00 Cosmetics or similar toiletry preparations for specific uses not provided for in other groups of this subclass
• CPC Class Codes: C08F 20/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate
• CPC Class Codes: C08F 20/60 containing nitrogen in addition to the carbonamido nitrogen
• CPC Class Codes: C08F 220/1818 C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
• CPC Class Codes: C08F 220/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate

Abstract

Copolymers are described, containing a) 20.0-99.9% by weight of one or more structural units resulting from polymerizable substances of the following structural formula (I) in which R² is a linear or branched saturated alkyl radical having 6 to 200 carbon atoms or a linear or branched, mono- or, polyunsaturated alkenyl radical having 6 to 200 carbon atoms, and R¹, Y, n and m are each as defined in claim 1, b) 0.1-20.0% by weight of one or more structural units resulting from polymerizable quaternary ammonium compounds, and c) 0-60.0% by weight of one or more nonionic structural units resulting from one or more further polymerizable substances. The copolymers are advantageously suitable, for example, for the production of cosmetic, dermatological or pharmaceutical formulations.

Claims

1. A copolymer comprising

a) 60.0%-99.9% by weight of at least one structure unit originating from at least one polymerizable substance of formula (I)

2. A copolymer as claimed in claim 1, comprising 60.0% to 99.9% by weight of at least one structural unit of component a) originating from at least one polymerizable substance of formula (I)

3. A copolymer as claimed in claim 1, comprising 60.0% to 99.9% by weight of at least one structural unit of component a) originating from at least one polymerizable compound selected from the group consisting of structural formulae (Ia) and (Ib)

4. A copolymer as claimed in claim 3, wherein the at least one compound of the formula (Ia) is selected from the group consisting of lauryl acrylate, lauryl methacrylate, hexadecyl acrylate, hexadecyl methacrylate, stearyl acrylate, stearyl methacrylate, isostearyl acrylate, isostearyl methacrylate, octyldodecyl acrylate, octyldodecyl methacrylate, behenyl acrylate and behenyl methacrylate, and the at least one compound of the formula (Ib) is selected from the group consisting of acrylic ester of lauryl alcohol with 7 EO units, methacrylic ester of lauryl alcohol with 7 EO units, acrylic ester of talyl alcohol with 8 EO units, methacrylic ester of talyl alcohol with 8 EO units, acrylic ester of talyl alcohol with 25 EO units, methacrylic ester of talyl alcohol with 25 EO units, acrylic ester of behenyl alcohol with 25 EO units, and methacrylic ester of behenyl alcohol with 25 EO units.

5. A copolymer as claimed in claim 3, wherein R² in the at least one compound of the formula (I) or in the at least one compound of the formulae (Ia) and (Ib) is a linear or branched, saturated alkyl radical having 12 to 200 carbon atoms.

6. A copolymer as claimed in claim 1, wherein the at least one structural unit of component b) originates from at least one substance selected from the group consisting of

b1) at least one polymerizable quaternary ammonium compound of the following structural formula (II)

X⁻

+NR⁷R⁸R⁹R¹⁰ 

 

(II)

wherein

X⁻

is a negatively charged counterion.

R⁷ is vinyl radical, allyl radical or a radical of the following structural formula (III)

7. A copolymer as claimed in claim 6, wherein the negatively charged counterion X⁻

in formula (II) and (IV) is selected from the ou consistin of chloride, bromide, iodide, ½

SO₄²⁻

and methosulfate.

8. A copolymer as claimed in claim 1, wherein the at least one structural unit of component b) originates from at least one polymerizable quaternary ammonium compound selected from the group consisting of diallyldimethylammonium chloride (DADMAC), [2-(methacryloyloxy)ethyl]trimethylammonium chloride (MAOETAC), [2-(acryloyloxy)ethyl]trimethylammonium chloride (AOETAC), [2-methacrylamidoethyl]trimethylammonium chloride, [2-(acrylamido)ethyl]trimethylammonium chloride, [3-methacrylamidopropyl]trimethylammonium chloride (MAPTAC), [3-acrylamidopropyl]trimethylammonium chloride (APTAC), N-methyl-2-vinylpyridinium chloride, N-methyl-4-vinylpyridinium chloride, and N-methyl-3-vinylimidazolinium chloride.

9. A copolymer as claimed in claim 6, wherein the at least one the structural unit of component b) originates from at least one polymerizable quaternary ammonium compound of formula (II).

10. A copolymer as claimed in claim 1, comprising at least one structural unit of component c) that originates from substances selected from the group consisting of monomers having more than one polymerizable group, which may have a crosslinking effect.

11. A copolymer as claimed in claim 1, wherein the at least one structural unit of component c) originates from substances selected from the group consisting of divinylbenzene, methylenebisacrylamide (MBA), triallylamine, triallyl cyanurate, ethanediol diacrylate, ethanediol dimethacrylate (EDDMA), buanediol diacrylate, buanediol dimethacrylate (BDDMA), hexanediol diacrylate, hexanediol dimethacrylate (HDDMA), clodecanediol diacrylate, dodecanediol dimethacrylate (DDDMA), trimethylolpropane triacrylate (TMPTA), trimethylolpropane trimethacrylate (TMPTMA), glycerol diacrylate, glycerol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate with molar masses between 400 and 800 g/mol, polyethylene glycol dimethacrylate with molar masses between 400 and 800 g/mol, allyl acrylate, methacrylate or ethacrylate, preferably allyl acrylate or methacrylate, and more particularly allyl methacrylate (AMA), dipropylene glycol diallyl ether, polyglycol diallyl ether, hydroquinone diallyl ether, trimethylolpropane diallyl ether, trimethylolpropane triallyl ether, tetraallyloxyethane, triethylene glycol divinyl ether, other allyl ethers or vinyl ethers of polyfunctional alcohols, and mixtures thereof.

12. A copolymer as claimed in claim 1, wherein the amount of structural units of component a) is from 60.0% to 99.5% by weight, the amount of structural units of component b) is from 0.5% to 20.0% by weight, and the amount of structural units of component c) is from 0% to 20.0% by weight.

13. A copolymer as claimed in claim 1, wherein the amount of structural units of component a) is from 80.0% to 98.0% by weight, the amount of structural units of component b) is from 0.7% to 11.0% by weight, and the amount of structural units of component c) is from 0% to 11.0% by weight.

14. A copolymer as claimed in claim 3, wherein the weight ratio of structural units originating from the compounds of the formula (Ia) to structural units originating from the compounds of the formula (Ib) in the copolymer is 1.0:

0 to 0.8.

15. A copolymer as claimed in claim 1, comprising no structural units originating from anionic polymerizable substances.

16. A copolymer as claimed in claim 1, consisting of components a) and b).

17. A copolymer as claimed in claim 1, consisting of components a), b), and c).

18. A copolymer as claimed in claim 17, wherein the structural units of component c) are selected from crosslinking structural units.

19. A process for preparing a copolymer as claimed in claim 1, comprising the step of radically polymerizing the monomers.

20. A cosmetic, pharmaceutical or dermatological formulation comprising at least one copolymer as claimed in claim 1.

21. A process for thickening oil comprising the step of adding at least one copolymer as claimed in claim 1 to an oil.

22. A process for conditioning fibers comprising the step of contacting the fibers with at least one copolymer as claimed in claim 1.

23. A process for increasing the water resistance of sun protection formulations comprising the step of adding at least one copolymer as claimed in claim 1 to the sun protection formulation.

24. A process for increasing the sun protection factor of sun protection formulations comprising the step of adding at least one copolymer as claimed in claim 1 to the sun protection formulation.

25. An emulsifier comprising at least one copolymer as claimed in claim 1.