Use of copolymers based on acrylamidoalkylsulfonic acids as thickeners in preparations comprising organic solvents

• US 6,696,517 B2
• Filed: 04/16/2002
• Issued: 02/24/2004
• Est. Priority Date: 04/20/2001
• Status: Expired due to Term

• Current Assignee: Clariant Produkte Deutschland GmbH (Clariant AG)
• Original Assignee: Clariant GmbH (Clariant AG)
• Inventors: Klug, Peter, Morschhäuser, Roman, Löffler, Matthias
• Primary Examiner(s): Wu, David W.
• Assistant Examiner(s): Sastri, Satya B
• Application Number:
  US10/123,450
• Publication Number:
  US 20030004241A1
• Time in Patent Office: 679 Days
• Field of Search: 524/555, 524/548, 524/543, 524/552, 524/700, 524/726, 524/808, 524/812, 524/817
• US Class Current: 524/555
• CPC Class Codes: C08F 220/585 and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]

Abstract

The invention relates to the use of copolymers consisting essentially of

a1) 1 to 50% by weight of the repeat structural unit of the formula (1):

 where n is an integer from 2 to 9 or

a2) 1 to 50% by weight of a mixture of the repeat structural unit of the formula (1) and of the repeat structural unit of the formula (2):

 where R, R¹ and R² may be identical or different and are hydrogen or a linear or branched alkyl or alkenyl group having in each case 1 to 30 carbon atoms, and

b) 49.99 to 98.99% by weight of the repeat structural unit of the formula (3):

 in which R³ is hydrogen, methyl or ethyl, Z is (C₁-C₈)-alkylene and X is an ammonium, alkali metal or alkaline earth metal ion and

c) 0.01 to 8% by weight of crosslinking structures which originate from monomers having at least two olefinic double bonds, as thickeners in preparations comprising organic solvents.

Claims

1. A process for thickening a preparation comprising an organic solvent said process comprising adding to the preparation of at least one copolymer, consisting essentially of

a1) 1 to 50% by weight of the repeat structural unit of the formula (1 ):

 

where n is an integer from 2 to 9 or

a2) 1 to 50% by weight of a mixture of the repeat structural unit of the formula (1) and of the repeat structural unit of the formula (2);

 

where R, R¹ and R² may be identical or different and are hydrogen or a linear or branched alkyl or alkenyl group having in each case 1 to 30 carbon atoms, and

b) 49.99 to 98.99% by weight of the repeat structural unit of the formula (3);

 

in which R³ is hydrogen, methyl or ethyl, Z is (C₁-C₈)-alkylene and X is an ammonium, alkali metal or alkaline earth metal ion and

c) 0.01 to 8% by weight of a crosslinking structure which originates from monomers having at least two olefinic double bonds, wherein

the structural unit of c) is derived from the group consisting of allyl acrylate, allyl methacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, and mixtures thereof.

2. The process of claim 1, wherein the copolymers comprise 2 to 30% by weight of the structural units a1) or a2), 69.5 to 97.5% by weight of the structural unit b) and 0.01 to 5% by weight of the structural unit c).

3. The process of claim 1, wherein the copolymers comprise the structural unit a2).

4. The process of claim 1, wherein the structural unit according to formula (1) is derived from N-vinylpyrrolidone.

5. The process of claim 1, wherein the structural unit according to formula (3) is derived from 2-acrylamido-2-methylpropanesulfonic acid or an ammonium salt thereof.

6. The process of claim 1, wherein the copolymers are prepared by precipitation polymerization in tert-butanol.

7. The process of claim 1, wherein the preparation comprises 0.1 to 5% by weight of copolymers, based on a finished preparation.

8. A process for thickening a preparation comprising an organic solvent said process comprising adding to the preparation of at least one copolymer, consisting essentially of

a1) 1 to 50% by weight of the repeat structural unit of the formula (1):

 

where n is an integer from 2 to 9 or

a2) 1 to 50% by weight of a mixture of the repeat structural unit of the formula (1) and of the repeat structural unit of the formula (2);

 

where R, R¹ and R² may be identical or different and are hydrogen or a linear or branched alkyl or alkenyl group having in each case 1 to 30 carbon atoms, and

b) 49.99 to 98.99% by weight of the repeat structural unit of the formula (3);

 

in which R³ is hydrogen, methyl or ethyl, Z is (C₁-C₈)-alkylene and X is an ammonium, alkali metal or alkaline earth metal ion and

c) 0.01 to 8% by weight of a crosslinking structure which originates from monomers having at least two olefinic double bonds and,

wherein the organic solvent comprises a polar-aprotic solvent.

9. The process of claim 8, wherein the organic solvent is selected from the group consisting of monohydric alcohols, polyhydric alcohols, ketones, esters, ethers, amides, sulfoxides, nitriles, O—

, N—

and S-heterocycles, ethoxylated alcohols, propoxylated alcohols polyethylene glycols, and mixtures thereof.

10. The process of claim 9, wherein the organic solvent is selected from the group consisting of methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, t-butanol, glycerol, propylene glycol, butylene glycol, glycol, acetone, acetonitrile, tetrahydrofuran, dimethylformamide, and mixtures thereof.

11. The process of claim 8, wherein the preparation comprises 5 to 99.9% by weight of organic solvent, based on a finished preparation.

12. The process of claim 8, wherein the preparation comprises 40 to 95% by weight of the organic solvent based on a finished preparation.

13. The process of claim 8, wherein the preparation comprises 5 to 30% by weight of organic solvent, based on a finished preparation and the finished preparation has a pH ranging from 3 to 6.

14. The process of claim 8, wherein the preparation further comprises 30 to 80% by weight of water, based on the finished preparation.

15. The process of claim 8, wherein the preparation has a pH of from 4 to 9.

16. The process of claim 8, wherein the preparation is selected from the group consisting of cosmetic, dermatological, and pharmaceutical preparations.

17. A method of thickening preparations comprising organic solvents, which comprises adding to the preparations at least one copolymer consisting essentially of

a1) 1 to 50% by weight of the repeat structural unit of the formula (1):

 

where n is an integer from 2 to 9 or

a2) 1 to 50% by weight of a mixture of the repeat structural unit of the formula (1) and of the repeat structural unit of the formula (2);

 

where R, R¹ and R² may be identical or different and are hydrogen or a linear or branched alkyl or alkenyl group having in each case 1 to 30 carbon atoms, and

b) 49.99 to 98.99% by weight of the repeat structural unit of the formula (3);

 

in which R³ is hydrogen, methyl or ethyl, Z is (C₁-C₈)-alkylene and X is an ammonium, alkali metal or alkaline earth metal ion and

c) 0.01 to 8% by weight of crosslinking structures which originate from monomers having at least two olefinic double bonds said crosslinking structures selected from the group consisting of allyl acrylate, allyl methacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, and mixtures thereof wherein the organic solvents comprise a water-miscible polar-aprotic solvent.