Water-soluble or water-swellable crosslinked copolymers

• US 6,683,144 B2
• Filed: 06/21/2002
• Issued: 01/27/2004
• Est. Priority Date: 01/11/2000
• Status: Expired due to Term

• Current Assignee: Clariant Produkte Deutschland GmbH (Clariant AG)
• Original Assignee: Clariant GmbH (Clariant AG)
• Inventors: Morschhäuser, Roman, Löffler, Matthias
• Primary Examiner(s): Lipman, Bernard
• Application Number:
  US10/177,704
• Publication Number:
  US 20020193544A1
• Time in Patent Office: 585 Days
• Field of Search: 526/264
• US Class Current: 526/264
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 8/8182 Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08F 220/585 and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]

Abstract

Water-soluble or water-swellable crosslinked copolymers consisting essentially of structural units of the formula 1

or a mixture of the structural units of the formula 1 with structural units of the formula 2

and structural units of the formula 3

where R, R¹, R², R³, Z and n are as defined in the description. These copolymers are crosslinked with compounds which contain at least two olefinic double bonds. These crosslinked copolymers are suitable as thickeners, in particular for cosmetic and pharmaceutical preparations.

Claims

1. A process for the preparation of a water-soluble or water-swellable crosslinked copolymer consisting essentially of

a) 1 to 50% by weight of a repeating structural unit of formula (1)

where n is an integer from 2 to 9,

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

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

c) 0.01 to 8% by weight of crosslinking structures resulting from monomers having at least two olefinic double bonds selected from the group consisting of allyl acrylate, allyl methacrylate, allyl ethyl methacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, tetraallyloxyethane, tetraethylene glycol diacrylate, triallylamine, trimethylolpropane diallyl ether, methylene bisacrylamide, divinylbenzene, and mixtures thereof,

said process comprising dissolving or dispersing the monomers corresponding to the repeating structural units of formulae 1 and 3 in a protic solvent, adding one or more the crosslinking structures of c) starting the polymerization by adding a free-radical—

forming compound.

2. A method for using the water-soluble or water swellable copolymer as in claimed in claim 1, comprising incorporating said copolymer as a thickner in a cosmetic or pharmaceutical preparation.

4. The copolymer as claimed in claim 1, consisting essentially of 2 to 30% by weight of the repeating structural unit of the formula 1 or a mixture of the repeating structural units of the formulae 1 and 2, 69.5 to 97.5% by weight of the repeating structural unit of the formula 3 and 0.2 to 3% by weight of crosslinking structures resulting from monomers having at least two olefinic double bonds.

5. The copolymer as claimed in claim 1, consisting essentially of 3 to 15% by weight of the repeating structural unit of the formula 1 or a mixture of the repeating structural units of the formulae 1 and 2, 84.5 to 96.5% by weight of the repeating structural unit of the formula 3 and 0.5 to 2% by weight of crosslinking structures resulting from monomers having at least two olefinic double bonds.

6. The copolymer as claimed in claim 1, comprising crosslinking structures resulting from allyl (meth)acrylate.

8. A method of using the water-soluble or water-swellable copolymer as claimed in claim 1, comprising incorporating said copolymer as a thickener in a cosmetic or pharmaceutical preparation.

9. A cosmetic or pharmaceutical preparation comprising a water-soluble or water-swellable copolymer as claimed in claim 1.

3. A cosmetic preparation or a pharmaceutical preparation comprising a water-soluble or water-swellable crosslinked copolymer consisting essentially of

a) 1 to 50% by weight of the repeating structural unit of the formula (1)

where n is an integer from 2 to 9,

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

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

c) 0.01 8% by weight of crosslinking structures resulting from monomers having at least two olefinic double bonds selected from the group consisting of allyl acrylate, allyl methacrylate, allyl ethyl methacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, tetraallyloxyethane, tetraethylene glycol diacrylate, triallylamine, trimethylolpropane diallyl ether, methylene bisacrylamide, divinylbenzene, and mixtures thereof.

7. A process for the preparation of a water-soluble or water-swellable copolymer consisting essentially of:

a1) 1 to 50% by weight of a repeating structural unit of formula (1)

where n is an integer from 2 to 9,

or

a2) 1 to 50% by weight of a mixture of the repeating structural unit of the formula (1) and of a repeating structural unit of 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 a repeating structural unit of formula (3)

in which R³ is hydrogen, methyl or ethyl, Z is C₁-C₈-alkylene, n is an integer from 2 to 9, and X is an ammonium, alkali metal or alkaline earth metal ion, and

c) 0.01 to 8% by weight of crosslinking structures resulting from monomers having at least two olefinic double bonds;

said process comprising dissolving or dispersing the monomers corresponding to the repeating structural units of the formulae 1, 2 and 3 in a protic solvent, adding one or more crosslinkers having at least two olefinic double bonds to this solution or dispersion, and starting the polymerization by adding a free-radical-forming compound.