Silicone (meth)acrylate particles, processes for their preparation and use thereof

Patent metadata

Field	Value
Publication number	US-9725538-B2
Application number	US-201414572212-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Dec 19, 2013
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

Particles obtainable by polymerization of a siloxane which has at least one (meth)acrylate group of the formula (I)

—O—C(O)—CR═CH 2   (I)

where R=—H or —CH 3 , which are characterized in that the siloxane has an average molar ratio of groups of the formula (I) to Si atoms of less than 0.1 are provided.

First claim

The invention claimed is:

1. A process for producing silicone (meth)acrylate particles, said process comprising:
a) producing an emulsion of an aqueous phase and an organic phase, wherein the organic phase has at least one radical initiator and at least one siloxane having at least one (meth)acrylate group of formula (I)
—O—C(O)—CR═CH 2   (I)

where R=—H or —CH 3 ,
with the addition of at least one solid-body emulsifier and mixing of the two phases,
where the organic phase forms an inner phase of the emulsion, and

b) fully polymerizing the inner phase of the emulsion in the presence of a radical initiator which is more soluble in the organic phase than in the aqueous phase,
wherein the at least one siloxane has an average molar ratio of groups of formula (I) to Si atoms of less than 0.1;

wherein the at least one siloxane is a compound of formula (II):

wherein
R 1 is a methyl radical;
R 2 is independently selected, for each occurrence in Formula (II), from radicals having the formula —(CH 2 ) 3 —O—CH 2 —CH(OH)—CH 2 —O—C(O)—CH 3 ;
R 3 is independently selected, for each occurrence in Formula (II), from a methyl radical or radicals that have a group according to formula (I);
R′ is independently selected from groups according to formula (I);
a=9 to 250;
b=0 to 20;
c=0 to 20;
and with the proviso that, per siloxane of formula (II), if c=0, at least one radical R 3 is present which has a group according to formula (I).

2. The process according to claim 1 , wherein the radical initiator is added in a concentration of 0.05 to 2% by weight, based on the inner phase of the emulsion.

3. The process according to claim 1 , wherein the solid-body emulsifier has an average particle size d 50 of >100 nm to 200 nm.

4. The process according to claim 1 , wherein the solid-body emulsifiers are selected from metal oxides, mixed oxides, nitrides, hydroxides, carbonates and silicates which are at least (partially)hydrophobicized with at least one compound selected from the group consisting of silanes, siloxanes, quaternary ammonium compounds, cationic polymers and fatty acids or anions thereof.

5. The process according to claim 1 , wherein the at least siloxane having at least one (meth)acrylate group of formula (I) contains said group in the form of a radical selected from at least one of

where R 4 is hydrogen or a methyl group.

6. The process according to claim 5 , wherein the radical is selected formulae (Ib) and (Ie).

7. The process according to claim 1 , wherein the variable a is from 50 to 220.

8. The process according to claim 1 , wherein the variable c is a value from 4 to 12, or c=0 and all of the radicals R 3 are those radicals which have a group according to formula (I).

9. The process according to claim 1 , wherein the organic phase contains substances which can be released from the silicone (methacrylate) particles, wherein said substances which can be released are selected from cosmetic oils, fragrances, silver and silver-containing compounds, dyes, and preservatives.

10. A composition of matter comprising the particles according to claim 1 .

11. The composition of matter according to claim 10 , wherein the particles are dispersed in an aqueous or an organic media.

12. The process according to claim 1 , wherein the at least one siloxane has an average molar ratio of groups of formula (I) to Si atoms of 0.02 to 0.08.

Assignees

• Evonik Industries Ag
• Evonik Degussa Gmbh

Inventors

• Klostermann Michael
• Wiechers Susann
• Naumann Matthias
• Venzmer Joachim

Classifications

• A61Q19/00 Primary

  Preparations for care of the skin · CPC title

• A61K8/891

  saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C08K3/36

  Silica · CPC title