Aqueous silicone polymer emulsion

Patent metadata

Field	Value
Publication number	US-11292906-B2
Application number	US-201816758291-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Oct 23, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

Aqueous silicone polymer emulsion The presently claimed invention relates to a composition in form of an emulsion of water incompatible silicone oil comprising droplets of silicone oil dispersed in a continuous aqueous phase. The composition provides better slip and mar resistance, anti-blocking properties and optical properties to the coating formulations, printing ink, personal care product compositions, textiles, leather and indirect food contact applications.

First claim

The invention claimed is:

1. A composition in form of an emulsion containing comprising a continuous phase and a dispersed phase comprising:
a) at least one block copolymer comprising a block A derived from at least one unsaturated monomer selected from the group consisting of (meth)acrylates and a block B derived from at least one unsaturated monomer selected from the group consisting of (meth)acrylic acids, obtained in a controlled radical polymerization process,
b) at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group, and
c) water,
wherein water is the continuous phase and the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group is the dispersed phase in the form of emulsion droplets.

2. The composition according to claim 1 , wherein a weight ratio of (meth)acrylate monomer to (meth)acrylic acid monomer is 1:10 to 10:1.

3. The composition according to claim 1 , wherein the (meth)acrylate monomer is selected from the group consisting of esters of (meth)acrylic acid with C 1 -C 30 alkanols, C 1 -C 20 alkyl phenols, C 5 -C 20 cycloalkanols, phenyl-C 1 -C 4 alkanols or phenoxy-C 1 -C 4 alkanols.

4. The composition according to claim 1 , wherein the (meth)acrylate monomer is selected from the group consisting of esters of (meth)acrylic acid with C 1 -C 8 alkanols.

5. The composition according to claim 1 , wherein the controlled radical polymerization is selected from nitroxide-mediated controlled polymerization (NMP), atom transfer radical polymerization (ATRP), or reversible addition fragmentation chain transfer polymerization (RAFT).

6. The composition according to claim 5 , wherein the nitroxide-mediated controlled polymerization is carried out by using a polymerization regulator compound which is selected from one of the following formulae (A), (B) and (C) or based on the corresponding stable free nitroxyl radicals in conjunction with a radical source:

wherein
R is hydrogen, C 1 -C 18 alkyl which is uninterrupted or interrupted by one or more oxygen atoms, cyanoethyl, benzoyl, glycidyl, a monovalent radical of an aliphatic carboxylic acid having 2 to 18 carbon atoms, of a cycloaliphatic carboxylic acid having 7 to 15 carbon atoms, or an α,β-unsaturated carboxylic acid having 3 to 5 carbon atoms or of an aromatic carboxylic acid having 7 to 15 carbon atoms;
R 101 is C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, C 7 -C 8 aralkyl, C 2 -C 18 alkanoyl, C 3 -C 5 alkenoyl or benzoyl;
R 102 is C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 2 -C 8 alkenyl, which can be unsubstituted or substituted by a cyano, carbonyl or carbamide group, or is glycidyl, a group of the formula —CH 2 CH(OH)—Z or of the formula —CO—Z or —CONH—Z, wherein Z is hydrogen, methyl or phenyl;
G 6 is hydrogen;
G 5 is hydrogen or C 1 -C 4 ;
G 1 and G 3 are methyl;
G 2 and G 4 are ethyl or propyl, or G 1 and G 2 are methyl and G 3 and G 4 are ethyl or propyl; and
X is selected from CH 2 -phenyl, CH 3 CH-phenyl, (CH 3 ) 2 C-phenyl, (C 5 -C 6 cycloalkyl) 2 CCN, (CH 3 ) 2 CCN,

CH 2 CH═CH 2 , CH 3 CH—CH═CH 2 , (C 1 -C 4 alkyl)CR 20 —C(O)-phenyl, (C 1 -C 4 )alkyl-CR 20 —C(O)—(C 1 -C 4 )alkoxy, (C 1 -C 4 )alkyl-CR 20 —C(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-CR 20 —C(O)—N-di(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-CR 20 —C(O)—NH(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-CR 20 —C(O)—NH 2 , wherein R 20 is hydrogen or (C 1 -C 4 alkyl); and
wherein any of the alkyl groups can be unsubstituted or substituted by one or more functional groups selected from the group consisting of hydroxyl, amino, carboxylic acid, halide, cyano, and carbonyl.

7. The composition according to claim 1 , wherein the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group has a viscosity in the range from ≥0.1 m 2 /sec to ≤30000 m 2 /sec at a temperature of 20° C., according to DIN 53019.

8. The composition according to claim 1 , wherein the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group has a viscosity in the range from ≥1000 m 2 /sec to ≤30000 m 2 /sec at a temperature of 20° C., according to DIN 53019.

9. The composition according to claim 1 , wherein the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group is a polydimethylsiloxane comprising at least 90% by weight of dimethylsilyloxy groups, based on total weight of the non-polymerizable, non-polar silicone oil.

10. The composition according to claim 1 , wherein the emulsion droplets have an average size Dv 50 in the range from ≥10 nm to ≤10000 nm determined according to dynamic light scattering technique with a fixed scattering angle of 90° or 180°.

11. The composition according to claim 1 , wherein the emulsion comprises a micelle having an average size Dv 50 in the range from ≥10 nm to ≤100 nm determined according to dynamic light scattering technique with a fixed scattering angle of 90° or 180°.

12. The composition according to claim 1 , wherein the at least one block copolymer has a polydispersity index (PDI) in the range from ≥1.1 to ≤1.8 determined according to gel permeation chromatography with polystyrene standards.

13. The composition according to claim 1 , wherein the composition comprises:
a) at least one block copolymer comprising a block A derived from at least one unsaturated monomer selected from the group consisting of esters of (meth)acrylic acid with C 1 -C 30 alkanols, C 1 -C 20 alkyl phenols, C 5 -C 20 cycloalkanols, phenyl-C 1 -C 4 alkanols or phenoxy-C 1 -C 4 alkanols and a block B derived from at least one unsaturated monomer selected from the group consisting of (meth)acrylic acids, obtained in a controlled radical polymerization process,
b) at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group having a viscosity in the range from ≥0.1 m 2 /sec to ≤30000 m 2 /sec, at a temperature of 20° C., according to DIN 53019, and
c) water,
wherein water is the continuous phase and the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group is the dispersed phase in the form of emulsion droplets having an average size Dv 50 in the range from ≥10 nm to ≤10000 nm determined according to dynamic light scattering technique with a fixed scattering angle of 90° or 180°.

14. The composition according to claim 1 , wherein
an amount of the at least one block copolymer is in the range from ≥0.1 wt-% to ≤10 wt.-% by weight, based upon the total weight of the composition,
an amount of the at least one non-polymerizable, non-polar silicone oil having at least one poly(dimethylsilyloxy)-group is in the range from ≥0.1 wt.-% to ≤70 wt.-% by weight, based upon the total weight of the composition, and
an amount of water is in the range from ≥20 wt.-% to ≤98.8 wt.-% by weight, based upon the total weight of the composition.

15. The composition according to claim 1 , wherein the composition comprises:
a) ≥0.1 wt.-% to ≤10 wt.-% by weight of at least one block copolymer comprising a block A derived from at least one unsaturated monomer selected from the group consisting of esters of (meth)acrylic acid with C 1 -C 30 alkanols and a block B derived from (meth)acrylic acid, obt

Assignees

• Basf Se

Inventors

• Gernandt Andreas
• Auschra Clemens
• Knischka Ralf

Classifications

• C08L53/00 Primary

  Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C08F2438/02

  Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO] · CPC title

• C08K5/3432

  Six-membered rings · CPC title