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US 12,421,342 B2Granted
Crosslinkable reactive silicone organic copolymers dispersions
AssigneeWacker Chemie AG
InventorsAmitabha Mitra, Sarah Burke, Daniel Calimente, Daniel Hwang, Frank Sandmeyer
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Abstract
An aqueous dispersion along with methods for producing and uses for the same. Where the aqueous dispersion includes crosslinkable reactive silicone organic copolymers of ethylenically unsaturated monomers and of ethylenically functionalized silicone polymers and is obtainable by means of radically initiated miniemulsion polymerization in an aqueous medium.
Claims19
An aqueous dispersion, comprising:
- wherein the aqueous dispersion is a dispersion of crosslinkable reactive silicone organic copolymers of ethylenically unsaturated monomers and of ethylenically functionalized silicone polymers, obtainable by means of radically initiated miniemulsion polymerization in an aqueous medium of
- (A) one or more ethylenically unsaturated organic monomers, or monomers selected from the group consisting of vinyl esters, (meth)acrylic esters, vinylaromatics, olefins, 1,3-dienes, vinyl ethers, and vinyl halides,
- in the presence of
- (B) at least one silicone polymer, or a silicone resin, which is functionalized with ethylenically unsaturated, radically polymerizable groups and consists of siloxane units of the general formula
- [R1p(OR2)zSiO(4-p-z)/2] (1),
- wherein R1 is identical or different at each occurrence and is a radical R* or E;
- wherein R* is identical or different at each occurrence and is a hydrogen atom or is a hydrocarbon radical which is free from aliphatic multiple C—C bonds, has 1 to 18 carbon atoms, and may optionally be substituted;
- and
- wherein E is an ethylenically unsaturated radical of the formula —(CR52)m—X;
- wherein m is an integer from 1 to 10;
- wherein R5 is a hydrogen atom, a C1-C12 alkyl radical or a C6-C18 aryl radical;
- and
- wherein X is an ethylenically unsaturated organic group;
- wherein R 1 is an ethylenically unsaturated radical E in at least 1 mol % and at most 50 mol % of all siloxane units (I);
- wherein R2 is identical or different at each occurrence and is a hydrogen atom or a hydrocarbon radical having 1 to 18 carbon atoms;
- wherein p is 0, 1, 2 or 3;
- wherein z is 0, 1, 2 or 3;
- wherein the sum p+z has a value of 0, 1, 2 or 3 and for at least 20 mol % of all siloxane units of the formula (1) in the silicone polymer (B), the sum p+z is 1 or 0, with p being 1 or 0 and z being 0;
- and in the presence of
- (C) at least one compound which have an ethylenically unsaturated radical and at least one additional functional group which is not free radically polymerized but capable for crosslinking, in an amount of 10 to 50% by weight based on the total weight of (A);
- wherein the miniemulsion polymerization being carried out by preparation in the first step of a solution of at least one silicone polymer (B) in one or more ethylenically unsaturated monomers (A), to give a silicone-in-monomer solution;
- wherein emulsification in the second step of the resulting silicone-in-monomer solution, using emulsifiers, optionally hydrophobic coemulsifiers, and optionally polymerization inhibitors which prevent premature radical emulsion polymerization, in water in such a way as to give a miniemulsion having particle size D (50) of not more than 350 nm;
- wherein the compound (C) is added in the first step during the preparation of the silicone-in-monomer solution or in the second step during the emulsification to form the miniemulsion;
- wherein subjection in the third step of the resulting miniemulsion to radical emulsion polymerization;
- and
- wherein the miniemulsion polymerization is carried out using water-soluble or oil-soluble, or a mixture of water-soluble and oil-soluble, polymerization initiators.
23 more elements
A method for producing an aqueous dispersion of crosslinkable reactive silicone organic copolymers of ethylenically unsaturated monomers and of ethylenically functionalized silicone polymers, comprising the steps of:
- radically initiating a miniemulsion polymerization in an aqueous medium of
- (A) one or more ethylenically unsaturated organic monomers, or monomers selected from the group consisting of vinyl esters, (meth)acrylic esters, vinylaromatics, olefins, 1,3-dienes, vinyl ethers, and vinyl halides,
- in the presence of
- (B) at least one silicone polymer, or a silicone resin, which is functionalized with ethylenically unsaturated, radically polymerizable groups and consists of siloxane units of the general formula
- [R1p(OR2)zSiO(4-p-z)/2] (I),
- where R1 is identical or different at each occurrence and is a radical R* or E;
- wherein R* is identical or different at each occurrence and is a hydrogen atom or is a hydrocarbon radical which is free from aliphatic multiple C—C bonds, has 1 to 18 carbon atoms, and may optionally be substituted;
- and
- wherein E is an ethylenically unsaturated radical of the formula-(CR52)m—X;
- wherein m is an integer from 1 to 10, preferably 3;
- wherein R5 is a hydrogen atom, a C1-C12 alkyl radical or a C6-C18 aryl radical;
- and
- wherein X is an ethylenically unsaturated organic group;
- wherein R2 is identical or different at each occurrence and is a hydrogen atom or a hydrocarbon radical having 1 to 18 carbon atoms;
- wherein R1 is an ethylenically unsaturated radical E in at least 1 mol % and at most 50 mol % of all siloxane units (I);
- wherein p is 0, 1, 2 or 3;
- wherein z is 0, 1, 2 or 3;
- wherein the sum p+z has a value of 0, 1, 2 or 3;
- and
- wherein for at least 20 mol % of all siloxane units of the formula (I) in the silicone resin (B), the sum p+z is 1 or 0, with p being 1 or 0 and z being 0;
- and in the presence of
- (C) at least one compound which have an ethylenically unsaturated radical and at least one additional functional group which is not free radically polymerized but capable for crosslinking, in an amount of 10 to 50% by weight based on the total weight of (A);
- wherein the miniemulsion polymerization being carried out by preparation in a first step of a solution of at least one silicone polymer (B) in one or more ethylenically unsaturated monomers (A), to give a silicone-in-monomer solution;
- wherein emulsification in a second step of the resulting silicone-in-monomer solution, using emulsifiers, optionally hydrophobic coemulsifiers, and optionally polymerization inhibitors which prevent premature radical emulsion polymerization, in water in such a way as to give a miniemulsion having a particle size D (50) of not more than 350 nm, with the proviso that compound (C) is added in the first step during the preparation of the silicone-in-monomer solution or in the second step during the emulsification to form the miniemulsion;
- wherein subjection in a third step of the resulting miniemulsion to radical emulsion polymerization;
- and
- wherein the miniemulsion polymerization is carried out using water-soluble or oil-soluble, or a mixture of water-soluble and oil-soluble, polymerization initiators.
24 more elements
Dependencies are inferred from the claim text.