Polysiloxanes as anti-adhesive and dirt-repellant additives, method for the production and use thereof

Patent metadata

Field	Value
Publication number	US-9938432-B2
Application number	US-201515521812-A
Country	US
Kind code	B2
Filing date	Nov 20, 2015
Priority date	Nov 20, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The invention relates to polysiloxanes which can be obtained by adding at least one monovinyl functional polysiloxane and at least one epoxy functional, monovinyl functional component to a Si—H functional polysiloxane. The invention also relates to the production of polysiloxanes, to compositions containing said polysiloxanes, to the use of the compositions in a coating method and to substrates coated with the composition and to the use of the polysiloxanes as additives for finishing surfaces of hardened compositions with anti-adhesive properties.

First claim

The invention claimed is:

1. A polysiloxane obtained by the addition of at least one monovinyl-functional polysiloxane and at least one epoxy-functional, monovinyl-functional component onto an Si—H-functional polysiloxane, characterized in that the Si—H-functional polysiloxane is catenated, and the at least one monovinyl-functional polysiloxane possesses the formula (I):

in which
Z is hydrogen or an alkyl group having 1 to 4 carbon atoms, and
X is a monovalent radical of the following formula:

in which p=0 or 1, q=0 to 30, and r=1 to 400, and, if p=1, q 2,
R a is a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms, or an alkoxyalkylene oxide-alkyl radical or alkoxypolyalkylene oxide-alkyl radical,
all R b , R c , R d , and R e independently of one another are a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms,
R d and R e additionally, independently of one another, may be R a [SiR b R e O] r , in which
R a , R b , R c , and r are as defined above and are selected independently thereof.

2. The polysiloxane as claimed in claim 1 , characterized in that the at least one epoxy-functional, monovinyl-functional component possesses the formula (II):

in which
Z is hydrogen or an alkyl group having 1 to 4 carbon atoms and
Y is a monovalent radical of the following formula:
-L-Epoxy

in which L is a linking group and Epoxy is an oxirane ring, and where the oxirane ring is bonded by one or both carbon atoms to the linking group L.

3. The polysiloxane as claimed in claim 1 , characterized in that at least one monovinyl-functional component different from the monovinyl-functional polysiloxane and from the epoxy-functional, monovinyl-functional component had been reacted with the Si—H-functional polysiloxane, and this component possesses the formula (III):

in which
Z is hydrogen or an alkyl group having 1 to 4 carbon atoms, and
Q is a monovalent radical of the following formula:
-(L′) v -R

in which v=0 or 1,
L′ is a linking group, and
R is a radical —SiR x n R y 3-n , in which
n=1 to 3,
R x independently at each occurrence is halogen, Oalkyl, or O—CO-alkyl, and
R y is alkyl or is aryl having 6 to 10 carbon atoms; or
R is a polymeric radical having ether, ester and/or urethane groups.

4. A polysiloxane obtained by the addition of at least one monovinyl-functional polysiloxane and at least one epoxy-functional, monovinyl-functional component onto an Si—H-functional polysiloxane, characterized in that the at least one monovinyl-functional polysiloxane possesses the formula (I):

in which
Z is hydrogen or an alkyl group having 1 to 4 carbon atoms, and
X is a monovalent radical of the following formula:

in which p=0 or 1, q=0 to 30, and r=1 to 400, and, if p=1, q≥2,
R a is a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms, or an alkoxyalkylene oxide-alkyl radical or alkoxypolyalkylene oxide-alkyl radical,
all R b , R c , R d , and R e independently of one another are a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms,
R d and R e additionally, independently of one another, may be R a [SiR b R c O] r , in which
R a , R b , R c , and r are as defined above and are selected independently thereof;
wherein at least one monohydroxy-functional polymeric component which contains ether, ester and/or urethane groups had been reacted by condensation reaction with the Si—H-functional polysiloxane before addition reactions of monovinyl-functional components onto the Si—H-functional polysiloxane were carried out.

5. A polysiloxane obtained by the addition of at least one monovinyl-functional polysiloxane and at least one epoxy-functional, monovinyl-functional component onto an Si—H-functional polysiloxane, characterized in that the at least one monovinyl-functional polysiloxane possesses the formula (I):

in which
Z is hydrogen or an alkyl group having 1 to 4 carbon atoms, and
X is a monovalent radical of the following formula:

in which p=0 or 1, q=0 to 30, and r=1 to 400, and, if p=1, q≥2,
R a is a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms, or an alkoxyalkylene oxide-alkyl radical or alkoxypolyalkylene oxide-alkyl radical,
all R b , R c , R d , and R e independently of one another are a linear, halogenated or unhalogenated alkyl radical having 1 to 30 carbon atoms, a branched or cyclic, halogenated or unhalogenated alkyl radical having 3 to 30 carbon atoms, or an aryl radical having 6 to 30 carbon atoms, or an alkylaryl radical or an arylalkyl radical having 7 to 30 carbon atoms,
R d and R e additionally, independently of one another, may be R a [SiR b R c O] r , in which
R a , R b , R c , and r are as defined above and are selected independently thereof;
wherein the polysiloxane is further characterized in that it possesses general formula (IV):

where
Y is a monovalent radical of the following formula:
-L-Epoxy

in which L is a linking group and Epoxy is an oxirane ring, and where the oxirane ring is bonded by one or both carbon atoms to the linking group L;
Q is a monovalent radical of the following formula:
-(L′) v -R

in which v=0 or 1,
L′ is a linking group, and
R is a radical —SiR x n R y 3-n , in which
n=1 to 3,
R x independently at each occurrence is halogen, Oalkyl, or O—CO-alkyl, and
R y is alkyl or is aryl

Assignees

• Byk Chemie Gmbh
• Byk Chemie Gmbh

Inventors

• Jaunky Wojciech
• Griesel Wolfgang

Classifications

• C09D183/10 Primary

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00) · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08G77/458

  containing polyurethane sequences · CPC title

• B32B27/283

  comprising polysiloxanes · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title