Fluorine-containing oligomer, nano-silica composite particles using the same, and methods for producing both

Patent metadata

Field	Value
Publication number	US-9803044-B2
Application number	US-201414773160-A
Country	US
Kind code	B2
Filing date	Mar 6, 2014
Priority date	Mar 6, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Disclosed is a fluorine-containing oligomer comprising a copolymer of a fluoroalkyl alcohol (meth)acrylic acid derivative represented by the general formula:

C n F 2n+1 (CH 2 CF 2 ) a (CF 2 CF 2 ) b (CH 2 CH 2 ) c OCOCR═CH 2   [I]

wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 6, a is an integer of 1 to 4; b is an integer of 0 to 3; and c is an integer of 1 to 3; and a (meth)acrylic acid derivative represented by the general formula:

(CH 2 ═CRCO) m R′  [II]

wherein R is a hydrogen atom or a methyl group, m is 1, 2, or 3; and when m is 1, R′ is OH group, NH 2 group that is unsubstituted or mono- or di-substituted with an alkyl group having 1 to 6 carbon atoms, or a monovalent group derived from an alkylene glycol or polyalkylene glycol group containing an alkylene group having 2 or 3 carbon atoms; when m is 2 or 3, R′ is a divalent or trivalent organic group derived from a diol or triol. The copolymerization reaction is performed using a hydrocarbon-based peroxide or azo compound polymerization initiator. Also disclosed are nano-silica composite particles formed as a condensate of the fluorine-containing oligomer and an alkoxysilane with nano-silica particles.

First claim

The invention claimed is:

1. Nano-silica composite particles formed as a condensate of a fluorine-containing oligomer and an alkoxysilane with nano-silica particles, wherein the fluorine-containing oligomer is a copolymer of a fluoroalkyl alcohol (meth)acrylic acid derivative represented by the general formula:
C n F 2n+1 (CH 2 CF 2 ) a (CF 2 CF 2 ) b (CH 2 CH 2 ) c OCOCR═CH 2   [I]

wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 6, a is 1; b is an integer of 1 to 3; and c is an integer of 1 to 3; and a (meth)acrylic acid derivative represented by the general formula:
(CH 2 ═CRCO) m R′  [II]

wherein R is a hydrogen atom or a methyl group, m is 1, 2, or 3; and when m is 1, R′ is OH group, NH 2 group that is unsubstituted or mono- or di-substituted with an alkyl group having 1 to 6 carbon atoms, or a monovalent group derived from an alkylene glycol or polyalkylene glycol group containing an alkylene group having 2 or 3 carbon atoms; when m is 2 or 3, R′ is a divalent or trivalent organic group derived from a diol or triol.

2. Nano-silica composite particles according to claim 1 , wherein the alkoxysilane is a silane derivative represented by the general formula:
(R 1 O) p Si(OR 2 ) q (R 3 ) r   [III]

wherein R 1 and R 3 are each a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group, R 2 is an alkyl group having 1 to 6 carbon atoms or an aryl group, proviso that not all of R 1 , R 2 , and R 3 are aryl groups; and p+q+r is 4, proviso that q is not 0.

3. Method for producing nano-silica composite particles, comprising reacting the fluorine-containing oligomer and an alkoxysilane according to claim 1 in the presence of nano-silica particles using an alkaline or acidic catalyst.

4. Method for producing nano-silica composite particles according to claim 3 , wherein 10 to 100 parts by weight of fluorine-containing oligomer and 0.1 to 100 parts by weight of alkoxysilane are used based on 100 parts by weight of nano-silica particles.

Assignees

• Unimatec Co Ltd
• Univ Hirosaki

Inventors

• Sato Katsuyuki
• Sawada Hideo

Classifications

• C08F220/22 Primary

  Esters containing halogen · CPC title

• C08F220/68 Primary

  Esters · CPC title

• C08L33/16

  Homopolymers or copolymers of esters containing halogen atoms · CPC title

• C08K3/36

  Silica · CPC title

• C08K5/5419

  containing at least one Si—C bond · CPC title