Surface treatment composition

Patent metadata

Field	Value
Publication number	US-9909027-B2
Application number	US-201314442132-A
Country	US
Kind code	B2
Filing date	Nov 5, 2013
Priority date	Nov 13, 2012
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

The present invention provides a composition which is able to form a layer having excellent surface slip property and friction durability in addition to water-repellency, oil-repellency and antifouling property. The present invention provides a surface-treatment composition comprising (A) at least one fluorine-containing polymer having a curable moiety, and (B) at least one silicon-containing polymer having a curable moiety.

First claim

The invention claimed is:

1. A composition comprising:
(A) at least one fluorine-containing polymer having a curable moiety, and
(B) at least one silicon-containing polymer having a curable moiety,
wherein the fluorine-containing polymer (A) is at least one fluorine-containing polymer of any one of the following general formulae (A1) and (A2):
Rf—R 1 —R 2 —R 3 —(R 4 ) n1 —R 5 —R 6   (A1)

R 6 —R 5 —(R 4 ) n1 —R 3 —R 2 —R 1 —R 2 —R 3 —(R 4 ) n1 —R 5 —R 6   (A2)

wherein:
Rf represents an alkyl having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
R 1 is a group of the following formula:
—(OC 4 F 8 ) w —(OC 3 F 6 ) a —(OC 2 F 4 ) b —(OCF 2 ) c —

wherein a, b, c and w are each independently an integer of 0 or more and 200 or less, the sum of a, b, c and w is 1 or more and the occurrence order of the respective repeating units in parentheses is not limited in the formula;
R 2 is a group of the following formula:
-(Q) d -(CFZ) e —(CH 2 ) f —

wherein Q represents an oxygen atom, phenylene, carbazolylene, —NR a — wherein R a represents a hydrogen atom or an organic group, or a divalent polar group,
Z represents a hydrogen atom, a fluorine atom or a lower fluoroalkyl group, and
d, e and f are each independently an integer of 0 or more and 50 or less, the sum of d, e and f is 1 or more, the occurrence order of the respective repeating units in parentheses is not limited in the formula;
R 3 represents a divalent organic group;
R 4 represents, each independently at each occurrence, R 4a or R 4b : provided that at least one of R 4 is R 4a ,
R 4a is a group of the following formula:

wherein R 31 represents, each independently at each occurrence, a hydrogen atom or an alkyl group,
R 32 represents, each independently at each occurrence, a hydrogen atom or an alkyl group,
R 33 represents, each independently at each occurrence, an organic group having a curable moiety,
Y 1 represents —O—, —N(R c )—, phenylene or carbazolylene,
R c represents an organic group, and
Y 2 represents a linker wherein the number of atoms of the main backbone is 1-16;
R 4b represents, each independently at each occurrence, a divalent organic group having no curable moiety;
n1 is an integer of 1 or more and 50 or less;
R 5 represents —O—, —S—, —NH— or a bond;
R 6 represents Rf—R′—R 2 — wherein Rf, R 1 and R 2 are as defined above, a monovalent organic group or a hydrogen atom, and
the silicon-containing polymer (B) is at least one silicon-containing polymer of any one of the following general formulae (B1) and (B2):

wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 22 , R 23 , R 24 and R 25 represent each independently an alkyl group or an aryl group;
R 18 represents a divalent organic group;
X 1 represents a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl having 1-10 carbon atoms which may be substituted by a fluorine atom, and
n4 and n5 are each independently an integer of 1 or more and 500 or less.

2. The composition according to claim 1 wherein the fluorine-containing polymer (A1) and (A2) are at least one fluorine-containing polymer of any one of the following general formulae (A1a) and (A2a), respectively:

wherein Rf, R 1 , R 3 , R 6 , X 1 , Z and n1 are as defined in claim 1 ,
g is 0 or 1,
h is 1 or 2, and
q1 is one or more and 5 or less.

3. The composition according to claim 1 wherein Rf is a perfluoroalkyl group having 1-16 carbon atoms.

4. The composition according to claim 1 wherein the silicon-containing polymer (B) has a number average molecular weight of 500 or more and 20,000 or less.

5. The surface treatment composition according to claim 1 comprising the fluorine-containing polymer (A) at 60% by mass or more with respect to the total mass of the fluorine-containing polymer (A) and the silicon-containing polymer (B).

6. The composition according to claim 1 further comprising at least one fluorine-containing oil of the following general formula (C):
Rf—(OC 4 F 8 ) w′ —(OC 3 F 6 ) a′ —(OC 2 F 4 ) b′ —(OCF 2 ) c′ —Rf′  (C)

wherein Rf an alkyl having 1-16 carbon atoms which may be substituted by one or more fluorine atoms,
Rf′ represents a hydrogen atom, a fluorine atom, or an alkyl having 1-16 carbon atoms which may be substituted by one or more fluorine atoms,
a′, b′, c′ and w′ are each independently an integer of 0 or more and 300 or less, the sum of a′, b′, c′ and w′ is 1 or more and the occurrence order of the respective repeating units in parentheses is not limited in the formula,
at 40% by mass or less with respect to the total mass of the fluorine-containing polymer (A) and the fluorine-containing oil (C).

7. The composition according to claim 1 further comprising a solvent of 5-10,000 parts by mass with respect to the total 100 parts by mass of the fluorine-containing polymer (A) and the silicon-containing polymer (B), and if present the fluorine-containing oil (C).

8. The composition according to claim 1 further comprising an active energy curing initiator.

9. An article comprising a base material and a layer which is formed on a surface of the base material from the composition according to claim 1 .

10. The article according to claim 9 which is an optical member.

11. A curable composition comprising the composition according to claim 1 in a matrix forming composition at 0.01-10% by mass with respect to the total mass of the matrix forming composition and the composition according to claim 1 .

12. An article comprising a base material and a layer which is formed on a surface of the base material from the curable composition according to claim 11 .

13. The article according to claim 12 which is an optical member.

Assignees

• Daikin Ind Ltd

Inventors

• Yoshida Tomohiro
• Fukami Dai

Classifications

• C09D201/04

  containing halogen atoms · CPC title

• C08F299/08

  from polysiloxanes · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C09D133/16 Primary

  Homopolymers or copolymers of esters containing halogen atoms · CPC title

• C09D201/02

  characterised by the presence of specified groups {, e.g. terminal or pendant functional groups} · CPC title