Surface treatment composition

Patent metadata

Field	Value
Publication number	US-9822259-B2
Application number	US-201615098372-A
Country	US
Kind code	B2
Filing date	Apr 14, 2016
Priority date	Apr 17, 2015
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

A composition including a compound containing a carbon-carbon double bond obtained by reacting (A) a polyisocyanate which is a trimer of diisocyanate, with (B) a compound having an active hydrogen, wherein component (B) includes (B1) a perfluoropolyether having an active hydrogen, and (B2) a monomer having an active hydrogen and at least two groups having a carbon-carbon double bond.

First claim

The invention claimed is:

1. A surface treatment composition comprising a compound containing a carbon-carbon double bond obtained by reacting
(A) a polyisocyanate which is a trimer of diisocyanate, with
(B) a compound having an active hydrogen, and a solvent

wherein
component (B) comprises:
(B1) a perfluoropolyether having an active hydrogen, and
(B2) a monomer having an active hydrogen and at least two groups having a carbon-carbon double bond,
the perfluoropolyether having an active hydrogen is at least one compound of any one of the following general formulae (B1-i) and (B1-ii):
Rf—PFPE 1 -Z—X  (B1-i)

X—Z—PFPE 2 -Z—X  (B1-ii)

wherein:
Rf is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
PFPE 1 is a group of the formula:
—(OCF 2 CF 2 CF 2 ) b —

wherein b is an integer of 1-200;
—(OCF 2 CF 2 CF 2 CF 2 ) a —(OCF 2 CF 2 CF 2 ) b —(OCF 2 CF 2 ) c —(OCF 2 ) d —

wherein a and b are each independently 0 or an integer of 1-30, and c and d are each independently an integer of 1-200, and the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula;

or
—(OC 2 F 4 —R 5 ) i —

wherein R 5 is a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 ; and
i is an integer of 2-100;

PFPE 2 is a group of the formula:
—(OCF 2 CF 2 CF 2 ) b —

wherein b is an integer of 1-200,

or
—(OC 2 F 4 —R 5 ) i —

wherein R 5 is a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 ; and
i is an integer of 2-100;

Z is each independently a divalent organic group; and
X is an active hydrogen containing group,
the solvent is 5-10,000 parts by mass with respect to the total 100 parts by mass of the composition, and
the solvent is a fluorine-containing organic solvent, or a mixed solvent of a fluorine-free organic solvent and a fluorine-containing organic solvent.

2. The surface treatment composition according to claim 1 wherein component (A) is an isocyanurate type polyisocyanate.

3. The surface treatment composition according to claim 1 wherein component (B1) is at least one compound of any one of the following general formulae (B1-i′) and (B1-ii′):
Rf—PFPE 1 -R 1 —CH 2 OH  (B1-i′)

HOCH 2 —R 1 —PFPE 2 -R 1 —CH 2 OH  (B1-ii′)

wherein:
Rf, PFPE 1 and PFPE 2 are as defined in claim 1 ; and
R 1 is each independently a group of the following formula:
—(Y) f —(CR 3 2 ) j —

wherein
Y is an oxygen atom or a divalent polar group,
R 3 is, each independently at each occurrence, a hydrogen atom or a fluorine atom,
f is an integer of 0-50,
j is an integer of 0-100,
the sum of f and j is at least one, and
the occurrence order of the respective repeating units in parentheses is not limited in the formula.

4. The surface treatment composition according to claim 3 wherein R 1 is each independently a group of the following formula:
—(Y) f —(CF 2 ) g —(CH 2 ) h —

wherein
Y is an oxygen atom or a divalent polar group,
f, g and h are each independently an integer of 0-50,
the sum of f, g and h is at least one, and
the occurrence order of the respective repeating units in parentheses is not limited in the formula.

5. The surface treatment composition according to claim 1 wherein component (B1) is at least one compound of the general formula (B1-i).

6. The surface treatment composition according to claim 1 wherein a number average molecular weight of the perfluoropolyether having an active hydrogen in component (B1) is 500-12,000.

7. The surface treatment composition according to claim 1 wherein the group having the carbon-carbon double bond in component (B2) is a group of the formula:
—OC(O)—CR 2 ═CH 2

wherein
R 2 is a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having 1-10 carbon atoms which may be substituted by a fluorine atom.

8. The surface treatment composition according to claim 1 wherein the group having a carbon-carbon double bond in component (B2) is a (meth)acrylate group.

9. The surface treatment composition according to claim 1 wherein component (B2) has at least 3 carbon-carbon double bonds.

10. The surface treatment composition according to claim 1 wherein component (B2) is at least one compound selected from the group consisting of
HO—CH 2 —C(CH 2 —OC(O)—CR 2 ═CH 2 ) 3 ;

HO—CH 2 —C(CH 2 —OC(O)—CR 2 ═CH 2 ) 2 —CH 2 OCH 2 —C(CH 2 —OC(O)—CR 2 ═CH 2 ) 3 ;

HO—CH(CH 2 —OC(O)—CR 2 ═CH 2 ) 2 ;

HO—Y 1 p —CH 2 CH 2 -Q(CH 2 CH 2 O—X p —CO—CR 2 ═CH 2 ) 2 ;

HO—Y 2 p —CH 2 —C(CH 2 O—Y 2 p —CO—CR 2 ═CH 2 ) 3 ; or

HO—Y 2 p —CH 2 —C(CH 2 —O—Y 2 p —C(O)—CR 2 ═CH 2 ) 2 —CH 2 OCH 2 —C(CH 2 —O—Y 2 p —C(O)—CR 2 ═CH 2 ) 3

wherein R 2 is a hydrogen atom, a chlorine atom, a fluorine atom or an alkyl group having 1-10 carbon atoms which may be substituted by a fluorine atom,
Q is a group of the formula:

Y 1 is —CO—(CH 2 ) 5 —O—;
Y 2 is each independently —CH 2 CH 2 O— or —CH 2 CH(CH 3 )O—;
p is each independently an integer of 0-2.

11. The surface treatment composition according to claim 10 wherein component (B2) is at least one compound selected from the group consisting of pentaerythritol triacrylate, dipentaerythritol pentaacrylate, 2-hydroxy-3-methacrylpropylacrylate, 2-hydroxyethyl bis(2-acryloxyethyl)isocyanurate, caprolatone modified 2-hydroxyethyl bis(2-acryloxyethyl)isocyanurate, ethoxylated pentaerythritol triacrylate, propoxylated pentaerythritol triacrylate, ethoxylated dipentaerythritol pentaacrylate, propoxylated dipentaerythritol pentaacrylate, ethoxylated pentaerythritol trimethacrylate, propoxylated pentaerythritol trimethacrylate, ethoxylated dipentaerythritol pentaacrylate, and propoxylated dipentaerythritol pentaacrylate.

12. The surface treatment composition according to claim 1 wherein component (B1) is
Rf—(OCF 2 CF 2 CF 2 ) b —Z—X

wherein Rf, Z, X and b are as defined in claim 1 , and
component (B2) is pentaerythritol triacrylate.

13. The surface treatment composition according to claim 1 comprising at least one fluorine-containing oil of the following general formula (C):
Rf 1 —PFPE-Rf 2   (C)

wherein:
Rf 1 is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
Rf 2 is a hydrogen atom, a fluorine atom, or an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms; and
PFPE is a group of the general formula:
—(OC 4 F 8 ) a′ —(OC 3 F 6 ) b′ —(OC 2 F 4 ) c′ —(OCF 2 ) d′ —

wherein a′, b′, c′ and d′ are each independently an integer of 0-200, the sum of a′, b′, c′ and d′ is at least one, and the occurrence order of the respective repeating units in parentheses with the subscript a′, b′, c′ or d′ is not limited in the formula.

14. The surface treatment composition according to claim 1 comprising an active energy curing initiator.

15. A curable composition comprising
the surface treatment composition according to claim 1 ; and
a matrix forming composition.

16. The curable composition according to claim 15 comprising a solvent of 0-19,900 parts by mass with respect to the total 100 parts by mass of the surface treatment composition according to claim 1 and the matrix forming composition.

17. The curable composition according to claim 16 wherein the solvent is a fluorine-free organic s

Assignees

• Daikin Ind Ltd

Inventors

• Nii Saya
• Hanabusa Kakeru
• Mohara Kensuke

Classifications

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/673

  containing two or more acrylate or alkylacrylate ester groups · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• C08G18/2885

  containing halogen atoms · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title