Surface treatment composition

Patent metadata

Field	Value
Publication number	US-2016237199-A1
Application number	US-201415029867-A
Country	US
Kind code	A1
Filing date	Oct 16, 2014
Priority date	Oct 18, 2013
Publication date	Aug 18, 2016
Grant date	—

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, (B2) a silane compound having an active hydrogen, and (B3) a monomer having an active hydrogen and a carbon-carbon double bond. Further, a molar amount of an isocyanate group in component (A) is equal to a total molar amount of component (B), and a molar amount of component (B1), component (B2) and component (B3) per 9 moles of the isocyanate group in component (A) are component (B1) 0.1-2 moles, component (B2) 0.05-2 moles, and component (B3) 5-8.85 moles, respectively.

First claim

1 . A 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,
wherein
component (B) comprises:
(B1) a perfluoropolyether having an active hydrogen,
(B2) a silane compound having an active hydrogen, and
(B3) a monomer having an active hydrogen and a carbon-carbon double bond
a molar amount of an isocyanate group in component (A) is equal to a total molar amount of component (B), and a molar amount of component (B1), component (B2) and component (B3) per 9 moles of the isocyanate group in component (A) are
component (B1) 0.1-2 moles,
component (B2) 0.05-2 moles, and
component (B3) 5-8.85 moles, respectively.

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

3 . The 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-R 1 —CH 2 OH  (B1-i)

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

wherein
Rf is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
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; and
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.

4 . The composition according to claim 3 wherein component (B1) is at least one compound of the general formula (B1-i).

5 . The composition according to claim 3 wherein
PFPE is a group of any one of the formulae (i)-(iii):
—(OCF 2 CF 2 CF 2 ) b —  (i)

wherein b is an integer of 1-200,
—(OCF(CF 3 )CF 2 ) b —  (ii)

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 —   (iii)

wherein a and b are each independently 0 or an integer of 1-30, 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.

6 . The composition according to claim 1 wherein component (B2) is at least one compound for the general formula:

wherein R 11 , R 12 , R 13 , R 14 and R 15 are each independently an alkyl group or an aryl group;
R 16 is a divalent organic group;
l and n are each independently 0 or 1;
m is an integer of 1-500;
o is an integer of 0-20; and
p is 0 or 1.

7 . The composition according to claim 1 wherein component (B3) is a compound containing a (meth)acrylate group.

8 . The composition according to claim 1 wherein component (B3) is at least one compound selected from the group consisting of
HO(CH 2 CH 2 ) i OCO(R)C═CH 2

wherein 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, and i is 2-10, for example, 2-2-hydroxyethyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate;
CH 3 CH(OH)CH 2 OCO(R)C═CH 2

wherein R is a hydrogen atom, a chlorine atom, a fluorine atom, or n alkyl group having 1-10 carbon atoms which may be substituted by a fluorine atom;
CH 3 CH 2 CH(OH)CH 2 OCO(R)C═CH 2

wherein R 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;
C 6 H 5 OCH 2 CH(OH)CH 2 OCO(R)C═CH 2

wherein R 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;
HOCH 2 C(CH 2 OCO(R)C═CH 2 ) 3

wherein R 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;
C(CH 2 OCO(R)C═CH 2 ) 3 CH 2 OCH 2 C(CH 2 OCO(R)C═CH 2 ) 2 CH 2 OH

wherein R 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;
HOCH 2 CH 2 OCOC 6 H 5 OCOCH 2 CH 2 OCO(R)C═CH 2

wherein R 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;
H(OCH 2 CH 2 ) n OCO(R)C═CH 2

wherein n is 1-30, and R 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;
H(OCH(CH 3 )CH 2 ) n OCO(R)C═CH 2

wherein n is 1-30, and R 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;
an allylalcohol;
HO(CH 2 ) k CH═CH 2

wherein k is 2-20;
(CH 3 ) 3 SiCH(OH)CH═CH 2 ; and

styrylphenol.

9 . The composition according to claim 1 wherein the reaction of component (A) with component (B) is conducted by reacting a portion of the isocyanate group component (A) with component (B1) and component (B2), and then the rest of the isocyanate group with component (B3).

10 . The composition according to claim 1 , obtained by reacting component (A) with component (B1) and (B3) to provide the first composition,
reacting component (A) with component (B2) and (B3) to provide the second composition, and then, mixing the first composition and the second composition.

11 . The composition according to claim 10 , obtained by reacting component (A) with component (B1) followed by component (B3) to provide the first composition,
by reaction component (A) with component (B2) and then component (B3) to provide the second composition.

12 . The 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 (for example, straight or branched) 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.

13 . A surface treatment composition comprising one or more compositions according to claim 1 .

14 . The surface treatment composition according to claim 13 , comprising a solvent of 5-10,000 parts by mass with respect to the total 100 parts by mass of the composition according to claim 1 .

15 . The surface treatment composition according to claim 14 wherein the solvent is a fluorine-free organic solvent.

16 . The surface treatment composition according to claim 14 wherein the solvent is a mixed solvent of

Assignees

• Daikin Ind Ltd

Inventors

• Yoshida Tomohiro
• Yokotani Saya
• Mitsuhashi Hisashi
• Hanabusa Kakeru

Classifications

• C08G18/3893

  containing silicon · CPC title

• C08G18/5015

  having fluorine atoms · CPC title

• C08G18/672 Primary

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• G02B1/18

  Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence) · CPC title

• C09D183/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence) · CPC title