IP Library Granted Patent US 7,595,353
Granted Patent B2
US 7,595,353 · App. 11/528,691 · Granted Sep 29, 2009

Fluorine-containing photocurable polymer composition

Assignee: Chisso Corporation
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Quick Facts
Patent No.
US 7,595,353
App. No.
11/528,691
Granted
Sep 29, 2009
Kind
B2
Abstract

The invention provides a photocurable polymer composition having a fluorine-containing polymer and a fluorine-free polymer, and preferably further having a polymerizable double bond-containing compound and a photopolymerization initiator. The fluorine-containing polymer preferably includes a fluorosilsesquioxane skeleton.

Claims (37)

1. A photocurable polymer composition comprising:

(i) a fluorine-containing polymer (A); and

(ii) a fluorine-free polymer (B),

wherein the fluorine-containing polymer (A) is a copolymer produced from

(I) at least one radically-polymerizable fluorine-containing monomer (a1) represented by a general formula X—Y, in which X is a radically-polymerizable functional group selected from the group consisting of CH 2 ═C(CH 3 )—COO— and CH 2 ═CH—COO—; and Y is a fluorine-containing functional group; and

(II) another radically-polymerizable monomer (a2) having at least one crosslinkable functional group elected from the group consisting of epoxy and oxetanyl,

wherein the fluorine-containing functional group Y is represented by the following Formula (I):

wherein in the Formula (I):

each of R f 1 to R f 7 are independently are at least one of

(i) a linear or branched fluoroalkyl which has approximately 1 to approximately 20 carbon atoms and in which arbitrary methylene may be replaced by oxygen,

(ii) a fluoroaryl which has approximately 6 to approximately 20 carbon atoms and in which one or more hydrogen is replaced by fluorine or —CF 3 ,

(iii) a fluoroarylalkyl which has approximately 7 to approximately 20 carbon atoms and in which one or more hydrogen in the aryl is replaced by fluorine or —CF 3 ,

(iv) a linear or branched alkyl which has approximately 1 to approximately 20 carbon atoms and does not contain fluorine, and in which arbitrary methylene may be replaced by oxygen,

(v) an aryl which has approximately 6 to approximately 20 carbon atoms and does not contain fluorine, and

(vi) an arylalkyl which has approximately 7 to approximately 20 carbon atoms and does not contain fluorine;

wherein at least one of R f 1 to R f 7 is fluoroalkyl, fluoroaryl, or fluoroarylalkyl; and

wherein R 2 is a single bond or alkylene which has approximately 1 to approximately 20 carbon atoms and in which arbitrary methylene may be replaced by oxygen and wherein the fluorine-free polymer (B) is a copolymer produced from a radically-polymerizable carboxyl-containing monomer (b1) and another radically-polymerizable monomer (b2), and wherein the radically-polymerizable carboxyl-containing monomer (b1) is methacrylic acid; and the radically-polymerizable monomer (b2) contains at least one of benzyl (meth)acrylate, N-phenylmaleimide, 2-hydroxyethyl (meth)acrylate, styrene, glycidyl (meth)acrylate, 3-ethyl-3-oxetanylmethyl (meth)acrylate, cyclohexyl (meth)acrylate, and a radically-polymerizable monomer represented by the following Formula (II):

wherein Formula (II), R 1 is at least one of hydrogen and methyl, R 2 is at least one of hydrogen and alkyl having approximately 1 to approximately 5 carbon atoms, and n is an integer of approximately 1 to approximately 5.

2. The photocurable polymer composition according to claim 1 , further comprising:

(i) a polymerizable double bond-containing compound (C); and

(ii) a photopolymerization initiator (D).

3. The photocurable polymer composition according to claim 1 , wherein each of R f 1 to R f 7 is independently a fluoroalkyl.

4. The photocurable polymer composition according to claim 3 , wherein each of R f 1 to R f 7 are independently at least one of 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 3,3,4,4,4-pentafluorobutyl, and 3,3,4,4,5,5,6,6,6-nonafluorohexyl.

5. The photocurable polymer composition according to claim 4 , wherein each of to R f 1 to R f 7 are independently at least one of 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, and 3,3,4,4,5,5,6,6,6-nonafluorohexyl.

6. The photocurable polymer composition according to claim 1 , wherein R 2 is at least one of ethylene, propylene, and butylene.

7. The photocurable polymer composition according to claim 6 , wherein R 2 is propylene.

8. The photocurable polymer composition according to claim 2 , wherein approximately 50 wt % or more of the polymerizable double bond-containing compound (C) is a compound having two or more polymerizable double bonds.

9. The photocurable polymer composition according to claim 2 , wherein approximately 50 wt % or more of the polymerizable double bond-containing compound (C) is a compound having four or more polymerizable double bonds.

10. The photocurable polymer composition according to claim 2 , wherein the photopolymerization initiator (D) contains at least one of 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholiphenyl)-butanone-1,3,3,4,4-tetra-(t-butylperoxycarbonyl)benzophenone, 3,3′-di(methoxycarbonyl)-4,4′-di(t- butylperoxycarbonyl)benzophenone, 3,4′-di(methoxycarbonyl)-4,3′-di(t-butylperoxycarbonyl) benzophenone, and 4,4′-di(methoxycarbonyl)-3,3′-di(t-butylperoxycarbonyl)benzophenone.

11. The photocurable polymer composition according to claim 2 , wherein the photopolymerization initiator (D) contains at least one of 3,3′-di(methoxycarbonyl)-4,4′-di(t-butylperoxycarbonyl)benzophenone, 3,4′-di(methoxycarbonyl)-4,3′-di(t-butylperoxycarbonyl) benzophenone, and 4,4′-di(methoxycarbonyl)-3,3′-di(t-butylperoxycarbonyl)benzophenone.

12. The photocurable polymer composition according to claim 1 , wherein the fluorine-containing polymer (A) comprises approximately 1 to approximately 200 parts by weight with respect to approximately 100 parts by weight of the fluorine-free polymer (B).

13. The photocurable polymer composition according to claim 1 , wherein the fluorine-containing polymer (A) comprises approximately 5 to approximately 50 parts by weight with respect to 100 parts by weight of the fluorine-free polymer (B).

14. The photocurable polymer composition according to claim 1 , wherein the Fluorine-containing polymer (A) comprises approximately 10 to approximately 30 parts by weight with respect to approximately 100 parts by weight of the fluorine-free polymer (B).

15. A transparent film comprising the photocurable polymer composition according to claim 1 .

16. An insulating film comprising the photocurable polymer composition according to claim 1 .

17. A protective film comprising the photocurable polymer composition according to claim 1 .

18. A display device comprising a photospacer wherein the photospacer comprises the film according to claim 15 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2011
From: CHISSO CORPORATION
To: JNC CORPORATION
Reel/Frame 026187/0940 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2006
From: MINAMISAWA, HISANOBU; YAMAHIRO, MIKIO; MEGURO, AKIRA
To: CHISSO CORPORATION
Reel/Frame 018709/0202 →
Priority Claims (1)
JP 2005-283203 · Sep 29, 2005 · national
Continuity (1)
Related Publication 20070082968A1 · Apr 12, 2007