Modified acrylic resin cured product, and laminate thereof, and production methods therefor

Patent metadata

Field	Value
Publication number	US-10428194-B2
Application number	US-201615553208-A
Country	US
Kind code	B2
Filing date	Feb 24, 2016
Priority date	Feb 25, 2015
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

The purpose of the present invention is to provide a modified acrylic resin cured product, particularly, a modified acrylic resin film, having excellent lubricity and excellent transparency, and a laminate including the modified acrylic resin film. The modified acrylic resin cured product (C) according to the present invention is obtained by treating the surface of a cured product (X) including an acrylic resin by using a compound (A) containing, in each molecule, one or more anionic hydrophilic groups forming an ion pair with an onium ion of an amino silicone, and one or more groups selected from the group consisting of a group containing a polymerizable carbon-carbon double bond, an amino group, a mercapto group and a hydroxy group.

First claim

The invention claimed is:

1. A modified acrylic resin cured product (C) obtained by treating the surface of a cured product (X) composed of an acrylic resin
with a compound (A) comprising, in the molecule,
one or more of anionic hydrophilic groups forming an ion pair with an onium ion of an amino silicone, and
one or more of groups selected from the group consisting of groups containing a polymerizable carbon-carbon double bond, amino groups, mercapto groups, and hydroxyl groups,
wherein the amino silicone has a molecular weight of 100 to 1,000,000 and is one or more selected from compounds represented by the following general formulae (a1) to (a3):
General Formula (a1):

wherein in the formula (a1), R 1 to R 8 are independently a hydrogen atom, a C 1-6 alkyl group, or a C 1-6 alkoxy group; n 010 is an integer of 0 to 10; n 0100 is an integer of 0 to 100; n 02 is an integer of 0 to 2; n 13 is an integer of 1 to 3; n 02 +n 13 =3; # 1 and # 2 represent bonding hands; and # 1 and # 2 are bonded together;
General Formula (a2):

wherein in the formula (a2), R 1 to R 11 are independently a hydrogen atom, a C 1-6 alkyl group, or a C 1-6 alkoxy group; n 01000 is an integer of 0 to 1000; n 110 is an integer of 1 to 10; n 010 is an integer of 0 to 10; n 12 is an integer of 1 to 2; n 01 is an integer of 0 to 1; n 01 +n 12 =2; # 1 and # 2 represent bonding hands; # 1 and # 2 are bonded together; and the compounds represented by the formula (a2) do not include the compounds represented by the formula (a1);
General Formula (a3):

wherein in the formula (a3), R 1 to R 5 are independently a hydrogen atom, a C 1-6 alkyl group, or a C 1-6 alkoxy group); n 01000 is an integer of 0 to 1000; n 010 is an integer of 0 to 10; n 01 is an integer of 0 to 2; n 12 is an integer of 1 to 3; n 01 +n 12 =3; n 01 s and n 12 s each may be the same as or different from one another; # 1 and # 2 represent bonding hands; and # 1 and # 2 are bonded together.

2. The modified acrylic resin cured product (C) according to claim 1 , wherein the surface treatment is carried out in the copresence of
a compound (A′) comprising, in the molecule,
one or more of anionic hydrophilic groups forming an ion pair with one or more selected from the group consisting of hydrogen ions, alkali metal ions, alkaline earth metal ions, ammonium ions, and amine ions other than an onium ion of the amino silicone, and
one or more of groups selected from the group consisting of groups containing a polymerizable carbon-carbon double bond, amino groups, mercapto groups, and hydroxyl groups.

3. The modified acrylic resin cured product (C) according to claim 1 , wherein the compound (A) is one or more selected from compounds represented by the general formulae (A1) to (A6):
General Formula (A1):

wherein in the formula (A1), D 1 is a (meth)acryloyloxy group (only when q is 1), a (meth)acryloylthio group (only when q is 1), a (meth)acrylamido group (only when q is 1), a vinyl group, an isopropenyl group, a (meth)allyl group, a styryl group, a mercapto group, an amino group, a methylamino group, or an ethylamino group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; R is a main chain having 1 to 100 carbon atoms and may include, therein, one or more groups selected from aromatic rings, alicyclic groups, ether groups, and ester groups; and q is 0 or 1;
General Formula (A2):

wherein in the formula (A2), R represents a hydrogen atom or a methyl group; Rs may be the same as or different from one another; R 16 is a hydrogen atom or a C 1-6 alkyl group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; and n 110 is an integer of 1 to 10;
General Formula (A3):

wherein in the formula (A3), D 1 is a (meth)acryloyloxy group (only when q is 1), a (meth)acryloylthio group (only when q is 1), a (meth)acrylamido group (only when q is 1), a vinyl group, an isopropenyl group, a (meth)allyl group, a styryl group, a mercapto group, an amino group, a methylamino group or an ethylamino group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; R is a main chain having 1 to 100 carbon atoms and may include, therein, one or more groups selected from aromatic rings, alicyclic groups, ether groups, and ester groups; and q is 0 or 1;
General Formula (A4):

wherein in the formula (A4), D 2 is a (meth)acryloyloxy group, a (meth)acryloylthio group, a (meth)acrylamido group, a vinyl group, an isopropenyl group, a (meth)allyl group, a styryl group, a mercapto group, an amino group, a methylamino group or an ethylamino group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; R is a main chain having 1 to 100 carbon atoms and may include, therein, one or more groups selected from aromatic rings, alicyclic groups, ether groups, and ester groups; a and b are independently an integer of 1 or 2; a+b=3; when a is 2, D 2 s and Rs each may be the same as or different from one another; when b is 2, SiAs may be the same as or different from one another; and q is 0 or 1;
General Formula (A5):

wherein in the formula (A5), D 3 , R 3 , and SO 3 SiA are groups bonded to carbons on rings included in the formula; D 3 is independently a vinyl group, an isopropenyl group, a (meth)allyl group, a styryl group, a mercapto group, an amino group, a methylamino group, an ethylamino group, or a hydroxyl group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; R 3 is independently a hydrogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; k is an integer of 0 to 10; l and m are independently an integer of 1 to 11; k+l+m=6+2n; n is an integer of 0 to 3; when l is 2 or greater, D 3 s may be the same as or different from one another; when k is 2 or greater, R 3 s may be the same as or different from one another; and when m is 2 or greater, SiAs may be the same as or different from one another;
General Formula (A6):

wherein in the formula (A6), D 3 , R 3 , and SO 3 SiA are groups bonded to carbons on rings included in the formula; D 3 is independently a vinyl group, an allyl group, an isopropenyl group, a styryl group, a mercapto group, an amino group, a methylamino group, an ethylamino group, or a hydroxyl group; SiA is an onium ion of an amino silicone having a molecular weight of 100 to 1,000,000; R 3 is independently a hydrogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; r is an integer of 0 to 6; q and p are independently an integer of 1 to 7; p+q+r=8; when p is 2 or greater, D 3 s may be the same as or different from one another; when r is 2 or grea

Assignees

• Mitsui Chemicals Inc

Inventors

• Okazaki Koju

Classifications

• C08J2351/00

  Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• B32B2307/728

  Hydrophilic · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• B32B27/30

  comprising vinyl {(co)polymers; comprising acrylic (co)polymers} · CPC title