High energy radiation-curable composition and resin molding

Details High energy radiation-curable composition and resin molding High energy radiation-curable composition and resin molding

2001-06-26

2003-02-04

Seidleck, James J. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Compositions to be polymerized by wave energy wherein said...

C522S148000, C522S182000, C528S025000, C528S026000, C528S030000, C528S032000, C428S446000, C428S447000, C525S100000, C525S101000, C264S001320, C264S001360, C106S038200, C106S038270, C106S038280, C523S106000, C523S107000

Reexamination Certificate

active

06515041

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a high energy radiation-curable composition and a resin molding, and more specifically relates to a high energy radiation-curable composition of superior curability, water repellency, water resistance, oil repellency, transparency, flexibility, and scratch resistance, and to a resin molding having a thin film layer of the composition.
BACKGROUND OF THE INVENTION
In the past, hard coat agents curable by high energy radiation such as ionizing radiation and UV rays have been used in various fields. For example, when coated onto polycarbonate resins and acrylic resins, such hard coat agents have been known to improve wear resistance by preventing scratching of the resin surface. For this reason, they are particularly suitable for use as a substitute for transparent glass used for example for of eyeglasses and automobile headlight covers. Well-known examples of this type of high energy radiation-curable hard coat agents include UV curable hard coat compositions comprising colloidal silica, an acryloxy functional silane, a non-silyl acrylate, and a photopolymerization initiator (see PCT (WO) Sho 57(1982)-500984) and radiation-curable compositions obtained by compounding a cohydrolyzate of a tetralkoxysilane and an unsaturated group-containing alkoxysilane with a multifunctional acrylate (see Japanese Kokai (Unexamined) Patent Application Publication No. Hei 08(1996)-253708).
However, the problem with the former UV curable compositions utilizing colloidal silica was that they tended to gel easily and their storage stability was low. On the other hand, the disadvantage of the latter radiation-curable compositions utilizing a cohydrolyzate of alkoxysilanes was their low water resistance.
It is an object of the present invention to provide a high energy radiation-curable composition and a resin molding of superior curability, water repellency, water resistance, oil repellency, transparency, flexibility, and scratch resistance.
SUMMARY OF THE INVENTION
The present invention relates to a high energy radiation-curable composition comprising
(A) 1 to 99 parts by weight of a partial hydrolysis-condensation product of a mixture of
(a) an alkoxy-containing organopolysiloxane described by formula
(SiO
4/2
)
m
(O
1/2
R)
4m−2n
,
 where R is an alkyl group comprising 1 to 10 carbon atoms, m is an integer of 2 or greater, and n is an integer of ≧(m−1) to ≦(m−1)×2;
(b) an alkoxysilane described by formula
R
1
a
Si(OR
2
)
4−a
,
 where R
1
is a substituted or unsubstituted monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not contain aliphatic unsaturated bonds, R
2
is an alkyl group comprising 1 to 10 carbon atoms, and a is 1 or 2;
(c) an alkoxysilane described by formula
R
3
b
YSi(OR
4
)
3−b
,
 where R
3
is a monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not contain aliphatic unsaturated bonds, R
4
is an alkyl group comprising 1 to 10 carbon atoms, Y is a monovalent organic group containing aliphatic unsaturated bonds, and b is 0 or 1; and
(B) 99 to 1 part by weight of a multifunctional acrylate. The present invention further relates to a resin molding having a thin film layer of the high energy radiation-curable composition on at least one side.
DESCRIPTION OF THE INVENTION
The present invention relates to a high energy radiation-curable composition comprising
(A) 1 to 99 parts by weight of a partial hydrolysis-condensation product of a mixture of
(a) an alkoxy-containing organopolysiloxane described by formula
(SiO
4/2
)
m
(O
1/2
R)
4m−2n
,
 where R is an alkyl group comprising 1 to 10 carbon atoms, m is an integer of 2 or greater, and n is an integer of ≧(m−1) to ≦(m−1)×2;
(b) an alkoxysilane described by formula
R
1
a
Si(OR
2
)
4−a
,
 where R
1
is a substituted or unsubstituted monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not contain aliphatic unsaturated bonds, R
2
is an alkyl group comprising 1 to 10 carbon atoms, and a is 1 or 2;
(c) an alkoxysilane described by formula
R
3
b
YSi(OR
4
)
3−b
,
 where R
3
is a monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not contain aliphatic unsaturated bonds, R
4
is an alkyl group comprising 1 to 10 carbon atoms, Y is a monovalent organic group containing aliphatic unsaturated bonds, and b is 0 or 1; and
(B) 99 to 1 part by weight of a multifunctional acrylate. The present invention further relates to a resin molding having a thin film layer of the high energy radiation-curable composition on at least one side.
First of all, explanations are provided regarding the high energy radiation-curable composition of the present invention. Component (A) is obtained by subjecting a mixture of component (a) to component (c) to partial hydrolysis and condensation. Component (A) imparts water repellency, water resistance, oil repellency, adhesive properties, mold release properties, and other superior properties to cured products of the present composition.
The alkoxy-containing organopolysiloxane of component (a) is a component that improves the post-cure hardness by increasing the crosslinking density of the present composition. Component (a) is described by formula (SiO
4/2
)
m
(O
1/2
R)
4m−2n
. In the formula, R is an alkyl group comprising 1 to 10 carbon atoms, exemplified by methyl, ethyl, propyl, butyl, octyl, and decyl, with ethyl being preferable. Subscript m is an integer of not less than 2, preferably in the range of 2 to 20. Subscript n is an integer of not less than (m−1) and not more than (m−1)×2. Specific examples of such alkoxy-containing organopolysiloxanes include hexamethoxydisiloxane, hexaethoxydisiloxane, hexaisopropoxydisiloxane, and other hexalkoxydisiloxanes when subscript m is 2 and subscript n is 1; and polymethoxysiloxane, polyethoxysiloxane, polyisopropoxysiloxane, and other polyalkoxysiloxanes when subscript m is equal to or greater than 3.
The alkoxysilane of component (b) imparts water repellency to the present composition and is described by formula R
1
a
Si(OR
2
)
4−a
. In the formula, R
1
is a substituted or unsubstituted monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not have aliphatic unsaturated bonds, and is exemplified by methyl, ethyl, propyl, butyl, isobutyl, octyl, decyl, and other alkyl groups; phenyl and other aryl groups; and 3,3,3-trifluoromethyl, perfluorobutylethyl, perfluorooctylethyl, and other fluoroalkyl groups. Among these, methyl, ethyl, propyl, butyl, and isobutyl are preferable, and methyl is especially preferable. R
2
is an alkyl group comprising 1 to 10 carbon atoms exemplified by the same groups as the above-described R. Subscript a is 1 or 2, preferably 1. Examples of component (b) include methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, and ethyltriisopropoxysilane.
The alkoxysilane of component (c) imparts high energy radiation curability to the present composition and is described by formula R
3
b
Ysi(OR
4
)
3−b
. In the formula, R
3
is a monovalent hydrocarbon group comprising 1 to 10 carbon atoms that does not contain aliphatic unsaturated bonds, exemplified by the same groups as the above-described R
1
. R
4
is an alkyl comprising 1 to 10 carbon atoms exemplified by the same groups as the above-described R. Y is a monovalent organic group containing aliphatic unsaturated bonds, specifically exemplified by vinyl, hexenyl, methacryloxy, acryloxy, styryl, vinylether, 3-(methacryloxy)propyl, and 3-(acryloxy)propyl. Subscript b is 0 or 1. Examples of component (c) include vinyltrimethoxysilane, vinyltriethoxysilane, methylvinyldimethoxysilane, 3-(methacryloxy)propyltrimethoxysilane, 3-(methacryloxy)propyltriethoxysilane, 3-(methacryloxy)propylmethyldimethoxysilane, and 3-(acryloxy)propyltrimethoxysilane.
There are no particular limitations concerning the methods used for blending component (a) to component (c

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