Coating compositions, process for producing a cross-linked coating film with such compositions and thus produced articles

Claim 2

1, A coating composition comprising A. from about 5 to about 90 parts by weight of a monomer mixture which consists essentially of (1) from about 20 to about 95% by weight of a polyfunctional monomer having at least three (meth)acryloyloxy groups in one molecule; (2) from about 1 to about 25% by weight of a monomer represented by the formula: wherein R 1 is hydrogen or a methyl group,' R 2 is an alkoxy or (meth)acrylcyloxy group of 1 to 5 carbon atoms and n is an integer of 5 to 30; (3) from about 1 to about 15%.by weight of a sulfonic acid type monomer represented by the formula: wherein R 3 is hydrogen or a methyl group, Y is a -CONH or -COO group and 1, m, n' and r are integers of 0 to 5); (4) from about 1 to about 20% by weight of a phosphoric acid ester-type monomer represented by the formula: wherein R 4 is hydrogen or a methyl group, R5 is hydrogen or a • group, R 6 is hydrogen or a methyl group and m' and n" are integers of 1 to 15; and (5) from about 2 to about 20% by weight of an ethanolamine-type compound represented by the formula: wherein each of R 7 and R 8 is independently hydrogen or an alkyl group of 1 to 15 carbon atoms or a CH 2 CH 2 0H group; together with B. from about 95 to about 10 parts by weight of at lest one organic solvent that forms a uniform solution when mixed with said monomer mixture A; and C. up to 10 parts by weight of a photosensitizing agent per 100 parts by weight of the total of the monomer mixture A and organic solvent B; said coating composition capable of forming a dyeable, cross-linked hardened film high in abrasion resistance, surface smoothness and cloud prevention, said film having a permanent antistaticity when irradiated with active energy rays.

Claim 3

The coating composition according to claim 1 wherein said polyfunctional monomer (1) is a polypentaerythritol poly(meth)acrylate having at least three (meth)acryloyloxy groups per molecule and represented by the formula: wherein at least 3 of X 11 , X 12 , X 13 , X 22' X 23' ― X z2 , X z3 and X 14 are (meth)acryloyloxy gruops and the rest are OH groups and z is an integer of 1 to 5.

Claim 4

The coating composition according to claims 1 or 3 wherein polyfunctional monomer (1) is present in an amount of from about 40 to about 90% by weight of monomer mixture A.

Claim 5

The coatinq composition according to claim 1 wherein low viscosity monomers having- a boiling point of not less than about 150°C. under atmospheric pressure and a viscosity not greater than 20 centipoises is used together with the polyfunctional monomer (1).

Claim 6

The coating composition according to claims 1 or 2 wherein said sulfonic acid-type monomer (3) is present in an amount of from about 5 to about 10% by weight of monomer mixture A.

Claim 7

The coating composition according to claims 1 or 2 wherein said phosphoric acid ester-type monomer is selected from the group consisting of (meth)acryloxyethyl phosphate, di(meth)acryloxyethyl phosphate, (meth)acryloxypropyl phosphate, (meth)-acryloxybutyl phosphate and mixtures thereof.

Claim 8

The coating composition according to claims 1 or 2 wherein said ethanolamine-type compound (5) is present in an amount of from about 5 to about 15% of monomer mixture A.

Claim 9

The coating composition according to claims 1, 2 or 7 wherein said ethanolamine-type compound (5) is selected from the group consisting of ethanolamine, beta-ethylhexylethanolamine, diethanolamine, N-b.utyldiethanolamine, N-hexyldiethanolamine, N-lauryldiethanolamine, N-cetyldiethanolamine, triethanolamine and mixtures thereof.

Claim 10

The coating composition according to claim 1 wherein the weight ratio of component (3) to component (5) is within the range of 0.3:1 to 3:1.

Claim 11

The coating composition according to claims 1 or 2 wherein said organic solvent has a soiling point in the range of about 50 to about 200°C. at atmospheric pressure and a viscosity at room temperature not greater than 10 centipoises.

Claim 12

The coating composition according to claim 1 wherein the amount of said photosensitizing agent C is about 0.01 to about 10 parts by weight of the total of components A and B.

Claim 13

A coating composition comprising A. from about 5 to about 90 parts by weight of a monomer mixture which consists essentially of (1) from about 20 to about 95% by weight of a polypentaerythritol poly(meth)acrylate having at least three (meth)acryloyloxy groups per molecule and represented by the formula: wherein at least 3 of X 11 , X 12 , X 13 , X 22 , X 23 ― X z2 , X z3 and X 14 are (meth)acryloyloxy groups, and the rest are OH groups and z is an integer of 1 to 5; (2) from about 1 to about 25% by weight of a monomer represented by the formula: wherein R 1 is hydrogen or a methyl group, R 2 is an alkoxy or (meth)acryloyloxy group of 1 to 5 carbon atoms and n is an integer of 5 to 30; (3) from about 1 to about 15% by weight of a sulfonic acid-type monomer represented by the formula: wherein R 3 is hydrogen or a methyl group, Y is a -CONH or -COO group and 1, m, n' and r are integers of 0 to 5; (4) from about 1 to about 20% by weight of a phosphoric acid ester-type monomer represented by the formula: wherein R 4 is hydrogen or a methyl group, R 5 is hydrogen or a group, R 6 is hydrogen or a methyl group and m' and n" are integers of 1 to 15; and (5) from about 2 to about 20% by weight of an ethanolamine-type compound represented by the formula: wherein each of R 7 and R 8 is independently hydrogen or an alkyl group of 1 to 15 carbon atoms or a CH 2 CH 2 0H group; together with R. from about 95 to about 10 parts by weight of at least one organic solvent that forms a uniform solution when mixed with said monomer mixture A; and C. 0.01 to 10 parts by weight of a photosensitizing agent per 100 parts by weight of the total of the monomer mixture A and organic solvent B; said coating composition capable of forming a dyeable, cross-linked hardened film high in abrasion resistance, surface smoothness and cloud prevention, said film having a permanent antistaticity when irradiated with active energy rays.

Claim 14

A coating composition comprising A. from about 5 to about 90 parts by weight of a monomer mixture which consists essentially of (1) from about 20 to about 95% by weight of a polypentaerythritol poly(meth)acrylate having at least three (meth)acryloyloxy groups per molecule and represented by the formula: wherein at least 3 of X 11 , X 12 , X 13 , X 22 , X 23 ― X z2 , X z3 and X 14 are (meth)acryloyloxy groups, and the rest are OH groups and z is an integer of 1 to 5; (2) from about 1 to about 25% by weight of a monomer represented by the formula: wherein R 1 is hydrogen or a methyl group, R 2 is an alkoxy or (meth)acryloyloxy group of 1 to 5 carbon atoms and n is an integer of 5 to 30; (3) from about 1 to about 15% by weight of a sulfonic acid-type monomer represented by the formula: wherein R 3 is hydrogen or a methyl group, Y is a -CONH or -COO group and 1, m, n' and r are integers of 0 to 5; (4) from about 1 to about 20% by weight of a phosphoric acid ester-type monomer represented by the formula: wherein R 4 is hydrogen or a methyl group, R 5 is hydrogen or a group, R 6 is hydrogen or a methyl group and m' and n" are integers of 1 to 15; and (5) from about 2 to about 20% by weight of an ethanolamine-type compound represented by the formula: wherein each of R 7 and R 8 is independently hydrogen or an alkyl group of 1 to 15 carbon atoms or a CH 2 CH 2 0H group; together with R. from about 95 to about 10 parts by weight of at least one organic solvent that forms a uniform solution when mixed with said monomer mixture A; and C. 0.01 to 10 parts by weight of a photosensitizing agent per 100 parts by weight of the total of the monomer mixture A and organic solvent B; said coating composition capable of forming a dyeable, cross-linked hardened film high in abrasion resistance, surface smoothness and cloud prevention, said film having a permanent antistaticity when irradiated with active energy rays.

Claim 15

A process for providing a dyeable, cross-linked hardened film exhibiting substantial abrasion resistance, permanent antistaticity and a smooth surface, said process comprising: (i) applying the coating composition of claim 12 to the surface of a synthetic resin article, and (ii) exposing and irradiating the thus- applied coating to cross-linking energy rays thereby corss-linking and curing the coating and forming a hardened film on said article.

Claim 16

The process according to claim 13 wherein said synthetic resin article is selected from the group consisting of polymethyl methacrylate, polycrabonate, polyallyldiglycol carbonate and mixtures thereof.

Claim 17

A coated, abrasion resistant optical lens produced according to the process of claim 13.

Claim 18

A coated, abrasion resistant lighting fixture cover produced according to the process of claim 13.

Claim 19

A coated, abrasion resistant eyeglass lens produced according to the process of claim 13.