EP0331087A2 — Ultraviolet-curing coating composition and produc…

Claim 1

Independent Claim 86 words

An ultraviolet-curing coating composition comprising as principal components: (A) 100 parts by weight of a photopolymerizable composition composed of (a-1) 50-100 wt.% of a crosslinking-polymerizable compound containing at least two acryloyloxy or methacryloyloxy groups per molecule and (a-2) 0-50 wt.% of another compound copolymerizable with the crosslinking-polymerizable compound (a-1); (B) 0.02-10 parts by weight of a photoinitiator comprising a photoinitiator compound (b-1), the peak of sensitive wavelengths of said photoinitiator compound (b-1) being between 365-400 nm; and (C) 0.1-15 parts by weight of an ultraviolet absorber.

Claim 2

Dependent Claim 86 words

An ultraviolet-curing coating composition comprising as principal components: (A) 100 parts by weight of a photopolymerizable composition composed of (a-1) 50-100 wt.% of a crosslinking-polymerizable compound containing at least two acryloyloxy or methacryloyloxy groups per molecule and (a-2) 0-50 wt.% of another compound copolymerizable with the crosslinking-polymerizable compound (a-1); (B) 0.02-10 parts by weight of a photoinitiator comprising a photoinitiator compound (b-1), the peak of sensitive wavelengths of said photoinitiator compound (b-1) being between 365-400 nm; and (C) 0.1-15 parts by weight of an ultraviolet absorber.

Claim 3

Dependent Claim 74 words

The coating composition as claimed in Claim 1, wherein the crosslinking-polymerizable compound (a-1) comprises a compound represented by the following formula (I): wherein n is an integer of 1-4, at least three of Xs are independently a O- group, m stands for an integer of 0-2, R 1 means a hydrogen atom or methyl group and R 2 denotes an alkylene group having 1-6 carbon atoms, and any remaining X is an OH group.

Claim 4

Dependent Claim 37 words

The coating composition as claimed in Claim 1, wherein the crosslinking-polymerizable comprises a polyacrylate and/or polymethacrylate of a saturated or unsaturated polyester obtained by reacting a polyhydric alcohol, a polycarboxylic acid, and acrylic acid and/or methacrylic acid.

Claim 5

Dependent Claim 66 words

The coating composition as claimed in Claim 1, wherein the crosslinking-polymerizable compound comprises a urethane polyacrylate or urethane polymethacrylate obtained by reacting a polyisocyanate represented by the following formula (II): wherein R is an alkylene group having 1-10 carbon atoms or a phenylene, substituted phenylene or diphenylene group, with a compound containing at least one acryloyloxy or methacryloyloxy group and at least one active hydrogen atom.

Claim 6

Dependent Claim 79 words

The coating composition as claimed in claim 1, wherein the crosslinking-polymerizable compound comprises a urethane polyacrylate or polymethacrylate represented by the following formula (IV): wherein R 6 means a (meth)acryloyloxy group, R 7 denotes a hydrogen atom or methyl group, R 8 is a phenylene group, a substituted phenylene group or an alkylene group having 2-6 carbon atoms, and Q is in which p and q are individually an integer of 1-8 and y is an integer of 0-10.

Claim 7

Dependent Claim 67 words

The coating composition as claimed in Claim 1, wherein the crossfinking-polymerizable compound (a-1) is a mixture of 0-75 wt.% of a compound containing at least two acryloyloxy or methacryloyloxy groups and having a viscosity higher than 150 cps at 20° C and 25-100 wt.% of another compound containing two or three acryloyloxy or methacryloyloxy groups and having a viscosity not higher than 150 cps at 20 C.

Claim 8

Dependent Claim 50 words

The coating composition as claimed in Claim 1, wherein the photoinitiator compound (b-1) is represented by the following formula (III): wherein R 3 , R 4- and R 5 mean independently an alkyl or oxyalkyl group having 1-8 carbon atoms or a phenyl, substituted phenyl, benzyl or substituted benzyl group.

Claim 9

Dependent Claim 40 words

The coating composition as claimed in Claim 6, wherein in the photoinitiator compound of the formula (IV), R 3 , R4 and R 5 are independently a hydroxyalkyl group having 1-8 carbon atoms or a phenyl or substituted phenyl group.

Claim 10

Dependent Claim 19 words

The coating composition as claimed in Claim 7, wherein the photoinitiator compound (b-1) is trimethylbenzoyldipheylphosphine oxide or benzoyldiethoxyphosphine oxide.

Claim 11

Dependent Claim 46 words

The coating composition as claimed in Claim 1, wherein the photoinitiator (B) is a mixture of (b-1) the photoinitiator compound and (b-2) another photoinitiator compound, and the peak of sensitive wavelengths of said other photoinitiator compound (b-2) is between 200-365 nm, the latter wavelength being exclusive.

Claim 12

Dependent Claim 27 words

The coating composition as claimed in Claim 9, wherein the photoinitiator compounds (b-1) and (b-2) are mixed at a ratio satisfying the following relationship: (b-1) ≧ (b-2)

Claim 13

Dependent Claim 30 words

A molded plastic article having a hardened coating on the surface thereof, said coating is formed by coating the ultraviolet-curing composition according to claim 1 and then irradiating ultraviolet rays.

Claim 14

Dependent Claim 169 words

A process for the production of a molded plastic article having a hardened coating of modified surface characteristics, which comprises: i) sandwiching between a molded plastic article and a synthetic resin film an ultraviolet curing coating composition comprising as principal components: (A) 100 parts by weight of a photopolymerizable composition composed of (a-1) 50-100 wt.% of a cross linking-polymerizable compound containing at least two acryloyloxy or methacryloyloxy groups per molecule and (a-2) 0-50 wt.% of another compound copolymerizable with the crosslinking-polymerizable compound (a-1); (B) 0.02-10 parts by weight of a photoinitiator comprising a photoinitiator compound (b-1), the peak of sensitive wavelengths of said photoinitiator compound (b-1) being between 365-400 nm; and (C) 0.1-15 parts by weight of an ultraviolet absorber; ii) bringing the coating composition into close contact with the molded plastic article; iii) exposing the coating composition to ultraviolet rays to cure the coating composition, thereby forming the hardened coating on the molded plastic article; and then iv) peeling off the synthetic resin film from the hardened coating.

Claim 15

Dependent Claim 169 words

A process for the production of a molded plastic article having a hardened coating of modified surface characteristics, which comprises: i) sandwiching between a molded plastic article and a synthetic resin film an ultraviolet curing coating composition comprising as principal components: (A) 100 parts by weight of a photopolymerizable composition composed of (a-1) 50-100 wt.% of a cross linking-polymerizable compound containing at least two acryloyloxy or methacryloyloxy groups per molecule and (a-2) 0-50 wt.% of another compound copolymerizable with the crosslinking-polymerizable compound (a-1); (B) 0.02-10 parts by weight of a photoinitiator comprising a photoinitiator compound (b-1), the peak of sensitive wavelengths of said photoinitiator compound (b-1) being between 365-400 nm; and (C) 0.1-15 parts by weight of an ultraviolet absorber; ii) bringing the coating composition into close contact with the molded plastic article; iii) exposing the coating composition to ultraviolet rays to cure the coating composition, thereby forming the hardened coating on the molded plastic article; and then iv) peeling off the synthetic resin film from the hardened coating.

Claim 16

Dependent Claim 64 words

The process as claimed in Claim 11, wherein the hardened coating is formed to satisfy the following formula (V): 0.07;5 x·d ≦ 0.58 (V) wherein d is the thickness of the hardened coating as expressed in terms of µm, and x is the amount, as expressed in terms of mole, of the ultraviolet absorber (C) added per 100 g of the photopolymerizable composition (A).

Claim 17

Dependent Claim 26 words

The process as claimed in Claim 11, wherein the base polymer forming the molded plastic article is a polymethyl methacrylate resin, polycarbonate resin or polymethacrylimide resin.

Claim 18

Dependent Claim 72 words

The process as claimed in Claim 13, wherein the crosslinking-polymerizable compound (a-1) comprises a compound represented by the following formula (I): wherein n is an integer of 1-4, at least three of Xs are independently a 0- group, m stands for an integer of 0-2, R' means a hydrogen atom or methyl group and R 2 denotes an alkylene group having 1-6 carbon atoms, and any remaining X is an OH group.

Claim 19

Dependent Claim 37 words

The process as claimed in Claim 13, wherein the crosslinking-polymerizable compound comprises a polyacrylate and/or polymethacrylate of a saturated or unsaturated polyester obtained by reacting a polyhydric alcohol, a polycarboxylic acid, and acrylic acid and/or methacrylic acid.

Claim 20

Dependent Claim 65 words

The process as claimed in Claim 13, wherein the crosslinking-polymerizable compound comprises a urethane polyacrylate or urethane polymethacrylate obtained by reacting a polyisocyanate represented by the following formula (II): wherein R is an alkylene group having 1-10 carbon atoms or a phenylene, substituted phenylene or diphenylene group, with a compound containing at least one acryloyloxy or methacryloyloxy group and at least one active hydrogen atom.

Claim 21

Dependent Claim 78 words

The process as claimed in claim 13, wherein the crosslinking-polymerizable compound comprises a urethane polyacrylate or polymethacrylate represented by the following formula (IV): wherein R 6 means a (meth)acryloyloxy group, R 7 denotes a hydrogen atom or methyl group, R 8 is a phenylene group, a substituted phenylene group or an alkylene group having 2-6 carbon atoms, and Q is in which p and q are individually an integer of 1-8 and y is an integer of 0-10.

Claim 22

Dependent Claim 66 words

The coating composition as claimed in Claim 13, wherein the crosslinking-polymerizable compound (a-1) is a mixture of 0-75 wt.% of a compound containing at least two acryloyloxy or methacryloyloxy groups and having a viscosity higher than 150 cps at 20 C and 25-100 wt.% of another compound containing two or three acryloyloxy or methacryloyloxy groups and having a viscosity not higher than 150 cps at 20°C.

Claim 23

Dependent Claim 49 words

The process as claimed in Claim 13, wherein the photoinitiator compound (b-1) is represented by the following formula (III): wherein R 3 , R 4 and R 5 mean independently an alkyl or oxyalkyl group having 1-8 carbon atoms or a phenyl, substituted phenyl, benzyl or substituted benzyl group.

Claim 24

Dependent Claim 40 words

The process as claimed in Claim 21, wherein in the photoinitiator compound of the formula (III), R 3 , R 4- and R 5 are independently a hydroxyalkyl group having 1-8 carbon atoms or a phenyl or substituted phenyl group.

Claim 25

Dependent Claim 18 words

The process as claimed in Claim 22, wherein the photoinitiator compound (b-1) is trimethylbenzoyldipheylphosphine oxide or benzoyldiethoxyphosphine oxide.

Claim 26

Dependent Claim 45 words

The process as claimed in Claim 13, wherein the photoinitiator (B) is a mixture of (b-1) the photoinitiator compound and (b-2) another photoinitiator compound, and the peak of sensitive wavelengths of said other photoinitiator compound (b-2) is between 200-365 nm, the latter wavelength being exclusive.

Claim 27

Dependent Claim 26 words

The process as claimed in Claim 24, wherein the photoinitiator compounds (b-1) and (b-2) are mixed at a ratio satisfying the following relationship: (b-1) ≧ (b-2)

Ultraviolet-curing coating composition and production process of molded plastic article having hardened coating of modified surface characteristics

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