US4393094A — Stabilization of electron beam curable compositio…

Claim 1

Independent Claim 166 words

A coating composition polymerizable by low dosage ionizing radiation, which comprises an organic resin/monomer mixture of: (A) between about 97 and about 3 weight percent alpha-beta olefinically unsaturated organic resin containing between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said resin; and (B) between about 3 and about 97 weight percent vinyl monomers polymerizable with said resin upon exposure to radiation, said vinyl monomers including N-vinyl-2-pyrrolidone in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B); and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR11## wherein R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amine having the formula: ##STR12## wherein R=H or methyl.

Claim 2

Dependent Claim 166 words

A coating composition polymerizable by low dosage ionizing radiation, which comprises an organic resin/monomer mixture of: (A) between about 97 and about 3 weight percent alpha-beta olefinically unsaturated organic resin containing between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said resin; and (B) between about 3 and about 97 weight percent vinyl monomers polymerizable with said resin upon exposure to radiation, said vinyl monomers including N-vinyl-2-pyrrolidone in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B); and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR11## wherein R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amine having the formula: ##STR12## wherein R=H or methyl.

Claim 3

Dependent Claim 27 words

A coating composition according to claim 1, wherein said R 1 or R 2 of said benzotriazole is an alkyl group of C 3 -C 9 .

Claim 4

Dependent Claim 18 words

A coating composition according to claims 1 or 2, wherein said R of said hindered amine is hydrogen.

Claim 5

Dependent Claim 15 words

A coating composition according to claim 1, wherein said benzotriazole is a mixture of benzotriazoles.

Claim 6

Dependent Claim 19 words

A coating composition according to claims 1 or 4, wherein said hindered amine is a mixture of hindered amines.

Claim 7

Dependent Claim 34 words

A coating composition according to claim 1, wherein said benzotriazole is present in said composition in a weight amount (i) in excess of said hindered amine, or (ii) about equal to said hindered amine.

Claim 8

Dependent Claim 34 words

A coating composition according to claim 1, wherein said composition further comprises between 5 and about 12 parts by weight per 100 parts of the total of said (A) and (B) of micronized polyethylene.

Claim 9

Dependent Claim 28 words

A coating composition according to claim 1, wherein said resin contains between about 0.5 and about 3 vinyl unsaturation units per 1000 units molecular weight of said resin.

Claim 10

Dependent Claim 32 words

A coating composition according to claim 1, wherein said resin comprises a urethane acrylic oligomer having the formula: ##STR13## wherein R' is hydrogen or methyl and Y is a divalent urethane residue.

Claim 11

Dependent Claim 33 words

A coating composition according to claim 1, wherein said N-vinyl-2-pyrrolidone is included in an amount of between about 3 and about 10 weight percent based on the total weight of (A) and (B).

Claim 12

Dependent Claim 21 words

A coating composition according to claim 9, wherein said vinyl monomers other than said N-vinyl-2-pyrrolidone consist essentially of acrylic ester monomers.

Claim 13

Dependent Claim 17 words

A coating composition according to claim 9 or 11, wherein said R' of said oligomer is hydrogen.

Claim 14

Dependent Claim 20 words

A coating composition according to claim 9, wherein said oligomer has a molecular weight between about 400 and about 10,000.

Claim 15

Dependent Claim 23 words

A coating composition according to claim 11, wherein said acrylic ester monomers comprise at least 70 weight percent of monovinyl acrylic ester monomers.

Claim 16

Dependent Claim 23 words

A coating composition according to claim 14, wherein said acrylic ester monomers comprise greater than 80 weight percent of monovinyl acrylic ester monomers.

Claim 17

Dependent Claim 34 words

A coating composition according to claim 14, wherein said monovinyl acrylic ester monomers are selected from the group consisting essentially of ethoxyethyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, glycidyl acrylate and mixtures thereof.

Claim 18

Dependent Claim 39 words

A coating composition according to claim 14 or 16, wherein said acrylic ester monomer, other than said monovinyl acrylic ester monomer, is selected from the group consisting of 1,6-hexanediol diacrylate, tetraethylene glycol diacrylate, trimethylol propane triacrylate and mixtures thereof.

Claim 19

Dependent Claim 211 words

A 100% solids coating composition polymerizable by low dosage ionizing radiation adapted to coat flexible substrates, which exclusive of pigments, initiators and other non-reactive components, consists essentially of an oligomer/monomer mixture of: (A) between about 90 and about 10 weight percent oligomer having the formula: ##STR14## wherein R' is hydrogen or methyl; and Y is a divalent urethane residue; and said oligomer has between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said oligomer; and (B) between about 10 and about 90 weight percent vinyl monomers polymerizable with said oligomer upon exposure to radiation, said vinyl monomers consisting essentially of (i) acrylic ester monomers and (ii) N-vinyl-2-pyrrolidone, wherein said N-vinyl-2-pyrrolidone is included in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B), and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR15## where R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amines having the formula: ##STR16## wherein R=H or methyl.

Claim 20

Dependent Claim 211 words

A 100% solids coating composition polymerizable by low dosage ionizing radiation adapted to coat flexible substrates, which exclusive of pigments, initiators and other non-reactive components, consists essentially of an oligomer/monomer mixture of: (A) between about 90 and about 10 weight percent oligomer having the formula: ##STR14## wherein R' is hydrogen or methyl; and Y is a divalent urethane residue; and said oligomer has between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said oligomer; and (B) between about 10 and about 90 weight percent vinyl monomers polymerizable with said oligomer upon exposure to radiation, said vinyl monomers consisting essentially of (i) acrylic ester monomers and (ii) N-vinyl-2-pyrrolidone, wherein said N-vinyl-2-pyrrolidone is included in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B), and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR15## where R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amines having the formula: ##STR16## wherein R=H or methyl.

Claim 21

Dependent Claim 29 words

A 100% solids coating composition according to claim 18, wherein said R 1 or R 2 of said benzotriazole is an alkyl group of C 3 -C 9 .

Claim 22

Dependent Claim 20 words

A 100% solids coating composition according to claims 18 or 19, wherein said R of said hindered amine is hydrogen.

Claim 23

Dependent Claim 17 words

A 100% solids coating composition according to claim 18, wherein said benzotriazole is a mixture of benzotriazoles.

Claim 24

Dependent Claim 21 words

A 100% solids coating composition according to claims 18 or 21, wherein said hindered amine is a mixture of hindered amines.

Claim 25

Dependent Claim 36 words

A 100% solids coating composition according to claim 18, wherein said benzotriazole is present in said composition in a weight amount (i) in excess of said hindered amine, or (ii) about equal to said hindered amine.

Claim 26

Dependent Claim 36 words

A 100% solids coating composition according to claim 18, wherein said composition further comprises between 5 and about 12 parts by weight per 100 parts of the total of said (A) and (B) of micronized polyethylene.

Claim 27

Dependent Claim 35 words

A 100% solids coating composition according to claim 24, wherein said N-vinyl-2-pyrrolidone is included in an amount of between about 3 and about 10 weight percent based on the total weight of (A) and (B).

Claim 28

Dependent Claim 17 words

A 100% solids coating composition according to claim 24, wherein said R' of said oligomer is hydrogen.

Claim 29

Dependent Claim 25 words

A 100% solids coating composition according to claim 24 or 16, wherein said oligomer has a molecular weight of between about 400 and about 5000.

Claim 30

Dependent Claim 24 words

A 100% solids coating composition according to claim 24, wherein said acrylic ester monomers comprise at least 70 weight percent monovinyl acrylic ester monomers.

Claim 31

Dependent Claim 24 words

A 100% solids coating composition according to claim 28, wherein said acrylic ester monomers comprise greater than 80 weight percent monovinyl acrylic ester monomers.

Claim 32

Dependent Claim 36 words

A 100% solids coating composition according to claim 28, wherein said monovinyl acrylic ester monomers are selected from the group consisting essentially of ethoxyethyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, glycidyl acrylate and mixtures thereof.

Claim 33

Dependent Claim 40 words

A 100% solids coating composition according to claim 24 or 30, wherein said acrylic ester monomers, other than said monovinyl acrylic ester monomers, are selected from the group consisting of 1,6-hexanediol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate and mixtures thereof.

Claim 34

Independent Claim 267 words

A method for coating a substrate, the coating composition polymerizable by low dosage ionizing radiation, which comprises: (A) applying a first coating composition comprising up to about 60 weight percent pigment to the surface of a prepared substrate; (B) curing said first coating composition by exposure to an electron beam until an adherent dry coating is formed; (C) applying a second coating composition comprising 0-10 weight percent pigment to the coated surface of said substrate; and (D) curing said second coating composition by exposure to an electron beam until an adherent dry coating is formed; wherein said first coating composition and said second coating composition comprises an organic resin/monomer mixture of: (A) between about 97 and about 3 weight percent alpha-beta olefinically unsaturated organic resin containing between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said resin; and (B) between about 3 and about 97 weight percent vinyl monomers polymerizable with said resin upon exposure to radiation, said vinyl monomers comprising N-vinyl-2-pyrrolidone which is included in said composition in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B); and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR17## where R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amines having the formula: ##STR18## wherein R=H or methyl.

Claim 35

Independent Claim 267 words

A method for coating a substrate, the coating composition polymerizable by low dosage ionizing radiation, which comprises: (A) applying a first coating composition comprising up to about 60 weight percent pigment to the surface of a prepared substrate; (B) curing said first coating composition by exposure to an electron beam until an adherent dry coating is formed; (C) applying a second coating composition comprising 0-10 weight percent pigment to the coated surface of said substrate; and (D) curing said second coating composition by exposure to an electron beam until an adherent dry coating is formed; wherein said first coating composition and said second coating composition comprises an organic resin/monomer mixture of: (A) between about 97 and about 3 weight percent alpha-beta olefinically unsaturated organic resin containing between about 0.5 and about 5 vinyl unsaturation units per 1000 units molecular weight of said resin; and (B) between about 3 and about 97 weight percent vinyl monomers polymerizable with said resin upon exposure to radiation, said vinyl monomers comprising N-vinyl-2-pyrrolidone which is included in said composition in an amount of between about 3 and about 20 weight percent based on the total weight of (A) and (B); and (C) about 0.5 to about 5.0 parts each per 100 parts of the total of said organic resin and said monomer of: (i) benzotriazole selected from the group consisting of compounds having the formula: ##STR17## where R 1 or R 2 =H or an alkyl group of C 1 -C 25 ; and (ii) hindered amine selected from the group consisting of amines having the formula: ##STR18## wherein R=H or methyl.

Claim 36

Dependent Claim 30 words

A method for coating a substrate according to claim 32, wherein said R 1 or R 2 of said benzotriazole is an alkyl group of C 3 -C 9 .

Claim 37

Dependent Claim 21 words

A method for coating a substrate according to claim 32 or 33, wherein said R of said hindered amine is hydrogen.

Claim 38

Dependent Claim 18 words

A method for coating a substrate according to claim 32, wherein said benzotriazole is a mixture of benzotriazoles.

Claim 39

Dependent Claim 22 words

A method for coating a substrate according to claim 32 or 35, wherein said hindered amine is a mixture of hindered amines.

Claim 40

Dependent Claim 37 words

A method for coating a substrate according to claim 32, wherein said benzotriazole is present in said composition in a weight amount (i) in excess of said hindered amine, or (ii) about equal to said hindered amine.

Claim 41

Dependent Claim 34 words

A coating composition according to claim 32, wherein said composition further comprises between 5 and about 12 parts by weight per 100 parts of the total of said (A) and (B) of micronized polyethylene.

Claim 42

Dependent Claim 35 words

A method for coating a substrate according to claim 32, wherein said resin comprises a urethane acrylic oligomer having the formula: ##STR19## wherein R' is hydrogen or methyl and Y is a divalent urethane residue.

Claim 43

Dependent Claim 38 words

A method for coating a substrate according to claim 32 or 39, wherein said N-vinyl-2-pyrrolidone is included in an amount of between about 3 and about 10 weight percent based on the total weight of (A) and (B).

Claim 44

Dependent Claim 18 words

A method for coating a substrate according to claim 39, wherein said R' of said oligomer is hydrogen.

Claim 45

Dependent Claim 24 words

A method for coating a substrate according to claim 39, wherein said oligomer has a molecular weight of between about 400 and about 10,000.

Claim 46

Dependent Claim 24 words

A method for coating a substrate according to claim 39, wherein said vinyl monomers other than said N-vinyl-2-pyrrolidone consist essentially of acrylic ester monomers.

Claim 47

Dependent Claim 26 words

A method for coating a substrate according to claim 43, wherein said acrylic ester monomers comprise at least 70 weight percent of a monovinyl acrylic ester.

Claim 48

Dependent Claim 40 words

A method for coating a substrate according to claim 44, wherein said monovinyl acrylic ester monomers are selected from the group consisting of ethoxyethyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, glycidyl acrylate, ethoxyethyl methacrylate, glycidyl methacrylate and mixtures thereof.

Claim 49

Dependent Claim 39 words

A method for coating a substrate according to claim 45, wherein said acrylic ester monomers other than said monovinyl acrylic ester monomers, are selected from the group consisting of 1,6-hexanediol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate and mixtures thereof.

Claim 50

Dependent Claim 18 words

A method for coating a substrate according to claim 32, wherein said substrate is comprised of polyvinyl chloride.

Claim 51

Dependent Claim 18 words

A method for coating a substrate according to claim 45, wherein said substrate is flexible polyvinyl chloride fabric.

Claim 52

Dependent Claim 23 words

A method for coating a substrate according to claim 47, wherein said first coating composition and said second coating composition are 100% solids.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1986-07-11	1987-01-10	1987-07-12	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1990-07-11	1991-01-10	1991-07-12	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1994-07-11	1995-01-10	1995-07-12	$7700.00	Window Closed / Lapsed

Stabilization of electron beam curable compositions for improved exterior durability

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