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US4017652A Expired / Lapsed US ⏱️ 0.0 years remaining

Photocatalyst system and ultraviolet light curable coating compositions containing the same

Assignee: PPG Industries Inc
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Filing: 1974-10-23
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Granted: 1977-04-12
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Expires: 1994-10-23
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Abstract

Abstract The oxygen inhibition of the photopolymerization of acrylic resins is reduced by employing a photocatalyst system containing an aromatic ketone and/or aromatic aldehyde photosensitizer having a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole and which promotes polymerization through bimolecular photochemical reactions of the energy donor type and an aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation. An exemplary photocatalyst system is benzophenone and isobutyl benzoin ether.

Inventors

  • 👤 Gerald W. Gruber

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 17:05
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C08K; C08K5/00; C08K5/04; C08K5/07; C09; C09D; C09D163/00; C09D163/10

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 38 words
A photocatalyst system comprising a. at least one aromatic ketone or aromatic aldehyde photosensitizer which 1. has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and 2.
Claim 2
Dependent Claim 38 words
A photocatalyst system comprising a. at least one aromatic ketone or aromatic aldehyde photosensitizer which 1. has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and 2.
Claim 3
Dependent Claim 99 words
promotes polymerization bimolecular photochemical reactions of the energy donor type; and b. at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one member of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxybenzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylolbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin
Claim 4
Dependent Claim 99 words
promotes polymerization bimolecular photochemical reactions of the energy donor type; and b. at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one member of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxybenzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylolbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin
Claim 5
Dependent Claim 64 words
ether, and mixtures thereof. 2. The photocatalyst system of claim 1 wherein said photosensitizer is present in an amount in the range of from about 25 percent to about 90 percent by weight of said photocatalyst system and wherein said photoinitiator is present in an amount in the range of from about 10 percent to about 75 percent by weight of said photocatalyst system.
Claim 6
Dependent Claim 11 words
The photocatalyst system of claim 2 wherein said photosensitizer is benzophenone.
Claim 7
Dependent Claim 13 words
The photocatalyst system of claim 3 wherein said photoinitiator is isobutyl benzoin ether.
Claim 8
Dependent Claim 19 words
The photocatalyst system of claim 3 wherein said photoinitiator is a mixture of butyl isomers of butyl benzoin ether.
Claim 9
Dependent Claim 171 words
A ultraviolet high curable coating composition comprising: a. at least one aromatic ketone or aromatic aldehyde photosensitizer which 1.has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and 2. promotes photopolymerization through bimolecular photochemical reactions of the energy donor type; b. at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one number of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxy-benzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylolbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin ether, and mixtures thereof; and c. a resin having acrylic unsaturation and capable of being free radially addition polymerized by interaction with said photosensitizer and said photoinitiator upon exposure to ultraviolet light.
Claim 10
Dependent Claim 171 words
A ultraviolet high curable coating composition comprising: a. at least one aromatic ketone or aromatic aldehyde photosensitizer which 1.has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and 2. promotes photopolymerization through bimolecular photochemical reactions of the energy donor type; b. at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one number of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxy-benzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylolbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin ether, and mixtures thereof; and c. a resin having acrylic unsaturation and capable of being free radially addition polymerized by interaction with said photosensitizer and said photoinitiator upon exposure to ultraviolet light.
Claim 11
Dependent Claim 96 words
The ultraviolet light curable coating composition of claim 6 wherein: a. said photosensitizer is present in an amount in the range of from about 0.01 percent to about 50 percent by weight of the binder of said coating composition; b. said photoinitiator is present in an amount in the range of from about 0.01 percent to about 10 percent by weight of the binder of said coating composition; and c said resin is present in an amount in the range of from about 20 to 100 percent by weight of the binder of said coating composition.
Claim 12
Dependent Claim 14 words
The ultraviolet light curable coating composition of claim 7 wherein said photosensitizer is benzophenone.
Claim 13
Dependent Claim 16 words
The ultraviolet light curable coating composition of claim 8 wherein said photoinitiator is isobutyl benzoin ether.
Claim 14
Dependent Claim 22 words
The ultraviolet light curable coating composition of claim 8 wherein said photoinitiator is a mixture of butyl isomers of butyl benzoin ether.
Claim 15
Dependent Claim 34 words
The ultraviolet light coating composition of claim 7 wherein monoacrylic functional monomer is present in the range of from about 0 to about 80 percent by weight of the binder of said coating composition.
Claim 16
Dependent Claim 41 words
The ultraviolet light curable coating composition of claim 7 wherein extender pigment which is generally transparent to ultraviolet light is present in an amount in the range of from about 0 to about 70 percent by weight of said coating composition.
Claim 17
Independent Claim 60 words
A method comprising: a. coating a substrate with an ultraviolet light curable coating composition comprising 1. at least one aromatic ketone or aromatic aldehyde photosensitizer which a. has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and b. promotes polymerization through bimolecular photochemical reactions of the energy donor type,
Claim 18
Independent Claim 60 words
A method comprising: a. coating a substrate with an ultraviolet light curable coating composition comprising 1. at least one aromatic ketone or aromatic aldehyde photosensitizer which a. has a triplet energy in the range of from about 54 kilocalories per mole to about 72 kilocalories per mole, and b. promotes polymerization through bimolecular photochemical reactions of the energy donor type,
Claim 19
Dependent Claim 140 words
at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one member of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxybenzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin ether, and mixtures thereof, and 3. a resin having acrylic unsaturation and capable of being free radically addition polymerized by interaction with said photosensitizer and said photoinitiator upon exposure to ultraviolet light; and b. exposing said coated substrate to ultraviolet light to cure said coating into a hard mar and abrasion resistant film.
Claim 20
Dependent Claim 140 words
at least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation, at least one member of said radical pair being capable of initiating addition polymerization of acrylic groups, said aromatic ketone photoinitiator being selected from the group consisting of ethyl benzoin ether, isopropyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophone, α, α-dimethoxy-α-phenylacetophenone, 4,4'-dicarboethoxybenzoin ethyl ether, benzoin phenyl ether, α-methylbenzoin ethyl ether, α-methylbenzoin methyl ether, α, α, α-trichloroacetophenone, mixtures of butyl isomers of butyl benzoin ether, and mixtures thereof, and 3. a resin having acrylic unsaturation and capable of being free radically addition polymerized by interaction with said photosensitizer and said photoinitiator upon exposure to ultraviolet light; and b. exposing said coated substrate to ultraviolet light to cure said coating into a hard mar and abrasion resistant film.
Claim 21
Dependent Claim 91 words
The method of claim 13 wherein: a. said photosensitizer is present in an amount in the range of from about 0.01 percent to about 50 percent by weight of the binder of said coating composition; b. said photoinitiator is present in an amount in the range from about 0.01 percent to about 10 percent by weight of the binder of said coating composition; and c. said resin is present in an amount in the range of from about 20 to 100 percent by weight of the binder of said coating composition.
Claim 22
Dependent Claim 10 words
The method of claim 14 wherein said photosensitizer is benzophenone.
Claim 23
Dependent Claim 12 words
The method of claim 15 wherein said photoinitiator is isobutyl benzoin ether.
Claim 24
Dependent Claim 18 words
The method of claim 15 wherein said photoinitiator is a mixture of butyl isomers of butyl benzoin ether.
Claim 25
Dependent Claim 25 words
The photocatalyst system of claim 1 wherein said photoinitiator is selected from the group consisting of α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone and mixtures thereof.
Claim 26
Dependent Claim 28 words
The ultraviolet light curable coating composition of claim 1 wherein said photoinitiator is selected from the group consisting of α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone and mixtures thereof.
Claim 27
Dependent Claim 24 words
The method of claim 13 wherein said photoinitiator is selected from the group consisting of α, α-diethoxyacetophenone, α, α-diethoxy-α-phenylacetophenone, α, α-dimethoxy-α-phenylacetophenone and mixtures thereof.

References Cited (Backward Citations)

US3368900A Cited
US3427161A Cited
US3824284A Cited
US3759807A Cited
US3756827A Cited
US3825479A Cited
US3827960A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-04-11 1980-10-11 1981-04-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-04-11 1984-10-11 1985-04-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-04-11 1988-10-11 1989-04-12 $7700.00 Window Closed / Lapsed

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