US4233391A
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US
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Water developable photopolymerizable compositions containing phosphine activators and saponified polyvinyl acetate
Assignee: Napp Systems USA Inc
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Filing: 1979-08-27
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Granted: 1980-11-11
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Expires: 1999-08-27
Abstract
Abstract A photopolymerizable composition and photosensitive elements produced therefrom are disclosed. The photopolymerizable composition includes: (a) a monomer component, (b) a polymer component, (c) a photopolymerization initiator, and (d) an activator. The monomer component contains at least one water soluble, monofunctional unsaturated ethylenic monomer or the combination of such a monomer and at least one polyfunctional unsaturated ethylenic monomer. The polymer component includes a partially saponified water soluble, polyvinyl acetate polymer compatible with the monomer components. The polyvinyl acetate polymer contains both acetyl and hydroxyl groups and has a polymerization degree of from 300-2000. The degree of saponification of the polymer is desirably in the range of 65 to 99 percent. The preferred photopolymerization initiators are acetophenone derivatives such as 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy-2-phenyl acetophenone, 2,-2-diisopropoxy-2-phenyl acetophenone, benzoin alkyl, aryl, allyl or vinyl ethers, or benzophenone derivatives such as benzophenone, 2-methylbenzophenone, 2-methoxybenzophenone or 2,2'-dimethoxybenzophenone, which are compatible with the monomer component and the polyvinyl acetate polymer and are activatable by actinic light. Finally, the activator is a phosphine derivative generally described by the formula: ##STR1## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, vinyl, or allyl, although not more than one or X, Y and Z may be hydrogen. It is especially preferred in the practice of the present invention that at least one of X, Y and Z in the phosphine derivative activator component be an aryl group.
Inventors
- 👤 Sakuo Okai
- 👤 Koichi Kimoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 21:19
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106; Y10S430/11; Y10S430/114; Y10S430/118
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
218 words
A photopolymerizable composition for water developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of the total composition of a monomer component including at least one water-soluble, monofunctional unsaturated ethylenic monomer, or the combination of said monofunctional monomer and at least one polyfunctional unsaturated ethylenic monomer, said monomers capable of forming a polymer by photoinitiated polymerization in the presence of a polymerization initiator activatable by actinic light: b. about 0.1 to 3.0 parts by weight of the total composition of a polymer component including a partially saponified, water-soluble, polyvinyl acetate polymer compatible with said monomer component containing both acetyl and hydroxy groups, and having a polymerization degree of about 300 to 2,000 and a saponification degree of about 65 to 99 mole percent; c. about 0.001 to 0.3 parts by weight of the total composition of a photopolymerization initiator compatible with said monomer component and said polyvinyl acetate polymer, and activatable by actinic light; and, d. about 0.001 to 0.3 parts by weight of the total composition of an activator including a phosphine derivative described by the formula: ##STR3## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, vinyl or allyl and at least one of X, Y and Z is aryl.
Claim 2
Dependent Claim
218 words
A photopolymerizable composition for water developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of the total composition of a monomer component including at least one water-soluble, monofunctional unsaturated ethylenic monomer, or the combination of said monofunctional monomer and at least one polyfunctional unsaturated ethylenic monomer, said monomers capable of forming a polymer by photoinitiated polymerization in the presence of a polymerization initiator activatable by actinic light: b. about 0.1 to 3.0 parts by weight of the total composition of a polymer component including a partially saponified, water-soluble, polyvinyl acetate polymer compatible with said monomer component containing both acetyl and hydroxy groups, and having a polymerization degree of about 300 to 2,000 and a saponification degree of about 65 to 99 mole percent; c. about 0.001 to 0.3 parts by weight of the total composition of a photopolymerization initiator compatible with said monomer component and said polyvinyl acetate polymer, and activatable by actinic light; and, d. about 0.001 to 0.3 parts by weight of the total composition of an activator including a phosphine derivative described by the formula: ##STR3## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, vinyl or allyl and at least one of X, Y and Z is aryl.
Claim 3
Dependent Claim
30 words
A photopolymerizable composition according to claim 1 wherein said polymerization initiator is an acetophenone derivative selected from the group consisting of 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy-2-phenyl acetohenone, 2,2-diisopropoxy-2-phenyl acetophenone, and 2,2-di-n-butoxy-2-phenyl acetophenone.
Claim 4
Dependent Claim
217 words
A photopolymerizable composition for water-developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of a monomer component including at least one water-soluble monofunctional monomer, or the combination of said monofunctional monomer and at least one polyfunctional unsaturated ethylenic monomer, said monomers capable of forming a polymer by photoinitiated polymerization in the presence of a polymerization initiator activatable by actinic light; b. about 0.1 to 3.0 parts by weight of a water soluble polymer component including a partially saponified, water-soluble, polyvinyl acetate polymer compatible with said monomer component containing both acetyl and hydroxy groups, and having a polymerization degree of about 300 to 2,000 and a saponification degree of about 65 to 99 mole percent; c. about 0.001 to 0.3 parts by weight of a photopolymerization initiator said initiator being compatible with said monomer component and said polyvinyl acetate polymer, and activatable by actinic light; and d. about 0.001 to 0.3 parts by weight of an activator including a phosphine derivative described by the formula: ##STR4## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, allyl, or vinyl, but not more than one of the X, Y and Z is hydrogen, and at least one of X, Y and Z is aryl.
Claim 5
Dependent Claim
217 words
A photopolymerizable composition for water-developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of a monomer component including at least one water-soluble monofunctional monomer, or the combination of said monofunctional monomer and at least one polyfunctional unsaturated ethylenic monomer, said monomers capable of forming a polymer by photoinitiated polymerization in the presence of a polymerization initiator activatable by actinic light; b. about 0.1 to 3.0 parts by weight of a water soluble polymer component including a partially saponified, water-soluble, polyvinyl acetate polymer compatible with said monomer component containing both acetyl and hydroxy groups, and having a polymerization degree of about 300 to 2,000 and a saponification degree of about 65 to 99 mole percent; c. about 0.001 to 0.3 parts by weight of a photopolymerization initiator said initiator being compatible with said monomer component and said polyvinyl acetate polymer, and activatable by actinic light; and d. about 0.001 to 0.3 parts by weight of an activator including a phosphine derivative described by the formula: ##STR4## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, allyl, or vinyl, but not more than one of the X, Y and Z is hydrogen, and at least one of X, Y and Z is aryl.
Claim 6
Dependent Claim
35 words
A photopolymerizable composition according to claim 3 wherein said activator is selected from the group consisting of triphenyl phosphine, o-tolyl diphenyl phosphine, di-(o-tolyl)phenyl phosphine, tri-(o-tolyl)phosphine, o-methoxyphenyl diphenyl phosphine, o-ethylphenyl diphenyl phosphine, and o-chlorophenyl diphenyl phosphine.
Claim 7
Dependent Claim
22 words
A photopolymerizable composition according to claim 3 wherein said initiator is selected from the group consisting of benzoin, acetophenone and benzophenone derivatives.
Claim 8
Dependent Claim
46 words
A photopolymerizable composition according to claim 5 wherein said photopolymerization initiator is selected from the group consisting of benzoin isopropyl ether, benzoin isobutyl ether, benzoin vinyl ether, benzoin aryl ether, benzoin allyl ether, 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy-2-phenyl acetophenone, 2,2-diiso propoxy-2-phenyl-acetophenone, 2,2-di-n-butoxy-2-phenyl acetophenone, benzophenone, 2-methoxybenzophenone, 2-methylbenzophenone and 2,2'-dimethoxybenzophenone.
Claim 9
Dependent Claim
55 words
The photopolymerizable composition of claim 3 wherein said partially saponified polyvinyl acetate polymer comprises one or more partially saponified polyvinyl acetate polymers having different degrees of saponification, where the arithmetic average of the different saponification degrees, based upon the weight percent of each polymer, is within the range of about 65 to 99 mole percent.
Claim 10
Dependent Claim
28 words
The photopolymerizable composition according to claim 7 wherein said polyvinyl acetate polymers have different degrees of polymerization, said degrees of polymerization ranging from about 300 to about 2,000.
Claim 11
Dependent Claim
34 words
A photopolymerizable composition of claim 3 wherein said monomer component is monofunctional monomer selected from the group consisting of an acrylic or methacrylic ester of a lower alkanol having at least one hydroxy group.
Claim 12
Dependent Claim
66 words
The photopolymerizable composition of claim 3 wherein said monomer component includes at least one water-soluble monofunctional unsaturated ethylenic monomer and at least one polyfunctional monomer selected from the group consisting of acrylic or methacrylic esters of a polyethylene glycol having the structural formula [HO(CH 2 CH 2 O)nH] and, n, the number of ethylene oxide units in said polyethylene glycol ester, being between one and twenty-three.
Claim 13
Dependent Claim
52 words
A photopolymerizable composition according to claim 10, wherein said monofunctional monomer is selected from the group consisting of B-hydroxyethyl acrylate, B-hydroxyethyl methacrylate, B-hydroxypropyl acrylate, B-hydroxypropyl methacrylate, and said polyfunctional monomer is selected from the group consisting of polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, glycol dimethacrylate, pentaerythritol dimethacrylate, trimethylolethane trimethacrylate and tetramethylolmethane tetramethacrylate.
Claim 14
Dependent Claim
33 words
A photopolymerizable composition according to claim 3 wherein said monomer component includes one more of the following monomer components either alone or in combination: pentaerythritol dimethacrylate, trimethylolpropane trimethacrylate, tetramethylolmethane tetramethacrylate, and trimethylolethane trimethacrylate.
Claim 15
Dependent Claim
30 words
A photopolymerizable composition according to claim 3 further comprising about 0.01 to 0.3 percent by weight of a thermal polymerization inhibitor, based upon the weight of said unsaturated ethylenic monomers.
Claim 16
Dependent Claim
13 words
The photopolymerizable composition according to claim 13 further containing small amounts of dyestuffs.
Claim 17
Dependent Claim
150 words
A water-developable photopolymerizable composition for water-developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of at least one unsaturated ethylenic monomer polymerizable by actinic light in the presence of a photopolymerization initiator; b. about 0.001 to 0.3 parts by weight of a photopolymerization initiator c. about 0.1 to 3.0 parts by weight of a water soluble partially saponified polyvinyl acetate having both acetyl groups and hydroxy groups produced by saponification, said polyvinyl acetate having a saponification degree of about 65 to 99 mole percent and a polymerization degree of about 300 to 2,000, and d. about 0.001 to 0.3 parts by weight of a phosphine derivative described by the formula: ##STR5## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, allyl, or vinyl, and at least one of X, Y and Z is aryl.
Claim 18
Dependent Claim
150 words
A water-developable photopolymerizable composition for water-developable printing plates which can be exposed and developed without pre-exposure conditioning comprising: a. about 0.1 to 3.0 parts by weight of at least one unsaturated ethylenic monomer polymerizable by actinic light in the presence of a photopolymerization initiator; b. about 0.001 to 0.3 parts by weight of a photopolymerization initiator c. about 0.1 to 3.0 parts by weight of a water soluble partially saponified polyvinyl acetate having both acetyl groups and hydroxy groups produced by saponification, said polyvinyl acetate having a saponification degree of about 65 to 99 mole percent and a polymerization degree of about 300 to 2,000, and d. about 0.001 to 0.3 parts by weight of a phosphine derivative described by the formula: ##STR5## wherein any of X, Y and Z are hydrogen, halogen, alkyl, alkoxy, aryl, allyl, or vinyl, and at least one of X, Y and Z is aryl.
Claim 19
Dependent Claim
44 words
The water developable photopolymerizable composition of claim 15 wherein said initiator is an acetophenone derivative and said activator is selected from the group consisting of triphenyl phosphine, o-tolyl diphenyl phosphine, di-(o-tolyl)phenyl phosphine, tri-(o-tolyl)phosphine, o-methoxyphenyl diphenyl phosphine, o-ethyl phenyl diphenyl phosphine, and o-chlorophenyl diphenyl phosphine.
Claim 20
Dependent Claim
56 words
The water developable polymerizable composition of claim 16 wherein said unsaturated ethylenic monomer is the combination of ethyleneglycol dimethacrylate and B-hydroxypropyl methacrylate, said water soluble polymer is the combination of two partially saponified polyvinyl acetate polymers having saponification degrees of 77 and 82 mole percent respectively, said initiator is 2,2-dimethoxy-2-phenyl acetophenone, and said activator is triphenylphosphine.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |