Patent US4092170A successfully refreshed from Google Patents.
US4092170A
Expired / Lapsed
US
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Photocopying materials
Assignee: Canon Production Printing Holding BV
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Filing: 1976-02-17
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Granted: 1978-05-30
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Expires: 1996-02-17
Abstract
Abstract A photocopying material is provided having a light-sensitive layer comprising an oleophilic resin and a resinous diazonium compound, which both are soluble in an organic solvent but substantially insoluble in water, in admixture with a surface active agent which, after imagewise exposure, renders the layer developable with plain water such as ordinary tap water so as to yield an excellent photocopy and in particular a printing form from which many thousands of fine prints can be made on an offset machine.
Inventors
- 👤 Antonius H. I. Houtermans
- 👤 Johannes G. Kamphuis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 15:01
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/016; G03F7/0166; G03C; G03C1/00; G03C1/52; G03C1/61
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
257 words
Photocopying material comprising a support carrying a light-sensitive layer which consists essentially of a negative-working, light-sensitive diazonium resin salt and an oleophilic, filmforming resin, both of which are soluble in organic solvents and at most sparingly soluble in water, and at least 10% by weight of water-soluble surfactant which renders said diazonium resin salt soluble in water so that said layer is developable into an image by plain water after imagewise exposure of said layer to light; said resin salt being selected from the group consisting of p-toluene sulfonic acid, napththalene-2-sulfonic acid, BF4- and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazo-diphenylamine and formaldehyde; said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR4## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR5## R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. water-soluble quaternary ammonium salts of the general formula ##STR6## wherein R 1 and R 2 each is a methylol or ethylol group, R 3 is hydrogen or a methylol or ethylol group, and R 4 is an alkyl chain having 9-18 carbon atoms; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 2
Dependent Claim
257 words
Photocopying material comprising a support carrying a light-sensitive layer which consists essentially of a negative-working, light-sensitive diazonium resin salt and an oleophilic, filmforming resin, both of which are soluble in organic solvents and at most sparingly soluble in water, and at least 10% by weight of water-soluble surfactant which renders said diazonium resin salt soluble in water so that said layer is developable into an image by plain water after imagewise exposure of said layer to light; said resin salt being selected from the group consisting of p-toluene sulfonic acid, napththalene-2-sulfonic acid, BF4- and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazo-diphenylamine and formaldehyde; said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR4## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR5## R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. water-soluble quaternary ammonium salts of the general formula ##STR6## wherein R 1 and R 2 each is a methylol or ethylol group, R 3 is hydrogen or a methylol or ethylol group, and R 4 is an alkyl chain having 9-18 carbon atoms; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 3
Dependent Claim
53 words
Photocopying material according to claim 1, comprising in the light-sensitive layer as said surfactant water-soluble alkyl-quaternary ammonium salt of the general formula ##STR7## in which R is a hydrocarbon chain, which salt comprises predominantly at least one compound of said formula wherein R is an alkyl group having 12 to 18 carbon atoms.
Claim 4
Dependent Claim
57 words
Photocopying material according to claim 1 comprising in the light-sensitive layer as said surfactant water-soluble quaternary ammonium salt of the general formula ##STR8## wherein R 1 and R 2 each is a methylol or ethylol group, R 3 is H or a methylol or ethylol group, and R 4 is an alkyl chain having 9-18 carbon atoms.
Claim 5
Dependent Claim
20 words
Photocopying material according to claim 3 comprising in the light-sensitive layer as said surfactant diethanolamine laurylsulphate or triethanol amine laurylsulphate.
Claim 6
Dependent Claim
16 words
Photocopying material according to claim 1 comprising in the light-sensitive layer as said surfactant a polyvinylpyrrolidone.
Claim 7
Dependent Claim
17 words
Photocopying material according to claim 1 comprising in the light-sensitive layer 30-40 wt % of said surfactant.
Claim 8
Dependent Claim
28 words
Photocopying material according to claim 1 comprising in the light-sensitive layer as said diazonium resin salt the naphthalene-2-sulphonic acid salt of the condensation product of p-diazo-diphenylamine and formaldehyde.
Claim 9
Dependent Claim
18 words
Photocopying material according to claim 1 comprising in the light-sensitive layer as said oleophilic resin an epoxy resin.
Claim 10
Dependent Claim
249 words
Light-sensitive composition for the production of photocopy material, consisting essentially of a solution in an organic solvent of a negative-working light-sensitive diazonium resin salt and an oleophilic filmforming resin, each of which is soluble in organic solvents and at most sparingly soluble in water, and at least 10% by weight, calculated on the dissolved dry matter, of water-soluble surfactant which renders said diazonium resin salt soluble in water, said resin salt being selected from the group consisting of p-toluene sulfonic acid, napththalene-2-sulfonic acid, BF4-and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazo-diphenylamine and formaldehyde; said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR9## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR10## in which R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. water-soluble quaternary ammonium salts of the general formula ##STR11## wherein R 1 and R 2 each is a methylol or ethylol group, R 3 is hydrogen or a methylol or ethylol group and R 4 is an alkyl chain having 9-18 carbon atoms; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 11
Dependent Claim
249 words
Light-sensitive composition for the production of photocopy material, consisting essentially of a solution in an organic solvent of a negative-working light-sensitive diazonium resin salt and an oleophilic filmforming resin, each of which is soluble in organic solvents and at most sparingly soluble in water, and at least 10% by weight, calculated on the dissolved dry matter, of water-soluble surfactant which renders said diazonium resin salt soluble in water, said resin salt being selected from the group consisting of p-toluene sulfonic acid, napththalene-2-sulfonic acid, BF4-and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazo-diphenylamine and formaldehyde; said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR9## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR10## in which R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. water-soluble quaternary ammonium salts of the general formula ##STR11## wherein R 1 and R 2 each is a methylol or ethylol group, R 3 is hydrogen or a methylol or ethylol group and R 4 is an alkyl chain having 9-18 carbon atoms; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 12
Dependent Claim
17 words
Light-sensitive coating composition according to claim 9, further comprising several percent of a co-solvent for the surfactant.
Claim 13
Dependent Claim
20 words
Light-sensitive coating composition according to claim 10 comprising an alcohol having 5-7 carbon atoms in the molecule as said co-solvent.
Claim 14
Dependent Claim
12 words
Light-sensitive coating composition according to claim 10 comprising 4-methyl-2-pentanol as said co-solvent.
Claim 15
Dependent Claim
233 words
Photocopying material for producing an offset printing plate, comprising a support carrying a light-sensitive layer consisting essentially of negative-working light-sensitive diazonium resin salt selected from the group consisting of naphththalene-2-sulfonic acid, BF 4 - and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazodiphenylamine and formaldehyde, oleophilic filmforming epoxy resin and at least 10% by weight of water-soluble surfactant that renders said resin salt soluble in water, said resin salt and said epoxy resin being present in a weight ratio, resin salt to resin, of between 0.3 and 4 to 1, the quantity of said surfactant being sufficient to render said layer developable into an image by plain water after imagewise exposure of said layer to light, said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR12## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR13## in which R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. diethanolamine and triethanolamine dodecyl sulfates; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 16
Dependent Claim
233 words
Photocopying material for producing an offset printing plate, comprising a support carrying a light-sensitive layer consisting essentially of negative-working light-sensitive diazonium resin salt selected from the group consisting of naphththalene-2-sulfonic acid, BF 4 - and 1-chloro-4-benzene sulfonic acid salts of the condensation product of p-diazodiphenylamine and formaldehyde, oleophilic filmforming epoxy resin and at least 10% by weight of water-soluble surfactant that renders said resin salt soluble in water, said resin salt and said epoxy resin being present in a weight ratio, resin salt to resin, of between 0.3 and 4 to 1, the quantity of said surfactant being sufficient to render said layer developable into an image by plain water after imagewise exposure of said layer to light, said surfactant being selected from the group consisting of: a. alkyl-quaternary ammonium salts of the general formula ##STR12## in which R represents a hydrocarbon chain, which salts comprise predominantly at least one compound of formula I wherein R is an alkyl chain having 12 to 18 carbon atoms; b. ethylene oxide amines of the general formula ##STR13## in which R represents an alkyl chain, which amines comprise at least one compound of formula II wherein the alkyl chain has 18 carbon atoms and the sum of x and y is 15; c. diethanolamine and triethanolamine dodecyl sulfates; d. sodium and sodium-2-ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate; and e. polyvinyl pyrrolidone surfactants.
Claim 17
Dependent Claim
18 words
Photocopying material according to claim 13, said layer containing about 30 to 40% by weight of said surfactant.
Claim 18
Dependent Claim
63 words
Photocopying material according to claim 13, said light-sensitive layer having been formed by coating and drying on said support a solution of said resin salt, said epoxy resin and said surfactant in a solvent consisting essentially of methylene glycol with up to about 20% by weight of water and a small amount of 2-methyl-1-butanol or 4-methyl-1-pentanol sufficient to aid dissolution of said surfactant.
Claim 19
Dependent Claim
27 words
Photocopying material according to claim 15, said resin salt being the naphthalene-2-sulfonic acid salt of said condensation product and said surfactant being a diethanolamine or triethanolamine dodecylsulfate.
Claim 20
Dependent Claim
59 words
Photocopying material according to claim 13, said light-sensitive layer having been formed by coating and drying on said support a solution of said resin salt and said epoxy resin in a solvent consisting essentially of methylene glycol with up to about 20% by weight of water and thereafter applying to the dried coating an aqueous solution of said surfactant.
Claim 21
Dependent Claim
28 words
Photocopying material according to claim 17, said surfactant being selected from the group consisting of sodium and sodium-2 -ethyl dodecyl sulfates, sodium decyl sulfate and sodium tridecyl sulfate.
Claim 22
Dependent Claim
47 words
Photoconductive material according to claim 13, said light-sensitive layer having been formed by coating and drying on said support a solution of said resin salt, said epoxy resin and said surfactant in a solvent consisting essentially of methylene glycol with up to 20% by weight of water.
Claim 23
Dependent Claim
13 words
Photocopying material according to claim 19, said surfactant being a polyvinyl pyrrolidone surfactant.
Claim 24
Dependent Claim
26 words
Photocopying material according to claim 19, said resin salt being the naphthalene-2-sulfonic acid salt of said condensation product and said surfactant being a polyvinyl pyrrolidone surfactant.
References Cited (Backward Citations)
GB1280885A
Cited
US3679419A
Cited
US3751257A
Cited
US3790382A
Cited
US3790556A
Cited
US3847614A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-29 | 1981-11-28 | 1982-05-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-29 | 1985-11-28 | 1986-05-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-29 | 1989-11-28 | 1990-05-30 | $7700.00 | Window Closed / Lapsed |