US4052373A
Expired / Lapsed
US
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Process for hardening gelatin
Assignee: Fujifilm Holdings Corp
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Filing: 1975-06-05
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Granted: 1977-10-04
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Expires: 1995-06-05
Abstract
Abstract A process for hardening, e.g., gelatin, in particular, a gelatin used for photographic light-sensitive materials, which comprises treating gelatin, a non-gelatin hydrophilic high molecular weight material containing primary or secondary amino groups or a composition containing the same with a compound represented by the following general formula (I): ##STR1## WHEREIN R 1 and R 2 , which may be the same or different, each represents a monovalent residue which is bonded through a carbon atom or a sulfur atom thereof to the nitrogen atom forming the carboxylic acid ester, and R 1 and R 2 may combine to form a ring structure; R is a divalent or trivalent residue which is bonded through a carbon atom or a nitrogen atom thereof to the carbon atom of the carboxyl group in the carboxylic acid ester, and n is 2 when R is a divalent residue and n is 3 when R is a trivalent residue.
Inventors
- 👤 Hidefumi Sera
- 👤 Nobuo Yamamoto
- 👤 Ikutaro Horie
- 👤 Kameji Nagao
- 👤 Nobuyuki Iwasaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 06:17
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/005; G03C1/06; G03C1/30
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
191 words
A process for hardening gelatin or a hydrophilic non-gelatin high molecular weight material containing primary and/or secondary amino groups selected from polyethyleneamine, poly(ethylene-4-amino-1,2,4-triazole, β-aminoacrylic acid-ethylene-maleic acid copolymers and vinylamine-acrylic acid copolymers which comprises adding to the gelatin or the high molecular weight material a compound represented by the following general formula (I): ##STR14## wherein R 1 and R 2 , which may be the same or different, each represents a monovalent residue which is bended through a carbon atom or a sulfur atom thereof to the nitrogen atom forming the carboxylic acid ester, and R 1 and R 2 may combine to form a ring structure; R is a divalent or trivalent residue which is bonded through a carbon atom or a nitrogen atom thereof to the carbon atom of the carboxyl group in the carboxylic acid ester; and n is 2 when R is a divalent residue and n is 3 when R is a trivalent residue, wherein the amount of said compound of general formula (I) is from about 0.1% to 10% be weight based on the weight of dry gelatin or the hydrophilic non-gelatin high molecular weight material.
Claim 2
Dependent Claim
191 words
A process for hardening gelatin or a hydrophilic non-gelatin high molecular weight material containing primary and/or secondary amino groups selected from polyethyleneamine, poly(ethylene-4-amino-1,2,4-triazole, β-aminoacrylic acid-ethylene-maleic acid copolymers and vinylamine-acrylic acid copolymers which comprises adding to the gelatin or the high molecular weight material a compound represented by the following general formula (I): ##STR14## wherein R 1 and R 2 , which may be the same or different, each represents a monovalent residue which is bended through a carbon atom or a sulfur atom thereof to the nitrogen atom forming the carboxylic acid ester, and R 1 and R 2 may combine to form a ring structure; R is a divalent or trivalent residue which is bonded through a carbon atom or a nitrogen atom thereof to the carbon atom of the carboxyl group in the carboxylic acid ester; and n is 2 when R is a divalent residue and n is 3 when R is a trivalent residue, wherein the amount of said compound of general formula (I) is from about 0.1% to 10% be weight based on the weight of dry gelatin or the hydrophilic non-gelatin high molecular weight material.
Claim 3
Dependent Claim
74 words
The process as claimed in claim 1, wherein R 2 is a ##STR15## group or an --R 4 group when R 1 represents a ##STR16## group, wherein R 3 and R 4 , which may be the same or different, each represents a monovalent residue, and R 3 and R 4 may combine to form a 5- or 6-membered mononuclear ring, an 8- to 13-membered condensed ring or a ring containing a bridging group.
Claim 4
Dependent Claim
45 words
The process as claimed in claim 1, wherein R in the general formula (I) represents a divalent or trivalent residue of a straight or branched chain, a 5- or 6-membered mononuclear ring, a 7- to 10-membered condensed ring or a ring containing a bridging group.
Claim 5
Dependent Claim
48 words
The process as claimed in claim 1, wherein ##STR17## in the general formula (I) is selected from the group consisting of 1-pyrazolyl, 1,2,3-benzotriazol-1-yl, 1,2,3-naphthotriazol-1-yl, phthalimido, Δ 1 -tetrahydrophthalimido, cyclohexane, 1,2-dicarboximido, dicarboximido, 5-norbornene-2,3-dicarboximido, succinimido, maleimido, glutarimido, 6-carboxy-1,2,3-benzotriazol-1-yl, 6-sulfo-1,2,3-benzotriazol-1-yl, 5-chloro-1,2,3-benzotriazol-1-yl, 4-carboxyphthalimido, 4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl, sulfosuccinimido and aspartimido, and the position isomers thereof.
Claim 6
Dependent Claim
22 words
The process as claimed in claim 4, wherein ##STR18## in the general formula (I) is a 1,2,3-benzotriazol-1-yl group or a 4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl group.
Claim 7
Dependent Claim
60 words
The process as claimed in claim 1, wherein R in the general formula (I) is selected from the group consisting of methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, propylene, 1,2-dimethylethylene, vinylene, methyleneethylene, ethynylene, propenylene, p-phenylene, 1,3,5-benzenetriyl, 1,2,4,5-benzenetetrayl, 1,4-cyclohexanediyl, 1,3-cyclopentanediyl, (1,3-cyclohexanediyl)dimethylene, dioxane-2,6-diyl, pyridine-3,5-diyl, tetramethylenediimino, hexamethylenediimino, (1,4-cyclohexanediyl)diimino, 2-methyl-2-azatrimethylene, oxybis(methyleneimino), (1,4-diazoniabicyclo[2,2,2]octane-1,4-diyl)-dimethylene, oxydimethylene, oxydiethylene, 5-carboxy-1,3-phenylene, 2-sulfo-1,4-phenylene and 2-sulfo-1,4-cyclohexanediyl, and the position isomers thereof.
Claim 8
Dependent Claim
25 words
The process as claimed in claim 1, wherein the compound represented by the general formula (I) is: N,N'-adipoyldioxydi(5-norbornene-2,3-dicarboxylic acid imide), N,N'-adipoyldioxydisuccinimide, 1,1'-adipoyldioxydi(1,2,3-benzotriazole), N,N'-hexamethylenebis(iminocarbonyloxy)disuccinimide or N,N'N"-(1,3,5-benezenetriyl)tris(carbonyloxy)triphthalimide.
Claim 9
Dependent Claim
20 words
The process as claimed in claim 1, wherein the compound represented by the general formula (I) is N,N'-adipoyldioxydisuccinimide or N,N'-hexamethylenebis(iminocarbonyloxy)disuccinimide.
Claim 10
Dependent Claim
25 words
The process as claimed in claim 1, wherein said process comprises treating gelatin or a gelatin-containing composition with said compound having the general formula (I).
Claim 11
Dependent Claim
40 words
The process as claimed in claim 9, wherein the amount of the compound represented by the general formula (I) to the gelatin is an amount of about 0.5 to 5% by weight based on the weight of the dry gelatin.
Claim 12
Dependent Claim
36 words
The process according to claim 1, wherein said monovalent residue represented by R 1 and R 2 is an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl.
Claim 13
Dependent Claim
30 words
The process according to claim 1, wherein when R 1 and R 2 combine to form a ring structure said rings include 1-piperidinyl, morpholino, 2-pyrrolidon-1-yl, succinimido, 1,2,3-benzotriazol-1-yl, 4-oxo-3,4-dihydro-1,2,3-benzothiazin-3-yl and 5-norbornene-2,3-dicarboximido.
Claim 14
Dependent Claim
37 words
The process of claim 1, wherein R is an alkylene group, an arylene group, or a divalent group selected from the class consisting of divalent groups containing one or more hetero atoms from oxygen, nitrogen and/or sulfur.
Claim 15
Dependent Claim
39 words
The process as claimed in claim 1, wherein when R 1 and R 2 combine to form a ring structure the ring structure includes one or more atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
Claim 16
Dependent Claim
41 words
The process as claimed in claim 2, wherein when R 3 and R 4 combine to form a 5- or 6-membered mononuclear ring said ring contains one or more atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
Claim 17
Dependent Claim
25 words
The process as claimed in claim 2, wherein said ring is selected from the group consisting of 1-piperidinyl, morpholino, 2-pyrrolidon-1-yl, succinimido, 1,2,3-benzotriazol-1yl, 4-oxo-3,4-dihydro-1,2,3-benzothiazin-3-yl and 5-norbornene-2,3-dicarboximido.
References Cited (Backward Citations)
US3770451A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-03 | 1981-04-04 | 1981-10-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-03 | 1985-04-04 | 1985-10-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-03 | 1989-04-04 | 1989-10-04 | $7700.00 | Window Closed / Lapsed |