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 Method of hardening gelatin using sulfonyl compounds

Details
Inventors: Sera, Hidefumi; Nagao, Kameji; Ishii, Tsumoru;
Assignee: Fujii Photo Film Co., Ltd. (Minami-ashigara, JA)
Primary Examiner: Schain; Howard E.
Assistant Examiner:
Attorney, Agent or Firm: Sughrue, Rothwell, Mion, Zinn & Macpeak

A method of hardening gelatin which comprises adding thereto a compound of the following general formula (I): ##STR1## in which Y.sub.1 is CH.sub.2 =CH--, ClCH.sub.2 --CH.sub.2 --, BrCH.sub.2 --CH.sub.2 --, CH.sub.3 COO--CH.sub.2 CH.sub.2 -- or ClCH.sub.2 COO--CH.sub.2 CH.sub.2 --, R.sub.1 and R.sub.2 are H or CH.sub.3, but both of them are not CH.sub.3 at the same time, and A is one of the following groups: ##STR2## in which both R.sub.3 and R.sub.4 were acyl groups or at least one of them is an acyl group other than when R.sub.3 and R.sub.4 form a benzotriazole ring, and when one of R.sub.3 and R.sub.4 is an acyl group, the other is H or an alkyl group containing at most 4 carbon atoms; and wherein in any case, R.sub.3 and R.sub.4 may form a saturated or unsaturated carbocyclic or heterocyclic ring in combination with the nitrogen atom to which they are attached; R.sub.5, R.sub.6 and R.sub.7 are alkyl groups containing at most 4 carbon atoms, and may form a saturated or unsaturated ring, or may form a bicyclo ring; X.sup.- is an acid anion; R.sub.8 and R.sub.9 are a saturated or unsaturated carbocyclic or heterocyclic ring which combine with the nitrogen atom to which they are attached; R.sub.10 is an alkyl or aryl group containing at most 6 carbon atoms; R.sub.11 is an alkyl group containing at most 3 carbon atoms; R.sub.12 is an alkyl, aryl or aralkyl group containing at most 7 carbons atoms; Y.sub.2 is CH.sub.2 =CH--, ClCH.sub.2 --CH.sub.2 --, Br--CH.sub.2 CH.sub.2 --, CH.sub.3 COO--CH.sub.2 CH.sub.2 --, or ClCH.sub.2 COO--CH.sub.2 CH.sub.2 --, and Y.sub.1 is as earlier defined.

DETAILED DESCRIPTION What is claimed is: 1.
A method of hardening gelatin which comprises adding thereto a compound of the following general formula (I): ##STR6## in which Y.
sub.
1 is CH.
sub.
2 =CH--, ClCH.
sub.
2 --CH.
sub.
2 --, BrCH.
sub.
2 --CH.
sub.
2 --, CH.
sub.
3 COO--CH.
sub.
2 CH.
sub.
2 -- or ClCH.
sub.
2 COO--CH.
sub.
2 CH.
sub.
2 --, R.
sub.
1 and R.
sub.
2 are H or CH.
sub.
3, but both of them are not CH.
sub.
3 at the same time, and A is one of the following groups: ##STR7## in which both R.
sub.
3 and R.
sub.
4 are acyl groups or at least one of them is an acyl group other than when R.
sub.
3 and R.
sub.
4 form a benzotriazole ring, and when one or R.
sub.
3 and R.
sub.
4 is an acyl group, the other is H or an alkyl group containing at most 4 carbon atoms; and wherein in any case, R.
sub.
3 and R.
sub.
4 may form a saturated or unsaturated carbocyclic or heterocyclic ring in combination with the nitrogen atom to which they are attached; R.
sub.
5, R.
sub.
6 and R.
sub.
7 are alkyl groups containing at most 4 carbon atoms, and may form a saturated or unsaturated ring, or may form a bicyclo ring; X.
sup.
- is an acid anion; R.
sub.
8 and R.
sub.
9 are a saturated or unsaturated carbocyclic or heterocyclic ring in combination with the nitrogen atom to which they are attached; R.
sub.
10 is an alkyl or aryl group containing at most 6 carbon atoms; R.
sub.
11 is an alkyl group containing at most 3 carbon atoms; R.
sub.
12 is an alkyl, aryl or aralkyl group containing at most 7 carbon atoms; and Y.
sub.
2 is CH.
sub.
2 =CH--, ClCH.
sub.
2 --CH.
sub.
2 --, Br--CH.
sub.
2 --CH.
sub.
2 --, CH.
sub.
3 COO--CH.
sub.
2 CH.
sub.
2 --, or ClCH.
sub.
2 COO--CH.
sub.
2 CH.
sub.
2 --.
2.
The method of claim 1, wherein R.
sub.
8 and R.
sub.
9 are residues which form succinimide, maleninimide or phthalimide in combination with the nitrogen atom to which they are attached.
3.
The method of claim 1, wherein in general formula I.
y.
sub.
1 is CH.
sub.
2 =CH-- or ClCH.
sub.
2 CH.
sub.
2 --, R.
sub.
1 and R.
sub.
2 are H, and A is either 1, 2 or 3 given below: ##STR8## where R.
sub.
3 -R.
sub.
9 and X



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