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US 5,601,971 AGranted
Hardening of hydrophilic colloids with imidazolium and triazine combinations
AssigneeSterling Diagnsotic Imaging, Inc.
InventorsLudovic Fodor, Richard R. M. Jones, Reinhold R uger, Timothy D. Weatherill, Rolf T. Weberg
Life of this patent
Estimating the term…
Abstract
An improved method of hardening a hydrophilic colloid is detailed. The hardening results in a stronger matrix and less water pickup. These and other advantages are obtained by hardening with a combination of at least one hardener chosen from Formula I either alone or in combination with at least one hardener chosen from Formula II: ##STR1## The substituents are defined.
Claims28
A photographic element comprising a silver halide containing photosensitive layer wherein a first hydrophilic colloid layer is hardened with 0.01 to 1.0 millimoles per gram of hydrophilic colloid of at least one imidazolium compound of formula:
- ##STR18## wherein:
- Y.sup.1 is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- --L.sup.1 CR.sup.8 CH.sub.2 or a polymer thereof;
- --C(Y.sup.4)E;
- or ##STR19## E is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.9 ;
- --CN;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- L.sup.1 is a linking group;
- R.sup.1 is hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.10 ;
- halogen;
- nitro;
- carboxyl;
- mercapto;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- R.sup.2 and R.sup.3 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- or aralkyl of 7 to 25 carbons;
- or R.sup.2 and R.sup.3 independently represent, or are taken together to represent, a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- R.sup.4 and R.sup.5 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- nitro;
- carboxyl;
- mercapto;
- --OR.sup.11 ;
- halogen;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- or R.sup.4 and R.sup.5 taken together represent a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- X.sup.- is a counterion;
- Y.sup.2, Y.sup.3 and Y.sup.4 independently represent O or S;
- R.sup.6 and R.sup.7 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- or R.sup.6 and R.sup.7 taken together represent the atoms chosen from C, N, O and S necessary to form a 5- or 6-member ring;
- R.sup.8 represents a hydrogen;
- alkyl of 1 to 24 carbons;
- --C(O)R.sup.28 ;
- --CN;
- or aryl of 6 to 24 carbons;
- R.sup.9 represents hydrogen;
- alkyl of 1 to 24 carbons;
- or aryl of 6 to 24 carbons;
- R.sup.10 and R.sup.11 independently represent hydrogen or alkyl of 1 to 5 carbons;
- and
- R.sup.28 represents hydrogen;
- alkyl of 1 to 24 carbons;
- alkoxy of 1 to 24 carbons;
- amine;
- or alkylamine of 1 to 24 carbons.
62 more elements
A process for forming a photographic element, comprising:
- forming at least one liquid photographic emulsion in at least one storage vessel wherein said liquid photographic emulsion comprises silver halide, hydrophilic colloid and a solvent;
- transporting said liquid photographic emulsion to an injection region;
- injecting into said liquid photographic emulsion in said injection region at least one imidazolium compound defined by ##STR27## wherein:
- Y.sup.1 is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- --L.sup.1 CR.sup.8 CH.sub.2 or a polymer thereof;
- --C(Y.sup.4)E;
- or ##STR28## E is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.9 ;
- --CN;
- or a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- L.sup.1 is a linking group;
- R.sup.1 is hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.10 ;
- halogen;
- nitro;
- carboxyl;
- mercapto;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- R.sup.2 and R.sup.3 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- or R.sup.2 and R.sup.3 independently represent, or are taken together to represent, a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- R.sup.4 and R.sup.5 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- nitro;
- carboxyl;
- mercapto;
- --OR.sup.11 ;
- halogen;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- or R.sup.4 and R.sup.5 taken together represent a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- X.sup.- is a counterion;
- Y.sup.2, Y.sup.3 and Y.sup.4 independently represent O or S;
- R.sup.6 and R.sup.7 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- or a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- or R.sup.6 and R.sup.7 taken together represent a 5- or 6-membered ring containing atoms chosen from a set consisting of C, N, O, and S;
- R.sup.8 represents a hydrogen;
- an alkyl of 1 to 24 carbons;
- --C(O)R.sup.28 ;
- --CN;
- or an aryl of 6 to 24 carbons;
- R.sup.9 represents hydrogen;
- alkyl of 1 to 24 carbons;
- or aryl of 6 to 24 carbons;
- R.sup.10 and R.sup.11 independently represent hydrogen, or an alkyl of 1 to 5 carbons;
- and
- R.sup.28 represents hydrogen;
- alkyl of 1 to 24 carbons;
- alkoxy of 1 to 24 carbons;
- amine;
- or alkylamine of 1 to 24 carbons;
- transporting said liquid photographic emulsion to a coater;
- coating said liquid photographic emulsion on a substrate;
- and
- removing said solvent from said liquid photographic emulsion to form a dry coated emulsion layer.
68 more elements
A photographic element comprising a silver halide containing photosensitive layer and at least one hydrophilic colloid layer hardened with at least one imidazolium compound of formula:
- ##STR37## wherein:
- Y.sup.1 is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- --L.sup.1 CR.sup.8 CH.sub.2 or a polymer thereof;
- --C(Y.sup.4)E;
- or ##STR38## E is an alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.9 ;
- --CN;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- L.sup.1 is a linking group;
- R.sup.1 is hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- --OR.sup.10 ;
- halogen;
- nitro;
- carboxyl;
- mercapto;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- R.sup.2 and R.sup.3 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- or R.sup.2 and R.sup.3 taken together represent a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- R.sup.4 and R.sup.5 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- nitro;
- carboxyl;
- mercapto;
- --OR.sup.11 ;
- halogen;
- alkylamino of 1 to 24 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- or R.sup.4 and R.sup.5 taken together represent a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- X.sup.- is a counterion;
- Y.sup.2, Y.sup.3 and Y.sup.4 independently represent O or S;
- R.sup.6 and R.sup.7 independently represent hydrogen;
- alkyl of 1 to 24 carbons;
- aryl of 6 to 24 carbons;
- aralkyl of 7 to 25 carbons;
- or a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- or R.sup.6 and R.sup.7 taken together represent a 5- or 6-membered ring containing atoms chosen from the group consisting of C, N, O, and S;
- R.sup.8 represents a hydrogen;
- alkyl of 1 to 24 carbons;
- --C(O)R.sup.28 ;
- --CN;
- or aryl of 6 to 24 carbons;
- R.sup.9 represents hydrogen;
- alkyl of 1 to 24 carbons;
- or aryl of 6 to 24 carbons;
- R.sup.10 and R.sup.11 independently represent hydrogen or alkyl of 1 to 5 carbons;
- and
- R.sup.28 represents hydrogen;
- alkyl of 1 to 24 carbons;
- alkoxy of 1 to 24 carbons;
- amine;
- or alkylamine of 1 to 24 carbons;
- and
- said at least one hydrophilic colloid layer, or at least another hydrophilic colloid layer, is hardened by at least one triazine compound defined by:
- ##STR39## wherein:
- at least two of R.sup.12, R.sup.13 and R.sup.14 are independently chosen from the group consisting of halogen;
- ##STR40## one of R.sup.12, R.sup.13 and R.sup.14 represents hydrogen;
- alkyl of 1 to 24 carbons;
- halogen;
- --OR.sup.21 ;
- --NR.sup.22 R.sup.23 ;
- --OM;
- a divalent linking group to another triazine compound;
- sulfonamide;
- alkylether of 1 to 20 carbons;
- polyethylene oxide of 2 to 40 carbons;
- --(OR.sup.24).sub.x R.sup.25 ;
- or --L.sup.2 CR.sup.26 CH.sub.2 or a polymer thereof;
- R.sup.15 and R.sup.16 independently represent sodium;
- potassium;
- ammonium;
- alkyl ammonium of 1 to 20 carbons;
- hydrogen;
- or alkyl of 1 to 20 carbons;
- R.sup.17 and R.sup.18 independently represent sodium;
- potassium;
- ammonium;
- hydrogen;
- alkyl ammonium of 1 to 20 carbons;
- or alkyl of 1 to 20 carbons;
- R.sup.19 and R.sup.20 independently represent sodium;
- potassium;
- hydrogen;
- ammonium;
- alkyl ammonium of 1 to 20 carbons;
- or alkyl of 1 to 20 carbons;
- R.sup.21 represents hydrogen;
- alkyl of 1 to 20 carbons;
- alkoxyalkyl of 1 to 40 carbons;
- aryl of 6 to 40 carbons;
- aralkyl of 7 to 41 carbons;
- or alkylthioether of 1 to 40 carbons;
- R.sup.22 and R.sup.23 independently represent hydrogen;
- alkyl of 1 to 20 carbons;
- aryl of 6 to 20 carbons;
- alkylether of 1 to 20 carbons;
- arylether of 6 to 20 carbons;
- alkylthioether of 1 to 20 carbons;
- arylthioether of 6 to 20 carbons;
- sulfonyl;
- or alkylsulfonyl of 1 to 20 carbons;
- R.sup.24 represents an ethylene;
- R.sup.25 represents an alkyl of 1 to 20 carbons;
- or an ether of 1 to 20 carbons;
- R.sup.26 represents a hydrogen or alkyl of 1 to 24 carbons;
- L.sup.2 is a chemical linkage;
- M is a counterion;
- and
- x is an integer from 1 to 24.
120 more elements
Dependencies are inferred from the claim text.