Image reversal negative working O-naphthoquinone diazide and cross-linking compound containing photoresist process with thermal curing

Claim 2

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which comprises in admixture i) from about 1% to about 25% based on the weight of the solid parts of the composition of a photosensitive compound represented by the general formulae (1), (2) or (3): ##STR57## wherein R is H, --X--R b or ##STR58## X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR59## n is 1 or 2, R a is H, --OH, --OY, --OZ, halogen or lower alkyl, with at least one R a radical being --OY and at least one thereof being --OZ, R b is H, alkyl, aryl, substituted alkyl, or substituted aryl; ##STR60## wherein R is H, or ##STR61## Rc is H, --OH, --OY or --OZ, with at least one R c radical being --OY and at least one thereof being --OZ; and ##STR62## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl, R d is --OH, --OY or --OZ with at least one R d radical --OY and at least one thereof being --OZ; wherein Y is 1,2-naphthoquinonediazide 4-sulfonyl and Z is 1,2-naphthoquinonediazide-5-sulfonyl or --W--R 3 , where W is ##STR63## or --SO 2 --, and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a polyvinyl phenol resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted monoclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 --C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --, --CO--, CO 2 --, --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then optionally flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the radiation unexposed non-image areas of said composition from step d) with a developer.

Claim 3

The process of claim 1 wherein the crosslinking compound has the formula ##STR64## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl, or arylalkyl.

Claim 4

The process of claim 1 wherein said crosslinker is dimethylol paracresol or methyl methoxy diphenyl ether.

Claim 5

The process of claim 1 wherein said crosslinker compound is one or more compounds selected from the group consisting of benzene, 1-methoxy-2,6-bis(hydroxymethyl-4-methyl-; phenol, 2,6-bis(methoxymethyl)-4-methyl-; and benzene, 1-methoxy-2,6-bis(methoxymethyl)-4-methyl-.

Claim 6

The process of claim 1 wherein said solvent comprises propylene glycol alkyl ether acetate.

Claim 7

The process of claim 1 wherein said substrate is selected from the group consisting of silicon, aluminum or polymeric resins, silicon dioxide, doped silicon dioxide, silicon nitride, tantalum, copper, polysilicon, ceramics and aluminum/copper mixtures.

Claim 8

The process of claim 1 wherein said composition further comprises one or more compounds selected from the group consisting of colorants, dyes, anti-striation agents, leveling agents, plasticizers, adhesion promoters, speed enhancers, and surfactants.

Claim 9

The process of claim 1 wherein said developer is an aqueous alkaline solution.

Claim 10

The process of claim wherein after step (e) said coated substrate is overall exposed to actinic radiation of from about 200 to about 500 nm.

Claim 11

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture i) from about 1% to about 25% based on the weight of the solid parts of the photosensitive compositions comprising the condensation product of: (I) a phenolic compound selected form the group consisting of: ##STR65## wherein R is H, or --X--R b ; or ##STR66## R a is H, --OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being --OH, X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR67## n is 1 or 2, R b is H, alkyl, aryl, substituted alkyl or substituted aryl; ##STR68## wherein R 2 is H or ##STR69## Rc is H, or --OH with at least two R c radicals being --OH; and ##STR70## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl; (II) a 1,2-naphthoquinonediazide-4-sulfonic acid (Diazo 1); and (III) a 1,2-naphthoquinonediazide-5-sulfonic acid (Diazo 2); and/or an organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR71## or --SO 2 --V, V is halogen, R3 is alkyl, aryl, substituted alkyl, or substituted aryl; wherein the molar ratio of the amount of Diazo 1 reacted to the amount of Diazo 2 and/or organic acid reacted is in the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --, --CO--, CO 2 , --O--CO 2 --, --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the radiation unexposed non-image areas of said composition from step d) with a developer.

Claim 12

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture i) from about 1% to about 25% based on the weight of the solid parts of the photosensitive compositions comprising the condensation product of: (I) a phenolic compound selected form the group consisting of: ##STR65## wherein R is H, or --X--R b ; or ##STR66## R a is H, --OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being --OH, X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR67## n is 1 or 2, R b is H, alkyl, aryl, substituted alkyl or substituted aryl; ##STR68## wherein R 2 is H or ##STR69## Rc is H, or --OH with at least two R c radicals being --OH; and ##STR70## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl; (II) a 1,2-naphthoquinonediazide-4-sulfonic acid (Diazo 1); and (III) a 1,2-naphthoquinonediazide-5-sulfonic acid (Diazo 2); and/or an organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR71## or --SO 2 --V, V is halogen, R3 is alkyl, aryl, substituted alkyl, or substituted aryl; wherein the molar ratio of the amount of Diazo 1 reacted to the amount of Diazo 2 and/or organic acid reacted is in the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --, --CO--, CO 2 , --O--CO 2 --, --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the radiation unexposed non-image areas of said composition from step d) with a developer.

Claim 13

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of i) from about 1% to about 25% based on the weight of the solid parts of the photosensitive compositions comprising the condensation product of: (I) a phenolic compound selected from the group consisting of: ##STR72## wherein R is H, --X--R b or ##STR73## R a is H, --OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being --OH, X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR74## n is 1 or 2, R b is H, alkyl, aryl, substituted alkyl or substituted aryl; ##STR75## wherein R 2 is H, or ##STR76## Rc is H, or --OH with at least two R c radicals being --OH; and ##STR77## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl; (II) a 1,2-naphthoquinonediazide-4-sulfonic acid (Diazo 1); and (III) a 1,2-naphthoquinonediazide-5-sulfonic acid (Diazo 2); and/or an organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR78## or --SO 2 --V, V is halogen, R3 is alkyl, aryl, substituted alkyl, or substituted aryl; wherein the molar ratio of the amount of Diazo 1 reacted to the amount of Diazo 2 and/or organic acid reacted is in the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a polyvinyl phenol resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --,--CO--, CO 2 , --O--CO 2 --, --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a suitable substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then optionally flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the unexposed non-image areas of said composition from step d) with a suitable developer.

Claim 14

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of i) from about 1% to about 25% based on the weight of the solid parts of the photosensitive compositions comprising the condensation product of: (I) a phenolic compound selected from the group consisting of: ##STR72## wherein R is H, --X--R b or ##STR73## R a is H, --OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being --OH, X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR74## n is 1 or 2, R b is H, alkyl, aryl, substituted alkyl or substituted aryl; ##STR75## wherein R 2 is H, or ##STR76## Rc is H, or --OH with at least two R c radicals being --OH; and ##STR77## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl; (II) a 1,2-naphthoquinonediazide-4-sulfonic acid (Diazo 1); and (III) a 1,2-naphthoquinonediazide-5-sulfonic acid (Diazo 2); and/or an organic acid halide represented by the formula: W--R.sub.3 wherein W is ##STR78## or --SO 2 --V, V is halogen, R3 is alkyl, aryl, substituted alkyl, or substituted aryl; wherein the molar ratio of the amount of Diazo 1 reacted to the amount of Diazo 2 and/or organic acid reacted is in the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a polyvinyl phenol resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --,--CO--, CO 2 , --O--CO 2 --, --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a suitable substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then optionally flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the unexposed non-image areas of said composition from step d) with a suitable developer.

Claim 15

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture: i) from about 1% to about 25% based on the weight of a the solid parts of the composition of a photosensitive composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR79## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH, and X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR80## n is 1 or 2; II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo I), and III. A 1,2 naphthoquinonediazide-5-sulfonic acid (Diazo II) or an organic acid of the formula W--R 3 , wherein W is ##STR81## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo I reacted to the amount of Diazo II and/or organic acid reacted is the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula ##STR82## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl or arylalkyl; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the unexposed non-image areas of said composition from step d) with a developer.

Claim 16

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture: i) from about 1% to about 25% based on the weight of a the solid parts of the composition of a photosensitive composition comprising the condensation product of: I. A phenolic compound having the structure: ##STR79## wherein: R a is H, OH, halogen or lower alkyl, with at least two and not greater than six R a radicals being OH, and X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR80## n is 1 or 2; II. A 1,2 naphthoquinonediazide-4-sulfonic acid (Diazo I), and III. A 1,2 naphthoquinonediazide-5-sulfonic acid (Diazo II) or an organic acid of the formula W--R 3 , wherein W is ##STR81## or --SO 2 --V, V is halogen and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; wherein the molar ratio of the amount of Diazo I reacted to the amount of Diazo II and/or organic acid reacted is the range of from about 1:1 to about 39:1; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula ##STR82## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl or arylalkyl; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° to about 100° C. until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the unexposed non-image areas of said composition from step d) with a developer.

Claim 17

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture i) from about 1% to about 25% based on the weight of the solid parts of the composition of a photosensitive compound represented by the general formulae (1), (2) or (3): ##STR83## wherein R is H, --X--R b or ##STR84## X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR85## n is 1 or 2, R a is H, --OH, --OY, --OZ, halogen or lower alkyl, with at least one R a radical being --OY and at least one thereof being --OZ, R b is H, alkyl, aryl, substituted alkyl, or substituted alkyl, or substituted aryl; ##STR86## wherein R is H, or ##STR87## Rc is H, --OH, --OY or --OZ, with at least one R c radical being --OY and at least one thereof being --OZ; and ##STR88## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl, R d is --OH, --OY or --OZ with at least one R d radical --OY and at least one thereof being --OZ; wherein Y is 1,2-naphthoquinonediazide-4-sulfonyl and Z is 1,2-naphthoquinonediazide-5-sulfonyl or --W--R 3 , where W is ##STR89## or --SO 2 --, and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --, --CO--, CO 2 , --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the radiation unexposed non-image areas of said composition form step d) with a developer.

Claim 18

A process for preparing and using a negative working photographic element which comprises in order: a) forming a composition which consists essentially of in admixture i) from about 1% to about 25% based on the weight of the solid parts of the composition of a photosensitive compound represented by the general formulae (1), (2) or (3): ##STR83## wherein R is H, --X--R b or ##STR84## X is a single C--C bond, --O--, --S--, --SO 2 --, ##STR85## n is 1 or 2, R a is H, --OH, --OY, --OZ, halogen or lower alkyl, with at least one R a radical being --OY and at least one thereof being --OZ, R b is H, alkyl, aryl, substituted alkyl, or substituted alkyl, or substituted aryl; ##STR86## wherein R is H, or ##STR87## Rc is H, --OH, --OY or --OZ, with at least one R c radical being --OY and at least one thereof being --OZ; and ##STR88## wherein R 2 is H, alkyl, aryl, substituted alkyl, or substituted aryl, R d is --OH, --OY or --OZ with at least one R d radical --OY and at least one thereof being --OZ; wherein Y is 1,2-naphthoquinonediazide-4-sulfonyl and Z is 1,2-naphthoquinonediazide-5-sulfonyl or --W--R 3 , where W is ##STR89## or --SO 2 --, and R 3 is alkyl, aryl, substituted alkyl or substituted aryl; ii) from about 75% to about 99% based on the weight of the solid parts of the composition of a novolak resin; and iii) from about 0.5% to about 20% based on the weight of the solid parts of the composition of a crosslinking compound which, when in the presence of that amount and strength of the acid generated when said diazide is exposed to actinic radiation, is capable of crosslinking said resin under the application of the heating conditions of step (e), said crosslinking compound has the formula (R.sub.1 O--CHR.sub.3).sub.n --A--(CHR.sub.4 --OR.sub.2).sub.m wherein A has the formula B or B--Y--B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or a oxygen or sulfur containing heterocyclic compound, Y is a single bond, C 1 -C 4 -alkylene or -alkylenedioxy, the chains of which may be interrupted by oxygen atoms, --O--, --S--, --SO 2 --, --CO--, CO 2 , --CONH-- or phenylenedioxy, R 1 and R 2 are H, C 1 -C 6 -alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl; R 3 , R 4 are independently H, C 1 -C 4 -alkyl or substituted or unsubstituted phenyl and n ranges from 1 to 3 and m ranges from 0-3, provided that n+m is greater than 1; and iv) sufficient solvent to dissolve the foregoing composition components; and b) coating said composition on a substrate; and c) heating said coated substrate at a temperature of from about 20° C. to about 100° until substantially all of said solvent is dried off; and d) imagewise exposing said composition to actinic, electron beam, ion beam or x-ray radiation; and e) heating said coated substrate at a temperature of at least about 95° C. to about 160° C. for from about 10 seconds or more to crosslink said resin; then flood exposing the composition overall to actinic radiation in the range of from about 200 to about 500 nm in an amount sufficient to react said coating; and f) removing the radiation unexposed non-image areas of said composition form step d) with a developer.

Claim 19

The process of claim 13 where the crosslinking compound has the formula ##STR90## wherein R 1 , R 4 , R 5 , R 6 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl, arylalkyl or OR 2 ; and R 2 , R 3 are independently H, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, aryl, or arylalkyl.

Claim 20

The process of claim 13 wherein said crosslinker is dimethylol paracresol or methyl methoxy diphenyl ether.

Claim 21

The process of claim 13 wherein said crosslinker compound is one or more compounds selected form the group consisting of benzene, 1-methoxy-2,6-bis(hydroxymethyl-4-methyl-; phenol, 2,6-bis(methoxymethyl)-4-methyl-; and benzene, 1-methoxy-2,6-bis(methoxymethyl)-4-methyl-.

Claim 22

The process of claim 13 wherein said solvent comprises propylene glycol alkyl ether acetate.

Claim 23

The process of claim 13 wherein said substrate is selected from the group consisting of silicon, aluminum or polymeric resins, silicon dioxide, doped silicon dioxide, silicon nitride, tantalum, copper, polysilicon, ceramics and aluminum/copper mixtures.

Claim 24

The process of claim 13 wherein said composition further comprises one or more compounds selected form the group consisting of colorants, dyes, anti-striation agents, leveling agents, plasticizers, adhesion promoters, speed enhancers, and surfactants.

Claim 25

The process of claim 13 wherein said developer is an aqueous alkaline solution.

Claim 26

The process of claim 13 wherein after step (e) said coated substrate is overall exposed to actinic radiation of from about 200 to about 500 nm.