US 4,032,344 AGranted

Polysulfonamide vesicular binders and processes of forming vesicular images

AssigneeEastman Kodak Company

InventorsGeorge L. Fletcher, Jr., Stewart H. Merrill, Carl Kotlarchik, Jr.

Life of this patent

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Abstract

A light-sensitive vesicular imaging composition comprising a vesiculating agent which liberates gas upon exposure to activating radiation, and a binder which is a sulfonamide polymer having the sulfur-nitrogen linkage either in the polymer chain or as a pendant moiety. The composition is coated as a thin film. Imagewise irradiation of the element causes gas bubbles to be released in the exposed areas, which bubbles may be developed by overall heating to a visible record.

Claims19

Dependent claims

In an imaging element comprising:

(I) a support, and on the support an admixture of (II) a waterinsoluble, thermoplastic, polymeric binder having a permeability constant for gas ranging from about 1.times. 10.sup..sup.-11 to about 1.times. 10.sup..sup.-15, and (III) a radiation-decomposable vesiculating agent capable of generating a gas upon imagewise exposure;
the improvement wherein the binder is a sulfonamide polymer having in the backbone or pendant therefrom, the moiety --SO.sub.2 --N<, said polymer having a .lambda. max no greater than about 350 nm in the spectral range of 200 to 750 nm, and at least one repeating unit selected from the group consisting of:
##STR50## wherein:
(A) R.sup.1 is a member selected from the group consisting of:
(1) a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring;
(2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms;
(3) an oxycarbonylphenylene radical;
and
(4) an imino radical;
(B) R.sup.2 is a saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms;
(C) R.sup.3 is a member selected from the group consisting of:
(1) an alkyleneoxycarbonylphenylene radical wherein the number of carbon atoms in the alkylene function is from 1 to 5;
(2) a carbonylimino radical;
(3) in formula (a) only, a nitrogen-carbon bond when R.sup.1 is other than an oxycarbonylphenylene or an imino radical;
and
(4) an .alpha.-iminocarbonyl -carbonylalkylene radical when R.sup.1 is an imino radical and R.sup.1 and R.sup.3 are each connected to a nitrogen atom;
(D) Z.sup.1 and Z.sup.2 are the same or different, and are each the atoms necessary to complete a heterocyclic group;
(E) R.sup.6 and R.sup.7 are the same or different and can be a hydrogen atom or a methyl radical joined to one of the carbon atoms of Z.sup.1 or Z.sup.2 ;
(f) r.sup.4 is an alkylene radical containing from 1 to 5 carbon atoms or an isophthalate or terephthalate radical;
(G) R.sup.5 is methyl or a hydrogen atom;
(H) L is a member selected from the group consisting of a carbon-nitrogen bond, a phenyl linked in the ortho or para positions, and carbonyl;
(I) M is a member selected from the group consisting of --NH.sub.2, an alkyl radical containing from 1 to 10 carbon atoms, and a methyl-substituted or unsubstituted aryl radical containing from 6 to 10 carbon atoms;
(J) Q is an alkylene radical containing from 2 to 5 carbon atoms when R.sup.4 is isophthalate or terephthalate and otherwise is a chemical bond;
and
(K) T is either (1) a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring, (2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms, or (3) a nitrogen-to-sulfur bond when M is other than --NH.sub.2 ;
(l) the substituents of said substituted aromatic ring of (A) (1), (B), and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms;
(2) a halogen atom;
(3) a phenyl radical;
(4) an acyl radical or an alkoxy radical the alkyl portion of which has from 1 to 4 carbon atoms;
and
(5) an alkylthio radical;
and
(M) the substituents of said substituted alkylene radical of (A) (2) and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms, and
(2) a phenyl radical.

33 more elements

In an imaging element comprising:

(I) a support, and on the support, an admixture of (II) a water-insoluble thermoplastic, polymeric binder having a permeability constant for gas ranging from about 1.times. 10.sup..sup.-11 to about 1.times. 10.sup..sup.-15, and (III) a radiation-decomposable vesiculating agent capable of generating a gas upon imagewise exposure;
the improvement wherein the binder is a polymer having a repeating unit ##STR52## wherein (A) R.sup.1 is a member selected from the group consisting of:
(1) a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring;
(2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms;
(3) an oxycarbonylphenylene radical;
and
(4) an imino radical;
(B) R.sup.2 is a saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms;
and
(C) R.sup.3 is a member selected from the group consisting of:
(1) an alkyleneoxycarbonylphenylene radical wherein the number of carbon atoms in the alkylene function is from 1 to 5;
(2) a carbonylimino radical;
(3) a nitrogen-carbon bond when R.sup.1 is other than an oxycarbonylphenylene or an imino radical;
and
(4) an .alpha.-iminocarbonyl-.omega.-carbonylalkylene radical when R.sup.1 is an imino radical and R.sup.1 and R.sup.3 are each connected to a nitrogen atom;
(D) the substituents of said substituted aromatic ring of (A) (and (B) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms;
(2) a halogen atom;
(3) a phenyl radical;
(4) an acyl radical or an alkoxy radical the alkyl portion of which has from 1 to 4 carbon atoms;
and
(5) an alkylthio radical;
and
(E) the substituents of said substituted alkylene radical of (A) (2) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms, and
(2) a phenyl radical.

23 more elements

A dry process for forming a photographic image, comprising the steps of:

(a) imagewise-exposing a radiation-sensitive photographic element containing, on a support, an admixture of a decomposable radiation-sensitive vesiculating agent capable of generating a gas upon exposure to activating radiation, and a polymeric binder having as a repeating unit one which includes the linkage >N--SO.sub.2 -- as a portion of the backbone of the polymer or as a pendant moiety and is selected from the group consisting of ##STR53## wherein (A) R.sup.1 is a member selected from the group consisting of:
(1) a substituted or unsubstituted saturated carbocylic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring;
(2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms;
(3) an oxycarbonylphenylene radical;
and
(4) an imino radical;
(B) R.sup.2 is a saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms;
(C) R.sup.3 is a member selected from the group consisting of:
(1) an alkyleneoxycarbonylphenylene radical wherein the number of carbon atoms in the alkylene function is from 1 to 5;
(2) a carbonylimino radical;
(3) in formula (a) only, a nitrogen-carbon bond when R.sup.1 is other than an oxycarbonylphenylene or an imino radical;
and
(4) an .alpha.-iminocarbonyl-.omega.-carbonylalkylene radical when R.sup.1 is an imino radical and R.sup.1 and R.sup.3 are each connected to a nitrogen atom;
(D) Z.sup.1 and Z.sup.2 are the same or different, and are each the atoms necessary to complete a heterocyclic group;
(E) R.sup.6 and R.sup.7 are the same or different and can be a hydrogen atom or a methyl radical joined to one of the carbon atoms of Z.sup.1 or Z.sup.2 ;
(f) r.sup.4 is an alkylene radical containing from 1 to 5 carbon atoms or an isophthalate or terephthalate radical;
(G) R.sup.5 is methyl or a hydrogen atom;
(H) L is a member selected from the group consisting of a carbon-nitrogen bond, a phenyl linked to the unit in the ortho positions, and carbonyl;
(I) M is a member selected from the group consisting of --NH.sub.2, an alkyl radical containing from 1 to 10 carbon atoms, and a methyl-substituted or unsubstituted aryl radical containing from 6 to 10 carbon atoms;
(J) Q is an alkylene radical containing from 2 to 5 carbon atoms when R.sup.4 is isophthalate or terephthalate and otherwise is a chemical bond;
and
(K) T is a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6-10 carbon atoms in the ring;
a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms, or a nitrogen-to-sulfur bond when M is other than --NH.sub.2 ;
(l) the substituents of said substituted aromatic ring of (A) (1), (B), and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms;
(2) a halogen atom;
(3) a phenyl radical;
(4) an acyl radical or an alkoxy radical the alkyl portion of which has from 1 to 4 carbon atoms;
and
(5) an alkylthio radical;
and
(M) the substituents of said alkylene radical of (A) (2) and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms;
and
(2) a phenyl radical;
and
(b) developing the exposed element by heating it to a temperature and for a time sufficient to force the gas bubbles formed by the photodecomposition of the agent to expand to form a visible image.

34 more elements

Dependencies are inferred from the claim text.

Facts

Application: 05/645,178Filed 29 Dec 1975 · continuation in part
Priority: 16 Jan 1975
Granted: 28 Jun 1977
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

G03C 5/60
Photographic processes or agents therefor; Regeneration of such processing agents: processes for obtaining vesicular images
C08G 63/6886
Derived from polycarboxylic acids and polyhydroxy compounds: dicarboxylic acids and dihydroxy compounds
C08L 33/26
Homopolymers or copolymers of amides or imides: homopolymers or copolymers of acrylamide or methacrylamide
C08L 41/00
Compositions of homopolymers or copolymers of compounds having one or more unsaturated

Family

Serial541,676Parent of this continuation-in-part · filed 16 Jan 1975
US 4,032,344 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

In an imaging element comprising:

(I) a support, and on the support an admixture of (II) a waterinsoluble, thermoplastic, polymeric binder having a permeability constant for gas ranging from about 1.times. 10.sup..sup.-11 to about 1.times. 10.sup..sup.-15, and (III) a radiation-decomposable vesiculating agent capable of generating a gas upon imagewise exposure;
the improvement wherein the binder is a sulfonamide polymer having in the backbone or pendant therefrom, the moiety --SO.sub.2 --N<, said polymer having a .lambda. max no greater than about 350 nm in the spectral range of 200 to 750 nm, and at least one repeating unit selected from the group consisting of:
##STR50## wherein:
(A) R.sup.1 is a member selected from the group consisting of:
(1) a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring;
(2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms;
(3) an oxycarbonylphenylene radical;
and
(4) an imino radical;
(B) R.sup.2 is a saturated carbocyclic ring containing from 5 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms;
(C) R.sup.3 is a member selected from the group consisting of:
(1) an alkyleneoxycarbonylphenylene radical wherein the number of carbon atoms in the alkylene function is from 1 to 5;
(2) a carbonylimino radical;
(3) in formula (a) only, a nitrogen-carbon bond when R.sup.1 is other than an oxycarbonylphenylene or an imino radical;
and
(4) an .alpha.-iminocarbonyl -carbonylalkylene radical when R.sup.1 is an imino radical and R.sup.1 and R.sup.3 are each connected to a nitrogen atom;
(D) Z.sup.1 and Z.sup.2 are the same or different, and are each the atoms necessary to complete a heterocyclic group;
(E) R.sup.6 and R.sup.7 are the same or different and can be a hydrogen atom or a methyl radical joined to one of the carbon atoms of Z.sup.1 or Z.sup.2 ;
(f) r.sup.4 is an alkylene radical containing from 1 to 5 carbon atoms or an isophthalate or terephthalate radical;
(G) R.sup.5 is methyl or a hydrogen atom;
(H) L is a member selected from the group consisting of a carbon-nitrogen bond, a phenyl linked in the ortho or para positions, and carbonyl;
(I) M is a member selected from the group consisting of --NH.sub.2, an alkyl radical containing from 1 to 10 carbon atoms, and a methyl-substituted or unsubstituted aryl radical containing from 6 to 10 carbon atoms;
(J) Q is an alkylene radical containing from 2 to 5 carbon atoms when R.sup.4 is isophthalate or terephthalate and otherwise is a chemical bond;
and
(K) T is either (1) a substituted or unsubstituted saturated carbocyclic ring containing from 5 to 10 carbon atoms, or substituted or unsubstituted aromatic ring containing from 6 to 10 carbon atoms in the ring, (2) a substituted or unsubstituted alkylene radical containing from 1 to 10 carbon atoms, or (3) a nitrogen-to-sulfur bond when M is other than --NH.sub.2 ;
(l) the substituents of said substituted aromatic ring of (A) (1), (B), and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms;
(2) a halogen atom;
(3) a phenyl radical;
(4) an acyl radical or an alkoxy radical the alkyl portion of which has from 1 to 4 carbon atoms;
and
(5) an alkylthio radical;
and
(M) the substituents of said substituted alkylene radical of (A) (2) and (K) being selected from the group consisting of:
(1) an alkyl radical containing from 1 to 4 carbon atoms, and
(2) a phenyl radical.

33 more elements

Facts

Application

05/645,178Filed 29 Dec 1975 · continuation in part

Priority

16 Jan 1975

Granted

28 Jun 1977

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

G03C 5/60
Photographic processes or agents therefor; Regeneration of such processing agents: processes for obtaining vesicular images
C08G 63/6886
Derived from polycarboxylic acids and polyhydroxy compounds: dicarboxylic acids and dihydroxy compounds
C08L 33/26
Homopolymers or copolymers of amides or imides: homopolymers or copolymers of acrylamide or methacrylamide
C08L 41/00
Compositions of homopolymers or copolymers of compounds having one or more unsaturated