US4291153A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Water-dispersible polyester adhesives for photographic materials
Assignee: Eastman Kodak Co
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Filing: 1980-08-01
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Granted: 1981-09-22
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Expires: 2000-08-01
Abstract
Abstract Disclosed herein are heat-activatable adhesive compositions containing a water-dispersible polyester which comprises A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from at least one dicarboxylic acid having an ionic iminosulfonyl moiety containing a monovalent cation as an imino nitrogen substituent; (2) from about 40 to about 70 mole percent of units derived from at least one dicarboxylic acid selected from the group consisting of aliphatic dicarboxylic acids having the formula HOOC--(CH 2 ) n --COOH wherein n is an integer from 2 to 12, cycloaliphatic dicarboxylic acids having from 6 to 12 carbon atoms, and aromatic dicarboxylic acids having from 6 to 12 carbon atoms; (3) from about 5 to about 20 mole percent of units derived from the dicarboxylic acid having the formula ##STR1## (4) from about 5 to about 25 mole percent of units derived from at least one dicarboxylic acid having the formula ##STR2## wherein Z is carbonylimino or iminocarbonyl and m is an integer from 6 to 10; and B. a diol component consisting essentially of (1) at least 50 mole percent of units derived from at least one diol having a formula selected from the group consisting of: ##STR3## wherein p is an integer from 1 to 4, and HO--(RO).sub.q --H (II) wherein q is an integer from 2 to 4; and R is an alkylene group having from 2 to 4 carbon atoms; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula: HO--R'--OH wherein R' is an alkylene group having up to 16 carbon atoms, cycloalkylene having from 6 to 20 carbon atoms, cycloalkylenebisalkylene having from 8 to 20 carbon atoms, or arylenebisalkylene having from 8 to 20 carbon atoms with the proviso that said diol component (1), selected from the group consisting of (I) and (II), must comprise at least 90 mole percent of the diol component when said acid component (1), having an ionic iminosulfonyl moiety, comprises less than 10 mole percent of said acid component. These adhesives have been found useful in a variety of photographic materials, and particularly in image transfer film units. Their adhesive strength is further characterized as being insensitive to variations in relative humidity and, after being dried, to the presence of aqueous processing compositions.
Inventors
- 👤 John M. Noonan
- 👤 Robert C. McConkey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 05:06
CPC Classifications
C; C09; C09J; C09J167/00; C09J167/06; C08; C08G; C08G63/00; C08G63/66; C08G63/668; C08G63/676; G; G03; G03C; G03C8/00; G03C8/42; G03C8/52
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
344 words
An adhesive composition comprising a water-dispersible polyester which comprises A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from at least one dicarboxylic acid having an ionic iminosulfonyl moiety containing a monovalent cation as an imino nitrogen substituent; (2) from about 40 to about 70 mole percent of units derived from at least one dicarboxylic acid selected from the group consisting of aliphatic dicarboxylic acids having the formula HOOC--(CH 2 ) n --COOH wherein n is an integer from 2 to 12, cycloaliphatic dicarboxylic acids having from 6 to 22 carbon atoms and aromatic dicarboxylic acids having from 6 to 12 carbon atoms; (3) from about 5 to about 20 mole percent of units derived from a dicarboxylic acid having the formula: ##STR28## (4) from about 5 to about 25 mole percent of units derived from at least one dicarboxylic acid having the formula: ##STR29## wherein Z is selected from the group consisting of carbonylimino and iminocarbonyl and m is an integer from 6 to 10; and B. a diol component consisting essentially of: (1) at least 50 mole percent of units derived from at least one diol having a formula selected from the group consisting of: ##STR30## wherein p is an integer from 1 to 4, and HO--(RO).sub.q --H (II) wherein q is an integer from 2 to 4 and R is alkylene having from 2 to 4 carbon atoms; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is an alkylene group having up to 16 carbon atoms, cycloalkylene having from 6 to 20 carbon atoms, cycloalkylenebisalkylene having from 8 to 20 carbon atoms, or arylenebisalkylene having from 8 to 20 carbon atoms, with the proviso that said diol component (1), selected from the group consisting of (I) and (II), must comprise at least 90 mole percent of the diol component when said acid component (1), having an ionic iminosulfonyl moiety, comprises less than 10 mole percent of said acid component.
Claim 2
Dependent Claim
344 words
An adhesive composition comprising a water-dispersible polyester which comprises A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from at least one dicarboxylic acid having an ionic iminosulfonyl moiety containing a monovalent cation as an imino nitrogen substituent; (2) from about 40 to about 70 mole percent of units derived from at least one dicarboxylic acid selected from the group consisting of aliphatic dicarboxylic acids having the formula HOOC--(CH 2 ) n --COOH wherein n is an integer from 2 to 12, cycloaliphatic dicarboxylic acids having from 6 to 22 carbon atoms and aromatic dicarboxylic acids having from 6 to 12 carbon atoms; (3) from about 5 to about 20 mole percent of units derived from a dicarboxylic acid having the formula: ##STR28## (4) from about 5 to about 25 mole percent of units derived from at least one dicarboxylic acid having the formula: ##STR29## wherein Z is selected from the group consisting of carbonylimino and iminocarbonyl and m is an integer from 6 to 10; and B. a diol component consisting essentially of: (1) at least 50 mole percent of units derived from at least one diol having a formula selected from the group consisting of: ##STR30## wherein p is an integer from 1 to 4, and HO--(RO).sub.q --H (II) wherein q is an integer from 2 to 4 and R is alkylene having from 2 to 4 carbon atoms; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is an alkylene group having up to 16 carbon atoms, cycloalkylene having from 6 to 20 carbon atoms, cycloalkylenebisalkylene having from 8 to 20 carbon atoms, or arylenebisalkylene having from 8 to 20 carbon atoms, with the proviso that said diol component (1), selected from the group consisting of (I) and (II), must comprise at least 90 mole percent of the diol component when said acid component (1), having an ionic iminosulfonyl moiety, comprises less than 10 mole percent of said acid component.
Claim 3
Dependent Claim
26 words
The adhesive composition of claim 1 wherein the polyester has a glass transition temperature within the range of from about 25° C. to about 50° C.
Claim 4
Dependent Claim
37 words
The adhesive composition of claim 1 wherein the polyester has an inherent viscosity within the range of 0.1 to 1.0 at 25° C. in a 1:1 mixture of phenol and chlorobenzene at a concentration of 0.25 g/dl.
Claim 5
Dependent Claim
62 words
The adhesive composition of claim 1 wherein said acid component (1), having an ionic iminosulfonyl moiety, has the formula: ##STR31## wherein: r and s are integers whose sum equals 1; Q is defined by the formula ##STR32## wherein Y is arylene; Q' is selected from the group consisting of: ##STR33## wherein Y' is alkyl or aryl and M is a solubilizing cation.
Claim 6
Dependent Claim
20 words
The adhesive composition of claim 4 wherein r is 0, s is 1, Y is arylene and M is Na.
Claim 7
Dependent Claim
10 words
The adhesive composition of claim 5 wherein Y is 1,3-phenylene.
Claim 8
Dependent Claim
24 words
The adhesive composition of claim 1 wherein said acid component (2) has the formula HO--(CH.sub.2)n--COOH wherein n is an integer from 2 to 12.
Claim 9
Dependent Claim
10 words
The adhesive composition of claim 7 wherein n is 2.
Claim 10
Dependent Claim
30 words
The adhesive composition of claim 1 wherein said acid component (4) has the formula ##STR34## wherein Z is carbonylimino or iminocarbonyl and m is an integer of 6 to 8.
Claim 11
Dependent Claim
10 words
The adhesive composition of claim 9 wherein m is 8.
Claim 12
Dependent Claim
71 words
The adhesive composition of claim 1 wherein said diol component consists essentially of: (1) at least 50 mole percent of units derived from at least one diol having the formula: ##STR35## wherein p is an integer from 1 to 4; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is cycloalkylenebisalkylene having from 8 to 20 carbon atoms.
Claim 13
Dependent Claim
18 words
The adhesive composition of claim 11 wherein said diol component comprises at least 50 mole percent of 1,4-bis(2-hydroxyethoxy)cyclohexane.
Claim 14
Dependent Claim
294 words
An adhesive composition comprising a water-dispersible polyester having a glass transition temperature within the range of from about 25° C. to about 50° C., the polyester comprising A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from at least one dicarboxylic acid having the formula ##STR36## wherein r and s are integers whose sum equals 1; Q is defined by the formula ##STR37## wherein Y is arylene, Q' is selected from the group consisting of: ##STR38## wherein Y' is alkyl or aryl, and M is a solubilizing cation; (2) from about 40 to about 70 mole percent of units derived from at least one dicarboxylic acid having the formula HOOC--(CH 2 ) n --COOH, wherein n is an integer from 2 to 12; (3) from about 5 to about 20 mole percent of units derived from the dicarboxylic acid having the formula ##STR39## (4) from about 5 to about 25 mole percent of units derived from at least one dicarboxylic acid having the formula ##STR40## wherein Z is selected from the group consisting of carbonylimino and iminocarbonyl and m is an integer from 6 to 10; and B. a diol component consisting essentially of: (1) at least 50 mole percent of units derived from at least one diol having the formula ##STR41## wherein p is an integer from 1 to 4; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is cycloalkylenebisalkylene having from 8 to 20 carbon atoms, with the proviso that said diol component (1) must comprise at least 90 mole percent of the diol component when said acid component (1) comprises less than 10 mole percent of said acid component.
Claim 15
Dependent Claim
294 words
An adhesive composition comprising a water-dispersible polyester having a glass transition temperature within the range of from about 25° C. to about 50° C., the polyester comprising A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from at least one dicarboxylic acid having the formula ##STR36## wherein r and s are integers whose sum equals 1; Q is defined by the formula ##STR37## wherein Y is arylene, Q' is selected from the group consisting of: ##STR38## wherein Y' is alkyl or aryl, and M is a solubilizing cation; (2) from about 40 to about 70 mole percent of units derived from at least one dicarboxylic acid having the formula HOOC--(CH 2 ) n --COOH, wherein n is an integer from 2 to 12; (3) from about 5 to about 20 mole percent of units derived from the dicarboxylic acid having the formula ##STR39## (4) from about 5 to about 25 mole percent of units derived from at least one dicarboxylic acid having the formula ##STR40## wherein Z is selected from the group consisting of carbonylimino and iminocarbonyl and m is an integer from 6 to 10; and B. a diol component consisting essentially of: (1) at least 50 mole percent of units derived from at least one diol having the formula ##STR41## wherein p is an integer from 1 to 4; and (2) from 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is cycloalkylenebisalkylene having from 8 to 20 carbon atoms, with the proviso that said diol component (1) must comprise at least 90 mole percent of the diol component when said acid component (1) comprises less than 10 mole percent of said acid component.
Claim 16
Dependent Claim
37 words
The adhesive composition of claim 13 wherein the polyester has an inherent viscosity within the range of 0.1 to 1.0 at 25° C. in a 1:1 mixture of phenol and chlorobenzene at a concentration of 0.25 g/dl.
Claim 17
Dependent Claim
16 words
The adhesive composition of claim 13 wherein said acid component (1) is derived from 3,3'-sodioiminodisulfonyldibenzoic acid.
Claim 18
Dependent Claim
16 words
The adhesive composition of claim 13 wherein said acid component (2) is derived from succinic acid.
Claim 19
Dependent Claim
15 words
The adhesive composition of claim 13 wherein said component (4) is derived from 1,8-octylenebis-(carbonylimino-4-benzoic acid).
Claim 20
Dependent Claim
58 words
The adhesive composition of claim 13 wherein said diol component consists essentially of: (1) at least 50 mole percent of units derived from at least one diol having the formula ##STR42## wherein p is 1; and (2) 0 to 50 mole percent of units derived from at least one diol having the formula HO--R'--OH wherein R' is ##STR43##
Claim 21
Dependent Claim
37 words
The adhesive composition of claim 13 wherein said diol component consists essentially of 100 mole percent of units derived from at least one diol having the formula: ##STR44## wherein p is an integer from 1 to 4.
Claim 22
Dependent Claim
18 words
The adhesive composition of claim 13 wherein said diol component consists essentially of 100 mole percent of 1,4-bis(2-hydroxyethoxy)cyclohexane.
Claim 23
Dependent Claim
135 words
An adhesive composition comprising a water-dispersible polyester having a glass transition temperature within the range of from about 25° C. to about 50° C. and an inherent viscosity within the range of about 0.1 to 1.0 at 25° C. in a 1:1 mixture of phenol and chlorobenzene at a concentration of 0.25 g/dl, the polyester comprising A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from 3,3'-sodioiminodisulfonyldibenzoic acid; (2) from about 40 to about 70 mole percent of units derived from succinic acid; (3) from about 5 to about 20 mole percent of units derived from 3,3'-(1,4-phenylene)bisacrylic acid; and (4) from about 5 to about 25 mole percent of units derived from 1,8-octylenebis(carbonylimino-4-benzoic acid); and B. a diol component consisting essentially of 100 mole percent of 1,4-bis(2-hydroxyethoxy)cyclohexane.
Claim 24
Dependent Claim
135 words
An adhesive composition comprising a water-dispersible polyester having a glass transition temperature within the range of from about 25° C. to about 50° C. and an inherent viscosity within the range of about 0.1 to 1.0 at 25° C. in a 1:1 mixture of phenol and chlorobenzene at a concentration of 0.25 g/dl, the polyester comprising A. an acid component comprising: (1) from about 8 to about 16 mole percent of units derived from 3,3'-sodioiminodisulfonyldibenzoic acid; (2) from about 40 to about 70 mole percent of units derived from succinic acid; (3) from about 5 to about 20 mole percent of units derived from 3,3'-(1,4-phenylene)bisacrylic acid; and (4) from about 5 to about 25 mole percent of units derived from 1,8-octylenebis(carbonylimino-4-benzoic acid); and B. a diol component consisting essentially of 100 mole percent of 1,4-bis(2-hydroxyethoxy)cyclohexane.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-21 | 1985-03-23 | 1985-09-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-21 | 1989-03-23 | 1989-09-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-21 | 1993-03-23 | 1993-09-22 | $7700.00 | Window Closed / Lapsed |