Patent US4038226A successfully refreshed from Google Patents.
US4038226A
Expired / Lapsed
US
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Method and composition for solventless printing
Assignee: Chemetron Corp
•
Filing: 1975-05-22
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Granted: 1977-07-26
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Expires: 1995-05-22
Abstract
Abstract Sulfonylarylhydrazides are used as latent catalysts for condensation reactions, particularly in the curing of solventless heat-setting printing ink compositions.
Inventors
- 👤 Jack Lewis Towle
- 👤 John Herman Vander Ploeg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:47
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/02; C09D11/10; C09D11/102; C08; C08K; C08K5/00; C08K5/36; C08K5/43; Y; Y10; Y10S; Y10S260/00; Y10S260/38
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
61 words
A method of polymerizing an amino resin precursor which comprises heating the precursor in the presence of a catalytic amount of at least one latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolylhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide to a curing temperature of from about the in situ decomposition temperature of the latent catalyst to about the decomposition temperature of the precursor.
Claim 2
Independent Claim
61 words
A method of polymerizing an amino resin precursor which comprises heating the precursor in the presence of a catalytic amount of at least one latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolylhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide to a curing temperature of from about the in situ decomposition temperature of the latent catalyst to about the decomposition temperature of the precursor.
Claim 3
Dependent Claim
18 words
The method of claim 1 wherein the curing temperature is from about 140° C. to about 260° C.
Claim 4
Dependent Claim
18 words
The method of claim 1 wherein the curing temperature is from about 170° C. to about 200° C.
Claim 5
Dependent Claim
11 words
The method of claim 1 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 6
Dependent Claim
23 words
The method of claim 1 wherein the latent catalyst is present at a concentration of from about 0.1% to about 10% by weight.
Claim 7
Dependent Claim
29 words
The method of claim 1 wherein the amino resin precursor is a formaldehyde condensate of a urea, a melamine, or a guanamine, or a lower-alkyl ether of said condensate.
Claim 8
Dependent Claim
81 words
The method of claim 6 wherein the amino resin precursor is a compound of the general formula ##STR2## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and a radical represented by the formula --CH 2 --O--(CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 9
Dependent Claim
14 words
The method of claim 7 wherein each X is --CH 2 --O--CH 3 :
Claim 10
Dependent Claim
11 words
The method of claim 8 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 11
Dependent Claim
43 words
The method of claim 1 wherein the amino resin precursor is a mixture of a co-condensate resin containing a carboxyl, hydroxyl or amide functionality and a formaldehyde condensate of a urea, a melamine or a guanamine, or a lower-alkyl ether of said condensate.
Claim 12
Dependent Claim
15 words
The method of claim 10 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 13
Dependent Claim
87 words
The method of claim 10 wherein the amino resin precursor is a mixture of the co-condensate and a compond of the general formula ##STR3## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and a radical represented by the formula --CH 2 --O--(CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 14
Dependent Claim
13 words
The method of claim 12 wherein X is --CH 2 --O--CH 3 .
Claim 15
Dependent Claim
15 words
The method of claim 13 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 16
Dependent Claim
11 words
The method of claim 14 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 17
Dependent Claim
45 words
The method of claim 1 wherein the amino resin precursor is a partially cross-linked copolymer of a co-condensate resin containing a carboxyl, hydroxyl or amide functionality and a formaldehyde condensate of a urea, a melamine, or a guanamine, or a lower-alkyl ether of said condensate.
Claim 18
Dependent Claim
90 words
The method of claim 16 wherein the amino resin precursor is a partially cross-linked copolymer of the co-condensate resin and a compound of the general formula ##STR4## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and radical represented by the formula --CH 2 --O-- (CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 19
Dependent Claim
14 words
The method of claim 17 wherein each X is --CH 2 --O--CH 3 .
Claim 20
Dependent Claim
15 words
The method of claim 18 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 21
Dependent Claim
11 words
The method of claim 19 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 22
Independent Claim
82 words
A method for solventless printing which comprises reacting a drying oil-modified alkyd resin and hexamethoxymethylmelamine to form a partially cross-linked copolymer; mixing the copoylmer with a pigment and a catalytic amount of at least one latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolylhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide; depositing the mixture on a substrate; and subjecting the mixture to a curing temperature of from about the in situ decomposition temperature of the latent catalyst to about the decomposition temperature of the mixture.
Claim 23
Independent Claim
82 words
A method for solventless printing which comprises reacting a drying oil-modified alkyd resin and hexamethoxymethylmelamine to form a partially cross-linked copolymer; mixing the copoylmer with a pigment and a catalytic amount of at least one latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolylhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide; depositing the mixture on a substrate; and subjecting the mixture to a curing temperature of from about the in situ decomposition temperature of the latent catalyst to about the decomposition temperature of the mixture.
Claim 24
Dependent Claim
26 words
The method of claim 21 wherein the drying oil-modified alkyd resin contains an acrylate or methacrylate ester moiety and has a residual hydroxyl or amide group.
Claim 25
Dependent Claim
33 words
A resin precursor composition comprising an amino resin precursor and from about 0.1 to about 10% by weight of a latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolyhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide.
Claim 26
Dependent Claim
33 words
A resin precursor composition comprising an amino resin precursor and from about 0.1 to about 10% by weight of a latent catalyst selected from the group consisting of ortho-toluenesulfonyl-ortho-tolyhydrazide, benzylsulfonylphenylhydrazide, benzenesulfonylphenylhydrazide, and para-toluenesulfonylphenylhydrazide.
Claim 27
Dependent Claim
11 words
The composition of claim 23 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 28
Dependent Claim
9 words
The composition of claim 23 further comprising a pigment.
Claim 29
Dependent Claim
29 words
The composition of claim 23 wherein the amino resin precursor is a formaldehyde condensate of a urea, a melamine, or a guanamine, or a lower-alkyl ether of said condensate.
Claim 30
Dependent Claim
81 words
The composition of claim 23 wherein the amino resin precursor is a compound of the general formula ##STR5## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and a radical represented by the formula --CH 2 --O--(CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 31
Dependent Claim
14 words
The composition of claim 27 wherein each X is --CH 2 --O--CH 3 .
Claim 32
Dependent Claim
43 words
The composition of claim 23 wherein the amino resin precursor is a mixture of a co-condensate resin containing a carboxyl, hydroxyl or amide functionality and a formaldehyde condensate of a urea, a melamine or a guanamine or a lower-alkyl ether of said condensate.
Claim 33
Dependent Claim
15 words
The composition of claim 29 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 34
Dependent Claim
87 words
The composition of claim 29 wherein the amino resin precursor is a mixture of the co-condensate resin and compound of the general formula ##STR6## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and a radical represented by the formula --CH 2 --O--(CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 35
Dependent Claim
14 words
The composition of claim 31 wherein each X is --CH 2 --O--CH 3 .
Claim 36
Dependent Claim
15 words
The composition of claim 32 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 37
Dependent Claim
11 words
The composition of claim 33 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 38
Dependent Claim
9 words
The composition of claim 34 further comprising a pigment.
Claim 39
Dependent Claim
45 words
The composition of claim 23 wherein the amino resin precursor is a partially cross-linked copolymer of a co-condensate resin containing a carboxyl, hydroxyl or amide functionality and a formaldehye condensate of a urea, a melamine, or a guanamine, or a lower-alkyl ether of said condensate.
Claim 40
Dependent Claim
89 words
The composition of claim 36 wherein the amino resin precursor is a partially cross-linked copolymer of the co-codensate resin and a compound of the general formula ##STR7## wherein X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are the same as or different from one another and are selected from the group consisting of hydrogen and radical represented by the formula --CH 2 --O--(CH 2 ) n CH 3 , in which n is an integer from 0 to 3.
Claim 41
Dependent Claim
14 words
The composition of claim 37 wherein each X is --CH 2 --O--CH 3 .
Claim 42
Dependent Claim
15 words
The composition of claim 38 wherein the co-condensate resin is a drying oil-modified alkyd resin.
Claim 43
Dependent Claim
11 words
The composition of claim 39 wherein the latent catalyst is para-toluenesulfonylphenylhydrazide.
Claim 44
Dependent Claim
9 words
The composition of claim 40 further comprising a pigment.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |