US3947425A
Expired / Lapsed
US
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Rapid curing, hydrophilic resin compositions
Assignee: Weyerhaeuser Co
•
Filing: 1973-09-13
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Granted: 1976-03-30
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Expires: 1993-09-13
Abstract
Abstract Described herein are hydrophilic resin products having particular utility in rapid curing adhesives for wood and other materials. Processes for producing these resins and hydrophilic adhesives produced therefrom are also described. The resins are prepared by reacting an aldehyde condensation polymer, such as a phenol-formaldehyde condensation polymer, with a strong mineral acid salt, i.e., a hydrochloric, nitric, or sulfuric acid salt, of m-hydroxy aniline, 2,6-diaminopyridine or 4,4'-diaminodiphenylmethane. When these resins are blended with an appropriate curing agent, such as an aldehyde, the resulting adhesives cure very rapidly at ambient temperatures. While uncured, these adhesives are hydrophilic and thus water washable, but when cured, they are insoluble in water and common organic solvents.
Inventors
- 👤 Harlan G. Freeman
- 👤 Maurice F. Gillern
- 👤 Harry A. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 16:28
CPC Classifications
C; C09; C09J; C09J161/00; C09J161/34; C08; C08G; C08G14/00; C08G14/02; C08G14/04; C08G14/06; C08G8/00; C08G8/04; C08G8/08; C08G8/16; C08G8/26; C08L; C08L61/00; C08L61/02; C09J161/04; C09J161/06; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31942; Y10T428/31949; Y10T428/31957; Y10T428/3196
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
102 words
A hydrophilic resin composition comprising the reaction product of (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound:aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free aldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selection from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.05 to 2.0 parts by weight per part of said resin.
Claim 2
Dependent Claim
102 words
A hydrophilic resin composition comprising the reaction product of (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound:aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free aldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selection from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.05 to 2.0 parts by weight per part of said resin.
Claim 3
Dependent Claim
22 words
The composition of claim 1 wherein the aldehyde is formaldehyde and the ketone is acetone, methyl ethyl ketone or methyl isobutyl ketone.
Claim 4
Dependent Claim
12 words
The composition of claim 2 wherein the polyhydroxy aromatic compound is resorcinol.
Claim 5
Dependent Claim
15 words
The composition of claim 1 wherein the aldehyde is formaldehyde and the ketone is acetone.
Claim 6
Dependent Claim
12 words
The composition of claim 4 wherein the polyhydroxy aromatic compound is resorcinol.
Claim 7
Dependent Claim
25 words
The composition of claim 5 wherein the acetone: formaldehyde mole ratio is from 2.5:1 to 4.5:1 and the resorcinol:formaldehyde ratio is from 0.3:1 to 2:1.
Claim 8
Dependent Claim
32 words
The composition of claim 6 wherein the amine salt is m-hydroxy aniline hydrochloride and the amount thereof is from 0.1 to 1.0 part by weight per part by weight of said resin.
Claim 9
Dependent Claim
25 words
The composition of claim 5 wherein the acetone:formaldehyde mole ratio is from 3:1 to 4:1 and the resorcinol:formaldehyde mole ratio is from 0.75:1 to 1.25:1.
Claim 10
Dependent Claim
28 words
The composition of claim 8 wherein the amine salt is m-hydroxy aniline hydrochloride and the amount thereof is from 0.1 to 1.0 part by weight of said resin.
Claim 11
Dependent Claim
12 words
The composition of claim 1 wherein the salt is m-hydroxy aniline hydrochloride.
Claim 12
Dependent Claim
27 words
The composition of claim 1 wherein the amount of the amine salt is from 0.1 to 1.0 part by weight per part by weight of said resin.
Claim 13
Dependent Claim
12 words
The composition of claim 11 wherein the salt is m-hydroxy aniline hydrochloride.
Claim 14
Dependent Claim
140 words
A rapid curing, hydrophilic adhesive composition comprising: 1. a hydrophilic resin composition comprising the reaction product of (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound-aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free aldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selected from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.5 to 2.0 parts by weight per part of said resin; and 2. a curing agent reactable with said reaction product at ambient temperature, the amount of said curing agent being sufficient to cause said composition to become insoluble and infusible.
Claim 15
Dependent Claim
140 words
A rapid curing, hydrophilic adhesive composition comprising: 1. a hydrophilic resin composition comprising the reaction product of (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound-aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free aldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selected from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.5 to 2.0 parts by weight per part of said resin; and 2. a curing agent reactable with said reaction product at ambient temperature, the amount of said curing agent being sufficient to cause said composition to become insoluble and infusible.
Claim 16
Dependent Claim
13 words
The composition of claim 13 wherein the curing agent comprises an alkylene-donating compound.
Claim 17
Dependent Claim
15 words
The composition of claim 13 wherein the curing agent comprises formaldehyde or a formaldehyde-donating compound.
Claim 18
Dependent Claim
22 words
The composition of claim 13 wherein the aldehyde is formaldehyde and the ketone is acetone, methyl ethyl ketone or methyl isobutyl ketone.
Claim 19
Dependent Claim
12 words
The composition of claim 16 wherein the polyhydroxy aromatic compound is resorcinol.
Claim 20
Dependent Claim
32 words
The composition of claim 17 wherein the amine salt is m-hydroxy aniline hydrochloride and the amount thereof is from 0.1 to 1.0 part by weight per part by weight of said resin.
Claim 21
Dependent Claim
27 words
The composition of claim 13 wherein the ketone:aldehyde mole ratio is from 2.5:1 to 4.5:1 and the polyhydroxy aromatic compound:aldehyde mole ratio is from 0.2:1 to 5:1.
Claim 22
Dependent Claim
27 words
The composition of claim 13 wherein the ketone:aldehyde mole ratio is from 3:1 to 4:1 and the polyhydroxy aromatic compound:aldehyde mole ratio is from 0.75:1 to 1.25:1.
Claim 23
Dependent Claim
27 words
The composition of claim 1 wherein the amount of the amine salt is from 0.1 to 1.0 part by weight per part by weight of said resin.
Claim 24
Dependent Claim
21 words
The composition of claim 21 wherein the aldehyde is formaldehyde, the ketone is acetone, and the polyhydroxy aromatic compound is resorcinol.
Claim 25
Dependent Claim
25 words
The composition of claim 22 wherein the acetone:formaldehyde mole ratio is from 2.5:1 to 4.5:1 and the resorcinol:formaldehyde mole ratio is from 0.3:1 to 2:1.
Claim 26
Dependent Claim
25 words
The composition of claim 22 wherein the acetone:formaldehyde mole ratio is from 3:1 to 4:1 and the resorcinol:formaldehyde mole ratio is from 0.75:1 to 1.25:1.
Claim 27
Dependent Claim
12 words
The composition of claim 28 wherein the salt is m-hydroxy aniline hydrochloride.
Claim 28
Dependent Claim
103 words
A process for producing a hydrophilic resin composition comprising reacting (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound:aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free formaldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selected from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.1 to 1.0 parts by weight per part of said resin.
Claim 29
Dependent Claim
103 words
A process for producing a hydrophilic resin composition comprising reacting (a) a resin produced by reacting a ketone-aldehyde prepolymer with a polyhydroxy aromatic compound, the aldehyde:ketone mole ratio in said resin being from 1.5:1 to 6:1 and the polyhydroxy aromatic compound:aldehyde mole ratio in said resin being from 0.2:1 to 5:1, said resin containing substantially no free formaldehyde and being free of dominant amide-forming substituents; with (b) an amine salt selected from the hydrochloric, nitric and sulfuric acid salts of m-hydroxy aniline and 2,6-diaminopyridine, the amount of the amine salt being from 0.1 to 1.0 parts by weight per part of said resin.
Claim 30
Dependent Claim
22 words
The process of claim 26 wherein the aldehyde is formaldehyde and the ketone is acetone, methy ethyl ketone or methyl isobutyl ketone.
Claim 31
Dependent Claim
27 words
The process of claim 27 wherein the ketone:formaldehyde mole ratio is from 2.5:1 to 4.5:1 and the polyhydroxy aromatic compound:formaldehyde mole ratio is from 0.3:1 to 2:1.
Claim 32
Dependent Claim
12 words
The process of claim 28 wherein the polyhydroxy aromatic compound is resorcinol.
Claim 33
Dependent Claim
27 words
The process of claim 27 wherein the ketone:aldehyde mole ratio is from 3:1 to 4:1 and the polyhydroxy aromatic compound:aldehyde mole ratio is from 0.75:1 to 1.25:1.
Claim 34
Dependent Claim
12 words
The process of claim 30 wherein the polyhydroxy aromatic compound is resorcinol.
References Cited (Backward Citations)
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US3518159A
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US3784515A
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US3471443A
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US3704269A
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US3714121A
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US3784514A
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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) | 1979-03-30 | 1979-09-29 | 1980-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-30 | 1983-09-29 | 1984-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-30 | 1987-09-29 | 1988-03-30 | $7700.00 | Window Closed / Lapsed |