Patent US4036816A successfully refreshed from Google Patents.
US4036816A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of novel thermosetting phenol-formaldehyde resins by controlled acid reaction
Assignee: Cor Tech Research Ltd
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Filing: 1975-12-01
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Granted: 1977-07-19
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Expires: 1995-12-01
Abstract
Abstract A novel thermosetting phenol-formaldehyde resin having a preponderance of benzyl ether linkages is characterized by its infra-red spectrum which exhibits absorption at wave numbers of about 1010 cm<->1, 1050 cm<->1 and 1230 cm<->1. The infrared spectrum has a particular ratio of absorbance at 1010 cm<->1, measured from a base line drawn between wave members of 1030 cm<->1 and 950 cm<->1, to that at 1230 cm<->1, measured from a base line drawn between wave numbers of 1130 cm<->1 and 1310 cm<->1 which is less than about 0.1. These novel resins are prepared by the controlled addition of strong acids to thermosetting phenol-formaldehyde resins having a preponderance of benzyl ether linkages and an infrared spectrum exhibiting large adsorption at wave numbers of 1230 cm<->1, 1050 cm<->1 and 1010 cm<->1, causing a decrease of at least 35% in the ratio of absorbance at 1010 cm<->1, measured from a base line drawn between wave numbers of 1030 cm<->1 and 950 cm<-> 1 to that at 1230 cm<->1, measured from a base line drawn between wave numbers of 1130 cm<->1 and 1310 cm<->1, while leaving substantially unaltered the absorbance at wave numbers of 1230 cm<->1 and 1050 cm<->1. The novel resin is capable of many applications and is normally tack-free, although the tack may be controlled by the addition of an organic solvent, such as phenol, thereto.
Inventors
- 👤 Ramesh C. Vasishth
- 👤 Pitchaiya Chandramouli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 11:09
CPC Classifications
C; C09; C09J; C09J161/00; C09J161/04; C09J161/06; B; B22; B22C; B22C1/00; B22C1/16; B22C1/20; B22C1/22; B22C1/2233; B22C1/2246; B22C1/2253; C08; C08G; C08G8/00; C08G8/04; C08G8/08; C08G8/10; C08L; C08L97/00; C08L97/02
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
221 words
A method for the production of a thermosetting phenol-formaldehyde resin, which comprises: reacting phenol with formaldehyde in an aqueous reaction medium in the presence of a metal carboxylate catalyst therefor to form a thermosetting phenol-formaldehyde resin having benzyl ether linkages and hemiformal groups ortho to the phenolic hydroxyl groups and an infra-red spectrum which displays large absorption at wave numbers of approximately 1230 cm - 1 , 1050 cm - 1 and 1010 cm - 1 , contacting said resin with at least one strong acid to cause a decrease of at least 35% in the ratio of absorbance at 1010 cm - 1 , measured from a base line drawn between wave numbers of 1030 cm - 1 and 950 cm - 1 , to that at 1230 cm - 1 , measured from a base line drawn between wave numbers of 1130 cm - 1 and 1310 cm - 1 , to a value less than about 0.1, while leaving substantially unaffected the absorption at wave numbers of 1230 cm - 1 and 1050 cm - 1 , and recovering the resulting thermosetting phenol-formaldehyde resin having a preponderance of benzyl ether linkages ortho to the phenolic hydroxyl groups, having substantially no tendency to cure upon extensive standing at ambient temperature and being capable of rapid cure at elevated temperature.
Claim 2
Independent Claim
221 words
A method for the production of a thermosetting phenol-formaldehyde resin, which comprises: reacting phenol with formaldehyde in an aqueous reaction medium in the presence of a metal carboxylate catalyst therefor to form a thermosetting phenol-formaldehyde resin having benzyl ether linkages and hemiformal groups ortho to the phenolic hydroxyl groups and an infra-red spectrum which displays large absorption at wave numbers of approximately 1230 cm - 1 , 1050 cm - 1 and 1010 cm - 1 , contacting said resin with at least one strong acid to cause a decrease of at least 35% in the ratio of absorbance at 1010 cm - 1 , measured from a base line drawn between wave numbers of 1030 cm - 1 and 950 cm - 1 , to that at 1230 cm - 1 , measured from a base line drawn between wave numbers of 1130 cm - 1 and 1310 cm - 1 , to a value less than about 0.1, while leaving substantially unaffected the absorption at wave numbers of 1230 cm - 1 and 1050 cm - 1 , and recovering the resulting thermosetting phenol-formaldehyde resin having a preponderance of benzyl ether linkages ortho to the phenolic hydroxyl groups, having substantially no tendency to cure upon extensive standing at ambient temperature and being capable of rapid cure at elevated temperature.
Claim 3
Dependent Claim
14 words
The method of claim 1 wherein said strong acid is an aryl sulfonic acid.
Claim 4
Dependent Claim
32 words
The method of claim 2 wherein said strong acid is selected from benzene sulfonic acid and toluene sulphonic acid, used in an amount of from about 0.25 to about 1.5% by weight.
Claim 5
Dependent Claim
26 words
The method of claim 3, wherein said strong acid is used in an amount of from about 0.5 to about 1.0% by weight of said resin.
Claim 6
Dependent Claim
36 words
The method of claim 1, wherein said decrease in the ratio of adsorption at a wave number of 1010 cm - 1 is from about 60 to about 95% to a value less than about 0.07.
Claim 7
Dependent Claim
31 words
The method of claim 1, wherein said first-formed resin is tacky and said contact of said resin with acid is carried out at least until the resulting resin is substantially tack-free.
Claim 8
Dependent Claim
16 words
The method of claim 6 including controlling the tack of said tack-free resin after formation thereof.
Claim 9
Dependent Claim
34 words
The method of claim 7 wherein said tack control is achieved by mixing with said tack-free resin a controlled amount of an organic solvent therefor to provide a controlled tackiness in the latter resin.
Claim 10
Dependent Claim
14 words
The method of claim 8, wherein said organic solvent is phenol or benzyl alcohol.
Claim 11
Dependent Claim
18 words
The method of claim 1, wherein the mole ratio of formaldehyde to phenol is at least about 1.5:1.
Claim 12
Dependent Claim
19 words
The method of claim 10, wherein said mole ratio of formaldehyde to phenol is about 1.5 to about 1.6:1.
Claim 13
Dependent Claim
28 words
The method of claim 1, wherein said contacting of said resin with said at least one strong acid takes place at a room temperature of about 70° F.
Claim 14
Dependent Claim
65 words
The method of claim 1 wherein said first-mentioned thermosetting phenol-formaldehyde resin is formed by a two-step reaction in which a first exothermic step is carried out until said exotherm subsides at a temperature of about 60° to about 80° C. and a second step is carried out at a temperature of about 90° to about 100° C. until the desired degree of polymerization is achieved.
Claim 15
Dependent Claim
31 words
The method of claim 13 wherein said second stage is carried out at about 100° C. until said resin has a viscosity of at least about 50,000 cps at 75° F.
Claim 16
Dependent Claim
150 words
A thermosetting phenol-formaldehyde resin having a preponderance of benzyl ether linkages ortho to the phenolic hydroxyl groups, having substantially no tendency to cure upon extensive standing at ambient temperature, being capable of rapid cure at elevated temperature, and characterized by an infra-red spectrum having the following features: a. exhibiting large absorption peaks at wave numbers of approximately 1050 cm - 1 and 1230 cm - 1 and b. a ratio of absorbance at a wave number of 1010 cm - 1 , measured from a base line drawn between wave numbers of 1030 cm - 1 and 950 cm - 1 , to that at a wave number of 1230 cm - 1 , measured from a base line drawn between wave numbers of 1130 cm - 1 and 1310 cm - 1 , which is less than about 0.1, said resin being produced by the method of claim 1.
Claim 17
Dependent Claim
15 words
The resin of claim 15, wherein said ratio of absorbance is less than about 0.07.
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) | 1980-07-18 | 1981-01-17 | 1981-07-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-18 | 1985-01-17 | 1985-07-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-18 | 1989-01-17 | 1989-07-19 | $7700.00 | Window Closed / Lapsed |