Patent US4410685A successfully refreshed from Google Patents.
US4410685A
Expired / Lapsed
US
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Hydrolytically stable urea-formaldehyde resins and process for manufacturing them
Assignee: Hexion Inc
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Filing: 1982-09-10
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Granted: 1983-10-18
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Expires: 2002-09-10
Abstract
Abstract A process for preparing a urea-formaldehyde base resin having a F/U molar ratio of 1.0:1-1.2:1, that is hydrolytically stable, which comprises adjusting a formaldehyde solution to a pH of 0.5-2.5, slowly charging urea to said formaldehyde solution while maintaining the temperature at 40°-70° C., neutralizing the reaction mixture after obtaining a Gardner viscosity in the range of T+-V+, then adding the final charge of urea and permitting equilibration.
Inventors
- 👤 James H. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 02:54
CPC Classifications
C; C08; C08L; C08L61/00; C08L61/20; C08L61/22; C08L61/24; C08G; C08G12/00; C08G12/02; C08G12/04; C08G12/10; C08G12/12; C08G12/26; C08G12/34; C08G12/36; C08G12/38; C09; C09J; C09J161/00; C09J161/20; C09J161/22; C09J161/24
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
96 words
A process for preparing a urea-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution to a pH of from about 0.5 to about 2.5, slowly charging urea to said formaldehyde solution while maintaining the temperature of the solution in the range from about 50° to about 70° C., neutralizing the reaction mixture after attaining 2.9-3.1:1 mole ratio of formaldehyde to urea and a Gardner viscosity in the range of T+-V+ and then adding the final charge of urea to achieve the desired mole ratio.
Claim 2
Dependent Claim
96 words
A process for preparing a urea-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution to a pH of from about 0.5 to about 2.5, slowly charging urea to said formaldehyde solution while maintaining the temperature of the solution in the range from about 50° to about 70° C., neutralizing the reaction mixture after attaining 2.9-3.1:1 mole ratio of formaldehyde to urea and a Gardner viscosity in the range of T+-V+ and then adding the final charge of urea to achieve the desired mole ratio.
Claim 3
Dependent Claim
12 words
The process of claim 1, wherein the mole ratio is substantially 1:1.
Claim 4
Dependent Claim
36 words
The process of claim 1 or 2 wherein the pH of the formaldehyde solution is adjusted to 0.5-2.5 using formic acid, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, or a mixture of two or more of these.
Claim 5
Dependent Claim
11 words
The process of claim 3 wherein said acid is sulfuric acid.
Claim 6
Dependent Claim
17 words
The process of claim 4 wherein the pH of the formaldehyde solution is adjusted to about 1.0.
Claim 7
Dependent Claim
26 words
The process of claim 1 or 2 wherein the reaction mixture is neutralized to a pH of 7.2-7.5 before the final charge of urea is added.
Claim 8
Dependent Claim
21 words
The process of claim 6 wherein sodium hydroxide and/or triethanolamine, or a mixture thereof, is used for neutralizing the reaction mixture.
Claim 9
Dependent Claim
25 words
The process of claim 1 or 2 wherein the reaction mixture is stirred for at least 30 minutes after adding the final charge of urea.
Claim 10
Dependent Claim
134 words
A process for preparing a urea-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, and that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution containing from about 49.8% to about 50.2% formaldehyde to a pH of 0.5-2.5 using formic acid, hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a mixture of two or more of them, slowly charging urea to said formaldehyde solution while maintaining the temperature of the solution at 50°-70° C. until a 2.9-3.0 mole ratio of formaldehyde to urea is obtained, neutralizing the reaction mixture to a pH of 7.2-7.5 after obtaining a Gardner viscosity in the range of T+-V+, using sodium hydroxide and/or triethanolamine, and adding the final charge of urea while maintaining the pH at 7.2-7.5 and stirring for at least long enough to permit equilibration.
Claim 11
Dependent Claim
134 words
A process for preparing a urea-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, and that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution containing from about 49.8% to about 50.2% formaldehyde to a pH of 0.5-2.5 using formic acid, hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a mixture of two or more of them, slowly charging urea to said formaldehyde solution while maintaining the temperature of the solution at 50°-70° C. until a 2.9-3.0 mole ratio of formaldehyde to urea is obtained, neutralizing the reaction mixture to a pH of 7.2-7.5 after obtaining a Gardner viscosity in the range of T+-V+, using sodium hydroxide and/or triethanolamine, and adding the final charge of urea while maintaining the pH at 7.2-7.5 and stirring for at least long enough to permit equilibration.
Claim 12
Dependent Claim
12 words
The process of claim 9 wherein the mole ratio is substantially 1:1.
Claim 13
Dependent Claim
25 words
A urea-formaldehyde base resin having a mole ratio of 1.0:1-1.2:1 and being hydrolytically stable which is prepared by the process of claim 1 or 9.
Claim 14
Dependent Claim
14 words
The urea-formaldehyde base resin of claim 11 wherein the mole ratio is substantially 1:1.
Claim 15
Dependent Claim
36 words
A urea-formaldehyde liquid base resin comprising urea and formaldehyde in a mole ratio of 1.0:1-1.2:1, said resin containing essentially no free formaldehyde and said resin when cured containing substantially more methylene groups than methylene ether groups.
Claim 16
Dependent Claim
36 words
A urea-formaldehyde liquid base resin comprising urea and formaldehyde in a mole ratio of 1.0:1-1.2:1, said resin containing essentially no free formaldehyde and said resin when cured containing substantially more methylene groups than methylene ether groups.
Claim 17
Dependent Claim
15 words
The urea-formaldehyde liquid base resin of claim 13 wherein the mole ratio is substantially 1:1.
Claim 18
Dependent Claim
17 words
The liquid base resin of claim 14 comprising 24.89 weight percent formaldehyde and 49.78 weight percent urea.
Claim 19
Dependent Claim
27 words
The resin of claim 15 which further comprises 0.06 weight percent sulfuric acid, 0.05 weight percent sodium hydroxide, and 0.33 weight percent triethanolamine, the balance comprising water.
Claim 20
Dependent Claim
62 words
The resin of claim 13, 14, 15 or 16 having a solids content from about 61% to about 65%, a specific gravity of 1.250 to 1.270, a Brookfield viscosity from about 100 cps to about 400 cps as measured at 25° C. on an RVF viscometer, #1 spindle, at 20 rpm, and having a refractive index from about 1.4600 to about 1.4700.
Claim 21
Dependent Claim
21 words
A resin according to claim 13 that when cured contains more than twice as many methylene groups as methylene ether groups.
Claim 22
Dependent Claim
15 words
A resin according to claim 13 or 14 that is essentially free of methylol groups.
Claim 23
Dependent Claim
21 words
The resin of claim 13 or 14 which when cured contains at least 2.5 methylene groups per 1 methylene ether group.
Claim 24
Dependent Claim
32 words
A urea-formaldehyde liquid base resin comprising 24.89 weight percent formaldehyde, 49.78 weight percent urea, 0.06 weight percent sulfuric acid, 0.05 weight percent sodium hydroxide, 0.33 weight percent triethanolamine, and the balance, water.
Claim 25
Dependent Claim
32 words
A urea-formaldehyde liquid base resin comprising 24.89 weight percent formaldehyde, 49.78 weight percent urea, 0.06 weight percent sulfuric acid, 0.05 weight percent sodium hydroxide, 0.33 weight percent triethanolamine, and the balance, water.
Claim 26
Dependent Claim
36 words
A process for curing a resin prepared in accordance with claim 1 or 2 comprising heating said resin at a pH in the range from about 7.2 to about 7.5 at 135° C. to 193° C.
Claim 27
Dependent Claim
32 words
A process in accordance with claim 22 including, as a preliminary step prior to heat curing, the step of mixing the liquid base resin with a cross-linking agent, then heating to cure.
Claim 28
Dependent Claim
30 words
A process according to claim 22 including a preliminary step, prior to heat curing the resin, of mixing the liquid base resin with an acid-reacting catalyst, then heating to cure.
Claim 29
Dependent Claim
34 words
A process according to claim 23 wherein the cross-linking reagent contains at least two functional groups of the formula ##STR8## per molecule where R is an alkyl group of from 1 to 24 carbons.
Claim 30
Dependent Claim
12 words
A process according to claim 25 wherein the cross-linking agent is trimethoxymethylmelamine.
Claim 31
Dependent Claim
11 words
The process of claim 25 wherein the cross-linking agent is hexamethoxymethylmelamine.
Claim 32
Dependent Claim
26 words
The process of claim 25 wherein the cross-linking agent is a methoxylated urea formaldehyde resin having the formula ##STR9## wherein n is an integer from 1-6.
Claim 33
Dependent Claim
40 words
A curable liquid base resin formulation that can be heat cured to form a cross-linked structure comprising in combination a liquid base resin produced according to claim 1, 2, 9 or 10 together with a cross-linking agent for the resin.
Claim 34
Dependent Claim
12 words
The resin formulation of claim 29 in combination with an external catalyst.
Claim 35
Dependent Claim
26 words
The formulation of claim 29 that, upon curing, has a cross-linked structure containing essentially no free formaldehyde and substantially more methylene groups than methylene ether groups.
Claim 36
Dependent Claim
18 words
The cured resin of claim 31 containing more than twice as many methylene groups as methylene ether groups.
Claim 37
Dependent Claim
13 words
The cured resin of claim 32 that is essentially free of methylol groups.
Claim 38
Dependent Claim
56 words
A curable resin formulation containing a urea formaldehyde liquid base resin prepared according to claim 1, 2, 9 or 10, in combination with a cross-linking agent, each molecule of which has at least two groups reactive with a member of the group consisting of amine, carbonyl, and hydroxy groups, which are present in the liquid resin.
Claim 39
Dependent Claim
37 words
The resin formulation of claim 34 wherein the cross-linking agent contains at least two functional groups of the formula --N--CH.sub.2 --O--R per molecule where R is an alkyl or hydroxy alkyl group of 1 to 24 carbons.
Claim 40
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 29.
Claim 41
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 30.
Claim 42
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 31.
Claim 43
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 34.
Claim 44
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 35.
Claim 45
Dependent Claim
102 words
A process for preparing a amino-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, and that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution to a pH of from about 0.5 to about 2.5, slowly charging an amino compound to said formaldehyde solution while maintaining the temperature of the solution at 50°-70° C. until a 2.9-3.0 mole ratio of formaldehyde to the compound is obtained, neutralizing the reaction mixture to a pH of 7.2-7.5 after obtaining a Gardner viscosity in the range of T+-V+, and adding the final charge of the amino compound to achieve the desired mole ratio.
Claim 46
Dependent Claim
102 words
A process for preparing a amino-formaldehyde base resin having a F/U mole ratio of 1.0:1-1.2:1, and that is hydrolytically stable, which comprises adjusting an aqueous formaldehyde solution to a pH of from about 0.5 to about 2.5, slowly charging an amino compound to said formaldehyde solution while maintaining the temperature of the solution at 50°-70° C. until a 2.9-3.0 mole ratio of formaldehyde to the compound is obtained, neutralizing the reaction mixture to a pH of 7.2-7.5 after obtaining a Gardner viscosity in the range of T+-V+, and adding the final charge of the amino compound to achieve the desired mole ratio.
Claim 47
Dependent Claim
12 words
The process of claim 41 wherein said resin is a urea-melamine-formaldehyde resin.
Claim 48
Dependent Claim
38 words
An amino-formaldehyde liquid base resin comprising an amino compound and formaldehyde in a mole ratio of 1.0:1-1.2:1, said resin containing essentially no free formaldehyde and said resin when cured containing substantially more methylene groups than methylene ether groups.
Claim 49
Dependent Claim
38 words
An amino-formaldehyde liquid base resin comprising an amino compound and formaldehyde in a mole ratio of 1.0:1-1.2:1, said resin containing essentially no free formaldehyde and said resin when cured containing substantially more methylene groups than methylene ether groups.
Claim 50
Dependent Claim
14 words
The resin of claim 43 wherein amino is a mixture of urea and melamine.
Claim 51
Dependent Claim
38 words
A curable liquid base resin formulation that can be heat cured to form a cross-linked structure comprising in combination a liquid base resin produced according to claim 41 or 42 together with a cross-linking agent for the resin.
Claim 52
Dependent Claim
54 words
A curable resin formulation containing a urea formaldehyde liquid base resin prepared according to claim 41 or 42, in combination with a cross-linking agent, each molecule of which has at least two groups reactive with a member or the group consisting of amine, carbonyl, and hydroxy groups, which are present in the liquid resin.
Claim 53
Dependent Claim
14 words
A cured, cross-linked resin obtained by heat curing a formulation according to claim 46.
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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) | 1986-10-17 | 1987-04-18 | 1987-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-17 | 1991-04-18 | 1991-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-17 | 1995-04-18 | 1995-10-18 | $7700.00 | Window Closed / Lapsed |