Patent US4383102A successfully refreshed from Google Patents.
US4383102A
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Method for producing a low viscosity spray polyol by reacting an alkylene oxide with the reaction product of a phenol, an amine and a smaller formaldehyde portion
Assignee: Dow Chemical Co
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Filing: 1982-01-29
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Granted: 1983-05-10
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Expires: 2002-01-29
Abstract
Abstract An improved method for the production of polyols useful in the application of sprayed high density polyurethane foams is described. The improvement involves varying the formaldehyde to phenol mole ratio to range between 1.25:1 to 1.75:1 to produce a polyol with the desired viscosity. Ordinarily such polyols are prepared by reacting 4.65 to 5 moles of propylene oxide with 1 mole of the Mannich reaction product of a mole of phenol or nonylphenol with 1 or 2 moles of diethanolamine and 1 or 2 moles of formaldehyde. It is particularly surprising that such changes in the formulation may be made without adversely affecting the resultant properties of the spray foam.
Inventors
- 👤 Kenneth G. McDaniel
- 👤 George P. Speranza
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:50
CPC Classifications
C; C08; C08G; C08G14/00; C08G14/02; C08G14/04; C08G14/12; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C08G18/5033; C08G18/54; C08G18/546; C08G2110/00; C08G2110/0025; C08G2110/0041; C08G2110/005; C08G2150/00; C08G2150/60
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
249 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol, an amine and formaldehyde, (1) the amine being selected from the group consisting of ammonia and alkanolamines having the formula: ##STR7## where R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and --(CHR) n --OH and n is a positive integer having a value of two to five, (2) the molar ratio of phenol to amine being about 1:2, and (3) the molar ratio of formaldehyde to phenol being from about 1.25:1 to about 1.75:1; b. heating the resulting mixture at a temperature within the range of from about 50 to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; c. stripping the water from the reaction product; d. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30 to 200° C.; and e. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 2
Independent Claim
249 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol, an amine and formaldehyde, (1) the amine being selected from the group consisting of ammonia and alkanolamines having the formula: ##STR7## where R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and --(CHR) n --OH and n is a positive integer having a value of two to five, (2) the molar ratio of phenol to amine being about 1:2, and (3) the molar ratio of formaldehyde to phenol being from about 1.25:1 to about 1.75:1; b. heating the resulting mixture at a temperature within the range of from about 50 to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; c. stripping the water from the reaction product; d. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30 to 200° C.; and e. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 3
Dependent Claim
11 words
The method of claim 1 in which the amine is diethanolamine.
Claim 4
Dependent Claim
25 words
The method of claim 2 in which the alkylene oxide portion is selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
Claim 5
Dependent Claim
22 words
The method of claim 1 in which the alkylene oxide portion consists of propylene oxide and ethylene oxide added separately or together.
Claim 6
Dependent Claim
15 words
A product as prepared by the method described in claim 1, 2, 3 or 4.
Claim 7
Independent Claim
248 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol and an alkanolamine selected from the group consisting of alkanolamines having the formula: ##STR8## wherein R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and--(CHR) n --OH and n is a positive integer having a value of two to five, the molar ratio of phenol to alkanolamine being about 1:2; b. adding formaldehyde to the mixture in proportions such that the molar ratio of formaldehyde to phenol ranges from about 1.25:1 to about 1.75:1; c. heating the resulting mixture at a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 8
Independent Claim
248 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol and an alkanolamine selected from the group consisting of alkanolamines having the formula: ##STR8## wherein R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and--(CHR) n --OH and n is a positive integer having a value of two to five, the molar ratio of phenol to alkanolamine being about 1:2; b. adding formaldehyde to the mixture in proportions such that the molar ratio of formaldehyde to phenol ranges from about 1.25:1 to about 1.75:1; c. heating the resulting mixture at a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 9
Dependent Claim
11 words
The method of claim 6 in which the alkanolamine is diethanolamine.
Claim 10
Dependent Claim
25 words
The method of claim 7 in which the alkylene oxide portion is selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
Claim 11
Dependent Claim
22 words
The method of claim 6 in which the alkylene oxide portion consists of propylene oxide and ethylene oxide added separately or together.
Claim 12
Dependent Claim
15 words
A product as prepared by the method described in claim 6, 7, 8 or 9.
Claim 13
Independent Claim
175 words
A method for producing a low viscosity, nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing nonylphenol and diethanolamine, the molar ratio of nonylphenol to diethanolamine being about 1:2; b. adding formaldehyde to the mixture in proportions such that the molar ratio of formaldehyde to nonylphenol is in the range of about 1.25:1 to about 1.75:1; c. heating the resulting mixture at a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding propylene oxide and ethylene oxide separately or together to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 14
Independent Claim
175 words
A method for producing a low viscosity, nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing nonylphenol and diethanolamine, the molar ratio of nonylphenol to diethanolamine being about 1:2; b. adding formaldehyde to the mixture in proportions such that the molar ratio of formaldehyde to nonylphenol is in the range of about 1.25:1 to about 1.75:1; c. heating the resulting mixture at a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding propylene oxide and ethylene oxide separately or together to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 15
Dependent Claim
11 words
A product as prepared by the method described in claim 11.
Claim 16
Independent Claim
244 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol and formaldehyde such that the molar ratio of formaldehyde to phenol is in the range of about 1.25:1 to about 1.75:1; b. adding an alkanolamine selected from the group consisting of alkanolamines having the formula: ##STR9## wherein R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and --(CHR) n --OH and n is a positive integer of two to five, the molar ratio of phenol to alkanolamine being about 1:2; c. heating the resulting mixture of a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 17
Independent Claim
244 words
A method for producing a low viscosity nitrogen-containing polyol suitable for use in sprayed, high density, rigid polyurethane foam, comprising the steps of a. mixing a phenol and formaldehyde such that the molar ratio of formaldehyde to phenol is in the range of about 1.25:1 to about 1.75:1; b. adding an alkanolamine selected from the group consisting of alkanolamines having the formula: ##STR9## wherein R is selected from the group consisting of hydrogen and C 1 -C 4 alkyl, R' is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and --(CHR) n --OH and n is a positive integer of two to five, the molar ratio of phenol to alkanolamine being about 1:2; c. heating the resulting mixture of a temperature within the range of from about 50° to 150° C. for a period of time sufficient to reduce the formaldehyde content to no more than about 1 wt.%; d. stripping the water from the reaction product; e. adding separately or together at least two different alkylene oxides selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, and glycidol to said stripped reaction product at a temperature within the range of about 30° to 200° C.; and f. recovering a nitrogen-containing polyol having a hydroxyl number of from about 250 to about 900, a nitrogen content of from about 1 to about 15 wt.% and a viscosity of 15,000 centipoise or less at 25° C.
Claim 18
Dependent Claim
11 words
The method of claim 13 in which the alkanolamine is diethanolamine.
Claim 19
Dependent Claim
25 words
The method of claim 14 in which the alkylene oxide portion is selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
Claim 20
Dependent Claim
22 words
The method of claim 13 in which the alkylene oxide portion consists of propylene oxide and ethylene oxide added separately or together.
Claim 21
Dependent Claim
15 words
A product as prepared by the method described in claim 13, 14, 15 or 16.
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) | 1986-05-09 | 1986-11-08 | 1987-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-09 | 1990-11-08 | 1991-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-09 | 1994-11-08 | 1995-05-10 | $7700.00 | Window Closed / Lapsed |