Patent US4002580A successfully refreshed from Google Patents.
US4002580A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Fire-retardant polyurethane
Assignee: ISP Investments LLC
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Filing: 1974-09-12
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Granted: 1977-01-11
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Expires: 1994-09-12
Abstract
Abstract Polyurethanes incorporating 2,3-dibromobutenediol-1.4, as a reactive fire-retardant component and chain extender, in combination with organophosphorous compounds, to effect a decrease in the amount of brominated diol necessary, and thus in the bromine content of the resin, to provide fire-retardant polyurethane products manifesting significantly reduced smoke emission in the event of combustion and other enhanced physical properties.
Inventors
- 👤 Robert Victor Russo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:51
CPC Classifications
C; C08; C08J; C08J9/00; C08J9/0014; C08J9/0038; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/675; C08G18/677; C08G18/6775; C08K; C08K5/00; C08K5/49; C08K5/51; C08K5/53; C08K5/5317; C08K5/5333; C08K5/5357; C08J2375/00; C08J2375/04
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
307 words
The process of producing a polyurethane that comprises reacting an halogenated polyether or polyester polyol, an organic polyisocyanate, 2,3-dibromo-2-butenediol-1,4, and a phosphorus-containing compound selected from the formulae: ##STR9## and mixtures thereof; wherein each of a and b has a value of 0 to 2 inclusive; c is an integer of from 1 to 3 and the sum of a, b, and c is 3; each of R and R 1 is an alkyl, alkoxy, aryloxy, alkaryl, alkaryloxy, aralkyl, aryloxyalkoxy, or aralkoxy radical wherein each of said alkyl moieties is unsubstituted or hydroxy-substituted; and each of any aryl portion of said radical is an unsubstituted, or hydroxy- or chlorine-substituted aromatic hydrocarbon; R 2 is an alkyl, hydroxyalkyl, or unsubstituted aromatic hydrocarbon radical; R 3 is an alkyl or hydroxyalkyl radical; d has a value of from 0 to 2 inclusive; e is an integer of from 1 to 3 inclusive; and the sum of d and e is not in excess of 3; R 4 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl portion of said group is an unsubstituted, or chlorine- or hydroxy-substituted aromatic hydrocarbon; R 5 is an alkyl, alkylene, aryl or arylene radical; and each of said aryl and arylene radicals is an unsubstituted or chlorine- or hydroxy-substituted aromatic hydrocarbon moiety; and R 6 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl moiety present is an unsubstituted, hydroxy-substituted or chlorine substituted aromatic hydrocarbon moiety; and wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide a final polymer containing weight percents of bromine (Br) and phosphorus (P) defined by the equation: P + Br/10 ≅ 0.1 to 1.0 and wherein P has a value of not less than 0.05 weight percent and Br has a value not less than 0.5 weight percent.
Claim 2
Dependent Claim
307 words
The process of producing a polyurethane that comprises reacting an halogenated polyether or polyester polyol, an organic polyisocyanate, 2,3-dibromo-2-butenediol-1,4, and a phosphorus-containing compound selected from the formulae: ##STR9## and mixtures thereof; wherein each of a and b has a value of 0 to 2 inclusive; c is an integer of from 1 to 3 and the sum of a, b, and c is 3; each of R and R 1 is an alkyl, alkoxy, aryloxy, alkaryl, alkaryloxy, aralkyl, aryloxyalkoxy, or aralkoxy radical wherein each of said alkyl moieties is unsubstituted or hydroxy-substituted; and each of any aryl portion of said radical is an unsubstituted, or hydroxy- or chlorine-substituted aromatic hydrocarbon; R 2 is an alkyl, hydroxyalkyl, or unsubstituted aromatic hydrocarbon radical; R 3 is an alkyl or hydroxyalkyl radical; d has a value of from 0 to 2 inclusive; e is an integer of from 1 to 3 inclusive; and the sum of d and e is not in excess of 3; R 4 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl portion of said group is an unsubstituted, or chlorine- or hydroxy-substituted aromatic hydrocarbon; R 5 is an alkyl, alkylene, aryl or arylene radical; and each of said aryl and arylene radicals is an unsubstituted or chlorine- or hydroxy-substituted aromatic hydrocarbon moiety; and R 6 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl moiety present is an unsubstituted, hydroxy-substituted or chlorine substituted aromatic hydrocarbon moiety; and wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide a final polymer containing weight percents of bromine (Br) and phosphorus (P) defined by the equation: P + Br/10 ≅ 0.1 to 1.0 and wherein P has a value of not less than 0.05 weight percent and Br has a value not less than 0.5 weight percent.
Claim 3
Dependent Claim
45 words
The process of claim 1 wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide a final polymer containing not in excess of 0.95 weight percent of phosphorus (P) and not in excess of 9.5 weight percent of bromine (Br).
Claim 4
Dependent Claim
24 words
The process of claim 2 wherein P has a value of 0.14 weight percent and Br has a value of about 2.2 weight percent.
Claim 5
Dependent Claim
14 words
The process of claim 1 wherein said phosphorus-containing compound has the structural formula: ##STR10##
Claim 6
Dependent Claim
14 words
The process of claim 1 wherein said phosphorus-containing compound has the structural formula: ##STR11##
Claim 7
Dependent Claim
14 words
The process of claim 1 wherein said phosphorus-containing compound has the structural formula: ##STR12##
Claim 8
Dependent Claim
14 words
The process of claim 1 wherein said phosphorus-containing compound has the structural formula: ##STR13##
Claim 9
Dependent Claim
14 words
The process of claim 1 wherein said phosphorus-containing compound has the structural formula: ##STR14##
Claim 10
Dependent Claim
25 words
The process of claim 1 wherein said reaction takes place in the presence of a blowing agent and catalyst to produce a cellular polyurethane foam.
Claim 11
Dependent Claim
308 words
A polyurethane produced by reaction of an unhalogenated polyether polyol, an organic polyisocyanate, 2,3-dibromo-2-butenediol-1,4, and a phosphourus-containing compound selected from the formulea: ##STR15## and mixtures thereof; wherein each of a and b has a value of 0 to 2 inclusive; c is an integer of from 1 to 3 and the sum of a, b, and c is 3; each of R and R 1 is an alkyl, alkoxy, aryloxy, alkaryl, alkaryloxy, aralkyl, arloxyalkoxy, or aralkoxy radical wherein each of said alkyl moieties is unsubstituted or hydroxy-substituted; and each of any aryl portion of said radical is an unsubstituted, or hydroxy- or chlorine-substituted aromatic hydrocarbon; R 2 is an alkyl, hydroxyalkyl, or unsubstituted aromatic hydrocarbon radical; R 3 is an alkyl or hydroxy-alkyl radical; d has a value of from 0 to 2 inclusive; e is an integer of from 1 to 3 inclusive; and the sum of d and e is not in excess of 3; R 4 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group, wherein any aryl portion of said group is an unsubstituted, or chlorine- or hydroxy-substituted aromatic hydrocarbon; R 5 is an alkyl, alkylene, aryl or arylene radical; and each of said aryl and arylene radicals is an unsubstituted or chlorine- or hydroxy-substituted aromatic hydrocarbon moiety; and R 6 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl moiety present is an unsubstituted, hydroxy-substituted or chlorine-substituted aromatic hydrocarbon moiety; and wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide by weight percent of the final product a sum total of bromine (Br) and phosphorus (P), defined by the equation: P + Br/10 ≅ 0.1 to 1.0 and wherein phosphorus (P) has a value of not less than 0.05 weight percent and bromine (Br) has a value of not less than 0.5 weight percent.
Claim 12
Dependent Claim
308 words
A polyurethane produced by reaction of an unhalogenated polyether polyol, an organic polyisocyanate, 2,3-dibromo-2-butenediol-1,4, and a phosphourus-containing compound selected from the formulea: ##STR15## and mixtures thereof; wherein each of a and b has a value of 0 to 2 inclusive; c is an integer of from 1 to 3 and the sum of a, b, and c is 3; each of R and R 1 is an alkyl, alkoxy, aryloxy, alkaryl, alkaryloxy, aralkyl, arloxyalkoxy, or aralkoxy radical wherein each of said alkyl moieties is unsubstituted or hydroxy-substituted; and each of any aryl portion of said radical is an unsubstituted, or hydroxy- or chlorine-substituted aromatic hydrocarbon; R 2 is an alkyl, hydroxyalkyl, or unsubstituted aromatic hydrocarbon radical; R 3 is an alkyl or hydroxy-alkyl radical; d has a value of from 0 to 2 inclusive; e is an integer of from 1 to 3 inclusive; and the sum of d and e is not in excess of 3; R 4 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group, wherein any aryl portion of said group is an unsubstituted, or chlorine- or hydroxy-substituted aromatic hydrocarbon; R 5 is an alkyl, alkylene, aryl or arylene radical; and each of said aryl and arylene radicals is an unsubstituted or chlorine- or hydroxy-substituted aromatic hydrocarbon moiety; and R 6 is an alkyl, aryl, alkaryl, aralkyl or aryloxyalkyl group wherein any aryl moiety present is an unsubstituted, hydroxy-substituted or chlorine-substituted aromatic hydrocarbon moiety; and wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide by weight percent of the final product a sum total of bromine (Br) and phosphorus (P), defined by the equation: P + Br/10 ≅ 0.1 to 1.0 and wherein phosphorus (P) has a value of not less than 0.05 weight percent and bromine (Br) has a value of not less than 0.5 weight percent.
Claim 13
Dependent Claim
47 words
A polyurethane as claimed in claim 10 wherein said 2,3-dibromo-2-butenediol-1,4 and said phosphorus-containing compound are present in an amount sufficient to provide a final product comprising not in excess of 0.95 weight percent of phosphorus (P) and not in excess of 9.5 weight percent of bromine (Br).
Claim 14
Dependent Claim
26 words
A polyurethane as claimed in claim 11 wherein P has a value of 0.14 weight percent and Br has a value of about 2.2 weight percent.
Claim 15
Dependent Claim
16 words
A polyurethane as claimed in claim 10 wherein said phosphorus-containing compound has the structural formula: ##STR16##
Claim 16
Dependent Claim
16 words
A polyurethane as claimed in claim 10 wherein said phosphorus-containing compound has the structural formula: ##STR17##
Claim 17
Dependent Claim
16 words
A polyurethane as claimed in claim 10 wherein said phosphorus-containing compound has the structural formula: ##STR18##
Claim 18
Dependent Claim
16 words
A polyurethane as claimed in claim 10 wherein said phosphorus-containing compound has the structural formula: ##STR19##
Claim 19
Dependent Claim
16 words
A polyurethane as claimed in claim 10 wherein said phosphorus-containing compound has the structural formula: ##STR20##
Claim 20
Dependent Claim
20 words
A polyurethane as claimed in claim 10 wherein said polyurethane is a cured, flexible, stable polyester or polyether urethane foam.
Claim 21
Dependent Claim
28 words
A polyurethane foam as claimed in claim 18 wherein said foam is a cured, stable, fire-retardant, high-resilience polyether urethane foam having a sag factor of at least 2.2.
Claim 22
Dependent Claim
20 words
A high-resilience polyether urethane foam as claimed in claim 19 having a sag factor of from about 2.4 to 3.1.
Claim 23
Dependent Claim
19 words
A high-resilience polyether urethane foam as claimed in claim 20 wherein said polyether polyol is a linear polyether triol.
Claim 24
Dependent Claim
26 words
A high-resilience polyether urethane foam as claimed in claim 21 wherein said polyether is a poly (oxypropoylene) triol having a molecular weight of at least 4000.
Claim 25
Dependent Claim
23 words
The high-resilience foam as claimed in claim 22 wherein said poly(oxypropylene) triol has a molecular weight of from about 4,000 to about 7,000.
References Cited (Backward Citations)
GB1305036A
Cited
US3812047A
Cited
US3933690A
Cited
US3779953A
Cited
US3772222A
Cited
US3738953A
Cited
US3919166A
Cited
US3862879A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-11 | 1980-07-12 | 1981-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-11 | 1984-07-12 | 1985-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-11 | 1988-07-12 | 1989-01-11 | $7700.00 | Window Closed / Lapsed |