US3974109A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyurethanes containing halo-aryl amide-ester polyols
Assignee: Lyondell Chemical Technology LP
•
Filing: 1974-07-15
•
Granted: 1976-08-10
•
Expires: 1994-07-15
Abstract
Abstract Novel aromatic compounds are provided in which the aromatic nucleus has bonded thereto (1) at least one bromine or chlorine atom, (2) an amido group wherein nitrogen is bonded to at least one hydroxyalkyl group or an organic moiety bearing a hydroxyalkyl group, and (3) a hydroxyl-terminated oxyalkylated carboxylic acid ester group. The halogen-substituted aromatic amide-ester polyols of the invention are useful in imparting flame-retardancy to organic polymers normally susceptible to burning including polyurethanes such as, in particular, flexible polyurethane foams.
Inventors
- 👤 Anthony Joseph Papa
- 👤 William Robert Proops
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 12:16
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3823; C08G18/3825; C08K; C08K5/00; C08K5/16; C08K5/20
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
132 words
A process for producing a flame-retarded flexible polyurethane foam which comprises reacting and foaming a reaction mixture containing: (1) an organic polyisocyanate; (2) a polyether polyol having a hydroxyl number between about 32 and about 150; (3) a flame-retardant comprising a tetrabromophthalyl amide-ester triol having the formula, ##SPC4## where n and m each has a value of from 0 to about 3 and the sum n+m has an average value of from about 1 to about 3, the said flame-retardant being present in said reaction mixture in an amount sufficient to incorporate in the polyurethane product between about 2 and about 8 weight percent halogen, based on the combined weight of (1), (2) and (3); (4) a blowing agent comprising water; and (5) a catalyst comprising an amine for the polyurethane-forming reaction.
Claim 2
Dependent Claim
132 words
A process for producing a flame-retarded flexible polyurethane foam which comprises reacting and foaming a reaction mixture containing: (1) an organic polyisocyanate; (2) a polyether polyol having a hydroxyl number between about 32 and about 150; (3) a flame-retardant comprising a tetrabromophthalyl amide-ester triol having the formula, ##SPC4## where n and m each has a value of from 0 to about 3 and the sum n+m has an average value of from about 1 to about 3, the said flame-retardant being present in said reaction mixture in an amount sufficient to incorporate in the polyurethane product between about 2 and about 8 weight percent halogen, based on the combined weight of (1), (2) and (3); (4) a blowing agent comprising water; and (5) a catalyst comprising an amine for the polyurethane-forming reaction.
Claim 3
Dependent Claim
11 words
A flame-retarded flexible polyurethane foam produced as defined in claim 1.
Claim 4
Dependent Claim
140 words
A polyurethane having incorporated therein a halogen-substituted aromatic amide-ester polyol having a formula selected from the group consisting of: ##STR30## wherein: Ar is a benzene nucleus to which the indicated X, Y, amido and ester groups are bonded; X is bromine or chlorine and is positioned ortho to the amido group; Y is hydrogen, bromine or chlorine; R is a bivalent hydrocarbon group having from 1 to 6 carbon atoms; b is a number having a value from 1 to 4; R' is hydrogen, an alkyl group having from 1 to 10 carbon atoms, a bromophenyl radical, a chlorophenyl radical or --(RO) b H, wherein R and b are as aforesaid; R" is a bivalent alkylene group having from 2 to 10 carbon atoms; and c is a positive number having an average value from about 1 to about 3.
Claim 5
Dependent Claim
140 words
A polyurethane having incorporated therein a halogen-substituted aromatic amide-ester polyol having a formula selected from the group consisting of: ##STR30## wherein: Ar is a benzene nucleus to which the indicated X, Y, amido and ester groups are bonded; X is bromine or chlorine and is positioned ortho to the amido group; Y is hydrogen, bromine or chlorine; R is a bivalent hydrocarbon group having from 1 to 6 carbon atoms; b is a number having a value from 1 to 4; R' is hydrogen, an alkyl group having from 1 to 10 carbon atoms, a bromophenyl radical, a chlorophenyl radical or --(RO) b H, wherein R and b are as aforesaid; R" is a bivalent alkylene group having from 2 to 10 carbon atoms; and c is a positive number having an average value from about 1 to about 3.
Claim 6
Dependent Claim
26 words
A polyurethane as defined in claim 3 in which the halo-aryl amide-ester polyol is of formula (1) and each X and Y radical thereof is bromine.
Claim 7
Dependent Claim
26 words
A polyurethane as defined in claim 3 in which the halo-aryl amide-ester polyol is of formula (1) and each X and Y radical thereof is chlorine.
Claim 8
Dependent Claim
33 words
A polyurethane as defined in claim 3 in which the halo-aryl amide-ester polyol is of formula (1) and --(OR") c -- of the ester group thereof is oxyethylene, oxypropylene or a combination thereof.
Claim 9
Dependent Claim
40 words
A polyurethane as defined in claim 3 in which the halo-aryl amide-ester polyol is of formula (2), each X and Y radical thereof is bromine and --(OR") c -- of the ester group is oxyethylene, oxypropylene or a combination thereof.
Claim 10
Dependent Claim
158 words
A process for producing a cellular polyurethane which comprises reacting and foaming a reaction mixture containing: 1. an organic polyisocyanate; 2. a flame-retardant comprising a halo-aryl amide-ester polyol having a formula selected from the group consisting of: ##STR31## wherein: Ar is a benzene nucleus to which the indicated X, Y, amido and ester groups are bonded; X is bromine or chlorine and is positioned ortho to the amido group; Y is hydrogen, bromine or chlorine; R is a bivalent hydrocarbon group having from 1 to 6 carbon atoms; b is a number having a value from 1 to 4; R' is hydrogen, an alkyl group having from 1 to 10 carbon atoms, a bromophenyl radical, a chlorophenyl radical or --(RO) b H, where R and b are as aforesaid; R" is a bivalent alkylene group having from 2 to 10 carbon atoms; and c is a positive number having an average value from about 1 to about 3;
Claim 11
Dependent Claim
158 words
A process for producing a cellular polyurethane which comprises reacting and foaming a reaction mixture containing: 1. an organic polyisocyanate; 2. a flame-retardant comprising a halo-aryl amide-ester polyol having a formula selected from the group consisting of: ##STR31## wherein: Ar is a benzene nucleus to which the indicated X, Y, amido and ester groups are bonded; X is bromine or chlorine and is positioned ortho to the amido group; Y is hydrogen, bromine or chlorine; R is a bivalent hydrocarbon group having from 1 to 6 carbon atoms; b is a number having a value from 1 to 4; R' is hydrogen, an alkyl group having from 1 to 10 carbon atoms, a bromophenyl radical, a chlorophenyl radical or --(RO) b H, where R and b are as aforesaid; R" is a bivalent alkylene group having from 2 to 10 carbon atoms; and c is a positive number having an average value from about 1 to about 3;
Claim 12
Dependent Claim
51 words
a polyol different from polyol (2); and 4. a blowing agent; said flame-retardant being present in said reaction mixture in an amount sufficient to provide a polyurethane product having a halogen content of between about 0.2 and about 8 weight percent, based on the combined weight of (1), (2) and (3).
Claim 13
Dependent Claim
51 words
a polyol different from polyol (2); and 4. a blowing agent; said flame-retardant being present in said reaction mixture in an amount sufficient to provide a polyurethane product having a halogen content of between about 0.2 and about 8 weight percent, based on the combined weight of (1), (2) and (3).
Claim 14
Dependent Claim
21 words
A process as defined in claim 8 in which the reaction mixture contains an amine catalyst for the polyurethane forming reaction.
Claim 15
Dependent Claim
14 words
A process as defined in claim 8 in which the blowing agent is water.
Claim 16
Dependent Claim
17 words
A process as defined in claim 8 in which the blowing agent comprises water and a fluorocarbon.
Claim 17
Dependent Claim
15 words
A process as defined in claim 8 in which component (3) is a polyether polyol.
Claim 18
Dependent Claim
15 words
A process as defined in claim 8 in which component (3) is a polyester polyol.
Claim 19
Dependent Claim
15 words
A process as defined in claim 8 in which component (3) is a lactone polyol.
Claim 20
Dependent Claim
15 words
A process as defined in claim 8 in which component (3) is a phosphorus-containing polyol.
Claim 21
Dependent Claim
13 words
A cellular polyurethane produced in accordance with the process defined in claim 8.
Claim 22
Dependent Claim
110 words
A process for producing a polyurethane foam which comprises reacting and foaming a reaction mixture containing: 1. an organic polyisocyanate; 2. a polyether polyol or a polyester polyol; 3. a flame-retardant comprising a halo-aryl amide-ester triol having the formula, ##STR32## wherein: Ar is a benzene nucleus to which X, Y, the amido and ester groups are bonded, X is bromine or chlorine and is positioned ortho to the amido group, Y is hydrogen, bromine or chlorine, x has a value from 2 to 4 and n and m have respective values from zero to three, provided the average value of the sum n+m is from about 1 to about 3;
Claim 23
Dependent Claim
110 words
A process for producing a polyurethane foam which comprises reacting and foaming a reaction mixture containing: 1. an organic polyisocyanate; 2. a polyether polyol or a polyester polyol; 3. a flame-retardant comprising a halo-aryl amide-ester triol having the formula, ##STR32## wherein: Ar is a benzene nucleus to which X, Y, the amido and ester groups are bonded, X is bromine or chlorine and is positioned ortho to the amido group, Y is hydrogen, bromine or chlorine, x has a value from 2 to 4 and n and m have respective values from zero to three, provided the average value of the sum n+m is from about 1 to about 3;
Claim 24
Dependent Claim
52 words
a blowing agent comprising water; and 5. a catalyst comprising a tertiary-amine; said flame-retardant being present in said reaction mixture in an amount sufficient to provide the polyurethane product with a halogen content of between about 0.5 and about 8 weight percent, based on the combined weight of (1), (2) and (3).
Claim 25
Dependent Claim
52 words
a blowing agent comprising water; and 5. a catalyst comprising a tertiary-amine; said flame-retardant being present in said reaction mixture in an amount sufficient to provide the polyurethane product with a halogen content of between about 0.5 and about 8 weight percent, based on the combined weight of (1), (2) and (3).
Claim 26
Dependent Claim
45 words
A process as defined in claim 17 in which the ester group of said amide-ester triol is positioned ortho to the amido group, at least one of the Y radicals is bromine or chlorine, and said Y radical is positioned ortho to the ester group.
Claim 27
Dependent Claim
18 words
A process as defined in claim 18 in which the remaining two Y radicals are bromine or chlorine.
Claim 28
Dependent Claim
31 words
A process as defined in claim 17 in which the ester group of said amide-ester triol is positioned para to the amido group and each Y radical is bromine or chlorine.
Claim 29
Dependent Claim
12 words
A process as defined in claim 17 in which n is zero.
Claim 30
Dependent Claim
12 words
A process as defined in claim 17 in which m is zero.
Claim 31
Dependent Claim
15 words
A process as defined in claim 17 in which n and m are positive numbers.
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) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |