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Novel aromatic amide polyols from the reaction of phthalic acid residues, alkylene glycols and amino alcohols

Assignee: Dow Chemical Co
•
Filing: 1982-11-22
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Granted: 1984-04-10
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Expires: 2002-11-22
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Abstract

Abstract Mixtures of aromatic polyols containing tertiary amine and ester functionalities suitable for use in rigid foams prepared by reacting a phthalic acid residue with an alkylene glycol and an amino alcohol are described. These novel polyols may be blended with conventional polyols to yield rigid polyurethane foams with better flammability resistance as compared with foams made from conventional polyols alone.

Inventors

  • 👤 Robert L. Zimmerman
  • 👤 Kenneth G. McDaniel

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 23:41
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/46; C08G18/4615; C08G18/4205; C08G18/4208; C08G18/4211; C08G18/4213; C08G18/4225; C08G2115/00; C08G2115/02

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 51 words
A mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, being produced by the process comprising reacting a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, with an alkylene glycol and a tertiary amino alcohol.
Claim 2
Dependent Claim 51 words
A mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, being produced by the process comprising reacting a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, with an alkylene glycol and a tertiary amino alcohol.
Claim 3
Dependent Claim 61 words
The mixture of aromatic polyols of claim 1 in which the tertiary amino alcohol has the formula ##STR5## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c,d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4.
Claim 4
Dependent Claim 37 words
The mixture of aromatic polyols of claim 1 in which the alkylene glycol has the formula ##STR6## where R' is hydrogen or lower alkyl of one to four carbon atoms and m is from 1 to 3.
Claim 5
Dependent Claim 38 words
The mixture of aromatic polyols of claim 1 in which the reaction to make the polyol is conducted at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres.
Claim 6
Dependent Claim 28 words
The mixture of aromatic polyols of claim 1 in which the resulting mixture of aromatic polyols has an average hydroxyl number in the range between 150 and 600.
Claim 7
Dependent Claim 164 words
A mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, being produced by the process comprising reacting a. a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, b. an alkylene glycol having the formula ##STR7## where R' is hydrogen or lower alkyl of one to four carbon atoms and m is from 1 to 3, and c. a tertiary amino alcohol of the formula ##STR8## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c, d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4 at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres to produce a mixture of polyols which has an average hydroxyl number in the range between 150 and 600.
Claim 8
Dependent Claim 164 words
A mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, being produced by the process comprising reacting a. a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, b. an alkylene glycol having the formula ##STR7## where R' is hydrogen or lower alkyl of one to four carbon atoms and m is from 1 to 3, and c. a tertiary amino alcohol of the formula ##STR8## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c, d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4 at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres to produce a mixture of polyols which has an average hydroxyl number in the range between 150 and 600.
Claim 9
Independent Claim 39 words
A method for making a mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, comprising reacting a residue from the manufacture of polyethylene terephthalate, with an alkylene glycol and a tertiary amino alcohol.
Claim 10
Independent Claim 39 words
A method for making a mixture of aromatic polyols having amine and ester functionalities for use in preparing rigid foams, comprising reacting a residue from the manufacture of polyethylene terephthalate, with an alkylene glycol and a tertiary amino alcohol.
Claim 11
Dependent Claim 34 words
The method of claim 7 in which the alkylene glycol has the formula ##STR9## where R' is hydrogen or lower alkyl of one to four carbon atoms and m is from 1 to 3.
Claim 12
Dependent Claim 57 words
The method of claim 7 in which the amino alcohol has the formula ##STR10## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c,d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4.
Claim 13
Dependent Claim 31 words
The method of claim 7 in which the reaction is conducted at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres.
Claim 14
Dependent Claim 25 words
The method of claim 7 in which the resulting mixture of aromatic polyols has an average hydroxyl number in the range between 150 and 600.
Claim 15
Dependent Claim 67 words
A rigid polyurethane foam obtained by reacting in the presence of a blowing agent and a catalyst of polyurethane formation, an organic polyisocyanate and a mixture of aromatic polyols having tertiary amine and ester functionalities which is the reaction product of a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, an alkylene glycol and an amino alcohol.
Claim 16
Dependent Claim 67 words
A rigid polyurethane foam obtained by reacting in the presence of a blowing agent and a catalyst of polyurethane formation, an organic polyisocyanate and a mixture of aromatic polyols having tertiary amine and ester functionalities which is the reaction product of a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, an alkylene glycol and an amino alcohol.
Claim 17
Dependent Claim 13 words
The rigid foam of claim 12 in which the blowing agent is trichlorofluoromethane.
Claim 18
Dependent Claim 254 words
A rigid polyurethane foam obtained by reacting in the presence of a blowing agent and a catalyst of polyurethane formation, an organic polyisocyanate and an aromatic polyol blend comprising a. from about 5 to 100 percent by weight of a mixture of aromatic polyols having tertiary amine and ester functionalities made by the process comprising reacting (1) a residue taken as a waste from the production of one of the group consisting of phthalic acid, dimethyl terephthalate and polyethylene terephthalate, (2) an alkylene glycol having the formula ##STR11## where R' is hydrogen or lower alkyl and m is from 1 to 3, and (3) a tertiary amino alcohol of the formula ##STR12## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c,d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4 at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres to produce a mixture of polyols which has an average hydroxyl number in the range between 150 and 600, and b. from about 95 to 0 percent by weight of a nitrogen-containing polyol which is the reaction product from (1) reacting one mole of phenol or nonylphenol with one to two moles of ethanolamine to give a Mannich reaction product, and (2) subsequently reacting one mole of the Mannich reaction product with 2 to 3 moles of propylene oxide.
Claim 19
Dependent Claim 254 words
A rigid polyurethane foam obtained by reacting in the presence of a blowing agent and a catalyst of polyurethane formation, an organic polyisocyanate and an aromatic polyol blend comprising a. from about 5 to 100 percent by weight of a mixture of aromatic polyols having tertiary amine and ester functionalities made by the process comprising reacting (1) a residue taken as a waste from the production of one of the group consisting of phthalic acid, dimethyl terephthalate and polyethylene terephthalate, (2) an alkylene glycol having the formula ##STR11## where R' is hydrogen or lower alkyl and m is from 1 to 3, and (3) a tertiary amino alcohol of the formula ##STR12## where R and R' are hydrogen or lower alkyl of one to four carbon atoms except that R does not equal R'; a,b,c,d,e and f are from zero to 4 except that the sums a+b, c+d and e+f range from 1 to 4 at a temperature in the range between ambient and 300° C. and at a pressure between atmospheric and 2 atmospheres to produce a mixture of polyols which has an average hydroxyl number in the range between 150 and 600, and b. from about 95 to 0 percent by weight of a nitrogen-containing polyol which is the reaction product from (1) reacting one mole of phenol or nonylphenol with one to two moles of ethanolamine to give a Mannich reaction product, and (2) subsequently reacting one mole of the Mannich reaction product with 2 to 3 moles of propylene oxide.
Claim 20
Dependent Claim 23 words
The rigid polyurethane foam of claim 14 in which the polyol blend has a hydroxyl number in the range from 200 to 600.
Claim 21
Dependent Claim 14 words
The rigid polyurethane foam of claim 14 in which the blowing agent is trichlorofluoromethane.
Claim 22
Dependent Claim 68 words
A rigid polyisocyanurate foam obtained by reacting in the presence of a blowing agent and a trimerization catalyst of polyisocyanurate formation, an organic polyisocyanate and a mixture of aromatic polyols having tertiary amine and ester functionalities which is the reaction product of a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, an alkylene glycol and an amino alcohol.
Claim 23
Dependent Claim 68 words
A rigid polyisocyanurate foam obtained by reacting in the presence of a blowing agent and a trimerization catalyst of polyisocyanurate formation, an organic polyisocyanate and a mixture of aromatic polyols having tertiary amine and ester functionalities which is the reaction product of a residue selected from the group consisting of a dimethyl terephthalate manufacturing residue and a polyethylene terephthalate manufacturing residue, an alkylene glycol and an amino alcohol.
Claim 24
Dependent Claim 13 words
The rigid foam of claim 17 in which the blowing agent is trichlorofluoromethane.

References Cited (Backward Citations)

US3647759A Cited
US4048104A Cited
US4100354A Cited
US4246365A Cited
US4223068A Cited
US4237238A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-04-10 1987-10-10 1988-04-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-04-10 1991-10-10 1992-04-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-04-10 1995-10-10 1996-04-10 $7700.00 Window Closed / Lapsed

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