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US4444918A Expired / Lapsed US ⏱️ 0.0 years remaining

Aromatic polyols made from waste streams from the manufacture of terephthalic acids, alkylene glycols and dibasic acids

Assignee: Dow Chemical Co
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Filing: 1982-11-22
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Granted: 1984-04-24
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Expires: 2002-11-22
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Abstract

Abstract Mixtures of aromatic polyols containing ester functionalities suitable for use in rigid foams prepared by reacting dibasic acid residues with an alkylene glycol residue, the reaction product of which is reacted with terephthalic acid residues are described. These novel polyols may be blended with conventional polyols to yield excellent rigid foams, thus serving as useful polyol extenders. These low hydroxyl number extender polyols unexpectedly have a low relative viscosity.

Inventors

  • 👤 Michael E. Brennan

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 19:44
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4205; C08G18/4208; C08G18/4225; C08G18/4211; C08G18/4216; C08G2110/00; C08G2110/0025; C08G2110/0041; C08G2110/005

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 75 words
A mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, being produced by the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 2
Dependent Claim 75 words
A mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, being produced by the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 3
Dependent Claim 37 words
The mixture of aromatic polyols of claim 1 in which the alkylene glycol has the formula ##STR4## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and n is from 1 to 3.
Claim 4
Dependent Claim 17 words
The mixture of polyols of claim 1 in which the alkylene glycol is a glycol waste stream.
Claim 5
Dependent Claim 23 words
The mixture of polyols of claim 1 in which the terephthalic ester waste stream is a residue from the manufacture of dimethyl terephthalate.
Claim 6
Dependent Claim 44 words
The mixture of polyols of claim 4 in which the dimethyl terephthalate residue contains dimethyl terephthalate and one or more by-products selected from the group consisting of substituted benzenes, polycarbomethoxy diphenyls, benzyl esters of the toluate family, dicarbomethoxy fluorenone, carbomethoxy benzocoumarins and carbomethoxy polyphenyls.
Claim 7
Dependent Claim 28 words
The mixture of polyols of claim 1 in which the terephthalic ester waste stream is selected from the group consisting of residue from the manufacture of polyethylene terephthalate.
Claim 8
Dependent Claim 30 words
The mixture of polyols of claim 1 in which the reactions are conducted at a temperature between 160° to 240° C. and at a pressure between one atmosphere and subatmospheric.
Claim 9
Dependent Claim 22 words
The mixture of polyols of claim 1 in which the average hydroxyl number of the resultant mixture is between 100 and 400.
Claim 10
Dependent Claim 164 words
A mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, being produced by the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids selected from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol waste stream containing alkylene glycols of the formula ##STR5## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and n is from 1 to 3, to produce a polyester polyol, and b. transesterifying a terephthalic ester residue which is selected from the group consisting of manufacturing waste streams of dimethyl terephthalate or polyethylene terephthalate and mixtures thereof, with the polyester polyol reaction product from the previous step, such that the reactions are conducted at a temperature between 160° to 240° C. and at a pressure between one atmosphere and subatmospheric and in which the average hydroxyl number of the resultant polyol mixture is between 100 and 400.
Claim 11
Dependent Claim 164 words
A mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, being produced by the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids selected from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol waste stream containing alkylene glycols of the formula ##STR5## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and n is from 1 to 3, to produce a polyester polyol, and b. transesterifying a terephthalic ester residue which is selected from the group consisting of manufacturing waste streams of dimethyl terephthalate or polyethylene terephthalate and mixtures thereof, with the polyester polyol reaction product from the previous step, such that the reactions are conducted at a temperature between 160° to 240° C. and at a pressure between one atmosphere and subatmospheric and in which the average hydroxyl number of the resultant polyol mixture is between 100 and 400.
Claim 12
Independent Claim 74 words
A method for making a mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol, and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 13
Independent Claim 74 words
A method for making a mixture of aromatic polyols having hydroxyl and ester functionalities for use in preparing rigid foams, comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol, and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 14
Dependent Claim 62 words
The method of claim 10 in which a. the alkylene glycol is a glycol waste stream comprising alkylene glycols of the formula ##STR6## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and n is from 1 to 3, and b. the terephthalic ester waste stream is a residue from the manufacture of dimethyl terephthalate or polyethylene terephthalate.
Claim 15
Dependent Claim 28 words
The method of claim 10 in which the reactions are conducted at a temperature between 160° and 240° C. and at a pressure between one atmosphere and subatmospheric.
Claim 16
Dependent Claim 20 words
The method of claim 10 in which the average hydroxyl number of the resultant mixture is between 100 and 400.
Claim 17
Dependent Claim 165 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 polyol blend comprising a. from about 5 to 100 percent by weight of a mixture of aromatic polyols having ester functionalities which is the reaction product from (1) esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and (2) transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step, and b. from about 95 to 0 percent by weight of a nitrogen-containing polyol which is the reaction product from (1) reacting one mode of phenol or nonylphenol with one to 2 moles of diethanolamine 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 18
Dependent Claim 165 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 polyol blend comprising a. from about 5 to 100 percent by weight of a mixture of aromatic polyols having ester functionalities which is the reaction product from (1) esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and (2) transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step, and b. from about 95 to 0 percent by weight of a nitrogen-containing polyol which is the reaction product from (1) reacting one mode of phenol or nonylphenol with one to 2 moles of diethanolamine 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 24 words
The rigid polyurethane foam of claim 14 in which the polyol blend has an average hydroxyl number in the range from 100 to 400.
Claim 20
Dependent Claim 14 words
The rigid polyurethane foam of claim 14 in which the blowing agent is trichlorofluoromethane.
Claim 21
Dependent Claim 97 words
A rigid polyisocyanurate foam which is 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 ester functionalities which is the reaction product of the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 22
Dependent Claim 97 words
A rigid polyisocyanurate foam which is 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 ester functionalities which is the reaction product of the process comprising a. esterifying a residue from dibasic acid manufacture which comprises one or more acids from the group consisting of glutaric acid, succinic acid and adipic acid, with an alkylene glycol to produce a polyester polyol and b. transesterifying a terephthalic ester waste stream with the polyester polyol reaction product from the previous step.
Claim 23
Dependent Claim 26 words
The rigid polyisocyanurate foam of claim 17 in which the mixture of aromatic polyols have an average hydroxyl number in the range of 100 to 400.
Claim 24
Dependent Claim 14 words
The rigid polyisocyanurate foam of claim 17 in which the blowing agent is trichlorofluoromethane.

References Cited (Backward Citations)

US3590070A Cited
US4048104A Cited
US4223068A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-04-24 1987-10-24 1988-04-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-04-24 1991-10-24 1992-04-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-04-24 1995-10-24 1996-04-24 $7700.00 Window Closed / Lapsed

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