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US4559370A
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Copolyester polyol resins, polyol blends comprising the same, and resultant polyisocyanurate foams
Assignee: Cook Composites and Polymers Co
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Filing: 1984-05-25
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Granted: 1985-12-17
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Expires: 2004-05-25
Abstract
Abstract Copolyester polyol resins comprising the reaction product of an aromatic component selected from phthalic derivatives, polyethylene terephthalate, or dimethyl terephthalate, an aliphatic component selected from certain dibasic compounds, at least one primary hydroxyl glycol, and at least small amounts of a secondary hydroxyl glycol, the mole ratios of the components being: (a) glycols to aromatic plus aliphatic component of from about 1.3 to 2:1; (b) aromatic component to aliphatic component of from about 0.6 to 4.0:1; (c) a secondary to primary hydroxyl glycol of from 0.05 to 0.4:1; and (d) ethylene glycol content to aromatic component of from about 0.01 to 0.5:1.0. The invention also comprises polyol blends utilizing from 30 percent up to 90 percent of such resins and resultant polyurethane modified polyisocyanurate foams made by reacting such polyol blends with polymeric polymethylene polyphenylisocyanate. Also disclosed is a method to digest polyethylene terephthalate waste and remove a majority of the ethylene glycol formed during digestion.
Inventors
- 👤 Robert H. Blanpied
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:34
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4244; C08G18/4247; C08G18/4205; C08G18/4208; C08G18/4211; C08G18/4213; C08G18/4216; C08G2110/00; C08G2110/0041; C08G2115/00; C08G2115/02
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
186 words
A hydroxyl terminated copolyester polyol resin having a functionality of about 2, comprising the reaction product of: A. an aromatic component selected from phthalic anhydride; phthalic acid isomers; phthalic acid halide isomers; di-lower alkanol esters of phthalic acid isomers; digestion products of polyethylene terephthalate; or mixtures thereof; B. at least one aliphatic component selected from succinic anhydride; succinic, glutaric, or adipic acids; di-lower alkanol esters of succinic, glutaric, or adipic acids; acid halides of succinic, glutaric, or adipic acids; or mixtures thereof; and C. at least one primary hydroxyl glycol; and D. at least one secondary hydroxyl glycol; the mole ratios of the components being: (1) glycols to aromatic plus aliphatic component of from about 1.3 to 2:1; (2) aromatic component to aliphatic component of from about 0.6 to 4.0:1; (3) a secondary to primary hydroxyl glycol of from 0.05 to 0.4:1, where all mole ratios represent the final mole ratios inasmuch as glycols may be removed during processing; and (4) ethylene glycol content to aromatic component of from about 0.01 to 0.5:1.0 when a digestion product of polyethylene terephthalate is used as the aromatic component.
Claim 2
Dependent Claim
186 words
A hydroxyl terminated copolyester polyol resin having a functionality of about 2, comprising the reaction product of: A. an aromatic component selected from phthalic anhydride; phthalic acid isomers; phthalic acid halide isomers; di-lower alkanol esters of phthalic acid isomers; digestion products of polyethylene terephthalate; or mixtures thereof; B. at least one aliphatic component selected from succinic anhydride; succinic, glutaric, or adipic acids; di-lower alkanol esters of succinic, glutaric, or adipic acids; acid halides of succinic, glutaric, or adipic acids; or mixtures thereof; and C. at least one primary hydroxyl glycol; and D. at least one secondary hydroxyl glycol; the mole ratios of the components being: (1) glycols to aromatic plus aliphatic component of from about 1.3 to 2:1; (2) aromatic component to aliphatic component of from about 0.6 to 4.0:1; (3) a secondary to primary hydroxyl glycol of from 0.05 to 0.4:1, where all mole ratios represent the final mole ratios inasmuch as glycols may be removed during processing; and (4) ethylene glycol content to aromatic component of from about 0.01 to 0.5:1.0 when a digestion product of polyethylene terephthalate is used as the aromatic component.
Claim 3
Dependent Claim
56 words
The copolyester polyol resin of claim 1 wherein the aromatic component is a digestion product of polyethylene terephthalate obtained by digesting polyethylene terephthalate in at least one diol having a boiling point higher than ethylene glycol in the presence of a transesterification catalyst and removing therefrom at least 50% of the ethylene glycol formed during digestion.
Claim 4
Dependent Claim
31 words
The copolyester polyol resin of claim 1 wherein the aliphatic component is a blend of succinic, glutaric, and adipic acids, or the di-lower alkanol esters of succinic, glutaric, and adipic acids.
Claim 5
Dependent Claim
33 words
The copolyester polyol resin of claim 1 wherein the primary hydroxyl glycol component is selected from ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, and polyethylene glycol 200, or mixtures thereof.
Claim 6
Dependent Claim
24 words
The copolyester polyol resin of claim 1 wherein the secondary hydroxyl glycol is selected from propylene glycol, dipropylene glycol, tripropylene glycol, or mixtures thereof.
Claim 7
Dependent Claim
69 words
The copolyester polyol resin of claim 1, 2, 3, 4, or 5 wherein the finished mole ratios of the components are: (a) glycols to aromatic plus aliphatic components of about 1.5 to 1.6:1; (b) aromatic component to aliphatic component of about 1.0 to 2.5:1; (c) secondary to primary hydroxyl glycol of about 0.1 to 0.4:1; and (d) ethylene glycol content to aromatic component of from about 0.06 to 0.4:1.0.
Claim 8
Dependent Claim
24 words
The copolyester polyol resin of claim 1, 2, 3, 4, or 5 wherein the hydroxyl number of the polyol is between 175 and 275.
Claim 9
Dependent Claim
23 words
The copolyester polyol resin of claim 1, 2, 3, 4, or 5 wherein the Brookfield viscosity is below 10,000 centipoise at 25° C.
Claim 10
Dependent Claim
199 words
The method of preparing a copolyester polyol resin of claim 1, 2, 3, 4, or 5 comprising digesting polyethylene terephthalate in at least one diol having a boiling point higher than ethylene glycol in the presence of a transesterification catalyst at a temperature and for a time sufficient to digest said terephthalate, removing therefrom at least 50% of the ethylene glycol formed during digestion, and admixing the remainder of said digestion product with: A. at least one aliphatic component selected from succinic anhydride; succinic, glutaric, or adipic acids; di-lower alkanol esters of succinic, glutaric, or adipic acids; acid halides of succinic, glutaric, or adipic acids; or mixtures thereof; and B. at least one primary hydroxyl glycol; and C. at least one secondary hydroxyl glycol; the mole ratios of the components being: (1) glycols to aromatic plus aliphatic component of from about 1.3 to 2:1; (2) aromatic component to aliphatic component of from about 0.6 to 4.0:1; (3) a secondary to primary hydroxyl glycol of from 0.05 to 0.4:1, where all mole ratios represent the final mole ratios inasmuch as glycols may be removed during processing; and (4) ethylene glycol content to aromatic component of from about 0.01 to 0.5:1.0.
Claim 11
Dependent Claim
79 words
A polyol blend comprising: A. from about 30 percent up to about 90 percent by weight of a hydroxyl terminated copolyester polyol resin of claim 1, 2, 3, 4, or 5; and B. from about 10 percent up to about 70 percent by weight of any materials or blends of materials which are mutually compatible with blowing agents and said polyester polyols and capable of providing sufficient urethane cross-linking functionalities or sufficient isocyanate trimerization to produce dimensionally stable foams.
Claim 12
Dependent Claim
64 words
The polyol blend of claim 10 wherein the hydroxyl terminated copolyester polyol resin comprises: (a) the aromatic component of claim 2; (b) the aliphatic component of claim 3; (c) the primary glycol of claim 4; (d) the secondary glycol of claim 5; (e) the respective mole ratios of claim 6; (f) the hydroxyl number of claim 7; and (g) the viscosity of claim 8.
Claim 13
Dependent Claim
63 words
A polyurethane modified polyisocyanurate low density foam comprising the reaction product of: (a) polymeric polymethylene polyphenylisocyanate; (b) the polyol blend of claim 10 or 11; (c) catalysts suitable for preparing a polyurethane and polyisocyanurate foam; (d) a blowing agent suitable for preparing a polyurethane modified polyisocyanurate low density foam; and, optionally, (e) a silicone surfactant suitable for controlling foam cell size and shape.
Claim 14
Dependent Claim
57 words
A polyurethane modified polyisocyanurate foam of claim 12 wherein the catalyst is a quaternary ammonium organo salt catalyst for both the -OH to -NCO reaction and the trimerization of isocyanate groups, or else a tertiary amine catalyst in combination with an alkali metal carboxylate catalyst for both reactions; and the surfactant used is a polydimethylsiloxanepolyoxyalkylene block copolymer.
Claim 15
Dependent Claim
36 words
A polyurethane modified polyisocyanurate low density foam of claim 12 or 13 wherein the density is between 0.5 and 10.0 pounds per cubic foot, and is most preferably between 1.0 and 5.0 pounds per cubic foot.
Claim 16
Dependent Claim
40 words
A digested polyethylene terephthalate consisting essentially of terephthalic core units, at least one diol having a boiling point higher than EG, and ethylene glycol, the final ethylene glycol content being less than 50% of the amount originally formed during digestion.
Claim 17
Dependent Claim
40 words
A digested polyethylene terephthalate consisting essentially of terephthalic core units, at least one diol having a boiling point higher than EG, and ethylene glycol, the final ethylene glycol content being less than 50% of the amount originally formed during digestion.
Claim 18
Dependent Claim
67 words
The method of making the digested polyethylene terephthalate of claim 15 comprising heating a polyethylene terephthalate in an excess amount of at least one diol having a boiling point higher than ethylene glycol in the presence of a transesterification catalyst at a temperature and for a time sufficient to digest the polyethylene terephthalate and then removing therefrom at least 50% of the ethylene glycol formed during digestion.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-16 | 1989-06-17 | 1989-12-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-16 | 1993-06-17 | 1993-12-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-16 | 1997-06-17 | 1997-12-17 | $7700.00 | Window Closed / Lapsed |