Reaction products of terephthalic acid residues and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom

Claim 2

A polyester polyol produced by reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (a) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (b) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR23## groups on adjacent or alternate ring positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 3

The polyester polyol of claim 1 wherein the polycarboxylic acid component has aromatic ring units selected from the group consisting of units with two ##STR24## groups on adjacent ring positions, units with two ##STR25## groups on alternate ring positions, and mixtures thereof, and the terephthalic acid residue is residue (a).

Claim 4

The polyester polyol of claim 2 wherein the polycarboxylic acid component has a mixture of aromatic ring units of the formulas ##STR26## in a weight ratio of about 10:1 to 1:10.

Claim 5

The polyester polyol of claim 2 wherein the polyol component is an aliphatic dihydric alcohol having 2 to 16 carbon atoms.

Claim 6

The polyester polyol of claim 2 wherein the polyol component is a member selected from the group consisting of diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, tetraethylene glycol, tetrapropylene glycol, trimethylene glycol, tetramethylene glycol, and mixtures thereof.

Claim 7

The polyester polyol of claim 2 wherein residue (a) is a member selected from the group consisting of (i) the residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from a dimethyl terephthalate esterified oxidate reaction product, the major portion of said residue comprising a mixture of methyl and benzyl esters of benzene and biphenyl di- and tricarboxylic acids, (ii) the by-product fraction from the manufacture of dimethyl terephthalate whose major portion comprises about 15 to 70 weight percent of dimethyl terephthalate, and about 85 to 30 weight percent of a mixture of monomethyl terephthalate, bi-ring esters and polymeric materials, and (iii) mixtures thereof.

Claim 8

The polyester polyol of claim 2 wherein the polycarboxylic acid component is a member selected from the group consisting of phthalic anhydride; phthalic acid; isophthalic acid; esters of said polycarboxylic acid components; a mixture of the composition: ______________________________________ Component % By Weight ______________________________________ ##STR27## 18 ± 8 ##STR28## 50 ± 10 ##STR29## 6 ± 2 ##STR30## 6 ± 2 ##STR31## 6 ± 2 ##STR32## 5 ± 3 ##STR33## 4 ± 3 ##STR34## 2 ± 1 ##STR35## 1 ± 0.6 other aromatic compounds 2 ± 1; and ______________________________________ mixtures thereof.

Claim 9

The polyester polyol of claim 7 wherein the polyol component is diethylene glycol and the polyester polyol is characterized by a viscosity in cps at 25° C. of about 1,000 to about 25,000, a free diethylene glycol content of from about 10 to about 20 percent by weight of the polyester polyol, a hydroxyl number within a range of from about 275 to about 400, and an acid number of about 0.2 to about 10.

Claim 10

The polyester polyol of claim 2 wherein the polycarboxylic acid component is a member selected from the group consisting of phthalic anhydride; phthalic acid; isophthalic acid; esters of said polycarboxylic acid components; a mixture of the composition: ______________________________________ Component % By Weight ______________________________________ ##STR36## 18 ± 8 ##STR37## 50 ± 10 ##STR38## 6 ± 2 ##STR39## 6 ± 2 ##STR40## 6 ± 2 ##STR41## 5 ± 3 ##STR42## 4 ± 3 ##STR43## 2 ± 1 ##STR44## 1 ± 0.6 other aromatic compounds 2 ± 1; and ______________________________________ mixtures thereof.

Claim 11

The polyester polyol of claim 9 wherein the polyol component is dipropylene glycol and the polyester polyol is characterized by a viscosity in cps. at 25° C. of about 10,000 to about 25,000, a free dipropylene glycol content of from about 10 to about 20 percent by weight of the polyester polyol, a hydroxyl number within a range of from about 260 to about 400, and an acid number of about 0.2 to about 10.

Claim 12

A polyester polyol produced by a process comprising (a) reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (i) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (ii) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, and (b) subsequently reacting the reaction product of step (a) with an alkylene oxide to give a polyester polyol, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR45## groups on adjacent or alternate rig positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 13

A polyester polyol produced by a process comprising (a) reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (i) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (ii) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, and (b) subsequently reacting the reaction product of step (a) with an alkylene oxide to give a polyester polyol, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR45## groups on adjacent or alternate rig positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 14

A polyester polyol produced by a process comprising (a) reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (i) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (ii) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, and (b) distilling non-esterified polyol component from the reaction product of step (a) to give a polyester polyol having a viscosity of about 500 to 30,000 and a hydroxyl number of about 230 to 650, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR46## groups on adjacent or alternate ring positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 15

A polyester polyol produced by a process comprising (a) reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (i) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (ii) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, and (b) distilling non-esterified polyol component from the reaction product of step (a) to give a polyester polyol having a viscosity of about 500 to 30,000 and a hydroxyl number of about 230 to 650, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR46## groups on adjacent or alternate ring positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 16

A process for preparing the polyester polyol of claim 1 comprising reacting a polycarboxylic acid component-containing polyol with a terephthalic acid residue selected from the group consisting of (a) a residue remaining after dimethyl terephthalate and methyl p-toluate have been removed from the product of oxidation of p-xylene in the preparation of dimethyl terephthalate, and (b) a carboxyl functional residue resulting from the removal of terephthalic acid from the mixture obtained by the oxidation of p-xylene in the preparation of terephthalic acid, wherein the polycarboxylic acid component-containing polyol is derived from a polycarboxylic acid component and a polyol component and the polycarboxylic acid component has ring units with two ##STR47## groups on adjacent or alternate ring positions, the ring unit content of the polycarboxylic acid component being sufficient for viscosity reduction of the polyester polyol.

Claim 17

A polyisocyanurate foam comprising the reaction product of an organic polyisocyanate, a blowing agent, a trimerization catalyst, and a minor amount of a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1.

Claim 18

A process for producing a polyisocyanurate foam comprising reacting together under foam-forming conditions an organic polyisocyanate, a blowing agent, a trimerization catalyst, and a minor amount of a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1.

Claim 19

A polyurethane foam comprising the reaction product of an organic polyisocyanate, a blowing agent, a catalyst and a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1.

Claim 20

A process for producing a polyurethane foam comprising reacting together under foam-forming conditions an organic polyisocyanate, a blowing agent, a catalyst and a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1.

Claim 21

A laminate comprising at least one facing sheet adhered to the polyisocyanurate foam of claim 14.

Claim 22

A process for producing a laminate comprising (a) contacting at least one facing sheet with a polyisocyanurate foam-forming mixture comprising an organic polyisocyanate, a blowing agent, a trimerization catalyst and a minor amount of a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1, and (b) foaming said foam-forming mixture.

Claim 23

A laminate comprising at least one facing sheet adhered to the polyurethane foam of claim 16.

Claim 24

A process for producing a laminate comprising (a) contacting at least one facing sheet with a polyurethane foam-forming mixture comprising an organic polyisocyanate, a blowing agent, a catalyst and a polyol, wherein from about 5 to 100 weight percent of the polyol comprises the polyester polyol of claim 1, and (b) foaming said foam-forming mixture.