# US 10,479,859 B2 · Aromatic polyester polyether polyols, polyurethanes made therefrom and building materials comprising same

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- Number: US 10,479,859 B2
- Document ID: US10479859B2
- Status: Granted
- Kind: B2
- Application number: 16/164,049
- Filed: 2018-10-18
- Published: 2019-04-25
- Granted: 2019-11-19
- Earliest claimed: 2017-10-18
- Assignees: Talaco Holdings, LLC
- Applicants: Talaco Holdings, LLC
- Inventors: Frank A. Queen; Robert Keith Salsman; Bennett McDonald Pearson
- Web page: https://patentgrep.com/patent/US10479859B2

## CPC

- C08G 63/46: Polyesters chemically modified by esterification (C08G63/20 takes precedence; by after-treatment C08G63/91)
- C08G 18/246: {containing also tin-carbon bonds}
- C08G 18/4225: {derived from residues obtained from the manufacture of dimethylterephthalate and from polyhydroxy compounds}
- C08G 18/4252: {derived from polyols containing polyether groups and polycarboxylic acids}
- C08G 18/4887: {containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 63/66: Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence)
- C08G 63/668: derived from polycarboxylic acids and polyhydroxy compounds
- C08J 9/12: by a physical blowing agent
- C08J 9/32: from compositions containing microballoons, e.g. syntactic foams
- C08L 75/08: from polyethers
- C09D 175/06: from polyesters
- C08G 18/4261: {prepared by oxyalkylation of polyesterpolyols}
- C08G 18/72: Polyisocyanates or polyisothiocyanates
- C08G 63/183: Terephthalic acids
- C08G 2110/0025: rigid
- C08G 2110/005: < 50kg/m3
- C08G 2150/60: Compositions for foaming; Foamed or intumescent coatings
- C08G 2170/60: Compositions for foaming; Foamed or intumescent adhesives
- C08G 2190/00: Compositions for sealing or packing joints
- C08J 2203/22: Expandable microspheres, e.g. Expancel®
- C08J 2375/06: from polyesters
- C08L 2201/02: Flame or fire retardant/resistant
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure. The disclosure provides aromatic polyester polyether polyols and compositions comprising such polyols. The disclosed aromatic polyester polyether polyols and compositions including same are the products of the transesterification reaction of polyethylene terephthalate (“PET”) and an ethoxylated triol, namely glycerin or trimethylolpropane, wherein the degree of ethoxylation is from 1 to 9 moles. At least some of the PET used to generate the aromatic polyester polyether polyols is derived from recycled PET. The disclosed aromatic polyester polyether polyols have utility in preparing polyurethane materials, for example.

## Claims

### Claim 1

An aromatic polyester polyether polyol having a structure that is either:
a) based on a glycerol backbone, the structure represented by a formula:
wherein each of R1, R2, and R3 is independently selected from hydroxyl and a structure represented by a formula:
provided that at least one of R1, R2, and R3 is not hydroxyl;
wherein m has a value such that the aromatic polyester polyether polyol has a Brookfield Cone and Plate Viscosity of less than about 5 Poise carried out using Spindle #4, at 100 rpm and 60° C.;
and wherein each of n1, n2, and n3 is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9, provided that a sum of the values for n1, n2, and n3 is 1 to 9;
or
b) based on a trimethylolpropane backbone, the structure represented by a formula:
wherein each of R1, R2, and R3 is independently selected from hydroxyl and a structure represented by a formula:
provided that at least one of R1, R2, and R3 is not hydroxyl;
wherein m has a value such that the aromatic polyester polyether polyol has a Brookfield Cone and Plate Viscosity of less than about 5 Poise carried out using Spindle #4 at 100 rpm and 60° C.;
and wherein each of n1, n2, and n3 is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9, provided that a sum of the values for n1, n2, and n3 is 1 to 9.

### Claim 2 (depends on 1)

The aromatic polyester polyether polyol of claim 1, consisting essentially of the structure based on the glycerol backbone.

### Claim 3 (depends on 1)

The aromatic polyester polyether polyol of claim 1, having a PET component derived from at least some recycled PET material.

### Claim 4 (depends on 1)

The aromatic polyester polyether polyol of claim 1, having a PET component derived from at least about 50% recycled material.

### Claim 5 (depends on 1)

The aromatic polyester polyether of claim 1, comprising the structure based on the glycerol backbone and having a first Brookfield Cone and Plate Viscosity of about 2.7 to about 3.2 Poise carried out using Spindle #4 at 100 rpm and 60° C. or a second Brookfield Cone and Plate Viscosity of about 3.2 to about 3.8 Poise carried out using Spindle #4 at 100 rpm and 60° C.

### Claim 6 (depends on 1)

The aromatic polyester polyether polyol of claim 1, comprising the structure based on the trimethylolpropane backbone and having a first Brookfield Cone and Plate Viscosity of about 3.7 to about 4.2 Poise carried out using Spindle #4 at 100 rpm and 60° C. or a second Brookfield Con and Plate Viscosity of about 4.0 to about 5.0 Poise carried out using Spindle #4 at 100 rpm and 60° C.

### Claim 7

An aromatic polyester polyether polyol composition derived from A transesterification of polyethylene terephthalate (PET) with an ethoxylated triol and, optionally, a catalyst, wherein the ethoxylated triol comprises a reaction product of:
a) glycerin and from 1 to 9 moles of ethylene oxide; or
b) trimethylolpropane and from 1 to 9 moles of ethylene oxide,
wherein the aromatic polyester polyether polyol has a Brookfield Cone and Plate Viscosity of less than about 5 Poise carried out using Spindle #4 at 100 rpm and 60° C.; and
wherein the Brookfield Cone and Plate Viscosity is measured at the end of the transesterification reaction, and prior to the addition of any additives or chain extenders to the aromatic polyester polyether polyol.

### Claim 8 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein the ethoxylated triol consists essentially of the reaction product of glycerin and from 1 to 9 moles of ethylene oxide.

### Claim 9 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein at least some of the PET comprises recycled PET.

### Claim 10 (depends on 9)

The aromatic polyester polyether polyol composition of claim 9, wherein at least about 50% or greater of the PET is recycled PET.

### Claim 11 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein the ethoxylated triol has a hydroxyl number of less than about 1250, as measured by ASTM 4274-16, Test A.

### Claim 12 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein a weight ratio of PET to ethoxylated triol at the start of the transesterification reaction is from about 10:90 to about 60:40.

### Claim 13 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein a weight ratio of PET to ethoxylated triol at the start of the transesterification reaction is from about 20:80 to about 50:50.

### Claim 14 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, wherein at least some of the composition comprises a material having one of a structure that is either:
a) based on a glycerol backbone, the structure represented by a formula:
wherein each of R1, R2, and R3 is independently selected from hydroxyl and a structure represented by a formula:
provided that at least one of R1, R2, and R3 is not hydroxyl;
wherein m has a value such that:
(i) the aromatic polyester polyether polyol has a first Brookfield Cone and Plate Viscosity of about 2.7 to about 3.2 Poise carried out using Spindle #4 at 100 rpm and 60° C.; or
(ii) the aromatic polyester polyether polyol has a second Brookfield Cone and Plate Viscosity of about 3.2 to about 3.8 Poise carried out using Spindle #4 at 100 rpm and 60° C.;
and wherein each of n1, n2, and n3 is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9, provided that a sum of the values for n1, n2, and n3 is 1 to 9;
or
b) based on a trimethylolpropane backbone, the structure represented by a formula:
wherein each of R1, R2, and R3 is independently selected from hydroxyl and a structure represented by a formula:
provided that at least one of R1, R2, and R3 is not hydroxyl;
wherein m has a value such that:
(i) the aromatic polyester polyether polyol has a first Brookfield Cone and Plate Viscosity of about 3.7 to about 4.2 Poise carried out using Spindle #4 at 100 rpm and 60° C.;
(ii) the aromatic polyester polyether polyol has a first Brookfield Cone and Plate Viscosity of about 4.0 to about 5.0 Poise carried out using Spindle #4 at 100 rpm and 60° C.;
and wherein each of n1, n2, and n3 is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9, provided that a sum of the values for n1, n2, and n3 is 1 to 9.

### Claim 15 (depends on 7)

The aromatic polyester polyether polyol composition of claim 7, comprising at least some ethylene glycol that is generated in the transesterification reaction.