Polyester polyol comprising an imide moiety and methods of manufacture thereof

Patent metadata

Field	Value
Publication number	US-12486362-B2
Application number	US-202017631707-A
Country	US
Kind code	B2
Filing date	Aug 5, 2020
Priority date	Aug 9, 2019
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

A method of forming an aromatic polyester polyol compound comprising an imide moiety, wherein the method comprises reacting: (i) a cyclic anhydride compound; (ii) a phthalic acid based compound; (iii) a primary amine compound; and (iv) an aliphatic diol compound.

First claim

What is claimed is:

1 . A method for forming an aromatic polyester polyol compound comprising an imide moiety, wherein the method comprises reacting a reactive mixture comprising:
(i) a cyclic anhydride compound comprising Structure (1), Structure (2), or combinations thereof;

wherein X is a cyclic anhydride moiety, OH, or COOH, which attached directly to the structure or through R which is an aromatic ring, aliphatic ring, aliphatic chain radical each containing from 1 through 12 carbon atoms with or without alkyl branches, and with or without hetero atoms comprising, O, N, S etc. and n is an integer from 0 through 1;
wherein Component (i) is present in an amount of 3% to 20% by weight based on a total weight of the reactive mixture;

(ii) a phthalic acid based compound, wherein Component (ii) is present in an amount of 2% to 40% by weight based on the total weight of the reactive mixture,
(iii) a primary amine compound comprising Structure (3);
NH 2 —R—X  Structure (3)

wherein X is —NH2, —OH or —COOH, and R is an aromatic ring, aliphatic ring, aliphatic chain radical each containing from 1 through 12 carbon atoms with or without alkyl branches, and with or without hetero atoms comprising, O, N, S, or combinations thereof;
wherein Component (iii) is present in an amount of 1% to 15% by weight based on the total weight of the reactive mixture;

(iv) an aliphatic diol compound, wherein Component (iv) is present in an amount of 40% to 70% by weight based on the total weight of the reactive mixture;
(v) optionally, a high functionality, low molecular weight polyether polyol compound;
(vi) optionally, a hydrophobic compound; and
wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25° C. and comprises a hydroxy value ranging from about 30 to about 600.

2 . The method according to claim 1 , wherein the viscosity of the aromatic polyester polyol compound ranges from about 200 to about 150,000 centipoises at 25° C.

3 . The method according to claim 1 , wherein the acid value of the aromatic polyester polyol compound ranges from about 0.1 mg of KOH/g to about 10 mg of KOH/g.

4 . The method according to claim 1 , wherein the method comprises reacting Components (i), (ii), (iii), and (iv) in a single pot synthesis process.

5 . The method according to claim 1 , wherein the reaction does not occur in the presence of a solvent.

6 . The method according to claim 1 , wherein the aromatic polyester polyol compound has a better thermal stability than a non-imide moiety containing aromatic polyester polyol compound having similar aromatic content, hydroxy number, functionality, and acid value.

7 . An aromatic polyester polyol compound comprising an imide moiety, wherein the aromatic polyester polyol is the reaction product of a reactive mixture comprising:
(i) a cyclic anhydride compound comprising Structure (1), Structure (2), or combinations thereof;

wherein X is a cyclic anhydride moiety, OH, or COOH, which attached directly to the structure or through R which is an aromatic ring, aliphatic ring, aliphatic chain radical each containing from 1 through 12 carbon atoms with or without alkyl branches, and with or without hetero atoms comprising, O, N, S etc. and n is an integer from 0 through 1;
wherein Component (i) is present in an amount of 3% to 20% by weight based on a total weight of the reactive mixture;

(ii) a phthalic acid based compound, wherein Component (ii) is present in an amount of 2% to 40% by weight based on the total weight of the reactive mixture,
(iii) a primary amine compound comprising Structure (3);
NH 2 —R—X  Structure (3)

wherein X is —NH2, —OH or —COOH, and R is an aromatic ring, aliphatic ring, aliphatic chain radical each containing from 1 through 12 carbon atoms with or without alkyl branches, and with or without hetero atoms comprising, O, N, S, or combinations thereof;
wherein Component (iii) is present in an amount of 1% to 15% by weight based on the total weight of the reactive mixture;

(iv) an aliphatic diol compound, wherein Component (iv) is present in an amount of 40% to 70% by weight based on the total weight of the reactive mixture;
(v) optionally, a high functionality, low molecular weight polyether polyol compound;
(vi) optionally, a hydrophobic compound; and
wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25° C. and comprises a hydroxy value ranging from about 30 to about 600.

8 . The aromatic polyester polyol compound according to claim 7 , wherein the viscosity of the aromatic polyester polyol compound ranges from about 200 to about 150,000 centipoises at 25° C.

9 . The aromatic polyester polyol compound according to claim 7 , wherein the acid value of the aromatic polyester polyol compound ranges from about 0.1 mg of KOH/g to about 10 mg of KOH/g.

10 . The aromatic polyester polyol compound according to claim 7 , wherein the method comprises reacting Components (i), (ii), (iii), and (iv) in a single pot synthesis process.

11 . The aromatic polyester polyol compound according to claim 7 , wherein the reaction does not occur in the presence of a solvent.

12 . The aromatic polyester polyol compound according claim 7 , wherein the aromatic polyester polyol compound has a better thermal stability than a non-imide moiety containing aromatic polyester polyol compound having similar aromatic content, hydroxy number, functionality, and acid value.

13 . The method according to claim 1 , wherein Component (v) is present in the reaction mixture.

14 . The method according to claim 1 , wherein Component (vi) is present in the reaction mixture.

15 . The method according to claim 1 , wherein Component (v) and Component (vi) are present in the reaction mixture.

Assignees

• Huntsman Int Llc

Inventors

• Xi Kai
• Shieh David J
• Wu Lifeng
• Singh Sachchida

Classifications

• C08G2110/00

  Foam properties · CPC title

• C08G73/16 Primary

  Polyester-imides · CPC title

• C08G18/4208 Primary

  containing aromatic groups · CPC title