Isopropylidenediphenol-based polyether polyols, processes for their production, and foams produced therefrom

Patent metadata

Field	Value
Publication number	US-12162976-B2
Application number	US-202217670707-A
Country	US
Kind code	B2
Filing date	Feb 14, 2022
Priority date	Feb 25, 2021
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

Isopropylidenediphenol-based polyether polyols, processes for their production, foams produced using such isopropylidenediphenol-based polyether polyols, such as PUR-PIR rigid foams, as well as to processes for producing such foams. The polyether polyols have an internal block comprising polymerized ethylene oxide moieties and an external cap comprising polymerized propylene oxide moieties.

First claim

What is claimed is:

1. A polyether polyol comprising:
(a) an alkoxylate of 4,4′-isopropylidenediphenol;
(b) an alkoxylate of 2,4′-isopropylidenediphenol, 2,2′-isopropylidenediphenol, or a mixture thereof, and
(c) an alkoxylate of components comprising structural elements which are derived from phenol, acetone, isopropylidenediphenol, or a mixture of any two or more thereof, but which are not isomers of isopropylidenediphenol,
wherein the polyether polyol comprises an internal block comprising polymerized ethylene oxide moieties present in an amount of at least 50% by weight based on the total weight of polymerized alkylene oxide moieties of the internal block of the polyether polyol and an external cap comprising polymerized propylene oxide moieties present in an amount of least 50% by weight, based on the total weight of the polymerized alkylene oxide moieties of the external cap of the polyether polyol, and
wherein polymerized propylene oxide moieties of the external cap are present in an amount of at least 20% by weight, based on the total weight of polymerized alkylene oxide moieties in the polyether polyol.

2. The polyether polyol of claim 1 , wherein the polyether polyol has an arithmetically calculated functionality of 1.5 to 3.

3. The polyether polyol of claim 1 , wherein the polyether polyol has a viscosity at 25° C. of 1000 to 4900 mPas.

4. The polyether polyol of claim 1 , wherein the polyether polyol has a measured hydroxyl number of 120 to 300 mg KOH/g.

5. The polyether polyol of claim 1 , wherein:
(a) the alkoxylate of 4,4′-isopropylidenediphenol is present in an amount of at least 10% by weight, based on the total weight of the polyether polyol;
(b) the alkoxylate of 2,4′-isopropylidenediphenol, 2,2′-isopropylidenediphenol, or a mixture thereof, is present in an amount of at least 5% by weight, based on the total weight of the polyether polyol; and
(c) the alkoxylate of components comprising structural elements which are derived from phenol, acetone, isopropylidenediphenol, or a mixture of any two or more thereof, but which are not isomers of isopropylidenediphenol, is present in an amount of at least 10% by weight, based on the total weight of the polyether polyol.

6. The polyether polyol of claim 1 , wherein polymerized ethylene oxide moieties are present in an amount of least 90% by weight, based on the total weight of polymerized alkylene oxide moieties of the internal block of the polyether polyol.

7. The polyether polyol of claim 1 , wherein polymerized propylene oxide moieties are present in an amount of least 90% by weight, based on the total weight of the polymerized alkylene oxide moieties of the external cap of the polyether polyol.

8. The polyether polyol of claim 1 , wherein polymerized ethylene oxide moieties are present in an amount of at least 60% by weight, based on the total weight of alkylene oxide moieties in the polyether polyol and polymerized propylene oxide moieties are present in an amount of up to 40% by weight, based on the total weight of alkylene oxide moieties in the polyether polyol.

9. The polyether polyol of claim 1 , wherein polymerized propylene oxide moieties of the external cap are present in an amount of 30 to 40% by weight, based on the total weight of polymerized alkylene oxide moieties in the polyether polyol.

10. A method of forming a PUR-PIR rigid foam comprising reacting a polyisocyanate with the polyether polyol of claim 1 , wherein the polyisocyanate is present in an amount sufficient to provide an isocyanate index of 180 to 450, and wherein the reaction occurs in the presence of components comprising c) a blowing agent and d) a catalyst.

11. A process for preparing the polyether polyol of claim 1 , comprising:
(a) polymerizing an active hydrogen-containing initiator composition and a first portion of alkylene oxide, in the presence of a catalyst, to form an intermediate polymer having at least one hydroxyl end-group; and
(b) reacting the intermediate polymer and a second portion of alkylene oxide to form the polyether polyol,
wherein the active hydrogen-containing initiator composition comprises:
(i) 4,4′-isopropylidenediphenol,
(ii) 2,4′-isopropylidenediphenol, 2,2′-isopropylidenediphenol, or a mixture thereof, and
(iii) a component comprising structural elements which are derived from phenol, acetone, isopropylidenediphenol, or a mixture thereof, but which are not isomers of isopropylidenediphenol,
wherein the first portion of alkylene oxide comprises ethylene oxide in an amount of at least 50% by weight based on the total weight of the first portion of alkylene oxide and the second portion of alkylene oxide comprises propylene oxide in an amount of at least 50% by weight based on the total weight of the second portion of alkylene oxide, and
wherein propylene oxide is present in the second portion of alkylene oxide in an amount of at least 20% by weight, based on the total weight of alkylene oxide used in the process.

12. The process of claim 11 , wherein the polyether polyol has a arithmetically calculated functionality of 1.5 to 3, a viscosity at 25° C. of 1000 to 4900 mPas, and a measured hydroxyl number of 120 to 300 mg KOH/g.

13. The process of claim 11 , wherein the active hydrogen-containing initiator composition comprises:
(i) at least 10% by weight of 4,4′-isopropylidenediphenol, based on the total weight of the active hydrogen-containing initiator composition;
(ii) at least 5% by weight of 2,4′-isopropylidenediphenol, 2,2′-isopropylidenediphenol, or a mixture thereof, based on the total weight of the active hydrogen-containing initiator composition; and
(iii) at least 10% by weight of a compound with a chromane and/or indane base body, based on the total weight of the active hydrogen-containing initiator composition.

14. The process of claim 11 , wherein ethylene oxide is present in the first portion of alkylene oxide in an amount of at least 90% by weight, based on the total weight of the first portion of alkylene oxide and propylene oxide is present in the second portion of alkylene oxide in an amount of at least 90% by weight, based on the total weight of the second portion of alkylene oxide.

15. The process of claim 11 , wherein ethylene oxide is present in an amount of at least 60% by weight, based on the total weight of alkylene oxide used in the process and
propylene oxide is present in an amount of up to 40% by weight, based on the total weight of alkylene oxide that is used in the process.

16. The process of claim 11 , wherein propylene oxide is present in the second portion of alkylene oxide in an amount of 30 to 40% by weight, based on the total weight of alkylene oxide used in the process.

17. The polyether polyol of claim 1 , wherein polymerized ethylene oxide moieties are present in an amount of at least 95% by weight based on the total weight of polymerized alkylene oxide moieties of the internal block of the polyether polyol and polymerized propylene oxide moieties present in an amount of least 95% by weight, based on the total weight of the polymerized alkylene oxide moieties of the external cap of the polyether polyol.

18. The polyether polyol of claim 1 , wherein polymerized ethylene oxide moieties are present in an amount of 100% by weight based on the total weight of polymerized alkylene oxide moieties of the internal block of the polyether polyol and polymerized propylene oxide moieties present in an amount 100% by weight, based on the total weight of the polymerized alkylene oxide moieties of the external cap of the polyether polyol.

Assignees

• Covestro Llc

Inventors

• Lewis Sharlene A
• Loveday Anthony R
• Rexrode Eric M

Classifications

• C08G65/485

  Polyphenylene oxides · CPC title

• C08G18/4879

  containing aromatic groups · CPC title

• C08G18/4833

  Polyethers containing oxyethylene units · CPC title

• C08G2110/0025

  rigid · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title