Polymeric phenolic antioxidants

Patent metadata

Field	Value
Publication number	US-11987552-B2
Application number	US-201916523523-A
Country	US
Kind code	B2
Filing date	Jul 26, 2019
Priority date	Jul 27, 2018
Publication date	May 21, 2024
Grant date	May 21, 2024

Abstract

A phenol compound comprises a phenyl group, a hydroxy group directly bonded to the phenyl group, and at least one polymeric substituent bound to the phenyl group. The polymeric substituent comprises three or more monomers units. A method for producing a polyurethane polymer comprises the steps of (a) providing a polyol; (b) providing a polyisocyanate compound; (c) providing the phenol compound described above; (d) combining the polyol, the polyisocyanate compound, and the phenol compound to produce a reaction mixture; and (e) allowing the polyol and the polyisocyanate compound to react to produce a polyurethane polymer.

First claim

What is claimed is:

1. A phenol compound comprising a phenyl group, a hydroxy group directly bonded to the phenyl group, two steric hindering groups directly bonded to the phenyl group in positions that are ortho to the hydroxy group, and at least one polymeric substituent bound to the phenyl group, the polymeric substituent comprising three or more monomer units, wherein the polymeric substituent is directly bonded to a linking group, the linking group is directly bonded to a carbon atom of the phenyl group, and the linking group is an oxygen atom, and wherein the polymeric substituent terminates in a hydroxy group.

2. The phenol compound of claim 1 , wherein the steric hindering groups are selected from the group consisting of hydroxy groups, alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, alkoxy groups, substituted alkoxy groups, aryloxy groups, and substituted aryloxy groups.

3. The phenol compound of claim 2 , wherein the steric hindering groups are selected from the group consisting of hydroxy groups, alkyl groups, and substituted alkyl groups.

4. The phenol compound of claim 1 , wherein each of the monomer units is independently selected from the group consisting of alkyleneoxy groups, oxoalkyleneoxy groups, oxoalkyleneamine groups, alkyleneamine groups, substituted alkylene groups, saccharide groups, halomethylalkyleneoxy groups, and quaternaryammoniummethylalkyleneoxy groups.

5. The phenol compound of claim 4 , wherein the monomer units are selected from the group consisting of alkyleneoxy groups and oxoalkyleneoxy groups.

6. The phenol compound of claim 5 , wherein the monomer units are selected from the group consisting of ethyleneoxy, propyleneoxy, and butyleneoxy.

7. The phenol compound of claim 1 , wherein the hydroxy group and the polymeric substituent are disposed in the para position relative to each other on the phenyl group.

8. A method for producing a polyurethane polymer, the method comprising the steps of:
(a) providing a polyol;
(b) providing a polyisocyanate compound;
(c) providing a phenol compound comprising a phenyl group, a hydroxy group directly bonded to the phenyl group, and at least one polymeric substituent bound to the phenyl group, the polymeric substituent comprising three or more monomer units, wherein the polymeric substituent is directly bonded to a linking group, the linking group is directly bonded to a carbon atom of the phenyl group, and the linking group is an oxygen atom;
(d) combining the polyol, the polyisocyanate compound, and the phenol compound to produce a reaction mixture; and
(e) allowing the polyol and the polyisocyanate compound to react to produce a polyurethane polymer.

9. The method of claim 8 , wherein the phenol compound further comprises one or more steric hindering groups directly bonded to the phenyl group, wherein the steric hindering group is bonded to the phenyl group in a position that is ortho to the hydroxy group.

10. The method of claim 9 , wherein the phenol compound comprises two steric hindering groups directly bonded to the phenyl group.

11. The method of claim 9 , wherein the steric hindering groups are selected from the group consisting of hydroxy groups, alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, alkoxy groups, substituted alkoxy groups, aryloxy groups, and substituted aryloxy groups.

12. The method of claim 11 , wherein the steric hindering groups are selected from the group consisting of hydroxy groups, alkyl groups, and substituted alkyl groups.

13. The method of claim 8 , wherein each of the monomer units is independently selected from the group consisting of alkyleneoxy groups, oxoalkyleneoxy groups, oxoalkyleneamine groups, alkyleneamine groups, substituted alkylene groups, saccharide groups, halomethylalkyleneoxy groups, and quaternaryammoniummethylalkyleneoxy groups.

14. The method of claim 13 , wherein the monomer units are selected from the group consisting of alkyleneoxy groups and oxoalkyleneoxy groups.

15. The method of claim 14 , wherein the monomer units are selected from the group consisting of ethyleneoxy, propyleneoxy, and butyleneoxy.

16. The method of claim 8 , wherein the polymeric substituent terminates in a hydroxy group.

17. The method of claim 8 , wherein the hydroxy group and the linking group are disposed in the para position relative to each other on the phenyl group.

Assignees

• Milliken & Co

Inventors

• Moon Nicholas G
• Qin Haihu
• Free Sharon A
• Ragsdale Mark E
• Hong Michael

Classifications

• C07C69/675 Primary

  of saturated hydroxy-carboxylic acids · CPC title

• C08G18/165

  covered by C08G18/18 and C08G18/24 · CPC title

• C08G18/244

  tin salts of carboxylic acids · CPC title

• C08G18/284 Primary

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G18/3203

  Polyhydroxy compounds · CPC title