Method for preparing a benzophenone derivative

Patent metadata

Field	Value
Publication number	US-11976166-B2
Application number	US-201917298103-A
Country	US
Kind code	B2
Filing date	Dec 2, 2019
Priority date	Dec 17, 2018
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

The present invention is method comprising the steps of a) contacting 4-hydroxyphenone and a salt thereof with propylene oxide in a reactor heated to a temperature in the range of from 100° C. to 200° C. to form a poly(propylene oxide)-benzophenone intermediate; then b) contacting the intermediate with ethylene oxide in the heated reactor to form an alkoxylated benzophenone substituted with propylene oxide groups and ethylene oxide groups. The method of the present invention is useful for preparing a non-volatile alkoxylated benzophenone photoinitiator that gives long lasting gloss retention in an exterior architectural coating.

First claim

The invention claimed is:

1. A method comprising the steps of a) contacting in the presence of a solvent 4-hydroxyphenone and a salt thereof with propylene oxide in a reactor heated to a temperature in the range of from 100° C. to 200° C. to form a poly(propylene oxide)-benzophenone intermediate; then b) contacting the intermediate with ethylene oxide in the heated reactor to form an alkoxylated benzophenone substituted with propylene oxide groups and ethylene oxide groups, wherein the mole:mole ratio of the benzophenone to the salt thereof is in the range of from 98:2 to 80:20; the mole:mole ratio of the propylene oxide to the benzophenone is in the range of from 1:1 to 20:1; and the mole:mole ratio of the ethylene oxide to the benzophenone is in the range of from 5:1 to 50:1.

2. The method of claim 1 wherein the solvent is a polar aprotic solvent having a boiling point >100° C., wherein the reactor is a pressure rated reactor.

3. The method of claim 2 wherein mole:mole ratio of the benzophenone to the salt thereof is in the range of from 95:5 to 80:2; the mole:mole ratio of the propylene oxide to the benzophenone is in the range of from 3:1 to 10:1; and the mole:mole ratio of the ethylene oxide to the benzophenone is in the range of from 10:1 to 25:1.

4. The method of claim 3 wherein the alkoxylated benzophenone is represented by formula 1:

where x is from 2 to 13 and y is from 5 to 20 with the proviso that x+y is not greater than 25.

5. The method of claim 4 wherein y is greater than x.

Assignees

• Dow Global Technologies Llc
• Rohm & Haas

Inventors

• Belowich Matthew E
• Maurice Alvin M
• Westmeyer Mark D

Classifications

• C08G65/2696 Primary

  characterised by the process or apparatus used · CPC title

• C07C45/64 Primary

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C08G65/2612

  containing aromatic or arylaliphatic hydroxyl groups · CPC title

• C08G2650/24

  Polymeric initiators · CPC title

• C07C49/84

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title