Method for producing methacrylated benzophenones

Patent metadata

Field	Value
Publication number	US-9656941-B2
Application number	US-201415026861-A
Country	US
Kind code	B2
Filing date	Sep 29, 2014
Priority date	Oct 4, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

The invention relates to a process for preparing methacrylic esters of hydroxyl-functional benzophenones and to their use. Methacrylated benzophenones (benzophenone (meth)acrylates) can be prepared in high purity by the process of the invention, in a simple way and in a high yield.

First claim

The invention claimed is:

1. A process for preparing a benzophenone (meth)acrylate, comprising:
reacting a hydroxybenzophenone and a (meth)acrylic anhydride in the presence of a catalytic amount of a salt;
wherein the molar ratio of (meth)acrylic anhydride to hydroxybenzophenone is in the range from 1.0:1.0 to 1.6:1.0; and
wherein the salt is present in an amount of 0.2 to 5.0 mol % relative to the amount of (meth)acrylic anhydride.

2. The process according to claim 1 , wherein the molar ratio is in the range from 1.05:1.0 to 1.5:1.0.

3. The process according to claim 1 , wherein the hydroxybenzophenone is 4-hydroxybenzophenone.

4. The process according to claim 1 , wherein the (meth)acrylic anhydride is methacrylic anhydride or acrylic anhydride.

5. The process according to claim 1 , wherein the salt is sodium methacrylate.

6. The process according to claim 1 , wherein the salt is present in an amount of 0.2 to 0.7 mol % relative to the amount of (meth)acrylic anhydride.

7. The process according to claim 1 , wherein the reacting, takes place at a temperature in the range from 50 to 120° C.

8. The process according to claim 1 , wherein the reacting takes place over 1 to 13 h.

9. The process according to claim 1 , wherein the benzophenone (meth)acrylate is precipitated in water.

10. The process according to claim 1 , wherein the benzophenone (meth)acrylate is employed as a monomer, a comonomer, or both in a polymerization process.

11. The process according to claim 1 , wherein the benzophenone (meth)acrylate is employed as a photocrosslinker of a polymer.

12. The process according to claim 1 , wherein the benzophenone (meth)acrylate is employed as a polymeric photoinitiator.

13. The process according to claim 1 , further comprising at least one selected from the group consisting of
quenching by contacting with water to precipitate the benzophenone (meth)acrylate, and
esterifying unreacted (meth)acrylic anhydride by the addition of methanol.

14. A process for preparing a benzophenone (meth)acrylate, comprising:
reacting a hydroxybenzophenone and a (meth)acrylic anhydride in the presence of a catalytic amount of a salt;
wherein the molar ratio of (meth)acrylic anhydride to hydroxybenzophenone is 1.0:1.0 to 1.6:1.0; and
wherein the salt is selected from the group consisting of sodium acetate, lithium acetate, potassium acetate, lithium (meth)acrylate, sodium eth acrylate, potassium (meth)acrylate and mixtures thereof.

15. The process according to claim 14 , wherein the salt is sodium methacrylate.

16. The process according to claim 14 , wherein the salt is present in an amount of 0.2 to 5.0 mol % relative to the amount of (meth)acrylic anhydride.

17. The process according to claim 14 , wherein the molar ratio of (meth)acrylic anhydride to hydroxybenzophenone is 1,0:1,0 to 1.2:1.0.

18. The process according to claim 15 , wherein the sodium (meth)acrylate is generated in situ from sodium methoxide.

19. A process for preparing a benzophenone (meth)acrylate, comprising:
reacting a hydroxybenzophenone and a (meth)acrylic anhydride in the presence of a catalytic amount of a salt selected from the group consisting of sodium acetate, lithium acetate, potassium acetate, lithium (meth)acrylate, sodium (meth)acrylate. potassium (meth)acrylate and mixtures thereof; and
quenching by contacting with water to precipitate the benzophenone (meth)acrylate.

20. The process according to claim 19 , further comprising:
esterifying unreacted (meth)acrylic anhydride by the addition of methanol prior to the quenching.

Assignees

• Klesse Wolfgang
• Knebel Joachim
• Saal Doris
• Evonik Roehm Gmbh

Inventors

• Klesse Wolfgang
• Knebel Joachim
• Saal Doris

Classifications

• B01J31/12

  containing organo-metallic compounds or metal hydrides · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/62

  Use of additives, e.g. for stabilisation · CPC title

• C07C69/017

  Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title

• B01J31/0209

  Esters of carboxylic or carbonic acids · CPC title