Process for the production of (trimethylsilyloxy)silylalkylglycerol methacrylates

• US 20060047134A1
• Filed: 08/25/2004
• Published: 03/02/2006
• Est. Priority Date: 08/25/2004
• Status: Abandoned Application

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Ward, Robert S., Wang, Shanger, Tian, Yuan, Mahadevan, Shivkumar, Molock, Frank, Parakka, James Paul
• Application Number:
  US10/926,425
• Publication Number:
  US 20060047134A1
• Time in Patent Office: Days
• US Class Current: 556/446
• CPC Class Codes: C07F 7/0879 Hydrosilylation reactions

Abstract

The present invention relates to a process comprising the steps of reacting in the presence of a hydrosilylation catalyst, a first reaction mixture comprising a free radical reactive compound and a silicon containing compound to form a silicon substituted glyceryl (meth)acrylate.

Claims

1. A process comprising the step of reacting, in the presence of a hydrosilylation catalyst, a first reaction mixture comprising at least one free radical reactive compound and a silicon containing compound of the formula

HSiR²R³R⁴

wherein R², R³ and R⁴ are independently selected from alkyl groups having 1 to 12 carbons, substituted and unsubstituted benzene and toluene groups, and —

OSiR⁵R⁶R⁷ wherein R⁵, R⁶ and R⁷ are independently selected from the group consisting of straight or branched alkyl groups having 1 to 12 carbon atoms and substituted or unsubstituted phenyl or benzyl rings to form a silicon substituted glyceryl (meth)acrylate.

2. The process of claim 1 wherein said hydrosilylation catalyst is selected from group consisting of platinum, platinum supported on a solid carrier, chloroplatinic acid, complexes of chloroplatinic acid with alcohols, aldehydes and ketones, platinum-olefin complexes;

platinum-vinyl siloxane complexes;

platinum-phosphine complexes;

platinum-phosphite complexes, dicarbonyl dichloroplatinum, platinum-hydrocarbon complexes, platinum-alcoholate catalysts and combinations thereof.

3. The process of claim 1 wherein said hydrosilation catalyst is selected from group consisting of RhCl(PPh₃)₃, RhCl₃, Rh/Al₂O₃, RuCl₃, IrCl₃, FeCl₃, AlCl₃, PdCl₂≅

2H₂O, NiCl₂ and TiCl₄ and combinations thereof.

4. The process of claim 1 wherein said hydrosilylation catalyst is selected from group consisting of chlorides of platinum, vinyl complexes of platinum and combinations thereof.

5. The process of claim 1 wherein said hydrosilylation catalyst comprises chloroplatinic acid.

6. The process of claim 1 wherein at least two of R², R³ and R⁴ are the same and are selected from alkyl groups having 1 to 12 carbon atoms.

7. The process of claim 1 wherein at least two of R², R³ and R⁴ are the same and are —

OSiR⁵R⁶R⁷.

8. The process of claim 1 wherein R², R³ and R⁴ are selected from straight or branched alkyl groups having 1 to 8 carbon atoms.

9. The process of claim 1 wherein R², R³ and R⁴ are selected from straight or branched alkyl groups having 1 to 4 carbon atoms.

10. The process of claim 1 wherein at least two of R², R³ and R⁴ are the same and are selected from straight or branched alkyl groups having 1 to 8 carbon atoms.

11. The process of claim 1 wherein at least two of R², R³ and R⁴ are the same and are selected from straight or branched alkyl groups having 1 to 4 carbon atoms.

12. The process of claim 7 wherein at least two of R⁵, R⁶ and R⁷ are the same and are selected from straight or branched alkyl groups having 1 to 8 carbon atoms.

13. The process of claim 7 wherein at least two of R⁵, R⁶ and R⁷ are the same and are selected from straight or branched alkyl groups having 1 to 4 carbon atoms

14. The process of claim 1 wherein said temperature is between about −

20°

C. and about 100°

C.

15. The process of claim 1 wherein said temperature is between about −

10°

C. and about 60°

C.

16. The process of claim 1 wherein said process is conducted for a reaction time between about 1 and about 24 hours.

17. The process of claim 1 wherein said process is conducted for a reaction time between about 4 and about 12 hours.

18. The process of claim 1 wherein said at least one free radical reactive compound is of the formula

wherein R^N is selected from moieties having the formulae II and III:

B is selected from the group consisting of hydrogen bonding groups and carboxylic acid derivatives;

L is a linking group selected from the group consisting of a direct bond, hetero atoms and straight or branched alkylenes having 1 to 6 carbon atoms.

19. The process of claim 18 wherein B is selected from the group consisting of carbonyl, alkylene having 1 to 6 carbon atoms which may be unsubstituted or substituted with hydroxy, amines, amides, ethers, esters, aldehydes, ketones, aromatics, alkyl groups and combinations thereof.

20. The process of claim 18 wherein L is a hetero atom selected from O, N or S;

B is a hydroxyl substituted alkyl group having 1-4 carbon atoms and R¹ may be the same or different, and is independently selected from H and alkyl groups having 1 to 4 carbon atoms.

21. The process of claim 1 wherein said free radical reactive compound is

22. The process of claim 1 wherein said process further comprises the step of treating said first reaction product to remove compounds which are more polar than said silicon substituted glyceryl (meth)acrylate.

23. The process of claim 1 wherein said temperature is between about −

10°

C. and about 30°

C.