PROCESS FOR THE PRODUCTION OF (TRIMETHYLSILYLOXY)SILYLALKYLGLYCEROL METHACRYLATES

• US 20070265460A1
• Filed: 07/25/2007
• Published: 11/15/2007
• 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: Wang, Shanger, Tian, Yuan, Mahadevan, Shivkumar, Molock, Frank, Parakka, James, Ward, Robert
• Application Number:
  US11/782,727
• Publication Number:
  US 20070265460A1
• Time in Patent Office: Days
• US Class Current: 556/467
• 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, and at a temperature between about −

10°

C. and about 30°

C., 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 first reaction product comprising at least one silicone monomer.

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{tilde over (═

)}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

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 formula 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.

14-15. -15. (canceled)

21. (canceled)

22. (canceled)

23. (canceled)