Sulfide-containing polythiols

• US 20060025563A1
• Filed: 09/23/2005
• Published: 02/02/2006
• Est. Priority Date: 12/20/2002
• Status: Active Grant

• Current Assignee: Nina Bojkova, Robert A. Smith
• Original Assignee: Nina Bojkova, Robert A. Smith
• Inventors: Smith, Robert A., Bojkova, Nina
• Granted Patent: US 7,411,034 B2
• Time in Patent Office: Days
• US Class Current: 528/373
• CPC Class Codes: C07D 339/06 having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
• CPC Class Codes: C07D 339/08 Six-membered rings
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/3243 containing two or more aromatic rings
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/4018 Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/4837 and other oxyalkylene units
• CPC Class Codes: C08G 18/5072 containing sulfur
• CPC Class Codes: C08G 18/64 Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
• CPC Class Codes: C08G 18/664 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 75/02 Polythioethers
• CPC Class Codes: C08G 75/04 from mercapto compounds or metallic derivatives thereof C08G75/0204 takes precedence
• CPC Class Codes: C08G 75/06 from cyclic thioethers
• CPC Class Codes: C08G 75/10 from sulfur or sulfur-containing compounds and aldehydes or ketones

Abstract

The present invention relates to sulfide-containing polythiols and their methods of preparation. Sulfide-containing polythiols can have a variety of uses and applications. The sulfide-containing polythiols of the present invention can be especially useful in polyurethane compositions for the manufacture of ophthalmic lenses.

Claims

1. (canceled)

2. A method of preparing a sulfide-containing polythiol represented by the following structural formulas

3. The method of claim 2 wherein (a) is carried out in the presence of an acid catalyst.

4. The method of claim 2 wherein (b) is carried out in the presence of a base.

5. The method of claim 2 wherein at least one of the reactions of step (a) and (b) is carried out in the presence of a solvent.

6. The method of claim 2 wherein the asym-dichloroacetone is 1,1-dichloroacetone.

7. The method of claim 2, wherein the polymercaptan in (a) is chosen from materials represented by the following structural formula:

8. The method of claim 7 wherein the polymercaptan in (a) is chosen from ethanedithiol, propanedithiol and mixtures thereof.

9. The method of claim 2 wherein the polymercaptan in (b) is chosen from aromatic polymercaptans, cycloalkyl polymercaptans, heterocyclic polymercaptans, branched polymercaptans, materials represented by the following general formula:

10. The method of claim 2 wherein the polymercaptan in (a) to prepare structural formulas IV′

a and b is ethanedithiol.

11. The method of claim 2 wherein the polymercaptan in (a) to prepare structural formulas IV′

c and d is 1,3-propanedithiol.

12. The method of claim 2 wherein the polymercaptan in (b) to prepare structural formulas IV′

a and c is 1,2-ethanedithiol.

13. The method of claim 2 wherein the polymercaptoalkylsulfide in (b) is chosen from materials represented by the following general formula:

14. The method of claim 13 wherein the polymercaptoalkylsulfide in (b) to prepare structural formulas IV′

b and d is dimercaptoethylsulfide.

15. The method of claim 2 wherein in (a), the equivalent ratio of asym-dichloroacetone to polymercaptan is from 1:

1 to 1;

10.

16. The method of claim 2 wherein in (b), the equivalent ratio of reaction product of (a) to material chosen from polymercaptan, polymercaptoalkylsulfide, or a mixture thereof, can be from 1:

1.01 to 1;

2.

17. A composition comprising at least one sulfide-containing oligomeric polythiol chosen from materials represented by the following structural formulas:

18. A method of preparing a sulfide-containing oligomeric polythiol represented by the following structural formulas:

19. The method of claim 18 wherein the reaction is carried out in the presence of a base.

20. The method of claim 18 wherein the reaction is carried out in the presence of a solvent.

21. The method of claim 18 wherein the asym-dichloroacetone is 1,1-dichloroacetone.

22. The method of claim 18 wherein the polymercaptoalkylsulfide is chosen from materials represented by the following general formula:

23. The method of claim 22 wherein the polymercaptoalkylsulfide is dimercaptoethylsulfide.

24. The method of claim 18 wherein “

n”

moles of asym-dichloroacetone and “

n+1”

moles of polymercaptoalkylsulfide are present in the reaction, wherein n is an integer from 1 to 20.