Sulfide-containing polythiols

• US 7,411,034 B2
• Filed: 09/23/2005
• Issued: 08/12/2008
• Est. Priority Date: 12/20/2002
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Smith, Robert A., Bojkova, Nina
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US11/233,790
• Publication Number:
  US 20060025563A1
• Time in Patent Office: 1,054 Days
• Field of Search: 528/373, 528/374, 528/375
• 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

Provided are methods of preparing sulfide-containing polythiol including (a) introducing asym-dichloroacetone together with a polymercaptan to form a reaction product; and (b) introducing the reaction product of (a) with a material chosen from polymercaptoalkylsulfide, polymercaptan and mixtures thereof.

Claims

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

2. The method of claim 1 wherein (a) is carried out in the presence of an acid catalyst.

3. The method of claim 1 wherein (b) is carried out in the presence of a base.

4. The method of claim 1 wherein at least one of the reactions of step (a) and (b) is carried out in the presence of a solvent.

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

6. The method of claim 1 wherein the polymercaptan in (a) is chosen from ethanedithiol, propanedithiol and mixtures thereof.

7. The method of claim 1 wherein the polymercaptan in (a) to prepare structural formulas IV′

a and b is ethanedithiol.

8. The method of claim 1 wherein the polymercaptan in (a) to prepare structural formulas IV′

c and d is 1,3-propanedithiol.

9. The method of claim 1 wherein the polymercaptan in (b) to prepare structural formulas IV′

a and c is 1,2-ethanedithiol.

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

1 to 1;

10.

11. The method of claim 1 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.

12. A method preparing a sulfide containing polythiol comprising:

(a) introducing asym-dichloroacetone together with a polymercaptan to form a reaction product, and

(b) introducing the reaction product of (a) with a material chosen from polymercaptoalkylsulfide, polymercaptan and mixtures thereof, wherein the polymercaptan in (a) is chosen from materials represented by the following structural formula;

13. A method of preparing a sulfide-containing polythiol comprising:

(a) introducing asym-dichloroacetone together with a polymercaptan to form a reaction product, and

(b) introducing the reaction product of (a) with a material chosen from polymercaptoalkylsulfide, polymercaptan and mixtures thereof,

wherein the polymercaptan in (b) is chosen from aromatic polymercaptans, cycloalkyl polymercaptans, heterocyclic polymercaptans, branched polymercaptans, materials represented by the following general formula;

14. A method of preparing a sulfide-containing polythiol comprising:

(a) introducing asym-dichloroacetone together with a polymercaptan, and

(b) introducing the reaction product of (a) with a material chosen from polymercaptoalkylsulfide, polymercaptan and mixtures thereof,

wherein the polymercaptoalkylsulfide in (b) is chosen from materials represented by the following general formula;

15. The method of claim 14 wherein the polymercaptoalkylsulfide in (b) is dimercaptoethylsulfide.