Mixed decyl mercaptans compositions and use thereof as chain transfer agents

Patent metadata

Field	Value
Publication number	US-9631039-B1
Application number	US-201615284802-A
Country	US
Kind code	B1
Filing date	Oct 4, 2016
Priority date	Dec 28, 2015
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

A chain transfer agent composition comprises at least one branched C 10 mercaptan selected from 5-methyl-1-mercapto-nonane, 3-propyl-1-mercapto-heptane, 4-ethyl-1-mercapto-octane, 2-butyl-1-mercapto-hexane, 5-methyl-2-mercapto-nonane, 3-propyl-2-mercapto-heptane, 4-ethyl-2-mercapto-octane, 5-methyl-5-mercapto-nonane, or combinations thereof. The chain transfer agent composition can be a component of an emulsion polymerization mixture and can be used in a process for emulsion polymerization for the production of polymers, for example, via free-radical polymerization.

First claim

What is claimed is:

1. A chain transfer agent composition comprising at least one branched C 10 mercaptan selected from 5-methyl-1-mercapto-nonane, 3-propyl-1-mercapto-heptane, 4-ethyl-1-mercapto-octane, 2-butyl-1-mercapto-hexane, 5-methyl-2-mercapto-nonane, 3-propyl-2-mercapto-heptane, 4-ethyl-2-mercapto-octane, 5-methyl-5-mercapto-nonane, or combinations thereof.

2. The composition of claim 1 , wherein the at least one branched C 10 mercaptan is present in an amount of at least 30 wt. % based on a total weight of the chain transfer agent composition.

3. The composition of claim 2 , further comprising one or more of a C 12 mercaptan, a C 14 mercaptan, a C 16 mercaptan, a C 18 mercaptan, or combinations thereof.

4. The composition of claim 3 , wherein the chain transfer agent composition includes less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

5. The composition of claim 3 , wherein the at least one branched C 10 mercaptan, the C 12 mercaptan, the C 14 mercaptan, the C 16 mercaptan, and the C 18 mercaptan are present in an amount of at least 85 wt. % based on a total weight of the chain transfer agent composition.

6. The composition of claim 1 , comprising less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

7. The composition of claim 5 , comprising less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

8. The composition of claim 1 , wherein the chain transfer agent composition has an odor which is less unpleasant than an odor of mercaptan compounds which include n-dodecyl mercaptans, tert-dodecyl mercaptans, or combinations thereof present in an amount of equal to or greater than about 25 wt. % of the mercaptan compounds in an otherwise similar chain transfer agent composition.

9. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 1 .

10. The mixture of claim 9 , wherein the chain transfer agent composition is present in an amount of about 0.01 wt. % to about 5 wt. % based on a total weight of the emulsion polymerization mixture.

11. The mixture of claim 10 , wherein the at least one branched C 10 mercaptan is present in an amount of at least 30 wt. % based on a total weight of the chain transfer agent composition.

12. The mixture of claim 11 , further comprising one or more of a C 12 mercaptan, a C 14 mercaptan, a C 16 mercaptan, a C 18 mercaptan, or combinations thereof.

13. The mixture of claim 12 , wherein the chain transfer agent composition includes less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

14. The mixture of claim 12 , wherein the at least one branched C 10 mercaptan, the C 12 mercaptan, the C 14 mercaptan, the C 16 mercaptan, and the C 18 mercaptan are present in an amount of at least 85 wt. % based on a total weight of the chain transfer agent composition.

15. The mixture of claim 9 , comprising less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

16. The mixture of claim 14 , comprising less than about 10 wt. % C 16-36 sulfides based on a total weight of the chain transfer agent composition.

17. The mixture of claim 9 , wherein the chain transfer agent composition has an odor which is less unpleasant than an odor of mercaptan compounds which include n-dodecyl mercaptans, tert-dodecyl mercaptans, or combinations thereof present in an amount of equal to or greater than about 25 wt. % of the mercaptan compounds in an otherwise similar chain transfer agent composition.

18. The mixture of claim 9 , further comprising:
one or more monomers;
one or more surfactants;
one or more polymerization initiators; and
water.

19. The mixture of claim 18 , being capable of free radical polymerization.

20. The mixture of claim 18 , wherein the one or more monomers are present in the emulsion polymerization mixture in an amount ranging from about 10 wt. % to about 60 wt. % based on a total weight of the emulsion polymerization mixture;
wherein the one or more surfactants are present in the emulsion polymerization mixture in an amount ranging from about 0.05 wt. % to about 10 wt. % based on a total weight of the emulsion polymerization mixture; and
wherein the one or more polymerization initiators are present in the emulsion polymerization mixture in an amount ranging from about 0.001 wt. % to about 1 wt. % based on a total weight of the emulsion polymerization mixture.

21. A chain transfer agent composition comprising mercaptans, wherein at least about 50 wt. % of the mercaptans are 1) branched C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane (represented by Structure A), 3-propyl-1-mercapto-heptane (represented by Structure B), 4-ethyl-1-mercapto-octane (represented by Structure C), 2-butyl-1-mercapto-hexane (represented by Structure D), 5-methyl-2-mercapto-nonane (represented by Structure E), 3-propyl-2-mercapto-heptane (represented by Structure F), 4-ethyl-2-mercapto-octane (represented by Structure G), and combinations thereof; and 2) 5-methyl-5-mercapto-nonane (represented by Structure H):

22. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 21 .

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Kreider Jason L
• Matson Michael S

Classifications

• C08F12/08

  Styrene · CPC title

• C08F112/08 Primary

  Styrene · CPC title

• C07C319/00

  Preparation of thiols, sulfides, hydropolysulfides or polysulfides · CPC title

• C08F2/38 Primary

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C08F2/22

  Emulsion polymerisation · CPC title