Mixed decyl mercaptans compositions and use thereof as chain transfer agents

Patent metadata

Field	Value
Publication number	US-10000590-B2
Application number	US-201715842305-A
Country	US
Kind code	B2
Filing date	Dec 14, 2017
Priority date	Dec 28, 2015
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

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 sulfides, wherein at least about 50wt. % of the sulfides are branched C 20 sulfides represented by the structure R 1 —S—R 2 , wherein R 1 and R 2 are each independently a functional group derived from an olefin, wherein the olefin comprises 5-methyl-1-nonene (represented by Structure I), 3-propyl-1-heptene (represented by Structure J), 4-ethyl-1-octene (represented by Structure K), 2-butyl-1-hexene (represented by Structure L), or combinations thereof

2. The composition of claim 1 , wherein the olefin comprises a) at least 76mol % C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol % 2-butyl-1-hexene (represented by Structure L), ii) at least 8 mol % 3-propyl-1-heptene (represented by Structure J), iii) at least 6 mol % 4-ethyl-1-octene (represented by Structure K), and iv) at least 20 mol % 5-methyl-1-nonene (represented by Structure I); and b) at least 1 mol % C 14 monoolefins.

3. The composition of claim 2 , wherein the C 10 monoolefins comprise from 1mol % to 16 mol % 4-decene and/or 5 -decene.

4. The composition of claim 2 , wherein the C 10 monoolefins comprise from 0.5mol % to 9 mol % 1-decene.

5. The composition of claim 1 , wherein the olefin further comprises from 0.1mol % to 5 mol % C 12 monoolefins, the C 12 monoolefins comprising from 54 mol % to 74 mol % 1-dodecene.

6. The composition of claim 1 , wherein the olefin further comprises from 0.1mol % to 5 mol % C 8 monoolefins, the C 8 monoolefins comprising at least 95 mol % 1-octene.

7. A chain transfer agent composition comprising:
(A) at least about 25 wt. % 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-heptaue (represented by Structure F), 4-ethyl-2-mercapto-octane (represented by Structure G), 5-methyl-5-mercapto-nonane (represented by Structure H), and combinations thereof;

and
(B) at least about 5 wt. % C 20 sulfides represented by the structure R 1 —S—R 2 , wherein R 1 and R 2 are each independently a functional group derived from an olefin, wherein the olefin comprises 5-methyl-1-nonene (represented by Structure I), 3-propyl-1-heptene (represented by Structure J), 4-ethyl-1-octene (represented by Structure K), 2-butyl-1-hexene (represented by Structure L), or combinations thereof

8. A chain transfer agent composition comprising:
(A) from at least about 50 wt. % to about 90 wt. % mercaptans, wherein at least about 50 wt. % of the mercaptans are 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), 5-methyl-5-mercapto-nonane (represented by Structure H), and combinations thereof;

and
(B) from at least about 10 wt. % to about 30 wt. % sulfides, wherein at least 50wt. % of the sulfides are branched C 20 sulfides represented by the structure R 1 —S—R 2 , wherein R R and R 2 are each independently a functional group derived from an olefin selected from the group consisting of 5-methyl-1-nonene (represented by Structure I), 3-propyl-1-heptene (represented by Structure J), 4-ethyl-1-octene (represented by Structure K), 2-butyl-1-hexene (represented by Structure L), and combinations thereof

9. A chain transfer agent composition comprising:
(A) at least about 25 wt. % C 10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane (represented by Structure A), 3-propyl-1mercapto-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), 5-methyl-5-mercapto-nonane (represented by Structure H), and combinations thereof;

(B) at least about 5 wt. % C 20 sulfides represented by the structure R 1 —S—R 2 , wherein R 1 and R 2 are each independently a functional group derived from an olefin, wherein the olefin comprises 5-methyl-1-nonene (represented by Structure I), 3-propyl-1-heptene (represented by Structure J), 4ethyl-1-octene (represented by Structure K), 2-butyl-1-hexene (represented by Structure L), or combinations thereof;

and
one or more of the following components (C)-(I):
(C) less than about 5 wt. % C 8 mercaptans;
(D) less than about 15 wt. % C 12 mercaptans;
(E) less than about 15 wt. % C 14 mercaptans;
(F) less than about 5 wt. % C 16 mercaptans and/or C 18 mercaptans;
(G) less than about 1 wt. % C 16-36 sulfides represented by the structure R 3 —S—R 4 , wherein R 3 and R 4 are each independently a functional group derived from an olefin selected from the group consisting of C 8 monoolefins, C 10 monoolefins, C 12 monoolefins, C 14 monoolefins, C 16 monoolefins, and C 18 monoolefins, wherein R 3 and R 4 are not both branched C 10 monoolefins;
(H) less than about 10 wt. % unreacted C 8-18 monoolefins; and
(I) less than about 10 wt. % non-olefin impurities selected from the group consisting of C 8-14 alkanes, cyclohexane, methylcyelopentane, methylcyclohexane, benzene, toluene, ethylbenzene, xylene, mesitylene, hexamethylbenzene, C 4-12 alcohols, 2-ethyl-4-hexanol, and 2-ethylhexyl-2-ethylhexanoate.

10. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 1 ; one or more monomers; one or more surfactants; one or more polymerization initiators; and water.

11. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 7 ; one or more monomers; one or more surfactants; one or more polymerization initiators; and water.

12. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 8 ; one or more monomers; one or more surfactants; one or more polymerization initiators; and water.

13. An emulsion polymerization reaction mixture comprising the chain transfer agent composition of claim 9 ; one or more monomers; one or more surfactants; one or more polymerization initiators; and water.

14. The composition of claim 1 , wherein the chain transfer agent composition has an odor which is less unpleasant than an odor of mercaptan compo

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Kreider Jason L
• Matson Michael S

Classifications

• C08F12/08

  Styrene · CPC title

• C07C321/04 Primary

  of an acyclic saturated carbon skeleton · CPC title

• C07C319/00

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

• C08F112/08 Primary

  Styrene · CPC title

• C08F2/38 Primary

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