Quinone compounds for inhibiting monomer polymerization

Patent metadata

Field	Value
Publication number	US-9611336-B2
Application number	US-201213660488-A
Country	US
Kind code	B2
Filing date	Oct 25, 2012
Priority date	Oct 25, 2012
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

The polymerization of monomers may be at least partially reduced or inhibited by introducing an effective amount of an additive. The additive may be or include a first compound:

where:

R1 and R2 may be or include an alkyl group, an aryl group, an alkyl group having a heteroatom, an aryl group having a heteroatom, and combinations thereof. The hetero atom may be or include sulfur, nitrogen and/or oxygen. R1 may be the same or different from R2. The polymerizable monomers may be or include, but are not limited to styrene, butadiene, isoprene, acrylic acid, acrylonitrile, vinyl acetate, and combinations thereof.

First claim

What is claimed is:

1. A method for inhibiting the polymerization of monomers comprising:
introducing to the monomers an effective amount of an additive to reduce the rate of polymerization, and
heating the additive and the monomers;

wherein the additive consists of a polymerization retarder selected from the group consisting of 3,5-di-tert-butyl-1,2-benzoquinone (3,5 BQ); 3,5-di-methyl-1,2-benzoquinone; 3,6-di-tert-butyl-1,2-benzoquinone; 2,6-di-tert-butyl-1,4-benzoquinone (2,6 BQ); 2,5-di-tert-butyl-1,4-benzoquinone (2,5 BQ); 4-sec-butyl-2,6-di-tert-butylphenol; and combinations thereof, and a polymerization inhibitor selected from the group consisting of a nitroxide, a hydroxylamine, phenylene diamine, and compound (1), or combinations thereof;
wherein compound (1) is:

and
wherein R3 is selected from the group consisting of an alkyl group, an aryl group, an alkyl group having a heteroatom, and an aryl group having a heteroatom; wherein the heteroatom is selected from the group consisting of sulfur, nitrogen, and oxygen;

and wherein the monomers are selected from the group consisting of styrene, butadiene, isoprene, acrylic acid, acrylonitrile, vinyl acetate, and combinations thereof; wherein the effective amount of the additive ranges from about 0.01 ppm to about 10,000 ppm.

2. The method of claim 1 , wherein the polymerization retarder consists of a first compound selected from a group consisting of 3,5-di-tert-butyl-1,2-benzoquinone (3,5 BQ); 3,5-di-methyl-1,2-benzoquinone; and 3,6-di-tert-butyl-1,2-benzoquinone; or combinations thereof, and a second compound selected from the group consisting of 2,6-di-tert-butyl-1,4-benzoquinone (2,6 BQ); 2,5-di-tert-butyl-1,4-benzoquinone (2,5 BQ); and 4-sec-butyl-2,6-di-tert-butylphenol; or combinations thereof.

3. The method of claim 2 , wherein the ratio between the first compound and the second compound is based on weight and ranges from about 1:1 to about 1:5.

4. The method of claim 1 , wherein the ratio between the polymerization retarder and the polymerization inhibitor is based on weight and ranges from about a 1:1 ratio to about a 1:10 ratio.

5. A method for inhibiting the polymerization of monomers comprising:
introducing to the monomers an effective amount of an additive to reduce the rate of polymerization; and
heating the additive and the monomers;

wherein the monomers are selected from the group consisting of styrene, butadiene, isoprene, acrylic acid, acrylonitrile, and vinyl acetate, or combinations thereof; wherein the additive consist of:
a first polymerization retarder selected from the group consisting of 3,5-di-tert-butyl-1,2-benzoquinone (3,5 BQ); and 4-sec-butyl-2,6-di-tert-butylphenol; or combinations thereof;
a second polymerization retarder different from the first polymerization retarder; wherein the second polymerization retarder is selected from the group consisting of 2,6-di-tert-butyl-1,4-benzoquinone (2,6 BQ); 3,5-di-methyl-1,2-benzoquinone, and 3,6-di-tert-butyl-1,2-benzoquinone, 2,5-di-tert-butyl-1,4-benzoquinone (2,5 BQ); or combinations thereof; and a polymerization inhibitor selected from the group consisting of a nitroxide, a hydroxylamine, phenylene diamine, and compound (1), or combinations thereof;
wherein compound (1) is:

and
wherein R3 is selected from the group consisting of an alkyl group, an aryl group, an alkyl group having a heteroatom, and an aryl group having a heteroatom, wherein the heteroatom is selected from the group consisting of sulfur, nitrogen, and oxygen;

wherein the effective amount of the additive ranges from about 0.01 ppm to about 10,000 ppm and wherein the ratio between the first polymerization retarder and the second polymerization retarder is based on weight and ranges from about 1:1 to about 1:5.

6. The method of claim 5 , wherein the first and second polymerization retarder are 3,5 BQ and 2,5 BQ, respectively; and wherein the ratio between the 3,5 BQ and the 2,5 BQ is based on weight and ranges from about a 1:1 ratio to about a 1:5 ratio.

7. The method of claim 1 , wherein the polymerization inhibitor is selected from the group consisting of a nitroxide, phenylene diamine, and compound (1), or combinations thereof; wherein compound (1) is:

and
wherein R3 is selected from the group consisting of an alkyl group, an aryl group, an alkyl group having a heteroatom, and an aryl group having a heteroatom, wherein the heteroatom is selected from the group consisting of sulfur, nitrogen, and oxygen.

8. The method of claim 5 , wherein the polymerization inhibitor is selected from the group consisting of a nitroxide, phenylene diamine, and compound (1), or combinations thereof; wherein compound (1) is:

and
wherein R3 is selected from the group consisting of an alkyl group, an aryl group, an alkyl group having a heteroatom, and an aryl group having a heteroatom, wherein the heteroatom is selected from the group consisting of sulfur, nitrogen, and oxygen.

Assignees

• Baker Hughes Inc

Inventors

• Mo Hua
• Metzler Roger D

Classifications

• C08F2/38 Primary

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

• C07C7/20 Primary

  Use of additives, e.g. for stabilisation · CPC title

• C09K15/08

  containing a phenol or quinone moiety · CPC title

• C08F2/40 Primary

  using retarding agents · CPC title