Compositions for control and inhibition of polymerization of vinyl aromatic monomers, and methods of use thereof

• US 10,450,246 B2
• Filed: 02/09/2017
• Issued: 10/22/2019
• Est. Priority Date: 02/13/2016
• Status: Active Grant

• Current Assignee: Dorf Ketal Chemicals India Private Limited
• Original Assignee: Dorf Ketal Chemicals India Private Limited
• Inventors: Subramaniyam, Mahesh
• Primary Examiner(s): Dang, Thuan D
• Application Number:
  US15/774,466
• Publication Number:
  US 20190248718A1
• Time in Patent Office: 985 Days
• Field of Search: 25218229, 585435, 585436, 585440, 585441
• CPC Class Codes: C07C 15/46 Styrene; Ring-alkylated styrenes
• CPC Class Codes: C07C 7/20 Use of additives, e.g. for stabilisation
• CPC Class Codes: C08F 12/08 Styrene
• CPC Class Codes: C08F 2/38 Polymerisation using regulators, e.g. chain terminating agents , e.g. telomerisation
• CPC Class Codes: C08F 2/40 using retarding agents

Abstract

The present invention relates to an improved amine based additive composition for control and inhibition of polymerization of aromatic vinyl monomers, particularly of styrene comprising one or more quinone methide compounds, one or more phenolic compounds and further comprising at least one aliphatic tertiary amine containing —OH group in the alkyl chain. In one embodiment, the present invention also relates to method of use of presently provided composition. In another embodiment, the present invention also relates to method of controlling and inhibiting polymerization of aromatic vinyl monomers, particularly of styrene by employing presently provided composition. In still another embodiment, the present invention also relates to method of preparation of presently provided composition.

Claims

1. An improved amine based additive composition for controlling and inhibiting polymerization of aromatic vinyl monomers including styrene comprising:

(A) one or more quinone methide or derivatives thereof (QM),

(B) one or more phenolic compounds, and

characterized in that the said composition further comprises;

(C) at least one amine comprising aliphatic tertiary amine containing —

OH group in the alkyl chain;

wherein the quinone methide or derivatives thereof (QM) comprises benzyl quinone methide;

wherein the phenolic compound comprises 2,6-di-tert-butyl phenol (2,6 DTBP), butylated hydroxy anisole (BHA), butylated hydroxy toluene (BHT), or a mixture thereof; and

wherein the aliphatic tertiary amine comprises tri-isopropanol amine or tris(2-hydroxypropyl)amine (TIPA), N,N,N′

,N′

-Tetrakis (2-hydroxyethyl) ethylene-diamine (THEED), N,N,N′

,N′

-Tetrakis (2-hydroxypropyl) ethylene-diamine, or mixture thereof.

2. The improved amine base additive composition as claimed in claim 1, wherein the quinone methide or derivatives thereof (QM) comprises 4-benzylidene, 2,6-di-tert-butyl cyclohexa-2,5-dienone.

3. A method of using the additive composition as claimed in claim 1 to control and inhibit polymerization of aromatic vinyl monomers including styrene, wherein the method comprises treating the aromatic vinyl monomers including styrene with the said additive composition.

4. The method as claimed in claim 3, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 0.01 ppm to 5000 ppm by weight of the stream of the monomers including styrene.

5. The method as claimed in claim 3, wherein the additive composition is used at a temperature varying from 50 degree C. to 180 degree C.

6. The method as claimed in claim 3, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 0.1 ppm to 3000 ppm by weight of the stream of the monomers including styrene.

7. The method as claimed in claim 3, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 1 ppm to 2000 ppm by weight of the stream of the monomers including styrene.

8. The method as claimed in claim 3, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 5 ppm to 2000 ppm by weight of the stream of the monomers including styrene.

9. The method as claimed in claim 3, wherein the additive composition is used at a temperature varying from 60 degree C. to 180 degree C.

10. A method for controlling and inhibiting polymerization of aromatic vinyl monomers including styrene, wherein the method comprises adding the said additive composition as claimed in claim 1 to the stream comprising aromatic vinyl monomers including styrene.

11. The method as claimed in claim 10, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 0.01 ppm to 5000 ppm by weight of the stream of the monomers including styrene.

12. The method as claimed in claim 10, wherein the additive composition is used at a temperature varying from 50 degree C. to 180 degree C.

13. The method as claimed in claim 10, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 0.1 ppm to 3000 ppm by weight of the stream of the monomers including styrene.

14. The method as claimed in claim 10, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 1 ppm to 2000 ppm by weight of the stream of the monomers including styrene.

15. The method as claimed in claim 10, wherein the additive composition is added to the stream containing aromatic vinyl monomers including styrene in an amount varying from 5 ppm to 2000 ppm by weight of the stream of the monomers including styrene.

16. The method as claimed in claim 10, wherein the additive composition is used at a temperature varying from 60 degree C. to 180 degree C.

17. A method of using the additive composition as claimed in claim 2 to control and inhibit polymerization of aromatic vinyl monomers including styrene, wherein the method comprises treating the aromatic vinyl monomers including styrene with the said additive composition.

18. A method for controlling and inhibiting polymerization of aromatic vinyl monomers including styrene, wherein the method comprises adding the said additive composition as claimed in claim 2 to the stream comprising aromatic vinyl monomers including styrene.