Compositions and methods for inhibiting vinyl aromatic monomer polymerization

• US 20040034247A1
• Filed: 08/16/2002
• Published: 02/19/2004
• Est. Priority Date: 08/16/2002
• Status: Abandoned Application

• Current Assignee: GE Betz, Inc. (General Electric Company)
• Original Assignee: GE Betz, Inc. (General Electric Company)
• Inventors: Eldin, Sherif
• Application Number:
  US10/222,033
• Publication Number:
  US 20040034247A1
• Time in Patent Office: Days
• US Class Current: 560/4
• CPC Class Codes: C07B 63/04 Use of additives anti-oxidant compositions or compositions inhibiting chemical change in general C09K15/00
• CPC Class Codes: C07C 15/46 Styrene; Ring-alkylated styrenes
• CPC Class Codes: C07C 39/08 Dihydroxy benzenes; Alkylated derivatives thereof
• CPC Class Codes: C07C 49/657 containing six-membered aromatic rings
• CPC Class Codes: C07C 49/747 containing six-membered aromatic rings
• CPC Class Codes: C07C 7/20 Use of additives, e.g. for stabilisation

Abstract

A synergistic composition and method of use are disclosed. The compositions comprise a quinone methide derivative, a hydroxylamine compound and a catechol compound. These compositions demonstrate synergism at inhibiting the polymerization of a vinyl aromatic monomer. Preferably the quinone methide derivative is 2,6-di-tert-butyl-4-benzylidene-cyclo-2,5-dienone, the hydroxylamine compound is N,N-bis(hydroxypropyl)hydroxylamine, and the catechol is 4-tert-butyl catechol.

Claims

1. A method for inhibiting the polymerization of vinyl aromatic monomers comprising adding to said monomer an effective polymerization inhibiting amount of a composition comprising (A) a quinone methide derivative having the formula

2. The method as recited in claim 1, wherein said quinone methide derivative is 4-benzylidene-2,6-di-tert-butyl-cyclohexa-2,5-dienone or 2,6-di-tert-butyl4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone.

3. The method as recited in claim 1, wherein said hydroxylamine compound is a hydroxyalkylhydroxylamine.

4. The method as recited in claim 3, wherein said hydroxylamine compound is N,N-bis(hydroxypropyl) hydroxylamine.

5. The method as recited in claim 1 wherein said vinyl aromatic monomer is selected from the group consisting of styrene, bromostyrene, divinylbenzene and α

-methylstyrene.

6. The method as recited in claim 1, wherein the temperature of polymerization of said vinyl aromatic monomer ranges from about 80°

to about 150°

C.

7. The method as recited in claim 1, wherein said composition is added to said monomer in an amount ranging from about 1 to about 50,000 parts per million parts of said monomer.

8. The method as recited in claim 1, wherein said catechol is selected from the group consisting of 4-tert-butyl catechol, 3-methoxycatechol and 3,5-di-tert-butylcatechol.

9. The method as recited in claim 1, wherein (A) is 2,6-di-tert-butyl-4-benzylidine-cyclo-2,5-dienone and (B) is N,N-bis(hydroxypropyl)hydroxylamine.

10. A composition comprising (A) a quinone methide derivative having the formula:

11. The composition as recited in claim 10, wherein said quinone methide derivative is 4-benzylidene-2,6-di-tert-butyl-cyclohexa-2,5-dienone or 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone.

12. The composition as recited in claim 10, wherein said hydroxylamine compound is a hydroxyalkyl hydroxylamine.

14. The composition as recited in claim 10, wherein said catechol is selected from the group consisting of 4-tert-butyl catechol, 3-methoxycatechol and 3,5-di-tert-butylcatechol.

15. The composition as recited in claim 10, wherein (A) is 2,6-di-tert-butyl-4-benzylidene-cyclo-2,5-dienone and (B) is N,N-bis(hydroxypropyl) hydroxylamine.

16. The composition as recited in claim 10, wherein there is synergism among (A):

(B) and (C) as a vinyl aromatic monomer polymerization inhibitor.

17. The composition as recited in claim 10, further comprising styrene.

18. The composition as recited in claim 10, wherein (A) is 2,6-di-tert-butyl-4-benzylidene-cyclo-2,5-dienone, (B) is N,N-bis(hydroxypropyl) hydroxylamine and (C) is 4-tert-butyl catechol.

13. The composition as recited in 12, wherein said hydroxylamine compound is N,N-bis(hydroxypropyl) hydroxylamine.