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Claims for Patent: 4,906,775

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Claims for Patent: 4,906,775

Title: Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl (alkane) carboxylic acids with oxyethylates of polythiols
Abstract:Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl (alkane) carboxylic acids with oxyethylates of polythiols are useful as stabilizers for polymers, especially for polyethylene and polypropylene.
Inventor(s): Kupper; Friedrich-Wilhelm (Marl, DE), Voges; Heinz-Werner (Dorsten, DE), Haage; Hans-Jurgen (Herne, DE)
Assignee: Huels Aktiengesellschaft (Marl, DE)
Application Number:07/122,724
Patent Claims: 1. An ester of a 3-tert-butyl or 3-tert-butyl-5-alkyl-4-hydroxyphenyl-(alkane) carboxylic acid of formula I ##STR25## with an oxethylate of a polythiol aromatic of formulae II or III having 2 to 6 thiol groups ##STR26## or with an oxethylate of a dithiolcycloalkane of formula IV, which contains a maximum of 6 alkylene oxide units, ##STR27## wherein X is (CH.sub.2).sub.m SH

X' is (CH.sub.2).sub.r SH

X" is (CH.sub.2).sub.s SH, wherein m, r and s represents 0 or 1,

R, R', R" being identical or different are each H, alkyl, halogen or hydroxyl,

R.sub.3 is H, C.sub.1 to C.sub.4 alkyl,

R.sub.4, R.sub.5 being identical or different are each C.sub.2 to C.sub.4 alkylene,

q=0 to 7, ##STR28## n=2 to 6, inclusive, for z or z'=0, n=1 to 5, inclusive, for z or z'.noteq.0,

o+p=n

O.ltoreq.a, z.ltoreq.a+z.ltoreq.6-n (in formula II)

O.ltoreq.b, c, z'.ltoreq.4.ltoreq.8-n (in formula III).

2. An ester according to claim 1, of 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid of formula Ia ##STR29##

3. An ester according to claim 1, with an oxethylate of a polythiol aromatic of formula II having 2 to 6 thiol groups.

4. An ester according to claim 2, with an oxethylate of polythiol aromatic of formula II having 2 to 6 thiol groups.

5. An ester according to claim 1, with an oxethylate of the polythiol aromatic of formulae II or III, containing one ethylene oxide unit per thiol group as 2-hydroxyethyl thiol groups.

6. An ester according to claim 2, with an oxethylate of the polythiol aromatic of formulae II or III, containing one ethylene oxide unit per thiol group as 2-hydroxyethyl thio groups.

7. An ester according to claim 4, with an oxethylate of the polythiol aromatic of formulae II or III, containing one ethylene oxide unit per thiol group as 2-hydroxyethyl thio groups.

8. An ester according to claim 1, with a bis(monooxethylate) of 1,4 or 1,2-bis-(thiomethyl) benzene or 1,4-bis-(thiomethyl)-2,3,5,6-tetrabromobenzene or with tris-(monooxethylate) of 1,3,5-tris-(thiomethyl)2,4,6-trichlorobenzene or with tetra-(monooxethylates) of 1,4-dichloro-2,3,5,6-tetra-(thiomethyl) benzene or 1,4-dibromo-2,3,5,6-tetra-(thiomethyl) benzene or with penta-(monooxethylate) of penta-(thiomethyl) toluene or with hexa-(monooxethylate) of hexakis-(2-hydroxyethylthiomethyl) benzene or with bis-(monooxethylate) of 2,9-paramenthane dithiol).

9. An ester according to claim 2, with a bis(monooxethylate) of 1,4 or 1,2-bis-(thiomethyl) benzene or 1,4-bis-(thiomethyl)-2,3,5,6-tetrabromobenzene or with tris-(monooxethylate) of 1,3,5-tris-(thiomethyl)2,4,6-trichlorobenzene or with tetra-(monooxethylates) of 1,4-dichloro-2,3,5,6-tetra-(thiomethyl) benzene or 1,4-dibromo-2,3,5,6-tetra-(thiomethyl) benzene or with penta-(monooxethylate) of penta-(thiomethyl) toluene or with hexa-(monooxethylate) of hexakis-(2-hydroxyethylthiomethyl) benzene or with bis-(monooxethylate) of 2,9 - paramenthane dithiol).

10. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 1.

11. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 2.

12. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 3.

13. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 5.

14. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 8.

15. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 9.

16. A stabilized polyolefin according to claim 10, wherein the polyolefin is polyethylene or polypropylene.

17. A stabilized polyolefin according to claim 13, wherein the polyolefin is polyethylene or polypropylene.

18. A stabilized polyolefin comprising a stabilizing amount of an ester according to claim 15.

19. A process of stabilizing a polyolefin by incorporating a stabilizer in said polymer, the improvement wherein the stabilizer is an ester of claim 1.

20. A process according to claim 19, wherein the polymer is polyethylene or polypropylene.

21. A process of stabilizing a polyolefin by incorporating a stabilizer in said polymer, the improvement wherein the stabilizer is as ester of claim 8.

22. A process of stabilizing a polyolefin by incorporating a stabilizer in said polymer, the improvement wherein the stabilizer is an ester of claim 9.

23. An ester according to claim 1, being tris-(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid ester of 1,3,5-tris-(2'hydroxyethylthiomethyl)-2,4,6,-trichlorobenzene.

24. An ester according to claim 1, with a 1,4-bis-(2'hydroxyethythiomethyl)benzene; 1,2,-bis-2'hydroxyethylthiomethyl)benzene; 1,4-bis-(2'hydroxyethylthiomethyl) 2,3,5,6-tetrabromobenzene; 1,3,5-tris-(2'hydroxyethyl-thiomethyl)-2,4,6-trichlorobenzene; 1,2,4,5-tetra-(2'-hydroxyethyl-thiomethyl)3,6-dichlorobenzene; 1,2,4,5-tetra-(2-hydroxyethyl-thiomethy)-3,6-dibromobenzene; penta-(2'-hydroxyethylthiomethyl) methyl benzene; hexa-(2-hydroxyethylthiomethyl) benzene; bis-2,9-(2'-hydroxyethylthio)para-menthane; or 1,4-dihydroxy-2,3,5,6-tetra-(2'hydroxyethyl-thio) benzene.
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