Sterically hindered amine stabilizer

Patent metadata

Field	Value
Publication number	US-9944623-B2
Application number	US-201615233479-A
Country	US
Kind code	B2
Filing date	Aug 10, 2016
Priority date	Sep 10, 2009
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

The present invention relates to oxygen-substituted sterically hindered amines of the formulae I or II: (II), wherein, for example, F 2 , R 3 , R 5 , R 6 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 are n-butyl: Z 1 to Z 10 are propoxy and R 1 , R 4 , R 7 , R 10 , R 13 are 2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl. Compositions comprising compounds of formulae I or II and an organic material, which is susceptible to oxidative, thermal or light-induced degradation, are further disclosed. Optionally, further additives are contained.

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 is a group of formula III

 hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 12 cycloalkyl, C 5 -C 8 cycloalkenyl, C 6 -C 10 bicycloalkyl, C 3 -C 18 alkynyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl or C 7 -C 20 aralkyl substituted by C 1 -C 4 alkyl or C 6 -C 10 aryl;
R 4 is a group of formula IV

 hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 12 cycloalkyl, C 5 -C 8 cycloalkenyl, C 6 -C 10 bicycloalkyl, C 3 -C 18 alkynyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl or C 7 -C 20 aralkyl substituted by C 1 -C 4 alkyl or C 6 -C 10 aryl;
R 2 ,R 3 , R 5 and R 6 are each independently from each other C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 12 cycloalkyl, C 5 -C 8 cycloalkenyl, C 6 -C 10 bicycloalkyl, C 3 -C 18 alkynyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl or C 7 -C 20 aralkyl substituted by C 1 -C 4 alkyl or C 6 -C 10 aryl;
Z 1 , Z 2 , Z 3 , Z 4 , Z 11 and Z 12 are each independently from each other C 1 -C 18 alkyloxy, C 3 -C 18 alkenyloxy, C 3 -C 18 alkynyloxy, C 6 -C 10 aryloxy, C 7 -C 9 aralkyloxy or C 7 -C 20 aralkyloxy substituted by C 1 -C 4 alkyl or C 6 -C 10 aryl; and
X 1 is C 2 -C 12 alkylene or C 3 -C 12 alkylene substituted by hydroxyl.

2. The compound according to claim 1 , wherein
R 1 is a group of formula III, hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, C 5 -C 8 cycloalkyl, C 5 -C 7 cycloalkenyl or benzyl;
R 4 is a group of formula IV, hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, C 5 -C 8 cycloalkyl, C 5 -C 7 cycloalkenyl or benzyl;
R 2 , R 3 , R 5 and R 6 are each independently from each other C 1 -C 12 alkyl, C 3 -C 12 alkenyl, C 5 -C 8 cycloalkyl, C 5 -C 7 cycloalkenyl or benzyl;
Z 1 , Z 2 , Z 3 ,Z 4 , Z 11 and Z 12 are each independently from each other C 1 -C 12 alkyloxy, C 3 -C 12 alkenyloxy or benzyloxy; and
X 1 is C 2 -C 8 alkylene.

3. A compound according to claim 1 , wherein
R 2 , R 3 , R 5 and R 6 are each independently from each other C 1 -C 12 alkyl.

4. A compound according to claim 1 , wherein
R 1 is a group of formula III, R 4 is a group of formula IV.

5. A compound according to claim 1 , wherein
Z 1 , Z 2 , Z 3 , Z 4 , Z 11 and Z 12 are each independently from each other methyloxy, ethyloxy, propyloxy, octyloxy, undecyloxy or prop-2-enyloxy.

6. A compound according to claim 1 , wherein
R 1 and R 4 are each independently from each other hydrogen, C 1 -C 12 alkyl or C 5 -C 8 cycloalkyl.

7. A compound according to claim 1 , wherein
R 1 is a group of formula III or hydrogen;
R 4 is a group of formula IV or hydrogen;
R 2 , R 3 , R 5 and R 6 are each independently from each other C 1 -C 12 alkyl;
Z 1 , Z 2 , Z 3 , Z 4 , Z 11 and Z 12 are each independently from each other C 1 -C 12 alkyloxy, wherein in case of C 3 -C 12 alkyloxy both carbon atoms in α- and β-position next to the oxygen are not branched; and
X 1 is C 2 -C 8 alkylene.

8. A compound according to claim 1 , wherein
X 1 is hexamethylene.

9. A compound according to claim 1 of formula P-201 or P-204

10. A composition comprising
a) an Organic material which is susceptible to oxidative, thermal or light-induced degradation; and
b) at least one compound of the formula I according to claim 1 .

11. A composition according to claim 10 , wherein component b) is present in an amount of from 0.001 to 10% based on the weight of component a).

12. A composition according to claim 10 , which contains further additives.

13. A composition according to claim 12 , which contains a further additive selected from the group consisting of antioxidants, UV absorbers, hindered amine light stabilizers, nickel compounds, metal deactivators, phosphites or phosphonites, hydroxylamines, thiosynergists, nucleating agents, peroxide scavengers, fillers, reinforcing agents and terpene derivatives.

14. A method for stabilization of an organic material susceptible to oxidative, thermal or light-induced degradation, which comprises the incorporation therein or applying thereto a compound of formula I according to claim 1 .

15. A method for improving flame retardancy of an organic material, which comprises the incorporation therein or applying thereto a compound of formula I according to claim 1 .

Assignees

• Basf Se

Inventors

• Menozzi Edoardo
• Sala Massimiliano
• Bassi Anna
• Hoppe Holger
• Ludolph Björn
• Lips Gérard

Classifications

• C09K15/20

  containing nitrogen and oxygen · CPC title

• C08L101/00

  Compositions of unspecified macromolecular compounds · CPC title

• C08L23/12

  Polypropene · CPC title

• C08K5/34926

  also containing heterocyclic groups other than triazine groups · CPC title

• C08K5/3492

  Triazines · CPC title