# US 5,705,545 A · Use of HALS compounds

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- Number: US 5,705,545 A
- Document ID: US5705545A
- Status: Granted
- Kind: A
- Application number: 08/545,961
- Filed: 1995-10-20
- Granted: 1998-01-06
- Earliest claimed: 1992-08-17
- Assignees: Clariant Finance (BVI) Limited
- Inventors: Lajos Avar; Gilbert Ligner
- Web page: https://patentgrep.com/patent/US5705545A

## CPC

- C08K 5/3435: Piperidines
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D 211/58: attached in position 4
- C07D 211/94: Oxygen atom, e.g. piperidine N-oxide
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A compound of formula I for use in stabilizing polymeric material against effects such as light and heat ##STR1## in which R is hydrogen; oxygen; --OH; C.sub.1-24 alkyl; --O--CO--C.sub.1-24 alkyl; --O--CO--C.sub.1-24 alkyl; --O--CO-phenyl or --COR.sub.5 ; where R.sub.5 is --C(R.sub.3).dbd.CH.sub.2, C.sub.1-6 alkyl, phenyl, CO--C.sub.1-24 alkyl, --CO--phenyl, --NR.sub.7 R.sub.8, --CH.sub.2 --C.sub.6 H.sub.5, --CO--OC.sub.1-12 alkyl or --COOH; where R.sub.3 is hydrogen or C.sub.1-4 alkyl; R.sub.7 is hydrogen, C.sub.1-12 alkyl, C.sub.5-6 cycloalkyl, phenyl, phenyl-C.sub.1-4 alkyl or C.sub.1-12 alkylphenyl and R.sub.8 is C.sub.1-12 alkyl or hydrogen, each R.sub.1, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.1 form a group --(CH.sub.2).sub.5 --; and each R.sub.2, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.2 form a group --(CH.sub.2).sub.5 --. A is --O-- or --N(C.sub.1-4 alkyl)-- or --NH-- R.sub.9 is hydrogen or methyl, and R.sub.10 is an aromatic single ring or an aromatic fused 2 to 3 ring group or a heteroaromatic single ring or a a heteroaromatic fused 2 or 3 ring group.

## Claims

### Claim 1

A composition comprising a thermoplastic material and a compound of formula I ##STR18## in which R is CH.sub.3 ;
each R.sub.1, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.1 form a group --(CH.sub.2).sub.5 --;
each R.sub.2, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.2 form a group --(CH.sub.2).sub.5 --;
R.sub.9 is hydrogen or methyl;
R.sub.10 is methoxyphenyl; and
A is --O--, --N(C.sub.1-4 alkyl)--, or --NH--.

### Claim 2 (depends on 1)

A composition according to claim 1 in which R.sub.10 is 4-methoxyphenyl.

### Claim 3 (depends on 2)

A composition according to claim 2 wherein
each R.sub.1 and R.sub.2 is methyl;
R.sub.9 is H; and
A is --O--.

### Claim 4 (depends on 1)

A composition according to claim 1 in which 0.01-5% of the compound of formula I are present based on the weight of thermoplastic material.

### Claim 5 (depends on 1)

A process for reacting a 2,2,6,6-tetraalkyl-piperidinyl compound with a polymeric material comprising the process step of: reacting a compound of formula I according to claim 1 with a polymeric material having one or more unsaturated monomers capable of reacting with a compound of formula I.

### Claim 6 (depends on 5)

A process of claim 5 further comprising catalyzing said reaction by exposure to light.

### Claim 7 (depends on 1)

A process for grafting 2,2,6,6-tetraalkyl-piperidinyl compound into a polymeric material comprising the process step of: grafting a compound of formula 1 according to claim 1 into a polymeric material having one or more unsaturated monomers capable of reacting with a compound of formula 1.

### Claim 8 (depends on 7)

A process of claim 7 further comprising catalyzing said reaction by exposure to light.

### Claim 9

A compound of formula I ##STR19## in which R is CH.sub.3 ;
each R.sub.1, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.1 form a group --(CH.sub.2).sub.5 --;
each R.sub.2, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.2 form a group --(CH.sub.2).sub.5 --;
R.sub.9 is hydrogen or methyl;
R.sub.10 is methoxyphenyl; and
A is --O--, --N(C.sub.1-4 alkyl)--, or --NH--.

### Claim 10 (depends on 9)

A compound according to claim 9 in which R.sub.10 is 4-methoxyphenyl.

### Claim 11 (depends on 10)

A compound according to claim 10 wherein
each R.sub.1 and R.sub.2 is methyl;
R.sub.9 is H; and A is --O--.

### Claim 12

A process for preparing a compound of formula I ##STR20## in which R is hydrogen, oxygen, --OH, C.sub.1-24 alkyl, --O--C.sub.1-24 alkyl, --O--CO--C.sub.1-24, --O--CO-phenyl, or --COR.sub.5 ;
each R.sub.1, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl), or both groups R.sub.1 form a group --(CH.sub.2).sub.5 ;
each R.sub.2, independently, is --CH.sub.3 or --CH.sub.2 (C.sub.1-4 alkyl) or both groups R.sub.2 form a group --(CH.sub.2).sub.5 --;
R.sub.3 is hydrogen or C.sub.1-4 alkyl;
R.sub.5 is --C(R.sub.3).dbd.CH.sub.2, C.sub.1-6 alkyl, phenyl, CO--C.sub.1-24 alkyl, --CO-phenyl, --NR.sub.7 R.sub.8, --CH.sub.2 --C.sub.6 H.sub.5, --CO--OC.sub.1-12 alkyl, or --COOH;
R.sub.7 is hydrogen, C.sub.1-12 alkyl, C.sub.5-6 cycloalkyl, phenyl, phenyl-C.sub.1-4 alkyl, or C.sub.1-12 alkylphenyl;
R.sub.8 is C.sub.1-12 alkyl, or hydrogen;
R.sub.9 is hydrogen or methyl;
R.sub.10 is an aromatic single ring, an aromatic fused 2 or 3 ring group, or a group of the formula ##STR21## A is --O--, --N(C.sub.1-4 alkyl)--, or --NH-- comprising the process step of:
condensing one of mole of a compound or a derivative thereof of the formula II
R.sub.10 --CH.dbd.C.dbd.(COOH).sub.2 II
with 2 moles of a compound of formula III ##STR22##

### Claim 13 (depends on 12)

A process of claim 12 wherein said condensing is at temperatures of 80.degree.-200.degree. C.

### Claim 14 (depends on 1)

A polymeric material containing a 2,2,6,6-tetraalkylpiperidinyl group derived from a compound of formula I according to claim 1 that has been reacted with or grafted with a polymeric material having one or more unsaturated monomers capable of reacting with a compound of formula I.

### Claim 15 (depends on 1)

A composition of claim 1 wherein R.sub.9 is methyl.

### Claim 16 (depends on 1)

A composition of claim 1 wherein A is --N(C.sub.1-4 alkyl)-- or --NH--.

### Claim 17 (depends on 9)

A compound of claim 9 wherein R.sub.9 is methyl.

### Claim 18 (depends on 9)

A compound of claim 9 wherein A is --N(C.sub.1-4 alkyl)-- or --NH--.

### Claim 19 (depends on 12)

A process of claim 12 wherein R.sub.10 is methoxy.

### Claim 20 (depends on 19)

A process of claim 19 wherein each R.sub.1 and R.sub.2 is methyl, R.sub.9 is H, and A is --O--.

### Claim 21 (depends on 12)

A process of claim 12 wherein R.sub.9 is methyl and A is --N(C.sub.1-4 alkyl)-- or --NH--.