# US 5,710,240 A · Condensates of butyne-linked hindered amines

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- Number: US 5,710,240 A
- Document ID: US5710240A
- Status: Granted
- Kind: A
- Application number: 08/606,897
- Filed: 1996-02-26
- Granted: 1998-01-20
- Earliest claimed: 1995-03-02
- Assignees: Ciba Specialty Chemicals Corporation
- Inventors: Alfred Steinmann
- Web page: https://patentgrep.com/patent/US5710240A

## CPC

- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D 211/58: attached in position 4
- C08G 18/679: {Acetylenic compounds}
- C08G 63/6856: {Dicarboxylic acids and dihydroxy compounds}
- C08G 64/12: containing nitrogen
- C08G 77/54: Nitrogen-containing linkages
- C08K 5/3435: Piperidines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The invention relates to compounds of the formula I ##STR1## in which n is a number in the range from 1 to 100; X is --R.sup.7 --, --CO--, --CO--CO--, --CO--R.sup.2 --CO--, --CO--NH--R.sup.5 --NH--CO--, --CO--O--R.sup.6 --O--CO-- or ##STR2## where p is a number in the range from 0 to 6, X' is O or a direct bond, E is C.sub.1 -C.sub.12 alkyl, phenyl, C.sub.7 -C.sub.12 phenylalkyl or C.sub.5 -C.sub.12 cycloalkyl, and E' is hydrogen or is as defined for E; Z, when X is R.sup.7, is O or NR.sup.1 ; Z, when X is ##STR3## is O; and Z, in all other cases, is O, NH or NR.sup.1 ; R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.8 alkanoyl, benzoyl or C.sub.1 -C.sub.4 alkyl-substituted benzoyl; R.sup.2 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; C.sub.2 -C.sub.18 alkylene which is interrupted by O or S; phenylene; a mixed aromatic/aliphatic radical containing 7 to 12 carbon atoms; naphthylene; or an --R.sup.4 --D--R.sup.4 -- radical; R.sup.4 is 1,4-cyclohexylene or 1,4-phenylene; and R.sup.6 is phenylene, naphthylene or ##STR4## R.sup.5, when Z is O, is as defined for R.sup.6 ; and R.sup.5, when Z is NH or NR.sup.1, is as defined for R.sup.6 ; and D is C.sub.1 -C.sub.3 alkylene, --S--, --SO--, --SO.sub.2 --, --CO--, --O--, --NH-- or --NR.sup.1 --. Compounds of the formula I can advantageously be used for stabilizing organic material against the harmful effects of light, oxygen and/or heat.

## Claims

### Claim 1

A compound of the formula Ia ##STR32## in which n is a number in the range from 4 to 80; X is --R.sup.7, --CO--, --CO--CO--, --CO--R.sup.2 --CO--, --CO--NH--R.sup.5 --NH--CO--, --CO--O--R.sup.6 --O--CO-- or ##STR33## where p is a number in the range from 0 to 6, X' is O or a direct bond, E is C.sub.1 -C.sub.12 alkyl, phenyl, C.sub.7 -C.sub.12 phenyl alkyl or C.sub.5 -C.sub.12 cycloalkyl, and E' is hydrogen or is as defined for E;
Z, when X is R.sup.7, is O or NR.sup.1 ;
Z, when X is ##STR34## is O; and Z, in all other cases, is O, NH or NR.sup.1 ;
R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.8 alkanoyl, benzoyl or C.sub.1 -C.sub.4 alkyl-substituted benzoyl;
R.sup.2 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; C.sub.2 -C.sub.18 alkylene which is interrupted by O or S; phenylene; a mixed aromatic/aliphatic radical containing 7 to 12 carbon atoms; naphthylene; or an --R.sup.4 --D--R.sup.4 -- radical;
R.sup.4 is 1,4-cyclohexylene or 1,4-phenylene; and
R.sup.6 is phenylene, naphthylene or ##STR35## R.sup.5, when Z is O, is as defined for R.sup.2 ; and R.sup.5, when Z is NH or NR.sup.1, is as defined for R.sup.6 ; and
D is C.sub.1 -C.sub.3 alkylene, --S--, --SO.sup.2, --CO--, --O--, --NH-- or NR.sup.1 --;
A is hydrogen or a terminal group of the formula --X--Z';
B is a terminal group of the formula ##STR36## or --Z'; and Z' is OH, NH.sup.2 or OR.sup.1.

### Claim 2 (depends on 1)

A compound of the formula Ia according to claim 1, in which X is --CO--, --CO--CO--, --CO--R.sup.2 --CO--, ##STR37## or --CO--NH--R.sup.5 --NH--CO--, where p is 0 or 1, X' is O or a direct bond, E' is hydrogen, phenyl or methyl, and E is phenyl or methyl;
R.sup.1 is C.sub.1 -C.sub.8 alkyl, benzyl, C.sub.2 -C.sub.8 alkanoyl, benzoyl or cyclohexyl;
R.sup.2 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; C.sub.2 -C.sub.18 alkylene which is interrupted by O or S; phenylene; a mixed aromatic/aliphatic radical containing 7 to 12 carbon atoms; naphthylene; or an --R.sup.4 --D--R.sup.4 -- radical;
R.sup.4 is 1,4-cyclohexylene or 1,4-phenylene;
R.sup.5, when Z is O, is C.sub.3 -C.sub.12 alkylene, phenylene, naphthylene, cyclohexylene, tolylene, ethylene which is interrupted by phenylene, or --R.sup.4 --CH.sub.2 --R.sup.4 --; and
D is C.sub.1 -C.sub.3 alkylene, --NH--, --NR.sup.1, --CO-- or --S--.

### Claim 3 (depends on 1)

A compound of the formula Ia according to claim 1, in which
Z is O or NR.sup.1 ;
X is --CO--CO--, --CO--R.sup.2 --CO--, ##STR38## or --CO--NH--R.sup.5 --NH--CO--; R.sup.2 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; phenylene, CH.sub.2 --S--CH.sub.2, CH.sub.2 --O--CH.sub.2 or ##STR39## and R.sup.5, when Z is O, is C.sub.3 -C.sub.12 alkylene, phenylene, naphthylene, cyclohexylene, tolylene, ethylene which is interrupted by phenylene, or --R.sup.4 --CH.sub.2 --R.sup.4 --, where R.sup.4 is 1,4-cyclohexylene or 1,4-phenylene; and R.sup.5, when Z is NR.sup.1, is phenylene.

### Claim 4 (depends on 3)

A compound of the formula Ia according to claim 3, in which n is an integer in the range from 5 to 50;
Z is an oxygen atom;
R.sup.2 and R.sup.7 are C.sub.1 -C.sub.7 alkylene or phenylene; and
R.sup.5 is C.sub.3 -C.sub.12 alkylene, phenylene, naphthylene or cyclohexylene.

### Claim 5 (depends on 1)

A composition comprising A) an organic material which is sensitive to oxidative, thermal and/or actinic degradation, and B) a sufficient stabilizing amount of a compound of the formula Ia according to claim 1.

### Claim 6 (depends on 5)

A composition according to claim 5, wherein component A is a synthetic organic polymer.

### Claim 7 (depends on 5)

A composition according to claim 5, comprising from 0.01 to 10% by weight of the compound of component B, based on the material to be stabilized.

### Claim 8 (depends on 5)

A composition according to claim 5, wherein the additional component C is selected from the group consisting of further stabilizers, fillers, reinforcing agents, pigments, dyes, plasticizers, solvents, lubricants, flow-control agents, fluorescent brighteners, nucleating agents, antistatic agents and fire-retarding agents.

### Claim 9 (depends on 1)

A process for stabilizing organic material against thermal, oxidative and/or actinic degradation, which comprises adding a compound of the formula Ia according to claim 1 to this material.

### Claim 10

A compound produced by polycondensation or polyaddition of a compound of the formula II ##STR40## with a bifunctional reaction partner selected from dicarboxylic acids, dichlorides and diesters of dicarboxylic acids of the formula G--CO--R.sup.2 --CO--G or G--CO--CO--G, in which G is hydrogen, Cl or C.sub.1 -C.sub.4 alkoxy; or an anhydride of the formula ##STR41## diisocyanates of the formula OCN--R.sup.5 --NCO; dihalogen compounds of the formula Hal--R.sup.7 --Hal, in which Hal is in each case a halogen atom; phosgene; C.sub.1 -C.sub.4 alkyl carbonic acid diesters; or bischloroformates of the Cl--CO--O--R.sup.6 --O--CO--Cl type, in which R.sup.2, R.sup.5 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; C.sub.2 -C.sub.18 alkylene which is interrupted by O or S; phenylene; a mixed aromatic/aliphatic radical containing 7 to 12 carbon atoms; naphthalene; or an --R.sup.4 --D--R.sup.4 -- radical;
R.sup.4 is 1,4-cyclohexylene or 1,4-phenylene;
R.sup.6 is phenylene, naphthalene or ##STR42## and D is C.sub.1 -C.sub.3 alkylene, --S--, --SO--, --SO.sub.2 --, --CO--, --O--, --NH-- or --NR.sup.1.