# US 5,705,083 A · Stabilizing leather against thermal and photochemical decomposition

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- Number: US 5,705,083 A
- Document ID: US5705083A
- Status: Granted
- Kind: A
- Application number: 08/662,735
- Filed: 1996-06-10
- Granted: 1998-01-06
- Earliest claimed: 1994-01-19
- Assignees: Ciba Specialty Chemicals Corporation
- Inventors: Franz Wyss; Vladimir Arnold; Helena Dbaly; Gisbert Leuschner; Manfred Rembold; Alois Puntener
- Web page: https://patentgrep.com/patent/US5705083A

## CPC

- C08K 5/34926: {also containing heterocyclic groups other than triazine groups}
- C08K 5/3435: Piperidines
- C14C 9/00: Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
- D06N 3/0059: {Organic ingredients with special effects, e.g. oil- or water-repellent, antimicrobial, flame-resistant, magnetic, bactericidal, odour-influencing agents; perfumes (D06N3/0065 takes precedence)}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C14C: CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING (bleaching of leather or furs D06L; dyeing of leather or furs D06P)
- D06N: WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR

## Abstract

Water-emulsifiable or -dispersible physical forms of sterically hindered mines, UV absorbers and antioxidants and their use for thermal and photochemical stabilization of materials of plastics, textile coatings, imitation leather and leather are described. The physical forms comprise a) a sterically hindered amine, b) a UV absorber and/or c) an antioxidant and d) if appropriate, water and other additives.

## Claims

### Claim 1

A composition for improving the resistance of leather and imitation leather to the influence of light and/or heat, which comprises a) an amount, which is effective to improve the resistance of said leather and imitation leather to the influence of light and/or heat of at least one of a water-insoluble sterically hindered amine, a water insoluble UV absorber or a water-insoluble antioxidant,
b) a polyalcohol which is completely or partly esterified with a fatty acid,
c) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, an alkylene oxide and, optionally,
d) water and/or a stabilizer, diluent, fat-liquoring agent, agent which influences handle, acrylic resin, polyurethane, flame-proofing agent, emulsion carrier and/or hydrophobizing agent, with the proviso that components b) and c) are present in an amount which is effective to emulsify component a).

### Claim 2 (depends on 1)

A composition according to claim 1, which comprises a water-insoluble sterically hindered amine.

### Claim 3 (depends on 1)

A composition according to claim 1, which comprises a water-insoluble UV absorber.

### Claim 4 (depends on 1)

A composition according to claim 1, which comprises a water-insoluble antioxidant.

### Claim 5 (depends on 2)

A composition according to claim 2, which comprises, as the sterically hindered amine, a compound which contains at least one group of the formula I ##STR30## in which R is hydrogen or methyl.

### Claim 6 (depends on 5)

A composition according to claim 5, which comprises a sterically hindered amine of the formula II ##STR31## in which n is a number from 1 to 4, R is hydrogen or methyl,
R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.8 alkanyl, C.sub.3 -C.sub.5 alkenoyl, glycidyl, --O--C.sub.1 -C.sub.12 alkyl, --O--C.sub.1 -C.sub.8 alkanoyl or a group --CH.sub.2 CH(OH)--Z,
in which Z is hydrogen, methyl or phenyl,
R.sub.2, if n is 1, is hydrogen, C.sub.1 -C.sub.18 alkyl, which may be interrupted by one or more oxygen atoms, cyanoethyl, benzyl, glycidyl, a monovalent radical of an aliphatic, cycloaliphatic, araliphatic, unsaturated or aromatic carboxylic acid, carbamic acid or phosphorus-containing acid, or a monovalent silyl radical, and in which R.sub.2, if n is 2, is C.sub.1 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkenylene, xylylene, a divalent radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid, dicarbamic acid or phosphorus- containing acid or a divalent silyl radical, or, if n is 3, is a trivalent radical of an aliphatic, cycloaliphatic or aromatic tricarboxylic acid, of an aromatic tricarbamic acid or of a phosphorus-containing acid or a trivalent silyl radical, or, if n is 4, is a tetravalent radical of an aliphatic, cycloaliphatic or aromatic tetracarboxylic acid.

### Claim 7 (depends on 6)

A composition according to claim 6, which comprises a sterically hindered amine of the formula II
in which n is 1 or 2,
R is hydrogen or methyl,
R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, allyl, benzyl, acetyl or acryloyl and
R.sub.2, if n is 1, is a radical of an aliphatic carboxylic acid having 2 to 18 C atoms, of a cycloaliphatic carboxylic acid having 7 to 15 C atoms, of an .alpha.,.beta.-unsaturated carboxylic acid having 3 to 5 C atoms or of an aromatic carboxylic acid having 7 to 15 C atoms, and, if n is 2, is a radical of an aliphatic dicarboxylic acid having 2 to 36 C atoms, of a cycloaliphatic or aromatic dicarboxylic acid having 8 to 14 C atoms or of an aliphatic, cycloaliphatic or aromatic dicarbamic acid having 8 to 14 C atoms.

### Claim 8 (depends on 5)

A composition according to claim 5, which comprises a sterically hindered amine of the Formula (III) ##STR32## in which n is the number 1 or 2, R is hydrogen or methyl,
R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.8 alkanoyl, C.sub.3 -C.sub.5 alkanoyl, glycidyl, --O--C.sub.1 -C.sub.12 alkyl, --O--C.sub.1 -C.sub.8 alkanoyl or a group --CH.sub.2 CH(OH)--Z,
in which Z is hydrogen, methyl or phenyl,
R.sub.3 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.5 hydroxyalkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.8 aralkyl, C.sub.2 -C.sub.18 alkanoyl, C.sub.3 -C.sub.5 alkenoyl or benzoyl and
R.sub.4, if n is 1, is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by a hydroxyl, cyano, alkoxycarbonyl or carbamide group, glycidyl, or a group of the formula --CH.sub.2 --CH(OH)--Z or of the formula --CONH--Z,
in which Z is hydrogen, methyl or phenyl;
or, if n is 2, is C.sub.2 -C.sub.12 alkylene, C.sub.6 -C.sub.12 arylene, xylylene, a --CH.sub.2 --CH(OH)--CH.sub.2 -- group or a group --CH.sub.2 --CH(OH)--CH.sub.2 --O--D--O--,
in which D is C.sub.2 -C.sub.10 alkylene, C.sub.6 -C.sub.15 arylene or C.sub.6 -C.sub.12 cycloalkylene,
or, provided that R.sub.3 is not alkanoyl, alkenoyl or benzoyl,
R.sub.4 can also be a divalent radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid or also the group --CO--,
or R.sub.3 and R.sub.4 together, if n is 1, can be the divalent radical of an aliphatic, cycloaliphatic or aromatic 1,2- or 1,3-dicarboxylic acid.

### Claim 9 (depends on 5)

A composition according to claim 5, which comprises a statically hindered amine of the formula (IV) ##STR33## in which n is the number 1 or 2, R is hydrogen or methyl,
R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.8 alkanoyl, C.sub.3 -C.sub.5 alkenoyl, glycidyl, --O--C.sub.1 -C.sub.12 alkyl, --O--C.sub.1 -C.sub.8 alkanoyl or a group --CH.sub.2 CH(OH)--Z,
in which Z is hydrogen, methyl or phenyl,
R.sub.5, if n is 1, is C.sub.2 -C.sub.8 alkylene or -hydroxyalkylene or C.sub.4 -C.sub.22 acyloxyalkylene, or, if n is 2, is the group (--CH.sub.2).sub.2 C(CH.sub.2 --).sub.2.

### Claim 10 (depends on 5)

A composition according to claim 5, which comprises a sterically hindered amine of the formula (VA), (VB) or (VC) ##STR34## in which n is the number 1 or 2, R is hydrogen or methyl,
R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.8 alkanoyl, C.sub.3 -C.sub.5 alkenoyl, glycidyl, --O--C.sub.1 -C.sub.12 alkyl, --O--C.sub.1 -C.sub.8 alkanoyl or a group --CH.sub.2 CH(OH)--Z,
in which Z is hydrogen, methyl or phenyl,
R.sub.6 is hydrogen, C.sub.1 -C.sub.12 alkyl, allyl, benzyl, glycidyl or C.sub.2 -C.sub.6 alkoxyalkyl and
R.sub.7, if n is 1, is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.7 cycloalkyl,
C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.6 -C.sub.10 aryl, glycidyl or a group of the formula --(CH.sub.2).sub.p --COO--Q or of the formula --(CH.sub.2).sub.p --O--CO--Q,
in which p is 1 or 2 and
Q is C.sub.1 -C.sub.4 alkyl or phenyl,
or, if n is 2, is C.sub.2 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkenylene, C.sub.6 -C.sub.12 arylene, a group --CH.sub.2 --CH(OH)--CH.sub.2 --O--D--O--CH.sub.2 --CH(OH)--CH.sub.2 --,
in which D is C.sub.2 -C.sub.10 alkylene, C.sub.6 -C.sub.15 arylene, C.sub.6 -C.sub.12 cycloalkylene,
or a group --CH.sub.2 CH(OZ')CH.sub.2 --(OCH.sub.2 --CH(OZ')CH.sub.2).sub.2 --,
in which Z' is hydrogen, C.sub.1 -C.sub.18 alkyl, allyl, benzyl, C.sub.2 -C.sub.12 alkanoyl or benzoyl, T.sub.1 and T.sub.2 independently of one another are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.9 aralkyl which are unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 alkyl, or T.sub.1 and T.sub.2, together with the C atom joining them, form a C.sub.5 -C.sub.12 cycloalkane ring.

### Claim 11 (depends on 5)

A composition according to claim 5, which comprises a sterically hindered amine of the formula (VI) ##STR35## in which n is the number 1 or 2 and R.sub.8 is a group of the formula ##STR36## in which R is hydrogen or methyl,
R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.8 alkanoyl, C.sub.3 -C.sub.5 alkenoyl, glycidyl, --O--C.sub.1 -C.sub.12 alkyl, --O--C.sub.1 -C.sub.8 alkanoyl or a group --CH.sub.2 CH(OH)--Z,
in which Z is hydrogen, methyl or phenyl,
E is --O-- or --NR.sub.11 --,
A is C.sub.2 -C.sub.6 alkylene or --(CH.sub.2).sub.3 --O-- and
x is the number 0 or 1,
R.sub.9 is the same as R.sub.8 or is one of the groups --NR.sub.11 R.sub.12, --OR.sub.13, --NHCH.sub.2 OR.sub.13 or --N(CH.sub.2 OR.sub.13).sub.2,
R.sub.10, if n is 1, is the same as R.sub.8 or R.sub.9, or, if n is 2, is a group --E--B--E--,
in which B is C.sub.2 -C.sub.6 alkylene, which may be interrupted by --N(R.sub.11)--,
R.sub.11 is C.sub.1 -C.sub.12 alkyl, cyclohexyl, benzyl or C.sub.1 -C.sub.4 hydroxyalkyl, or a group of the formula ##STR37## R.sub.12 is C.sub.1 -C.sub.12 alkyl, cyclohexyl, benzyl or C.sub.1 -C.sub.4 hydroxyalkyl and
R.sub.13 is hydrogen, C.sub.1 -C.sub.12 alkyl or phenyl, or
R.sub.11 and R.sub.12 together are C.sub.4 -C.sub.5 alkylene, C.sub.4 -C.sub.5 oxaalkylene or a group of the formula ##STR38## or R.sub.11 and R.sub.12 are also each a group of the formula ##STR39##

### Claim 12 (depends on 5)

A composition according to claim 5, which comprises, as the sterically hindered amine, an oligomeric or polymeric compound, having a recurring structural unit which contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (I).

### Claim 13 (depends on 3)

A composition according to claim 3, which comprises, as the UV absorber, a 2-(2'-hydroxyphenyl)-benzotriazole, a 2-hydroxybenzophenone, an ester of a substituted or unsubstituted benzoic acid or a 2-(2-hydroxyphenyl)-1,3,5-triazine.

### Claim 14 (depends on 13)

A composition according to claim 13, which comprises, as the UV absorber, 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-benzotriazole, 2-(5'-tertbutyl-2'-hydroxyphenyl)-benzotriazole, 2-(2'-hydroxy-5'- (1,1,3,3-tetramethylbutyl)phenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)-benzotriazole, 2-(2'-hydroxy-4'-octoxyphenyl)-benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)-benzotriazole, 2-(3',5'-bis-(.alpha.,.alpha.-dimethylbenzyl)-2'-hydroxyphenyl)-benzotriaz ole, mixture of 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5-chloro-b enzotriazole, 2-(3'-tertbutyl-5'-›2-(2-ethylhexyloxy)-carbonylethyl!-2'-hydroxyphenyl)-5 -chloro-benzotriazole, 2-(3'-tertbutyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-ben zotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-benzotriazo le, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-benzotriaz ole, 2-(3'-tert-butyl-5'-›2-(2-ethylhexyloxy)carbonylethyl!-2'-hydroxyphenyl)-b enzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenyl-benzotri azole, and 2,2'-methylene-bis›4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-yl-phenol !; transesterification product of 2-›3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxy-phenyl!-benzotriaz ole with polyethylene glycol 300; or ›R--CH.sub.2 CH.sub.2 --COO(CH.sub.2).sub.3 .brket close-st..sub.2
in which R is 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-yl-phenyl.

### Claim 15 (depends on 4)

A composition according to claim 4, which comprises, as the UV absorber, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)-benzotriazole.

### Claim 16 (depends on 14)

A composition according to claim 14, which comprises, as the antioxidant a compound selected from the group consisting of: alkylated monophenols, alkylthiomethylphenols, hydroquinones and alkylated hydroquinones, hydroxylated thiodiphenyl ethers, alkylidene-bisphenols, O--, N-- and S-benzyl compounds, hydroxybenzylated malonates, hydroxybenzyl aromatics, triazine compounds, benzylphosphonates, acylaminophenols, esters of .beta.-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid, of .beta.-(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acid, of .beta.-(3,5-dicyclohexyl-4-hydroxyphenyl)-propionic acid or of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with mono- or polyhydric alcohols and amides of .beta.-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid.

### Claim 17 (depends on 16)

A composition according to claim 16, which comprises, as the antioxidant, an ester of .beta.(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid with a mono- or polyhydric alcohol selected from the group consisting of methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris-(hydroxyethyl) isocyanurate, N,N'-bis-(hydroxyethyl)-oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane and 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo-›2.2.2!-octane.

### Claim 18 (depends on 17)

A composition according to claim 17, which comprises, as the antioxidant, .beta.-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid which has been esterified with octanol.

### Claim 19 (depends on 1)

A composition according to claim 1, which comprises a mixture of
b) a polyalcohol which is completely or partially esterified with a fatty acid and
c) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, and an alkylene oxide, the polyalcohol being selected from the group consisting of diglycol, alkylene or dialkylene glycols, sorbitan, sorbitol, mannitol, xylitol, pentaerythritol, diglycerol, glycerol and glycerol-sorbitol.

### Claim 20 (depends on 19)

A composition according to claim 19, which comprises a mixture of
b) a polyalcohol which is completely or partly esterified with a fatty acid and
c) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, and an alkylene oxide, the fatty acid being selected from the group consisting of caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic, coconut fat-(C.sub.8 -C.sub.18), decenoic, dodecenoic, tetradecenoic, hexadecenoic, oleic, linoleic, linolenic, eicosenoic, docosenoic and clupanodonic acid.

### Claim 21 (depends on 20)

A composition according to claim 20, which comprises, as the polyalcohol which is completely or partly esterified with a fatty acid, sorbitan, sorbitol, mannitol, xylitol or pentaerythritol which is esterified with 1 to 3 mol of lauric, palmitic, stearic, oleic, linoleic or linolenic acid.

### Claim 22 (depends on 1)

A composition according to claim 1, which comprises, as the alkylene oxide, ethylene oxide.

### Claim 23 (depends on 22)

A composition according to claim 22, which comprises a reaction product of sorbitan esterified with 1 to 3 moles of oleic acid with 5 to 40 moles of ethylene oxide.

### Claim 24 (depends on 2)

A composition according to claim 2, which comprises
a) 75 to 95% by weight of a water-insoluble sterically hindered amine and
b) 25 to 5% by weight of a mixture of
b1) a polyalcohol which is completely or partly esterified with a fatty acid and
b2) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, and an alkylene oxide, the ratio of components b1):b2) being between 3:7 and 7:3.

### Claim 25 (depends on 3)

A composition according to claim 3, which comprises
a) 75 to 95% by weight of a water-insoluble UV absorber and
b) 25 to 5% by weight of a mixture of
b1) a polyalcohol which is completely or partly esterified with a fatty acid and
b2) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, and an alkylene oxide, the ratio of components b1):b2) being between 9:1 and 5:5.

### Claim 26 (depends on 4)

A composition according to claim 4, which comprises
a) 75 to 95% by weight of a water-insoluble antioxidant and
b) 25 to 5% by weight of a mixture of
b1) a polyalcohol which is completely or partly esterified with a fatty acid and
b2) a reaction product of a polyalcohol, which is completely or partly esterified with a fatty acid, and an alkylene oxide, the ratio of components b1):b2) being between 1:9 and 5:5.

### Claim 27 (depends on 2)

A process for improving the light stability of leather, which comprises applying a composition according to claim 2 to the leather.

### Claim 28

A process for improving the resistance of a leather or imitation leather substrate to the influence of light or heat or both, which comprises treating said substrate with an aqueous liquor consisting essentially of water, an amount which is effective to emulsify the below-specified combination of components a), b) and c) of an emulsifier or dispersant and an amount which is effective to improve the resistance of said leather or imitation leather to the influence of light and/or heat of
a) a water-insoluble sterically hindered amine and,
b) a water-insoluble UV absorber or
c) a water-insoluble antioxidant,
or a) plus both of b) and c).

### Claim 29 (depends on 28)

A process according to claim 28 which comprises an emulsifier.

### Claim 30 (depends on 28)

The leather or imitation leather treated with a process according to claim 28.

### Claim 31

An aqueous liquor for improving the resistance of a leather or imitation leather substrate to the influence of light or heat or both, which aqueous liquor consists essentially of water, an amount which is effective to emulsify the below-specified combination of components a), b) and c) of an emulsifier or dispersant and an amount which is effective to improve the resistance of the leather or imitation leather to the influence of light and/or heat of
a) a water-insoluble sterically hindered amine and,
b) a water-insoluble UV absorber or
c) a water-insoluble antioxidant,
or a) plus both of b) and c).

### Claim 32 (depends on 31)

An aqueous liquor according to claim 31 which comprises an emulsifier.