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US4154722A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyalkylpiperidinyl esters of diazocarboxylic acid and their use for stabilizing polymers

Assignee: BASF Corp
•
Filing: 1977-06-20
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Granted: 1979-05-15
•
Expires: 1997-06-20
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Abstract

Abstract Polyalkylpiperidinyl esters of diazocarboxylic acids are prepared, which compounds protect organic polymers against UV light degradation. The light stabilizers have the ability to react with the organic polymeric substrates thus making the piperidinyl esters migration and extraction resistant. Polymers which may be stabilized with the compounds of this invention include polypropylene, polyethylene, polystyrene and polyamides.

Inventors

  • 👤 Roger Malherbe
  • 👤 Michael Rasberger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 01:19
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/10; C07D295/104; C07D295/108; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 606 words
A diazo compound of the formula ##STR3## in which R 1 is a radical of the formula ##STR4## and R 2 represents hydrogen --CHO, --CN, --NO 2 , --COR 1 , --COR 5 , --SO 2 R 6 , --COOR 7 , --CONH 2 , --CONHR 17 , --CON(R 17 ) 2 , --P(O)(C 6 H 5 ) 2 or --P(O)(OR 18 ) 2 , X denotes H, O, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, alkoxyalkyl with 3-10 C atoms, phenylalkyl with 7-9 C atoms, 2,3-epoxypropyl --CH 2 COOR 8 , --CH 2 CH 2 COOR 8 , --CH 2 CH(R 9 )--OR 10 , --COR 11 , --COOR 12 or --CONHR 13 , Y denotes oxygen, NH or N-alkyl with 1-4 C atoms, R 3 denotes H or alkyl with 1-4 C atoms, R 4 denotes, H, --OR 14 or --N(R 15 )(R 16 ), R 5 and R 6 denote alkyl with 1-18 C atoms, cyclohexyl, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, phenylalkyl with 7-9 C atoms phenylalkyl with 7-9 C atoms substituted by one or two alkyl with 1-4 C atoms or by hydroxyl or combinations thereof, or a group of the formula --CH 2 COR 1 or --CH 2 COOR 12 , R 7 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, cycloalkyl with 5-12 C atoms, phenyl, alkylphenyl with 7-14 C atoms or phenylalkyl with 7-9 C atoms, R 8 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, phenyl, benzyl or cyclohexyl, R 9 denotes H, methyl or phenyl, R 10 denotes, H, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl, C 7 -C 14 aralkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkenyl or an aliphatic acyl, aromatic acyl, araliphatic acyl or cycloaliphatic acyl each acyl group derived from a monocarboxylic acid with up to 18 C atoms, wherein the aromatic part can be substituted by halogen, alkoxy or alkyl each with 1-4 C atoms or hydroxyl or combinations thereof, R 11 denotes H, alkyl with 1-6 C atoms or alkenyl with 2-4 C atoms, R 12 denotes alkyl with 1-12 C atoms, phenyl, benzyl or cyclohexyl, R 13 denotes alkyl with 1-12 C atoms, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, phenylalkyl with 7-9 C atoms or cyclohexyl, R 14 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, benzyl, 2-cyanoethyl, an aliphatic acyl, cycloaliphatic acyl, aromatic acyl or araliphatic acyl each aryl group derived from a monocarboxylic acid with up to 18 C atoms, which can be substituted in the aromatic part by halogen, alkyl or alkoxy each with 1-4 C atoms or hydroxyl or combinations thereof, R 15 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms or phenylalkyl with 7-9 C atoms, R 16 denotes an aliphatic acyl, cycloaliphatic acyl, aromatic acyl or araliphatic acyl each acyl group derived from a monocarboxylic acid with up to 18 C atoms, which can be substituted in the aromatic part by halogen, alkyl or alkoxy each with 1-4 C atoms or hydroxyl or combinations thereof, R 17 denotes alkyl with 1-12 C atoms, cyclohexyl, benzyl or phenyl and R 18 denotes alkyl with 1-18 C atoms, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, or phenyl-alkyl with 7-9 C atoms.
Claim 2
Dependent Claim 606 words
A diazo compound of the formula ##STR3## in which R 1 is a radical of the formula ##STR4## and R 2 represents hydrogen --CHO, --CN, --NO 2 , --COR 1 , --COR 5 , --SO 2 R 6 , --COOR 7 , --CONH 2 , --CONHR 17 , --CON(R 17 ) 2 , --P(O)(C 6 H 5 ) 2 or --P(O)(OR 18 ) 2 , X denotes H, O, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, alkoxyalkyl with 3-10 C atoms, phenylalkyl with 7-9 C atoms, 2,3-epoxypropyl --CH 2 COOR 8 , --CH 2 CH 2 COOR 8 , --CH 2 CH(R 9 )--OR 10 , --COR 11 , --COOR 12 or --CONHR 13 , Y denotes oxygen, NH or N-alkyl with 1-4 C atoms, R 3 denotes H or alkyl with 1-4 C atoms, R 4 denotes, H, --OR 14 or --N(R 15 )(R 16 ), R 5 and R 6 denote alkyl with 1-18 C atoms, cyclohexyl, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, phenylalkyl with 7-9 C atoms phenylalkyl with 7-9 C atoms substituted by one or two alkyl with 1-4 C atoms or by hydroxyl or combinations thereof, or a group of the formula --CH 2 COR 1 or --CH 2 COOR 12 , R 7 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, cycloalkyl with 5-12 C atoms, phenyl, alkylphenyl with 7-14 C atoms or phenylalkyl with 7-9 C atoms, R 8 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, phenyl, benzyl or cyclohexyl, R 9 denotes H, methyl or phenyl, R 10 denotes, H, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl, C 7 -C 14 aralkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkenyl or an aliphatic acyl, aromatic acyl, araliphatic acyl or cycloaliphatic acyl each acyl group derived from a monocarboxylic acid with up to 18 C atoms, wherein the aromatic part can be substituted by halogen, alkoxy or alkyl each with 1-4 C atoms or hydroxyl or combinations thereof, R 11 denotes H, alkyl with 1-6 C atoms or alkenyl with 2-4 C atoms, R 12 denotes alkyl with 1-12 C atoms, phenyl, benzyl or cyclohexyl, R 13 denotes alkyl with 1-12 C atoms, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, phenylalkyl with 7-9 C atoms or cyclohexyl, R 14 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms, alkinyl with 3-6 C atoms, benzyl, 2-cyanoethyl, an aliphatic acyl, cycloaliphatic acyl, aromatic acyl or araliphatic acyl each aryl group derived from a monocarboxylic acid with up to 18 C atoms, which can be substituted in the aromatic part by halogen, alkyl or alkoxy each with 1-4 C atoms or hydroxyl or combinations thereof, R 15 denotes alkyl with 1-18 C atoms, alkenyl with 3-6 C atoms or phenylalkyl with 7-9 C atoms, R 16 denotes an aliphatic acyl, cycloaliphatic acyl, aromatic acyl or araliphatic acyl each acyl group derived from a monocarboxylic acid with up to 18 C atoms, which can be substituted in the aromatic part by halogen, alkyl or alkoxy each with 1-4 C atoms or hydroxyl or combinations thereof, R 17 denotes alkyl with 1-12 C atoms, cyclohexyl, benzyl or phenyl and R 18 denotes alkyl with 1-18 C atoms, aryl with 6-10 C atoms, aryl with 6-10 C atoms substituted by chlorine or alkyl with 1-8 C atoms, or phenyl-alkyl with 7-9 C atoms.
Claim 3
Dependent Claim 14 words
A compound according to claim 1, in which R 3 denotes hydrogen or methyl.
Claim 4
Dependent Claim 12 words
A compound according to claim 1 in which R 3 denotes hydrogen.
Claim 5
Dependent Claim 85 words
A compound according to claim 1 in which R 1 is a radical of the formula, ##STR5## wherein X represents hydrogen, alkyl with 1-8 C atoms, allyl, benzyl or one of the groups --CH 2 COOR 8 , --CH 2 CH 2 COOR 8 , --CH 2 CH 2 OR 10 or --COR 11 and R 8 denotes alkyl with 1-12 C atoms, R 10 denotes hydrogen or alkanoyl with 1-18 C atoms and R 11 denotes alkyl with 1-3 C atoms, vinyl or propenyl.
Claim 6
Dependent Claim 38 words
A compound according to claim 1 in which R 1 is a radical of the formula ##STR6## wherein R 4 represents hydrogen or --OR 14 and R 14 represents an aliphatic acyl with 1-18 C atoms or benzoyl.
Claim 7
Dependent Claim 60 words
A compound according to claim 1 in which R 2 is hydrogen, --CN, --COR 1 , --COR 5 , --SO 2 R 6 or --COOR 7 , wherein R 5 denotes alkyl with 1-8 C atoms, phenyl, 4-hydroxy-3,5-di-tert.butyl-phenyl or 2-(4-hydroxy-3,5-di-tert.butylphenyl)-ethyl, R 6 denotes alkyl with 1-12 C atoms, phenyl or 4-hydroxy-3,5-di-tert.butyl-benzyl and R 7 denotes alkyl with 1-18 C atoms.
Claim 8
Dependent Claim 31 words
A compound according to claim 1 in which R 1 is a radical of the formula ##STR7## wherein R 3 is hydrogen, X is hydrogen or methyl and Y is oxygen.
Claim 9
Dependent Claim 25 words
A compound according to claim 1 in which R 1 is a radical of the formula ##STR8## wherein R 3 and R 4 are hydrogen.
Claim 10
Dependent Claim 41 words
A compound according to claim 7 in which R 2 is hydrogen, --CN, --COR 1 , --COR 5 or --COOR 7 , R 5 denotes alkyl with 1-6 C atoms or phenyl and R 7 denotes alkyl with 1-4 C atoms.
Claim 11
Dependent Claim 40 words
A compound according to claim 8 in which R 2 is hydrogen, --CN, --COR 1 , --COR 5 or --COOR 7 , R 5 denotes alkyl with 1-6 atoms or phenyl and R 7 denotes alkyl with 1-4 C atoms.
Claim 12
Dependent Claim 7 words
The compound according to claim 1, bis-(2,2,6,6-tetramethyl-4-piperidinyl)-diazomalonate.
Claim 13
Dependent Claim 7 words
The compound according to claim 1, bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)-diazomalonate.
Claim 14
Dependent Claim 38 words
A composition of matter stabilized against UV light degradation which comprises an organic polymeric material normally subject to UV light degradation containing from 0.1 to 1% by weight of at least one diazo compound according to claim 1.
Claim 15
Dependent Claim 14 words
A polymer according to claim 13, which is a polymer of mono or diolefins.

References Cited (Backward Citations)

US3440239A Cited
US3509131A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-05-14 1982-11-13 1983-05-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-05-14 1986-11-13 1987-05-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-05-14 1990-11-13 1991-05-15 $7700.00 Window Closed / Lapsed

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