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N-(Polyalkylpiperidinyl)-carbamates of polyols

Assignee: BASF Corp
•
Filing: 1984-01-16
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Granted: 1985-12-03
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Expires: 2004-01-16
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Abstract

Abstract Compounds of the formula I <IMAGE> I in which m is zero, 1 or 2 and n is 2, 3 or 4, R1 is hydrogen or C1-C4-alkyl, A is the n-valent radical of a polyol and R2 and R3 are monovalent radicals as defined in claim 1, are outstanding light stabilizers for organic materials, particularly for organic polymers.

Inventors

  • 👤 Friedrich Karrer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 10:46
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/26; C07D211/28; C07D211/36; C07D211/56; C07D211/58

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 615 words
A compound of the formula ##STR41## in which m is zero, 1 or 2 and n is 2, 3 or 4, R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is hydrogen, C 1 -C 12 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 5 -alkinyl, C 7 -C 12 -aralkyl, glycidyl, cyanomethyl or one of the groups --CO--NH--R 4 , --CO--N(R 5 ) 2 , --COOR 6 , --CH 2 COOR 6 , --CH 2 CON(R 5 ) 2 , --CO--R 7 or --CH 2 CH(R 8 )OR 9 , R 3 is hydrogen, C 1 -C 20 -alkyl or C 1 -C 6 -alkyl, C 3 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, C 6 -C 12 -cycloalkylalkyl, C 6 -C 10 -aryl, C 7 -C 15 -alkylaryl or C 7 -C 12 -aralkyl which is substituted by --OR 10 , --OOC--R 11 , --CN, --COOR 12 , --N(R 13 )(R 14 ) or -- CON(R 13 )(R 14 ), or is a group of the formula II ##STR42## in which B is a direct bond, --CH 2 CH 2 -- or --CH 2 CH 2 O --, R 4 is C 1 -C 8 -alkyl, C 5 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 15 -alkylaryl, R 5 is C 1 -C 8 -alkyl, cycloalkyl, phenyl or benzyl, or the two radicals R 5 , together with the N atom to which they are attached, form a 5-membered to 7-membered heterocyclic ring, R 6 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, allyl, benzyl or phenyl, R 7 is hydrogen, C 1 -C 11 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, phenyl or C 7 -C 12 -aralkyl, R 8 is hydrogen, methyl, ethyl, phenyl, butoxymethyl or phenoxymethyl, R 9 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, benzyl or --CO--R 11 , R 10 is hydrogen, C 1 -C 12 -alkyl or C 5 -C 8 -cycloalkyl, R 11 is C 1 -C 11 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, phenyl, C 7 -C 12 -aralkyl or phenyl or C 7 -C 9 -phenylalkyl which is substituted by C 1 -C 4 -alkyl and/or OH, or is a group --NH--R 4 , R 12 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, allyl, benzyl, C 7 -C 9 -phenylalkyl which is substituted in the phenyl radical by OH and C 1 -C 4 -alkyl, or phenyl or is a group of the formula II, R 13 is C 1 -C 8 -alkyl, cyclohexyl, benzyl, phenyl or a radical of the formula II, and R 14 is hydrogen, C 1 -C 8 -alkyl, cyclohexyl or a radical of the formula II, or R 14 , together with R 13 and the N atom, forms a 5-membered to 7-membered heterocyclic radical, and A is the n-valent radical of a polyol and, if n is 2, is C 2 -C 16 -alkylene or is C 4 -C 20 -alkylene, C 4 -C 10 -alkenylene, C 6 -C 8 -cycloalkylene, C 8 -C 12 -dialkylenecycloalkane, C 8 -C 14 -dialkylenearene, C 6 -C 12 -arylene or C 13 -C 18 -diphenylenealkane which is interrupted by one or more --O-- or --N(C 1 -C 4 -alkyl)- groups, or is a group of the formula III ##STR43## and, if n is 3, A is a trivalent aliphatic or cycloaliphatic hydrocarbon radical having 3-20 C atoms and, if n is 4, is a tetravalent aliphatic hydrocarbon radical having 4-20 C atoms, and to acid addition salts of these compounds.
Claim 2
Dependent Claim 615 words
A compound of the formula ##STR41## in which m is zero, 1 or 2 and n is 2, 3 or 4, R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is hydrogen, C 1 -C 12 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 5 -alkinyl, C 7 -C 12 -aralkyl, glycidyl, cyanomethyl or one of the groups --CO--NH--R 4 , --CO--N(R 5 ) 2 , --COOR 6 , --CH 2 COOR 6 , --CH 2 CON(R 5 ) 2 , --CO--R 7 or --CH 2 CH(R 8 )OR 9 , R 3 is hydrogen, C 1 -C 20 -alkyl or C 1 -C 6 -alkyl, C 3 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, C 6 -C 12 -cycloalkylalkyl, C 6 -C 10 -aryl, C 7 -C 15 -alkylaryl or C 7 -C 12 -aralkyl which is substituted by --OR 10 , --OOC--R 11 , --CN, --COOR 12 , --N(R 13 )(R 14 ) or -- CON(R 13 )(R 14 ), or is a group of the formula II ##STR42## in which B is a direct bond, --CH 2 CH 2 -- or --CH 2 CH 2 O --, R 4 is C 1 -C 8 -alkyl, C 5 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 15 -alkylaryl, R 5 is C 1 -C 8 -alkyl, cycloalkyl, phenyl or benzyl, or the two radicals R 5 , together with the N atom to which they are attached, form a 5-membered to 7-membered heterocyclic ring, R 6 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, allyl, benzyl or phenyl, R 7 is hydrogen, C 1 -C 11 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, phenyl or C 7 -C 12 -aralkyl, R 8 is hydrogen, methyl, ethyl, phenyl, butoxymethyl or phenoxymethyl, R 9 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, benzyl or --CO--R 11 , R 10 is hydrogen, C 1 -C 12 -alkyl or C 5 -C 8 -cycloalkyl, R 11 is C 1 -C 11 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, phenyl, C 7 -C 12 -aralkyl or phenyl or C 7 -C 9 -phenylalkyl which is substituted by C 1 -C 4 -alkyl and/or OH, or is a group --NH--R 4 , R 12 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, allyl, benzyl, C 7 -C 9 -phenylalkyl which is substituted in the phenyl radical by OH and C 1 -C 4 -alkyl, or phenyl or is a group of the formula II, R 13 is C 1 -C 8 -alkyl, cyclohexyl, benzyl, phenyl or a radical of the formula II, and R 14 is hydrogen, C 1 -C 8 -alkyl, cyclohexyl or a radical of the formula II, or R 14 , together with R 13 and the N atom, forms a 5-membered to 7-membered heterocyclic radical, and A is the n-valent radical of a polyol and, if n is 2, is C 2 -C 16 -alkylene or is C 4 -C 20 -alkylene, C 4 -C 10 -alkenylene, C 6 -C 8 -cycloalkylene, C 8 -C 12 -dialkylenecycloalkane, C 8 -C 14 -dialkylenearene, C 6 -C 12 -arylene or C 13 -C 18 -diphenylenealkane which is interrupted by one or more --O-- or --N(C 1 -C 4 -alkyl)- groups, or is a group of the formula III ##STR43## and, if n is 3, A is a trivalent aliphatic or cycloaliphatic hydrocarbon radical having 3-20 C atoms and, if n is 4, is a tetravalent aliphatic hydrocarbon radical having 4-20 C atoms, and to acid addition salts of these compounds.
Claim 3
Dependent Claim 16 words
A compound according to claim 1 of the formula I in which R 1 is hydrogen.
Claim 4
Dependent Claim 15 words
A compound according to claim 1 of the formula I in which n is 2.
Claim 5
Dependent Claim 17 words
A compound according to claim 1 of the formula I in which R 3 is not hydrogen.
Claim 6
Dependent Claim 192 words
A compound according to claim 1 of the formula I in which m is zero and n is 2, R 1 is hydrogen, R 2 is hydrogen, C 1 -C 4 -alkyl, allyl, benzyl, cyanomethyl or --CO--R 7 , and R 3 is hydrogen, C 1 -C 12 -alkyl, C 2 -C 3 -hydroxyalkyl, cyclohexyl, phenyl, benzyl, a group of the formula II, R 11 -COOCH 2 CH 2 --, R 12 --OOC--(CH 2 ) p -- or R 13 --NH--CO--(CH 2 ) p -- in which p is 1 or 2, R 7 is C 1 -C 4 -alkyl or vinyl, R 11 is C 1 -C 4 -alkyl, --NH--(C 1 -C 4 -alkyl), phenyl or phenyl or phenylethyl which is substituted by an OH group and two C 1 -C 4 -alkyl groups, R 12 is C 1 -C 6 -alkyl, allyl, 3,5-di-tert.-butyl-4-hydroxybenzyl or a group of the formula II, R 13 is C 1 -C 6 -alkyl or a group of the formula II and A is C 2 -C 12 -alkylene, C 4 -C 6 -monooxaalkylene, C 4 -C 6 -dioxaalkylene or a group of the formula III.
Claim 7
Dependent Claim 63 words
A compound according to claim 5, in which R 3 is C 1 -C 12 -alkyl, C 2 -C 3 -hydroxyalkyl, cyclohexyl or a group of the formula II or of the formula R 12 --OOC--(CH 2 ) p -- in which p is 1 or 2 and R 12 is C 1 -C 4 -alkyl or a group of the formula II.
Claim 8
Dependent Claim 17 words
A compound according to claim 5, in which A is C 2 -C 6 -alkylene or 3-oxa-1,5-pentylene.
Claim 9
Dependent Claim 32 words
A compound according to claim 1 of formula I in which n is 2, R 1 and R 2 are hydrogen, R 3 is ethyl, m is zero and A is tetramethylene.
Claim 10
Dependent Claim 32 words
A compound according to claim 1 of formula I in which n is 2, R 1 and R 2 are hydrogen, R 3 is methyl, m is zero and A is hexamethylene.
Claim 11
Dependent Claim 38 words
A compound according to claim 1 of the formula I in which n is 2, R 1 and R 2 are hydrogen, R 3 is a group of the formula ##STR44## m is zero and A is hexamethylene.
Claim 12
Dependent Claim 36 words
A compound according to claim 1 of the formula I in which n is 2, R 1 is hydrogen, R 2 is methyl, R 3 is a group of the formula ##STR45## and A is tetramethylene.
Claim 13
Dependent Claim 25 words
A stabilised organic polymer containing, as the stabiliser, 0.05 to 4% by weight of at least one compound of the formula I of claim 1.

References Cited (Backward Citations)

US2527240A Cited
US3684765A Cited
US3904581A Cited
US3937711A Cited
US4191683A Cited
US4233412A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-02 1989-06-03 1989-12-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-02 1993-06-03 1993-12-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-02 1997-06-03 1997-12-03 $7700.00 Window Closed / Lapsed

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