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Monoazo compounds containing long-chain alkyl radicals

Assignee: BASF Corp
•
Filing: 1989-09-11
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Granted: 1991-03-05
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Expires: 2009-09-11
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Abstract

Abstract Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R 1 and R 4 are --H or --Cl, R 2 and R 5 are --H, halogen, --NO 2 , --CN, C 1 -C 4 -alkyl, C 1 -C 4 alkoxy, --CF 3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R 3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R 1 and R 2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH 3 , --CN or --NO 2 and X 1 and X 2 , independently of one another, are --H, halogen, --CH 3 , --OCH 3 , --OC 2 H 5 or --NO 2 and X 3 is --H, --NHCO--C 1 -C 4 alkyl, benzoylamino or phenylcarboxamide which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms and/or one or two methyl or methoxy groups or an --NHCO--C 1 -C 4 alkyl group, or X 2 and X 3 together with the carbon atom to which they are bound are an aromatic carbocyclic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring, in which the heterocyclic ring contains 1 or 2 N atoms and can additionally have an O atom or S atom, and Y 1 is --H, --OCH 3 , --OC 2 H 5 or --NHCOCH 3 , with the proviso that X 3 must not be H, if X is --O-- or --NH--, are highly suitable for the mass coloration of plastics, in particular of polyolefins.

Inventors

  • 👤 Stefan Hari
  • 👤 Olof Wallquist
  • 👤 Jost VON DER Crone

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 18:21
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/22; C08K5/23; C08K5/0008; C08K5/0041; C09; C09B; C09B29/00; C09B29/0003; C09B29/10; C09B29/18; C09B29/20; C09B29/32; C09B29/33; C09B29/335; C09B29/337; C09B29/338

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 363 words
A compound of the formulae I or II ##STR32## in which A is a radical of the formulae III, IV or V ##STR33## R 1 and R 4 are --H or --Cl, R 2 and R 5 are --H, halogen, --NO 2 , --CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, --CF 3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, or by one or two chlorine atoms and one or two methyl or methoxy groups and R 3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR34## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR35## in which R 1 and R 2 are as defined above, D is a 5-benzimidazolonyl, 5- or 6-benzoxazolonyl, 6-(2,4-dihydroxy)-quinazolinyl, 6- or 7-(4-methyl)quinolone-2-yl, 6- or 7-phenmorpholone-3-yl or 6-quinazolone-4-yl radical, Z is --H, --Br, --OCH 3 , --CN or --NO 2 and X 1 , and X 2 , independently of one another, are --H, halogen, --CH 3 , --OCH 3 --OC 2 H 5 or --NO 2 and X 3 is --H, --NHCO--C 1 -C 4 -alkyl, benzoylamino or phenylcarboxamido which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms, one or two methyl or methoxy groups, one or two chlorine atoms and one or two methyl or methoxy groups, or an --NHCO--C 1 -C 4 alkyl group, or X 2 and X 3 together with the carbon atom to which they are bound are an aromatic carboxylic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring selected from the group consisting of 5-amino-benzimidazolone, 7-chloro-5-amino-benzimidazolone, 7-bromo-5-amino-benzimidazolone, 6-chloro-5-amino-benzimidazolone, 6-bromo-5-amino-benzimidazolone, 6-methoxy-5-amino-benzimidazolone, 7-methoxy-5-amino-benzimidazolone, 6-ethoxy-5-amino-benzimidazolone, 7-chloro-4-methyl-5-amino-benzimidazolone, 6-methyl-5-amino-benzimidazolone, 4,7-dimethyl-5-amino-benzimidazolone, 4-methyl-6-chloro-5-amino-benzimidazolone, 5-amino-1-methyl-benzimidazolone, 6-amino-2,4-dihydroxyquinazoline, 6-amino-1,4-dihydroxyquinazoline, 6-amino-4-methyl-2-quinolone, 7-amino-4-methyl-2-quinolone, 7-amino-4,6-dimethyl-2-quinolone, 6-amino-7-chloro-4-methyl-2-quinolone, 7-amino-4-methyl-6-methoxy-2-quinolone, 5-aminobenzoxazolone, 6-amino-benzoxazolone, 6-amino-5-methyl-benzoxazolone, 6-amino-5-chloro-benzoxazolone, 6-amino-3-phenmorpholone, 7-amino-6-chloro-3-phenmorpholone, 7-amino-6-methyl-3-phenmorpholone, 7-amino-6-methoxy-3-phenmorpholone, 6-amino-4-methyl-3-phenmorpholone, 7-amino-4-methyl-3-phenmorpholone, 7-amino-4,6-dimethyl-3-phenmorpholone, 6-amino-4-quinazolinone and 5-aminophthalimide, and Y 1 is --H, OCH 3 , --OC 2 H 5 or --NHCOCH 3 , with the proviso that X 3 must not be H, if X is --O-- or --NH--.
Claim 2
Dependent Claim 363 words
A compound of the formulae I or II ##STR32## in which A is a radical of the formulae III, IV or V ##STR33## R 1 and R 4 are --H or --Cl, R 2 and R 5 are --H, halogen, --NO 2 , --CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, --CF 3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, or by one or two chlorine atoms and one or two methyl or methoxy groups and R 3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR34## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR35## in which R 1 and R 2 are as defined above, D is a 5-benzimidazolonyl, 5- or 6-benzoxazolonyl, 6-(2,4-dihydroxy)-quinazolinyl, 6- or 7-(4-methyl)quinolone-2-yl, 6- or 7-phenmorpholone-3-yl or 6-quinazolone-4-yl radical, Z is --H, --Br, --OCH 3 , --CN or --NO 2 and X 1 , and X 2 , independently of one another, are --H, halogen, --CH 3 , --OCH 3 --OC 2 H 5 or --NO 2 and X 3 is --H, --NHCO--C 1 -C 4 -alkyl, benzoylamino or phenylcarboxamido which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms, one or two methyl or methoxy groups, one or two chlorine atoms and one or two methyl or methoxy groups, or an --NHCO--C 1 -C 4 alkyl group, or X 2 and X 3 together with the carbon atom to which they are bound are an aromatic carboxylic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring selected from the group consisting of 5-amino-benzimidazolone, 7-chloro-5-amino-benzimidazolone, 7-bromo-5-amino-benzimidazolone, 6-chloro-5-amino-benzimidazolone, 6-bromo-5-amino-benzimidazolone, 6-methoxy-5-amino-benzimidazolone, 7-methoxy-5-amino-benzimidazolone, 6-ethoxy-5-amino-benzimidazolone, 7-chloro-4-methyl-5-amino-benzimidazolone, 6-methyl-5-amino-benzimidazolone, 4,7-dimethyl-5-amino-benzimidazolone, 4-methyl-6-chloro-5-amino-benzimidazolone, 5-amino-1-methyl-benzimidazolone, 6-amino-2,4-dihydroxyquinazoline, 6-amino-1,4-dihydroxyquinazoline, 6-amino-4-methyl-2-quinolone, 7-amino-4-methyl-2-quinolone, 7-amino-4,6-dimethyl-2-quinolone, 6-amino-7-chloro-4-methyl-2-quinolone, 7-amino-4-methyl-6-methoxy-2-quinolone, 5-aminobenzoxazolone, 6-amino-benzoxazolone, 6-amino-5-methyl-benzoxazolone, 6-amino-5-chloro-benzoxazolone, 6-amino-3-phenmorpholone, 7-amino-6-chloro-3-phenmorpholone, 7-amino-6-methyl-3-phenmorpholone, 7-amino-6-methoxy-3-phenmorpholone, 6-amino-4-methyl-3-phenmorpholone, 7-amino-4-methyl-3-phenmorpholone, 7-amino-4,6-dimethyl-3-phenmorpholone, 6-amino-4-quinazolinone and 5-aminophthalimide, and Y 1 is --H, OCH 3 , --OC 2 H 5 or --NHCOCH 3 , with the proviso that X 3 must not be H, if X is --O-- or --NH--.
Claim 3
Dependent Claim 29 words
A compound according to claim 1, in which X is --O-- or --NH--, Y is a radical of the formula --COO-- or --CONH-- and n is the number 1.
Claim 4
Dependent Claim 27 words
A compound according to claim 1, in which R 3 is C 12 -C 35 alkyl, Y is --COO-- or --CONH-- and n is the number 1.
Claim 5
Dependent Claim 183 words
A compound according to claim 1, which has the formulae VI or VII ##STR36## in which X is --O-- or --NH--, R 1 is --H or --Cl, and R 2 is --Cl, --OCH 3 , --CH 3 , --OC 2 H 5 or --OC 6 H 5 , A is a radical of the formula III according to claim 12 in which Z is --H, X 1 and X 2 , independently of one another, are --H, --Cl, --CH 3 or --OCH 3 , and X 3 is --H, --NHCOCH 3 , benzoylamino or phenylcarboxamido which are each unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, one or two chlorine atoms and one or two methyl or methoxy groups or by --NHCOCH 3 , or X 2 and X 3 together with the carbon atom to which they are bound form a ring of the formulae ##STR37## and R 3 is C 12 -C 18 alkyl, with the proviso that X 3 in formula VI must not be --H, if X is --O-- or --NH--.
Claim 6
Dependent Claim 41 words
A compound according to claim 4, in which R 1 is --H, R 2 is --Cl, --CH 3 or --OCH 3 , and the group --COXR 3 in formula VII is in the para-position relative to the group R 2 .
Claim 7
Dependent Claim 33 words
A compound according to claim 4, which has the formula VIII ##STR38## in which X is --O-- or --NH--, R 2 is --CH 3 and R 3 is C 12 -C 18 alkyl.
Claim 8
Dependent Claim 132 words
A compound according to claim 1, which has the formula IX or X ##STR39## in which X is --O--, or --NH--, R 1 is --H or --Cl, R 2 is --Cl, --CH 3 or --OCH 3 and R 3 is C 12 -C 18 alkyl, X 1 and X 2 , independently of one another, are --H, --Cl, --CH 3 or --OCH 3 , and X 3 is --H, --NHCOCH 3 , benzoylamino which is unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, one or two chlorine atoms and one or two methyl or methoxy groups or by --NHCOCH 3 , or X 2 and X 3 together with the carbon atom to which they are bound form a ring of the formula ##STR40##
Claim 9
Dependent Claim 115 words
A compound of the formulae XI ##STR41## in which n is the number 1 or 2, R 1 is --H or --Cl, R 2 is --H, halogen, --NO 2 , --CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --CF 3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, or one or two chlorine atoms and one or two methyl or methoxy groups, R 3 is alkyl having at least 10 C atoms, Z is --H, --Br, --OCH 3 , --CN or NO 2 , T is --OH or halogen and X is a radical of the formulae --NH--, --O--, ##STR42##
Claim 10
Dependent Claim 115 words
A compound of the formulae XI ##STR41## in which n is the number 1 or 2, R 1 is --H or --Cl, R 2 is --H, halogen, --NO 2 , --CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --CF 3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms, one or two methyl or methoxy groups, or one or two chlorine atoms and one or two methyl or methoxy groups, R 3 is alkyl having at least 10 C atoms, Z is --H, --Br, --OCH 3 , --CN or NO 2 , T is --OH or halogen and X is a radical of the formulae --NH--, --O--, ##STR42##
Claim 11
Dependent Claim 12 words
A compound according to claim 8, which has the formula XIII ##STR43##
Claim 12
Dependent Claim 45 words
A compound of the formula XIII according to claim 9, in which R 1 is --H, R 2 is --Cl, --CH 3 or --OCH 3 , R 3 is C 12 -C 18 alkyl, X is --O-- or --NH-- and T is --OH or --Cl.

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3.5 Years (Year 4) 1994-03-04 1994-09-03 1995-03-05 $2000.00 Window Closed / Lapsed
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