US5389141A
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Stabilization of pyrrolopyrrole pigments
Assignee: BASF Corp
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Filing: 1993-12-22
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Granted: 1995-02-14
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Expires: 2013-12-22
Abstract
Abstract Pigment compositions comprising a) at least one pyrrolo[3,4-c]pyrrole pigment of the formula ##STR1## in which A and B, independently of one another, are isocyclic or heterocyclic aromatic radicals, and D is an oxygen or sulfur atom, and b) from 1 to 100% by weight, based on the pigment, of a nitroxyl compound or of an acid-addition salt thereof. These pigment compositions are distinguished by excellent light stability and weathering resistance.
Inventors
- 👤 Laurent Chassot
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 01:06
CPC Classifications
C; C09; C09B; C09B57/00; C09B57/004; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C08K5/0008; C08K5/0041; C08K5/32; C08K5/3417; C08K5/3432; C08K5/3435; C09B67/00; C09B67/0001; C09B67/002; C09B67/006; C09B67/0065; C09B67/0071; C09B67/0092
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
587 words
A light-stabilised pigment composition comprising a) at least one pyrrolo[3,4-c]pyrrole pigment of the formula ##STR129## in which A and B, independently of one another, are isocyclic or heterocyclic aromatic radicals; and D is an oxygen or sulfur atom; and b) from 1 to 100% by weight, based on the pigment, of a nitroxyl compound of the formula ##STR130## in which R 12 is C 1 -C 18 alkyl or C 1 -C 18 alkoxy; G is a divalent group of the formula --CR 13 ═CH-- or --CHR 13 --CH 2 --; R 13 is C 1 -C 18 alkyl; Q is a group of the formula ##STR131## in which the bond denoted by * is the bond leading to T; T is a direct bond or a group of the formula ##STR132## in which R 14 is hydrogen, halogen or C 1 -C 4 alkyl, is --(CH 2 ) r --, in which r is 1 or 2; m is the number 1, 2, 3, 4 or 6; X, if m=1, is hydrogen, C 1 -C 18 alkyl, phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl or halogen, or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --OCO--NR 15 R 16 , --OSO 2 --NR 15 R 16 , --OCO--R 16 , --COOR 16 ,--CONR 15 R 16 , --NR 15 --COR 16 , --NR 15 --CONR 15 R 16 , --OR 16 , --NR 15 R 16 , ##STR133## in which R 15 is hydrogen or C 1 -C 18 alkyl, R 16 is C 1 -C 18 alkyl, C 2 -C 12 alkenyl, C 5 -C 12 cycloalkyl, phenyl or naphthyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, phenyl or nitro, or a --(CH 2 ) s --CHR 17 R 18 group where s is zero, 1, 2 or 3, R 17 is hydrogen, methyl or phenyl, and R 18 is --OH, halogen, --COOCH 3 or --COOC 2 H 5 ; X, if m=2, is a group of the formula --(CH 2 ) p or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, a group of the formula --O--(CH 2 ) o --O--, --NR 15 --(CH 2 ) p --NR 15 --, --OCO--M--COO--, --NR 15 --CO--M--CO--NR 15 --, --OCO--NH--M--NH--COO-- or --NR 15 --CONH--M--NHCO--NR 15 --, in which M is --(CH 2 ) p --, ##STR134## and p is a number between 2 and 10; X, if m=3, is a ##STR135## X, if m=4, is a ##STR136## X, if m=6, is a ##STR137## group; X 2 is C 8 -C 18 alkyl: n is the number 1 or 2; V, if n=1, is C 2 -C 8 alkylene, hydroxyalkylene or C 4 -C 22 acyloxyalkylene; or V, if n=2, is the (--CH 2 ) 2 C(CH 2 --) 2 or ##STR138## group; Z is a group of the formula ##STR139## in which the bond denoted by * is the bond leading to W; W, if n=1, is a --OCOR 19 group, in which R 19 is C 1 -C 18 alkyl, or phenyl or naphthyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; or W, if n=2, is a group of the formula --OCO--(CH 2 ) p --COO-- or ##STR140## and Y is O•.
Claim 2
Dependent Claim
587 words
A light-stabilised pigment composition comprising a) at least one pyrrolo[3,4-c]pyrrole pigment of the formula ##STR129## in which A and B, independently of one another, are isocyclic or heterocyclic aromatic radicals; and D is an oxygen or sulfur atom; and b) from 1 to 100% by weight, based on the pigment, of a nitroxyl compound of the formula ##STR130## in which R 12 is C 1 -C 18 alkyl or C 1 -C 18 alkoxy; G is a divalent group of the formula --CR 13 ═CH-- or --CHR 13 --CH 2 --; R 13 is C 1 -C 18 alkyl; Q is a group of the formula ##STR131## in which the bond denoted by * is the bond leading to T; T is a direct bond or a group of the formula ##STR132## in which R 14 is hydrogen, halogen or C 1 -C 4 alkyl, is --(CH 2 ) r --, in which r is 1 or 2; m is the number 1, 2, 3, 4 or 6; X, if m=1, is hydrogen, C 1 -C 18 alkyl, phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl or halogen, or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --OCO--NR 15 R 16 , --OSO 2 --NR 15 R 16 , --OCO--R 16 , --COOR 16 ,--CONR 15 R 16 , --NR 15 --COR 16 , --NR 15 --CONR 15 R 16 , --OR 16 , --NR 15 R 16 , ##STR133## in which R 15 is hydrogen or C 1 -C 18 alkyl, R 16 is C 1 -C 18 alkyl, C 2 -C 12 alkenyl, C 5 -C 12 cycloalkyl, phenyl or naphthyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, phenyl or nitro, or a --(CH 2 ) s --CHR 17 R 18 group where s is zero, 1, 2 or 3, R 17 is hydrogen, methyl or phenyl, and R 18 is --OH, halogen, --COOCH 3 or --COOC 2 H 5 ; X, if m=2, is a group of the formula --(CH 2 ) p or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, a group of the formula --O--(CH 2 ) o --O--, --NR 15 --(CH 2 ) p --NR 15 --, --OCO--M--COO--, --NR 15 --CO--M--CO--NR 15 --, --OCO--NH--M--NH--COO-- or --NR 15 --CONH--M--NHCO--NR 15 --, in which M is --(CH 2 ) p --, ##STR134## and p is a number between 2 and 10; X, if m=3, is a ##STR135## X, if m=4, is a ##STR136## X, if m=6, is a ##STR137## group; X 2 is C 8 -C 18 alkyl: n is the number 1 or 2; V, if n=1, is C 2 -C 8 alkylene, hydroxyalkylene or C 4 -C 22 acyloxyalkylene; or V, if n=2, is the (--CH 2 ) 2 C(CH 2 --) 2 or ##STR138## group; Z is a group of the formula ##STR139## in which the bond denoted by * is the bond leading to W; W, if n=1, is a --OCOR 19 group, in which R 19 is C 1 -C 18 alkyl, or phenyl or naphthyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; or W, if n=2, is a group of the formula --OCO--(CH 2 ) p --COO-- or ##STR140## and Y is O•.
Claim 3
Dependent Claim
157 words
A pigment composition according to claim 1, wherein the pigment is a pyrrolo[3,4-c]pyrrole of the formula I in which A and B, independently of one another, are groups of the formula ##STR141## in which R 1 and R 2 , independently of one another, are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylmercapto, C 1 -C 18 alkylamino, CN, NO 2 , phenyl, trifluoromethyl, C 5 -C 6 cycloalkyl, imidazolyl, pyrrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl or pyrrolidinyl, E is --O--,--S--, --SO--, --SO 2 -- or --NR 7 --, R 3 and R 4 , independently of one another, are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 18 alkoxy or CN, R 5 and R 6 , independently of one another, are hydrogen, halogen or C 1 -C 6 alkyl, and R 7 is hydrogen or C 1 -C 6 alkyl.
Claim 4
Dependent Claim
96 words
A pigment composition according to claim 2, wherein the pigment is a pyrrolo[3,4-c]pyrrole of the formula I in which A and B, independently of one another, are groups of the formula ##STR142## in which R 1 and R 2 , independently of one another, are hydrogen, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylamino, CN or phenyl, E is --O--, --NR 7 -- or --SO 2 --, R 3 and R 4 are hydrogen, R 7 is hydrogen, methyl or ethyl, and D is an oxygen atom.
Claim 5
Dependent Claim
38 words
A pigment composition according to claim 2, wherein the pigment is a pyrrolo[3,4-c]pyrrole of the formula ##STR143## in which R 1 and R 2 , independently of one another, are hydrogen, methyl, tert-butyl, chlorine, bromine, CN or phenyl.
Claim 6
Dependent Claim
27 words
A pigment composition according to claim 1, wherein the pyrrolo[3,4-c]pyrrole pigment is used in fine form having a mean particle size of from 0.005 to 0.1 μm.
Claim 7
Dependent Claim
24 words
A pigment composition according to claim 1, wherein the nitroxyl compound is employed in an amount of 5-100% by weight, based on the pigment.
Claim 8
Dependent Claim
19 words
A pigment composition according to claim 1, wherein an organic or inorganic salt of the nitroxyl compound is used.
Claim 9
Dependent Claim
25 words
A pigment composition according to claim 1, wherein a nitroxyl compound of the formula VII, VIII or IX as defined in claim 1 is used.
Claim 10
Dependent Claim
162 words
A pigment composition according to claim 1, wherein a nitroxyl compound of the formula ##STR144## is used in which T is a direct bond, m is 1,2 or 3, X 1 , if m=1, is C 1 -C 18 alkyl, --OCO--R 16 , --NR 15 --COR 16 or ##STR145## in which R 15 is hydrogen or or C 1 -C 18 alkyl, and R 16 is C 1 -C 18 alkyl, or phenyl or naphthyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl or halogen, if m=2, is a --OCO--(CH 2 ) p --OCO-- or --NR 15 CO--(CH 2 ) p --CONR 15 -- group in which p is a number between 2 and 8, ##STR146## and if m=3, is a ##STR147## X 2 is C 8 -C 18 alkyl, n is the number 2, V is the (--CH 2 ) 2 C(CH 2 --) 2 or ##STR148## group, and Y is O•.
Claim 11
Dependent Claim
44 words
A pigment composition according to claim 9, wherein a nitroxyl compound of the formula XI or XII in which T is a direct bond, m is 1, X 1 is benzoyloxy or naphthyloxy, and X 2 is C 8 -C 18 alkyl, is employed.
Claim 12
Dependent Claim
57 words
A process for the light-stabilisation of pyrrolo[3,4-c]pyrrole pigments of the formula ##STR149## in which A and B, independently of one another, are isocyclic or heterocyclic aromatic radicals, and D is an oxygen or sulfur atom, by mixing or coating the pigment particles with from 1 to 100% by weight, based on the pigment, of a nitroxyl compound.
Claim 13
Dependent Claim
57 words
A process for the light-stabilisation of pyrrolo[3,4-c]pyrrole pigments of the formula ##STR149## in which A and B, independently of one another, are isocyclic or heterocyclic aromatic radicals, and D is an oxygen or sulfur atom, by mixing or coating the pigment particles with from 1 to 100% by weight, based on the pigment, of a nitroxyl compound.
Claim 14
Dependent Claim
12 words
A high-mulecular-weight organic material containing a pigment composition according to claim 1.
Claim 15
Dependent Claim
14 words
A high-molecular-weight organic material according to claim 12, in the form of a paint.
Claim 16
Dependent Claim
15 words
A high-molecular-weight organic material according to claim 13, in the form of an automotive paint.
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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) | 1998-02-13 | 1998-08-15 | 1999-02-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-02-13 | 2002-08-15 | 2003-02-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-02-13 | 2006-08-15 | 2007-02-14 | $7700.00 | Window Closed / Lapsed |