US5476949A
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Finely divided highly transparent diketopyrrolopyrrole pigments
Assignee: BASF Corp
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Filing: 1994-07-21
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Granted: 1995-12-19
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Expires: 2014-07-21
Abstract
Abstract Finely divided 1,4-diketopyrrolo[3,4-c]pyrroles of the formula ##STR1## where A and B are each independently of the other a radical of the formula ##STR2## wherein at least 84% by weight of the particles have a Stokes equivalent diameter of ≦0.25 μm, and mixtures thereof. The substituents R 1 and R 2 are defined in claim 1. These pigments are notable for a very pure hue and outstanding transparency.
Inventors
- 👤 Olof Wallquist
- 👤 Gary Wooden
- 👤 Thomas Eichenberger
- 👤 Ingo Schloder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:16
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C08K5/3417; C09; C09B; C09B57/00; C09B57/004
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
64 words
Finely divided 1,4-diketopyrrolo[3,4-c]pyrroles of the formula ##STR10## where A and B are each independently of the other a radical of the formula ##STR11## where R 1 and R 2 are each independently of the other hydrogen, halogen, C 1 -C 5 alkyl or phenyl, wherein at least 84% by weight of the particles have a Stokes equivalent diameter of ≦0.25 μm, and mixtures thereof.
Claim 2
Dependent Claim
64 words
Finely divided 1,4-diketopyrrolo[3,4-c]pyrroles of the formula ##STR10## where A and B are each independently of the other a radical of the formula ##STR11## where R 1 and R 2 are each independently of the other hydrogen, halogen, C 1 -C 5 alkyl or phenyl, wherein at least 84% by weight of the particles have a Stokes equivalent diameter of ≦0.25 μm, and mixtures thereof.
Claim 3
Dependent Claim
26 words
1,4-Diketopyrrolo[3,4-c]pyrroles of the formula I according to claim 1, wherein at least 84% by weight of the particles have a Stokes equivalent diameter of ≦0.20 μm.
Claim 4
Dependent Claim
23 words
1,4-Diketopyrrolo[3,4-c]pyrroles according to claim 2, wherein, in the formula I, A and B are independently of each other radicals of the formulae ##STR12##
Claim 5
Dependent Claim
22 words
1,4-Diketopyrrolo[3,4-c]pyrroles according to claim 2, wherein, in the formula I, A and B are identical and are radicals of the formulae ##STR13##
Claim 6
Dependent Claim
16 words
1,4-Diketopyrrolo[3,4-c]pyrroles according to claim 2, comprising a solid solution of the compounds of the formulae ##STR14##
Claim 7
Dependent Claim
38 words
A 1,4-diketopyrrolo[3,4-c]pyrrole of the formula ##STR15## according to claim 2, having a CIELAB chroma C* ab ≧42 in 1% concentration in a 1.0 mm thick compression-moulded masstone PVC-P sheet produced according to DIN 53775 Parts 2 and 7.
Claim 8
Dependent Claim
38 words
A 1,4-diketopyrrolo[3,4-c]pyrrole of the formula ##STR16## according to claim 2, having a CIELAB chroma C* ab ≧42 in 1% concentration in a 1.0 mm thick compression-moulded masstone PVC-P sheet produced according to DIN 53775 Parts 2 and 7.
Claim 9
Dependent Claim
38 words
A 1,4-diketopyrrolo[3,4-c]pyrrole of the formula ##STR17## according to claim 2, having a CIELAB chroma C* ab ≧14 in 1% concentration in a 1.0 mm thick compression-moulded masstone PVC-P sheet produced according to DIN 53775 Parts 2 and 7.
Claim 10
Dependent Claim
38 words
The solid solution of the 1,4-diketopyrrolo[3,4-c]pyrroles according to claim 5, having a CIELAB chroma C* ab >36 in 1% concentration in a 1.0 mm thick compression-moulded masstone PVC-P sheet produced according to DIN 53775 Parts 2 and 7.
Claim 11
Dependent Claim
230 words
A process for preparing 1,4-diketopyrrolo[3,4-c]pyrroles of the formula I according to claim 1 by reacting in a 1:2 molar ratio 1 mol of dicyclohexyl, dialkyl, alkyl phenyl or diphenyl succinate in which alkyl is C 1 -C 18 alkyl and phenyl is unsubstituted phenyl or phenyl substituted by one or two halogen atoms or one or two C 1 -C 6 alkyl or C 1 -C 6 alkoxy groups with 2 mol of a mixture of nitriles of the formulae A-CN (III) and B-CN (IV), where A and B are each as defined above and ACN and BCN in the nitrile mixture are in a molar ratio of 100:0 to 50:50 relative to each other, in an inert organic solvent in the presence of an alkali metal or an alkali metal alkoxide as strong base at a temperature of from about 60° C. to about 140° C. to form a pigment alkali metal salt and then liberating a compound of formula I by protonating the resulting pigment alkali metal salt and subsequent conditioning, which comprises discharging the pigment alkali metal salt suspension into water and/or an alcohol ROH, where R is C 1 -C 4 alkyl, at a temperature between -20° C. and 50° C. in the presence of an acid and treating it likewise at a temperature between -20° C. and 50° C. for 10 minutes to 48 hours.
Claim 12
Dependent Claim
26 words
A process according to claim 10, wherein the acid is added to the water and/or alcohol before or together with the alkali metal pigment salt suspension.
Claim 13
Dependent Claim
19 words
A process according to claim 10, wherein the radicals A and B are each independently of the other ##STR18##
Claim 14
Dependent Claim
14 words
A process according to claim 10, wherein the radicals A and B are identical.
Claim 15
Dependent Claim
22 words
A process according to claim 10, wherein a mixture of water and alcohol in a ratio of 80-20:20-80% by volume is used.
Claim 16
Dependent Claim
13 words
A process according to claim 10, wherein the alcohol is methanol or ethanol.
Claim 17
Dependent Claim
24 words
A process according to claim 10, wherein the acid is used in a sufficient amount to obtain pH<10 at the end of the protonation.
Claim 18
Dependent Claim
24 words
A process according to claim 10, wherein the protonation is effected using an inorganic acid selected from hydrochloric acid, sulfuric acid and phosphoric acid.
Claim 19
Dependent Claim
43 words
A process according to claim 10, wherein the protonation is effected using an aliphatic or aromatic carboxylic or sulfonic acid selected from formic acid, acetic acid, propionic acid, butyric acid, hexanoic acid, oxalic acid, benzoic acid, phenylacetic acid, benzenesulfonic acid and p-toluenesulfonic acid.
Claim 20
Dependent Claim
11 words
A process according to claim 17, wherein sulfuric acid is used.
Claim 21
Dependent Claim
14 words
A process according to claim 18, wherein acetic acid or formic acid are used.
Claim 22
Dependent Claim
37 words
A process according to claim 10, wherein the protonating agent is used in any desired mixing ratios between 5 and 20 parts by weight of the protonating agent per 1 part of the alkali metal pigment salt.
Claim 23
Dependent Claim
21 words
A process according to claim 10, wherein protonation and conditioning are carried out at a temperature between -10° and 30° C.
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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) | 1998-12-18 | 1999-06-19 | 1999-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-12-18 | 2003-06-19 | 2003-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-12-18 | 2007-06-19 | 2007-12-19 | $7700.00 | Window Closed / Lapsed |