CA2128265C - Polyamides mass coloured with diketopyrrolopyrrole pigments - Google Patents
Polyamides mass coloured with diketopyrrolopyrrole pigments Download PDFInfo
- Publication number
- CA2128265C CA2128265C CA002128265A CA2128265A CA2128265C CA 2128265 C CA2128265 C CA 2128265C CA 002128265 A CA002128265 A CA 002128265A CA 2128265 A CA2128265 A CA 2128265A CA 2128265 C CA2128265 C CA 2128265C
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- CA
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- Prior art keywords
- pigment
- formula
- parts
- polyamides
- coloured
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/04—Pigments
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Coloring (AREA)
Abstract
Mass-coloured synthetic polyamide containing, as pigment, at least one diketopyrrolopyrrole pigment of formula wherein A and B are each independently of the other a radical of formula wherein Q is a -CONH2 group, m is 1 or 2, R1 and R2 are each independently of the other hydrogen, Cl, Br, CH3 or C2H5, R3 is hydrogen, CH3, C2H5 or phenyl, X is a direct bond, -O-, -S-, -SO2-, -CH=CH-, -CH2- or -C(CH3)2-, and Y is -O- or -S-.
Polyamides mass-coloured with the pigments useful in the practice of this invention have exceptional heat stability and excellent lightfastness.
Polyamides mass-coloured with the pigments useful in the practice of this invention have exceptional heat stability and excellent lightfastness.
Description
~12~~~~'.~
Polyamides mass coloured with diketopyrrolop ry role pigments The present invention relates to the mass colouration of synthetic polyamides with diketopyrrolopyrrole pigments containing carbamoyl groups.
The mass colouration of synthetic polyamides makes greater demands of the colourants than the mass colouration of other plastic materials. The melting points of synthetic polyamides are very much higher and also the chemical reactivity of the fused polyamides, especially of polyamide 66, is substantially greater, so that the colourants employed must have extremely good heat stability. There are few pigments that meet these exacting demands, particularly if superior lightfastness is additionally required.
Compared with other known diketopyrrolopyrrole pigments as disclosed, inter alia, in US patents 4 415 685 and 4 579 949, the diketopyrrolopyrrole pigments containing carbamoyl groups used in the practice of this invention for colouring synthetic polyamides do not have any exceptional properties when used for colouring other plastic materials.
Surprisingly, however, it has been found that they have an unexpectedly enhanced heat stability and quite outstanding lightfastness when used for colouring synthetic polyamides.
Accordingly, the present invention relates to mass-coloured synthetic polyamide containing, as pigment, at least one diketopyrrolopyrrole pigment of formula A O
W
HN NH
O B
wherein A and B are each independently of the other a radical of formula ~~_2~2 -z-Q
(~, m X > >
m R~ R3 / ~ \ /
O , ~ O , or \ ~' N
Q
O
i wherein Q is a -CONH2 group, m is 1 or 2, Rl and R2 are each independently of the other hydrogen, Cl, Br, CH3 or C2H5, R3 is hydrogen, CH3, C2H5 or phenyl, X is a direct bond, -O-, -S-, -S02-, -CH=CH-, -CH2- or -C(CH3)2-, and Y is -O- or -S-.
particularly suitable diketopyrrolopyrrole pigments of formula I are those wherein A and B are identical and are a radical of formula X ~ ~ CONH2 CONH2 ~ ~ ~ CONH2 / ~ \
or wherein X is a direct bond or -O-.
Preferred diketopyrrolopyrrole pigments are those of formula I, wherein A and B are identical and are a radical of formula or ~ ~ CONH2.
The pigments useful in the practice of this invention can be prepared by methods analogous to standard known ones, conveniently by treating compounds of formula I, wherein Q is CN, with concentrated sulfuric acid.
Synthetic polyamides which may suitably be used in the practice of this invention are those that may typically be prepared from e-caprolactam (Perlon~, Nylon~ 6), from cn-aminoundecanoic acid (Rilsan~), from hexamethylenediamine and adipic acid (Nylon~
66), or from analogous starting materials. Also suitable are copolyamides, typically of E-caprolactam and hexamethylenediamine and adipic acid.
The eligible pigments are blended with the polyamide by known methods in solid form or in suspension, and the blend so obtained may be subjected to an intermediate drying.
It is preferred to coat the polyamides to be coloured, which are in the form of powders;
granules or chips, with the dry pigment in powder form, i.e. to blend them mechanically such that the surface of these polyamide particles is coated with a layer of pigment. The pigment is conveniently in finely divided form. Instead of using the pure pigment, it is sometimes also possible to use with advantage preparations that comprise, in addition to the pigment, a heat-stable carrier that is compatible with polyamide, preferably a calcium or magnesium salt of a higher fatty acid, typically of stearic or behenic acid, and also polyethylene, polystyrene, polyesters and, naturally, polyamides or a mixture thereof.
Such earners are disclosed, inter alia, in US patents 4 093 584 and 4 279 802, GB patent 1 398 352 and CH patent 599 322. These granular preparations can be mixed with noncoloured polyamide granulate and further processed.
The polyamide particles coated with pigment are fused and spun or otherwise shaped by known methods to films or other moulded articles such as injection moulded parts ~1282~~ ~
(engineering plastics).
The pigment can also be incorporated in the fused polyamide before the melt is distributed to the spinnerets (injection process) and the coloured polyamide is thereafter spun or shaped.
The coloured polyamide preferably contains 0.01 to 10 % by weight, preferably 0.1 to 3 %
by weight, of an eligible pyrrolopyrrole pigment of formula I.
The uniformly coloured objects so obtained are distinguished by superior fastness to light, shampooing, wet treatments, rubbing, chlorine, dry cleaning and, in particular, by superior heat-resistance, in certain cases by a high 1R remission and also by good textile properties such as tear strength and elongation or, in the case of moulded parts, by good dimensional stability.
Owing to their good distribution in the polymer melt, the pigments suitable for use in the practice of this invention are uniformly and finely distributed in the coloured material.
The invention is illustrated by the following Examples in which, unless otherwise indicated, parts are by weight.
Example 1: With stirring, 10 parts of the dry ground pigment of formula NC
CN
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid (96 %). The dark red solution that forms within 10 minutes is stirred for 16 hours at room 2)..2~?~~v', temperature and then poured onto 800 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral, suspended in 240 parts by volume of N-methylpyrrolidone and recrystallised by heating for 6 hours to 175°C while simultaneously removing water by distillation. The crystals are isolated by filtration, washed with methanol and lyophilised, giving 8.5 parts (78 % of theory) of the pigment of formula HZNOC
Analysis: C H N
calcd: 64.17% 3.77% 14.97%
found: 64.34% 3.90% 14.55%
Example 2: 10 parts of the dry ground pigment of formula CN
21~~~~~~~
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid (96 %). The dark red solution that forms within 15 minutes is stirred for 18 hours at room temperature and then poured onto 800 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral and subsequent drying gives parts (92 % of theory) of the pigment of formula ~\
~~.~~~~~~i _7_ Anal C H N
calcd: 62:66% 3.94% 14.61 %
found: 62.75% 4.39% 14.76%
Example 3: 5 parts of the dry ground pigment of formula CN
CN
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid Q96 %). The bluish-violet solution that forms within 30 minutes is stirred for 18 hours at room temperature and then poured into 400 parts by volume of ice/water. The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then ~liltered. The residue is washed with water until neutral and subsequent lyophilisation gives 4.3 parts (82 % of theory) of the pigment of formula ~'\
~~2~2~:~
_g_ Analysis: C H N
calcd: 71.76% 4.33% 10.46%
found: 71.55% 4.50% 9.99%
Example 4: 2 parts of the dry ground pigment of formula CONH~
CN
CN
are charged at room temperature to 40 parts by volume of concentrated sulfuric acid (96 %). The violet solution that forms within 30 minutes is stirred for 22 hours at zoom temperature and then poured onto 600 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral and subsequent drying gives 2.15 parts (99 % of theory) of the pigment of formula 2~~~~f:~'Y
- lo-Example 5: The pigment is synthesised as described in Example 1. The filter residue is likewise washed with water until neutral, suspended in 160 parts by volume of N-methylpyrrolidone and recrystallised by heating for 6 hours in an autoclave to 260°C.
The crystals are isolated by filtration, washed with water and dried, giving 5.5 parts (50 %
of theory) of the same pigment as in Example 1 in coarse crystalline form.
Exam~Ie 6: 975 parts of polyamide 66 (~Ultramid AS 2500 S supplied by BASF AG) are mixed dry in powder form with 25 parts of the pigment of Example 1 and the mixture is vacuum dried. The polymer so treated is fused at 280-295°C in an extruder and spun to filaments. The orange filaments have superior lightfastness.
Polyamides mass coloured with diketopyrrolop ry role pigments The present invention relates to the mass colouration of synthetic polyamides with diketopyrrolopyrrole pigments containing carbamoyl groups.
The mass colouration of synthetic polyamides makes greater demands of the colourants than the mass colouration of other plastic materials. The melting points of synthetic polyamides are very much higher and also the chemical reactivity of the fused polyamides, especially of polyamide 66, is substantially greater, so that the colourants employed must have extremely good heat stability. There are few pigments that meet these exacting demands, particularly if superior lightfastness is additionally required.
Compared with other known diketopyrrolopyrrole pigments as disclosed, inter alia, in US patents 4 415 685 and 4 579 949, the diketopyrrolopyrrole pigments containing carbamoyl groups used in the practice of this invention for colouring synthetic polyamides do not have any exceptional properties when used for colouring other plastic materials.
Surprisingly, however, it has been found that they have an unexpectedly enhanced heat stability and quite outstanding lightfastness when used for colouring synthetic polyamides.
Accordingly, the present invention relates to mass-coloured synthetic polyamide containing, as pigment, at least one diketopyrrolopyrrole pigment of formula A O
W
HN NH
O B
wherein A and B are each independently of the other a radical of formula ~~_2~2 -z-Q
(~, m X > >
m R~ R3 / ~ \ /
O , ~ O , or \ ~' N
Q
O
i wherein Q is a -CONH2 group, m is 1 or 2, Rl and R2 are each independently of the other hydrogen, Cl, Br, CH3 or C2H5, R3 is hydrogen, CH3, C2H5 or phenyl, X is a direct bond, -O-, -S-, -S02-, -CH=CH-, -CH2- or -C(CH3)2-, and Y is -O- or -S-.
particularly suitable diketopyrrolopyrrole pigments of formula I are those wherein A and B are identical and are a radical of formula X ~ ~ CONH2 CONH2 ~ ~ ~ CONH2 / ~ \
or wherein X is a direct bond or -O-.
Preferred diketopyrrolopyrrole pigments are those of formula I, wherein A and B are identical and are a radical of formula or ~ ~ CONH2.
The pigments useful in the practice of this invention can be prepared by methods analogous to standard known ones, conveniently by treating compounds of formula I, wherein Q is CN, with concentrated sulfuric acid.
Synthetic polyamides which may suitably be used in the practice of this invention are those that may typically be prepared from e-caprolactam (Perlon~, Nylon~ 6), from cn-aminoundecanoic acid (Rilsan~), from hexamethylenediamine and adipic acid (Nylon~
66), or from analogous starting materials. Also suitable are copolyamides, typically of E-caprolactam and hexamethylenediamine and adipic acid.
The eligible pigments are blended with the polyamide by known methods in solid form or in suspension, and the blend so obtained may be subjected to an intermediate drying.
It is preferred to coat the polyamides to be coloured, which are in the form of powders;
granules or chips, with the dry pigment in powder form, i.e. to blend them mechanically such that the surface of these polyamide particles is coated with a layer of pigment. The pigment is conveniently in finely divided form. Instead of using the pure pigment, it is sometimes also possible to use with advantage preparations that comprise, in addition to the pigment, a heat-stable carrier that is compatible with polyamide, preferably a calcium or magnesium salt of a higher fatty acid, typically of stearic or behenic acid, and also polyethylene, polystyrene, polyesters and, naturally, polyamides or a mixture thereof.
Such earners are disclosed, inter alia, in US patents 4 093 584 and 4 279 802, GB patent 1 398 352 and CH patent 599 322. These granular preparations can be mixed with noncoloured polyamide granulate and further processed.
The polyamide particles coated with pigment are fused and spun or otherwise shaped by known methods to films or other moulded articles such as injection moulded parts ~1282~~ ~
(engineering plastics).
The pigment can also be incorporated in the fused polyamide before the melt is distributed to the spinnerets (injection process) and the coloured polyamide is thereafter spun or shaped.
The coloured polyamide preferably contains 0.01 to 10 % by weight, preferably 0.1 to 3 %
by weight, of an eligible pyrrolopyrrole pigment of formula I.
The uniformly coloured objects so obtained are distinguished by superior fastness to light, shampooing, wet treatments, rubbing, chlorine, dry cleaning and, in particular, by superior heat-resistance, in certain cases by a high 1R remission and also by good textile properties such as tear strength and elongation or, in the case of moulded parts, by good dimensional stability.
Owing to their good distribution in the polymer melt, the pigments suitable for use in the practice of this invention are uniformly and finely distributed in the coloured material.
The invention is illustrated by the following Examples in which, unless otherwise indicated, parts are by weight.
Example 1: With stirring, 10 parts of the dry ground pigment of formula NC
CN
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid (96 %). The dark red solution that forms within 10 minutes is stirred for 16 hours at room 2)..2~?~~v', temperature and then poured onto 800 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral, suspended in 240 parts by volume of N-methylpyrrolidone and recrystallised by heating for 6 hours to 175°C while simultaneously removing water by distillation. The crystals are isolated by filtration, washed with methanol and lyophilised, giving 8.5 parts (78 % of theory) of the pigment of formula HZNOC
Analysis: C H N
calcd: 64.17% 3.77% 14.97%
found: 64.34% 3.90% 14.55%
Example 2: 10 parts of the dry ground pigment of formula CN
21~~~~~~~
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid (96 %). The dark red solution that forms within 15 minutes is stirred for 18 hours at room temperature and then poured onto 800 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral and subsequent drying gives parts (92 % of theory) of the pigment of formula ~\
~~.~~~~~~i _7_ Anal C H N
calcd: 62:66% 3.94% 14.61 %
found: 62.75% 4.39% 14.76%
Example 3: 5 parts of the dry ground pigment of formula CN
CN
are charged at room temperature to 100 parts by volume of concentrated sulfuric acid Q96 %). The bluish-violet solution that forms within 30 minutes is stirred for 18 hours at room temperature and then poured into 400 parts by volume of ice/water. The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then ~liltered. The residue is washed with water until neutral and subsequent lyophilisation gives 4.3 parts (82 % of theory) of the pigment of formula ~'\
~~2~2~:~
_g_ Analysis: C H N
calcd: 71.76% 4.33% 10.46%
found: 71.55% 4.50% 9.99%
Example 4: 2 parts of the dry ground pigment of formula CONH~
CN
CN
are charged at room temperature to 40 parts by volume of concentrated sulfuric acid (96 %). The violet solution that forms within 30 minutes is stirred for 22 hours at zoom temperature and then poured onto 600 parts by volume of ice (bulk volume). The resultant suspension is stirred with the toothed disc until the ice has completely melted and is then filtered. The residue is washed with water until neutral and subsequent drying gives 2.15 parts (99 % of theory) of the pigment of formula 2~~~~f:~'Y
- lo-Example 5: The pigment is synthesised as described in Example 1. The filter residue is likewise washed with water until neutral, suspended in 160 parts by volume of N-methylpyrrolidone and recrystallised by heating for 6 hours in an autoclave to 260°C.
The crystals are isolated by filtration, washed with water and dried, giving 5.5 parts (50 %
of theory) of the same pigment as in Example 1 in coarse crystalline form.
Exam~Ie 6: 975 parts of polyamide 66 (~Ultramid AS 2500 S supplied by BASF AG) are mixed dry in powder form with 25 parts of the pigment of Example 1 and the mixture is vacuum dried. The polymer so treated is fused at 280-295°C in an extruder and spun to filaments. The orange filaments have superior lightfastness.
Claims (3)
1. Mass-coloured synthetic polyamide containing, as pigment, at least one diketopyrrolopyrrole pigment of formula wherein A and B are each independently of the other a radical of formula wherein Q is a -CONH2 group, m is 1 or 2, R1 and R2 are each independently of the other hydrogen, Cl, Br, CH3 or C2H5, R3 is hydrogen, CH3, C2H5 or phenyl, X is a direct bond, -O-, -S-, -SO2-, -CH=CH-, -CH2- or -C(CH3)2-, and Y is -O- or -S-.
2. A polyamide according to claim 1, containing as pigment at least one diketopyrrolopyr-role pigment of formula I, wherein A and B are identical and are a radical of formula wherein X is a direct bond or -O-.
3. A polyamide according to claim 1, containing as pigment at least one diketopyrrolopyr-role pigment of formula I, wherein A and B are identical and are a radical of formula
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH218693 | 1993-07-20 | ||
| CH2186/93-1 | 1993-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2128265A1 CA2128265A1 (en) | 1995-01-21 |
| CA2128265C true CA2128265C (en) | 2004-09-14 |
Family
ID=4227904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002128265A Expired - Fee Related CA2128265C (en) | 1993-07-20 | 1994-07-18 | Polyamides mass coloured with diketopyrrolopyrrole pigments |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0635539B1 (en) |
| JP (1) | JP3445367B2 (en) |
| KR (1) | KR100314103B1 (en) |
| CA (1) | CA2128265C (en) |
| DE (1) | DE59404868D1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0787731B1 (en) * | 1996-01-30 | 2002-08-07 | Ciba SC Holding AG | Polymerizable diketopyrrolopyrroles and polymers thereof |
| ES2178136T3 (en) * | 1997-05-06 | 2002-12-16 | Ciba Sc Holding Ag | DICETOPIRROLOPIRROLES COMPOSITIONS. |
| DE10317817A1 (en) * | 2003-04-16 | 2004-11-04 | Chromeon Gmbh | Pyrrolopyrrole as a fluorescent marker for biomolecules and spherical particles |
| BRPI0713952A2 (en) | 2006-06-30 | 2012-12-04 | Ciba Holding Inc | diketopyrrolopyrrol polymers as organic semiconductors |
| CN101479272B (en) * | 2006-06-30 | 2014-11-19 | 西巴控股有限公司 | Diketopyrrolopyrrole polymers as organic semiconductors |
| CN115873250B (en) * | 2023-01-01 | 2024-04-05 | 湖南工业大学 | Black polyimide containing pyrrolopyrrole diketone structure and preparation method and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3262270D1 (en) * | 1981-03-20 | 1985-03-28 | Ciba Geigy Ag | Process for colouring highly molecular organic material and polycyclic pigments |
| US4579949A (en) * | 1982-05-17 | 1986-04-01 | Ciba-Geigy Corporation | Preparation of pyrrolo[3,4-c]pyrroles |
| US4585878A (en) * | 1983-06-29 | 1986-04-29 | Ciba-Geigy Corporation | N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles |
| ES2101826T3 (en) * | 1991-11-04 | 1997-07-16 | Chimie Ind Sa Soc Nouv | PROCEDURE FOR THE PREPARATION OF PIGMENTS, ESPECIALLY, FLUORESCENT PIGMENTS. |
-
1994
- 1994-07-12 DE DE59404868T patent/DE59404868D1/en not_active Expired - Fee Related
- 1994-07-12 EP EP94810412A patent/EP0635539B1/en not_active Expired - Lifetime
- 1994-07-18 CA CA002128265A patent/CA2128265C/en not_active Expired - Fee Related
- 1994-07-19 KR KR1019940017374A patent/KR100314103B1/en not_active IP Right Cessation
- 1994-07-20 JP JP16727594A patent/JP3445367B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2128265A1 (en) | 1995-01-21 |
| JPH0790176A (en) | 1995-04-04 |
| EP0635539A1 (en) | 1995-01-25 |
| KR950003354A (en) | 1995-02-16 |
| EP0635539B1 (en) | 1997-12-29 |
| JP3445367B2 (en) | 2003-09-08 |
| DE59404868D1 (en) | 1998-02-05 |
| KR100314103B1 (en) | 2001-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |