CN1066180C - Red organic pigment and its use - Google Patents

Red organic pigment and its use Download PDF

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Publication number
CN1066180C
CN1066180C CN97105017A CN97105017A CN1066180C CN 1066180 C CN1066180 C CN 1066180C CN 97105017 A CN97105017 A CN 97105017A CN 97105017 A CN97105017 A CN 97105017A CN 1066180 C CN1066180 C CN 1066180C
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China
Prior art keywords
pigment
och
red
eutectic
organic pigment
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Expired - Fee Related
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CN97105017A
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CN1188123A (en
Inventor
李德方
王永华
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Shenyang Research Institute of Chemical Industry Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Priority to CN97105017A priority Critical patent/CN1066180C/en
Publication of CN1188123A publication Critical patent/CN1188123A/en
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Publication of CN1066180C publication Critical patent/CN1066180C/en
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    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The present invention relates to a red organic pigment which is a eutectic body composed of a component A and a component B. In formulas, R<1>=-H,-CH3,-OCH3,-OC2H5; R<2>=-H, CH3,-OCH3,-C1,-C2H5; R<3>=-H,-OCH3C1; R<4>=-H,-NO2; R<5>=-H,-C1.

Description

Organic red pigment and uses thereof
The eutectic that the pigment that the present invention proposes is made up of (A), (B) two components is used for textile coating stamp and dyeing, (A), (B) chemical structure is:
Figure 9710501700031
Figure 9710501700032
In the formula: R 1=-H ,-CH 3, OCH 3,-OC 2H 5
R 2=-H、-CH 3、OCH 3、-CL、C 2H 5
R 3=-H、OCH 3、-Cl
R 5=-H、NO 2
R 5=-H、-Cl
C.I. pigment Red 8 is the textile coating stamp and one of the indispensable pigment variety that dyes, at present China's large usage quantity.This kind coloured light is bright-coloured, and every fastness ability is good, and it is to be formed with the apthol AS-E coupling through diazotization by large red-based g again.
Roll up the 3rd phase of nineteen ninety-five 7-13 pages or leaves according to " dyestuffs industries " 32: on July 16th, 1994, German Government has been issued second batch of consumer's goods regulations, German Government forbids producing the textiles that produces carcinogenic aromatic amine azo dye dyeing with intake energy from January 1 nineteen ninety-five, and announce that every article that contact with human body skin all can not contain can cause carcinogenic material.And the 3rd group of A I class of MAK (carcinogens) and A II class clear and definite 20 kinds of aromatic amines be that banned substance and relative pigment also belong to the forbidding scope, mention 20 kinds of dyestuff intermediates of Germany's forbidding in the report, comprising the intermediate large red-based g of synthetic C.I. pigment Red 8.
At present countries in the world active development, products of helping environment protection harmless to health all can replace pigment dyestuff C.I, the pigment variety of pigment Red 8 but still find no development and produce.
For addressing the above problem, we are based on domestic existing raw material and develop the new variety that every performance all is equal to or is better than the C.I. pigment Red 8, and title compound promptly of the present invention, this compound are the eutectic pigment of [A] and [B] two components.
In [A], [B] formula:
R 1=-H、-CH 3、-OCH 3、-OC 2H 5
R 2=-H、-CH 3、-OCH 3、-Cl、-C 2H 5
R 3=-H、-OCH 3、-Cl
R 4=-H、-NO 2
R 5=-H、-Cl
Pigment of the present invention is the eutectic of [A], [B] two components, and this eutectic once obtains in synthetic.[A], [B] two component molecular ratios are [1-99] in the eutectic: [99-1].
The preparation method of the eutectic pigment of [A] of the present invention, [B] two components is as follows:
Embodiment 1:
In 200 ml beakers, add 5.49 gram Fast Scarlet Gs
Figure 9710501700041
30 ml waters and 1.62 gram hydrochloric acid pull an oars 30 minutes, and on the rocks, water is adjusted volume to 150 milliliter, 0 ℃ of temperature, and adding 1.96, to restrain Sodium Nitrite (being made into 20% aqueous solution) terminal point Sodium Nitrites little excessive.
In 1000 ml beakers, add 100 ml waters and 2.14 gram oxychlorination sodium, stir and make its whole dissolvings, be warming up to 70-80 ℃ and add apthol AS: 2.57 gram and Naphthol AS-OLs
: 5.63 grams, continue to be warmed up to 90-100 ℃ and make its all dissolving, adjust volume to 300 milliliter, 35 ℃ of temperature are added to above-mentioned diazonium liquid in the coupling solution, terminal point diazonium liquid is inexcessive, PH=7-8, temperature 20-30 ℃ was stirred 15 minutes, added hydrochloric acid and transferred PH=2-4, be heated to 90-100 ℃, insulated and stirred 45 minutes is filtered washing, oven dry, gets powdery title pigment 12-13 gram.
Embodiment 2:
The operation of diazonium liquid formula is with embodiment 1.
The coupling solution prescription
In 1000 ml beakers, add 1000 ml waters, 2.14 gram sodium hydroxide, be warming up to 90 ℃, add apthol AS-E
5.14 gram and Naphthol AS-OL 2.80 grams make its dissolving clarification.Add ice, water and adjust volume to 300 milliliter, 35 ℃ of temperature add above-mentioned diazonium liquid in the coupling solution afterwards, and terminal point diazonium liquid is inexcessive, PH=7-8, temperature 20-30 ℃, stirred 15 minutes, add hydrochloric acid and transfer PH=3, be heated to 90 ℃-100 ℃, insulated and stirred 45 minutes is filtered, washes, is dried, and gets dry product 12-12.5 gram: yield 94-98%.
Eutectic pigment of the present invention is used for the pigment printing and the painted purposes of textiles.With the composite textile coating of making of eutectic pigment processing of the present invention, the requirement according to variant production in printing and dyeing industry is carried out stamp or dyeing with common process by usual method.
Performance comparison is as follows:
Performance index C.I. pigment Red 8 product of the present invention
Outward appearance deep red powder deep red powder
Tinting strength (%) 100 105
Coloured light standard standard
Thermotolerance (℃) 96 ℃ 140 ℃
Photostabilization (level) 5 6-7
Acid resistance (level) 55
Alkali resistance (level) 13
Oozing property of water (level) 4-5 4-5
Oil number (%) 50 ± 5 50 ± 5
Several dye well intermediates of using among the present invention have been published in the dyestuff of being edited and publishing June nineteen ninety-five by the Ministry of Chemical Industry dyestuffs industries Scientific And Technical Intelligence Center station, pigment dyestuff Chemicals handbook, as:
1. the large red-based g publication is at 158 pages
2. the Naphthol AS-OL publication is at 210 pages
3. the apthol AS-E publication is at 197 pages
4. bright red AS-BS publication is at 206 pages
5.C.I. the pigment Red 8 publication is at 1030 pages

Claims (3)

1, a kind of organic red pigment, the eutectic of forming by (A), (B) two components; (A), (B) chemical structure is:
Figure 9710501700021
In the formula: R 1=-H ,-CH 3, OCH 3,-OC 2H 5
R 2=-H、-CH 3、OCH 3、-CL、C 2H 5
R 3=-H、OCH 3、-Cl
R 4=-H、NO 2
R 5=-H、-Cl
2, organic red pigment according to claim 1, wherein the molecular ratio of (A), (B) two components is (1-99): (99-1).
3, organic red pigment according to claim 1 and 2 is used for the pigment printing or the painted purposes of textiles.
CN97105017A 1997-01-13 1997-01-13 Red organic pigment and its use Expired - Fee Related CN1066180C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN97105017A CN1066180C (en) 1997-01-13 1997-01-13 Red organic pigment and its use

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Application Number Priority Date Filing Date Title
CN97105017A CN1066180C (en) 1997-01-13 1997-01-13 Red organic pigment and its use

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CN1188123A CN1188123A (en) 1998-07-22
CN1066180C true CN1066180C (en) 2001-05-23

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1100829C (en) * 2000-03-28 2003-02-05 沈阳化工研究院 Organic red pigment and its usage
CN109439015B (en) * 2018-11-22 2020-08-14 宣城英特颜料有限公司 Permanent red pigment suitable for baking paint and preparation method thereof
CN109439014B (en) * 2018-11-22 2020-08-14 宣城英特颜料有限公司 Water-based fast bright red pigment and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1088597A (en) * 1992-12-07 1994-06-29 Basf公司 Comprise the dye mixture that has from the azoic dyestuff of the coupling component of diamino-pyridine series

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1088597A (en) * 1992-12-07 1994-06-29 Basf公司 Comprise the dye mixture that has from the azoic dyestuff of the coupling component of diamino-pyridine series

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