CN1188123A - Red organic pigment and its use - Google Patents

Red organic pigment and its use Download PDF

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Publication number
CN1188123A
CN1188123A CN97105017A CN97105017A CN1188123A CN 1188123 A CN1188123 A CN 1188123A CN 97105017 A CN97105017 A CN 97105017A CN 97105017 A CN97105017 A CN 97105017A CN 1188123 A CN1188123 A CN 1188123A
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China
Prior art keywords
pigment
och
red
organic pigment
red organic
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Application number
CN97105017A
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Chinese (zh)
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CN1066180C (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
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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 provides a red organic pigment. Said red organic pigment is an eutectic body formed from two components of A and B.

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 mainly used in textile coating stamp and dyeing, in [A], [B] title compound:
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。
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 3 phase of nineteen ninety-five 7-13 pages or leaves according to " dyestuffs industries " 32: on July 16th, 1994, German Government was 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, every article that contact with human body skin all can not contain can cause carcinogenic material, and the 3rd group of AI class of MAK (carcinogens) and AII 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.
All active development is harmless to health in present countries in the world, helps the product of environment protection, 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:
Adding 5.49 gram Fast Scarlet G RC in 200 ml beakers (
Figure A9710501700041
), 30 ml waters and 1..62 gram hydrochloric acid pull an oar 30 minutes, and on the rocks, water is adjusted volume to 150 milliliter, 0 ℃ of temperature, 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 sodium hydroxide, stirring makes its whole dissolvings, be warming up to 70-80 ℃ and add apthol AS: 2.57 gram and Naphthol AS-OLs: 5.63 grams, continuing to be warmed up to 90-100 ℃ makes its all dissolving, adjusts volume to 300 milliliter, 35 ℃ of temperature, above-mentioned diazonium liquid is added 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 azoic coupling component
Figure A9710501700042
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, afterwards above-mentioned diazonium liquid is added in the coupling solution, terminal point diazonium liquid is inexcessive, PH=7-8, and temperature 20-30 ℃ was stirred 15 minutes, add hydrochloric acid and transfer PH=3, be heated to 90-100 ℃ of insulated and stirred 45 minutes, and filtered, wash oven dry, get finished product powdery title pigment 12-12.5 gram: rate of recovery 94-98%.
Eutectic pigment of the present invention is mainly used in textile coating stamp and dyeing.
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
Anti-cash (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. organic red pigment, the eutectic that the pigment that the present invention proposes is made up of [A], [B] two components:
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. the molecular ratio of [A], [B] two components is [1-99] in the organic red pigment according to claim 1: [99-1].
3. be mainly used in textile coating stamp and dyeing according to claim 1,2 described organic red pigments.
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

Applications Claiming Priority (1)

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

Publications (2)

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

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CN97105017A Expired - Fee Related CN1066180C (en) 1997-01-13 1997-01-13 Red organic pigment and its use

Country Status (1)

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CN (1) CN1066180C (en)

Cited By (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
CN109439015A (en) * 2018-11-22 2019-03-08 宣城英特颜料有限公司 A kind of permanent bordeaux pigment and preparation method thereof suitable for baking finish
CN109439014A (en) * 2018-11-22 2019-03-08 宣城英特颜料有限公司 A kind of aqueous everbright fast red pigment and preparation method thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59309688D1 (en) * 1992-12-07 1999-08-12 Basf Ag Dye mixtures containing azo dyes with a coupling component from the diaminopyridine series

Cited By (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
CN109439015A (en) * 2018-11-22 2019-03-08 宣城英特颜料有限公司 A kind of permanent bordeaux pigment and preparation method thereof suitable for baking finish
CN109439014A (en) * 2018-11-22 2019-03-08 宣城英特颜料有限公司 A kind of aqueous everbright fast red pigment and preparation method thereof

Also Published As

Publication number Publication date
CN1066180C (en) 2001-05-23

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