CN106905715B - The pigment and preparation method thereof that fades of one organic molecular species modification - Google Patents

The pigment and preparation method thereof that fades of one organic molecular species modification Download PDF

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Publication number
CN106905715B
CN106905715B CN201710115801.6A CN201710115801A CN106905715B CN 106905715 B CN106905715 B CN 106905715B CN 201710115801 A CN201710115801 A CN 201710115801A CN 106905715 B CN106905715 B CN 106905715B
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China
Prior art keywords
pigment
fades
ink
preparation
acid
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CN201710115801.6A
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CN106905715A (en
Inventor
路雯婧
宋胜梅
赵秀阳
董川
双少敏
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Shanxi Qise Environmental Protection Technology Co.,Ltd.
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Shanxi University
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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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/346—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in a substituent
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)

Abstract

The present invention provides the pigment and preparation method thereof that fades of organic molecular species modification.By organic molecule terephthalaldehydic acid and the acid dyes containing amino under the action of condensing agent, the pigment that can fade is prepared by a step condensation reaction at normal temperatures and pressures.The pigment is changed into not soluble in water, good dispersion solid pigment using organic molecule terephthalaldehydic acid cheap and easy to get as dressing agent, by water-soluble acid dyes.Its preparation flow is easy, of low cost, environmentally safe；And can sodium borohydride, sodium sulfite, the methyl sulfinate the effects that under realize that normal temperature and pressure fades.Pigment coloration prepared by the present invention is vivid, and strong coloring force can be applied to the fields such as fading ink, ink, ink for ink-jet printer, coating.

Description

The pigment and preparation method thereof that fades of one organic molecular species modification
Technical field
The present invention relates to pigment, the pigment and preparation method thereof that fades of specially organic molecular species modification.
Background technology
Ink is essential raw material in press.Ink contamination is still problem more serious in industrial sector.And The environmental issue of pigment as ink raw material also becomes the hot spot of concern at present.It is expected that ink, coating industry are used Organic pigment account for the 80% of Gross World Product, demand of the whole world to organic pigment will increase by 6.4% every year.The organic face of tradition The genotoxic potential of material and influence to ecological environment are widely studied.Therefore, from the preparation of pigment, using not With chemically or physically method be modified, improve its environmental-protecting performance, prepare energy saving, low consumption, nontoxic, pollution-free, degradable Nuisanceless pigment is applied to ink industry, environmental pollution and the energy consumption of ink is reduced with this.This gradually becomes its important development Direction.
Using the degradable pigment of novel environment friendly as research object, the key technical problem of pigment degradation is researched and solved, is increased useless Deinking is explored in the utilization of paper resource, develops the new material based on environment-friendlyink ink colorant and has great importance. This can not only alleviate the problem of shortage of resources, can also reduce the pollution to environment.Therefore, the water soluble dyestuffs of excellent are carried out Structural modification makes it be converted into the solid pigment that can be faded, and has become and has prepared one of environmental protection pigment and practicable grind Study carefully route.
Invention content
The purpose of the present invention is to provide the pigment and preparation method thereof that fades of organic molecular species modification.The pigment system Preparation Method is easy, energy conservation and environmental protection, and pigment can fade under the action of normal temperature and pressure reducing agent, is conducive to industrialized production and waste and old The deinking of ink product, recycling, recycling.
The preparation method of the pigment that fades of organic molecular species modification provided by the invention, includes the following steps：
It weighs appropriate terephthalaldehydic acid to be placed in flask, solvent n,N-Dimethylformamide (DMF) is added, condensation is added Agent, after evenly dispersed, the acid dyes containing amino is then added in stirring at normal temperature 0.1-1h, reacts at room temperature 12-30h, revolving production Object removes excess of solvent, is repeatedly washed to unreacted dyestuff and is completely removed with water, after 50-60 DEG C of vacuum drying 24-50h, obtains To target product；Wherein terephthalaldehydic acid with condensing agent, the ratio of the amount of the substance of the acid dyes containing amino be:1-2: 0.5-4:1-8。
Condensing agent used is 1- ethyls-(3- dimethylaminopropyls) carbodiimide hydrochloride (EDC) and N- hydroxyl fourths The mixture of imidodicarbonic diamide (NHS) or the mixture of dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), Or the mixture of carbodiimide hydrochloride (EDCI) and I-hydroxybenzotriazole (HOBT).
The dyestuff containing amino is methyl blue, acid fuchsin or acid green.
The pigment that fades of prepared organic molecule modification, can be in works such as sodium borohydride, methyl sulfinate, sodium sulfites It is faded under lower realization normal temperature and pressure.
The present invention has following advantageous effects：
Dressing agent of the present invention using organic molecule as water-soluble dye, is made into not soluble in water, good dispersion Solid pigment, and with the performance that can fade；Raw material sources are extensive, cheap, green non-poisonous；Preparation process is simple, item Part is mild, it is only necessary to which single step reaction can be obtained target product, and energy conservation and environmental protection is conducive to industrialized production；Pigment physics and chemistry obtained Property is stablized, pure color, strong coloring force, stores for a long time non-discolouring, and can realize and fade under normal temperature and pressure.The pigment is expected to It is applied to the fields such as writing ink, printing ink.In addition to this, waste and old ink product can be simplified using the pigment to recycle Journey makes resource recycle again, avoids the wasting of resources.
Specific implementation mode
It elaborates to the present invention with reference to embodiment, embodiment gives detailed embodiment and specific behaviour Make process, but protection scope of the present invention is not limited to following embodiments.
Embodiment 1
The preparation method of the red pigment that can fade of organic molecule modification：
It weighs 0.3g terephthalaldehydic acids to be placed in flask, 25mL n,N-Dimethylformamide (DMF) solution is added, adds Enter 0.12g EDCI and 0.1g HOBT, after evenly dispersed, 0.8783g acid fuchsins, room temperature is then added in stirring at normal temperature 40min 20h is reacted, is waited after the completion of reacting, revolving product removes excess of solvent, with the multiple washed product of water, until by unreacted dyestuff It completely removes, after 50 DEG C of vacuum drying for 24 hours, obtains target product.
Pigment obtained is red distinct, and it is colour-fast to meet water；And in pigment be added 10% sodium sulfite solution, stirring Red is taken off after 5min.
Embodiment 2
The preparation method of the blue pigment that can fade of organic molecule modification：
It weighs 0.45g terephthalaldehydic acids to be placed in flask, 35mL n,N-Dimethylformamide (DMF) solution is added, adds Enter to be added 0.23g EDC and 0.15g NHS, after evenly dispersed, 2.0g methyl blues are then added in stirring at normal temperature 30min, and room temperature is anti- It should for 24 hours wait after the completion of reacting, revolving product removes excess of solvent, with the multiple washed product of water, until unreacted dyestuff is complete Full removal obtains target product after 60 DEG C are dried in vacuo 30h.
Pigment blue obtained is distinct, and it is colour-fast to meet water；And in pigment be added 8% sodium sulfite solution, stirring Blue is taken off after 5min.
Embodiment 3
The preparation method of the green pigment that can fade of organic molecule modification：
It weighs 0.35g terephthalaldehydic acids to be placed in flask, 40mL n,N-Dimethylformamide (DMF) solution is added, adds Enter to be added 0.51g DCC and 0.015g DMAP, after evenly dispersed, 1.83g acid greens, room is then added in stirring at normal temperature 15min Temperature reaction for 24 hours, waits after the completion of reacting that revolving product removes excess of solvent, with the multiple washed product of water, until by unreacted dye Material completely removes, and after 60 DEG C of vacuum drying 35h, obtains target product.
Pigment green obtained is distinct, and chance water is colour-fast, and 5% methyl sulfinate solution is added, and color takes off after stirring 3min It goes.

Claims (5)

1. the preparation method of the pigment that fades of organic molecular species modification, which is characterized in that include the following steps：
It weighs appropriate terephthalaldehydic acid to be placed in flask, solvent n,N-Dimethylformamide (DMF) is added, condensing agent is added, After evenly dispersed, the acid dyes containing amino is then added in stirring at normal temperature 0.1-1h, reacts at room temperature 12-30h, rotates product Excess of solvent is removed, is repeatedly washed to unreacted dyestuff and is completely removed with water, after 50-60 DEG C of vacuum drying 24-50h, is obtained Target product；The ratio of the wherein amount of the substance of terephthalaldehydic acid, condensing agent and the acid dyes containing amino is:1-2:0.5- 4:1-8。
2. the preparation method of the pigment that fades of organic molecule modification as described in claim 1, which is characterized in that contracting used Mixture is mixing for 1- ethyls-(3- dimethylaminopropyls) carbodiimide hydrochloride (EDC) and N- hydroxysuccinimides (NHS) Close the mixture or carbodiimide hydrochloride of object or dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) (EDCI) and the mixture of I-hydroxybenzotriazole (HOBT).
3. the preparation method of the pigment that fades of organic molecule modification as described in claim 1, which is characterized in that described contains It is methyl blue, acid fuchsin or acid green to have the dyestuff of amino.
4. the pigment that fades that the organic molecule as made from claim 1,2 or 3 the methods is modified.
5. the pigment that fades that the organic molecule as made from claim 1,2 or 3 the methods is modified is in ink, the coating of can fading Or the application in ink.
CN201710115801.6A 2017-03-01 2017-03-01 The pigment and preparation method thereof that fades of one organic molecular species modification Active CN106905715B (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB738632A (en) * 1952-07-17 1955-10-19 May & Baker Ltd Improvements in or relating to formazans
CN101050192A (en) * 2007-05-11 2007-10-10 江南大学 Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide
CN101220214A (en) * 2008-01-25 2008-07-16 山西大学 Polymer type organic pigment and method for producing the same
CN102220047A (en) * 2011-05-12 2011-10-19 商丘师范学院 Fadable printing ink and preparation method thereof
CN103756361A (en) * 2014-01-20 2014-04-30 山西大学 Silicon-based modified fadable pigment and preparation method thereof
CN105314767A (en) * 2015-11-03 2016-02-10 兰州大学 Unsymmetrical dimethylhydrazine wastewater treatment method
CN106093379A (en) * 2016-06-08 2016-11-09 中国科学院广州生物医药与健康研究院 A kind of semicarbazides derivatization reagent and rapid detection card thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB738632A (en) * 1952-07-17 1955-10-19 May & Baker Ltd Improvements in or relating to formazans
CN101050192A (en) * 2007-05-11 2007-10-10 江南大学 Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide
CN101220214A (en) * 2008-01-25 2008-07-16 山西大学 Polymer type organic pigment and method for producing the same
CN102220047A (en) * 2011-05-12 2011-10-19 商丘师范学院 Fadable printing ink and preparation method thereof
CN103756361A (en) * 2014-01-20 2014-04-30 山西大学 Silicon-based modified fadable pigment and preparation method thereof
CN105314767A (en) * 2015-11-03 2016-02-10 兰州大学 Unsymmetrical dimethylhydrazine wastewater treatment method
CN106093379A (en) * 2016-06-08 2016-11-09 中国科学院广州生物医药与健康研究院 A kind of semicarbazides derivatization reagent and rapid detection card thereof

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Address after: 030100 zone a, workshop 2, corundum Industrial Park, Jinxiu street, Taiyuan Yangqu Park, Shanxi comprehensive reform demonstration zone, Taiyuan City, Shanxi Province

Patentee after: Shanxi Qise Environmental Protection Technology Co.,Ltd.

Address before: 030006 Taiyuan, Xiaodian District, Shanxi City Road, No. 92

Patentee before: Shanxi University

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