CN106905715A - Faded pigment of one organic molecular species modification and preparation method thereof - Google Patents

Faded pigment of one organic molecular species modification and preparation method thereof Download PDF

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Publication number
CN106905715A
CN106905715A CN201710115801.6A CN201710115801A CN106905715A CN 106905715 A CN106905715 A CN 106905715A CN 201710115801 A CN201710115801 A CN 201710115801A CN 106905715 A CN106905715 A CN 106905715A
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CN
China
Prior art keywords
pigment
ink
preparation
acid
faded
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Granted
Application number
CN201710115801.6A
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Chinese (zh)
Other versions
CN106905715B (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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Publication of CN106905715A publication Critical patent/CN106905715A/en
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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
    • 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 faded pigment of organic molecular species modification and preparation method thereof.By organic molecule terephthalaldehydic acid and the acid dyes containing amino in the presence of condensing agent, the pigment that can fade is prepared by a step condensation reaction at normal temperatures and pressures.Water miscible acid dyes is changed into water insoluble, good dispersion solid pigment by the pigment using organic molecule terephthalaldehydic acid cheap and easy to get as dressing agent.Its preparation flow is easy, with low cost, environmentally safe；And can realize that normal temperature and pressure fades under the effect such as sodium borohydride, sodium sulfite, FAS.Pigment colourity 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

Faded pigment of one organic molecular species modification and preparation method thereof
Technical field
The present invention relates to pigment, the faded pigment of specially organic molecular species modification and preparation method thereof.
Background technology
Ink is essential raw material in press.Ink contamination is still more serious problem in industrial sector.And As the environmental issue of the pigment of ink raw material, the focus of concern is also turned at present.It is expected that ink, coating industry are used Organic pigment account for the 80% of Gross World Product, the whole world will increase by 6.4% every year to the demand of organic pigment.The organic face of tradition The genotoxic potential of material and the 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-conservation, low consumption, nontoxic, pollution-free, degradable Nuisanceless pigment, is applied to ink industry, and environmental pollution and the energy consumption of ink are reduced with this.This progressively turns into its important development Direction.
With the degradable pigment of novel environment friendly as research object, the key technical problem of pigment degraded is researched and solved, increase useless The exploitation of paper resource, explore deinking, develop the new material based on environment-friendlyink ink colorant and have 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 grinds as prepare environmental protection pigment one is practicable Study carefully route.
The content of the invention
Faded pigment it is an object of the invention to provide organic molecular species modification and preparation method thereof.The pigment system Preparation Method is easy, energy-conserving and environment-protective, and pigment can fade in the presence of normal temperature and pressure reducing agent, is conducive to industrialized production and waste and old The deinking of ink product, recovery, recycling.
The preparation method of the faded pigment of the organic molecular species modification that the present invention is provided, comprises the following steps：
Weigh appropriate terephthalaldehydic acid to be placed in flask, add solvent DMF (DMF), add condensation Agent, it is dispersed after, stirring at normal temperature 0.1-1h is subsequently added the acid dyes containing amino, room temperature reaction 12-30h, and revolving is produced Thing removes excess of solvent, is repeatedly washed to unreacted dyestuff with water and removed completely, after 50-60 DEG C of vacuum drying 24-50h, obtains To target product；Wherein terephthalaldehydic acid is with the ratio of condensing agent, the amount of the material of the acid dyes containing amino: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 dicyclohexylcarbodiimide (DCC) and DMAP (DMAP) mixture, Or the mixture of carbodiimide hydrochloride (EDCI) and I-hydroxybenzotriazole (HOBT).
The described dyestuff containing amino is methyl blue, acid fuchsin or acid green.
The faded pigment of prepared organic molecule modification, can make in sodium borohydride, FAS, sodium sulfite etc. Realize being faded under normal temperature and pressure under.
The present invention has following Advantageous Effects：
The present invention is made into water insoluble, good dispersion using organic molecule as the dressing agent of water-soluble dye Solid pigment, and with the performance that can fade；Raw material sources are extensively, cheap, green non-poisonous；Preparation process is simple, bar Part is gentle, it is only necessary to which single step reaction is that can obtain target product, and energy-conserving and environment-protective are conducive to industrialized production；Obtained pigment physics and chemistry It is stable in properties, pure color, strong coloring force, long-term storage nondiscolouring, and can realize being faded under normal temperature and pressure.The pigment is expected to It is applied to the fields such as writing ink, printing-ink.In addition, waste and old ink product can be simplified using the pigment to reclaim Journey, makes resource recycle again, it is to avoid the wasting of resources.
Specific embodiment
The present invention is elaborated with reference to embodiment, embodiment gives detailed implementation method 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：
Weigh 0.3g terephthalaldehydic acids to be placed in flask, add 25mL DMF (DMF) solution, plus Enter 0.12g EDCI and 0.1g HOBT, it is dispersed after, stirring at normal temperature 40min is subsequently added 0.8783g acid fuchsins, room temperature Reaction 20h, after the completion of question response, revolving product removes excess of solvent, with the multiple washed product of water, until by unreacted dyestuff Remove completely, after 50 DEG C of vacuum drying 24h, obtain target product.
Obtained pigment is red distinct, meets water colour-fast；And in pigment add 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：
Weigh 0.45g terephthalaldehydic acids to be placed in flask, add 35mL DMF (DMF) solution, plus Enter to add 0.23g EDC and 0.15g NHS, it is dispersed after, stirring at normal temperature 30min is subsequently added 2.0g methyl blues, and room temperature is anti- 24h is answered, after the completion of question response, revolving product removes excess of solvent, with the multiple washed product of water, until unreacted dyestuff is complete Full removal, after 60 DEG C of vacuum drying 30h, obtains target product.
Obtained pigment is blue distinct, meets water colour-fast；And in pigment add 8% sodium sulfite solution, stirring Blueness is taken off after 5min.
Embodiment 3
The preparation method of the green pigment that can fade of organic molecule modification：
Weigh 0.35g terephthalaldehydic acids to be placed in flask, add 40mL DMF (DMF) solution, plus Enter to add 0.51g DCC and 0.015g DMAP, it is dispersed after, stirring at normal temperature 15min is subsequently added 1.83g acid greens, room Temperature reaction 24h, after the completion of question response, revolving product removes excess of solvent, with the multiple washed product of water, until by unreacted dye Material is removed completely, after 60 DEG C of vacuum drying 35h, obtains target product.
Obtained pigment green is distinct, and chance water is colour-fast, adds 5% FAS solution, and color takes off after stirring 3min Go.

Claims (5)

1. an organic molecular species modification faded pigment preparation method, it is characterised in that comprise the following steps：
Weigh appropriate terephthalaldehydic acid to be placed in flask, add solvent DMF (DMF), add condensing agent, After dispersed, stirring at normal temperature 0.1-1h is subsequently added the acid dyes containing amino, and room temperature reaction 12-30h rotates product Excess of solvent is removed, is repeatedly washed to unreacted dyestuff with water and removed completely, after 50-60 DEG C of vacuum drying 24-50h, obtained Target product；The ratio of the wherein amount of the material 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 faded pigment of organic molecule as claimed in claim 1 modification, it is characterised in that contracting used Mixture is mixing for 1- ethyls-(3- dimethylaminopropyls) carbodiimide hydrochloride (EDC) and N- hydroxysuccinimides (NHS) Compound, or dicyclohexylcarbodiimide (DCC) and DMAP (DMAP) mixture, or carbodiimide hydrochloride (EDCI) and I-hydroxybenzotriazole (HOBT) mixture.
3. the preparation method of the faded pigment of organic molecule as claimed in claim 1 modification, it is characterised in that described contains The dyestuff for having amino is methyl blue, acid fuchsin or acid green.
4. the faded pigment that the organic molecule as obtained in claim 1,2 or 3 methods describeds is modified.
5. the faded pigment that the organic molecule as obtained in claim 1,2 or 3 methods describeds 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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Application Number Priority Date Filing Date Title
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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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Effective date of registration: 20201201

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