CN104479395A - Disperse dye with high washing fastness and high light fastness and preparation method thereof - Google Patents
Disperse dye with high washing fastness and high light fastness and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a disperse dye with high washing fastness and high light fastness and preparation and application thereof. The structure of the disperse dye with high washing fastness and high light fastness is as shown in a formula (I), R1 is alkylene with a carbon number of 1-5, and R2 is methyl, ethyl, phenyl and biphenyl. The disperse dye disclosed by the invention has the advantages of high washing fastness and light fastness, no toxicity, no carcinogenicity, irritability prevention, safety, environmental friendliness, little three-waste discharge, simple synthetic process and low cost and is suitable for the demand of market development and industrialized production.
Description
Technical field
The present invention relates to dispersed dye and the preparation and application thereof of a kind of high washing fastness and high light fastness.
Background technology
The photofading phenomenon of coloured fibre is very general, and the research of people to this phenomenon continue for the time of intimate 200 years.Along with the appearance of various new dye, dyeing process and tencel, also more extensive to the research of this phenomenon.But the photofading of dyestuff is a kind of very complicated physicochemical change, be difficult to be got across by single or several reason, the mechanism of its inherence is not also very clear and definite.All the time, it is conventionally believed that the structure of dyestuff is the major cause determining its light fastness.Thus, dyeing and finishing workers more design from molecular structure of dye the light fastness that dyestuff is removed to improve in this direction.
Simultaneously, conventional dispersed dye produce solvency action to dyestuff when high temperature due to the auxiliary agent of fibrous outer, dyestuff to be widened by fiber capillary high temperature from fibrous inside and is moved to fiber sheath, dyestuff is piled up at fiber sheath, cause a series of impact, as look becomes, the phenomenons such as color fastness decreased, are presented as that dyestuff thermal migration is poor.
Although some dispersed dye increase molecular weight on molecular structure in the market, to improve resistance to thermal migration, light fastness is still not ideal enough.
Summary of the invention
For solving the problem, the invention provides dispersed dye and the preparation and application thereof of a kind of high washing fastness and high light fastness.
Dispersed dye for high washing fastness and high light fastness, structure is such as formula shown in (I)
R
1for carbonatoms is the alkyl of 1-5;
R
2for methyl, ethyl, phenyl, xenyl.
Preferably, the dispersed dye of described high washing fastness and high light fastness be following formula (I-1) to one of compound formula (I-9) Suo Shi:
The invention still further relates to the chemical preparation process of the dispersed dye of high Exposure to Sunlight, described method is as follows:
(1) compound shown in formula (II) is carried out diazotization reaction in diazo reagent and obtain diazonium salt;
In formula (II), R
1for being the alkyl of 1-5 for carbonatoms;
(2) compound shown in step (1) gained diazonium salt and formula (III) is carried out coupled reaction, obtain the dispersed dye of described high washing fastness and high light fastness;
In formula (III), R
2for methyl, ethyl, phenyl, xenyl.
Dispersed dye of the present invention can carry out doazo reaction by the mode known by those skilled in the art and obtain diazonium salt by compound shown in through type (II), then carry out coupled reaction synthesis with the compound shown in formula (III) by the mode known by those skilled in the art.
Described diazotization reaction and coupled reaction are common reactant in this area, and its popular response condition is also applicable to the preparation of dispersed dye of the present invention, adopt following reaction conditions in the present invention:
In step (1), diazo reagent is the mixing solutions of sulfuric acid and nitrosyl sulfuric acid or the mixing solutions of hydrochloric acid and Sodium Nitrite.
In step (1), diazotization reaction is carried out at-10 DEG C ~ 30 DEG C.
Coupled reaction is carried out in the sulphuric acid soln of mass concentration 0 ~ 20%, at-10 DEG C ~ 10 DEG C in step (2).
Compound shown in step (1) formula (II) is 1: 1.0 ~ 1.10 with diazo reagent amount of substance ratio.
The amount ratio of the combinations of materials shown in step (2) diazonium salt and formula (III) is 1.0 ~ 1.15: 1.
The application in dispersed dye prepared by the dispersed dye that the invention still further relates to described high washing fastness and high light fastness.
When the dispersed dye described in formula (I) are applied to dyeing, normal and auxiliary agent, water or other pulverizer such as wetting agent sand mill or shredder carry out corpusculed process.Described auxiliary agent can be usual auxiliaries that is one of following or mixing arbitrarily: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.Described naphthalene sulfonic acidformaldehyde condensation product is as dispersing agent NNO; Alkyl naphthalene sulfonic acid formaldehyde condensation products is as Dispersant MF; Sulfonated lignin are as sodium lignosulfonate (commercial dispersants Reax83A, Reax 85A) etc.
Filamentary material by dispersed dye of the present invention is not particularly limited, as long as their usual dyeable with disperse dye, but having as an example can be quoted: hydrophobic fiber material is as those are containing the material of trevira, as polyethylene terephthalate, the blending of the polycondensation product of terephthalic acid and Isosorbide-5-Nitrae-bis-(methylol) cyclohexane etc. or the synthon such as this trevira and such as nylon or mixed fabric product.
The beneficial effect of the dispersed dye of high washing fastness of the present invention and high light fastness is mainly reflected in: this dyestuff has high washing and high light fastness, and nontoxic non-carcinogenesis, hypo-allergenic, safety and environmental protection, three waste discharge is few, and synthesis technique is simple, cheap, be applicable to the needs of market development and suitability for industrialized production, dispersed dye of the present invention also have the following advantages.
1, high washing fastness.
Because the phthalic imidine structure in this dye molecule and the ester group link of soaping in dyeing course hydrolysis reaction can occur, form the hydrolysate of the band negatively charged ion such as formula (IV), formula (V) and formula (VI) three kinds of structures, these products are easily water-soluble, final performance results is that loose colour easily washes away, and the fabric fastness that wets improves greatly.
2, high light fastness.
Meanwhile, we also find, the major cause that azoic dye light fastness is not high is that energetic ray (as ultraviolet etc.) makes azo bond rupture in daylight.Pyridone structure in dispersed dye molecular structure of the present invention can form one such as formula the tautomeric structure shown in (VII) and formula (VIII) with nitrogen nitrogen double bond, stable ring texture is formed in molecule, make molecular structure exceptional stability, final body now this dyestuff has very high light fastness.
3, high sublimation fastness
We also find, the molecular structure of the dispersed dye of high washing fastness of the present invention and high light fastness exists following enol-type structure change:
Because dispersed dye are hydrophobic dyes, in order to increase the hydrophobicity of dyestuff, be there is not the hydrophilic radicals such as hydroxyl, carboxyl and sulfonic group in dye structure design.This spline structure also result in molecular association degree between dyestuff and dyestuff to be reduced, and finally affects the sublimation fastness of dyestuff.And in disperse dyes structure of the present invention, due to the existence of this enol form tautomeric structure, result in dyestuff and have the hydroxyl of some amount to exist.Hydroxyl can form hydrogen bond with the oxygen of carbonyl, and the reactive force between dyestuff and dyestuff is strengthened greatly, is macroscopically presented as that this dyestuff has very high sublimation fastness.
4, other various performances significantly improve.
In experiment, we also find, in fact, above-mentioned tautomeric structure, can be formed between molecule.And intramolecular tension force impact, more easily formed such as formula (IX) such form.Due to this structure, there is hydrogen bond action intermolecular, its reactive force has the increase of the order of magnitude than Van der Waals force, therefore, not only makes molecular structure more stable, and sunlight fastness is better, and meanwhile, fastness to sublimation also improves greatly.In sum, after intramolecular ester group, increase a carbonyl structure and have great raising to the sunlight fastness of dyestuff and fastness to sublimation.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this.
Embodiment 1:
1, the preparation of diazonium salt
The sulfuric acid that 35g concentration is 98% is added in the 250ml four-hole boiling flask stirred, control less than 50 degree and slowly add 58 grams of N-methyl-4-amino-5-bromine phthalic imidine (purity 98.0%, solid content 45%), add stirring 1 hour, be cooled to 20-25 degree and control this temperature slowly add nitrosyl sulfuric acid solution that folding hundred amount is 13.5g (folding hundred amounts refer to convert be 100% amount, the amount of the nitrosyl sulfuric acid namely contained in this solution), add and continue stirring reaction 5h in this temperature, detect in frozen water with starch potassium iodide paper, if aobvious blue stopping is stirred for subsequent use.
2, coupled reaction
In with the 2000ml large beaker stirred, add water at the bottom of 300g respectively, 15g concentration is the sodium hydroxide of 30%, 1g thionamic acid, 0.5g TX-15 emulsifying agent, stirs.Add appropriate ice and be cooled to N-(4-(2-oxopropyl) the butyric ester)-3-cyano group-4-methyl-6-hydroxyl-2-pyridone (purity 98.0%) that less than 5 DEG C add 28.6g, as shown in structure A.After stirring 0.5h, with hydrochloric acid adjustment system PH=5-6, control temperature on the rocks less than 5 degree, liquid level slowly instills the solution of the made diazonium salt of the first step, (coupling component should little over amount) be detected until reaction end with oozing circle method, the solution time for adding of diazonium salt is 2h, continues insulated and stirred 6h, is warming up to 60-65 degree and is incubated 1 hour.Suction filtration is also washed to neutrality, and obtain a kind of dispersed dye as shown in structure (I-1), dyestuff yield is more than 95%.
Embodiment 2-9
By the working method composite structure (I-2) of embodiment 1 to structure (I-9)
Embodiment 10: Dyeing Example
Respectively get high washing fastness obtained in 2 grams of embodiments 1 ~ 9 and the dispersed dye of high light fastness, be dispersed in 500 ml waters, mix with the water of 60 milliliters after drawing 20 milliliters, dye bath pH is adjusted to be 5 with acetic acid, the while of being warming up to 70 DEG C, putting into 2 grams of terylene clothes respectively and dye, in 30 minutes, be warmed up to 130 DEG C by 70 DEG C, be incubated 45 minutes, when being cooled to 90 DEG C, start sampling.Obtain 1 ~ No. 9 dyeing and weaving thing, it is water-fastness, fastness to rubbing, sun-resistant, fastness to sublimation and diffusion to adopt GB GB/T3921-1997, GB/T3920-1997, GB/T8427-1998, GB/T5718-1997 to test respectively, the results are shown in Table 1.
Comparative example 1-4: the dispersed dye respectively getting 2 grams of following structures, carries out Performance Detection according to embodiment 10 step.
Table 1: performance test results table
As can be seen from table 1 data, compared with comparative example, 9 sample detection results of the present invention improve a lot in washing fastness, light fastness and sublimation fastness.
Above-described embodiment is only for illustrating technical conceive of the present invention and feature; its object is to allow this area personage being familiar with technique can recognize content of the present invention and implement according to this; can not limit the scope of the invention with this; the equivalence change that all spirit according to the present invention are done or modification, all should be encompassed within protection scope of the present invention.
Claims (9)
1. dispersed dye for high washing fastness and high light fastness, structure is such as formula shown in (I)
R
1for carbonatoms is the alkyl of 1-5;
R
2for methyl, ethyl, phenyl, xenyl.
2. high washing fastness as claimed in claim 1 and high light fastness dispersed dye, is characterized in that: described dyestuff be following formula (I-1) to one of compound formula (I-9) Suo Shi:
3. prepare the method for high washing fastness according to claim 1 and high light fastness dispersed dye, it is characterized in that: described method comprises the steps:
(1) compound shown in formula (II) is carried out diazotization reaction in diazo reagent and obtain diazonium salt;
In formula (II), R
1for carbonatoms is the alkyl of 1-5;
(2) compound shown in step (1) gained diazonium salt and formula (III) is carried out coupled reaction, obtain described a kind of high washing fastness and the dispersed dye of high light fastness;
In formula (III), R
2for methyl, ethyl, phenyl, xenyl.
4. method as claimed in claim 3, is characterized in that: in step (1), diazo reagent is the mixing solutions of sulfuric acid and nitrosyl sulfuric acid or the mixing solutions of hydrochloric acid and Sodium Nitrite.
5. method as claimed in claim 3, is characterized in that: in step (1), diazotization reaction is carried out at-10 DEG C ~ 30 DEG C.
6. method as claimed in claim 3, is characterized in that: in step (2), coupled reaction is carried out in the sulphuric acid soln of mass concentration 0 ~ 20%, at-10 DEG C ~ 10 DEG C.
7. the method as described in one of claim 3 ~ 6, is characterized in that: the compound shown in step (1) formula (II) is 1: 1.0 ~ 1.10 with diazo reagent amount of substance ratio.
8. the method as described in one of claim 3 ~ 6, is characterized in that: the amount ratio of the combinations of materials shown in step (2) diazonium salt and formula (III) is 1.0 ~ 1.15: 1.
9. the application in dispersed dye prepared by the dispersed dye of the high washing fastness described in claim 1 or 2 and high light fastness.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105445264A (en) * | 2015-12-02 | 2016-03-30 | 浙江闰土研究院有限公司 | Quick detection method for reaction degrees in dyestuff synthesis coupling reaction |
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| CN1491259A (en) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | Phthalimidyl azo dyes, process for preparation thereof and the use thereof |
| CN1729253A (en) * | 2002-12-19 | 2006-02-01 | 西巴特殊化学品控股有限公司 | Phthalimidylazo dyes, processes for the preparation thereof and the use thereof |
| CN101981132A (en) * | 2008-03-25 | 2011-02-23 | 德司达染料德国有限公司 | Azopyridone disperse dyes, their preparation and use |
| WO2014016072A1 (en) * | 2012-07-27 | 2014-01-30 | Huntsman Advanced Materials (Switzerland) Gmbh | Disperse azo dyes, a process for the preparation thereof and the use thereof |
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2014
- 2014-11-18 CN CN201410658522.0A patent/CN104479395A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1491259A (en) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | Phthalimidyl azo dyes, process for preparation thereof and the use thereof |
| CN1729253A (en) * | 2002-12-19 | 2006-02-01 | 西巴特殊化学品控股有限公司 | Phthalimidylazo dyes, processes for the preparation thereof and the use thereof |
| CN101981132A (en) * | 2008-03-25 | 2011-02-23 | 德司达染料德国有限公司 | Azopyridone disperse dyes, their preparation and use |
| WO2014016072A1 (en) * | 2012-07-27 | 2014-01-30 | Huntsman Advanced Materials (Switzerland) Gmbh | Disperse azo dyes, a process for the preparation thereof and the use thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105445264A (en) * | 2015-12-02 | 2016-03-30 | 浙江闰土研究院有限公司 | Quick detection method for reaction degrees in dyestuff synthesis coupling reaction |
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Application publication date: 20150401 |