CN104945954B - A kind of dispersion red dye composition and dye preparations - Google Patents
A kind of dispersion red dye composition and dye preparations Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 239000001044 red dye Substances 0.000 title claims abstract description 32
- 239000000975 dye Substances 0.000 title claims abstract description 29
- 239000006185 dispersion Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims description 11
- 239000007859 condensation product Substances 0.000 claims description 9
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical group O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 3
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 claims description 2
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000000986 disperse dye Substances 0.000 abstract description 13
- 238000004043 dyeing Methods 0.000 abstract description 12
- 230000002209 hydrophobic effect Effects 0.000 abstract description 6
- 239000002657 fibrous material Substances 0.000 abstract description 4
- 238000009941 weaving Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Abstract
A kind of dispersion red dye composition and dye preparations, the dispersion red dye composition is by component A, component B and component C compositions, described component A is one or more mixtures in the compound shown in formula (I), described component B is one or more mixtures in the compound shown in formula (II), described component C is one or more mixtures in the compound shown in formula (III), based on described composition, component A weight/mass percentage composition is 20~98%, component B weight/mass percentage composition is 1~40%, component C weight/mass percentage composition is 1~40%.Described dispersive red dye product mainly includes dispersion red dye composition as claimed in claim 1 and auxiliary agent.When hydrophobic fiber material is contaminated on the disperse dye composition and dye preparations of the present invention, lifting force is good, and depth is good；By adjusting the ratio between different component, can obtain with the red dyeing and weaving thing that coloured light is gorgeous, every color fastness is excellent.
Description
(1) technical field
The present invention relates to a kind of dispersion red dye composition and dye preparations, especially a kind of suitable printing hydrophobic fiber
The red disperse dyes composition and dye preparations of material.
(2) background technology
From environment and ecological requirements, the novel high-performance of exploitation substitution anaphylaxis disperse dyes and poisonous disperse dyes
Disperse dyes have turned into inevitable.Because the speed ratio of disperse dyes new construction exploitation is slower, substantial amounts of work at present turns to
Between the application performance of dyestuff, dyestuff and in the research of the compound synergic of dyestuff and auxiliary agent.Pass through disperse dyes compound synergic
Research, new disperse dye composition is formed using specific component, makes it have excellent dyeability and fastness ability, used
The printing and dyeing of medium-to-high grade hydrophobic fiber material are particularly in hydrophobic fiber material.But in terms of existing compounding dispersive red dye,
Its lifting force and depth be not high, such as publication CN1827705, CN1861697.
(3) content of the invention
To solve the above problems, the invention provides a kind of red disperse dye composition and by the scattered dye of the red
The dye preparations that feed composition is prepared, when being dyed applied to hydrophobic fiber material, every color fastness is excellent, and is lifted
Power is good, depth is good, energy saving economy.
The technical solution adopted by the present invention is：
A kind of dispersion red dye composition, it is made up of component A, component B and component C, described component A is shown in formula (I)
Compound in one or more mixtures, described component B be formula (II) shown in compound in one or more
Mixture, described component C be formula (III) shown in compound in one or more mixtures, based on described combination
Thing, component A weight/mass percentage composition is 20~98%, and component B weight/mass percentage composition is 1~40%, component C quality percentage
Content is 1~40%,
In formula (I)：
R1For ethyl or cyanoethyl, R2For cyanoethyl, benzyl or phenethyl；
In formula (II)：
R3For ethyl or cyanoethyl, R4For cyanoethyl, benzyl or phenethyl；
In formula (III)：N is 1 or 2.
Preferably, based on described dye composite (described component A, component B and component C), component A quality percentage
Content is 40~98%, and component B weight/mass percentage composition is 1~30%, and component C weight/mass percentage composition is 1~30%.
It is more highly preferred to, based on described dye composite (described component A, component B and component C), the component A's
Weight/mass percentage composition is 50~98%, and component B weight/mass percentage composition is 1~25%, component C weight/mass percentage composition for 1~
25%.
Preferably, the component A is mixture more than one of following formula or two of which：
Preferably, the component B is mixture more than one of following formula or two of which：
Preferably, the component C is mixture more than one of following formula or two of which：
As preferable technical scheme, the component A is the compound of formula (I -1), component B be formula (II -1) and formula (II -
2) mixture, component C are the compound of formula (III -1)；Based on component A, component B and component C, the quality percentage of the component A
Content is 50~98%, and component B weight/mass percentage composition is 1~25%, and component C weight/mass percentage composition is 1~25%.
Due to the particularity of dye industry, it is difficult to also It is not necessary to which sterling is made, it will usually with some preparation process
Impurity, also allow when finished product is made in dye composite of the present invention containing a small amount of moisture and micro physical impurity.
Dispersion red dye composition of the present invention, used formula (I)~formula (III) compound, can easily be pressed
Mode well known to those skilled in the art synthesizes, and is such as prepared according to the diazotising of routine, couling process, or according to publication
JP9003352, GB1356695 are prepared with the method described in CN1036974 or similar method, can also use commercially available prod.
Dispersion red dye composition of the present invention, commercial treatment is needed applied to when dyeing, such as generally needed to be added
Auxiliary agent is disperseed, therefore present invention also offers dispersive red dye product, described dispersive red dye product mainly includes disperseing
Red dye composition and auxiliary agent, the matter of the auxiliary agent and dispersion red dye composition (component A, component B and component C gross mass)
The ratio between amount is 0.2~5:1.Dispersant, diffusant and the surfactant commonly used when described auxiliary agent is disperse dyes commercialization
Deng preferably one of following or its any several mixture：Naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl
The anionic dispersing agents such as base naphthalene sulfonic acid-formaldehyde condensation product, lignosulfonates.Specifically, naphthalene sulfonic acid-formaldehyde condensation product such as diffusant
NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalene sulfonic acid-formaldehyde condensation product
Such as dispersing agent CNF, lignosulfonates such as sodium lignin sulfonate (such as commercial dispersants Reax83A, Reax85A).It is described
Auxiliary agent be preferably the Dispersant MF of any mass ratio and the mixture of sodium lignin sulfonate.
Described dispersive red dye product is prepared by a conventional method, such as structural formula (I), (II) and (III) is represented
Compound by above-mentioned proportioning mixing after, carry out particulate with pulverizers such as sand mill or grinders in the presence of auxiliary agent, water
Change；Or the compound shown in structural formula (I), (II) and (III) with sand mill or can also be ground in the presence of auxiliary agent, water respectively
The pulverizers such as grinding machine are mixed after carrying out corpusculed processing with above-mentioned ratio.Dispersive red dye product of the present invention,
Can be with the liquid after corpusculed, emulsifiable paste state or powdery after being dried with spray drying process etc., graininess supply dyeing.
According to manufactured dispersion red dye composition of the present invention and dye preparations, common dip method, pad dyeing can be used
Method is dyed, it can also be used to direct printing.Wherein, common dip method is such as pre-processed polyester textile, is put into dye vat
Contaminated, dye finishes, and cold water wash to neutrality, squeezes out, then carries out reduction cleaning, dries；Direct printing is such as contaminated fabric
Pre-treatment, dry, setting, disperse dyes mill base is printed on printing machine, then evaporated, the dye on fabric is made using decatize mode
Expect fixation, finally wash, stentering forming.
The beneficial effects of the present invention are：Hydrophobic fibre material is contaminated on the disperse dye composition and dye preparations of the present invention
During material, lifting force is good, and depth is good；By adjusting the ratio between different component, can obtain with coloured light is gorgeous, every color fastness
Excellent red dyeing and weaving thing.
(4) embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited to this.
Embodiment 1
By the component A of 91 grams of formulas (I -1), the component B of 3 grams of formulas (II -1) and 3 grams (II -2), 3 grams of formulas (III -1) component
C, 150 grams of Dispersant MF, 30 grams of sodium lignin sulfonate (Reax85A), add 750 grams of water to stir, grinding distribution
And dry, get product, the dyestuff can be supplied to the excellent red of fabric items fastness ability.
Embodiment 2~13
According to the method described in embodiment 1, the difference is that component A, component B, component C structure and weight in table 1 are used,
200 grams of auxiliary agent (Dispersant MF is 150 grams, and sodium lignin sulfonate Reax85A is 50 grams) is added, after adding 750 grams of blendings of water, is fully stirred
Mix uniformly, slurries are made, grinding distribution is dried, and finished product, the dyestuff can be supplied to the excellent red of fabric items fastness ability.
Table 1
Comparative example 1~7
By the embodiment 1 disclosed in CN1827705A as a comparison case 1；
By the embodiment 1,4 disclosed in CN1861697A as a comparison case 2,3；
By the embodiment 1 disclosed in CN101649129A as a comparison case 4；
Dyeing Example 14
By the dyestuff of embodiment 1~13, comparative example 1~4, according to the method in GB/T2397, respectively with dyeing concentration
1.5% (C), 3% (2C), 6% (4C) carry out high-temperature pressure dyeing, assess its lifting force performance, as a result see the table below 2.
Dyeing Example 15
Disperse dyes made from weighing 2 grams of embodiment 1-13 are dispersed in 500 milliliters of water, draw 20 milliliters after with 80 milliliters
Water mixing, with acetic acid adjust pH to 4.5, be put into 4 grams of polyester textiles, be warming up to 60 DEG C, continue with about 1 DEG C/min gradient increased temperatures extremely
130 DEG C, insulation dyeing 45 minutes.Then 80 DEG C or so are cooled to and uses hot water wash 10min, drying.Can be supplied to fabric uniformly and
The good red of fastness ability.
Its washing fastness, fastness to rubbing and resistance to are determined using national standard GB/T3921, GB/T3920, GB/T5718 respectively
Sub-limation fastness, measurement result see the table below 2：
The unit of table 2：Level
Test result shows：Commercial dye made of dispersion red dye composition provided by the present invention, applied to polyester
During textile dyeing, compared to comparative example dyeing polyester fabric, (cotton staining fastness while good fastness properties are ensured
It is more excellent), performance is more prominent in terms of lifting force, and lifting force is better, when representing to dye the fabric of same weight, required dyestuff
Dosage is fewer, and economy is more preferable.
Claims (10)
- A kind of 1. dispersion red dye composition, it is characterised in that：The dispersion red dye composition is by component A, component B and component C is formed, and described component A is one or more mixtures in the compound shown in formula (I), and described component B is formula (II) one or more mixtures in the compound shown in, described component C are one in the compound shown in formula (III) Kind or a variety of mixtures, based on described composition, component A weight/mass percentage composition is 20~98%, component B quality hundred It is 1~40% to divide content, and component C weight/mass percentage composition is 1~40%,In formula (I)：R1For ethyl or cyanoethyl, R2For cyanoethyl, benzyl or phenethyl；In formula (II)：R3For ethyl or cyanoethyl, R4For cyanoethyl, benzyl or phenethyl；In formula (III)：N is 1 or 2.
- 2. dispersion red dye composition as claimed in claim 1, it is characterised in that：Based on described dye composite, component A Weight/mass percentage composition be 40~98%, component B weight/mass percentage composition is 1~30%, and component C weight/mass percentage composition is 1 ~30%.
- 3. dispersion red dye composition as claimed in claim 1, it is characterised in that：It is described based on described dye composite Component A weight/mass percentage composition is 50~98%, and component B weight/mass percentage composition is 1~25%, and component C quality percentage contains Measure as 1~25%.
- 4. the dispersion red dye composition as described in one of claims 1 to 3, it is characterised in that：The component A is one of following formula Or mixture more than two of which：
- 5. the dispersion red dye composition as described in one of claims 1 to 3, it is characterised in that：The component B is one of following formula Or mixture more than two of which：
- 6. the dispersion red dye composition as described in one of claims 1 to 3, it is characterised in that：The component C is one of following formula Or mixture more than two of which：
- 7. dispersion red dye composition as claimed in claim 1, it is characterised in that：The component A is the chemical combination of formula (I -1) Thing, component B are the mixture of formula (II -1) and formula (II -2), and component C is the compound of formula (III -1)；Based on component A, component B And component C, the component A weight/mass percentage composition are 50~98%, component B weight/mass percentage composition is 1~25%, component C Weight/mass percentage composition be 1~25%；
- 8. a kind of dispersive red dye product, described dispersive red dye product mainly includes disperse red as claimed in claim 1 Dye composite and auxiliary agent, the mass ratio of the auxiliary agent and dispersion red dye composition is 0.2~5:1.
- 9. dispersive red dye product as claimed in claim 8, it is characterised in that：Described auxiliary agent is one of following or its is any Several mixtures：It is naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic acid-formaldehyde condensation product, wooden Plain sulfonate.
- 10. dispersive red dye product as claimed in claim 9, it is characterised in that：Described auxiliary agent divides for any mass ratio Powder MF and sodium lignin sulfonate mixture.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510373185.5A CN104945954B (en) | 2015-06-26 | 2015-06-26 | A kind of dispersion red dye composition and dye preparations |
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| CN201510373185.5A CN104945954B (en) | 2015-06-26 | 2015-06-26 | A kind of dispersion red dye composition and dye preparations |
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| CN104945954A CN104945954A (en) | 2015-09-30 |
| CN104945954B true CN104945954B (en) | 2017-12-08 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105585876B (en) * | 2015-12-31 | 2018-05-25 | 浙江闰土股份有限公司 | A kind of disperse dye composition, disperse dyes and its preparation method and application |
| CN110183874A (en) * | 2019-07-11 | 2019-08-30 | 浙江双冠染料有限公司 | A kind of red disperse dyes composition |
| CN110373046B (en) * | 2019-07-24 | 2024-02-23 | 孚美科(绍兴)染料科技有限公司 | Disperse red FS150% dye composition |
| CN111117290B (en) * | 2019-12-10 | 2021-08-24 | 浙江龙盛染料化工有限公司 | Disperse red dye composition and dye product |
| CN111004524B (en) * | 2019-12-24 | 2022-08-12 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0745636B2 (en) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | Disperse dye mixture |
| JP3310471B2 (en) * | 1994-02-04 | 2002-08-05 | 日本化薬株式会社 | Red disperse dye composition and method for dyeing hydrophobic fiber material using the same |
| CN1597790A (en) * | 2004-07-01 | 2005-03-23 | 浙江龙盛集团股份有限公司 | Composite disperse red dye |
| JP4617914B2 (en) * | 2005-02-17 | 2011-01-26 | 住友化学株式会社 | Red disperse dye composition and application to hydrophobic fiber materials |
| CN100422270C (en) * | 2006-04-10 | 2008-10-01 | 浙江龙盛集团股份有限公司 | Composite disperse red dye composition |
| CN101565558B (en) * | 2009-05-05 | 2012-10-17 | 吴江市绿洲染料化工有限公司 | Environment-friendly alkali-resistant disperse red dye mixture |
| CN102153887A (en) * | 2011-02-24 | 2011-08-17 | 浙江万丰化工有限公司 | Composite of red disperse dye |
| CN103113759A (en) * | 2013-02-28 | 2013-05-22 | 绍兴县精细化工有限公司 | Red disperse dye composition, and preparation method and application thereof |
| CN104530751B (en) * | 2014-10-08 | 2017-06-13 | 浙江龙盛集团股份有限公司 | A kind of dispersed ruby dye composition |
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