CN107488358B - A kind of low temperature dyeing of wool acid dyes and preparation method thereof - Google Patents
A kind of low temperature dyeing of wool acid dyes and preparation method thereof Download PDFInfo
- Publication number
- CN107488358B CN107488358B CN201610428225.6A CN201610428225A CN107488358B CN 107488358 B CN107488358 B CN 107488358B CN 201610428225 A CN201610428225 A CN 201610428225A CN 107488358 B CN107488358 B CN 107488358B
- Authority
- CN
- China
- Prior art keywords
- dyeing
- low temperature
- wool
- dyestuff
- acid dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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
- C09B1/22—Dyes with unsubstituted amino groups
- C09B1/24—Dyes with unsubstituted amino groups sulfonated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
- D06P1/40—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes using acid dyes without azo groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
- C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
Abstract
A kind of low temperature dyeing of wool acid dyes and preparation method thereof belongs to dye chemical industry and textile printing and dyeing field the present invention relates to a kind of low temperature dyeing of wool acidity and preparation method thereof.Low temperature dyeing of wool described in the invention may be implemented to dye wool fabric at 80 DEG C with acid dyes, and have higher dyeing percentage and dyefastness.The synthesis of low temperature dyeing of wool acid dyes of the invention can be divided into two steps: (1) diamino polyetheramine is reacted with 2- chloroethyl sodium sulfonate, is obtained sodium taurocholate and is replaced mono amino polyetheramine intermediate；(2) the produced intermediate of the first step is reacted with sodium bromaminate, obtains low temperature acid dyestuff.Low temperature dyestuff of the invention is good in aqueous dissolution, and molecular weight is big, has preferable affinity and permeability to protein fibre.Protein fibre color fastness after such dyeing is good, and dye-uptake is very fast.
Description
Technical field
The invention belongs to dye chemical industries and textile printing and dyeing field, are related to a kind of low temperature dyeing of wool acid dyes and its system
Preparation Method.
Technical background
Recently as the development of application of the biotechnology in printing and dyeing and other printing and dyeing new technologies, new process, such as cold rolling
Heap technique, terylene low temperature rapid dyeing, enzyme desizing technique, biological treatment of dyeing waste water etc., the highly energy-consuming of dyeing and height
Pollution problem is slightly alleviated, but still has some traditional highly energy-consuming high pollution techniques not to be overcome, such as wool fiber
Dyeing.
Wool textile is famous with its luxurious graceful, natural style comfortable and easy to wear, and especially cashmere has " soft Huang
The good name of gold ".Wool protein fiber is mainly by scale layer (Cuticle), cortical layer (Cortex), cell film composite (Cell
Membrane Complex, CMC) and medullary substance layer (Medulla, fine wool and cashmere do not have medullary substance layer) composition.Wherein cortical layer
Decide the Main physical of wool mechanically and chemically performance, and scale layer and cell film composite then play the dyeability of wool
Conclusive effect [1].
During woolen dyed, dyestuff is adsorbed in fiber surface first, concentration gradient inside and outside fiber is formed, then to fibre
Internal penetration, diffusion and fixation are tieed up, it is to influence wool fiber dyeing temperature that wherein dyestuff, which passes through infiltration of the scale layer to fibrous inside,
The deciding step of degree and dyeing ability.There are two types of approach to diffusion inside wool fiber for dyestuff: first is that it is thin directly to pass through scale layer
Born of the same parents are to spreading inside wool；Second is that being spread by the gap between squamous cell along CMC.But due to wool scale surface layer
(Epicuticle) hydrophobicity of lipoid layer and the compactness of scale outer layer (Exocuticle) keratinization albuminous membranae hinder
Dyestuff is spread to the absorption of wool fiber and internally, and dyestuff directly passes through scale confluent monolayer cells directly to spreading very inside wool
Difficulty, therefore it is usually necessary to use the methods of high temperature and addition auxiliary agent when dyeing, to increase the swelling and unlatching of scale layer, favorably
In dyestuff by being contaminated in the diffusion of space between cells.
Higher dyeing temperature not only consumes energy greatly, increases cost, and makes wool by the effect of thermally and chemically medicament,
Cause wool yellowing, influence feel, gloss, the vividness of fiber, decline its strength, destroys the excellent natural quality of cashmere.
A kind of side that dyeing wool fibers at low temperature technique is carried out using low temperature dyeing assistant is described in patent US3112983
Method；A kind of methods for making and using same of protein fibre low temperature dyeing assistant is described in patent US5571291.Patent
A kind of method carried out using wool protective agent containing dyeability ofwool fabric is described in US5435807.
A kind of side that low temperature dyeing of wool is realized in oxidation-reduction system is described in Chinese patent CN1851113A
Method, specific implementation method are first handled wool with thiocarbamide early period in dyeing, and the later period adds hydrogen peroxide and aoxidized,
Realize the low temperature dyeing of wool；Patent CN101469518A is described a kind of to be reached with low temperature dyeing assistant for wool SY-7
To the method for low temperature dyeing of wool；A kind of utilize is described in Chinese patent CN101736614 to knit wool first with ultrasonic wave
After object is pre-processed, then the low temperature dyeing of wool may be implemented in the method for Ultrasonic Dyeing, the method；Patent
A kind of method for realizing low temperature dyeing of wool using dyeing assistant ALbegal B and LTD is described in CN103061165A；Specially
It is described in sharp CN104018368 a kind of using wool swelling agent HS-3 pretreatment wool, the rear side for carrying out low temperature dyeing of wool
Method；It is described in patent CN104195851A a kind of using isomery alcohol ether, coconut oil methyl ester polyoxyethylene ether, ethyl alcohol, cerium sulphide
Etc. the formula for the low temperature dyeing assistant for wool being formulated；It is described in patent CN105088832 a kind of using natural plants dye
Expect the new process that mordant dyeing color after low temperature is carried out to wool；A kind of low temperature dyeing assistant for wool is described in patent CN105297488A
Formula and colouring method, the main component of low temperature dyeing assistant is tallow amine polyoxyethylene ether, triethylene glycol butyl ether, second
Oxygroup fatty acid amine derivative, polyethylene glycol and hexa etc..
In conclusion there are mainly two types of the methods of progress low temperature dyeing of wool all in the above patent: first is that carrying out sheep
Hair pretreatment uses new dyeing；Second is that carrying out assisted staining using low temperature dyeing assistant.Both methods has aobvious
The defect of work.It is pre-processed using dyeing technique or wool, it is desirable that increase new equipment, while final dyeing product quality is by sheep
Hair pre-treatment influence is higher, and dyeing " primary accurate " is limited by fabric pretreatment；The addition of auxiliary agent is easy to remain in dye bath, leads
Final treatment of dyeing wastewater difficulty is caused to increase.Therefore, before a kind of low temperature dyeing of design and synthesis dyestuff has application well
Scape.
The present invention relates to one kind can be contaminated with the acid of (80 DEG C or so) of low temperature dyeing is carried out to wool and fleece fabrics
Material and preparation method thereof.
Low temperature acid dyestuff according to the present invention, molecular structure contains polyetheramine segment and taurine group simultaneously, whole
A dye molecule is good in aqueous dissolution, and dye molecule amount is larger, has preferable affinity and infiltration to protein fibre
Permeability.Protein fibre color fastness after such dyeing is good, and dye-uptake is very fast.
Summary of the invention
The low temperature acid of segment containing polyetheramine and taurine group while the object of the present invention is to provide a kind of such as following formula (D)
Property dyestuff and preparation method thereof,
Wherein: the natural number that n is 4 to 40 indicates the degree of polymerization of polyoxyethylene segment (EO)；M is 0 or 1 to 10 nature
Number indicates the degree of polymerization of polyoxypropylene segment (PO).
Specific implementation method
The preparation of segment containing polyetheramine and taurine group low temperature acid dyestuff (D) of the invention, can use well known
Method is synthesized, and synthesis process can be mainly divided into two steps.
Step 1: being carried out using polyethers containing diamino (p) and 2- chloroethyl sodium sulfonate anti-under the conditions of 80-100 DEG C
It answers, prepares taurine and replace single-ended amino-polyether amine compounds (g), reaction equation Fig. 1 is as follows:
Step 2: the product (g) that the first step is reacted, directly under the action of catalyst, then reacts with sodium bromaminate, make
The low temperature acid dyestuff (D) of standby segment containing polyetheramine and sodium taurocholate group out.Its reaction equation Fig. 2 is as follows:
Above-mentioned polyether amine compound (Huntsman) company can be stepped with Hensel or Yangzhou Chen Hua Chemical Co., Ltd. produces
ED series polyether amine product can also use other polyoxyethylene groups (EO Based) two such as ED600, ED900, ED2003
Amine compounds, specific product are exemplified below:
H2NCH2CH2(OCH2CH2)9(C3H6O)4NH2 ED600
H2NCH2CH2(OCH2CH2)12(C3H6O)6NH2 ED900
H2NCH2CH2(OCH2CH2)39(C3H6O)6NH2 ED2003
H2NCH2CH2(OCH2CH2)20NH2 PEDA20
H2NCH2CH2(OCH2CH2)25NH2 PEDA25
H2NCH2CH2(OCH2CH2)25(C3H6O)3NH2 PEDA25-3
Low form acid dyes according to the present invention can use above-mentioned proposed method production, and response situation is among the above
Narration completely.Dyestuff of the invention can be isolated with extraction-hypobaric drying method, it is also possible to which column chromatography for separation obtains, and dyestuff
Form have liquid, paste or powder.
Dyestuff according to the present invention can be used for the low temperature dyeing and stamp of the protein fibres such as wool, cashmere.
Detailed description of the invention
Fig. 1 polyetheramine is reacted with 2- chloroethyl sodium sulfonate prepares taurine substitution polyetheramine, in which: the nature that n is 4 to 40
Number, m is 0 or 1 to 10 natural number；
Fig. 2 bromamine acid is reacted with taurine substitution polyetheramine prepares low temperature acid dyestuff (D), in which: n is oneself of 4 to 40
So number, m is 0 or 1 to 10 natural number；
Fig. 3 product P1 structural formula；
Fig. 4 product P2 structural formula；
Fig. 5 product P3 structural formula；
Fig. 6 product P4 structural formula；
Fig. 7 product P5 structural formula；
Fig. 8 product P6 structural formula；
Fig. 9 product P7 structural formula；
Figure 10 product P8 structural formula；
Figure 11 product P9 structural formula；
Figure 12 product P10 structural formula；
Figure 13 product P11 structural formula；
Figure 14 product P12 structural formula；
Figure 15 is that dyestuff one bath dyeing compares figure in dyeing performance detection.
Below by the Examples detail present invention, however the present invention is not limited to following embodiments.In the following example, if
Without especially indicating, then score and percentage is by weight.The relationships of weight fraction and volume parts just as kilogram and litre
Relationship.
Amine compound reacts that prepare N- substituted taurine sodium be extremely common reaction with 2- chloroethyl sodium sulfonate, and produces
Object is pure, does not have side reaction, therefore its reaction product is not necessarily to further structural confirmation；Meanwhile bromamine acid with it is organic aminated
Closing object reaction is very common reaction, does not have other side reactions, and polyetheramine used in reaction is macromolecule chemical combination
Object, impure object, molecular weight are only an approximate range, therefore there is no further progresss for each product in following embodiment
Necessity of structural confirmation.
Embodiment 1
240 parts of polyetheramine ED600 (Yangzhou Chenhua New Materials Co., Ltd.'s production) is weighed, is dissolved in 300 parts of water,
37 parts and 2 parts of sodium carbonate of 2- chloroethyl sodium sulfonate are added while stirring, is warming up to 90 DEG C, reacts 6 hours, in reduction vaporization system
50% moisture is added 200 parts of benzyl alcohol, and excessive ED600 in extraction system is collected organic respectively with separatory funnel liquid separation
Phase and water phase.Replace polyether amine compound in water phase for sodium taurocholate, without further separation, continues to operate in next step.
Replace polyether amine compound aqueous solution to be added into reaction kettle above-mentioned sodium taurocholate, bromamine acid is added while stirring
81 parts of sodium (production of group, Donggang City), is warming up to 70 DEG C, the mixture of 0.2 part of stannous chloride and 0.2 part of ferrous sulfate is added, and continues
Stirring is warming up to 90 DEG C, keeps the temperature 6 hours.Reaction end is detected using thin-layer chromatography (TLC) contact plate.
After reacting to terminal, the water in reaction system is removed under reduced pressure, dissolves reaction mixture with ethyl alcohol, refilters away
Catalyst stannous chloride and ferrous sulfate, filtrate are evaporated under reduced pressure again, collect 215.6 parts of ethyl alcohol and product (P1), yield respectively
About 95%, products therefrom P1 is shown in into Fig. 3, is at room temperature intense blue viscous liquid materials.
Embodiment 2
90 parts of polyetheramine ED900 (Yangzhou Chenhua New Materials Co., Ltd.'s production) is weighed, is dissolved in 100 parts of water,
9.25 parts and 1 part of sodium carbonate of 2- chloroethyl sodium sulfonate are added while stirring, is warming up to 90 DEG C, reacts 6 hours, system is evaporated under reduced pressure
In 50% moisture, be added 100 parts of butanol, excessive ED900 in extraction system is collected organic respectively with separatory funnel liquid separation
Phase and water phase.Replace polyether amine compound in water phase for sodium taurocholate, without further separation, continues to operate in next step.
Replace polyether amine compound aqueous solution to be added into reaction kettle sodium taurocholate, sodium bromaminate is added while stirring
20.2 parts of (production of group, Donggang City), is warming up to 70 DEG C, the mixture of 0.05 part of stannous chloride and 0.05 part of ferrous sulfate is added,
Continue to stir, be warming up to 90 DEG C, keeps the temperature 6 hours.Reaction end is detected using thin-layer chromatography (TLC) contact plate.
After reacting to terminal, the water in reaction system is removed under reduced pressure, dissolves reaction mixture with ethyl alcohol, refilters away
Catalyst stannous chloride and ferrous sulfate, filtrate are evaporated under reduced pressure again, collect 68.4 parts of ethyl alcohol and product (P2) respectively, yield is about
95%, products therefrom P2 is shown in into Fig. 4, is at room temperature intense blue viscous liquid materials.
Embodiment 3
376 parts of polyetheramine PEDA20 are weighed, are dissolved in 100 parts of water, 2- chloroethyl sodium sulfonate 18.5 is added while stirring
Part and 1 part of sodium carbonate, be warming up to 90 DEG C, react 6 hours, 50% moisture in reduction vaporization system is added 100 parts of butanol, extraction
Excessive ED900 in system is taken, with separatory funnel liquid separation, collects organic phase and water phase respectively.Replace in water phase for sodium taurocholate
Polyether amine compound continues to operate in next step without further separation.
Replace polyether amine compound aqueous solution to be added into reaction kettle sodium taurocholate, sodium bromaminate is added while stirring
40.5 parts, 70 DEG C are warming up to, the mixture of 0.1 part of stannous chloride and 0.1 part of ferrous sulfate is added, continues to stir, is warming up to 90
DEG C, keep the temperature 6 hours.Reaction end is detected using thin-layer chromatography (TLC) contact plate.
After reacting to terminal, the water in reaction system is removed under reduced pressure, dissolves reaction mixture with ethyl alcohol, refilters away
Catalyst stannous chloride and ferrous sulfate, filtrate are evaporated under reduced pressure again, collect 132.4 parts of ethyl alcohol and product (P2), yield respectively
About 93.5%, products therefrom P3 is shown in into Fig. 5.
Preparation is containing in polyetheramine used in polyether segment and sodium taurocholate group low temperature acid dye material in embodiment 4-12
PEO, PPO content, molecular weight, (25 DEG C) final product character is as shown in table 1 at room temperature.The preparation method and reality of embodiment 4-12
Apply similar in a 1-3, final product is dark blue color substance, and product is followed successively by P4-P12 its structural formula and sees Fig. 6-Figure 14.
Table 1
To dyeing wool fabric at low temperature performance detection
(1) dyeing:
Dye dosage is 4%owf, bath raio 1: 50, with the H of 10% concentration2SO4Solution adjust Value in Dyeing Process be 5-6,25 DEG C
Wool fabric is put into dye bath, keeps the temperature 10min, after with 2 DEG C be warming up to dyeing temperature per minute, keep the temperature 10min, it is total that dye bath be added
2% anhydrous Na2SO4Promote dye, then keep the temperature 60min, take out cloth specimen, is successively washed with 80 DEG C of hot water and cold water washs.Certainly by cloth specimen
Performance detection is carried out after so drying.
(2) one bath dyeing:
The acid dyes of low temperature acid dyestuff P1, P5, P10 prepared by the present invention and traditional structure containing bromamine acid is acid
25 (Acid Blue 25) of indigo plant carry out dyeing rate curve comparison, and concrete outcome is shown in Figure 15.
(3) fastness detects:
Colour fastness to rubbing is measured by GB/T3920-1997；
Fastness to soaping reference standard GB/T3921.1-1997 measurement；
Colour fastness to perspiration GB/T3922-2013 measurement.
Through detecting, the dry and wet crock fastness after wool fabric low temperature acid dyeing as prepared by the present invention reaches 4
Grade or more, fastness to soaping reaches 4 grades, and for acid resistance perspiration fastness up to 4 grades, alkali-proof perspiration reaches 4-5 grades.
A series of present invention containing polyether segment and sodium taurocholate group low temperature dyestuff is a kind of universal dyestuff, applicable
In the low temperature dyeing of protein fibre and its blend fibre, the colouring method used when general acid dyeing by using
Method, such as dip dyeing, pad dyeing or tie dyeing dyeing.
It is according to the present invention simple containing polyether segment and sodium taurocholate group low temperature dyestuff preparation method, synthesis condition temperature
With reaction product high income.
It is only for the sake of illustration for above-described embodiment, and the interest field that the present invention is advocated should be special to apply
Subject to described in sharp range, rather than only limit above-described embodiment.
Claims (1)
1. a kind of low temperature dyeing of wool acid dyes, it is characterized in that there is the structure as shown in following formula (D),
Wherein: the natural number that n is 4 to 40 indicates the degree of polymerization of polyoxyethylene segment (EO)；M is 0 or 1 to 10 natural number,
Indicate the degree of polymerization of polyoxypropylene segment (PO).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610428225.6A CN107488358B (en) | 2016-06-13 | 2016-06-13 | A kind of low temperature dyeing of wool acid dyes and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610428225.6A CN107488358B (en) | 2016-06-13 | 2016-06-13 | A kind of low temperature dyeing of wool acid dyes and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107488358A CN107488358A (en) | 2017-12-19 |
| CN107488358B true CN107488358B (en) | 2019-05-28 |
Family
ID=60642986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610428225.6A Expired - Fee Related CN107488358B (en) | 2016-06-13 | 2016-06-13 | A kind of low temperature dyeing of wool acid dyes and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107488358B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023159566A1 (en) * | 2022-02-28 | 2023-08-31 | 杭州电子科技大学技术转移有限公司 | Method for marking hair on napped fabric |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3699135A (en) * | 1969-08-18 | 1972-10-17 | Eastman Kodak Co | Organosilicon polymeric dyes |
| US4222947A (en) * | 1978-02-17 | 1980-09-16 | Bayer Aktiengesellschaft | Anthrachinone dyestuffs |
| EP0094721A1 (en) * | 1982-05-14 | 1983-11-23 | Unilever N.V. | Synergistic preservative compositions, products containing them and processes for using them |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
-
2016
- 2016-06-13 CN CN201610428225.6A patent/CN107488358B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3699135A (en) * | 1969-08-18 | 1972-10-17 | Eastman Kodak Co | Organosilicon polymeric dyes |
| US4222947A (en) * | 1978-02-17 | 1980-09-16 | Bayer Aktiengesellschaft | Anthrachinone dyestuffs |
| EP0094721A1 (en) * | 1982-05-14 | 1983-11-23 | Unilever N.V. | Synergistic preservative compositions, products containing them and processes for using them |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107488358A (en) | 2017-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Long et al. | Dyeing of cotton fabric with a reactive disperse dye in supercritical carbon dioxide | |
| Burkinshaw et al. | Modification of cotton to improve its dyeability. Part 1—pretreating cotton with reactive polyamide‐epichlorohydrin resin | |
| CN102797170A (en) | Formaldehyde-free fixing agent and preparation method thereof | |
| CN102061611B (en) | Cold pad batch (CPB) dyeing method of pure cotton knitted fabric | |
| CN105131651B (en) | A kind of reactive navy blue is to black dye composition and dye preparations | |
| CN106835768B (en) | Application of folium artemisiae argyi pigment dye in cotton fiber after-mordant dyeing process | |
| CN102757667A (en) | Red reactive dye composition and dyeing application thereof on fiber | |
| CN107488358B (en) | A kind of low temperature dyeing of wool acid dyes and preparation method thereof | |
| CN102262033A (en) | Method for determining soybean protein composite fibers in textile | |
| CN102286219A (en) | Red active dye composition and dyeing application thereof in fibers | |
| CN102115613B (en) | Blue reactive dye composition and dyeing application to fiber material thereof | |
| CN101368008A (en) | Navy blue reactive dye composition and dyeing uses in fibrous material thereof | |
| Okonkwo et al. | Extraction of natural dyes from whitfieldia lateritia plant and its application on cotton fabric | |
| Youssef et al. | Alkaline dyeing of polyester and polyester/cotton blend fabrics using sodium edetate | |
| CN102585548B (en) | Red active dye composition | |
| Mousa | Synthesis and application of a polyfunctional bis (monochlorotriazine/sulphatoethylsulphone) reactive dye | |
| CN106433215B (en) | Red dye composition and its tint applications and method on fiber | |
| CN107164114A (en) | A kind of antifouling soaping agent of the quaternary ammonium salt of chain containing APEO and preparation method thereof | |
| CN106433213A (en) | Disperse red dye composition and dye product | |
| CN109355949A (en) | A kind of without phosphorus liquid substitute alkali and preparation method thereof | |
| CN109370255A (en) | A kind of dark color reactive dye compound and dye preparations | |
| CN102115612A (en) | Dark blue active dye composition and application thereof in dyeing fibers | |
| CN105113219B (en) | Black rice anthocyanin-based cotton fabric anti-ultraviolet finishing agent | |
| CN102115614B (en) | Navy blue reactive dye composite and dyeing application thereof to fiber | |
| Weibin et al. | Modification of silk with aminated polyepichlorohydrin to improve dyeability with reactive dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190528 |