CN107213843B - A kind of photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant synthetic method - Google Patents
A kind of photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant synthetic method Download PDFInfo
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- CN107213843B CN107213843B CN201710397590.XA CN201710397590A CN107213843B CN 107213843 B CN107213843 B CN 107213843B CN 201710397590 A CN201710397590 A CN 201710397590A CN 107213843 B CN107213843 B CN 107213843B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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- 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
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
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- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
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Abstract
The invention discloses a kind of preparation methods of polyoxyethylene ether chain azobenzene nonionic surfactant, belong to technical field of textile chemical engineering.Using 4- hydroxyazobenzene, polyethylene glycol as a kind of polyoxyethylene ether chain azobenzene nonionic surfactant of Material synthesis.Polyoxyethylene ether chain azobenzene nonionic surfactant under ultraviolet light and radiation of visible light, can carry out it is trans- to cis- reversible isomerism, by steric hindrance change its bubble film surface alignment tightness degree, it can be achieved that low concentration, high foam stabilizing effect.It can be used as wetting infiltration, detergent and low concentration surfactant to use, solves the demand contradictory that foam dyeing and finishing front and back has different stability to foam stability, and it can be used and low foam utilization rate can be improved in some, effectively recycling foam, reduces pollution and the waste of chemical reagent.
Description
Technical field
The invention belongs to technical field of textile chemical engineering, and in particular to a kind of photoresponse straight chain azobenzene polyoxyethylene ether it is non-from
Sub- process for synthesizing surfactant.
Background technique
Traditional dyeing and finishing industry is highly water intensive, highly energy-consuming, high pollution status need to improve, can be effective using foam dyeing and finishing technology
Improvement production process in water consumption, energy consumption and pollution problem, be the potential production and processing method of tool.But foam dyeing and finishing exists
Some technical problems limit its application, and stable foam is such as needed to improve dyeing uniformity, the wave that residual foam cleans after dyeing and finishing
The pollution problem for taking and discharging can solve the above problem by novel azobenzene polyoxyethylene non-ionic surfactant.
Surfactant element is a kind of important fine chemicals, there is the title of " industrial monosodium glutamate ".Its application field is very
Extensively, surfactant is broadly divided into anionic type, cation type, amphoteric type and nonionic surfactant.Wherein
Nonionic surfactant is exactly the anion or cation that will not be dissociated into electrification in aqueous solution, and with neutral nonionic point
One kind surfactant existing for son or micelle state.In recent years, the synthesis of nonionic surfactant is closed extensively
Note, the nonionic surfactant of a series of new emerges one after another, such as polyurethane-type, multi-branched type, alkyl polyglycoside type, polyoxy second
All kinds of nonionic surfactants such as alkene phytosterol type.And for the research of azobenzene polyether nonionic surfactant compared with
It is few, so the invention patent has synthesized a kind of preparation method of polyoxyethylene ether chain azobenzene nonionic surfactant, it is novel
Azobenzene polyoxyethylene non-ionic surfactant can carry out trans- to cis- reversible under ultraviolet light and radiation of visible light
Isomery, by steric hindrance change its bubble film surface alignment tightness degree, it can be achieved that low concentration, high foam stabilizing effect
Fruit.It can be used as wetting infiltration, detergent and low concentration surfactant to use.It solves foam dyeing and finishing front and back to stablize foam
Property with different stability demand contradictory, and can be used in it is some it is low foam utilization rate can be improved, effectively recycling bubble
Foam reduces pollution and the waste of chemical reagent.
Summary of the invention
The purpose of the present invention is to provide a kind of conjunctions of photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant
At method, it is used for foam dyeing and finishing, realizes that foam stablizes the controllability of time, a kind of foam stabilizer, wetting and penetrating agent is used as before dyeing and finishing,
The effect that low concentration, high foam stabilizing can be achieved, improves the uniformity of dyeing and finishing, causes isomery by ultraviolet light after dyeing and finishing and increases it
Steric hindrance promotes residual foam rupture as a kind of defoaming agent, makes its recyclable recycling.Solves foam dyeing and finishing front and back
To foam stability have different stability demand contradictory, improve foam utilization rate, effectively recycling foam, reduce pollution and
The waste of chemical reagent；Following processing step specifically can be used in the new non-ionic surfactants:
(1) respectively by the 4- hydroxyazobenzene of 10.00~20.00wt%, 10.00~21.00wt% Anhydrous potassium carbonate and
8.00~20.00wt% potassium iodide is added in three-necked flask, and adding makes 4- hydroxyl with the tetrahydrofuran of the quality such as mixture
Azobenzene dissolution, is heated with stirring to 80 DEG C, isothermal reaction 30min；8.00~20.00wt% Bromofume is added to 20mL tetra-
Wiring solution-forming in hydrogen furans, then be slowly dropped in three-necked flask, then the agitating and heating reflux 16h at 80 DEG C, cooling
To room temperature；Acquired solution rotary evaporation removes tetrahydrofuran, is then extracted with dichloromethane, and rotary evaporation removes methylene chloride；
It is finally purified with silicagel column, is dried after taking first layer solution to rotate, obtain first step product；
(2) in order to further increase reactive grafting rate, be separately added into the product of (1) equal mass fractions sodium carbonate and
Potassium iodide is reacted with three-necked flask, and adding dissolves the product of (1) with the tetrahydrofuran of the quality such as mixture, agitating and heating
To 80 DEG C, isothermal reaction 30min；Polyethylene glycol is added to wiring solution-forming in 20ml tetrahydrofuran, then is slowly dropped to three mouthfuls
In flask then at 80 DEG C agitating and heating flow back 16h, be cooled to room temperature；Acquired solution rotary evaporation removes tetrahydrofuran, so
After be extracted with dichloromethane, rotary evaporation remove methylene chloride；After repeatedly being rinsed with the mixed liquor of petroleum ether and ethyl acetate
To the photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant of high yield and purity.
The polyethylene glycol is one of Macrogol 600, cetomacrogol 1000, polyethylene glycol 1500.
The photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant in foam dyeing and finishing application use with
Lower technique:
By 0.20-1.00wt% lauryl sodium sulfate, 0.01-0.10wt% novel azobenzene polyoxyethylene-type nonionic
Surfactant, 10.00-20.00wt% pigment printing paste, 4.00-8.00wt% adhesive and 70.90-85.79wt% deionization
Water is uniformly mixed and is configured to dye liquor, is stirred at room temperature and generates uniform and stable foam, makes partly to decline between blowing ratio 10-15
Phase is 4-6min, and the foam of generation is coated in rapidly fabric surface, and the cloth specimen through foam dyeing is placed in drying in oven,
60-80 DEG C of drying 2-5min, 150 DEG C bake 2-5min；Residual foam is vanished rapidly after ultraviolet light after dyeing, is partly declined
Phase is 1-2min, be can be recycled.
The adhesive is one of esters of acrylic acid, water-based polyurethane, organic silicon.
The ultraviolet light is iodine light source ultraviolet light.
Using the foam dyeing method of the photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant ultraviolet
The surface tension that isomerization changes bubble film is triggered under light and radiation of visible light, realizes the reversible of foam stabilizer and defoaming agent
Conversion, foam stability can be regulated and controled according to demand, it can be achieved that low concentration, high foam stabilizing effect, be conducive to improve dyeing arrange
Uniformity solves the processing problem of residual foam.
Specific embodiment
It will be helpful to further understand the present invention by embodiment below, but the contents of the present invention cannot be limited:
Embodiment 1:
(1) respectively by the 4- hydroxyazobenzene of 10.00wt%, 10.00wt% Anhydrous potassium carbonate and 8.00wt% potassium iodide
It is added in three-necked flask, adding dissolves 4- hydroxyazobenzene with the tetrahydrofuran of the quality such as mixture, is heated with stirring to
80 DEG C, 8.00wt% Bromofume is added to wiring solution-forming in 20mL tetrahydrofuran by constant temperature 30min., then is slowly added dropwise
Into three-necked flask, then the agitating and heating reflux 16h at 80 DEG C, is cooled to room temperature.Acquired solution rotary evaporation removes tetrahydro
Then furans is extracted with dichloromethane, rotary evaporation removes methylene chloride and finally purifies (silica gel: 300~400 with silicagel column
Mesh, V (petroleum ether): V (ethyl acetate)=7:1) take first layer solution rotate after dry, obtain first step product.
(2) in order to further increase reactive grafting rate, sodium carbonate and the iodate of quality such as it is separately added into the product of (1)
Potassium is reacted with three-necked flask, and adding dissolves the product of (1) with the tetrahydrofuran of the quality such as mixture, is heated with stirring to 80
DEG C, isothermal reaction 30min；Macrogol 600 is added to wiring solution-forming in 20ml tetrahydrofuran, then is slowly dropped to three mouthfuls,
In flask then at 80 DEG C agitating and heating flow back 16h, be cooled to room temperature.Acquired solution rotary evaporation removes tetrahydrofuran, so
After be extracted with dichloromethane, rotary evaporation remove methylene chloride.(V (stone is repeatedly rinsed with the mixed liquor of petroleum ether and ethyl acetate
Oily ether): product is obtained after V (ethyl acetate)=7:1).
(3) by 0.8wt% lauryl sodium sulfate, 0.2wt% polyoxyethylene ether chain azobenzene nonionic surfactant,
10.00wt% pigment printing paste, 5.00wt% acrylic ester adhesive and 85.79wt% deionized water are uniformly mixed and are configured to contaminate
Liquid is stirred at room temperature and generates uniform and stable foam, makes blowing ratio 11.2, half-life period 5.4min, by the foam of generation
It is coated in fabric surface rapidly, the cloth specimen through foam dyeing is placed in drying in oven, 60 DEG C of drying 5min, 150 DEG C bake
5min can be obtained color and uniformly dye cloth specimen.Residual foam is vanished rapidly after ultraviolet light after dyeing, and half-life period is
1.2min can be recycled.
Claims (1)
1. application of the photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant in foam dyeing and finishing uses, feature
It is, comprising the following steps:
By 0.20-1.00wt% lauryl sodium sulfate, 0.01-0.10wt% photoresponse straight chain azobenzene polyoxyethylene-type nonionic
Surfactant, 10.00-20.00wt% pigment printing paste, 4.00-8.00wt% adhesive and 70.90-85.79wt % deionization
Water is uniformly mixed and is configured to dye liquor, is stirred at room temperature and generates uniform and stable foam, makes partly to decline between blowing ratio 10-15
Phase is 4-6min, and the foam of generation is coated in rapidly fabric surface, and the cloth specimen through foam dyeing is placed in drying in oven,
60-80 DEG C of drying 2-5min, 150 DEG C bake 2-5min；Residual foam is vanished rapidly after ultraviolet light after dyeing, is partly declined
Phase is 1-2min, and foam can be recycled effectively；
The adhesive is one of esters of acrylic acid, water-based polyurethane, organic silicon；
The ultraviolet light is iodine light source ultraviolet light；
The photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant synthetic method, following processing step:
(1) respectively by the 4- hydroxyazobenzene of 10.00 ~ 20.00 wt %, 10.00 ~ 21.00 wt % Anhydrous potassium carbonates and 8.00 ~
20.00 wt % potassium iodide are added in three-necked flask, and adding makes 4- hydroxyazobenzene with the tetrahydrofuran of the quality such as mixture
Dissolution, is heated with stirring to 80 DEG C, isothermal reaction 30min；8.00 ~ 20.00wt % Bromofume is added to 20mL tetrahydrofuran
Middle wiring solution-forming, then be slowly dropped in three-necked flask, then the agitating and heating reflux 16h at 80 DEG C, is cooled to room
Temperature；Acquired solution rotary evaporation removes tetrahydrofuran, is then extracted with dichloromethane, and rotary evaporation removes methylene chloride；Finally
It is purified with silicagel column, is dried after taking first layer solution to rotate, obtain first step product；
(2) in order to further increase reactive grafting rate, the sodium carbonate and potassium iodide of quality such as it is separately added into the product of (1),
It is reacted with three-necked flask, adding dissolves the product of (1) with the tetrahydrofuran of the quality such as mixture, 80 DEG C are heated with stirring to,
Isothermal reaction 30min；Polyethylene glycol is added to wiring solution-forming in 20ml tetrahydrofuran, then is slowly dropped in three-necked flask
Then the agitating and heating reflux 16h at 80 DEG C, is cooled to room temperature；Acquired solution rotary evaporation removes tetrahydrofuran, then with two
Chloromethanes extraction, rotary evaporation remove methylene chloride；High yield is obtained after repeatedly being rinsed with the mixed liquor of petroleum ether and ethyl acetate
The photoresponse straight chain azobenzene polyoxyethylene ether nonionic surfactant of rate and purity；
The polyethylene glycol is one of Macrogol 600, cetomacrogol 1000, polyethylene glycol 1500.
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| CN108355580B (en) * | 2018-01-25 | 2020-04-10 | 西安石油大学 | Preparation method of orange surfactant |
| CN110180456B (en) * | 2019-05-16 | 2021-02-02 | 万华化学集团股份有限公司 | Multifunctional surfactant and preparation method and application thereof |
| CN110407723B (en) * | 2019-07-12 | 2021-05-11 | 江南大学 | Preparation method and application of sulfate type photoresponse foam control agent |
| CN111748323A (en) * | 2020-07-22 | 2020-10-09 | 江南大学 | Preparation method and application of optical energy storage phase change material based on azobenzene |
| CN112626885A (en) * | 2020-12-18 | 2021-04-09 | 菲诺染料化工(无锡)有限公司 | Washing-free foam printing paste and printing method |
| CN114315615A (en) * | 2021-12-07 | 2022-04-12 | 蒲城驭腾新材料科技有限公司 | Photosensitive mixed surfactant and preparation method and application thereof |
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