CN101914206A - Quaternized modified amino silicone oil softener and preparation and application thereof - Google Patents
Quaternized modified amino silicone oil softener and preparation and application thereof Download PDFInfo
- Publication number
- CN101914206A CN101914206A CN2010102532372A CN201010253237A CN101914206A CN 101914206 A CN101914206 A CN 101914206A CN 2010102532372 A CN2010102532372 A CN 2010102532372A CN 201010253237 A CN201010253237 A CN 201010253237A CN 101914206 A CN101914206 A CN 101914206A
- Authority
- CN
- China
- Prior art keywords
- modified amino
- silicone oil
- silicon oil
- quaternized
- softener
- 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.)
- Granted
Links
Images
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to a quaternized modified amino silicone oil softener and preparation and application thereof. The softener comprises the following general formula in the specification. The preparation comprises the following steps of: (1) adding octamethylcy-clotetrasiloxane into a container, adding a coupling agent N-beta-(aminoethyl)-gamma-aminopropyl methyl dimethoxysilane into the container dropwise, adding a tetramethyl ammonium hydroxide catalyst and subsequently a capping agent hexamethyl disiloxane into the container, and then performing reduced pressure distillation to obtain amino silicon oil; (2) dissolving the amino silicon oil into a solvent, adding the mixture into epichlorohydrin, stirring and heating to react under the protection of nitrogen, and removing the solvent by steaming to obtain an intermediate product; and (3) uniformly mixing N,N-dimethyl-decanamide and the solvent to obtain a mixture, stirring with heating, adding the intermediate product dropwise into the mixture under the protection of nitrogen, performing a thermostatic reaction, and removing the solvent by steaming to obtain the product. The softener of the invention has high hydrophilicity and high stability; fabric processed by the softener has excellent soft handfeel, high hydrophilicity, low yellowing, antibacterial property and the like; and the softener is simple to prepare and is suitable for industrial production.
Description
Technical field
The invention belongs to amino-silicone oil softening agent, its preparation and Application Areas, particularly relate to a kind of quaternized modified amino silicone oil softener, its preparation and application.
Background technology
Softening agent is the requisite after-treating auxiliary of textile printing and dyeing industry.Fabric tends to reduce its original soft feel after pre-treatment and a series of dyeing and finishing processing, behind kiering, bleaching and mercerising, owing to removed the natural fats and oils wax, feel can be than coarse before handling as cotton fabric.And, coating dye printing expanded through the steam of the heat setting type of the cotton of resination and viscose fiber, synthon, acrylic fibers and woolen shrink-proof process etc. all can produce harsh hand, use softening agent and handle and can make it recover soft feel.
Organopolysiloxane is widely used in the weaving of textile industry, dyeing and finishing, each process such as makes as softening agent, is one of natural fibre products (as cotton, fiber crops, silk, woolen knitwear etc.) and synthon goods (as polyester, polymeric amide, polyacrylonitrile etc.) high added valueization, the indispensable raw material of multifunction.Amino-silicone oil softening agent is that amido functional group is incorporated on the polysiloxane skeleton, because amino has strong polarity, can interact with groups such as hydroxyl in the fiber, carboxyls, produce extremely strong orientation and adsorptivity, therefore improved siloxanes aligning on fiber greatly, made fabric sofetening, smooth.
By having tested various amido silicon oils the effect of putting the back fabric in order is found: amido silicon oil commonly used is traditional diamine type amido silicon oil that primary amine groups, secondary amino group all have, though the good whiteness of softness, water-absorbent and easy soil release characteristics are all poor.Natural fiber after softening loses wetting ability, and effect is taken in influence; And be difficult to peel off from fabric, influence the resisdye and the Xiu Se of fabric; Exist in easy breakdown of emulsion under the processing condition such as high temperature, alkaline agent, high shear force in addition, make fabric produce phenomenons such as " oil mark " and roll banding, sticking cylinder.
Above-mentioned deficiency has seriously limited the application of amido silicon oil on high-grade fabric, for the flexibility that keeps amido organosilicon softening agent excellence, elastic feature, solves the xanthochromia phenomenon of fabric, is necessary to develop low-yellowing amino-modified silicone softening agent.
Simultaneously, along with growth in the living standard, people have higher requirement to the quality and the health level of living environment, particularly to the consciousness of health also in continuous enhancing.Therefore, the antibacterial and mouldproof processing to textile product has proposed more and higher requirement in the world wide.External antibacterial textile mould inhibitor development in recent years speed is very fast, and market trend is very good.Organosilicon quaternary ammonium salt is as the comparatively ideal antiseptic-germicide of a class over-all properties, and the fabric after the arrangement not only has good anti-microbial property, but also possesses good flexibility, suction, absorption of perspiration, smoothness, rebound resilience, static electricity resistance and resistance to crocking.
Summary of the invention
Technical problem to be solved by this invention provides a kind of quaternized modified amino silicone oil softener, its preparation and application, this softening agent has good hydrophilicity, accumulating and transportation stability, fabric after its arrangement not only has excellent soft feel, and possess hydrophilic property, low-yellowing, excellent properties such as antibiotic; The preparation method is simple, is suitable for suitability for industrialized production.
A kind of quaternized modified amino silicone oil softener of the present invention, described softening agent are connected with the quaternary ammonium salt structure of long carbochain on traditional diamine type amido silicon oil side chain, chemical structure of general formula is as follows:
R
1＝-CH
3
X=10-100 in the described softening agent structure; Y=5-50; Z=10-20;
Proterties: described quaternized modified amino silicone oil softener is the water white transparency thick liquid.
The preparation method of a kind of quaternized modified amino silicone oil softener of the present invention comprises:
(1) the octamethylcyclotetrasiloxane adding is equipped with in the container of prolong, separating funnel, thermometer and nitrogen protection device, in container, splash into coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane, 2h adds the Tetramethylammonium hydroxide catalyzer after the time, stirring is warming up to 110 ℃ of reaction 4h, add the end-capping reagent hexamethyldisiloxane afterwards, continue to be warming up to 130 ℃ of reaction 2h, be cooled to 70 ℃ of underpressure distillation again, remove low-boiling-point substance and promptly get transparent heavy-gravity amido silicon oil; The product structure general formula is seen Fig. 2;
(2) above-mentioned amido silicon oil is dissolved in the solvent, gets mixed solution; Mixed solution is splashed in the epoxy chloropropane; Adopt nitrogen protection, stir and be warming up to 30-100 ℃, reaction 2-10h; Steaming desolventizes, and obtains intermediate product; The product structure general formula is seen Fig. 3;
(3) with N, N-dimethyl amino dodecane and solvent are even, stir and are heated to 40-100 ℃ simultaneously, adopt nitrogen protection, drip above-mentioned intermediate product, isothermal reaction 5-10h, and steaming desolventizes, and obtains quaternised modified amino-silicone oil.
Octamethylcyclotetrasiloxane massfraction in the described step (1) is 85%, N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane massfraction is 4.5%, the Tetramethylammonium hydroxide massfraction is 0.1%, and the hexamethyldisiloxane massfraction is 0.05%.
Described step (1) adopts constant pressure funnel to drip coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane.
The ammonia value scope of the amido silicon oil in the described step (1) is 0.60-1.10mmol/g, and range of viscosities is 200-2000mPas.
Amido silicon oil massfraction in the described step (2) is 50-60%, and the massfraction of epoxy chloropropane is 15-20%, and the solvent quality mark is 20-40%.
Solvent in described step (2) or (3) is a Virahol.
N in the described step (3), N-dimethyl amino dodecane massfraction is 10-20%, and the intermediate product massfraction is 40-60%, and the solvent quality mark is 30-40%
The ammonia value scope of the quaternised modified amino-silicone oil in the described step (3) is 0.40-0.70mmol/g, and range of viscosities is 500-4000mPas.
The application of a kind of quaternized modified amino silicone oil softener of the present invention on cotton fabric.
Concrete steps comprise:
(1) add deionized water and organic acid mixture in quaternized modified amino silicone oil softener, stir, obtaining solid content is the modified amino silicon oil emulsion of 10%-30%; Described organic acid and softening agent mass ratio are 1: 10; Or with quaternised modified amino-silicone oil and emulsifier mix, emulsifying agent quality and softening agent mass ratio are 1: 4-5; Add water and organic acid mixture in the whipping process, organic acid and softening agent mass ratio are 1: 10, stir then, and obtaining solid content is the modified amino silicon oil emulsion of 10%-30%;
(2) technology or impregnation technology are padded in employing
Pad technology: above-mentioned modified amino silicon oil emulsion consumption is: 10-40g/L; Technical process is: fabric one soaked one rolls or two soak two and roll, and bath raio 1: 20, pick-up 70-80%, 100 ℃-120 ℃ oven dry 60-90s, 130-180 ℃ bakes 60-90s;
Impregnation technology: above-mentioned modified amino silicon oil emulsion consumption is 2-4% (owf); Technical process is: bath raio 1: 10-15, and 40-50 ℃, with textile impregnation 10-30min, dehydration, 80-100 ℃ of oven dry.
Organic acid in the described step (1) is a Glacial acetic acid; Emulsifying agent is nonionic emulsifier fatty alcohol-polyoxyethylene ether AEO-3 and AEO-9, and AEO-3 and AEO-9 mass ratio were 3.5: 6.5 or 3: 7 when emulsifying agent was composite; Gained modified amino silicon oil emulsion is transparent or milky white liquid.
The emulsion process of quaternized modified amino silicone oil softener: quaternized modified amino silicone oil softener can obtain with the direct emulsification of deionized water.Can add less during softening agent emulsification and even not add emulsifying agent.If needed, can add emulsifying agent in right amount, emulsifier type is a nonionic emulsifier.During emulsification, the mixture and the part deionized water that at first in container, add quaternised modified amino-silicone oil or itself and emulsifying agent, mix the mixture of back adding Glacial acetic acid and all the other deionized waters, high-speed stirring 20-30min, obtaining outward appearance is transparent or oyster white, and solid content is the modified amino silicon oil emulsion of 10-30%.
Research has important marketable value with quaternised modified amino-silicone oil as a kind of hydrophilic, low-yellowing and multi-functional softening agent research with germ resistance.
In order to improve the hydrophobic defective of amido silicon oil arrangement back fabric, improve its wetting ability by on side chain amino, introducing hydrophilic radical, simultaneously, also hydrophobic amido silicon oil can be converted into the silicone oil of solubility, solve the problem of the difficult emulsification of amido silicon oil, easy roll banding.
Amino in the amido silicon oil can react with different quaternizing agents, thereby obtains having the amido silicon oil of different quaternary ammonium groups.Quaternary ammonium salt-modified amino-silicone oil softening agent can be combined in fiber surface with chemical bonded refractory with the cation group of the energy that has microbe killing properties, and can fetter the freedom of movement of bacterium, suppresses its respiratory function, makes bacterium that " contact is dead " take place.
Beneficial effect
(1) quaternized modified amino silicone oil softener of the present invention suppresses because of the caused xanthochromia of amino oxidation by reducing the quantity of the reactive hydrogen on the amino in the amido silicon oil.Simultaneously, in the amido silicon oil molecule, introduce quaternary ammonium salt group, can improve the wetting ability of fabric after the amido silicon oil softening; Because its good hydrophilicity, storage and transportation stability are also fabulous, phenomenons such as breakdown of emulsion, floating oil and roll banding can not occur in the use.Quaternized modified amino silicone oil softener can keep under the prerequisite of traditional amido silicon oil feel, the xanthochromia that amido silicon oil is existed, refuses shortcomings such as water, stability of emulsion difference and significantly improves, and gives arrangement back fabric good antibacterial effect simultaneously;
(2) quaternized modified amino silicone oil softener of the present invention has very high anti-microbial property to gram prolapse of uterus and gram sun bacterium in the aqueous solution and on the fabric; Fiber had higher avidity and washing fastness preferably.
(3) preparation method of the present invention is simple, is suitable for suitability for industrialized production.
Description of drawings
The general structure of Fig. 1 quaternized modified amino silicone oil softener;
Fig. 2 amido silicon oil general structure;
Fig. 3 quaternised modified amino-silicone oil intermediate structure general formula;
Fig. 4 quaternized modified amino silicone oil softener FT-IR spectrogram.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
The adding of 300g octamethylcyclotetrasiloxane is equipped with in the four-hole boiling flask of prolong, separating funnel, thermometer, nitrogen protection device.Adopt constant pressure funnel to splash into 28g coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane in four-hole boiling flask, 1h adds 0.85g Tetramethylammonium hydroxide catalyzer after the time.Stirring adds the 0.20g hexamethyldisiloxane after being warming up to 110 ℃ of reaction 8h.After continuing reaction 1h, be warming up to 140 ℃ of decomposition catalysts.Then, be cooled to 60 ℃ of underpressure distillation, remove low-boiling-point substance and promptly get transparent heavy-gravity amido silicon oil.
Epoxy chloropropane 30g is dissolved in the 50g Virahol, adopts dropping funnel that it is splashed in the four-hole boiling flask that 100g amido silicon oil (the ammonia value is 0.907mmol/g) is housed.Adopt nitrogen protection, stir and be warming up to 50 ℃, reaction 6h.Steaming desolventizes, and obtains intermediate product, and its structural formula is seen Fig. 3.
With 15g N, N-dimethyl amino dodecane and 50g Virahol mix, and stir and are heated to 40 ℃ simultaneously.Adopt nitrogen protection, Dropwise 5 0g step 2 gained intermediate product.40 ℃ of reaction 8h, steaming desolventizes, and obtains quaternised modified amino-silicone oil, and its structural formula is seen Fig. 3, and its FT-IR spectrum is seen Fig. 4.
Embodiment 2
The adding of 300g octamethylcyclotetrasiloxane is equipped with in the four-hole boiling flask of prolong, separating funnel, thermometer, nitrogen protection device.Adopt constant pressure funnel to splash into 25g coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane in four-hole boiling flask, 1h adds 0.85g Tetramethylammonium hydroxide catalyzer after the time.Stirring adds the 0.20g hexamethyldisiloxane after being warming up to 110 ℃ of reaction 10h.After continuing reaction 1h, be warming up to 140 ℃ of decomposition catalysts.Then, be cooled to 70 ℃ of underpressure distillation, remove low-boiling-point substance and promptly get transparent heavy-gravity amido silicon oil.
Epoxy chloropropane 20g is dissolved in the 50g Virahol, adopts dropping funnel that it is splashed in the four-hole boiling flask that 100g amido silicon oil (the ammonia value is 0.907mmol/g) is housed.Adopt nitrogen protection, stir and be warming up to 100 ℃, reaction 8h.Steaming desolventizes, and obtains intermediate product, and its structural formula is seen Fig. 3.
With 10gN, N-dimethyl amino dodecane and 50g Virahol mix, and stir and are heated to 60 ℃ simultaneously.Adopt nitrogen protection, Dropwise 5 0g step 2 gained intermediate product.60 ℃ of reaction 8h, steaming desolventizes, and obtains its structural formula of quaternised modified amino-silicone oil and sees Fig. 3, and its FT-IR spectrum is seen Fig. 4.
Embodiment 3
Take by weighing the 30g quaternised modified amino-silicone oil, in container, add quaternised modified amino-silicone oil and 10g deionized water, mix the mixture of back dropping 2g Glacial acetic acid and 58g deionized water, high-speed stirring 20-30min, obtaining outward appearance is that oyster white, solid content are 30% modified amino silicon oil emulsion.
To the application of quaternized modified amino silicone oil softener, pad technology for example: quaternized modified amino silicone oil softener emulsion (30% solid content) consumption is: 20g/L; Technical process is: one soaks one rolls (pick-up 80%)---oven dry (100 ℃, 90s)---bake (150 ℃, 60s).
Arrangement finishes, wetting ability is measured with reference to AATCC Test Method 79-2000 standard, whiteness test is tested the objective ranking method of relative whiteness with reference to the GB/T8424.2-2001 textile color stability, ultimate strength and elongation at break are measured the galley proof method with reference to GB GB/T 3923-1997 textile fabric tensile property part 1, wrinkle recovery angle is measured according to AATCC 66-2008 method, concrete disposal data such as table 1.
Table 1 softening test data
Annotate: during unmodified amido silicon oil emulsification, adopt the fatty alcohol polyethenoxy ether class emulsifying agent (AEO3: AEO9=3: 7), amido silicon oil quality: emulsifying agent quality=2: 1
According to the evaluation of AATCC100-2004 textile materials antibacterial finishing agent, carry out antibacterial fabric is tested.The result shows that fabric has excellent anti-microbial property to gram prolapse of uterus (E.coli) and gram sun bacterium (S.aureus) after this softening agent arrangement, and bacteriostasis rate is more than 99%.
Claims (9)
1. quaternized modified amino silicone oil softener, described softening agent is connected with the quaternary ammonium salt structure of long carbochain on traditional diamine type amido silicon oil side chain, and chemical structure of general formula is as follows:
R
1＝-CH
3
X=10-100 in the described softening agent structure; Y=5-50; Z=10-20;
Proterties: described softening agent is the water white transparency thick liquid.
2. the preparation method of a quaternized modified amino silicone oil softener comprises:
(1) the octamethylcyclotetrasiloxane adding is equipped with in the container of prolong, separating funnel, thermometer and nitrogen protection device, in container, splash into coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane, add the Tetramethylammonium hydroxide catalyzer behind the 2h, stirring is warming up to 110 ℃ of reaction 4-10h, add the end-capping reagent hexamethyldisiloxane afterwards, continue to be warming up to 130 ℃ of reaction 2h, be cooled to 70 ℃ of underpressure distillation again, promptly get transparent heavy-gravity amido silicon oil;
(2) above-mentioned amido silicon oil is dissolved in the solvent, gets mixed solution; Mixed solution is splashed in the epoxy chloropropane; Adopt nitrogen protection, stir and be warming up to 30-100 ℃, reaction 2-10h; Steaming desolventizes, and obtains intermediate product, and its general structure is seen Fig. 3.
(3) with N, N-dimethyl amino dodecane and solvent are even, stir and are heated to 40-100 ℃ simultaneously, adopt nitrogen protection, drip above-mentioned intermediate product, isothermal reaction 5-10h, and steaming desolventizes, and obtains quaternised modified amino-silicone oil.3. the preparation method of a kind of quaternized modified amino silicone oil softener according to claim 2, it is characterized in that: the octamethylcyclotetrasiloxane massfraction is 85% in the described step (1), N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane massfraction is 4.5%, the Tetramethylammonium hydroxide massfraction is 0.1%, and the hexamethyldisiloxane massfraction is 0.05%;
The amido silicon oil massfraction is 50% in the described step (2), and the massfraction of epoxy chloropropane is 15%, and the solvent quality mark is 20%;
N in the described step (3), N-dimethyl amino dodecane massfraction is 10%, and step (2) gained intermediate product massfraction is 40%, and the solvent quality mark is 30%.
4. the preparation method of a kind of quaternized modified amino silicone oil softener according to claim 2 is characterized in that: described step (1) employing constant pressure funnel dropping coupling agent N-β-(aminoethyl)-γ-aminopropyl methyl dimethoxysilane.
5. the preparation method of a kind of quaternized modified amino silicone oil softener according to claim 2, it is characterized in that: the ammonia value scope of the amido silicon oil in the described step (1) is 0.60-1.10mmol/g, and range of viscosities is 200-2000mPas.
6. the preparation method of a kind of quaternized modified amino silicone oil softener according to claim 2, it is characterized in that: the solvent in described step (2) or (3) is a Virahol.
7. the preparation method of a kind of quaternized modified amino silicone oil softener according to claim 2, it is characterized in that: the ammonia value scope of the quaternised modified amino-silicone oil in the described step (3) is 0.40-0.70mmol/g, and range of viscosities is 500-4000mPas.
8. the application of quaternized modified amino silicone oil softener on cotton fabric.
9. the application of a kind of quaternized modified amino silicone oil softener according to claim 8 on cotton fabric, it is characterized in that: concrete steps comprise:
(1) add deionized water and organic acid mixture in quaternized modified amino silicone oil softener, stir, obtaining solid content is the modified amino silicon oil emulsion of 10%-30%; Described organic acid and softening agent mass ratio are 1: 10;
Or with quaternised modified amino-silicone oil and emulsifier mix, emulsifying agent quality and softening agent mass ratio are 1: 4-5; Add water and organic acid mixture in the whipping process, organic acid and softening agent mass ratio are 1: 10, stir then, and obtaining solid content is the modified amino silicon oil emulsion of 10%-30%;
(2) technology or impregnation technology are padded in employing
Pad technology: above-mentioned modified amino silicon oil emulsion consumption is: 10-40g/L; Technical process is: fabric one soaked one rolls or two soak two and roll, and bath raio 1: 20, pick-up 70-80%, 100 ℃-120 ℃ oven dry 60-90s, 130-180 ℃ bakes 60-90s;
Impregnation technology: above-mentioned modified amino silicon oil emulsion consumption is: 2-4%owf; Technical process is: bath raio 1: 10-15, and 40-50 ℃, with textile impregnation 10min, dehydration, 80-100 ℃ of oven dry.
10. the application of a kind of quaternized modified amino silicone oil softener according to claim 9 on cotton fabric is characterized in that: the organic acid in the described step (1) is a Glacial acetic acid; Emulsifying agent is nonionic emulsifier fatty alcohol-polyoxyethylene ether AEO-3 and AEO-9, and AEO-3 and AEO-9 mass ratio were 3.5: 6.5 or 3: 7 when emulsifying agent was composite; Gained modified amino silicon oil emulsion is transparent or milky white liquid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010253237 CN101914206B (en) | 2010-08-13 | 2010-08-13 | Quaternized modified amino silicone oil softener and preparation and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010253237 CN101914206B (en) | 2010-08-13 | 2010-08-13 | Quaternized modified amino silicone oil softener and preparation and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101914206A true CN101914206A (en) | 2010-12-15 |
| CN101914206B CN101914206B (en) | 2013-10-09 |
Family
ID=43321867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010253237 Expired - Fee Related CN101914206B (en) | 2010-08-13 | 2010-08-13 | Quaternized modified amino silicone oil softener and preparation and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101914206B (en) |
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102505495A (en) * | 2011-11-10 | 2012-06-20 | 浙江传化股份有限公司 | High-elastic smooth silicon softener and preparation method and application thereof |
| CN102505494A (en) * | 2011-11-09 | 2012-06-20 | 苏州大学 | Silver-loaded antibacterial amino silicone oil fabric finishing agent and preparation method thereof |
| CN102634977A (en) * | 2012-04-24 | 2012-08-15 | 南通大学 | Method for preparing anti-bacterial fibers and fabrics by in-situ complexometry |
| CN102775613A (en) * | 2012-08-10 | 2012-11-14 | 广州天赐高新材料股份有限公司 | Method for preparing alpha, omega-bis(aminopropyl)polydimethylsiloxane |
| CN103193984A (en) * | 2012-01-04 | 2013-07-10 | 安徽科光新材料有限公司 | Hydrophilic aminosilicon oil, and preparation method and uses thereof |
| CN103437190A (en) * | 2013-08-29 | 2013-12-11 | 华南理工大学 | Amino-silicone oil softener containing fluorine group and quaternary ammonium salt group as well as preparation method and application thereof |
| CN103897193A (en) * | 2012-12-28 | 2014-07-02 | 江南大学 | Preparation method for glycidyl mono-substituted double-amino-end end-capping reagent |
| CN104060471A (en) * | 2014-06-19 | 2014-09-24 | 宁波市川宁环保科技有限公司 | Softener composition and application of composition |
| CN104562712A (en) * | 2014-12-18 | 2015-04-29 | 西安工程大学 | Preparation method of organosilicone multicopolymer fabric softener |
| CN104562651A (en) * | 2015-01-27 | 2015-04-29 | 江苏紫石化工科技有限公司 | Fabric softener |
| CN104761723A (en) * | 2015-04-09 | 2015-07-08 | 南丰县大信科技有限公司 | Polysiloxane softening agent with color fixing property |
| CN105111448A (en) * | 2015-09-30 | 2015-12-02 | 山东巨业精细化工有限公司 | Novel silicon-containing softening agent and preparation method thereof |
| CN105297427A (en) * | 2015-10-23 | 2016-02-03 | 威海新元化工有限公司 | Compound for improving heat resistance of amino-modified silicone oil carbon fiber oil formulation and preparation and application thereof |
| CN105484101A (en) * | 2015-11-20 | 2016-04-13 | 陕西科技大学 | Preparation method for inorganic fiber softening agent, and modification method for improving softness of inorganic fiber by using inorganic fiber softening agent |
| CN105601933A (en) * | 2016-01-30 | 2016-05-25 | 青岛科技大学 | Preparation method of silicone rubber surface hydrophilic coating |
| CN105603733A (en) * | 2016-02-26 | 2016-05-25 | 苏州三和开泰花线织造有限公司 | Biodegradable textile fabric softening agent and preparation method thereof |
| CN105622944A (en) * | 2016-03-30 | 2016-06-01 | 科凯精细化工（上海）有限公司 | Quaternized organic silicone oil and preparation method thereof |
| CN105755837A (en) * | 2016-02-29 | 2016-07-13 | 苏州印丝特纺织数码科技有限公司 | Preparation method and application of quaternization modified amino silicon oil softener |
| CN105839415A (en) * | 2016-04-18 | 2016-08-10 | 广东湛丰精细化工有限公司 | Low-yellowing hydrophilic finishing agent and preparation method thereof |
| CN106192418A (en) * | 2016-07-13 | 2016-12-07 | 张静 | A kind of preparation method of milk fibre modified amino silicon oil anti pilling softener |
| CN106589385A (en) * | 2017-01-05 | 2017-04-26 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof |
| CN108252104A (en) * | 2017-12-23 | 2018-07-06 | 董晓 | A kind of preparation method for smooth agent of weaving |
| CN108797129A (en) * | 2018-06-21 | 2018-11-13 | 湖北健客日化有限公司 | A kind of fabric softening agent |
| CN109162091A (en) * | 2018-08-29 | 2019-01-08 | 华南理工大学 | A method of super-hydrophobic antibiotic fabric is prepared based on quaternized silica |
| CN109267355A (en) * | 2018-09-27 | 2019-01-25 | 佛山九陌科技信息咨询有限公司 | A kind of preparation method of silicone oil softener |
| CN109322154A (en) * | 2018-11-07 | 2019-02-12 | 青岛奥洛思新材料有限公司 | It is a kind of for handling the lubricant and preparation method thereof of crudefiber crop rove |
| CN110004726A (en) * | 2019-05-07 | 2019-07-12 | 纤化（上海）生物化工股份有限公司 | A kind of guarantor's bullet block silicone oil and preparation method thereof for elastic force cowboy |
| CN110258112A (en) * | 2019-07-15 | 2019-09-20 | 江苏盛世海新材料科技有限公司 | A kind of high-performance flexible agent |
| CN110885445A (en) * | 2019-11-01 | 2020-03-17 | 湖州美伦纺织助剂有限公司 | Novel quaternary ammonium salt modified silicone oil and production process thereof |
| CN111434852A (en) * | 2019-01-11 | 2020-07-21 | 浙江迎丰科技股份有限公司 | Short-process dyeing and finishing process for polyester-cotton blended fabric |
| CN114277579A (en) * | 2021-12-28 | 2022-04-05 | 浙江东进新材料有限公司 | Processing method of sun-proof polyester cotton-like fabric |
| CN114575167A (en) * | 2022-02-23 | 2022-06-03 | 常熟理工学院 | Preparation method of radiation-proof fabric coating |
| CN115538195A (en) * | 2022-09-30 | 2022-12-30 | 浙江越新印染有限公司 | Color fixing finishing method and application thereof in pure cotton printing and dyeing |
| CN116575165A (en) * | 2023-05-17 | 2023-08-11 | 江苏鸿鹏服饰有限公司 | Skin-friendly antibacterial sleeping bag fabric and preparation method thereof |
| CN117143345A (en) * | 2023-09-28 | 2023-12-01 | 广东宏昊化工有限公司 | Bio-based fixation softener, preparation method and application thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106012546B (en) * | 2016-05-23 | 2018-06-01 | 上海大学 | The quaternized Organic fluoride silicone oil of cationic increases deep finishing agent, its preparation method and application |
| CN106351016B (en) * | 2016-09-10 | 2018-07-10 | 上海大学 | A kind of epoxy group organic fluorinated silicone fat liquor increases deep finishing agent and preparation method thereof |
| CN106436327B (en) * | 2016-09-10 | 2018-06-01 | 上海大学 | A kind of modified amido organic fluorinated silicone fat liquor increases deep finishing agent and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1575311A (en) * | 2001-10-24 | 2005-02-02 | 陶氏康宁公司 | Silicon based quaternary ammonium functional compositions and methods for making them |
| CN101367941A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | Synthesis of epoxy quaternised modified amino-silicone oil |
-
2010
- 2010-08-13 CN CN 201010253237 patent/CN101914206B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1575311A (en) * | 2001-10-24 | 2005-02-02 | 陶氏康宁公司 | Silicon based quaternary ammonium functional compositions and methods for making them |
| CN101367941A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | Synthesis of epoxy quaternised modified amino-silicone oil |
Cited By (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102505494B (en) * | 2011-11-09 | 2013-06-12 | 苏州大学 | Silver-loaded antibacterial amino silicone oil fabric finishing agent and preparation method thereof |
| CN102505494A (en) * | 2011-11-09 | 2012-06-20 | 苏州大学 | Silver-loaded antibacterial amino silicone oil fabric finishing agent and preparation method thereof |
| CN102505495A (en) * | 2011-11-10 | 2012-06-20 | 浙江传化股份有限公司 | High-elastic smooth silicon softener and preparation method and application thereof |
| CN102505495B (en) * | 2011-11-10 | 2014-01-01 | 浙江传化股份有限公司 | High-elastic smooth silicon softener and preparation method and application thereof |
| CN103193984A (en) * | 2012-01-04 | 2013-07-10 | 安徽科光新材料有限公司 | Hydrophilic aminosilicon oil, and preparation method and uses thereof |
| CN102634977B (en) * | 2012-04-24 | 2013-06-05 | 南通大学 | Method for preparing anti-bacterial fibers and fabrics by in-situ complexometry |
| CN102634977A (en) * | 2012-04-24 | 2012-08-15 | 南通大学 | Method for preparing anti-bacterial fibers and fabrics by in-situ complexometry |
| CN102775613A (en) * | 2012-08-10 | 2012-11-14 | 广州天赐高新材料股份有限公司 | Method for preparing alpha, omega-bis(aminopropyl)polydimethylsiloxane |
| CN103897193A (en) * | 2012-12-28 | 2014-07-02 | 江南大学 | Preparation method for glycidyl mono-substituted double-amino-end end-capping reagent |
| CN103897193B (en) * | 2012-12-28 | 2016-08-10 | 江南大学 | A kind of preparation method of glycidyl mono-substituted double-end amino end-capping reagent |
| CN103437190A (en) * | 2013-08-29 | 2013-12-11 | 华南理工大学 | Amino-silicone oil softener containing fluorine group and quaternary ammonium salt group as well as preparation method and application thereof |
| CN103437190B (en) * | 2013-08-29 | 2015-07-01 | 华南理工大学 | Amino-silicone oil softener containing fluorine group and quaternary ammonium salt group as well as preparation method and application thereof |
| CN104060471A (en) * | 2014-06-19 | 2014-09-24 | 宁波市川宁环保科技有限公司 | Softener composition and application of composition |
| CN104562712A (en) * | 2014-12-18 | 2015-04-29 | 西安工程大学 | Preparation method of organosilicone multicopolymer fabric softener |
| CN104562651A (en) * | 2015-01-27 | 2015-04-29 | 江苏紫石化工科技有限公司 | Fabric softener |
| CN104761723B (en) * | 2015-04-09 | 2018-04-06 | 南丰县大信科技有限公司 | A kind of polysiloxane soft agent with fixing property |
| CN104761723A (en) * | 2015-04-09 | 2015-07-08 | 南丰县大信科技有限公司 | Polysiloxane softening agent with color fixing property |
| CN105111448A (en) * | 2015-09-30 | 2015-12-02 | 山东巨业精细化工有限公司 | Novel silicon-containing softening agent and preparation method thereof |
| CN105111448B (en) * | 2015-09-30 | 2017-10-03 | 山东巨业精细化工有限公司 | A kind of novel siliceous softening agent and preparation method thereof |
| CN105297427B (en) * | 2015-10-23 | 2017-07-04 | 威海新元化工有限公司 | A kind of compound for improving amino-modified silicone oil based carbon fiber finish heat resistance and its preparation and application |
| CN105297427A (en) * | 2015-10-23 | 2016-02-03 | 威海新元化工有限公司 | Compound for improving heat resistance of amino-modified silicone oil carbon fiber oil formulation and preparation and application thereof |
| CN105484101A (en) * | 2015-11-20 | 2016-04-13 | 陕西科技大学 | Preparation method for inorganic fiber softening agent, and modification method for improving softness of inorganic fiber by using inorganic fiber softening agent |
| CN105601933A (en) * | 2016-01-30 | 2016-05-25 | 青岛科技大学 | Preparation method of silicone rubber surface hydrophilic coating |
| CN105603733A (en) * | 2016-02-26 | 2016-05-25 | 苏州三和开泰花线织造有限公司 | Biodegradable textile fabric softening agent and preparation method thereof |
| CN105603733B (en) * | 2016-02-26 | 2018-01-16 | 苏州三和开泰花线织造有限公司 | A kind of biodegradable fabric softener and preparation method thereof |
| CN105755837A (en) * | 2016-02-29 | 2016-07-13 | 苏州印丝特纺织数码科技有限公司 | Preparation method and application of quaternization modified amino silicon oil softener |
| CN105755837B (en) * | 2016-02-29 | 2018-05-15 | 东莞市佳乾新材料科技有限公司 | A kind of preparation method of quaternised modified amino-silicone oil softener and application |
| CN105622944B (en) * | 2016-03-30 | 2018-08-07 | 科凯精细化工（上海）有限公司 | A kind of quaternized organic silicone oil and preparation method thereof |
| CN105622944A (en) * | 2016-03-30 | 2016-06-01 | 科凯精细化工（上海）有限公司 | Quaternized organic silicone oil and preparation method thereof |
| CN105839415A (en) * | 2016-04-18 | 2016-08-10 | 广东湛丰精细化工有限公司 | Low-yellowing hydrophilic finishing agent and preparation method thereof |
| CN106192418A (en) * | 2016-07-13 | 2016-12-07 | 张静 | A kind of preparation method of milk fibre modified amino silicon oil anti pilling softener |
| CN106589385A (en) * | 2017-01-05 | 2017-04-26 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof |
| CN108252104A (en) * | 2017-12-23 | 2018-07-06 | 董晓 | A kind of preparation method for smooth agent of weaving |
| CN108252104B (en) * | 2017-12-23 | 2020-06-30 | 浙江凯洛琪服饰有限公司 | Preparation method of textile smoothing agent |
| CN108797129A (en) * | 2018-06-21 | 2018-11-13 | 湖北健客日化有限公司 | A kind of fabric softening agent |
| CN108797129B (en) * | 2018-06-21 | 2021-08-10 | 湖北健客日化有限公司 | Fabric softener |
| CN109162091A (en) * | 2018-08-29 | 2019-01-08 | 华南理工大学 | A method of super-hydrophobic antibiotic fabric is prepared based on quaternized silica |
| CN109267355A (en) * | 2018-09-27 | 2019-01-25 | 佛山九陌科技信息咨询有限公司 | A kind of preparation method of silicone oil softener |
| CN109322154A (en) * | 2018-11-07 | 2019-02-12 | 青岛奥洛思新材料有限公司 | It is a kind of for handling the lubricant and preparation method thereof of crudefiber crop rove |
| CN109322154B (en) * | 2018-11-07 | 2021-12-07 | 青岛奥洛思新材料有限公司 | Lubricant for processing hemp roving and preparation method thereof |
| CN111434852A (en) * | 2019-01-11 | 2020-07-21 | 浙江迎丰科技股份有限公司 | Short-process dyeing and finishing process for polyester-cotton blended fabric |
| CN110004726A (en) * | 2019-05-07 | 2019-07-12 | 纤化（上海）生物化工股份有限公司 | A kind of guarantor's bullet block silicone oil and preparation method thereof for elastic force cowboy |
| CN110004726B (en) * | 2019-05-07 | 2022-02-08 | 纤化（上海）生物化工股份有限公司 | Elasticity-maintaining block silicone oil for elastic jeans and preparation method thereof |
| CN110258112A (en) * | 2019-07-15 | 2019-09-20 | 江苏盛世海新材料科技有限公司 | A kind of high-performance flexible agent |
| CN110885445A (en) * | 2019-11-01 | 2020-03-17 | 湖州美伦纺织助剂有限公司 | Novel quaternary ammonium salt modified silicone oil and production process thereof |
| CN114277579A (en) * | 2021-12-28 | 2022-04-05 | 浙江东进新材料有限公司 | Processing method of sun-proof polyester cotton-like fabric |
| CN114575167A (en) * | 2022-02-23 | 2022-06-03 | 常熟理工学院 | Preparation method of radiation-proof fabric coating |
| CN115538195A (en) * | 2022-09-30 | 2022-12-30 | 浙江越新印染有限公司 | Color fixing finishing method and application thereof in pure cotton printing and dyeing |
| CN115538195B (en) * | 2022-09-30 | 2023-11-03 | 浙江越新印染有限公司 | Color fixation finishing method and application thereof in pure cotton printing and dyeing |
| CN116575165A (en) * | 2023-05-17 | 2023-08-11 | 江苏鸿鹏服饰有限公司 | Skin-friendly antibacterial sleeping bag fabric and preparation method thereof |
| CN116575165B (en) * | 2023-05-17 | 2024-02-13 | 江苏鸿鹏服饰有限公司 | Skin-friendly antibacterial sleeping bag fabric and preparation method thereof |
| CN117143345A (en) * | 2023-09-28 | 2023-12-01 | 广东宏昊化工有限公司 | Bio-based fixation softener, preparation method and application thereof |
| CN117143345B (en) * | 2023-09-28 | 2024-05-14 | 广东宏昊化工有限公司 | Bio-based fixation softener, preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101914206B (en) | 2013-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101914206B (en) | Quaternized modified amino silicone oil softener and preparation and application thereof | |
| CN104086779B (en) | Sliding block silicone oil of a kind of ultra-soft and preparation method thereof | |
| CN102250358B (en) | Block type amino polyether modified silicone oil and preparation method thereof | |
| CN101805994B (en) | Organosilicon emulsion used for hand feel finishing of wool and blended yarn thereof and preparation method and application thereof | |
| DE102004002208B4 (en) | Preparations based on organopolysiloxane-polyammonium block copolymers and their use on textile substrates | |
| CN101497697B (en) | Preparation of block water-soluble silicon oil | |
| CN101418518A (en) | Method for preparing durable hydrophilic polyether modified amino polysiloxane soft agent | |
| CN102061615A (en) | Anti-creasing softener | |
| CN102619088A (en) | Softening agent capable of improving sublimation fastness of disperse dye and wet friction fastness of reactive dye | |
| CN101503514B (en) | Synthesizing method of amino / sulfhydryl co-modified organosilicon polysiloxane | |
| CN102644200A (en) | Super-soft finishing agent of silicone oil | |
| CN105755837B (en) | A kind of preparation method of quaternised modified amino-silicone oil softener and application | |
| CN102558567A (en) | Preparation method of quaternary copolymer block organic silicon oil | |
| CN103031713A (en) | Ecotype crease-resistant shape-preserving finishing agent for textile and finishing process thereof | |
| CN108117647A (en) | A kind of preparation method with antistatic, anti-fluffing and anti-pilling organosilicon flexible durable finishes | |
| CN102660029B (en) | Cation modified supersoft hydrophilic block silicone oil compound and preparation method and application | |
| CN105648778A (en) | Preparation method of nonionic hydrophilic fatty acid amide organosilicon copolymer softener | |
| CN102634036A (en) | Novel linear amino and polyester modified organosilicon compound for textiles | |
| CN105862476A (en) | Formaldehyde-free activated dye color fixing agent and preparation method thereof | |
| CN107724086A (en) | A kind of silicone softening agent and preparation method thereof | |
| CN108047419B (en) | Preparation method of fluffy polyurethane modified organic silicon softening agent | |
| CN102086591B (en) | Organic germanium-containing home textile fabric and preparation method thereof | |
| CN101307567A (en) | Anion modified amino silicon oil fabric softeners and method for making same | |
| CN114106337B (en) | Ternary polymerization hydrophilic amino silicone oil, preparation method thereof and finishing agent | |
| CN106012546A (en) | Cation-type quaternization organic fluorosilicon oil darkening finishing agent, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| 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: 20131009 Termination date: 20160813 |