CN101768274B - Preparation method of hydrophilic amino silicone oil - Google Patents
Preparation method of hydrophilic amino silicone oil Download PDFInfo
- Publication number
- CN101768274B CN101768274B CN200910261772XA CN200910261772A CN101768274B CN 101768274 B CN101768274 B CN 101768274B CN 200910261772X A CN200910261772X A CN 200910261772XA CN 200910261772 A CN200910261772 A CN 200910261772A CN 101768274 B CN101768274 B CN 101768274B
- Authority
- CN
- China
- Prior art keywords
- silicone oil
- silicon oil
- preparation
- epoxy
- hydrophilic amino
- 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.)
- Active
Links
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Silicon Polymers (AREA)
Abstract
The invention discloses a preparation method of hydrophilic amino silicone oil. The invention is characterized in that the preparation method comprises the following steps: A. the preparation of low-hydrogen silicone oil: siloxane ring body, high-hydrogen silicone oil, blocking agent and acid are mixed for reaction and are cooled, and the pH is adjusted; B. the preparation of epoxy silicone oil: the prepared low-hydrogen silicone oil, alkenyl epoxy compound and catalyst are mixed for reaction and are cooled; and C. the preparation of hydrophilic amino silicone oil: the prepared epoxy siliconeoil, organic amine and solvent are mixed for reaction, and the solvent is distilled. The bonding is firmer in the form of a chemical bond when the hydrophilic amino silicone oil prepared by the method reacts with the fabric, and the hydrophilic amino silicone oil is washable, has soft effect of the common amino silicone oil, no yellowing and good smoothness and antistatic property, and can be widely used in fabric finishing.
Description
Technical field
The present invention relates to a kind of preparation method of fabric softener, relate in particular to a kind of preparation method of hydrophilic amino silicone oil.
Background technology
People to the requirement of wearing dress ornament be not simply require fabric have moisture absorption, ventilative, dress is comfortable, also pursue fabric and have softness, smooth, elegant style, therefore the appearance of softening agent has just been arranged, and the now is used to such an extent that be silicone softening agent the most widely.Silicone softening agent at first obtains research, development and application in all states of America and Europe, and has obtained huge profit.Since the reform and opening-up, China's economic height development, textile and dyeing industry also progressively begins to use from developing into without silicone softening agent, has been overall application now.China joined WTO has also had a lot of years, and it is exactly textile product that the Industrial products of competitive strength are arranged in the international market most; The foreign trader requires these textile products to put in order with silicone softening agent.Therefore, research, development and application silicone softening agent have important strategic meaning and economic implications.
Now, what sell on the market mainly is amino-silicone oil softening agent, wherein having more than 90% at this is α-aminoethyl-β-aminopropyl polysiloxane product, or do the product of silane coupling agent and other properties-correcting agent reaction with it, in fact also be the product that contains α-aminoethyl-β-aminopropyl polysiloxane.Though its flexibility is very good,, contain 3 reactive hydrogen atoms on its side chain because 2 amino (primary amino and a secondary amino group) are arranged.This structure formation is because the amino particularly existence of primary amino causes yellowing easily.Xanthochromia mechanism is that amino oxygenolysis forms chromophoric group (azo-group and azoxy), and this diamine type structure has synergistic effect, and the promote the oxidation effect helps forming chromophoric group, causes the fabric yellowing.Arrangement white or the easy flavescence of light fabric.The fabric hydrophilic of amido silicon oil arrangement is not enough, and water absorbability is not strong, is used for chemical ﹠ blended fabric or cotton and chemical fiber blended fabrics, form oil mark and static electrification easily, when fabric being put in order, though good wetting ability is arranged with general epoxide modified silicone oil, but its soft smooth property is not enough, sends out puckery; The stability of emulsion that is made into is poor, and rate of moisture absorption is not high, and waste is big; With polyether-modified silicone oil, because of it is simple hydrogen bonded, fastness and flexibility are poor.Therefore prior art has to be updated and improves.
Summary of the invention
The objective of the invention is at above some shortcomings, a kind of preparation method that can hydrophilicly have the silicone oil of the soft smooth performance of amido silicon oil again is provided, through the hydrophilic amino silicone oil finish fabric that this method is produced, its wetting ability, flexibility, elasticity, whiteness and washing fastness, performance such as antistatic are very good.
The preparation method's of hydrophilic amino silicone oil of the present invention feature is may further comprise the steps:
A, silicon oil of low hydrogen content preparation,
Siloxanes ring body, high containing hydrogen silicone oil, end-capping reagent (as hexamethyldisiloxane) and acid (example hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid) are mixed, in following conditioned response:
(1) the mass parts ratio of siloxanes ring body, high containing hydrogen silicone oil, end-capping reagent and acid is followed successively by 70~92: 0.5~30: 0.5~5: 1~5,
(2) temperature of reaction is 60~120 ℃,
(3) reaction times is 6~10 hours,
After having reacted, be cooled to 30~10 ℃, regulating pH then is 5~7, makes silicon oil of low hydrogen content;
The preparation of B, epoxy silicon oil,
The silicon oil of low hydrogen content that makes is mixed with thiazolinyl epoxy compounds, catalyzer (for example Platinic chloride), in following conditioned response:
(1) the mass parts ratio of silicon oil of low hydrogen content, thiazolinyl epoxy compounds, catalyzer is followed successively by: 70~95: 0.5~30: 0.1~1,
(2) temperature is 60~150 ℃,
(3) 5~12 hours time,
After having reacted, low-boiling point material is removed in underpressure distillation, is cooled to 30~10 ℃, makes epoxy silicon oil;
The preparation of C, hydrophilic amino silicone oil
With epoxy silicon oil, organic amine and the solvent that makes, in following conditioned response:
(1) ratio of the mass parts of epoxy silicon oil and organic amine is followed successively by: 70~95: 5~30, and the quality of solvent is 0.5~1 of epoxy silicon oil and an organic amine quality sum;
(2) temperature is 60~150 ℃,
(3) 5~12 hours time,
After having reacted, distilling off solvent makes hydrophilic amino silicone oil.
Siloxanes ring body in the described steps A is octamethylcyclotetrasiloxane (D4) or methyl cyclosiloxane mixture (DMC).
The viscosity of the silicon oil of low hydrogen content in the described steps A is at 50~5000mpa.s, and hydrogen content is 0.02%~1.0%.
Alkenyl epoxides among the described step B is a 1-vinyl-3,4-epoxy cyclohexane, glycidyl allyl ether or vinylformic acid Racemic glycidol ether-ether.
Organic amine among the described step C is methylamine, ethamine, propylamine, hexahydroaniline, aniline, benzene methanamine or N, N-dimethyl-1,3-propylene diamine.
Solvent among the described step C is methyl alcohol, ethanol, toluene or Virahol.
Hydrophilic amino silicone oil viscosity among the described step C is at 500~5000mPa.s, and the ammonia value is at 0.1~1.0mmol/g.
In the preparation process of the present invention, adopt the thiazolinyl epoxy compounds to participate in addition reaction, make the existing hydroxyl of amido silicon oil finished product, ether is arranged again, because of containing amino and hydroxyl in its structure, because it is amino, hydroxyl has strong polarity, can interact with groups such as hydroxyl in the fiber, carboxyls, produce extremely strong orientation and adsorptivity, therefore improve siloxanes aligning on fiber greatly, made fabric sofetening, smooth, stiffening, crease-resistant, had good static resistance and certain washing fastness simultaneously.Make the super softness of fabric feeling smooth, plentiful, water absorbability, static resistance, whiteness and weather resistance are preferably arranged again.Make amido silicon oil with the inventive method, overcome the shortcoming of common amido silicon oil, simple polyethers, simple epoxy modified silicon oil, its good hydrophilic property, do the time spent with fabric and combine more firmly, more washable with the form of valence bond, have common amido silicon oil soft effect again, and xanthochromia not again, smooth property, static resistance is good, is widely used in the middle of the textile finishing.
In sum, doing the time spent with the hydrophilic amino silicone oil of the inventive method preparation and fabric combines more firm, more washable with the form of valence bond, have common amido silicon oil soft effect again, and xanthochromia not, its smooth property, static resistance is good, is widely used in the middle of the textile finishing.
Embodiment
Below in conjunction with embodiment technical scheme of the present invention is further described.
Embodiment 1
A, in the reactor of stirring is housed, start stirring, the octamethylcyclotetrasiloxane that adds 92 parts successively, 3 parts of high containing hydrogen silicone oils (trade mark XFC202), 2 parts of end-capping reagent (hexamethyldisiloxane, trade mark HX-18), 3 parts hydrochloric acid, mix, reacted 11 hours down at 60 ℃, material in the reactor by muddy transfer to transparent, after having reacted, logical chuck cooling water temperature to 25 ℃ is regulated pH=6 with this understanding, then the sampling detect hydrogen content 0.05%, recording viscosity with rotational viscosimeter is 500mPa.s, makes water white silicon oil of low hydrogen content, uses to get the step ready.
B, with 89.9 parts of silicon oil of low hydrogen content, 0.1 part catalyzer (Platinic chloride, trade mark NMC2505), 10 parts of glycidyl ethers (thiazolinyl epoxy compounds) change over to and agitator are housed and are connected with in the reactor of complementary condenser, 60 ℃ of reactions 10 hours, under the 0.09MPa vacuum condition, steam low-boiling point material, be cooled to 25 ℃, obtain water white epoxy silicon oil, use to get the step ready.
C, with the dimethylamine solution of 90 parts of epoxidation silicon oils and 10 part 35%, make solvent with 0.7 times of methyl alcohol of the total amount that feeds intake, 60 ℃ of reactions 10 hours, under normal pressure, steam toluene then, water white transparency thick liquid crude oil products, i.e. hydrophilic amino silicone oil.Sampling detects, and recording viscosity with rotational viscosimeter is 1500mPa.s, and the ammonia value is 0.2mmol/g.
Embodiment 2
A, in the reactor of stirring is housed, start stirring, add 92 parts cyclotetrasiloxane mixture, 3 parts of high containing hydrogen silicone oils, 2 parts of end-capping reagents (hexamethyldisiloxane) successively, 3 parts phosphoric acid mixes, reacted 7 hours down at 100 ℃, material in the reactor by muddy transfer to transparent, after having reacted, logical chuck cooling water temperature to 25 ℃, regulate pH=6 then with this understanding, record hydrogen content 0.05%, recording viscosity with rotational viscosimeter is 480mPa.s, makes water white silicon oil of low hydrogen content.
B, with 89.9 parts of silicon oil of low hydrogen content, 0.1 part catalyzer (Platinic chloride), and add 10 parts 1-vinyl-3, the 4-epoxy cyclohexane, under 100 ℃, stirring reaction 8 hours steams low-boiling point material then under the 0.09MPa vacuum condition, obtain water white epoxide.
C, the epoxide that obtains is added 90 parts, 10 parts in 35% ethamine, the ethanol that adds 1 times of epoxide and ethamine weight is made solvent, 80 ℃ of reactions 10 hours, under normal pressure, steam toluene then, get water white transparency thick liquid crude oil products, i.e. hydrophilic amino silicone oil.Sampling detects, and recording viscosity with rotational viscosimeter is 2000mPa.s, and the ammonia value is 0.24mmol/g.
Embodiment 3
A, in the reactor of stirring is housed, start stirring, add 70 parts octamethylcyclotetrasiloxane, 25 parts of high containing hydrogen silicone oils, 2 parts of end-capping reagents (hexamethyldisiloxane) successively, 3 parts sulfuric acid mixes, reacted 6 hours down at 120 ℃, material in the reactor by muddy transfer to transparent, after having reacted, logical chuck cooling water temperature to 25 ℃, regulate pH=6 then with this understanding, record hydrogen content 0.4%, recording viscosity with rotational viscosimeter is 600mPa.s, makes water white silicon oil of low hydrogen content.
B, will go up the step and obtain 74.9 parts of silicon oil of low hydrogen content, 0.1 part catalyzer (Platinic chloride) and change over to and agitator is housed and is connected with in the reactor of complementary condenser, and add 25 parts of 1-vinyl-3, the 4-epoxy cyclohexane, 120 ℃ of reactions 6 hours, under the 0.09MPa vacuum condition, steam low-boiling point material, obtain water white epoxide.
C, with the propylamine of 80 parts, 20 part 35% of the epoxide that obtain, make solvent with the toluene of 0.5 times of charging capacity, 100 ℃ of reactions 9 hours down, under normal pressure, steam toluene, water white transparency thick liquid crude oil products, i.e. hydrophilic amino silicone oil.Sampling detects, and recording viscosity with rotational viscosimeter is 4300mPa.s, and the ammonia value is 0.7mmol/g.
Embodiment 4
A, in the reactor of stirring is housed, start stirring, add 80 parts cyclotetrasiloxane mixture, 15 parts of high containing hydrogen silicone oils, 2 parts of end-capping reagents (hexamethyldisiloxane) successively, 3 parts acetic acid mixes, reacted 7 hours down at 100 ℃, material in the reactor by muddy transfer to transparent, after having reacted, logical chuck cooling water temperature to 25 ℃, regulate pH=6 then with this understanding, record hydrogen content 0.45%, recording viscosity with rotational viscosimeter is 550mPa.s, makes water white silicon oil of low hydrogen content.
B, will go up the step and obtain 74.9 parts of silicon oil of low hydrogen content, 0.1 part catalyzer (Platinic chloride) and change over to and agitator is housed and is connected with in the reactor of complementary condenser, and add 25 parts 1-vinyl-3, the 4-epoxy cyclohexane, 60 ℃ of reactions 12 hours, under the 0.09MPa vacuum condition, steam low-boiling point material then, obtain water white epoxide.
C, with 80 parts, the 20 parts aniline of epoxide that obtain, make solvent with the Virahol of 1 times of charging capacity, 150 ℃ the reaction 8 hours, under normal pressure, steam Virahol then, water white transparency thick liquid crude oil products, i.e. hydrophilic amino silicone oil.Sampling detects, and recording viscosity with rotational viscosimeter is 4800mPa.s, and the ammonia value is 0.55mmol/g
Embodiment 5
A, in the reactor of stirring is housed, start stirring, add 70 parts cyclotetrasiloxane mixture, 25 parts of high containing hydrogen silicone oils, 3 parts of end-capping reagents (hexamethyldisiloxane) successively, 2 parts acetic acid mixes, reacted 6 hours down at 120 ℃, material in the reactor by muddy transfer to transparent, after having reacted, logical chuck cooling water temperature to 25 ℃, regulate pH=6 then with this understanding, recording hydrogen content is 0.2%, recording viscosity with rotational viscosimeter is 750mPa.s, makes water white silicon oil of low hydrogen content.
B, will go up the step and obtain 74 parts of silicon oil of low hydrogen content and change in the reactor that agitator is housed and is connected with complementary condenser, the catalyzer (Platinic chloride) that adds 1 part of massfraction, and adding 1-vinyl-3,25 parts of 4-epoxy cyclohexanes, 150 ℃ of reactions 5 hours, under the 0.09MPa vacuum condition, steam low-boiling point material then, obtain water white epoxide.
C, with the N of 80 parts, 20 parts of the epoxide that obtain, N-dimethyl-1,3-propylene diamine, Virahol with 1 times of charging capacity is made solvent, 120 ℃ of reactions 9 hours, steams Virahol then under normal pressure, get water white transparency thick liquid crude oil products, i.e. hydrophilic amino silicone oil.Sampling detects, and recording viscosity with rotational viscosimeter is 4900mPa.s, and the ammonia value is 0.9mmol/g.
The application performance contrast of amido silicon oil of the present invention and other amido silicon oil
Below be by the hydrophilic amino silicone oil of the inventive method making and the performance comparison table of other silicone oil, the A in each table represents conventional hydrophilic silicone oil, and C represents hydrophilic amino silicone oil of the present invention:
1. the environmental compatibility of emulsion
Through behind the multiple tracks chemical process, inevitably can the be residual a small amount of not impurity (as acid, alkali, salt etc.) of eccysis fully of cloth cover; Softening agent also can be subjected to factor affecting such as vibratory impulse, high and low temperature shift in storage process.So, require softening agent can keep certain stability in these cases.The environmental compatibility broad of amido silicon oil of the present invention can be guaranteed stable use the under normal condition, and is as shown in table 1.
The environmental compatibility contrast of table 1 hydrophilic amino silicone oil emulsion
Project | A | C |
Acid resistance (pH=3) | Layering | Stable |
Alkali resistance (pH=10 | Become muddy | Stable |
Salt tolerance: hard water (250 * 10-6) NaCl (10g/L) | Stable muddy | Stable |
Thermotolerance :-4 ℃ 50 ℃ | Layering is basicly stable | The back performance of thawing is normally stable |
Centrifugal stability (3000r/min) | Stable | Stable |
2. be organized the feel and the wetting ability of fabric
Fabric is after certain density softening agent arrangement, and 2h naturally gets damp again; Allow 10 experienced hand valuation experts estimate the feel of fabric from different angle, 5 grades best, and 1 grade the poorest.Wetting ability adopts the water droplet osmose process, measures the complete penetration time of water droplet, s.Feel and wetting ability evaluation result see Table 2.
Table 2. is organized the wetting ability and the feel/level of fabric
The finishing composition kind | A | C |
Wetting ability/s | 8 | 1 |
Flexibility | 4 | 5 |
Elasticity | 2 | 4 |
Fullness ratio | 3 | 5 |
3. yellow (look) sex change
The xanthochromia of amido silicon oil finish fabric (or look change) mechanism is complicated, and present most investigators think that xanthochromic major cause is to be caused by the oxidized chromophoric group that forms of amino.
Impregnation technology: softening agent consumption 20g/l, 4%~5% (o.w.f), the 30min → dehydration → oven dry (100 ℃) of 60 ℃ of dippings.
Table 3 is organized Huang (look) sex change of fabric
Title | Yellow value degree |
Do not brighten cloth specimen | 0.328 |
Handle cloth specimen with A | -5.569 |
Handle cloth specimen with C | -5.277 |
4. be organized the washing fastness of fabric
Hydrophilic softener is providing the absorptive while owing to have hydrophilic radical for fabric, also break away from fabric easily when washing, thereby cause fabric feeling and hydrophilic declining to a great extent.The response type hydrophilic amino silicone oil is owing to have the active group that can react with fiber, so weather resistance improves; Usually the active group on the silicone oil is many more, combines firmly more with fiber, and washing fastness is good more.After cloth specimen carried out softening,, estimate the feel and the wetting ability of washing the back cloth specimen, the results are shown in Table 4 with standard wash program washing 10 times.
Table 4 is organized the washing fastness of back fabric
As can be seen from Table 4, the washing fastness of hydrophilic amino silicone oil of the present invention is very good.
Claims (3)
1. the preparation method of a hydrophilic amino silicone oil is characterized in that described method may further comprise the steps:
A, silicon oil of low hydrogen content preparation,
Siloxanes ring body, high containing hydrogen silicone oil, end-capping reagent and acid are mixed, in following conditioned response:
(1) the mass parts ratio of siloxanes ring body, high containing hydrogen silicone oil, end-capping reagent and acid is followed successively by 70~92: 0.5~30: 0.5~5: 1~5,
(2) temperature of reaction is 60~120 ℃,
(3) reaction times is 6~10 hours,
After having reacted, be cooled to 30~10 ℃, regulating pH then is 5~7, makes silicon oil of low hydrogen content;
Siloxanes ring body described in the steps A is octamethylcyclotetrasiloxane or methyl cyclosiloxane mixture;
The preparation of B, epoxy silicon oil,
With the silicon oil of low hydrogen content that makes and thiazolinyl epoxy compounds, catalyst mix, in following conditioned response:
(1) the mass parts ratio of silicon oil of low hydrogen content, thiazolinyl epoxy compounds, catalyzer is followed successively by: 70~95: 0.5~30: 0.1~1,
(2) temperature is 60~150 ℃,
(3) 5~12 hours time,
After having reacted, low-boiling point material is removed in underpressure distillation, is cooled to 30~10 ℃, makes epoxy silicon oil;
Alkenyl epoxides described in the step B is a 1-vinyl-3,4-epoxy cyclohexane or glycidyl allyl ether;
The preparation of C, hydrophilic amino silicone oil,
With epoxy silicon oil, organic amine and the solvent that makes, in following conditioned response:
(1) ratio of the mass parts of epoxy silicon oil and organic amine is followed successively by: 70~95: 5~30, and the quality of solvent is 0.5~1 of described epoxy silicon oil and an organic amine quality sum;
(2) temperature is 60~150 ℃,
(3) 5~12 hours time,
After having reacted, distilling off solvent makes hydrophilic amino silicone oil;
Organic amine described in the step C is dimethylamine, ethamine, propylamine, aniline or N, N-dimethyl-1,3-propylene diamine;
Solvent described in the step C is methyl alcohol, ethanol, toluene or Virahol.
2. the preparation method of amido silicon oil as claimed in claim 1, it is characterized in that: the viscosity of the silicon oil of low hydrogen content in the described steps A is at 50~5000mpa.s, and hydrogen content is 0.02%~1.0%.
3. the preparation method of amido silicon oil as claimed in claim 1, it is characterized in that: the hydrophilic amino silicone oil viscosity among the described step C is at 500~5000mPa.s, and the ammonia value is 0.1~1.0mmol/g.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910261772XA CN101768274B (en) | 2009-12-29 | 2009-12-29 | Preparation method of hydrophilic amino silicone oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910261772XA CN101768274B (en) | 2009-12-29 | 2009-12-29 | Preparation method of hydrophilic amino silicone oil |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101768274A CN101768274A (en) | 2010-07-07 |
CN101768274B true CN101768274B (en) | 2011-09-21 |
Family
ID=42501392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910261772XA Active CN101768274B (en) | 2009-12-29 | 2009-12-29 | Preparation method of hydrophilic amino silicone oil |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101768274B (en) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102417595B (en) * | 2011-11-20 | 2013-01-02 | 浙江精业生化有限公司 | Preparation method of novel polyurethane-modified organic silica gel |
CN102516549A (en) * | 2011-12-16 | 2012-06-27 | 浙江汉邦化工有限公司 | Method for synthesizing main chain block polyether hydrophilic amino silicone oil |
CN102838748A (en) * | 2012-09-07 | 2012-12-26 | 江苏佳成特种纤维有限公司 | Synthetizing method of high textile yarn self-adhesive lubricants |
CN102942697A (en) * | 2012-10-22 | 2013-02-27 | 浙江安诺其助剂有限公司 | Preparation method of main chain hydrophilic modified amino silicone oil |
CN103642044B (en) * | 2013-12-05 | 2016-03-23 | 宁波润禾化学工业有限公司 | The preparation method of the anti-yellowing change modified amino silicon oil of a kind of high reactivity |
CN103665380A (en) * | 2013-12-27 | 2014-03-26 | 蓝星化工新材料股份有限公司江西星火有机硅厂 | Preparation method for low hydrogen-containing silicon oil |
CN104452311B (en) * | 2014-11-25 | 2017-02-22 | 杭州传化精细化工有限公司 | Method for preparing side-chain-modified organosilicon softener |
CN105524284B (en) * | 2016-01-12 | 2018-12-11 | 浙江大学 | A kind of polysiloxanes-polyethylene graft copolymer and its preparation method and application |
CN109071820B (en) * | 2016-05-10 | 2021-08-17 | 美国陶氏有机硅公司 | Silicone block copolymers with amino-functional end-capping groups and methods of making and using the same |
CN107964100A (en) * | 2016-10-19 | 2018-04-27 | 苏州汉力新材料有限公司 | A kind of preparation method of epoxy modified polysiloxane |
CN107034675B (en) * | 2017-04-21 | 2019-04-19 | 潍坊佳诚数码材料有限公司 | A kind of preparation method of modified organic silicon textile coating agent |
CN108299829B (en) * | 2018-03-16 | 2020-07-28 | 武汉大学 | Organosilicon interpenetrating network polymer and preparation method thereof |
CN108951169B (en) * | 2018-07-18 | 2021-02-09 | 杭州美高华颐化工有限公司 | Preparation method of natural alcohol ether modified organosilicon hydrophilic softening agent |
CN109252418A (en) * | 2018-08-09 | 2019-01-22 | 黄勇 | A kind of preparation method of paper pulp fluff type softening agent |
CN111072972A (en) * | 2019-12-14 | 2020-04-28 | 烟台开发区金宏化工有限公司 | Preparation method of epoxy-terminated silicone oil and application of epoxy-terminated silicone oil in amino silicone oil |
CN110983787B (en) * | 2019-12-17 | 2022-02-11 | 广东新翔星科技股份有限公司 | Hydrophilic thickening organosilicon softening agent and preparation method thereof |
CN112321834A (en) * | 2020-11-21 | 2021-02-05 | 英德市东鸿化工科技有限公司 | Preparation method of hydrophilic silicone oil |
CN112832016B (en) * | 2021-02-03 | 2023-12-01 | 义乌市七多服饰有限公司 | Preparation method of antistatic shirt fabric |
-
2009
- 2009-12-29 CN CN200910261772XA patent/CN101768274B/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN101768274A (en) | 2010-07-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101768274B (en) | Preparation method of hydrophilic amino silicone oil | |
CN104650364B (en) | A kind of preparation method of hyperbranched polyether amino block organosilicon | |
CN101497697B (en) | Preparation of block water-soluble silicon oil | |
CN103193981A (en) | Hydrophilic aminosilicon oil, and preparation method and uses thereof | |
CN101805994B (en) | Organosilicon emulsion used for hand feel finishing of wool and blended yarn thereof and preparation method and application thereof | |
CN101914206B (en) | Quaternized modified amino silicone oil softener and preparation and application thereof | |
CN102643435B (en) | Supersoft hydrophilic block silicone oil compound and preparation method thereof | |
CN103351469B (en) | A kind of preparation method of block silicone oil softening agent | |
CN107129578A (en) | The preparation method of network structure amino-modified silicone oil finishing agent | |
CN103193984A (en) | Hydrophilic aminosilicon oil, and preparation method and uses thereof | |
CN101117386A (en) | New polysiloxanes with quaternary ammonium groups, method for their manufacture and their use as textile softeners | |
CN107083683A (en) | A kind of preparation method of hydrophilic smooth organic silicone finishing agent | |
CN104086779A (en) | Super-soft/smooth block silicon oil and preparation method thereof | |
CN104562712A (en) | Preparation method of organosilicone multicopolymer fabric softener | |
CN108219147A (en) | A kind of preparation method of hydrophilic silicone oil | |
CN101503514B (en) | Synthesizing method of amino / sulfhydryl co-modified organosilicon polysiloxane | |
CN109403048A (en) | A kind of cotton hydrophilic block polyethers amido silicon oil and preparation method thereof | |
CN102644200A (en) | Super-soft finishing agent of silicone oil | |
CN106835713A (en) | A kind of organosilicon high-elastic smooth finishing agent and preparation method thereof | |
CN105001423A (en) | Organosilicon softening finishing agent with ice-cold feeling and preparation method of organosilicon softening finishing agent | |
CN111718490A (en) | Modified block silicone oil containing trace low-ring bodies and preparation method thereof | |
US20220154392A1 (en) | Alkoxylated-polyethylenimine and composition containing the same | |
CN102660029B (en) | Cation modified supersoft hydrophilic block silicone oil compound and preparation method and application | |
CN105504291B (en) | A kind of linearity block amino-silicone oil softening agent and its preparation method and application | |
CN102643436B (en) | Supersoft hydrophilic block silicone oil intermediate compound and preparation method 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 | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 1 No. 434200 Hubei city of Songzi province Chen Zhen Liyuan Road Patentee after: HUBEI COLOR ROOT TECHNOLOGY CO., LTD. Address before: 1 No. 434200 Hubei city of Songzi province Chen Zhen Liyuan Road Patentee before: Liyuan (Hubei) Technology Co.,Ltd. |