CN103724562A - Preparation method of cationic hydrophilic modified amino silicone oil - Google Patents
Preparation method of cationic hydrophilic modified amino silicone oil Download PDFInfo
- Publication number
- CN103724562A CN103724562A CN201310571764.1A CN201310571764A CN103724562A CN 103724562 A CN103724562 A CN 103724562A CN 201310571764 A CN201310571764 A CN 201310571764A CN 103724562 A CN103724562 A CN 103724562A
- Authority
- CN
- China
- Prior art keywords
- parts
- silicone oil
- weight
- preparation
- modified 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.)
- Pending
Links
- 0 *CC[N+](*)CC(*)=C Chemical compound *CC[N+](*)CC(*)=C 0.000 description 1
Abstract
The invention belongs to a preparation method of cationic hydrophilic modified amino silicone oil applied to printed and dyed products. Firstly, hydrogen-containing silicone oil has a hydrogen addition reaction with diallylamine to produce amino-modified silicone oil, and then the amino-modified silicone oil reacts with maleic anhydride fatty alcohol-polyoxyethylene ether monoester to produce the silicone oil product with a bulk copolymerization method. The silicone oil has good hydrophilic performance, and the effect of the improvement on the hydrophilic performance by the silicone oil is enhanced.
Description
Technical field
The present invention relates to a kind of preparation method of cationic hydrophilic modified amino silicon oil, is polymkeric substance preparation field.
Background technology
Amido silicon oil is the major ingredient that is used in textiles soft finishing agent.It has splendid adsorptivity, consistency.Amido silicon oil is easily emulsified into stable, transparent microemulsion.Amido silicon oil can be used separately, also can be combined into special soft finishing agent with other organosilicon or organic softening agent, is applicable to the softening of various textiless.The ammonia value of amido silicon oil is between 0.2～1.2, and ammonia value is higher, and flexibility and slippery are better, but xanthochromia can be larger.Present widely used amido silicon oil has extremely low surface tension and good water repellency, causes finish fabric to be hydrophobicity, and dress is felt sultry and is difficult to washing.
Summary of the invention
According to the present situation of silicone oil softener product performance deficiency, the invention provides a kind of modified silicon oil product that can improve silicone oil hydrophilicity.
The object of the invention is to prepare amino modified containing hydrogen silicone oil by addition reaction, again in mass polymerization mode, take amino modified containing hydrogen silicone oil and cationoid polymerisation body is raw material, prepares cationic hydrophilic modified silicon oil, to improve the xanthochromia of traditional amido silicon oil own, the defect such as hydrophobic.
To achieve these goals, the technical solution adopted in the present invention is:
A preparation method for cationic hydrophilic modified amino silicon oil, comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 80～105 parts, solvent that parts by weight are 30～50 parts by parts by weight, parts by weight are 8～24 parts and parts by weight are 0.3～0.55 part mixes, then at the temperature of 110～125 ℃, react 3～6 hours, make amino-modified silicone oil; Described solvent is one or more mixtures in Virahol, dipropylene glycol, dipropylene glycol methyl ether, butyl glycol ether, propyl carbinol;
(2) by parts by weight, be first that the amino-modified silicone oil making in the step (1) of 110～150 parts, cationic comonomer and the initiator that parts by weight are 20～45 parts mix, at the temperature of 60～80 ℃, react 3～6 hours, be cooled to below 40 ℃, make cationic hydrophilic modified amino silicon oil.
Described containing hydrogen silicone oil is end hydrogen silicone oil, and in described end hydrogen silicone oil, the quality percentage composition of hydrogen is between 1.4～1.7%, and the viscosity of this end hydrogen silicone oil when temperature is 25 ℃ is 10～50CS.
In described platinum catalyst, the quality percentage composition of platinum is between 3～4%.
Described cationic comonomer is that monomer comprises diallyl quaternary ammonium salt monomer in formula 1 and one or more in the diallyl monomeric amine salt in formula 2,
In formula 1, R
1, R
4hydrogen or C
1-C
22straight or branched alkyl;
R
2, R
3alkyl, alkenyl, aryl, with heteroatomic alkyl or alkenyl, wherein heteroatoms is selected from N, S, O;
X
-halide anion, sulfate ion or phosphate anion;
In formula 2, R5, R7 are hydrogen or C
1-C
22straight or branched alkyl;
R
6hydrogen, alkyl, alkenyl, aryl, with heteroatomic alkyl or alkenyl, wherein heteroatoms is selected from N, S, O;
X
-halide anion, sulfate ion or phosphate anion.
Cationic monomer is connected on silicone oil macromolecular chain in the mode of radical polymerization, makes silicone oil be cationic, can improve the bonding force of silicone molecule and cellulosic fibre, strengthens soft, the hydrophilic weather resistance of silicone oil.In addition, positively charged ion can also promote the fluffy, soft of cellulosic fibre; Cation group can adsorpting anion dyestuff, promotes the colour fastness of fabric, has tint retention.
Described initiator is one or more in Sodium Persulfate, Potassium Persulphate, ammonium persulphate, Diisopropyl azodicarboxylate, benzoyl peroxide, and the consumption of described initiator is 2～2.5 * 10
-3mol/L.
Beneficial effect of the present invention: introduce cationic polymerization monomer on silicone molecule chain, can effectively strengthen hydrophilicity and the weather resistance thereof of product.
Specific implementation method:
Polymkeric substance of the present invention is realized by hydrogen addition, mass polymerization preparation.Following embodiment, only illustrates, and is not only, so all within the scope of the present invention or make within the change similar to the present invention be all contained in the present invention.
Embodiment mono-
A kind of preparation method of cationic hydrophilic modified amino silicon oil comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 80 parts, solvent Virahol that parts by weight are 30 parts by parts by weight, parts by weight are 8 parts and parts by weight are 0.3 part mixes, then at the temperature of 110 ℃, react 6 hours, make amino-modified silicone oil;
(2) by parts by weight, be first the amino-modified silicone oil making in the step (1) of 110 parts, the cationic comonomer diallyldimethylammonium chloride and 2 * 10 that parts by weight are 20 parts
-3mol/L initiator Sodium Persulfate mixes, and reacts 6 hours at the temperature of 60 ℃, is cooled to below 40 ℃, makes cationic hydrophilic modified amino silicon oil.
Embodiment bis-
A kind of preparation method of cationic hydrophilic modified amino silicon oil comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 85 parts, solvent dipropylene glycol that parts by weight are 35 parts by parts by weight, parts by weight are 12 parts and parts by weight are 0.35 part mixes, then at the temperature of 115 ℃, react 5 hours, make amino-modified silicone oil;
(2) by parts by weight, be first the amino-modified silicone oil making in the step (1) of 120 parts, cationic comonomer diallyl two (beta-hydroxyethyl) ammonium chloride and 2.1 * 10 that parts by weight are 25 parts
-3mol/L initiator potassium persulfate is mixed, and reacts 5 hours at the temperature of 70 ℃, is cooled to below 40 ℃, makes cationic hydrophilic modified amino silicon oil.
Embodiment tri-
A kind of preparation method of cationic hydrophilic modified amino silicon oil comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 90 parts, solvent dipropylene glycol methyl ether that parts by weight are 40 parts by parts by weight, parts by weight are 16 parts and parts by weight are 0.4 part mixes, then at the temperature of 115 ℃, react 4 hours, make amino-modified silicone oil;
(2) by parts by weight, be first the amino-modified silicone oil making in the step (1) of 130 parts, cationic comonomer diallyl two (β-ethoxyethyl group) ammonium chloride and 2.3 * 10 that parts by weight are 35 parts
-3mol/L initiator ammonium persulfate mixes, and reacts 4 hours at the temperature of 70 ℃, is cooled to below 40 ℃, makes cationic hydrophilic modified amino silicon oil.
Embodiment tetra-
A kind of preparation method of cationic hydrophilic modified amino silicon oil comprises the steps:
(1) by parts by weight, be first that the containing hydrogen silicone oil of 100 parts, solvent ethylene glycol butyl ether parts by weight that parts by weight are 45 parts are that the platinum catalyst that the diallyl amine of 20 parts and parts by weight are 0.5 part mixes, then at the temperature of 120 ℃, react 3 hours, make amino-modified silicone oil;
(2) by parts by weight, be first the amino-modified silicone oil making in the step (1) of 140 parts, cationic comonomer diallyl two (β-hydroxypropyl) brometo de amonio and 2.4 * 10 that parts by weight are 40 parts
-3mol/L initiator Diisopropyl azodicarboxylate mixes, and reacts 3 hours at the temperature of 75 ℃, is cooled to below 40 ℃, makes cationic hydrophilic modified amino silicon oil.
Embodiment five
A kind of preparation method of cationic hydrophilic modified amino silicon oil comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 105 parts, solvent, n-butanol that parts by weight are 50 parts by parts by weight, parts by weight are 24 parts and parts by weight are 0.55 part mixes, then at the temperature of 125 ℃, react 3 hours, make amino-modified silicone oil;
(2) by parts by weight, be first the amino-modified silicone oil making in the step (1) of 150 parts, the cationic comonomer diallyl dimethyl ammonium phosphate and 2.5 * 10 that parts by weight are 45 parts
-3mol/L initiator benzoyl peroxide mixes, and reacts 3 hours at the temperature of 80 ℃, is cooled to below 40 ℃, makes cationic hydrophilic modified amino silicon oil.
Above-described embodiment is only for the inventive concept of the present invention of explaining, but not restriction to rights protection of the present invention, allly utilizes this design to carry out the change of unsubstantiality to the present invention, all should fall into protection scope of the present invention.
Claims (5)
1. a preparation method for cationic hydrophilic modified amino silicon oil, is characterized in that: described preparation method comprises the steps:
(1) platinum catalyst that the diallyl amine that be first the containing hydrogen silicone oil of 80～105 parts, solvent that parts by weight are 30～50 parts by parts by weight, parts by weight are 8～24 parts and parts by weight are 0.3～0.55 part mixes, then at the temperature of 110～125 ℃, react 3～6 hours, make amino-modified silicone oil; Described solvent is one or more mixtures in Virahol, dipropylene glycol, dipropylene glycol methyl ether, butyl glycol ether, propyl carbinol;
(2) by parts by weight, be that the amino-modified silicone oil making in the step (1) of 110～150 parts, cationic comonomer and the initiator that parts by weight are 20～45 parts mix, at the temperature of 60～80 ℃, react 3～6 hours, be cooled to below 40 ℃, make cationic hydrophilic modified amino silicon oil.
2. the preparation method of a kind of cationic hydrophilic modified amino silicon oil according to claim 1, it is characterized in that: described containing hydrogen silicone oil is end hydrogen silicone oil, in described end hydrogen silicone oil, the quality percentage composition of hydrogen is between 1.4～1.7%, and the viscosity of this end hydrogen silicone oil when temperature is 25 ℃ is 10～50CS.
3. the preparation method of a kind of cationic hydrophilic modified amino silicon oil according to claim 1, is characterized in that: in described platinum catalyst, the quality percentage composition of platinum is between 3～4%.
4. the preparation method of a kind of cationic hydrophilic modified amino silicon oil according to claim 1, it is characterized in that: described cationic comonomer is that monomer comprises diallyl quaternary ammonium salt monomer in formula 1 and one or more in the diallyl monomeric amine salt in formula 2
In formula 1, R
1, R
4hydrogen or C
1-C
22straight or branched alkyl;
R
2, R
3alkyl, alkenyl, aryl, with heteroatomic alkyl or alkenyl, wherein heteroatoms is selected from N, S, O;
X
-halide anion, sulfate ion or phosphate anion;
In formula 2, R5, R7 are hydrogen or C
1-C
22straight or branched alkyl;
R
6hydrogen, alkyl, alkenyl, aryl, with heteroatomic alkyl or alkenyl, wherein heteroatoms is selected from N, S, O;
X
-halide anion, sulfate ion or phosphate anion.
5. the preparation method of a kind of cationic hydrophilic modified amino silicon oil according to claim 1, it is characterized in that: described initiator is one or more in Sodium Persulfate, Potassium Persulphate, ammonium persulphate, Diisopropyl azodicarboxylate, benzoyl peroxide, the consumption of described initiator is 2～2.5 * 10
-3mol/L.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310571764.1A CN103724562A (en) | 2013-11-08 | 2013-11-08 | Preparation method of cationic hydrophilic modified amino silicone oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310571764.1A CN103724562A (en) | 2013-11-08 | 2013-11-08 | Preparation method of cationic hydrophilic modified amino silicone oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103724562A true CN103724562A (en) | 2014-04-16 |
Family
ID=50448879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310571764.1A Pending CN103724562A (en) | 2013-11-08 | 2013-11-08 | Preparation method of cationic hydrophilic modified amino silicone oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103724562A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108117647A (en) * | 2017-04-07 | 2018-06-05 | 南通斯恩特纺织科技有限公司 | A kind of preparation method with antistatic, anti-fluffing and anti-pilling organosilicon flexible durable finishes |
| CN111389305A (en) * | 2020-04-26 | 2020-07-10 | 杨凌单色生物科技有限公司 | Amphoteric ion organic silicon surfactant and preparation method thereof |
| CN115260415B (en) * | 2022-08-10 | 2023-10-13 | 上海金狮化工有限公司 | Preparation method of formaldehyde-free silicon-containing polymer color fixing agent for leather |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101263182A (en) * | 2005-09-08 | 2008-09-10 | 瓦克化学有限公司 | Hydrophilic organofunctional silicone copolymers |
| CN101508779A (en) * | 2009-03-04 | 2009-08-19 | 深圳天鼎精细化工制造有限公司 | Synthesis of cation amino-silicone oil |
| CN101781857A (en) * | 2010-02-05 | 2010-07-21 | 洪桂焕 | Soap-free color-fixing agent emulsion and preparation method thereof |
| CN102002162A (en) * | 2010-08-10 | 2011-04-06 | 佛山市顺德区德美瓦克有机硅有限公司 | Cation amino silicone oil micro-emulsion and preparation method thereof |
| CN102115538A (en) * | 2010-12-17 | 2011-07-06 | 华东理工大学 | Modified amino silicone oil and application thereof |
| CN102492148A (en) * | 2011-11-23 | 2012-06-13 | 华东理工大学 | Synthesis method of amino silicone oil |
-
2013
- 2013-11-08 CN CN201310571764.1A patent/CN103724562A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101263182A (en) * | 2005-09-08 | 2008-09-10 | 瓦克化学有限公司 | Hydrophilic organofunctional silicone copolymers |
| CN101508779A (en) * | 2009-03-04 | 2009-08-19 | 深圳天鼎精细化工制造有限公司 | Synthesis of cation amino-silicone oil |
| CN101781857A (en) * | 2010-02-05 | 2010-07-21 | 洪桂焕 | Soap-free color-fixing agent emulsion and preparation method thereof |
| CN102002162A (en) * | 2010-08-10 | 2011-04-06 | 佛山市顺德区德美瓦克有机硅有限公司 | Cation amino silicone oil micro-emulsion and preparation method thereof |
| CN102115538A (en) * | 2010-12-17 | 2011-07-06 | 华东理工大学 | Modified amino silicone oil and application thereof |
| CN102492148A (en) * | 2011-11-23 | 2012-06-13 | 华东理工大学 | Synthesis method of amino silicone oil |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108117647A (en) * | 2017-04-07 | 2018-06-05 | 南通斯恩特纺织科技有限公司 | A kind of preparation method with antistatic, anti-fluffing and anti-pilling organosilicon flexible durable finishes |
| CN111389305A (en) * | 2020-04-26 | 2020-07-10 | 杨凌单色生物科技有限公司 | Amphoteric ion organic silicon surfactant and preparation method thereof |
| CN111389305B (en) * | 2020-04-26 | 2021-09-07 | 杨凌单色生物科技有限公司 | Amphoteric ion organic silicon surfactant and preparation method thereof |
| CN115260415B (en) * | 2022-08-10 | 2023-10-13 | 上海金狮化工有限公司 | Preparation method of formaldehyde-free silicon-containing polymer color fixing agent for leather |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104650363B (en) | Preparation method of hyperbranched ternary polymerization organic silicon | |
| CN101781857B (en) | Soap-free color-fixing agent emulsion and preparation method thereof | |
| CN102978952B (en) | Ecological low-salt dyeing and finishing agent for reactive dyes and preparation method and applications thereof | |
| CN104086779B (en) | Sliding block silicone oil of a kind of ultra-soft and preparation method thereof | |
| CN103061148B (en) | Wet rubbing fastness improver for chitosan quaternary ammonium salt modified by organic silicon, and preparation method of improver | |
| CN103711011B (en) | Micro-crosslinking type poly(methacryloxyethyltrimethyl ammonium chloride) modified color fixing agent and preparation method thereof | |
| CN103333284B (en) | A kind of organosilicon crylic acid latex and the application as fabric finishing agent thereof | |
| CN105131174A (en) | Durable uvioresistant finishing agent applicable to both cotton and terylene and preparation method thereof | |
| CN106589386A (en) | Quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof | |
| CN105568722B (en) | The preparation method of cationic fixing agent lotion | |
| CN106589385A (en) | Low-yellowing quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof | |
| CN102443099A (en) | Preparation method of (sesqui) siloxane hybrid modified fluorinated polyacrylate emulsion | |
| CN104744642A (en) | Method for preparing nano-titanium dioxide modified color fixing agent emulsion | |
| CN103724540A (en) | Fabric dye-fixing agent emulsion and preparation method thereof | |
| CN108117647A (en) | A kind of preparation method with antistatic, anti-fluffing and anti-pilling organosilicon flexible durable finishes | |
| CN103724561A (en) | Preparation method of hydrophilic modified amino silicone oil | |
| CN102995472B (en) | Preparation method of textile color fixing agent | |
| CN103724562A (en) | Preparation method of cationic hydrophilic modified amino silicone oil | |
| CN102634036B (en) | Novel linear amino and polyester modified organosilicon compound for textiles | |
| CN105862476B (en) | A kind of formaldehyde-free active dye fixing agent and preparation method thereof | |
| CN102605112A (en) | Combined amino-silicone-oil leather greasing agent and preparation method thereof | |
| CN109098018A (en) | A kind of dyeing used additives and preparation method thereof | |
| CN104514158B (en) | A kind of application of chitosan quaternary ammonium salt in reactive dye salt-free dyeing | |
| CN105648778A (en) | Preparation method of nonionic hydrophilic fatty acid amide organosilicon copolymer softener | |
| CN107938399A (en) | A kind of color fixing agent for cloth and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| DD01 | Delivery of document by public notice |
Addressee: SHAOXING DINGXIANG TEXTILE TRADING CO., LTD. Document name: Notification of Passing Preliminary Examination of the Application for Invention |
|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| DD01 | Delivery of document by public notice | ||
| DD01 | Delivery of document by public notice |
Addressee: SHAOXING DINGXIANG TEXTILE TRADING CO., LTD. Document name: Notification of Patent Invention Entering into Substantive Examination Stage |
|
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20181010 Address after: 312000 room 206, 17 East Xindu District, Yuecheng District, Shaoxing, Zhejiang Applicant after: Gu Xiangjun Address before: No. 508 round City West Road, Shaoxing, Zhejiang Province Applicant before: SHAOXING DINGXIANG TEXTILE TRADING CO., LTD. |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20140416 |