CN103182271A - Organosilicon surfactant and preparation method and application thereof - Google Patents
Organosilicon surfactant and preparation method and application thereof Download PDFInfo
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- CN103182271A CN103182271A CN2011104461253A CN201110446125A CN103182271A CN 103182271 A CN103182271 A CN 103182271A CN 2011104461253 A CN2011104461253 A CN 2011104461253A CN 201110446125 A CN201110446125 A CN 201110446125A CN 103182271 A CN103182271 A CN 103182271A
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- organic silicon
- silicon surfactant
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
Abstract
The present invention discloses an organosilicon surfactant and a preparation method and application thereof. The organosilicon surfactant has a structure shown as a formula (I), wherein c is not 0; a, b and c are all integers and 10<a+b+c<200; m=0-40; n=0-30; x=3-30; x, m and n are integers, and m and n are not 0 simultaneously; R is a C6-C20 straight-chain alkyl or a isomer long-chain alkyl, or alkylphenyl group; and R' is H, CH3, C2H5, C3H7 or C4H9. The organosilicon surfactant has a novel structure, and excellent emulsifying ability. The organosilicon surfactant has excellent emulsifying ability for polydimethylsiloxane in a large viscosity range and various modified polydimethylsiloxane, can achieve good emulsion effects by single-use, and does not need to be compounded with other emulsifiers. The emulsification process is simple, a homogenizer or other special emulsification processes can be canceled, a stable O/W type silicone oil emulsion is prepared and the use is easy.
Description
Technical field
The present invention relates to the organic silicon surfactant chemical field, be specifically related to a kind of organic silicon surfactant and its preparation method and application.
Background technology
Organic silicon surfactant is a kind of novel surfactant that grows up along with the organosilicon new material, and it has won wide survival and development space with particular performances, has now become more and more important a kind of surfactant.
Organic silicon surfactant mainly refers to the dimethyl silicone polymer to be hydrophobic main chain, introduces one or more polar organic groups therein and the class surfactant that constitutes.Except the general character with conventional surfactants, also have than the better surface-active of conventional surfactants, be class surfactant efficiently, have emulsibility, dispersiveness, easy spread, wetability, antistatic behaviour, performances such as froth breaking, steady bubble, foaming.These characteristics are because of dimethyl silicone polymer low surface tension and weak intermolecular force.
Emulsifying agent is the important component part of emulsion, and it is the bridge that connects oil phase and water.Keep stable for system is satisfied in useful life, people have developed miscellaneous emulsifying agent, or be one-component or be Compositional type, or are universal or are tailored version.
Along with the development of organosilicon material, the kind of silicone based emulsifying agent is on the increase, and performance also improves constantly, but single use is applied to the rarely seen report of O/W organosilyl surfactant in the silicone oil emulsion formulations.If want to obtain stable Si/W type emulsion, existing method is, undertaken compositely by the emulsifying agent with different HLB values, makes the HLB value of the HLB value of emulsifier system and emulsified silicone oil quite, perhaps by emulsifying process such as mechanical homogenizer etc. especially.Yet, the silicone oil of different viscosities, not quite the same to the requirement of emulsifier hlb value, different modified silicon oils, its HLB generally also have certain difference.This engineer that just requires to fill a prescription is to different silicone oil emulsion systems, compositely goes out different emulsifier systems.
Summary of the invention
The object of the present invention is to provide a kind of organic silicon surfactant.The architectural feature of this organic silicon surfactant is, the polysiloxane side chain is through hydrosilylation, grafting with chain alkyl or alkyl phenyl terminated polyether, it is to dimethyl silicone polymer and the various modified dimethyl polysiloxane of very big range of viscosities, excellent emulsifying capacity is all arranged, single use can reach the good emulsifying effect, need not with other emulsifying agents composite, and emulsifying process is simple, need not homogenizer or other special emulsifying process, just can make stable silicone oil emulsion, easy to use.
The present invention also aims to provide the application of described organic silicon surfactant in O/W type silicone oil emulsion prescription.
Above-mentioned purpose of the present invention is achieved by following proposal:
A kind of organic silicon surfactant has structure shown in the formula (I):
Wherein, c is non-vanishing; A, b, c are integer and 10＜a+b+c＜200; M=0～40; N=0～30; X=3～30; X, m, n is integer, and m, and n is not 0 simultaneously; R is C
6～20Straight chain or isomery chain alkyl, or be alkyl phenyl; R ' is H, CH
3, C
2H
5, C
3H
7, C
4H
9
As a kind of preferred version, the structure of described organic silicon surfactant is preferably a=0～150; B=0～60; C=1～60.
As a kind of preferred version, the structure of described organic silicon surfactant is preferably a=1～60; B=1～20; C=1～20; A, b, c are integer and 20＜a+b+c＜100;
M=5～15; N=6～20; X=6～12; X, m, n is integer;
R is C
8～16Straight chain or isomery chain alkyl.
The preparation method of described organic silicon surfactant is as follows:
The allyl polyether and the containing hydrogen silicone oil that comprise the steps: to have formula (III) structure or formula (II), formula (III) structure add in the reactor; under the protection of nitrogen atmosphere; stir; heat temperature raising to 80～100 ℃; add chloroplatinic acid-isopropyl alcohol catalyst; continue to be heated to 110～180 ℃ of reactions, become transparent until system, obtain described organic silicon surfactant.
Described organic silicon surfactant is colourless to light yellow liquid or paste.
The application of described organic silicon surfactant in emulsifying agent.
Described organic silicon surfactant has excellent emulsifiability, and the emulsifying agent as O/W type silicone oil emulsion prescription can use separately.
Described organic silicon surfactant is during as the emulsifying agent of O/W type silicone oil emulsion prescription, and its consumption is organic silicon surfactant by mass ratio: silicone oil=1: 2～6.
Described organic silicon surfactant is during as the emulsifying agent of cream frost prescription, and its consumption is this organic silicon surfactant by mass ratio: treat emulsification system=1: 5～9.
(for example dimethyl silicone polymer and the various modified dimethyl polysiloxane of about 2cSt～12500cSt) all have good emulsifying capacity to organic silicon surfactant of the present invention to very big range of viscosities.
Compared with prior art, the present invention has following advantage:
Novel organosilicon surfactant of the present invention, the two kinds of hydrophobic segments of alkane that contain polysiloxane in the structure and directly link to each other with the polyethers chain link, there is the polyethers hydrophilic radical of a plurality of polarity the centre, thereby has excellent emulsifying capacity; Described novel organosilicon surfactant is to dimethyl silicone polymer and the various modified dimethyl polysiloxane of very big range of viscosities, good emulsifying capacity is all arranged, single use can reach the good emulsifying effect, need not with other emulsifying agents composite, and emulsifying process is simple, need not homogenizer or other special emulsifying process, just can make stable O/W type silicone oil emulsion, easy to use.
The specific embodiment
Further explain the present invention below in conjunction with embodiment, but embodiment does not do any type of restriction to the present invention.
Among the embodiment, used catalyst is this area chloroplatinic acid-isopropyl alcohol catalyst commonly used.
Embodiment 1
Having agitating device, drum N
2In the three-neck flask of device and thermometer, (m=10, n=6, R ' are C to add 0.3mol allyl polyether formula (II)
3H
7), (x=9, R are C to 0.3mol allyl polyether formula (III)
12H
25); 0.5mol contain containing hydrogen silicone oil (the a+b+c ≈ 80 that hydrogen number is about 0.3% (mass percent); this shows b+c ≈ 18; a: b: c ≈ 62: 9: 9), under the protection of nitrogen atmosphere, when heating to 80 ℃; add the 0.03g catalyst; continue to be heated to 120 ℃～130 ℃ reactions, until the system bleach, namely obtain light yellow transparent organic silicon surfactant.
Embodiment 2
Having agitating device, drum N
2In the three-neck flask of device and thermometer, add 0.2mol allyl polyether (II) (m=38, n=0, R ' are H), (x=3, R are C to 0.3mol allyl polyether (III)
16H
33); 0.4mol contain containing hydrogen silicone oil (the a+b+c ≈ 130 that hydrogen number is about 0.2% (mass percent); this shows b+c ≈ 20; a: b: c ≈ 110: 8: 12), under the protection of nitrogen atmosphere, when heating to 100 ℃; add the 0.03g catalyst; continue to be heated to 150 ℃～160 ℃ reactions, until the system bleach, namely obtain light yellow transparent organic silicon surfactant.
Embodiment 3
Having agitating device, drum N
2In the three-neck flask of device and thermometer, add 0.18mol allyl polyether (II) (m=2, n=30, R ' are H), (x=28, R are C to 0.2mol allyl polyether (III)
18H
37); 0.32mol contain containing hydrogen silicone oil (the a+b+c ≈ 30 that hydrogen number is about 0.35% (mass percent); this shows b+c ≈ 20; a: b: c ≈ 22: 5: 3), under the protection of nitrogen atmosphere, when heating to 90 ℃; add the 0.03g catalyst; continue to be heated to 130 ℃～140 ℃ reactions, until the system bleach, namely obtain light yellow transparent organic silicon surfactant.
Embodiment 4
Having agitating device, drum N
2In the three-neck flask of device and thermometer, (m=16, n=10, R ' are CH to add 0.25mol allyl polyether (II)
3), (x=7, R are C to 0.22mol allyl polyether (III)
6H
13); be about (mass percent) containing hydrogen silicone oil (a+b+c ≈ 140 of 0.17% 0.4mol contain hydrogen number; this shows b+c ≈ 20; a: b: c ≈ 120: 11: 9), under the protection of nitrogen atmosphere, when heating to 94 ℃; add the 0.03g catalyst; continue to be heated to 160 ℃～170 ℃ reactions, until the system bleach, namely obtain light yellow transparent organic silicon surfactant.
Embodiment 5
Having agitating device, drum N
2In the three-neck flask of device and thermometer, (x=25, R are C to add 0.33mol allyl polyether (III)
20H
41); be about (mass percent) containing hydrogen silicone oil (a+c ≈ 95 of 0.28% 0.3mol contain hydrogen number; this shows b=0, c ≈ 20, a: c ≈ 75: 20); under the protection of nitrogen atmosphere; when heat temperature raising is heated to 90 ℃, add the 0.03g catalyst, continue to be heated to 160 ℃～170 ℃ reactions; until the system bleach, namely obtain light yellow transparent organic silicon surfactant.
Embodiment 6
In the emulsification still, add 20 parts of dimethyl siloxanes (different viscosities), and the organic silicon surfactant of 6 parts of embodiment 1 gained, after stirring, the about 6 parts of distilled water of disposable adding (or purified water), continue fully to mix, this moment, system was transparent paste.Under stirring condition, slowly add remaining 68 parts of water subsequently, can obtain the milky white liquid of blueing.2500r/min * 15min is centrifugal, and is not stratified.Specifically see Table 1.
The dimethicone of table 1 emulsification different viscosities
Embodiment 7
In the emulsification still, add 20 parts of modified silicon oils, and the organic silicon surfactant of 6 parts of embodiment 1 gained, after stirring, the about 6 parts of distilled water of disposable adding (or purified water) continue fully to mix, and this moment, system was transparent paste.Under stirring condition, slowly add remaining 68 parts of water subsequently, can obtain the milky white liquid of blueing.2500r/min * 15min is centrifugal, and is not stratified.Specifically see Table 2.
The modified silicon oil that table 2 emulsification is different
Embodiment 8
In the emulsification still, add 20 parts of silicone oil, and the organic silicon surfactant of 7 parts of embodiment 4 gained, after stirring, the about 5 parts of distilled water of disposable adding (or purified water) continue fully to mix, and this moment, system was transparent paste.Under stirring condition, slowly add remaining 68 parts of water subsequently, can obtain the milky white liquid of blueing.2500r/min * 15min is centrifugal, and is not stratified.Specifically see Table 3.
The silicone oil that table 3 emulsification is different
Claims (8)
1. an organic silicon surfactant is characterized in that, has suc as formula structure shown in (I):
Wherein, c is non-vanishing; A, b, c are integer and 10＜a+b+c＜200; M=0～40; N=0～30; X=3～30; X, m, n is integer, and m, and n is not 0 simultaneously; R is C
6～20Straight chain or isomery chain alkyl, or be alkyl phenyl; R ' is H, CH
3, C
2H
5, C
3H
7, C
4H
9
2. organic silicon surfactant according to claim 1 is characterized in that described a=0～150; B=0～60; C=1～60.
3. organic silicon surfactant according to claim 1 is characterized in that described a=1～60; B=1～20; C=1～20; A, b, c are integer and 20＜a+b+c＜100; M=5～15; N=6～20; X=6～12; X, m, n is integer; R is C
8～16Straight chain or isomery chain alkyl.
4. the preparation method of claim 1,2 or 3 described organic silicon surfactants, it is characterized in that, the allyl polyether and the containing hydrogen silicone oil that comprise the steps: to have formula (III) structure or formula (II), formula (III) structure add in the reactor, under the protection of nitrogen atmosphere, stirring is warming up to 80～100 ℃, adds chloroplatinic acid-isopropyl alcohol catalyst, continues to be heated to 110～180 ℃ of reactions, become transparent until system, obtain described organic silicon surfactant;
5. claim 1,2 or 3 application of described organic silicon surfactant in emulsifying agent.
6. application as claimed in claim 5 is characterized in that, the emulsifying agent that described organic silicon surfactant is filled a prescription as O/W type silicone oil emulsion separately.
7. application as claimed in claim 5 is characterized in that, described organic silicon surfactant is during as the emulsifying agent of O/W type silicone oil emulsion prescription, and its consumption is organic silicon surfactant by mass ratio: silicone oil=1: 2～6.
8. application as claimed in claim 5 is characterized in that, described organic silicon surfactant is during as the emulsifying agent of cream frost prescription, and its consumption is organic silicon surfactant by mass ratio: treat emulsification system=1: 5～9.
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|---|---|---|---|
| CN201110446125.3A CN103182271B (en) | 2011-12-27 | 2011-12-27 | A kind of organic silicon surfactant and its preparation method and application |
| PCT/CN2011/084992 WO2013097167A1 (en) | 2011-12-27 | 2011-12-30 | Silicone surfactant, and preparation method and use thereof |
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|---|---|---|---|
| CN201110446125.3A CN103182271B (en) | 2011-12-27 | 2011-12-27 | A kind of organic silicon surfactant and its preparation method and application |
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| CN103182271B CN103182271B (en) | 2015-10-28 |
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| CN103342818A (en) * | 2013-07-16 | 2013-10-09 | 扬州晨化科技集团有限公司 | Preparation method of polyether modified polysiloxane foam stabilizer |
| CN105199111A (en) * | 2015-10-22 | 2015-12-30 | 烟台德邦先进硅材料有限公司 | Preparation method of organosilicone surfactant for polyurethane flexible foams |
| CN106687508A (en) * | 2014-07-23 | 2017-05-17 | 道康宁公司 | Silicone emulsions |
| CN108623810A (en) * | 2018-05-11 | 2018-10-09 | 广东工业大学 | A kind of organosilicon crosslinked polymer and its preparation method and application |
| CN111040188A (en) * | 2019-11-29 | 2020-04-21 | 湖北新四海化工股份有限公司 | Organic silicon emulsifier and preparation method thereof |
| CN112574423A (en) * | 2020-11-30 | 2021-03-30 | 山东大易新产业技术研究院有限公司 | Low-molecular organosilicon surfactant for contact killing of phytophagous thrips |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103182271B (en) | 2015-10-28 |
| WO2013097167A1 (en) | 2013-07-04 |
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Effective date of registration: 20170427 Address after: 511340, Guangzhou, Zengcheng, Xintang town Yonghe River Road, South Hill, building technology, building 15, No., building 6 Patentee after: Guangzhou BioMax Pharmaceutical Co., Ltd. Address before: 510620 Guangdong, Guangzhou, Lin and West Road, No. 161 Thai International Plaza, tower B, building 15 Patentee before: Guangdong Biaomei Silicon and Fluoride New Materials Co., Ltd. |