CN109225058A - A kind of silicone surfactant and preparation method thereof that alkynol alkoxide compound is modified - Google Patents
A kind of silicone surfactant and preparation method thereof that alkynol alkoxide compound is modified Download PDFInfo
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- CN109225058A CN109225058A CN201810878790.1A CN201810878790A CN109225058A CN 109225058 A CN109225058 A CN 109225058A CN 201810878790 A CN201810878790 A CN 201810878790A CN 109225058 A CN109225058 A CN 109225058A
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Abstract
The invention discloses a kind of modified silicone surfactants of alkynol alkoxide compound, the main chain of molecular structure is the hydrogen-containing siloxane base for losing hydrogen atom, side chain is the alkynol alkoxide compound base after alkynyl and a hydrogen addition, and main side interchain takes Si-C chemical bond to be connected；Synthetic method are as follows: vacuum, it is solvent-free, have catalyst under conditions of, hydrosilylation occurs for alkynol alkoxide compound and hydrogen-containing siloxane, obtains product；The molar ratio of alkynol alkoxide compound and hydrogen-containing siloxane is 1.15:1, and reaction temperature is 80 DEG C~110 DEG C, and reaction vacuum degree is 200~750mmHg, reaction time 3.5h, appropriate reaction suppressor.The advantages that surface-active has both low static and dynamic surface tension, low bubble, stability is high；Preparation method be different from conventional preparation techniques, the use of carboxylic acid or its salt prevent the hydroxyl of alkynol ether and/or copolymer formed acetal, eliminate solvent in common process, acetal processing and solvent dissolution and etc., simplify technique, reduce costs.
Description
Technical field
The present invention relates to the modified siloxanes of technical field of surfactant more particularly to a kind of alkynol alkoxide compound
Surfactant and preparation method thereof.
Background technique
Polyether modified siloxane surfactant is most widely used organic silicon surfactant in the industry at present.It has
Having trisiloxane surfactant, often the interfacial tensions of oil-water interfaces is effectively reduced in some, has in low energy hydrophobic surface " super
The features such as spreadability ".Due to there is thermally labile, weak to oil/water interface emulsification ability and when using concentration in the application
The disadvantages of foam is more.Therefore, the application range of polyether modified siloxane surfactant is limited to a certain extent.This
Outside, the raw material sources of synthesizing polyether are in non-renewable petroleum-based energy.
Acetylenic diols surfactant is a kind of multifunctional novel nonionic surfactant, it have wetting, dispersion,
Defoaming reduces the application performances such as water sensitivity.Its representative product has American Air Products and Chemical
Company the eighties in last century later development Surfynol series and the nineties exploitation Dynol series of surfactants.
Due to containing three keys in molecular structure, so that acetylenic diols surfactant can be used as the original for synthesizing other surfactants
Material.
United States Patent (USP) (applying date: 1997-08-08, publication number: US5869727A) discloses a kind of organic silicon modified by polyether
Manufacturing process, there is illustrated the graft products --- Siloxane-Oxyalkylene Copolymers can effectively reduce the surface of system
Power, so as to achieve the effect that wetting and levelling, but such surfactant has the function of very strong foam stabilizing simultaneously, however
Bubble again can produce serious influence to the surface effect of leather；Also, United States Patent (USP) (applying date: 1994-03-08, it is open
Number: US5391697A) disclose organic silicon modified by polyether its static surface tension of oxygen alkanes surfactant and dynamic surface
Gap edge is very big, and under the conditions of high speed dynamic construction technology, wettability is decreased obviously；United States Patent (USP) (applying date:
2001-12-18, publication number: US6455234B1), Japan Patent (applying date: 1990-07-17, publication number: JP2636954B2)
Reporting acetylenic diols ethoxylated surfactant can reduce dynamic surface tension, while have low foaming characteristic,
Under the conditions of the dynamic construction technology of high speed, there are good wetability and formula to use wide in range property.But such surfactant its
Static surface tension value is very high, this is just difficult to the substrate for soaking those more low-surface-energies.
Summary of the invention
Based on the above the deficiencies in the prior art, technical problem solved by the invention is to provide a kind of alkynol alkoxylate
Polymer modified silicone surfactant and preparation method thereof, the modified silicone surfactant of the alkynol alkoxide compound
It has both low static and dynamic surface tension, low bubble, the advantages that stability is high, passes through the alkynol alkoxide compound of different molecular weight
And the matched combined of hydrogen-containing siloxane, the surfactant of the different application characteristics such as available wetting, defoaming.The preparation side
For method compared with conventional preparation techniques, the use of carboxylic acid or salt prevents the hydroxyl of alkynol ether and/or copolymer from forming acetal, eliminates
Solvent in common process, acetal processing and solvent dissolution step use, simplify technique, reduce costs.
In order to solve the above technical problem, the present invention provides a kind of modified siloxane surface of alkynol alkoxide compound is living
Property agent, general molecular formula such as formula:
Wherein, m and n is the siloxy group degree of polymerization, is 0~8 integer；
X, o is the degree of polymerization of ethylene oxide, and y, p are the degree of polymerization of propylene oxide, and x+y, o+p are 1~10 integer.
As a preferred embodiment of the above technical solution, exhaust gas recovery system provided by the invention further comprises following technical characteristic
Some or all of:
As an improvement of the above technical solution, the general formula of molecular structure of the hydrogen-containing siloxane is as follows:
Its molecular weight is 400~2000.
As an improvement of the above technical solution, the molecular weight of the hydrogen-containing siloxane is 500~1000.
As an improvement of the above technical solution, the general formula of molecular structure of the alkynol alkoxide compound is as follows:
Its molecular weight is 200~2000.
As an improvement of the above technical solution, the molecular weight of the alkynol alkoxide compound is 200~600.
Technical problem of the invention can also be solved by following scheme: a kind of siloxanes that alkynol alkoxide compound is modified
The preparation method of surfactant, vacuum, it is solvent-free, have catalyst under conditions of, alkynol alkoxide compound and Silicon Containing Hydrogen
Hydrosilylation occurs for oxygen alkane, obtains product；Wherein, the molar ratio 1.15 of alkynol alkoxide compound and hydrogen-containing siloxane:
1, catalyst H2PtCl6, dosage with Pt mass/(alkynol alkoxide compound just and hydrogen-containing siloxane gross mass)=50
~200ppm is meter, and reaction temperature is 80 DEG C~110 DEG C, and reaction vacuum degree is 200~750mmHg, reaction time 3.5h, is fitted
Quantitative response inhibitor.
As an improvement of the above technical solution, the reaction suppressor includes carboxylic acid or its esters compound.
As an improvement of the above technical solution, the catalyst is diluted using aqueous isopropanol.
Compared with prior art, technical solution of the present invention has the following beneficial effects:
(1) the modified silicone surfactant of alkynol alkoxide compound of the present invention has both static and dynamic surface
The advantages that tension is low, low bubble property, high stability, super wetability, the bubble-related issues in effective improvement system；
(2) the modified silicone surfactant of alkynol alkoxide compound of the present invention has good compatible with system
Property, the problem of being not in pollution printed board or cause residual；
(3) the modified silicone surfactant of alkynol alkoxide compound of the present invention is applicable to the print of strong basicity
The every field such as wiring board developer solution processed, cleaning solution, pesticide wetting agent；
(4) it is reacted, can be obtained with the matched combined of hydrogen-containing siloxane by the alkynol alkoxide compound of different molecular weight
To the surfactant with different applications characteristics such as wetting, defoamings；
(5) preparation method and tradition of the modified silicone surfactant of alkynol alkoxide compound of the present invention are made
Standby technique compares: using the solvent-free method of vacuum in the present invention, the use of carboxylic acid or its salt can prevent alkynol ether and/or be total to
The hydroxyl of polymers forms acetal, eliminates the use of solvent in common process, acetal processing and solvent dissolution step, simplifies work
Skill reduces costs, and achieves good environmental benefit and economic benefit；
The above description is only an overview of the technical scheme of the present invention, in order to better understand the technical means of the present invention,
And it can be implemented in accordance with the contents of the specification, and in order to allow above and other objects, features and advantages of the invention can
It is clearer and more comprehensible, below in conjunction with preferred embodiment, detailed description are as follows.
Detailed description of the invention
In order to illustrate the technical solution of the embodiments of the present invention more clearly, the attached drawing to embodiment is simply situated between below
It continues.
Fig. 1 is butynediols diethoxy compound trisiloxanes (TBEO) synthetic route chart of the present invention；
Fig. 2 is silicon hydrogen content test device figure of the present invention；
Fig. 3 is the nuclear magnetic spectrogram of BEO used in the present invention；
Fig. 4 is the nuclear magnetic spectrogram of the modified silicone surfactant of alkynol alkoxide compound prepared by the present invention.
Specific embodiment
The following detailed description of a specific embodiment of the invention, as part of this specification, by embodiment come
Illustrate that the principle of the present invention, other aspects of the present invention, feature and its advantage will become apparent by the detailed description.
Embodiment 1
The preparation flow of the modified silicone surfactant of the alkynol alkoxide compound is as shown in Figure 1, reaction is former
Expect 1,1,1,3,5,5,5-- heptamethyltrisiloxane (HMTS) and butynediols ethyoxyl ether (BEO), passes through hydrosilylation
Method synthesis.
Concrete operations are as follows: by raw material HMTS (profit standing grain organosilicon) and BEO (Wuhan Losec Specialty Chemical) rubbing by 1.13:1
You feed intake at ratio, catalyst H2PtC16By 100ppm, (its dosage is with Pt mass/alkynol alkoxide compound and hydrogen-containing siloxane
Gross mass be meter), reaction suppressor carboxylic acid sodium is added equipped with mechanical stirring device, condensation reflux unit and thermometer
In 250mL four round flask, wherein the additional amount of reaction suppressor accounts for the 0.05% of total reactant quality percentage, then takes out
Vacuum, vacuum degree is in 500mmHg, and then under agitation, after oil bath heating is reacted 3.5 hours, last cooling discharge is obtained
The modified silicone surfactant (TBEO) of product alkynol alkoxide compound.Measuring Si―H addition reaction conversion ratio is 95%, face
Color: transparent water-white.
Embodiment 2
Raw material HMTS (profit standing grain organosilicon) and BEO (Wuhan Losec Specialty Chemical) are thrown by the molar ratio of 1.13:1
Material, catalyst H2PtC16By 50ppm, (its dosage is with the gross mass of Pt mass/alkynol alkoxide compound and hydrogen-containing siloxane
Meter), account for overall reaction substance mass percent 0.05% reaction suppressor carboxylic acid sodium be added equipped with mechanical stirring device, condensation
In the 250mL four round flask of reflux unit and thermometer, vacuumize, vacuum degree is in 700mmHg, then in stirring condition
Under, after oil bath heating is reacted 3.5 hours, last cooling discharge obtains the modified siloxanes table of product alkynol alkoxide compound
Face activating agent (TBEO).Measuring Si―H addition reaction conversion ratio is 85%, and color is transparent water-white.
Embodiment 3
Raw material HMTS (profit standing grain organosilicon) and BEO (Wuhan Losec Specialty Chemical) are thrown by the molar ratio of 1.13:1
Material, catalyst H2PtC16By 200ppm, (its dosage is with the gross mass of Pt mass/alkynol alkoxide compound and hydrogen-containing siloxane
Meter), account for overall reaction substance mass percent be 0.05% reaction suppressor carboxylic acid sodium be added equipped with mechanical stirring device, condensation
In the 250mL four round flask of reflux unit and thermometer, vacuumize, vacuum degree is in 500mmHg, then in stirring condition
Under, after oil bath heating is reacted 3.5 hours, last cooling discharge obtains product alkynol alkoxide compound test silicon hydrogen conversion ratio
It is 88%.Color yellow.
In terms of silicon hydrogen conversion ratio, the dosage of larger catalyst does not promote conversion ratio, and there are also deepened for color.
Fig. 3 is the nuclear-magnetism figure of BEO, and Fig. 4 is the spectrum of the modified silicone surfactant of product alkynol alkoxide compound
There is a new absorption peak at (4.1ppm) from the spectrogram 4 that can be seen that product in Fig. 3 and Fig. 4 in figure, which is
The absorption peak of C=C-H in TBEO, and the silicon hydrogen peak in seven methyl obviously disappears, and illustrates to have carried out hydrosilylation, carbon
The disappearance of three key of carbon illustrates that acetylene bond and si-h bond have carried out addition reaction.
The measurement of conversion ratio in reaction process: anti-to judge by the content of measurement reaction raw materials HMTS in the reaction system
The conversion ratio answered.Since Si -- H can react with the aqueous solution of KOH in HMTS, and generate hydrogen.Therefore, Ke Yitong
It crosses accurate measurement and reacts released hydrogen volume, to calculate the conversion ratio of HMTS, measurement device figure is as shown in Figure 2.Industry
The upper progress that hydrosilylation is usually monitored using the method.
Performance test:
Performance survey is carried out to the modified silicone surfactant of alkynol alkoxide compound prepared by above-described embodiment
Examination, specific as follows:
1. surface tension
Laboratory apparatus: surface tension instrument (PROCESSOR TENSIOMETER K-12, German Kriiss company)；Dynamic table
Face tensiometer (BP 100, German Kriiss company).
In order to study the surface-active of TBEO in aqueous solution, its surface in aqueous solution is determined by hanging ring method
Power.
1:25 DEG C of table, 0.1% each surfactant work static aqueous solution and dynamic surface tension
From table 1 it follows that the surface tension of water is reduced to 26mN/m or so by TBEO, it is less than common acetylenic glycols
(Syfynol420) class surfactant is all methyl for trisiloxane surfactant molecule hydrophobic grouping, so that three silicon
Oxygen alkane surfactant molecule the surface of water can close-packed arrays, and siloxanes trunk is only simple as a combination
The flexible frame of methyl, so that surfactant molecule obtains highdensity methyl accumulation on the surface of water.And for acetylenic glycols
Class surfactant, mainly methylene in the hydrophobic grouping in molecule, therefore in gas-liquid interface loose arrangement.Due to table
Methyl surface-active in the activating agent hydrophobic grouping of face is greater than methylene.So trisiloxane surfactant reduces the table of water
Face tension ability is greater than acetylenic diols surfactant.Therefore the surfactant has low static dynamic surface tension simultaneously
Characteristic.
2. foaming properties
This experiment measures various concentration under the conditions of 25 DEG C, through improved Ross-Miles method (GB/T 7462-94)
The foaming properties of TBEO solution.Its measurement result is listed in table 2.From this table it is found that TBEO solution concentration be 0.05wt% and
Substantially foam is not generated when 0.1Wt%.The polyether modified siloxane solution of 0.1Wt% can generate foam and foam stabilizing.It therefore can
See that TBEO aqueous solution has low bubble property.
2 foaming properties of table
| Sample | Initial foam height | Foam height when 5min |
| TBEO (0.05%) aqueous solution | 0 | 0 |
| TBEO (0.1%) aqueous solution | 0 | 0 |
| DC65 (0.1%) aqueous solution | 95 | 90 |
By above-mentioned performance test, demonstrate imagination when original structure design, i.e., low bubble wetting, low static state and dynamic
Surface tension.
The bound of each raw material cited by the present invention and each raw material of the present invention, section value and technological parameter
Bound, the section value of (such as temperature, time) can realize the present invention, embodiment numerous to list herein.
The above is a preferred embodiment of the present invention, cannot limit the right model of the present invention with this certainly
It encloses, it is noted that for those skilled in the art, without departing from the principle of the present invention, may be used also
To make several improvement and variation, these, which improve and change, is also considered as protection scope of the present invention.
Claims (9)
1. a kind of modified silicone surfactant of alkynol alkoxide compound, which is characterized in that general molecular formula such as formula (I):
The main chain of molecular structure is the hydrogen-containing siloxane base for losing hydrogen atom, and side chain is the alkynol alkane after alkynyl and a hydrogen addition
Oxo-compound base, main side interchain take Si-C chemical bond to be connected；
Wherein, m and n is the siloxy group degree of polymerization, is 0~8 integer；
X, o is the degree of polymerization of ethylene oxide, and y, p are the degree of polymerization of propylene oxide, and x+y, o+p are 1~10 integer.
2. a kind of modified silicone surfactant of alkynol alkoxide compound as described in claim 1, which is characterized in that
The general formula of molecular structure of the hydrogen-containing siloxane is as follows:
Its molecular weight is 400~2000.
3. a kind of modified silicone surfactant of alkynol alkoxide compound as claimed in claim 2, which is characterized in that
The molecular weight of the hydrogen-containing siloxane is 500~1000.
4. a kind of modified silicone surfactant of alkynol alkoxide compound as described in claim 1, which is characterized in that
The general formula of molecular structure of the alkynol alkoxide compound is as follows:
Its molecular weight is 200~2000.
5. a kind of modified silicone surfactant of alkynol alkoxide compound as claimed in claim 4, which is characterized in that
The molecular weight of the alkynol alkoxide compound is 200~600.
6. a kind of preparation method of the modified silicone surfactant of alkynol alkoxide compound, which is characterized in that vacuum,
It is solvent-free, have catalyst under conditions of, hydrosilylation occurs for alkynol alkoxide compound and hydrogen-containing siloxane, is produced
Object；Wherein, the molar ratio 1.15:1 of alkynol alkoxide compound and hydrogen-containing siloxane, reaction temperature are 80 DEG C~110 DEG C, reaction
Vacuum degree is 200~750mmHg, reaction time 3.5h, appropriate reaction suppressor.
7. a kind of preparation method of the modified silicone surfactant of alkynol alkoxide compound as claimed in claim 6,
It is characterized in that, the catalyst is H2PtC16, dosage is total with Pt mass/alkynol alkoxide compound and hydrogen-containing siloxane
Quality=50~200ppm is meter.
8. a kind of preparation method of the modified silicone surfactant of alkynol alkoxide compound as claimed in claim 6,
It is characterized in that, the reaction suppressor includes carboxylic acid or metal carboxylate compound.
9. a kind of preparation method of the modified silicone surfactant of alkynol alkoxide compound as claimed in claim 6,
It is characterized in that, the catalyst is diluted using aqueous isopropanol.
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Cited By (6)
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| CN110041356A (en) * | 2019-03-27 | 2019-07-23 | 浙江润禾有机硅新材料有限公司 | A kind of twin structural polyether siloxanes and preparation method |
| CN112280046A (en) * | 2020-11-13 | 2021-01-29 | 杭州崇耀科技发展有限公司 | Preparation method of alkyne bond-containing polyether modified organic silicon |
| CN113461948A (en) * | 2021-07-12 | 2021-10-01 | 武汉辰语达科技有限公司 | Flash rust prevention agent and preparation method and application thereof |
| CN113816983A (en) * | 2021-11-04 | 2021-12-21 | 枣阳市华威硅氟材料有限公司 | Method for catalyzing hydrosilylation reaction by using p-cymene ruthenium dichloride dimer |
| CN114316600A (en) * | 2021-07-12 | 2022-04-12 | 南京瑞思化学技术有限公司 | Preparation method of organic silicon composition |
| CN115445251A (en) * | 2022-09-02 | 2022-12-09 | 南京林业大学 | Butynediol ether modified organic silicon defoaming agent and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041356A (en) * | 2019-03-27 | 2019-07-23 | 浙江润禾有机硅新材料有限公司 | A kind of twin structural polyether siloxanes and preparation method |
| CN112280046A (en) * | 2020-11-13 | 2021-01-29 | 杭州崇耀科技发展有限公司 | Preparation method of alkyne bond-containing polyether modified organic silicon |
| CN113461948A (en) * | 2021-07-12 | 2021-10-01 | 武汉辰语达科技有限公司 | Flash rust prevention agent and preparation method and application thereof |
| CN114316600A (en) * | 2021-07-12 | 2022-04-12 | 南京瑞思化学技术有限公司 | Preparation method of organic silicon composition |
| CN114316600B (en) * | 2021-07-12 | 2023-04-11 | 南京瑞思化学技术有限公司 | Preparation method of organic silicon composition |
| CN113461948B (en) * | 2021-07-12 | 2023-09-29 | 武汉辰语达科技有限公司 | Flash rust prevention agent and preparation method and application thereof |
| CN113816983A (en) * | 2021-11-04 | 2021-12-21 | 枣阳市华威硅氟材料有限公司 | Method for catalyzing hydrosilylation reaction by using p-cymene ruthenium dichloride dimer |
| CN115445251A (en) * | 2022-09-02 | 2022-12-09 | 南京林业大学 | Butynediol ether modified organic silicon defoaming agent and preparation method thereof |
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Application publication date: 20190118 |