CN103275324B - Alkynyl diol ethyl oxide polyether or alkynyl diol propyl oxide polyether co-modified polysiloxane and preparation method thereof - Google Patents
Alkynyl diol ethyl oxide polyether or alkynyl diol propyl oxide polyether co-modified polysiloxane and preparation method thereof Download PDFInfo
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Abstract
The invention relates to alkynyl diol ethyl oxide polyether or alkynyl diol propyl oxide polyether co-modified polysiloxane, wherein the molecular structure of the alkynyl diol ethyl oxide polyether or alkynyl diol propyl oxide polyether co-modified polysiloxane is shown in the specification. The alkynyl diol ethyl oxide polyether or alkynyl diol propyl oxide polyether co-modified polysiloxane provided by the invention has the advantages of low surface tension, efficient wetting power, low foam/foam inhibition performance and stronger emulsifying property.
Description
Technical field
The invention belongs to a kind of alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane and method for making.
Background technology
As everyone knows, Siloxane-Oxyalkylene Copolymers commonly use end containing unsaturated double-bond polyethers with containing the polysiloxane of reactive hydrogen under catalyst action, synthesized by addition reaction of silicon with hydrogen.For Siloxane-Oxyalkylene Copolymers, its existing preparation method, a kind ofly the polyether modified silicon oil of ultra-low surface tension and the method for synthesis technique thereof is prepared as Chinese patent CN 101434615 B reports, the method of being carried out Si―H addition reaction by allyl polyether and Methyl Hydrogen Polysiloxane Fluid obtains product, its contrivance has ultra-low surface tension, but the more impact of foam uses.On the other hand Chinese patent CN 102145267 A reports a kind of method preparing polyfunctional surfactant based on alkyne diol b-oxide, its contrivance alkyne diol b-oxide has low bubble, the dynamic surface tension of effective reduction aqueous based systems, but equilibrium surface tension is higher.
The novel alkyne diol b-oxide polyethers that the while that the present invention being lower with a kind of surface tension of polysiloxane Reactive Synthesis containing reactive hydrogen by alkyne diol b-oxide or alkyne diol propoxide, the end polyethers containing unsaturated double-bond, foam is less or alkyne diol propoxide polyethers comodified polysiloxane have no report.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a kind of nontoxic, preparation technology succinct and be easy to industrialized alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane and preparation method.
The molecular structural formula of alkyne diol b-oxide polyethers of the present invention or alkyne diol propoxide polyethers comodified polysiloxane is as follows:
Alkyne diol b-oxide polyethers prepared by the present invention described above or alkyne diol propoxide polyethers comodified polysiloxane are viscosity is 40-800 mPas liquid, and the micelle-forming concentration of its aqueous solution is 40-500mg/L, and lowest surface tension is 20-29mN/m; The minimal contact angle of the aqueous solution on ptfe surface of alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane is 15-45 °, and the minimal contact angle in paraffin surface is 5-35 °.Alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane have low surface tension, efficient wetting power, low bubble/suds suppressing properties and stronger emulsifying property.
The preparation method of novel alkyne diol b-oxide polyethers of the present invention described above or alkyne diol propoxide polyethers comodified polysiloxane comprises the following steps:
By alkyne diol b-oxide or alkyne diol b-oxide, end contains the polyethers of unsaturated double-bond and the polysiloxane containing reactive hydrogen is raw material, under solvent and catalysts conditions, in 40-300 DEG C of reaction 0.5-48 hour; Wherein the mol ratio of alkyne diol b-oxide or alkyne diol propoxide, the polyethers of end containing unsaturated double-bond and the polysiloxane containing reactive hydrogen is 0.1-20: 0.1-20: 1, after reaction terminates, steaming desolventizes and low boiling point component, obtains alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane.
In step described above, temperature of reaction is preferably 40-240 DEG C.In step, the mol ratio of alkyne diol b-oxide or alkyne diol propoxide, the polyethers of end containing unsaturated double-bond and the polysiloxane containing reactive hydrogen is preferably 0.1-10: 0.1-10: 1.
The molecular structural formula of the polysiloxane containing reactive hydrogen as above is:
Polysiloxane containing reactive hydrogen as above comprises octamethylcyclotetrasiloxane or Silicon Containing Hydrogen wet goods.
End as above containing the molecular structural formula of the polyethers of unsaturated double-bond is:
End as above comprises allyl polyether, methyl blocking allyl polyether or acetyl blocked allyl polyether etc. containing the polyethers of unsaturated double-bond.
The molecular structural formula of alkyne diol b-oxide as above or alkyne diol propoxide is:
Alkyne diol ethoxylate as above comprises butynediol monosubstituted ethoxy ether or butynediol diethoxy ether, and alkyne diol propoxide comprises butynediol list propoxy-or butynediol dipropoxy ether etc.
Solvent as above is Virahol, ethanol, methyl alcohol, dioxane or toluene etc.
Catalyzer described above can comprise: one or more in Platinic chloride, ruthenium chloride, Karst (Karstedt) platinum catalyst.
The consumption of catalyzer as above, in Pt contained in catalyzer or/and Ru, its consumption is three kinds of raw material gross weights: catalyzer=1Kg: 5-300mg.
Novel alkyne diol b-oxide polyethers prepared by the present invention or alkyne diol propoxide polyethers comodified polysiloxane have low surface tension, efficient wetting power, low bubble/suds suppressing properties and stronger emulsifying property.Can as efficient wetting agent, sprawl auxiliary agent etc. and apply in agricultural chemicals, household chemicals field, coating, cloth printing ink.
The present invention compared with prior art tool has the following advantages:
1, the target compound prepared by the present invention not only has the excellent surface properties of traditional organic silicon surfactant, simultaneously owing to organo-siloxane having accessed acetylenic diols compound, makes it have froth breaking, press down the effects such as bubble.
2, the alkyne diol b-oxide among the raw material that the target compound prepared by the present invention is used and alkyne diol propoxide are the derived product of coal chemical industry.And the raw material of existing synthesis of surfactant is mostly from the derived product of petroleum resources.China is coal big country, and therefore raw material is sufficient.
The aqueous solution of the target compound 3, prepared by the present invention has spreading wetting performance, and containing double bond in its molecular structure, can improve the consistency of itself and the application system such as coating, cloth printing ink.
4, containing double bond in the target compound prepared by the present invention, can be used as active function groups and prepare other tensio-active agent.
5, the target compound prepared by the present invention has low surface tension, efficient wetting power, low bubble/suds suppressing properties and stronger emulsifying property.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of product butynediol list propoxy-ether polyethers comodified polysiloxane in the embodiment of the present invention 3;
Fig. 2 is the infrared spectrogram of product butynediol list propoxy-ether polyethers comodified polysiloxane in the embodiment of the present invention 3.
Embodiment
Below in conjunction with example, the present invention is made an explanation.
Embodiment 1
First 16.58Kg allyl polyether (APEO-7), 1.87Kg butynediol monosubstituted ethoxy ether and 32.05Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 0.52%) join in reactor, add Platinic chloride and ruthenium chloride again and (be respectively 50mg/kg in Pt and Ru quality contained in catalyzer with the ratio of three kinds of raw material total masses, 50mg/kg), solvent is made with Virahol, under temperature is 130 DEG C of conditions, N
2the lower reaction of protection 7 hours.Steaming desolventizes Virahol and low boiling component, and finally obtaining amber transparent viscous liquid product is butynediol monosubstituted ethoxy ether polyethers comodified polysiloxane, and its viscosity is 566mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 22mN/m.The micelle-forming concentration of the aqueous solution is 387mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 35 ° simultaneously, and the minimal contact angle in paraffin surface is 20 °.
Embodiment 2
First 24.83Kg methyl blocking allyl polyether, 7.61Kg butynediol diethoxy ether and 16.76Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 1.32%) join in reactor, add Karst (Karstedt) platinum catalyst (counting 20mg/kg with the ratio of three kinds of raw material total masses with Pt quality contained in catalyzer) again, with methanol as solvent, under temperature is 240 DEG C of conditions, N
2the lower reaction of protection 16 hours.Steaming desolventizes methyl alcohol and low boiling component, and the viscous liquid product finally obtaining yellowish brown clarification is butynediol diethoxy ether polyethers comodified polysiloxane, and its viscosity is 279mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 20mN/m.Micelle-forming concentration is 203mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 20 ° simultaneously, and the minimal contact angle in paraffin surface is 5 °.
Embodiment 3
First 6.47Kg methyl blocking allyl polyether, 14.98Kg butynediol list propoxy-ether and 19.43Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 0.51%) join in reactor, add Platinic chloride and ruthenium chloride solution again and (be respectively 80mg/Kg in Pt and Ru quality contained in catalyzer with the ratio of three kinds of raw material total masses, 80mg/Kg) be catalyzer, solvent is made with Virahol, under temperature is 170 DEG C of conditions, N
2the lower reaction of protection 13 hours.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product finally obtaining orange-yellow clarification is butynediol list propoxy-ether polyethers comodified polysiloxane, and its viscosity is 367mPas.Hydrogen nuclear magnetic resonance spectrometer and infrared spectrometer is utilized to carry out structural characterization (see accompanying drawing 1 to product, 2), by resolving position and the size at the peak in hydrogen nuclear magnetic resonance spectrogram and infrared spectrum, show that synthesized product is target product butynediol list propoxy-ether polyethers comodified polysiloxane.The surface tension recording its aqueous solution by K-12 surface tension instrument is 23mN/m.Micelle-forming concentration is 487mg/L.Its aqueous solution is 45 ° at the minimal contact angle of ptfe surface simultaneously, is 35 ° at the minimal contact angle of paraffin.
Embodiment 4
First acetyl blocked for 22.65Kg allyl polyether; 6.81Kg butynediol dipropoxy ether and 10.63Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 1.57%) join in reactor; add Karstedt platinum catalyst (being respectively 150mg/kg with the ratio of three kinds of raw material total masses in Pt quality contained in catalyzer) again; with ethanol as solvent; under temperature is 150 DEG C of conditions, N
2the lower reaction of protection 6 hours.Steaming desolventizes ethanol and low boiling component, and the viscous liquid product finally obtaining amber clarification is butynediol dipropoxy ether polyethers comodified polysiloxane, and its viscosity is 794mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 24mN/m.Micelle-forming concentration is 295mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 25 ° simultaneously, and the minimal contact angle in paraffin surface is 10 °.
Embodiment 5
First 6.65Kg allyl polyether (APEO-7), 26.81Kg butynediol dipropoxy ether and 10.63Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 1.57%) join in reactor, add chloroplatinic acid catalyst (being respectively 5mg/kg with the ratio of three kinds of raw material total masses in Pt quality contained in catalyzer) again, solvent is made with Virahol, under temperature is 40 DEG C of conditions, N
2the lower reaction of protection 48 hours.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product finally obtaining faint yellow clear is butynediol dipropoxy ether polyethers comodified polysiloxane, and its viscosity is 163mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 22mN/m.Micelle-forming concentration is 188mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 15 ° simultaneously, and the minimal contact angle in paraffin surface is 5 °.
Embodiment 6
First acetyl blocked for 15.84g allyl polyether, 10.61Kg butynediol propoxy-ether and 23.75Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 0.57%) are joined in reactor; add chloroplatinic acid catalyst (being respectively 300mg/Kg with the ratio of three kinds of raw material total masses in Pt quality contained in catalyzer) again; solvent is made with Virahol; under temperature is 160 DEG C of conditions, N
2the lower reaction of protection 4 hours.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product finally obtaining yellow clear is butynediol propoxy-ether polyethers comodified polysiloxane, and its viscosity is 683mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 26mN/m.Micelle-forming concentration is 194mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 40 ° simultaneously, and the minimal contact angle in paraffin surface is 25 °.
Embodiment 7
First 10.82Kg methyl blocking allyl polyether, 15.64Kg butynediol propoxy-ether and 23.24Kg octamethylcyclotetrasiloxane are joined in reactor, add Karstedt platinum catalyst (scoring other 50mg/Kg with Pt quality contained in catalyzer and the ratio of three kinds of raw material total masses) again, solvent is made with epoxy six ring, under temperature is 180 DEG C of conditions, N
2the lower reaction of protection 1 hour.Steam except epoxy six ring makes solvent and low boiling component, the viscous liquid product finally obtaining yellow clear is alkyne diol propoxy-ether polyethers modification tetrasiloxane altogether, and its viscosity is 40mPas.The surface tension recording its aqueous solution by K-12 surface tension instrument is 29mN/m.Micelle-forming concentration is 40mg/L.The minimal contact angle of its aqueous solution on ptfe surface is 35 ° simultaneously, and the minimal contact angle in paraffin surface is 10 °.
Target compound synthesized by the present embodiment all uses nucleus magnetic resonance and infrared spectra to characterize, and by resolving position and the size at the peak in hydrogen nuclear magnetic resonance spectrogram and infrared spectrum, shows that synthesized product is target product.Now be described for the proton nmr spectra of product in embodiment 3 and infrared spectra collection of illustrative plates.
Claims (12)
1. alkyne diol b-oxide polyethers or an alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that the molecular structural formula of alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane is as follows:
Wherein, x, y=1-50; Z=0-100; A=1-50; B, c=0-50;
R is :-OH ,-OCH
3or
2. a kind of alkyne diol b-oxide polyethers as claimed in claim 1 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that described alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane be viscosity are 40-800mPas liquid, the micelle-forming concentration of its aqueous solution is 40-500mg/L, and lowest surface tension is 20-29mN/m; The minimal contact angle of the aqueous solution on ptfe surface of alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane is 15-45 °, and the minimal contact angle in paraffin surface is 5-35 °.
3. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 1 or 2 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that comprising the steps:
By alkyne diol b-oxide or alkyne diol propoxide, end contains the polyethers of unsaturated double-bond and the polysiloxane containing reactive hydrogen is raw material, under solvent and catalysts conditions, in 40-300 DEG C of reaction 0.5-48 hour; Wherein the mol ratio of alkyne diol b-oxide or alkyne diol propoxide, the polyethers of end containing unsaturated double-bond and the polysiloxane containing reactive hydrogen is 0.1-20: 0.1-20: 1, after reaction terminates, steaming desolventizes and low boiling point component, obtains alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane.
4. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 3 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that described temperature of reaction is 40-240 DEG C.
5. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 3 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that the mol ratio of alkyne diol b-oxide or alkyne diol propoxide, the polyethers of end containing unsaturated double-bond and the polysiloxane containing reactive hydrogen in described reaction is 0.1-10: 0.1-10: 1.
6. the preparation method of a kind of alkyne diol b-oxide polyethers as described in any one of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that the molecular structural formula of the described polysiloxane containing reactive hydrogen is:
Wherein x, y=1-50; Z=0-100.
7. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 6 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that the described polysiloxane containing reactive hydrogen is octamethylcyclotetrasiloxane.
8. the preparation method of a kind of alkyne diol b-oxide polyethers as described in any one of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that described end containing the molecular structural formula of the polyethers of unsaturated double-bond is
Wherein, R is :-OH ,-OCH
3or
a＝1―50。
9. the preparation method of a kind of alkyne diol b-oxide polyethers as described in any one of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that the molecular structural formula of described alkyne diol b-oxide or alkyne diol propoxide is:
Wherein, R is :-OH ,-OCH
3or
b,c＝0―50。
10. the preparation method of a kind of alkyne diol b-oxide polyethers as described in any one of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that described solvent is Virahol, ethanol, methyl alcohol, dioxane or toluene.
The preparation method of 11. a kind of alkyne diol b-oxide polyethers as described in any one of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, is characterized in that described catalyzer is one or more in Platinic chloride, ruthenium chloride, Karst platinum catalyst.
The preparation method of 12. a kind of alkyne diol b-oxide polyethers as described in any one of claim 11 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that the consumption of described catalyzer, in Pt contained in catalyzer or/and Ru, its consumption is three kinds of raw material gross weights: catalyzer=1Kg: 5-300mg.
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