CN103275324A - 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, the polysiloxane that polyether-modified polysiloxane end commonly used contains the polyethers of unsaturated double-bond and contains reactive hydrogen synthesizes by addition reaction of silicon with hydrogen under catalyst action.For polyether-modified polysiloxane, its existing preparation method, reported a kind of method for preparing polyether modified silicon oil and the synthesis technique thereof of ultra-low surface tension as Chinese patent CN 101434615 B, the method of carrying out the addition of silicon hydrogen by allyl polyether and Methyl Hydrogen Polysiloxane Fluid obtains product, its contrivance has ultra-low surface tension, but the more influence of foam is used.Chinese patent CN 102145267 A have reported that a kind of alkyne diol b-oxide for preparing is the method for the multifunctional meter surface-active agent on basis on the other hand, its contrivance alkyne diol b-oxide has low bubble, effectively reduce the dynamic surface tension of aqueous based systems, but equilibrium surface tension is higher.
Less novel alkyne diol b-oxide polyethers or the alkyne diol propoxide polyethers comodified polysiloxane of the present invention contains unsaturated double-bond by alkyne diol b-oxide or alkyne diol propoxide, end polyethers and the low foam simultaneously of the synthetic a kind of surface tension of polysiloxane reaction that contains reactive hydrogen do not appear in the newspapers.
Summary of the invention
The objective 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:
Prepared alkyne diol b-oxide polyethers or the alkyne diol propoxide polyethers comodified polysiloxane of the present invention is that viscosity is 40-800 mPas liquid as mentioned above, 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 on 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 or alkyne diol propoxide polyethers comodified polysiloxane may further comprise the steps as mentioned above:
The polysiloxane that is contained the polyethers of unsaturated double-bond and contained reactive hydrogen by alkyne diol b-oxide or alkyne diol b-oxide, end is raw material, under solvent and catalyzer condition, in 40-300 ℃ of reaction 0.5-48 hour; Wherein alkyne diol b-oxide or alkyne diol propoxide, the end mol ratio that contains the polyethers of unsaturated double-bond and contain the polysiloxane of reactive hydrogen is 0.1-20: 0.1-20: 1, after reaction finishes, steaming desolventizes and low boiling point component, obtains alkyne diol b-oxide polyethers or alkyne diol propoxide polyethers comodified polysiloxane.
Temperature of reaction is preferably 40-240 ℃ in the step as mentioned above.The mole proportioning that alkyne diol b-oxide or alkyne diol propoxide, end contain the polyethers of unsaturated double-bond and contain the polysiloxane of reactive hydrogen in the step is preferably 0.1-10: 0.1-10: 1.
The aforesaid molecular structural formula that contains the polysiloxane of reactive hydrogen is:
The aforesaid polysiloxane that contains reactive hydrogen comprises prestox tetrasiloxane or containing hydrogen silicone oil etc.
The molecular structural formula that aforesaid end contains the polyethers of unsaturated double-bond is:
The polyethers that aforesaid end contains unsaturated double-bond comprises allyl polyether, methyl blocking allyl polyether or acetyl blocked allyl polyether etc.
The molecular structural formula of aforesaid alkyne diol b-oxide or alkyne diol propoxide is:
Aforesaid alkyne diol ethoxylate comprises butynediol monosubstituted ethoxy ether or butynediol diethoxy ether, and the alkyne diol propoxide comprises butynediol list propoxy-or butynediol dipropoxy ether etc.
Aforesaid solvent is Virahol, ethanol, methyl alcohol, dioxane or toluene etc.
Catalyzer can comprise as mentioned above: one or more in Platinic chloride, ruthenium chloride, Karst (Karstedt) platinum catalyst.
Aforesaid catalyst consumption, or/and Ru, its consumption is three kinds of raw material gross weight: catalyzer=1Kg: 5-300mg in Pt contained in the catalyzer.
The novel alkyne diol b-oxide polyethers that the present invention is prepared or alkyne diol propoxide polyethers comodified polysiloxane have low surface tension, efficient wetting power, low bubble/suds suppressing properties and stronger emulsifying property.Can be used as efficient wetting agent, sprawl auxiliary agent etc. and in agricultural chemicals, household chemicals field, coating, cloth printing ink, use.
The present invention compared with prior art has following advantage:
1, the prepared target compound of the present invention not only has the excellent surface properties of traditional organic silicon surfactant, simultaneously owing to inserted the acetylenic diols compound on the organo-siloxane, makes it have froth breaking, presses down effect such as bubble.
2, alkyne diol b-oxide and the alkyne diol propoxide among the used raw material of the prepared target compound of the present invention is the derived product of coal chemical industry.And the synthetic raw material of existing tensio-active agent is mostly from the derived product of petroleum resources.China is coal big country, so the raw material abundance.
3, the aqueous solution of the prepared target compound of the present invention has the spreading wetting performance, and contains two keys in its molecular structure, can improve the consistency of application systems such as itself and coating, cloth printing ink.
4, contain two keys in the prepared target compound of the present invention, can be used as active function groups and prepare other tensio-active agent.
5, the prepared target compound of the present invention has low surface tension, efficient wetting power, low bubble/suds suppressing properties and stronger emulsifying property.
Description of drawings
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of product butynediol list propoxy-ether polyethers comodified polysiloxane in the embodiment of the invention 3;
Fig. 2 is the infrared spectrogram of product butynediol list propoxy-ether polyethers comodified polysiloxane in the embodiment of the invention 3.
Embodiment
Come the present invention is made an explanation below in conjunction with example.
Embodiment 1
At 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 the reactor, (ratio in Pt contained in the catalyzer and Ru quality and three kinds of raw material total masses is respectively 50mg/kg to add Platinic chloride and ruthenium chloride again, 50mg/kg), make solvent with Virahol, be under 130 ℃ of conditions in temperature, N
2Protection was reacted 7 hours down.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 that records its aqueous solution with the 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 on paraffin surface is 20 °.
Embodiment 2
At 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 the reactor, add Karst (Karstedt) platinum catalyst (counting 20mg/kg with Pt quality contained in the catalyzer and the ratio of three kinds of raw material total masses) again, make solvent with methyl alcohol, be under 240 ℃ of conditions in temperature, N
2Protection was reacted 16 hours down.Steaming desolventizes methyl alcohol and low boiling component, and the viscous liquid product that finally obtains the yellowish brown clarification is butynediol diethoxy ether polyethers comodified polysiloxane, and its viscosity is 279mPas.The surface tension that records its aqueous solution with the 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 on paraffin surface is 5 °.
Embodiment 3
At 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 the reactor, (ratio in Pt contained in the catalyzer and Ru quality and three kinds of raw material total masses is respectively 80mg/Kg to add Platinic chloride and ruthenium chloride solution again, 80mg/Kg) be catalyzer, make solvent with Virahol, be under 170 ℃ of conditions in temperature, N
2Protection was reacted 13 hours down.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product that finally obtains orange-yellow clarification is butynediol list propoxy-ether polyethers comodified polysiloxane, and its viscosity is 367mPas.Utilize hydrogen nuclear magnetic resonance spectrometer and infrared spectrometer that product is carried out structural characterization and (see accompanying drawing 1,2), by resolving position and the size at the peak in hydrogen nuclear magnetic resonance spectrogram and the infrared spectrum, show that the product that is synthesized is target product butynediol list propoxy-ether polyethers comodified polysiloxane.The surface tension that records its aqueous solution with the K-12 surface tension instrument is 23mN/m.Micelle-forming concentration is 487mg/L.Simultaneously its aqueous solution is 45 ° at the minimal contact angle of ptfe surface, is 35 ° at the minimal contact angle of paraffin.
Embodiment 4
At first the acetyl blocked allyl polyether of 22.65Kg; 6.81Kg butynediol dipropoxy ether and 10.63Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 1.57%) join in the reactor; add Karstedt platinum catalyst (ratio in Pt quality contained in the catalyzer and three kinds of raw material total masses is respectively 150mg/kg) again; make solvent with ethanol; be under 150 ℃ of conditions in temperature, N
2Protection was reacted 6 hours down.Steaming desolventizes ethanol and low boiling component, and the viscous liquid product that finally obtains amber clarification is butynediol dipropoxy ether polyethers comodified polysiloxane, and its viscosity is 794mPas.The surface tension that records its aqueous solution with the 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 on paraffin surface is 10 °.
Embodiment 5
At 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 the reactor, add chloroplatinic acid catalyst (ratio in Pt quality contained in the catalyzer and three kinds of raw material total masses is respectively 5mg/kg) again, make solvent with Virahol, be under 40 ℃ of conditions in temperature, N
2Protection was reacted 48 hours down.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product that finally obtains faint yellow clear is butynediol dipropoxy ether polyethers comodified polysiloxane, and its viscosity is 163mPas.The surface tension that records its aqueous solution with the 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 on paraffin surface is 5 °.
Embodiment 6
At first the acetyl blocked allyl polyether of 15.84g, 10.61Kg butynediol propoxy-ether and 23.75Kg containing hydrogen silicone oil (massfraction of reactive hydrogen is 0.57%) are joined in the reactor; add chloroplatinic acid catalyst (ratio in Pt quality contained in the catalyzer and three kinds of raw material total masses is respectively 300mg/Kg) again; make solvent with Virahol; be under 160 ℃ of conditions in temperature, N
2Protection was reacted 4 hours down.Steaming desolventizes Virahol and low boiling component, and the viscous liquid product that finally obtains yellow clear is butynediol propoxy-ether polyethers comodified polysiloxane, and its viscosity is 683mPas.The surface tension that records its aqueous solution with the 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 on paraffin surface is 25 °.
Embodiment 7
At first 10.82Kg methyl blocking allyl polyether, 15.64Kg butynediol propoxy-ether and 23.24Kg prestox tetrasiloxane are joined in the reactor, add Karstedt platinum catalyst (with Pt quality contained in the catalyzer and the ratio of the three kinds of raw material total masses other 50mg/Kg that scores) again, make solvent with epoxy six rings, be under 180 ℃ of conditions in temperature, N
2Protection was reacted 1 hour down.Steam except epoxy six rings and make solvent and low boiling component, the viscous liquid product that finally obtains yellow clear is alkyne diol propoxy-ether polyethers modification tetrasiloxane altogether, and its viscosity is 40mPas.The surface tension that records its aqueous solution with the 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 on paraffin surface is 10 °.
The synthetic target compound of 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 the infrared spectrum, shows that the product that is synthesized is target product.Now proton nmr spectra and the infrared spectra collection of illustrative plates with product among the embodiment 3 is that example describes.
Claims (14)
1. an alkyne diol b-oxide polyethers or 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:
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 are that viscosity is 40-800 mPas 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 on 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:
The polysiloxane that is contained the polyethers of unsaturated double-bond and contained reactive hydrogen by alkyne diol b-oxide or alkyne diol b-oxide, end is raw material, under solvent and catalyzer condition, in 40-300 ℃ of reaction 0.5-48 hour; Wherein alkyne diol b-oxide or alkyne diol propoxide, the end mol ratio that contains the polyethers of unsaturated double-bond and contain the polysiloxane of reactive hydrogen is 0.1-20: 0.1-20: 1, after reaction finishes, 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 ℃.
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, it is characterized in that described in alkyne diol b-oxide or alkyne diol propoxide, the end mole proportioning that contains the polyethers of unsaturated double-bond and contain the polysiloxane of reactive hydrogen be 0.1-10: 0.1-10: 1.
6. as the preparation method of each described a kind of alkyne diol b-oxide polyethers of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that the described molecular structural formula that contains the polysiloxane of reactive hydrogen is:
。
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 that contains reactive hydrogen is prestox tetrasiloxane or containing hydrogen silicone oil.
8. as the preparation method of each described a kind of alkyne diol b-oxide polyethers of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that the molecular structural formula that described end contains the polyethers of unsaturated double-bond is:
9. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 8 or alkyne diol propoxide polyethers comodified polysiloxane is characterized in that the polyethers that described end contains unsaturated double-bond is allyl polyether, methyl blocking allyl polyether or acetyl blocked allyl polyether.
10. as the preparation method of each described a kind of alkyne diol b-oxide polyethers of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that the molecular structural formula of described alkyne diol b-oxide or alkyne diol propoxide is:
11. the preparation method of a kind of alkyne diol b-oxide polyethers as claimed in claim 10 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that described alkyne diol ethoxylate comprises butynediol monosubstituted ethoxy ether or butynediol diethoxy ether, the alkyne diol propoxide comprises butynediol list propoxy-or butynediol dipropoxy ether.
12. aforesaid solvent is Virahol, ethanol, methyl alcohol, dioxane or toluene etc.
13. as the preparation method of each described a kind of alkyne diol b-oxide polyethers of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that described catalyzer is one or more in Platinic chloride, ruthenium chloride, the Karst platinum catalyst.
14. the preparation method as each described a kind of alkyne diol b-oxide polyethers of claim 3-5 or alkyne diol propoxide polyethers comodified polysiloxane, it is characterized in that described catalyst consumption, or/and Ru, its consumption is three kinds of raw material gross weight: catalyzer=1Kg: 5-300mg in Pt contained in the catalyzer.
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