CN101186702B - Polyethene polyhydric alcohol organic silicon water soluble polymer and preparation method thereof - Google Patents
Polyethene polyhydric alcohol organic silicon water soluble polymer and preparation method thereof Download PDFInfo
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Abstract
Provided is a polyethylene polyalcohol organosilicon water-soluble polymer and a process for preparation, belonging to the preparing field of macromolecule. The preparation process of the polymer comprises (1) charging organopolysiloxane or organosilane and organic solution which contains halogen atoms or hydrogen activating group in a high-pressure autoclave, and charging polyol compounds in same the mol as the halogen atoms or hydrogen in the high-pressure autoclave at the temperature of -80-150DEG C and the pressure of atmosphere pressure to 1.0 MPa to rapidly mix for 2-20h, (2) adding epoxyethane or epoxypropane or compounds of the epoxyethane and the epoxypropane, wherein the mol ratio between the epoxyethane or epoxypropane and hydroxyl group is 1-30000 and the mol ratio between the epoxyethane and epoxypropane is 1-30, and charging alkali hydroxides or alkali alcoholate which is 0.3-1.5% of raw mass as catalyst, after the reaction at the temperature of 100-200DEG C and the pressure of 0.2-0.7MPa reacting for 1.5-6 hours, and obtaining the polymer of the invention. The polymer is the same with crude oil demulsifying agent, the squeeze ratio of the polymeric compounds can achieve 95% and the method for synthesizing is comparatively easy.
Description
Technical field:
The invention belongs to the polymer preparation field, particularly a kind of have single armed, both arms or multi-arm polyethene polyhydric alcohol organic silicon water soluble polymer and preparation method thereof.
Background technology:
It is hundreds of low-molecular weight compounds that tensio-active agent commonly used mostly is molecular weight.Further investigation along with numerous areas, as intensified oil reduction, pharmaceutical carrier and sustained release, biosimulation, polymkeric substance LB film, medical macromolecular materials (anticoagulation), letex polymerization etc., requirement to tensio-active agent becomes more diverse and high performance, and having surface-active macromolecular compound has become the focus that people pay close attention to.Usually with molecular weight more than thousands of and have surface-active material and be called polymeric surface active agent.The polymeric surface active agent of Shi Yonging has Mierocrystalline cellulose and derivative thereof the earliest, and the natural seaweed acid sodium and the various starch that use as colloid protective agent.Compare with low-molecular-weight surfactant, polymeric surface active agent has following characteristics: (1) has higher molecular weight, and penetrating power is poor, can form unimolecular micelle or polymolecular micella; (2) soltion viscosity height, good film-forming property; (3) have performances such as good dispersion, emulsification, thickening, stable and flocculation, whipability is poor, often makes defoamer; (4) most of polymeric surface active agents are low toxicities or nontoxic, have environment friendly; (5) ability that reduces surface tension and interfacial tension a little less than, and surfactivity sharply descends with the rising of molecular weight, it reduces capillary ability and significantly strengthens when introducing fluoroalkyl or silylation on the hydrophobic group.Chinese patent CN 02115154.7 obtains a kind of efficient composite hydrate anticoagulant by nonionogenic tenside polyol esters of fatty acids and the mixing of polyoxyethylene alcohol fatty acid ester.Chinese patent CN 02123728.X obtains a kind of crude oil flowability improver by multiple nonionogenic tenside and fatty alcohol-polyoxyethylene ether sulfuric acid ester sodium salt, fatty alcohol sulphuric acid fat sodium salt are composite.Chinese patent CN 02133373.4 utilizes the reaction of isocyanate groups and active hydrogen compounds to synthesize a kind of double quaternary ammonium salt base mono-phemyol surface active agent.Chinese patent CN 02733373.6 utilizes the reaction of isocyanate groups and active hydrogen compounds to synthesize a kind of diquaternary-base diphenyl surface reactive agent.Chinese patent CN 02144674.1 has obtained a kind of fine surface-active carboxylate surface active agent ternary injection liquid that has by changing collocation method.Emulsion splitter among the Chinese patent CN 1600835A has the trimethyl-glycine molecular structure, belong to zwitterionics, this crude oil demulsifier is initiator with the organic amine, with propylene oxide, ethylene oxide polymerization generates polyethers, generate the betaine type molecular structure with the halogenated carboxylic acid reaction again, this emulsion splitter has been carried out twice dehydrating of crude oil experiment, dehydration rate reaches 89% and 92% respectively.
Summary of the invention:
The object of the present invention is to provide a kind of polyethene polyhydric alcohol organic silicon water soluble polymer and preparation method thereof, this water-soluble polymers has dehydration rate preferably as emulsion splitter, and the preparation method of this water-soluble polymers is easier to.
A kind of polyethene polyhydric alcohol organic silicon water soluble polymer of the present invention has single armed, both arms or multi-arm structure, and its general structure is shown in (1)～(3):
Wherein, R, the R in general formula (1)～(3)
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl and derivative thereof, preferred C
1～C
12Alkyl, cycloalkyl or aryl and derivative thereof, x is 1～30000, and is preferred 20～3000, and y is 1～30000, preferred 20～3000, the concrete structure of this polymkeric substance is by the structures shape of the organopolysiloxane in the preparation process or organosilane and many alcohol compounds.
Prepare above-mentioned polyethene polyhydric alcohol organic silicon water soluble polymer method comprise following steps:
1) organopolysiloxane or the organosilane with halogen atom or hydrogen activity group adds autoclave, in organic solvent, under-80 ℃～150 ℃ conditions, the equimolar multicomponent alcoholics compound of adding and halogen atom or hydrogen, under normal pressure～1.0MPa, stir fast, react and obtained the hydroxyl organopolysiloxane of end group in 2～20 hours; The preferred normal hexane of organic solvent, tetrahydrofuran (THF), toluene and ether, preferred-10 ℃～120 ℃ of temperature of reaction, the preferred normal pressure～0.5MPa of reaction pressure, preferred 6～12 hours of reaction times;
The general structure of the organopolysiloxane of above-mentioned halogen atom or hydrogen activity group is shown in (I)～(V):
The preferred halogen atom in two ends or the hydrogen activity group of general structure (I)～(V), R
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl and derivative thereof, R
1Preferable methyl, ethyl, propyl group, butyl, sec.-propyl or cyclohexyl, most preferable, ethyl, propyl group, butyl or phenyl, R
2Preferred C
1～C
12Alkyl, cycloalkyl or aryl and derivative thereof, n is 1～30, and is preferred 1～10, most preferably 1～5, X represents halogen, preferred Cl, Br or F;
The general structure of above-mentioned organosilane is shown in (VI)～(VIII):
RSiX
3(VI) RR1SiX
2(VII) RR
1R
2SiX(VIII)
In general structure (VI)～(VIII), R, R
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl and derivative thereof, R, R
1And R
2Can get identical or different substituting group, R preferable methyl, ethyl, propyl group, butyl, sec.-propyl or cyclohexyl, most preferable, ethyl, propyl group, butyl or phenyl, R
2Preferred C
1～C
12Alkyl, cycloalkyl or aryl and derivative thereof, X is a halogen, preferred Cl, Br or F;
The general structure of above-mentioned multicomponent alcoholics compound is shown in (IX)～(XI):
In the general structure (IX)～(XI), R
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl and derivative thereof, R
1And R
2Can get identical or different substituting group, R
1And R
2Preferred C
1～C
12Alkyl, cycloalkyl or aryl and derivative thereof, many alcohol compounds hydroxyl number 2～30, preferred 2～10, most preferably 2～5;
2) adding with the hydroxyl mol ratio is 1～30000 oxyethane again, the mixture of propylene oxide or oxyethane and propylene oxide, the oxyethane in the mixture and the mol ratio of propylene oxide are 1-30, preferred 1-5, add alkali-metal oxyhydroxide again or its alkoxide is made catalyzer, catalyst levels is raw material total mass 0.3-1.5%, temperature is 100～200 ℃, pressure is 0.2～0.7MPa, reacted 1.5 to 6 hours, promptly obtain single armed, the polyethene polyhydric alcohol organic silicon water soluble polymer of both arms or multi-arm, this polymkeric substance comprises polyoxyethylene, the homopolymer of polyoxy propane or their multipolymer, number-average molecular weight is 2000～500000, preferred 3000～200000.
Beneficial effect of the present invention is, have structures such as polyoxyethylene (or polyoxypropylene), organic silica and multi-arm in the molecular chain of this water-soluble polymers simultaneously, combine their excellent properties, have good surfactivity and heatproof characteristic, be specially adapted to do crude oil demulsifier, pesticide dispersing agent and daily necessities additive, dehydration rate can reach 95%, and synthetic method is easier to.
Embodiment:
Embodiment is the specific examples that adopts for detailed description the present invention, but is not limited to following embodiment when practical application.
Embodiment 1
The organopolysiloxane pentamer 0.6825g that will have general structure (I) adds autoclave, make solvent with hexane, the ice-water bath cooling adds ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The oxyethane and the 17.4g propylene oxide that add 13.2g again, 110 ℃, 0.3MPa reacted 2 hours, promptly obtained tensio-active agent 28.43g, yield 90%.The number-average molecular weight of resulting polymers is 32500.
With above-mentioned tensio-active agent crude oil is carried out dehydration test, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 93.5%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 2
The organopolysiloxane pentamer 0.6825g that will have general structure (I) adds autoclave, make solvent with hexane, the ice-water bath cooling adds glycerol 0.46g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The oxyethane and the 34.8g propylene oxide that add 26.4g again, 120 ℃, 0.4MPa reacted 2.5 hours, promptly obtained tensio-active agent 56.73g, yield 91%.The number-average molecular weight of resulting polymers is 55600.
With above-mentioned tensio-active agent crude oil is dewatered, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 94%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 3
The organopolysiloxane pentamer 0.4725g that will have general structure (II) adds autoclave, make solvent with hexane, the ice-water bath cooling adds ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The oxyethane that adds 22g again, 130 ℃, 0.5MPa reacted 2.5 hours, promptly obtained tensio-active agent 21.19g, yield 93%.The number-average molecular weight of resulting polymers is 16600.
With above-mentioned tensio-active agent crude oil is dewatered, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 94.5%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 4
The organopolysiloxane pentamer 0.4725g that will have general structure (II) adds autoclave, make solvent with hexane, the ice-water bath cooling adds glycerol 0.46g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The propylene oxide that adds 29g again, 140 ℃, 0.6MPa reacted 3 hours, promptly obtained tensio-active agent 27.84g, yield 93%.The number-average molecular weight of resulting polymers is 25700.
With above-mentioned tensio-active agent crude oil is dewatered, the following above-mentioned tensio-active agent of 8mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 95%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 5
The organopolysiloxane pentamer 0.3g that will have general structure (V) adds autoclave, make solvent with hexane, the ice-water bath cooling adds ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; Add 33g oxyethane and 43.5g propylene oxide again, 110 ℃, 0.3MPa reacted 2 hours, promptly obtained tensio-active agent 70.56g, yield 91.5%.The number-average molecular weight of resulting polymers is 73800.
With above-mentioned tensio-active agent crude oil is carried out dehydration test, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 94.5%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 6
The organopolysiloxane pentamer 0.6825g that will have general structure (I) adds autoclave, make solvent with hexane, the ice-water bath cooling adds ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The oxyethane and the 87g propylene oxide that add 66g again, 110 ℃, 0.3MPa reacted 2 hours, promptly obtained tensio-active agent 140.9g, yield 91.5%.The number-average molecular weight of resulting polymers is 148400.
With above-mentioned tensio-active agent crude oil is carried out dehydration test, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 94%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 7
The organopolysiloxane pentamer 0.6825g that will have general structure (I) adds autoclave, make solvent with hexane, the ice-water bath cooling adds ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; The oxyethane and the 101.5g propylene oxide that add 77g again, 110 ℃, 0.3MPa reacted 2 hours, promptly obtained tensio-active agent 163.33g, yield 91%.The number-average molecular weight of resulting polymers is 164500.
With above-mentioned tensio-active agent crude oil is carried out dehydration test, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 94.5%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Embodiment 8
The trimethylchlorosilane 0.5425g that will have general structure (VIII) adds autoclave, makes solvent with hexane, the ice-water bath cooling, add ethylene glycol 0.31g, quick stirring reaction obtained the hydroxyl organopolysiloxane of end group, transformation efficiency 95% in 12 hours under the normal pressure; Add catalyzer strontium hydroxide 0.8g, sodium hydroxide 0.1g to above-mentioned product; Add 33g oxyethane and 43.5g propylene oxide again, 110 ℃, 0.3MPa reacted 2 hours, promptly obtained tensio-active agent 70.93g, yield 93.5%.The number-average molecular weight of resulting polymers is 73600.
With above-mentioned tensio-active agent crude oil is carried out dehydration test, the following above-mentioned tensio-active agent of 10mg that in 100ml crude oil, adds of concrete grammar, 60 ℃ of mixings, left standstill two hours, other gets 100ml heating crude oil to 60 ℃, leaves standstill and does blank in 2 two hours, the result shows, neat through the crude oil water-oil interface that tensio-active agent was handled, water colour is more clear, and the dehydration rate of tensio-active agent is 96.5%; And blank does not have water-oil interface, water colour muddiness, dehydration rate 6%.
Claims (6)
1. a polyethene polyhydric alcohol organic silicon water soluble polymer is characterized in that, preparation method's step of this polymkeric substance is as follows:
1) organopolysiloxane or the organosilane with halogen atom or hydrogen activity group adds autoclave, in organic solvent, under-80 ℃～150 ℃ conditions, the equimolar multicomponent alcoholics compound of adding and halogen atom or hydrogen, under normal pressure～1.0MPa, stir fast, react and obtained the hydroxyl organopolysiloxane of end group in 2～20 hours;
The organopolysiloxane of above-mentioned halogen atom or hydrogen activity group or organosilane general structure are as follows:
Wherein, R
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl, n is 1～30, X is a halogen;
RR
1R
2SiX(VIII)
Wherein, R, R
1With R2 be C
1～C
30Alkyl, cycloalkyl or aryl, R, R
1And R
2Can get identical or different substituting group, X is a halogen;
The general structure of above-mentioned multicomponent alcoholics compound is shown in (IX)～(X):
Wherein, R
1And R
2Be C
1～C
30Alkyl, cycloalkyl or aryl, R
1And R
2Can get identical or different substituting group;
2) add again with the hydroxyl mol ratio be 1～30000 oxyethane, propylene oxide or oxyethane and the mixture of propylene oxide, the oxyethane in the mixture and the mol ratio of propylene oxide are 1～30, add alkali-metal oxyhydroxide again or its alkoxide is made catalyzer, catalyst levels is a raw material total mass 0.3～1.5%, temperature of reaction is 100～200 ℃, reaction pressure is 0.2～0.7MPa, reaction times is 1.5 to 6 hours, promptly obtain polyethene polyhydric alcohol organic silicon water soluble polymer, number-average molecular weight is 3000～200000.
2. polyethene polyhydric alcohol organic silicon water soluble polymer according to claim 1 is characterized in that, in the step 1), organic solvent is normal hexane, tetrahydrofuran (THF), toluene or ether, temperature of reaction is-10 ℃～120 ℃, and reaction pressure is normal pressure～0.5MPa, and the reaction times is 6～12 hours.
3. polyethene polyhydric alcohol organic silicon water soluble polymer according to claim 1 is characterized in that, in step 1), and R in the general structure of the organopolysiloxane of halogen atom or hydrogen activity group
1Be methyl, ethyl, propyl group, butyl, phenyl, sec.-propyl or cyclohexyl, R
2Be C
1～C
12Alkyl, cycloalkyl or aryl, n is 1～10, X is Cl, Br or F.
4. polyethene polyhydric alcohol organic silicon water soluble polymer according to claim 2 is characterized in that, in the step 1), the R in the general structure of organosilane is methyl, ethyl, propyl group, butyl, phenyl, sec.-propyl or cyclohexyl, R
2Be C
1～C
12Alkyl, cycloalkyl or aryl, X is Cl, Br or F.
5. polyethene polyhydric alcohol organic silicon water soluble polymer according to claim 1 is characterized in that, in the step 1), and the R in the structure of multicomponent alcoholics compound
1And R
2Be C
1～C
12Alkyl, cycloalkyl or aryl.
6. polyethene polyhydric alcohol organic silicon water soluble polymer according to claim 1 is characterized in that step 2) in, the molar ratio of oxyethane and propylene oxide is 1-5 in oxyethane and the propylene oxide mixture.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004559A (en) * | 1986-07-04 | 1991-04-02 | Th. Goldschmidt Ag | Polyoxyalkylene-polysiloxane block copolymers as demulsifiers for water-containing oil |
| CN1107477A (en) * | 1993-06-24 | 1995-08-30 | 戈尔德施米特股份公司 | Silane with hydrophilic group, preparation and application of same |
| WO2001058986A1 (en) * | 2000-02-11 | 2001-08-16 | Dow Corning S.A. | Silicone polymer emulsions |
-
2007
- 2007-11-16 CN CN2007101774828A patent/CN101186702B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004559A (en) * | 1986-07-04 | 1991-04-02 | Th. Goldschmidt Ag | Polyoxyalkylene-polysiloxane block copolymers as demulsifiers for water-containing oil |
| CN1107477A (en) * | 1993-06-24 | 1995-08-30 | 戈尔德施米特股份公司 | Silane with hydrophilic group, preparation and application of same |
| WO2001058986A1 (en) * | 2000-02-11 | 2001-08-16 | Dow Corning S.A. | Silicone polymer emulsions |
Non-Patent Citations (2)
| Title |
|---|
| 龙斌.聚醚型有机硅表面活性剂的合成与应用.香料香精化妆品 2.2004,(2),31-35. |
| 龙斌.聚醚型有机硅表面活性剂的合成与应用.香料香精化妆品 2.2004,(2),31-35. * |
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