CN109503824A - A kind of alkyl glycosides polyethers and its synthetic method - Google Patents

A kind of alkyl glycosides polyethers and its synthetic method Download PDF

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Publication number
CN109503824A
CN109503824A CN201811375723.4A CN201811375723A CN109503824A CN 109503824 A CN109503824 A CN 109503824A CN 201811375723 A CN201811375723 A CN 201811375723A CN 109503824 A CN109503824 A CN 109503824A
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polyethers
alkyl glycosides
synthetic method
alkyl
fatty alcohol
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房连顺
于子洲
董晓红
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Huaian Morning To New Materials Co Ltd
YANGZHOU CHENHUA NEW MATERIALS Co Ltd
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Huaian Morning To New Materials Co Ltd
YANGZHOU CHENHUA NEW MATERIALS Co Ltd
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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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

A kind of alkyl glycosides polyethers and its synthetic method, belong to organic compound synthesis technical field.It is first that fatty alcohol, glucose and acid catalyst mix progress acetalation by carbochain number, obtain transparent reaction liquid, with the pH value of potassium hydroxide adjusting transparent reaction liquid to 6~7, dual evaporation is carried out using thin film evaporator in distillation still again and sloughs excessive fatty alcohol, obtains alkyl glycoside coarse product；Then alkyl glycoside coarse product and catalyst are mixed and carries out dehydration, ethylene oxide is then passed to be reacted again to terminating, through aging, cooling, regulation system pH value to 6.5~7.0, obtain good good water solubility, stability in hard water, lower surface tension, the high alkyl glycosides polyethers of foaming power in hard water.

Description

A kind of alkyl glycosides polyethers and its synthetic method
Technical field
The present invention relates to the synthetic methods of alkyl glycosides polyethers, belong to organic compound synthesis technical field.
Background technique
Alkyl glycosides is a kind of surfactant haveing excellent performance, and has high surface activity, foaming abundancy, exquisiteness and steady Calmly, the features such as detergency is excellent, compatibility is splendid, biodegradability is good, non-stimulated to skin, good with human compatibility. It is widely used in the various fields such as washing Industry, cosmetic industry, food processing industry and pesticide.But Long carbon chain alkyl glycosides is also deposited The defects of water-soluble undesirable, the fatty alcohol polyoxyethylene ether of low EO adduct number is mostly used to carry out instead of fatty alcohol greatly at present It is glycosylation to prepare alcohol ether glucoside product, its water solubility can be improved while keeping the excellent performance of alkyl glycosides.
Dalian University of Technology is reported on " daily chemical industry " (synthesis of polyethylene glycol glycosides and moisturizing Journal of Sex Research) Yang Jinzong, Zhang Shufen professor are dehydrated with glucose, polyethylene glycol (PEG200,400,600) for raw material in acid condition to be obtained Polyethylene glycol glycosides.CN1651129 obtains alcohol ether glucoside using fatty alcohol polyoxyethylene ether and glucose acetalation Surfactant.CN105669786 carries out continuous reaction using fatty alcohol polyoxyethylene ether and glucose, steams using three-level Hair carries out dealcoholation treatment and obtains alcohol ether glucoside.
But above method all exist fatty alcohol polyoxyethylene ether due to boiling point it is more high-leveled and difficult to remove the shortcomings that, need using molten The method of agent extraction, the method for molecular distillation or other purification & isolations carries out, so the fatty alcohol polyoxyethylene ether generally used In ethylene oxide chain link it is smaller (only 3mol or so), since the molal quantity of ethylene oxide is less, make the water of alcohol ether glucoside The disadvantages of dissolubility, poor stability in hard water and foaming power.
Summary of the invention
In view of the above-mentioned problems in the prior art, it is an object of the present invention to provide a kind of good water solubility, stability in hard water is good, lower table Face tension and in hard water the high polyepoxyethane chain link of foaming power alkyl glycosides polyethers.
Alkyl glycosides polyethers of the present invention has a structure that
Wherein a+b+c+d=4~80, R C8~20H17~41。
It is tested, the good water solubility of alkyl glycosides polyethers, stability in hard water with the above structural formula be good, lower surface Power and the high feature of foaming power in hard water.
It is another object of the present invention to propose the preparation method of the above alkyl glycosides polyethers.
The present invention the following steps are included:
1) fatty alcohol, glucose and acid catalyst that carbochain number is C8~C20 are mixed, in 110~120 DEG C, 0.09MPa vacuum Degree is lower to carry out acetalation, obtains transparent reaction liquid, with the pH value of potassium hydroxide adjusting transparent reaction liquid to 6~7, then is steaming Evaporate in kettle using thin film evaporator carry out dual evaporation slough excessive fatty alcohol, obtain fatty alcohol residual quantity≤1%(wt) alkane Base glucosides crude product.
The reaction equation of step 1) is as follows:
2) in reaction kettle, alkyl glycoside coarse product and catalyst is mixed, 130 DEG C is warming up in the absence of oxygen and is taken off Water reaction, then passes to ethylene oxide, reacts under the conditions of the temperature of reaction system is 130~180 DEG C to terminating, then through old Change, be cooled to 80 DEG C, finally with the pH value of acid acceptor regulation system to 6.5~7.0, obtains alkyl glycosides polyethers.
The reaction equation of step 2 is as follows:
In step 1), the fatty alcohol and glucose of Long carbon chain carries out acetalation synthesizing alkyl polyglycoside using direct method, and side is anti- The water for answering side removing to generate, avoid indirect method first carries out alcohol with the fatty alcohol of Long carbon chain again with low-carbon alcohols and glucose response Exchange the residual of low-carbon alcohols and low-carbon alkyl glucosides in the alkyl glycosides of synthesis.
The present invention uses the method synthesizing alkyl polyglycoside polyethers of alkyl glycosides and ethylene oxide polymerization, and the product of formation has Ethylene oxide chain link is more, lighter color, and good water solubility, biological hydrolysis performance are good, stability in hard water is good, lower surface tension (≤24 Nm-1 the high advantage of foaming power) and in hard water.The invention avoids carried out using fatty alcohol polyoxyethylene ether and glucose Acetalation, excessive fatty alcohol polyoxyethylene ether are difficult to remove, need using more highly difficult purification & isolation method or The shortcomings that high to purification & isolation equipment requirement.
Further, carbochain number of the present invention is the quality that feeds intake of the fatty alcohol of C8~C20, glucose and acid catalyst Than being 100: 16~38: 0.1~0.5.The dissolution for being largely excessively beneficial to glucose and acidic catalyst using fatty alcohol is made admittedly Liquid-solid reaction changes to liquid reactive liquid solution, is conducive to the progress of acetalation, the especially reaction of the fatty alcohol of Long carbon chain more It can preferably carry out.
In step 2, oxygen free condition is: being first passed through N2After displacing air, then vacuumize.Due to ethylene oxide and air Contact can explode, therefore the ring-opening reaction of ethylene oxide needs to carry out under anaerobic, improves the safety of system.
In step 2, the temperature of reaction system is 160~180 DEG C.Since Long carbon chain alkyl glycosides fusing point is higher, heating is molten Viscosity is larger after change, slower with the reaction speed of ethylene oxide, needs induction slowly that could react, and in higher temperature Under, the viscosity of alkyl glycosides can reduce, and be conducive to carry out with the polymerization reaction of ethylene oxide, shorten the induction period of reaction, shorten The time of reaction.
In step 2, the catalyst is KOH, NaOH, CH3ONa or CH3OK.Use caustic alkali for the open loop of ethylene oxide Catalyst has the advantages that the advantages of narrow molecular weight distribution and polymerizable molecular amount are big.
In step 2, the quality that feeds intake of the catalyst accounts for 1~the 8 ‰ of alkyl glycosides polyether quality.The catalyst amount It can guarantee going on smoothly for epoxyethane ring-expansion polymerization；If amount is too many, the acid amount for needing to neutralize also increases, to neutralize The amount of the salt of generation also will increase, and salt content in product can be made to increase, be unfavorable for the application in downstream, to need to increase at purification The process of reason.
In step 2, the acid acceptor is citric acid, acetic acid, phosphoric acid, oxalic acid or sulfuric acid.
In step 2, ageing time >=1 h.Continue insulation reaction under conditions of keeping reaction temperature.Because of reaction kettle In have ethylene oxide segment and do not react completely, and the epoxy second that part is not reacted completely can be dissolved in reaction kettle liquid material Alkane；So improving safety in order to ensure ethylene oxide can react completely.
Specific embodiment
Below by way of specific embodiment, the invention will be further described, surface tension (σ) measurement in case study on implementation: Hang piece method, 25 DEG C of test temperature；Color is Pt-Co color number.
Embodiment 1
1, to 576 kg fatty alcohols (C8~10) of investment and 198kg glucose, 0.6kg acid catalysis the synthesis of alkyl glycosides: is added Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation, after reaction 8~10 hours, acquirement is transparent Transparent reaction liquid is moved into distillation still to 6~7 by reaction solution, then the pH value for adjusting transparent reaction liquid with potassium hydroxide.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs excessive fatty alcohol, and obtaining the degree of polymerization is 1.4 The alcohol of C8~10 residual quantity 0.82% alkyl glycoside coarse product.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 380kg is put into reaction kettle, and 4.4kg is added Catalyst KOH, is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.Then it is passed through 176kg ethylene oxide again at 130 DEG C Under the conditions of reacted, after ethylene oxide adds, continue to be cooled to 80 DEG C in 130 DEG C of 1 h of aging, citric acid tune pH value be added 6.5~7.0, alkyl glycosides polyethers APG0810EO is obtained4。
Gained alkyl glycosides polyether product APG0810EO4Surface tension be 22.1 Nm-1, color 15.5#(Pt- Co).The above alkyl glycosides polyethers APG0810EO4Structural formula are as follows:
A+b+c+d=4 in formula, R C8~10H17~41。
Embodiment 2
1, to investment 800kg fatty alcohol (C12~14) and 198kg glucose, 1.6kg acid catalysis the synthesis of alkyl glycosides: is added Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, after reaction solution is transparent Potassium hydroxide is added and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs excessive fatty alcohol (C12~14), is gathered The alkyl glycoside coarse product of the right alcohol of the C12 for being 1.6~14 residual quantity 0.69%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 467kg is put into reaction kettle, and 5.4kg is added Catalyst n aOH, is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.440kg ethylene oxide is passed through to react at 150 DEG C, After ethylene oxide adds, continue to be cooled to 80 DEG C in 160 DEG C of 1 h of aging, oxalic acid tune pH value is added 6.5~7.0, alkane is made Base glucosides polyethers APG1214EO10。
Gained alkyl glycosides polyether product APG1214EO10Surface tension be 21.9 Nm-1, color 12.8#(Pt- Co).The above alkyl glycosides polyethers APG1214EO10Structural formula are as follows:
A+b+c+d=10 in formula, R C12~14H25~29。
Embodiment 3
1, to investment 1024kg fatty alcohol (C16~18) and 198 kg glucose, 3kg acid catalysis the synthesis of alkyl glycosides: is added Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, after reaction solution is transparent Potassium hydroxide is added and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs the alcohol of excessive C16~18, and obtaining the degree of polymerization is The alkyl glycoside coarse product of the alcohol of 1.5 C16~18 residual quantity 0.91%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 506kg is put into reaction kettle, and 4.2kg is added Catalyst CH3ONa is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.880kg ethylene oxide is passed through to react at 160 DEG C, After ethylene oxide adds, continue to be cooled to 80 DEG C in 160 DEG C of 1 h of aging, acetic acid tune pH value is added 6.5~7.0, alkane is made Base glucosides polyethers APG1618EO20。
Gained alkyl glycosides polyether product APG1618EO20Surface tension be 23.6 Nm-1, color 9.5#(Pt-Co). The above alkyl glycosides polyethers APG1618EO20Structural formula are as follows:
A+b+c+d=20 in formula, R C16~18H33~37。
Embodiment 4
1, the synthesis of alkyl glycosides: to investment 1128kg fatty alcohol (C18~20) and 198kg glucose, 4.5 kg acid is added and urge Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, reaction solution is transparent Potassium hydroxide is added afterwards and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs the alcohol of excessive C18~20, and obtaining the degree of polymerization is The alkyl glycoside coarse product of the alcohol of 1.4 C18~20 residual quantity 0.87%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 520kg is put into reaction kettle, and 4kg is added and urges Agent CH3OK is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.It is passed through 3520kg ethylene oxide to react at 180 DEG C, ring After oxidative ethane adds, continue to be cooled to 80 DEG C in 180 DEG C of 1 h of aging, phosphoric acid tune pH value is added 6.5~7.0, alkyl is made Glucosides polyethers APG1820EO80。
Gained alkyl glycosides polyether product APG1820EO80Surface tension be 23.9 Nm-1, color 4.8#(Pt-Co). The structural formula of the above alkyl glycosides polyethers APG1820EO80 are as follows:
A+b+c+d=80 in formula, R C18~20H37~41。
Embodiment 5
1, to 912 kg fatty alcohols (C14~16) of investment and 198kg glucose, 4.5kg acid catalysis the synthesis of alkyl glycosides: is added Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, after reaction solution is transparent Potassium hydroxide is added and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs the alcohol of excessive C14~16, and obtaining the degree of polymerization is The alkyl glycoside coarse product of the alcohol of 1.6 C14~16 residual quantity 0.65%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 497kg is put into reaction kettle, and 6.3kg is added Catalyst CH3ONa is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.It is anti-at 170 DEG C to be passed through 2640kg ethylene oxide It answers, after ethylene oxide adds, continues to be cooled to 80 DEG C in 170 DEG C of 1 h of aging, sulfuric acid tune pH value is added 6.5~7.0, makes Obtain alkyl glycosides polyethers APG1416EO60。
Gained alkyl glycosides polyether product APG1416EO60Surface tension be 22.5 Nm-1, color 6.7#(Pt-Co). The above alkyl glycosides polyethers APG1416EO60Structural formula are as follows:
A+b+c+d=60 in formula, R C14~16H29~33。
Embodiment 6
1, to investment 520 kg octanols (C8 fatty alcohol) and 198kg glucose, 0.8kg acid catalysis the synthesis of alkyl glycosides: is added Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, after reaction solution is transparent Potassium hydroxide is added and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs excessive C8 alcohol, and obtaining the degree of polymerization is 1.6 The alkyl glycoside coarse product of C8 alcohol residual quantity 0.23%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 399kg is put into reaction kettle, and 3kg is added and urges Agent NaOH, is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.It is passed through 352kg ethylene oxide to react at 160 DEG C, ring After oxidative ethane adds, continue to be cooled to 80 DEG C in 160 DEG C of 1 h of aging, phosphoric acid tune pH value is added 6.5~7.0, alkyl is made Glucosides polyethers APG08EO8。
Gained alkyl glycosides polyether product APG08EO8Surface tension be 21.4 Nm-1, color 14.8#(Pt-Co). The above alkyl glycosides polyethers APG08EO8Structural formula are as follows:
A+b+c+d=8 in formula, R C8H17。
Embodiment 7
1, the synthesis of alkyl glycosides: to investment 744kg laruyl alcohol (C12 fatty alcohol) and 198 kg glucose, 1.5kg acid is added and urges Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, reaction solution is transparent Potassium hydroxide is added afterwards and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs excessive C12 alcohol, and obtaining the degree of polymerization is 1.4 The alkyl glycoside coarse product of C12 alcohol residual quantity 0.45%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 421kg is put into reaction kettle, and 5.4kg is added Catalyst CH3OK is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.660kg ethylene oxide is passed through to react at 160 DEG C, After ethylene oxide adds, continue to be cooled to 80 DEG C in 160 DEG C of 1 h of aging, oxalic acid tune pH value is added 6.5~7.0, alkane is made Base glucosides polyethers APG12EO15。
Gained alkyl glycosides polyether product APG12EO15Surface tension be 21.8 Nm-1, color 12.3#(Pt-Co). The above alkyl glycosides polyethers APG12EO15Structural formula are as follows:
A+b+c+d=15 in formula, R C12H25。
Embodiment 8
1, the synthesis of alkyl glycosides: to investment 1192kg palmityl alcohol (C20 fatty alcohol) and 198kg glucose, 5.4kg acid is added and urges Agent is warming up to 110~120 DEG C, and vacuum is transferred to 0.09MPa and carries out acetalation reaction 8~10 hours, reaction solution is transparent Potassium hydroxide is added afterwards and adjusts pH value to 6~7, reaction solution is moved into distillation still.
Dual evaporation is carried out using thin film evaporator in distillation still and sloughs excessive C20 alcohol, and obtaining the degree of polymerization is 1.5 The alkyl glycoside coarse product of C20 alcohol residual quantity 0.62%.
2, the synthesis of alkyl glycosides polyethers: abovementioned alkyl glucosides crude product 550kg is put into reaction kettle, and 2.8kg is added Catalyst KOH, is passed through N2Displacement, vacuumizes, is warming up to 130 DEG C of dehydration 1h.1320kg ethylene oxide is passed through to react at 170 DEG C, After ethylene oxide adds, continue to be cooled to 80 DEG C in 170 DEG C of 1 h of aging, acetic acid tune pH value is added 6.5~7.0, alkane is made Base glucosides polyethers APG20EO30。
Gained alkyl glycosides polyether product APG20EO30Surface tension be 22.3 Nm-1, color 7.9#(Pt-Co).With Upper alkyl glycosides polyethers APG20EO30Structural formula are as follows:
A+b+c+d=30 in formula, R C20H41。

Claims (9)

1. a kind of alkyl glycosides polyethers, has a structure that
Wherein a+b+c+d=4~80, R C8~20H17~41。
2. the synthetic method of alkyl glycosides polyethers as described in claim 1, it is characterised in that the following steps are included:
1) fatty alcohol, glucose and acid catalyst that carbochain number is C8~C20 are mixed, in 110~120 DEG C, 0.09MPa vacuum Degree is lower to carry out acetalation, obtains transparent reaction liquid, with the pH value of potassium hydroxide adjusting transparent reaction liquid to 6~7, then is steaming Evaporate in kettle using thin film evaporator carry out dual evaporation slough excessive fatty alcohol, obtain fatty alcohol residual quantity≤1%(wt) alkane Base glucosides crude product；
2) in reaction kettle, alkyl glycoside coarse product and catalyst is mixed, 130 DEG C is warming up in the absence of oxygen and is taken off Water reaction, then passes to ethylene oxide, reacts under the conditions of the temperature of reaction system is 130~180 DEG C to terminating, then through old Change, be cooled to 80 DEG C, finally with the pH value of acid acceptor regulation system to 6.5~7.0, obtains alkyl glycosides polyethers.
3. the synthetic method of alkyl glycosides polyethers according to claim 2, it is characterised in that the carbochain number is C8~C20's The mass ratio that feeds intake of fatty alcohol, glucose and acid catalyst is 100: 16~38: 0.1~0.5.
4. the synthetic method of alkyl glycosides polyethers according to claim 2, it is characterised in that in step 2, oxygen free condition is: First it is passed through N2After displacing air, then vacuumize.
5. the synthetic method of alkyl glycosides polyethers according to claim 2, it is characterised in that in step 2, the temperature of reaction system Degree is 160~180 DEG C.
6. the synthetic method of alkyl glycosides polyethers according to claim 2, it is characterised in that in step 2, the catalyst is KOH、NaOH、CH3ONa or CH3OK。
7. the synthetic method of alkyl glycosides polyethers according to claim 6, it is characterised in that in step 2, the catalyst The quality that feeds intake accounts for 1~the 8 ‰ of alkyl glycosides polyether quality.
8. according to Claims 2 or 3 or the synthetic method of the 4 or 5 or 6 or 7 alkyl glycosides polyethers, it is characterised in that step 2 In, the acid acceptor is citric acid, acetic acid, phosphoric acid, oxalic acid or sulfuric acid.
9. according to Claims 2 or 3 or the synthetic method of the 4 or 5 or 6 or 7 alkyl glycosides polyethers, it is characterised in that step 2 In, ageing time >=1 h.
CN201811375723.4A 2018-11-19 2018-11-19 A kind of alkyl glycosides polyethers and its synthetic method Pending CN109503824A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0543403A (en) * 1991-08-08 1993-02-23 Kao Corp Agent for promoting activity of biocide and agricultural chemical composition
CN101333233A (en) * 2007-06-25 2008-12-31 上海发凯化工有限公司 Auto discharging system for preparing light-coloured transparent alkyl glycoside
CN104140525A (en) * 2013-10-29 2014-11-12 中国石油化工股份有限公司 Preparation method of alkyl glucoside polyether for drilling fluid
CN105418699A (en) * 2015-12-29 2016-03-23 河北合佳医药科技集团有限公司 Method and production device for continuously producing alkyl glucoside

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0543403A (en) * 1991-08-08 1993-02-23 Kao Corp Agent for promoting activity of biocide and agricultural chemical composition
CN101333233A (en) * 2007-06-25 2008-12-31 上海发凯化工有限公司 Auto discharging system for preparing light-coloured transparent alkyl glycoside
CN104140525A (en) * 2013-10-29 2014-11-12 中国石油化工股份有限公司 Preparation method of alkyl glucoside polyether for drilling fluid
CN105418699A (en) * 2015-12-29 2016-03-23 河北合佳医药科技集团有限公司 Method and production device for continuously producing alkyl glucoside

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