CN101381462A - Polysiloxane binary alcohol with polyether block and preparation method thereof - Google Patents

Polysiloxane binary alcohol with polyether block and preparation method thereof Download PDF

Info

Publication number
CN101381462A
CN101381462A CNA2008101965336A CN200810196533A CN101381462A CN 101381462 A CN101381462 A CN 101381462A CN A2008101965336 A CNA2008101965336 A CN A2008101965336A CN 200810196533 A CN200810196533 A CN 200810196533A CN 101381462 A CN101381462 A CN 101381462A
Authority
CN
China
Prior art keywords
polyether block
binary alcohol
preparation
polysiloxane
polysiloxane binary
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CNA2008101965336A
Other languages
Chinese (zh)
Other versions
CN101381462B (en
Inventor
张兴元
李维虎
戴家兵
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanzhou Scisky Technology Co ltd
Original Assignee
Hefei Scisky Chemical Industry Co ltd
University of Science and Technology of China USTC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hefei Scisky Chemical Industry Co ltd, University of Science and Technology of China USTC filed Critical Hefei Scisky Chemical Industry Co ltd
Priority to CN2008101965336A priority Critical patent/CN101381462B/en
Publication of CN101381462A publication Critical patent/CN101381462A/en
Application granted granted Critical
Publication of CN101381462B publication Critical patent/CN101381462B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Abstract

The invention discloses polyether block polysiloxane diol and a method for preparing the same. The method is characterized by comprising the following steps: performing ring-opening polymerization through cyclic siloxane and dihydro terminated disiloxane first to obtain dihydro terminated polysiloxane, and then performing hydrosilylation reaction with mono-vinyl terminated polyether oligomer to form the polyether block polysiloxane diol the structural formula of which is shown in the graph, wherein R1 and R2 are CH3 and CH2CH3 and/or CH2CH2CH3 respectively, R3 is H or CH3, n is an integer between 1 and 1, 000, and p and q are integers between 1 and 100. The polyether block polysiloxane diol prepared by the method has the advantages of better hydrolysis resistance and storage stability, and high reactivity; in addition, the polyether block polysiloxane diol improves the problem of the unsatisfactory mechanical property of the prior siloxane diol in modifying copolymers.

Description

Polysiloxane binary alcohol of a kind of polyether block and preparation method thereof
Technical field
The invention belongs to macromolecular material intermediate polysiloxane binary alcohol and preparation method thereof technical field, particularly polysiloxane binary alcohol of polyether oligomers block and preparation method thereof.
Background technology
Because there is terminal hydroxy group in polysiloxane binary alcohol, therefore often be used as multiple coating such as intermediate preparation urethane, polyester, superpolymer thermoplastic elastomer, foamed thermoplastic body etc.With polysiloxane binary alcohol as the material of intermediate preparation owing to have good water tolerance, resistance to deterioration and surface property and better biocompatibility etc., be used widely in a lot of fields.
Chinese patent CN90105777.0 has introduced a kind of lower molecular weight α that produces, the method for ω siloxane glycol, and secondary hydrolyzable alkoxy TMOS under an acidic catalyst effect makes the siloxanes two ends have hydroxy functional group.Since with the hydroxyl instability that siloxanes directly links to each other, the not too suitable intermediate of making materials such as preparation urethane, polyester.
Day disclosure special permission communique spy opens flat 5-97868 and has proposed the method that a kind of preparation one end contains the polysiloxane binary alcohol of two hydroxyls, is made by the polysiloxane addition reaction of silicon with hydrogen of the dibasic alcohol that contains vinyl and single si-h bond.Prepared silicone glycols needing solvent even mixed solvent often with the reaction of polar comonomer, therefore is unfavorable for save energy and environment protection because its polarity is lower.
U.S.'s " polymer science magazine " (Journal of Polymer Science, Part A:Polymer Chemistry, nineteen ninety-five, 1773 pages of 33 volumes) introduced and utilized α, the hydrolysis and obtain a kind of preparation method of polysiloxane binary alcohol of hydroxyl butyl end-capping under the acid catalyst effect of ω-dihydroxy butyl tetramethyl disiloxane and dimethoxy dimethylsilane.But thereby the end capped polysiloxane binary alcohol of this hydroxyalkyl makes polysiloxane binary alcohol hydroxyl meeting attack siloxane bond under comparatively high temps (as 70 ℃) of product stability reduction and hydroxyl butyl end-capping form shortcomings such as ring compound owing to easily generating end-vinyl after can't avoiding terminal hydroxy group to dewater, so the end capped polysiloxane binary alcohol of the type hydroxyalkyl has been subjected to more restriction as the intermediate preparation macromolecular material time.
Summary of the invention
The invention provides polysiloxane binary alcohol of a kind of polyether block and preparation method thereof, to overcome existing polysiloxane binary alcohol hydrolysis and package stability is poor, reactive behavior is low problem, the mechanical property when improving silicone-modified multipolymer simultaneously.
The preparation method of the polysiloxane binary alcohol of polyether block of the present invention is characterized in that: earlier with annular siloxane and two hydrogen end-blocking sily oxide in molar ratio 20～2:1 react 48～72h with the acid catalyst of press reactant total mass 0.5～2% at 40～60 ℃; Post reaction mixture through deionized water wash-out catalyzer, distill out unreacted completely behind the annular siloxane, obtain two hydrogen terminated polysiloxanes; Again two hydrogen terminated polysiloxanes and mono-vinyl terminated polyether oligopolymer are pressed every gram reactant 10～35 μ g platinum metal catalyst 70～80 ℃ of addings, at 80～120 ℃ of reaction 4～8h; Reaction product is removed catalyzer and unreacted mono-vinyl terminated polyether oligopolymer completely through wash-out, underpressure distillation, promptly obtains the polysiloxane binary alcohol of polyether block.
The structural formula of described annular siloxane is:
Figure A200810196533D00041
R in the formula 1With R 2Be CH 3, CH 2CH 3Or CH 2CH 2CH 3M=3～6;
The structural formula of described pair of hydrogen end-blocking sily oxide is:
Figure A200810196533D00051
R in the formula 1With R 2Be CH 3, CH 2CH 3And/or CH 2CH 2CH 3
Described acid catalyst is sulfuric acid or trifluoroacetic acid;
The molecular formula of described pair of hydrogen terminated polysiloxane is:
R in the formula 1And R 2Be respectively CH 3, CH 2CH 3And/or CH 2CH 2CH 3N is 1～1000 integer; The molecular weight of this pair hydrogen terminated polysiloxane is to control by the ratio of annular siloxane and two hydrogen end-blocking sily oxide, and the ratio of annular siloxane and two hydrogen end-blocking sily oxide is high more, and molecular weight is big more.
Described mono-vinyl terminated polyether structural formula is:
R in the formula 3Be H or CH 3P and q are 1～100 integer.
Described platinum metal catalyst is the Virahol alcoholic solution or the silene complexing platinum catalyst of Platinic chloride.
The polysiloxane binary alcohol of the polyether block by method for preparing of the present invention is characterized in that structural formula is:
Figure A200810196533D00054
R in the formula 1And R 2Be respectively CH 3, CH 2CH 3And/or CH 2CH 2CH 3R 3Be H or CH 3N is 1～1000 integer; P and q are 1～100 integer.
Compare with existing polysiloxane binary alcohol,, have package stability preferably on molecular chain structure because the polysiloxane binary alcohol of polyether block of the present invention is not easy to dewater or the group of Cheng Huan; Owing to introduced the polarity polyether segment at polysiloxane segment two ends, increased the polarity of polysiloxane binary alcohol, improved when multiple materials such as preparation urethane, polyester and the consistency of other component, thereby improved the lower shortcoming of existing polysiloxane binary alcohol reactive behavior, can issue the ammonifying esterification in a small amount of even solvent-free condition, be very suitable for the preparation and the modification of aqueous, environmental protective coating, tackiness agent etc.
Preparation method of the present invention is owing to the length and the kind of polyether block in the polysiloxane binary alcohol of polyether block can change according to different needs, and the scope of application enlarges; Can control the molecular weight of polysiloxane block by the ratio of regulating annular siloxane and two hydrogen end-blocking sily oxide, thereby can prepare the polysiloxane binary alcohol of the polyether block of different polyether blocks, different molecular weight according to actual needs.
More than in molecular chain structure design and the advantage on the preparation method, make that the present invention is being to have higher using value and wide Application Areas in the macromolecular material design of intermediate and the preparation with the polysiloxane binary alcohol.
Description of drawings
Fig. 1 is for the polysiloxane binary alcohol of the polyether block of the inventive method preparation 1The H nmr spectrum.
Fig. 2 is the Fourier transform infrared spectroscopy figure of the polysiloxane binary alcohol of the polyether block of the inventive method preparation.
Embodiment
Embodiment 1:
With 149.0g octamethylcyclotetrasiloxane (D 4) and the 13.4g tetramethyl disiloxane add an exsiccant and be furnished with in the 500mL there-necked flask of thermometer, prolong and stirring, add the 1.62g vitriol oil again, at 45 ℃ of reaction 48h; With deionized water product is washed, underpressure distillation obtains the two end capped polysiloxane of hydrogen (HPDMS) of 146g line style.
In the 500mL there-necked flask, add above-mentioned 146g HPDMS, add the end capped polyoxyethylene of 80.5g monoene propyl group (MAPEO, M again n=350), add platinum acid chloride solution 0.65mL when being warming up to 80 ℃, continue to be warmed up to 100 ℃ and at 100 ℃ of reaction 5h.Behind unreacted MAPEO of deionized water flush away and catalyzer,, obtain the polysiloxane binary alcohol 216g of polyether block through underpressure distillation.
Accompanying drawing 1 has provided the present embodiment final product 1The H nmr spectrum, the upper left corner is the enlarged view of chemical shift (δ) in 0.3～3.5 interval among the figure.The triplet that δ is positioned at 0.49ppm is the proton absorption peak that is connected the methylene radical on the Siliciumatom, has proved the generation of silicon H-H reaction, and the polyoxyethylene oligopolymer successfully is connected on the two ends of polysiloxane.Silicon methyl (Si-CH 3) and oxyethylene group (O-CH 2-CH 2-δ O) is respectively 0.02～0.09 and 3.57～3.68ppm, and the ownership at other peak is respectively δ=1.58 (m, C-CH 2-C), δ=2.58 (OH), δ=3.39 (t, C-C-CH 2).
Accompanying drawing 2 has provided the Fourier transform infrared spectroscopy figure of present embodiment final product.As shown in Figure 2, in the product except the charateristic avsorption band that has linear polysiloxanes (1028,1093cm -1) and the charateristic avsorption band of silicon methyl (1260,801cm -1) outside, the methylene radical absorption peak in the polyoxyethylene (2935,2871,1410cm -1) and hydroxyl (3475cm -1) charateristic avsorption band also occur, illustrate that the polyoxyethylene oligopolymer successfully inserts polysiloxane.
Analytical results by above-mentioned nmr spectrum and infrared spectrogram proves that products therefrom is the polysiloxane binary alcohol of polyether block.
Embodiment 2:
With 238.4g D 4Add an exsiccant with the 13.4g tetramethyl disiloxane and be furnished with in the 500mL there-necked flask of thermometer, prolong and stirring, add the 1.26g trifluoroacetic acid again, at 45 ℃ of reaction 72h; With deionized water product is washed, underpressure distillation obtains 213g HPDMS.
In the 500mL there-necked flask, add above-mentioned 213g HPDMS, add 80.5g MAPEO (M again n=350), add platinum acid chloride solution 0.89mL when being warming up to 80 ℃, continue to be warmed up to 100 ℃ and at 100 ℃ of reaction 5h.Behind unreacted MAPEO of deionized water flush away and catalyzer,, obtain the polysiloxane binary alcohol 281g of polyether block through underpressure distillation.
The infrared spectrogram of gained final product is with accompanying drawing 2.
Embodiment 3:
With 112g hexamethyl cyclotrisiloxane (D 3) and the 13.4g tetramethyl disiloxane add an exsiccant and be furnished with in the 500mL there-necked flask of thermometer, prolong and stirring, add the 1.3g vitriol oil again, at 45 ℃ of reaction 48h; With deionized water product is washed, underpressure distillation obtains 118g HPDMS.
In the 500mL there-necked flask, add above-mentioned 118g HPDMS, add 80.5gMAPEO (M again n=350), add platinum acid chloride solution 0.65mL when being warming up to 80 ℃, continue to be warmed up to 100 ℃ and at 100 ℃ of reaction 5h.Behind unreacted MAPEO of deionized water flush away and catalyzer,, obtain the polysiloxane binary alcohol 195g of polyether block through underpressure distillation.
The infrared spectrogram of gained final product is with accompanying drawing 2.
Embodiment 4:
With 149.0g D 4Add an exsiccant with the 13.4g tetramethyl disiloxane and be furnished with in the 500mL there-necked flask of thermometer, prolong and stirring, add the 1.62g vitriol oil again, at 45 ℃ of reaction 48h; With deionized water product is washed, underpressure distillation obtains 146g HPDMS.In the 500mL there-necked flask, add above-mentioned 146g HPDMS, add the end capped polyoxytrimethylene of 87.4g monoene propyl group (MAPPO, M again n=380), add platinum acid chloride solution 0.65mL when being warming up to 80 ℃, continue to be warmed up to 100 ℃ and at 100 ℃ of reaction 5h.Remove unreacted MAPPO and,, obtain the polysiloxane binary alcohol 220g of polyether block with n-butyl acetate extraction through underpressure distillation with behind the deionized water flush away catalyzer.
The infrared spectrogram of the polysiloxane binary alcohol of this polyether block is with accompanying drawing 2.
Reactive behavior is embodiment relatively:
Use polysiloxane binary alcohol (A, the M of the polyether block of embodiment 1 preparation n=2100), and with commercially available hydroxyl butyl end-capping polydimethylsiloxane (B, M n=2000) be reference, compare that its result is as shown in table 1 by the reactive behavior of ammonia esterification to both.
Table 1
As shown in Table 1, when temperature of reaction was 60 ℃, the reaction rate constant of the polysiloxane binary alcohol of polyether block and isophorone diisocyanate (IPDI) was 3 times of hydroxyl butyl end-capping polydimethylsiloxane; And temperature of reaction is when being 80 ℃, and the reaction rate constant of the polysiloxane binary alcohol of polyether block and tolylene diisocyanate (TDI) then is 3.5 times of hydroxyl butyl end-capping polydimethylsiloxane.The polysiloxane binary alcohol that polyether block is described has high reaction activity and high.Its reason mainly is that being introduced in of polyether segment strengthens the polysiloxane binary alcohol polar simultaneously, has also improved the consistency of polysiloxane binary alcohol and other polar material, thereby has improved mutual reactive behavior.
Package stability embodiment:
Hydroxyl is as most important functional group in the polysiloxane binary alcohol, and its variation has directly reflected the stability of polysiloxane binary alcohol, changes by the hydroxyl value of measuring polysiloxane binary alcohol under varying environment, can carry out qualitative analysis to its stability.
Table 2 has provided the hydroxyl value mutation analysis result of the polysiloxane binary alcohol of polyether block prepared in the foregoing description 1,2,3,4.
Table 2
Figure A200810196533D00081
As shown in Table 2, at room temperature placed three months and 70 ℃ through 12 hours, the polysiloxane binary alcohol hydroxyl value of polyether block does not change; Even placed 8 hours down at 100 ℃, hydroxyl value does not change substantially yet.Dehydration and annulation do not take place in the polysiloxane binary alcohol that polyether block is described, have stability preferably.The introducing of polyether block has improved the package stability of polysiloxane binary alcohol.

Claims (8)

1, a kind of preparation method of polysiloxane binary alcohol of polyether block is characterized in that: earlier with annular siloxane and two hydrogen end-blocking sily oxide in molar ratio 20～2:1 react 48～72h with the acid catalyst of press reactant total mass 0.5～2% at 40～60 ℃; Post reaction mixture through deionized water wash-out catalyzer, distill out unreacted completely behind the annular siloxane, obtain two hydrogen terminated polysiloxanes; Again two hydrogen terminated polysiloxanes and mono-vinyl terminated polyether oligopolymer are pressed every gram reactant 10～35 μ g platinum metal catalyst 70～80 ℃ of addings, at 80～120 ℃ of reaction 4～8h; Reaction product is removed catalyzer and unreacted mono-vinyl terminated polyether oligopolymer completely through wash-out, underpressure distillation, promptly obtains the polysiloxane binary alcohol of polyether block.
2, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that the structural formula of described annular siloxane is:
R in the formula 1With R 2Be CH 3, CH 2CH 3Or CH 2CH 2CH 3M=3～6.
3, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that the structural formula of described pair of hydrogen end-blocking sily oxide is:
Figure A200810196533C00022
R in the formula 1With R 2Be CH 3, CH 2CH 3And/or CH 2CH 2CH 3
4, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that described acid catalyst is sulfuric acid or trifluoroacetic acid.
5, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that the molecular formula of described pair of hydrogen terminated polysiloxane is:
Figure A200810196533C00023
R in the formula 1And R 2Be respectively CH 3, CH 2CH 3And/or CH 2CH 2CH 3N is 1～1000 integer.
6, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that described mono-vinyl terminated polyether structural formula is:
Figure A200810196533C00024
R in the formula 3Be H or CH 3P and q are 1～100 integer.
7, the preparation method of the polysiloxane binary alcohol of polyether block according to claim 1 is characterised in that described platinum metal catalyst is the Virahol alcoholic solution or the silene complexing platinum catalyst of Platinic chloride.
8, a kind of polysiloxane binary alcohol of the polyether block by the preparation of the described method of claim 1 is characterized in that structural formula is:
Figure A200810196533C00031
R in the formula 1And R 2Be respectively CH 3, CH 2CH 3And/or CH 2CH 2CH 3R 3Be H or CH 3N is 1～1000 integer; P and q are 1～100 integer.
CN2008101965336A 2008-09-10 2008-09-10 Polysiloxane binary alcohol with polyether block and preparation method thereof Active CN101381462B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2008101965336A CN101381462B (en) 2008-09-10 2008-09-10 Polysiloxane binary alcohol with polyether block and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2008101965336A CN101381462B (en) 2008-09-10 2008-09-10 Polysiloxane binary alcohol with polyether block and preparation method thereof

Publications (2)

Publication Number Publication Date
CN101381462A true CN101381462A (en) 2009-03-11
CN101381462B CN101381462B (en) 2011-01-19

Family

ID=40461528

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2008101965336A Active CN101381462B (en) 2008-09-10 2008-09-10 Polysiloxane binary alcohol with polyether block and preparation method thereof

Country Status (1)

Country Link
CN (1) CN101381462B (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102532478A (en) * 2012-02-17 2012-07-04 北京光华纺织集团有限公司 Method for synthesizing organosilicon modified polyurethane
CN102587144A (en) * 2012-02-17 2012-07-18 北京光华纺织集团有限公司 Preparation method for aramid fiber-organic silicon composite material
CN103497339A (en) * 2013-09-29 2014-01-08 淮安凯悦科技开发有限公司 Hydroxyl polyether-terminated polydimethylsiloxane and blue light emulsion of hydroxyl polyether-terminated polydimethylsiloxane as well as preparation method of blue light emulsion
CN103827217A (en) * 2012-02-03 2014-05-28 Lg化学株式会社 Novel polyorganosiloxane, polycarbonate resin composition comprising same, and modified polycarbonate resin
CN103897194A (en) * 2014-03-07 2014-07-02 浙江大学 Method for synthesizing tertiary hydroxyl terminated polysiloxane
CN103897191A (en) * 2014-02-20 2014-07-02 合肥市科天化工有限公司 Preparation method of hydroxy-terminated polysiloxane polyol
CN104004146A (en) * 2014-05-21 2014-08-27 深圳天鼎精细化工制造有限公司 Urethane-organic silicon-acrylic ester ternary polymerization emulsion and preparation method thereof
CN104448205A (en) * 2014-12-24 2015-03-25 四川达威科技股份有限公司 Waterborne polyurethane, as well as preparation method and application thereof in coating agent
CN105693980A (en) * 2016-04-14 2016-06-22 南通斯恩特纺织科技有限公司 Blocked organosilicone waterborne polyurethane anti-fluffing-and-pilling agent
CN105693989A (en) * 2016-04-14 2016-06-22 南通曙光染织有限公司 Preparation method of blocked organosilicone waterborne polyurethane anti-fluffing-and-pilling agent
CN107447524A (en) * 2017-08-11 2017-12-08 深圳市尼森实业有限公司 A kind of synthetic method of environmental type textile antibacterial finish agent
CN107987790A (en) * 2017-12-11 2018-05-04 浙江工业大学 A kind of silicone polyether base rubber of low viscosity and preparation method thereof
EP3336129A1 (en) * 2016-12-16 2018-06-20 Henkel AG & Co. KGaA Process for the preparation of hydroxyl-functionalized polysiloxanes
CN114026153A (en) * 2019-06-24 2022-02-08 美国陶氏有机硅公司 Organic silicon polyether foam control agent
CN116041651A (en) * 2022-12-15 2023-05-02 中国石油大学(北京) Organosilicon polymer for thickening carbon dioxide, preparation method and application thereof
CN116622330A (en) * 2023-06-09 2023-08-22 东莞市百拓实业有限公司 High-adhesion UV adhesive for polarizing film and preparation method thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007533452A (en) * 2004-04-20 2007-11-22 ダウ・コーニング・コーポレイション Silicone vesicles
US7834082B2 (en) * 2007-01-17 2010-11-16 Bayer Materialscience Llc Polyether-polysiloxane polyols

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103827217A (en) * 2012-02-03 2014-05-28 Lg化学株式会社 Novel polyorganosiloxane, polycarbonate resin composition comprising same, and modified polycarbonate resin
CN102587144A (en) * 2012-02-17 2012-07-18 北京光华纺织集团有限公司 Preparation method for aramid fiber-organic silicon composite material
CN102532478A (en) * 2012-02-17 2012-07-04 北京光华纺织集团有限公司 Method for synthesizing organosilicon modified polyurethane
CN102532478B (en) * 2012-02-17 2014-04-16 北京光华纺织集团有限公司 Method for synthesizing organosilicon modified polyurethane
CN103497339B (en) * 2013-09-29 2015-08-05 淮安凯悦科技开发有限公司 The polydimethylsiloxane of hydroxy polyethers end-blocking and blue light emulsion thereof and blue light emulsion preparation method
CN103497339A (en) * 2013-09-29 2014-01-08 淮安凯悦科技开发有限公司 Hydroxyl polyether-terminated polydimethylsiloxane and blue light emulsion of hydroxyl polyether-terminated polydimethylsiloxane as well as preparation method of blue light emulsion
CN103897191A (en) * 2014-02-20 2014-07-02 合肥市科天化工有限公司 Preparation method of hydroxy-terminated polysiloxane polyol
CN103897191B (en) * 2014-02-20 2016-05-11 合肥市科天化工有限公司 A kind of preparation method of hydroxy-terminated polysiloxane polyalcohol
CN103897194A (en) * 2014-03-07 2014-07-02 浙江大学 Method for synthesizing tertiary hydroxyl terminated polysiloxane
CN103897194B (en) * 2014-03-07 2016-03-30 浙江大学 A kind of synthetic method of polysiloxane of tert-hydroxyl end-blocking
CN104004146A (en) * 2014-05-21 2014-08-27 深圳天鼎精细化工制造有限公司 Urethane-organic silicon-acrylic ester ternary polymerization emulsion and preparation method thereof
CN104004146B (en) * 2014-05-21 2016-08-24 深圳天鼎精细化工制造有限公司 A kind of urethane-organic silicon-acrylate ternary copolymer emulsion and preparation method thereof
CN104448205A (en) * 2014-12-24 2015-03-25 四川达威科技股份有限公司 Waterborne polyurethane, as well as preparation method and application thereof in coating agent
CN104448205B (en) * 2014-12-24 2017-06-16 四川达威科技股份有限公司 A kind of aqueous polyurethane, its preparation method and its application for finishing agent
CN105693980A (en) * 2016-04-14 2016-06-22 南通斯恩特纺织科技有限公司 Blocked organosilicone waterborne polyurethane anti-fluffing-and-pilling agent
CN105693989A (en) * 2016-04-14 2016-06-22 南通曙光染织有限公司 Preparation method of blocked organosilicone waterborne polyurethane anti-fluffing-and-pilling agent
EP3336129A1 (en) * 2016-12-16 2018-06-20 Henkel AG & Co. KGaA Process for the preparation of hydroxyl-functionalized polysiloxanes
WO2018108863A1 (en) * 2016-12-16 2018-06-21 Henkel Ag & Co. Kgaa Process for the preparation of hydroxyl-functionalized polysiloxanes
US20190322808A1 (en) * 2016-12-16 2019-10-24 Henkel Ag & Co. Kgaa Process for the Preparation of Hydroxyl-Functionalized Polysiloxanes
US11326027B2 (en) * 2016-12-16 2022-05-10 Henkel Ag & Co. Kgaa Process for the preparation of hydroxyl-functionalized polysiloxanes
CN107447524A (en) * 2017-08-11 2017-12-08 深圳市尼森实业有限公司 A kind of synthetic method of environmental type textile antibacterial finish agent
CN107987790A (en) * 2017-12-11 2018-05-04 浙江工业大学 A kind of silicone polyether base rubber of low viscosity and preparation method thereof
CN114026153A (en) * 2019-06-24 2022-02-08 美国陶氏有机硅公司 Organic silicon polyether foam control agent
CN114026153B (en) * 2019-06-24 2022-06-07 美国陶氏有机硅公司 Organic silicon polyether foam control agent
CN116041651A (en) * 2022-12-15 2023-05-02 中国石油大学(北京) Organosilicon polymer for thickening carbon dioxide, preparation method and application thereof
CN116622330A (en) * 2023-06-09 2023-08-22 东莞市百拓实业有限公司 High-adhesion UV adhesive for polarizing film and preparation method thereof

Also Published As

Publication number Publication date
CN101381462B (en) 2011-01-19

Similar Documents

Publication Publication Date Title
CN101381462B (en) Polysiloxane binary alcohol with polyether block and preparation method thereof
CN102408569B (en) Dual-curable polysiloxane acrylate resin and preparation method thereof
CN103897194B (en) A kind of synthetic method of polysiloxane of tert-hydroxyl end-blocking
CN102408565B (en) Preparation method for phenyl hydrogen-containing silicone oil
CN108003348B (en) Siloxane bridged ladder-shaped polysiloxane, preparation method and application thereof
FI103051B (en) New block copolymers and their manufacture
CN101260190A (en) Multiple functionality degree polysiloxane coupling agent and preparation method thereof
CN103709407A (en) Preparation method of phenyl silicone oil
CN107226907A (en) A kind of method of anhydrous synthesizing organo-silicon oxygen alkane resin and product and application
CN107868647A (en) A kind of silane modified polyether base rubber and its sulfydryl alkene addition preparation method
KR101317776B1 (en) Phenylpolysiloxane resin of core-shell structure
CN103059306A (en) High-refractive index transparent silicone resin and preparation method thereof
CN107118350A (en) A kind of epoxy and phenyl silicones and preparation method and application
KR20110094080A (en) Emulsion, method for producing the same, and cosmetic raw material formed from the same
CN110452386B (en) Preparation and application of polyfunctional group POSS type organic silicon curing agent
CN104558611B (en) A kind of MDTQ silicones and its preparation method and application
JPH0562614B2 (en)
TW202041575A (en) A method for preparing polyorganosiloxanes
CN101824150A (en) Aryl-containing polysiloxane and preparation method thereof
EP3363847A1 (en) Method for producing hydrosilyl-group-containing organic silicon resin
CN106046302B (en) The preparation method of silicone-modified carborane polyurethane
CN113105632A (en) Hyperbranched organic silicon modified epoxy resin and preparation method and application thereof
CN109535427A (en) A kind of preparation method of ethenyl blocking fluorosilicon oil
CN108047451A (en) A kind of Polycaprolactone modified polysiloxanes, Preparation method and use
CN103204994A (en) Preparation method of phenyl silicon resin

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CP01 Change in the name or title of a patent holder

Address after: 230026 Jinzhai Road, Anhui, China, No. 96, No.

Co-patentee after: Hefei Scisky Technology Co., Ltd.

Patentee after: University of Science and Technology of China

Address before: 230026 Jinzhai Road, Anhui, China, No. 96, No.

Co-patentee before: Hefei Ketian Chemical Co., Ltd.

Patentee before: University of Science and Technology of China

CP01 Change in the name or title of a patent holder
TR01 Transfer of patent right

Effective date of registration: 20211014

Address after: 730000 Ketian water science and Technology Industrial Park, 3949 Kunlun Mountain Avenue, Lanzhou New District, Lanzhou City, Gansu Province

Patentee after: LANZHOU SCISKY TECHNOLOGY Co.,Ltd.

Address before: 230026 No. 96, Jinzhai Road, Hefei, Anhui

Patentee before: University of Science and Technology of China

Patentee before: LANZHOU SCISKY TECHNOLOGY Co.,Ltd.

TR01 Transfer of patent right
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20090311

Assignee: Lanzhou Keshi Sicily Health Technology Co.,Ltd.

Assignor: LANZHOU SCISKY TECHNOLOGY CO.,LTD.

Contract record no.: X2021620000016

Denomination of invention: Polyether block polysiloxane diol and preparation method thereof

Granted publication date: 20110119

License type: Exclusive License

Record date: 20211116

EE01 Entry into force of recordation of patent licensing contract