CN110078925A - A kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil - Google Patents
A kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil Download PDFInfo
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- CN110078925A CN110078925A CN201910368719.3A CN201910368719A CN110078925A CN 110078925 A CN110078925 A CN 110078925A CN 201910368719 A CN201910368719 A CN 201910368719A CN 110078925 A CN110078925 A CN 110078925A
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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Abstract
The present invention relates to a kind of preparation methods of high polymerization degree Si-O-C type block polyether modified silicon oil, and the present invention is by end containing hydrogen silicone oil and polyethylene glycol by condensation reaction in catalyst K2CO3Under the action of obtain Si-O-C type polyether modified silicon oil.Catalyst of the present invention is cheap and easy to get, is aided with suitable reaction medium, the degree of polymerization can be made to greatly improve.
Description
Technical field
The present invention relates to a kind of preparation methods of high polymerization degree Si-O-C type block polyether modified silicon oil, belong to polyurethane and help
Agent technical field.
Background technique
Polyether modified silicon oil (also referred to as polyether modified siloxane) is usually gathered by the bigger hydrophilic segment of performance difference
Ether and hydrophobic chain segment dimethicone pass through a kind of polyurethane foams stabilizers for unique properties that graft copolymerization is formed.Polyethers
The preparation method of modified silicon oil, which is usually divided, 2 kinds, it may be assumed that Si-O-C type polyether modified silicon oil and Si -- C type polyether modified silicon oil.Root
According to chain structure difference, polyether modified silicon oil is divided into side chain type and backbone chain type again, and wherein side chain type is comb-like graft copolymer, main chain
For polysiloxanes, side chain is polyethers.It because preparation process is simple, versatile, is used widely, but it is applied to extraordinary poly- ammonia
When ester foam, implacable simultaneously in performance, the processing of silicone oil is also restrained in environmental protection.In addition, polyether-modified
When silicone oil is used for special urethane foam foam stabilizer, it is desirable that there is high polymerization degree.But the increase right with polymer poly, chain
The reactivity of Duan Duanji significantly reduces, therefore the synthesis difficulty of the backbone chain type polyether modified silicon oil of high polymerization degree is larger.
The present invention is raw material using both-end containing hydrogen silicone oil and polyethylene glycol, changes traditional block under base catalyst effect
It is high poly- to greatly reduce acquisition so that technology path is simplified for the technique that polyether modified silicon oil platinum catalyst divides multistage to prepare
The difficulty of right multi-block polyether modified silicon oil, and the degree of polymerization of product greatly improves (degree of polymerization > 100).
Summary of the invention
In view of the above-mentioned problems, the present invention is by selecting suitable catalyst, simultaneously Optimizing Technical prepares high polymerization degree Si-
O-C type block polyether modified silicon oil, reaction condition is mild, easily controllable.
In order to achieve this goal, the present invention passes through condensation reaction in catalyst by end containing hydrogen silicone oil and polyethylene glycol
K2CO3Under the action of obtain Si-O-C type polyether modified silicon oil, react as follows:
Wherein: m1For the degree of polymerization for holding containing hydrogen silicone oil.
m2For the degree of polymerization of polyethylene glycol.
N is the degree of polymerization of reaction product block polyether modified silicon oil.
Specific step is as follows for the technical solution adopted by the present invention:
1) preparation of Si-O-C type block polyether modified silicon oil: weigh first a certain proportion of end containing hydrogen silicone oil, polyethylene glycol and
Reaction medium is added to equipped with thermometer, condenser pipe, is connected with N2Reactor in, start to stir, be warming up to 40 ~ 90 DEG C, be added
Catalyst K2CO3, continue after being stirred to react 15-30h, obtain the crude product containing solvent and catalyst；
2) post-processing of the crude product containing solvent and catalyst: the revolving of crude product obtained by step 1) is removed into reaction medium, then is passed through
Organic solvent lysate and Filtration of catalyst is added, revolving removes solvent, and it is poly- that finished product Si-O-C type block can be obtained
Ether modified silicon oil.
Further, the molecular weight of the step 1) middle-end containing hydrogen silicone oil is 900-1500, the molecular weight of polyethylene glycol is
200-1000, holding the molar ratio of containing hydrogen silicone oil and polyethylene glycol is 1:1.01-1.1.
Further, catalyst amount is end containing hydrogen silicone oil, polyethylene glycol and reaction medium gross mass in the step 1)
1.0-6.0%, reaction medium be n,N dimethylformamide (DMF) and tetrahydrofuran (THF) mixture, reaction medium
Additional amount is 1-2 times for holding the sum of containing hydrogen silicone oil and polyethylene glycol volume.
Further, step 1) n,N dimethylformamide and the volume ratio of tetrahydrofuran are 1:1.
Further, the method that crude product revolving removes reaction medium are as follows: first remove tetrahydrofuran in 33-45 DEG C of revolving；Again
In 60-80 DEG C of removing N, N-dimethylformamide.
Further, step 2 organic solvent is ethyl acetate or tetrahydrofuran, and organic solvent additional amount is end Silicon Containing Hydrogen
2-5 times of the sum of oily and polyethylene glycol volume.
Further, revolving remove solvent temperature be 30-60 DEG C, revolving to steam amount of substance be no longer changed for
Only.
Beneficial effects of the present invention:
High polymerization degree Si- is made by condensation alcoholysis reaction using end containing hydrogen silicone oil Si -- H bond and polyethylene glycol-OH key in the present invention
O-C type block polyether modified silicon oil.Compared with tradition prepares the synthetic method of block polyether modified silicon oil, catalyst is inexpensive easily
, it is aided with suitable reaction medium, the degree of polymerization can be made to greatly improve.
Detailed description of the invention
Fig. 1 is the GPC gel chromatography figure of the embodiment of the present invention 1, comparative example 1, comparative example 2 and comparative example 3.
Specific embodiment
It elaborates below with reference to embodiment, comparative example and Fig. 1 to the present invention.
Embodiment 1
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.195%, molecular weight: 1025), 3.978g polyethylene glycol (400) and 20mL reaction medium (THF:DMF=
1:1), 60 DEG C are slowly warming up to after stirring 15min clock, 0.5444g catalyst is added, is reacted the 18h time, revolving removes solvent,
By the way that THF lysate is added, by solution Filtration of catalyst.It is -0.85MPa hereinafter, vacuum distillation removes in vacuum degree
THF, until product quality is no longer changed.Acquired white viscous liquid is block polyether modified silicon oil.Pass through
Gel permeation chromatography GPC measures molecular weight 177447, the degree of polymerization 124.1g product is taken, is dissolved in 20ml ethyl acetate, uses specification
It is 221.38s for the Ubbelohde viscometer survey liquid flow time of 0.5-0.6.
Embodiment 2
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.1826%, molecular weight: 1025), 3.724g polyethylene glycol (400) and 13.7mL reaction medium (THF:
DMF=1:1), 50 DEG C are slowly warming up to after stirring 15min clock, 0.510g catalyst is added, is reacted the 20h time, revolving removes molten
Agent, by the way that THF lysate is added, by solution Filtration of catalyst.It is -0.85MPa hereinafter, vacuum distillation removes in vacuum degree
THF is removed, until product quality is no longer changed.1g product is taken, is dissolved in 20ml ethyl acetate, is 0.5- with specification
It is 147.37s that 0.6 Ubbelohde viscometer, which surveys liquid flow time,.
Embodiment 3
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.1826%, molecular weight: 1025), 3.724g polyethylene glycol (400) and 27.5mL reaction medium (THF:
DMF=1:1), 90 DEG C are slowly warming up to after stirring 15min clock, 0.51g catalyst is added, is reacted the 20h time, revolving removes molten
Agent, by the way that ethyl acetate lysate is added, by solution Filtration of catalyst.It is -0.85MPa hereinafter, decompression in vacuum degree
Ethyl acetate is distilled off, until product quality is no longer changed.1g product is taken, is dissolved in 20ml ethyl acetate, is used
It is 75.82s that the Ubbelohde viscometer that specification is 0.5-0.6, which surveys liquid flow time,.
Embodiment 4
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.1826%, molecular weight: 1025), 3.724g polyethylene glycol (400) and 20mL reaction medium (THF:DMF=
1:1), 40 DEG C are slowly warming up to after stirring 15min clock, 0.8213g catalyst is added, is reacted the 30h time, revolving removes solvent,
By the way that THF lysate is added, by solution Filtration of catalyst.It is -0.85MPa hereinafter, vacuum distillation removes in vacuum degree
THF, until product quality is no longer changed.1g product is taken, is dissolved in 20ml ethyl acetate, is 0.5-0.6 with specification
Ubbelohde viscometer survey liquid flow time be 118.39s.
Embodiment 5
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.1826%, molecular weight: 1025), 3.724g polyethylene glycol (400) and 20mL reaction medium (THF:DMF=
1:1), 70 DEG C are slowly warming up to after stirring 15min clock, 0.1383g catalyst is added, is reacted the 15h time, revolving removes solvent,
By the way that THF lysate is added, by solution Filtration of catalyst.It is -0.85MPa hereinafter, vacuum distillation removes in vacuum degree
THF, until product quality is no longer changed.1g product is taken, is dissolved in 20ml ethyl acetate, is 0.5-0.6 with specification
Ubbelohde viscometer survey liquid flow time be 119.35s.
Comparative example 1
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100ml four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.15%, molecular weight: 1333) with 3.06g polyethylene glycol (400), slowly it is warming up to after stirring 15min clock
60 DEG C of reaction temperature, 0.4188g catalyst is added, reacts the 18h time, by the way that ethyl acetate lysate is added, by solution mistake
Filter out catalyst.It is -0.85MPa hereinafter, vacuum distillation removes ethyl acetate, until product quality no longer occurs in vacuum degree
Until variation.Acquired white viscous liquid is block polyether modified silicon oil.Molecular weight 53459, the degree of polymerization are measured by GPC
37。
Comparative example 2
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100mL four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.195%, molecular weight: 1025), 3.978g polyethylene glycol (400) and 20mL reaction medium THF, stirring
It is slowly warming up to 60 DEG C of reaction temperature after 15min clock, 0.5444g catalyst is added, reacts the 18h time, revolving removes solvent, leads to
Addition THF lysate is crossed, by solution Filtration of catalyst.It is -0.85MPa hereinafter, vacuum distillation removes in vacuum degree
THF, until product quality is no longer changed.It is block polyether modified silicon oil that white viscous liquid, which can be obtained,.It is logical
It crosses GPC and measures molecular weight 22747, the degree of polymerization 15.1g product is taken, is dissolved in 20ml ethyl acetate, the crow for being 0.5-0.6 with specification
It is 83.08s that family name's viscosity, which measures liquid flow time,.
Comparative example 3
It is being furnished with thermometer, blender, N2Gas-guide tube, reflux condensing tube 100ml four-hole bottle in, the end 10g that metering is added contains
Hydrogen silicone oil (hydrogen content: 0.195%, molecular weight: 1025), 3.978g polyethylene glycol (400) and 20mL reaction medium DMF, stirring
It is slowly warming up to 60 DEG C of reaction temperature after 15min clock, 0.5444g catalyst is added, reacts the 18h time, revolving removes solvent, leads to
Addition ethyl acetate lysate is crossed, is -0.85MPa hereinafter, vacuum distillation removes ethyl acetate, until product matter in vacuum degree
Until amount is no longer changed.It is resulting to white viscous liquid be block polyether modified silicon oil.Molecular weight is measured by GPC
74638, the degree of polymerization 52.1g product is taken, is dissolved in 20ml ethyl acetate, surveys liquid with the Ubbelohde viscometer that specification is 0.5-0.6
Flowing time is 103.18s.
The block polyether modified silicon oil that the embodiment of the present invention 1 obtains as can be seen from Figure 1 is relative to the comparative example 1-3 degree of polymerization
It greatly improves.
Claims (7)
1. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil, which is characterized in that containing hydrogen silicone oil and poly-
Ethylene glycol is by condensation reaction in catalyst K2CO3Under the action of obtain Si-O-C type polyether modified silicon oil, reaction equation is such as
Under:
Wherein: m1For the degree of polymerization for holding containing hydrogen silicone oil；
m2For the degree of polymerization of polyethylene glycol；
N is the degree of polymerization of reaction product block polyether modified silicon oil；
Specifically comprise the following steps:
1) preparation of Si-O-C type block polyether modified silicon oil: weigh first a certain proportion of end containing hydrogen silicone oil, polyethylene glycol and
Reaction medium is added to equipped with thermometer, condenser pipe, is connected with N2Reactor in, start to stir, be warming up to 40-90 DEG C, be added
Catalyst K2CO3, continue after being stirred to react 15-30h, obtain the crude product containing solvent and catalyst；
2) post-processing of the crude product containing solvent and catalyst: the revolving of crude product obtained by step 1) is removed into reaction medium, then is passed through
Organic solvent lysate and Filtration of catalyst is added, revolving removes solvent, and it is poly- that finished product Si-O-C type block can be obtained
Ether modified silicon oil.
2. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil according to claim 1, special
Sign is that the molecular weight of the step 1) middle-end containing hydrogen silicone oil is 900-1500, the molecular weight of polyethylene glycol is 200-1000, end
The molar ratio of containing hydrogen silicone oil and polyethylene glycol is 1:1.01-1.1.
3. according to the method described in claim 1, it is characterized by: in the step 1) catalyst amount be end containing hydrogen silicone oil,
The 1.0-6.0% of polyethylene glycol and reaction medium gross mass, reaction medium are the mixing of n,N dimethylformamide and tetrahydrofuran
Object, the additional amount of reaction medium are 1-2 times for holding the sum of containing hydrogen silicone oil and polyethylene glycol volume.
4. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil according to claim 3, special
Sign is that the volume ratio of step 1) n,N dimethylformamide and tetrahydrofuran is 1:1.
5. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil according to claim 3, special
Sign is that crude product rotates the method for removing reaction medium are as follows: first removes tetrahydrofuran in 33-45 DEG C of revolving；It is removed again at 60-80 DEG C
Go N, N-dimethylformamide.
6. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil according to claim 1, special
Sign is that step 2 organic solvent is ethyl acetate or tetrahydrofuran, and organic solvent additional amount is end containing hydrogen silicone oil and poly- second two
2-5 times of the sum of alcohol volume.
7. a kind of preparation method of high polymerization degree Si-O-C type block polyether modified silicon oil according to claim 1, special
Sign is that the temperature that revolving removes solvent is 30-60 DEG C.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111778112A (en) * | 2020-07-02 | 2020-10-16 | 江西凡可科技有限公司 | Antifouling and dustproof quick-drying cleaning agent composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB892819A (en) * | 1957-05-23 | 1962-03-28 | Union Carbide Corp | Block copolymers and their production |
| WO2013096332A1 (en) * | 2011-12-21 | 2013-06-27 | Dow Corning Corporation | Polymerizable hybrid polysiloxanes and preparation |
| CN103724609A (en) * | 2013-12-31 | 2014-04-16 | 广州星业科技股份有限公司 | Modified monomer and organic modified polysiloxane prepared thereby |
-
2019
- 2019-05-05 CN CN201910368719.3A patent/CN110078925B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB892819A (en) * | 1957-05-23 | 1962-03-28 | Union Carbide Corp | Block copolymers and their production |
| WO2013096332A1 (en) * | 2011-12-21 | 2013-06-27 | Dow Corning Corporation | Polymerizable hybrid polysiloxanes and preparation |
| CN103724609A (en) * | 2013-12-31 | 2014-04-16 | 广州星业科技股份有限公司 | Modified monomer and organic modified polysiloxane prepared thereby |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111778112A (en) * | 2020-07-02 | 2020-10-16 | 江西凡可科技有限公司 | Antifouling and dustproof quick-drying cleaning agent composition |
| CN111778112B (en) * | 2020-07-02 | 2021-06-25 | 江西凡可科技有限公司 | Antifouling and dustproof quick-drying cleaning agent composition |
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