CN103937001B - Water dispersibles the preparation method of type alkyl/polyethers amino silicone - Google Patents
Water dispersibles the preparation method of type alkyl/polyethers amino silicone Download PDFInfo
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Abstract
The invention discloses a kind of water and dispersible the preparation method of type alkyl/polyethers amino silicone, first Silicon Containing Hydrogen resin is carried out hydrosilylation addition reaction, synthesis of alkyl/epoxy radicals silicones intermediate with little molecule thiazolinyl epoxide, alhpa olefin in the ratio that Si H key and thiazolinyl C=C double bond mol ratio are 1:1.0 1.5 by the present invention;Then, then intermediate and polyetheramine are carried out ammonolysis ring-opening reaction at 45 120 DEG C, can be prepared by alkyl/polyethers amino silicone.Solubilized or be dispersed in water in stable silicon breast or microemulsion, so that silicones is expected to be used for aqueous finishing agent or coated coating field after alkyl prepared by the present invention/polyethers amino silicone solvent dilution.
Description
Technical field
The invention belongs to organic siliconresin field, be specifically related in a kind of emulsifiable decentralized of water, structure
It is connected with the preparation method of the organic siliconresin of Long carbon chain alkyl and polyethers amino group simultaneously.
Background technology
Organic siliconresin i.e. with Si-O-Si as main chain, side chain connect other organic groups, structure is height
Degree crosslinking net, the trapezoidal or semiclosed isostructural siloxane polymer of caged.Silicones has concurrently organic
Resin and the double grading of inorganic material, have the heat-resistant stability of excellence, electrical insulating property, weather-proof anti-
Aqueous, Defend salt fog, mould proof and biocompatibility, can be widely applied to Aero-Space, military project,
The fields such as electric, rubber plastic, leather, Material Processing and Modif ication.
In organic siliconresin, if connected organic group structure is different from kind, then the property of silicones
Can there is notable difference, such as epoxy radicals silicones, have both combining of epoxide and organic siliconresin
Close performance, can heat-resisting, anticorrosion, oil resistant, protection against the tide, insulation, again can low-temperature setting, therefore high temperature resistant
The aspects such as weather-resistant coating, high-temperature service anticorrosion and organic silicon insulating varnish preparation are widely used.And it is hydrogeneous
Silicones and ethylene silicones, then because structure contains reactable Si--H bond and vinyl group, therefore
The aspects such as the preparation that can be used for add-on type sulphurated siliastic, LED fluid sealant.
Silicones is the most water insoluble, is mainly used in oil-soluble system, which has limited silicones in aqueous
Application in system.At present, although a lot of with the research report of application about silicones synthesis both at home and abroad,
But there is not yet relevant water and dispersible the patent report of type alkyl/polyethers amino silicone.
Summary of the invention
It is an object of the invention to disclose a kind of water and dispersible the preparation of type alkyl/polyethers amino silicone
Method.
For reaching above-mentioned purpose, present invention employs techniques below scheme:
1) Silicon Containing Hydrogen resin and raw material containing thiazolinyl press in Silicon Containing Hydrogen resin Si--H bond and containing alkene
In the raw material of base, the ratio that mol ratio is 1:1.0-1.5 of thiazolinyl (C=C) directly mixes or in a solvent
Mixing, then carries out hydrosilylation addition reaction and prepares alkyl/epoxy radicals silicones intermediate, described contains
The raw material of thiazolinyl is made up of little molecule thiazolinyl epoxide and alpha-olefin, little molecule thiazolinyl epoxidation
Compound is 4-10:1 with the mol ratio of alpha-olefin;
2) alkyl/epoxy radicals silicones intermediate and polyetheramine are pressed alkyl/epoxy radicals silicones intermediate
Epoxy group mixes with the ratio that mol ratio is 1:1-1.2 of polyetheramine, then carries out ammonolysis ring-opening reaction
Obtain alkyl/polyethers amino silicone.
Described Silicon Containing Hydrogen resin is to contain Si--H bond and trifunctional Si-O key in structure and tie in topology
The siloxane polymer of structure (such as structures such as dendroid, netted, caged).
Described Silicon Containing Hydrogen resin is that methyl hydrogen silicones, phenyl Silicon Containing Hydrogen resin, aminomethyl phenyl are hydrogeneous
Silicones or hydrogeneous MQ silicones, the Si--H bond content of Silicon Containing Hydrogen resin is (with every 100g silicones
Contained by, the molal quantity of Si--H bond represents) it is 0.1-0.8%, viscosity is 100-6000mPa s.
Described little molecule thiazolinyl epoxide is allyl glycidyl ether, glycidyl acrylate
Or glycidyl methacrylate.
Described alpha-olefin is containing C8-18Alpha-carbon alkene, such as α-octene, α-dodecylene, α-ten six carbon
Alkene or α-vaccenic acid etc..
Described solvent is that alcohol, alcohol ether or ether-ether (mainly include isopropanol, the tert-butyl alcohol, ethylene glycol list first
Ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, the third two
Alcohol monobutyl ether or propylene glycol methyl ether acetate etc.) in any one mixture with toluene, solvent load
For the 0-200% of Silicon Containing Hydrogen resin quality, alcohol, alcohol ether or ether-ether are 1:1-2 with the mass ratio of toluene.
Described hydrosilylation addition reaction is at stirring and N2Carrying out under protection, reaction temperature is 70-100
DEG C, the response time is 0.5-6h, described hydrosilylation addition reaction use catalyst be chloroplatinic acid, 1,3-
Divinyl tetramethyl disiloxane closes platinum complex, 1,3-dimethyl-1,3-diphenyl-1,3-divinyl
Siloxanes closes platinum complex or 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl cyclotetrasiloxane closes platinum and coordinates
Thing.
Described alkyl/epoxy radicals silicones intermediate is to be simultaneously connected with C in molecular structure8-18Alkyl and
Epoxy radicals, and structure is the siloxane polymer of the topological structure such as netted, dendroid.
Described polyetheramine is that end group connection has primary amino radical and mid-block to have polyoxyethylene poly-oxygen propylene aether
One in the diamine of group, the mean molecule quantity of polyetheramine is 230-1000, mainly includes polyethers
Amine D230, D400, ED-600, ED-900 etc., can be directly from Huntsman company of the U.S. or raise
Zhou Chenhua Group Co., Ltd buys.
The reaction temperature of described ammonolysis ring-opening reaction is 45-120 DEG C, and the response time is 1-4h, reaction knot
Unreacted low-boiling-point substance and solvent are evaporated off after bundle.
Described alkyl/polyethers amino silicone is to be connected with C in molecular structure simultaneously8-18Alkyl and polyethers ammonia
Base group and structure are netted or the siloxane polymer of the topological structure such as dendroid.
Beneficial effects of the present invention is embodied in:
Silicon Containing Hydrogen resin and little molecule thiazolinyl epoxide, alpha-olefin are first carried out silicon hydrogenation by the present invention
Additive reaction synthesis of alkyl/epoxy radicals silicones intermediate, then, then exists intermediate and polyetheramine
45-120 DEG C carries out ammonolysis ring-opening reaction synthesis of alkyl/polyethers amino silicone, is drawn by polyethers amino group
Enter in silicones structure, the water solublity of silicones, automatic emulsifying performance and ion-type can not only be improved, and
And the range of application of silicones can be made to be extended to water-based system such as organic silicone finishing agent, water paint and painting
The fields such as layer.
Detailed description of the invention
Below in conjunction with embodiment, the invention will be further described, but the present invention is not restricted to these in fact
Execute example.
Embodiment 1
It is sequentially added in the there-necked flask equipped with thermometer, reflux condensing tube and motor stirrer
30g viscosity is 2080mPa s, Si--H bond content is that the methyl hydrogen silicones of 0.2% is (containing Si-H
Key 0.06mol), 5.7g (0.05mol) allyl glycidyl ether and 1.14g (0.01mol) α-octene,
Then at stirring and logical N2It is heated to 70 DEG C under protection, then in there-necked flask, adds 20ppm
Catalyst chloroplatinic acid insulation reaction 6h, is down to room temperature and obtains total amount about 36.84g water white transparency liquid after reaction
Body, i.e. intermediate octyl group/2,3-epoxypropoxy silicones (is called for short octyl group/epoxy radicals silicones),
Containing epoxy radicals about 0.05mol.
13.8g(0.06mol is continuously added in intermediate) polyetheramine D230, after stirring and evenly mixing, then
It is heated to 120 DEG C of reaction 1h.Reaction terminate after gauge pressure be 600mmHg, temperature be 80 DEG C
Under the conditions of remove unreacted low-boiling-point substance under reduced pressure, obtain the sticky shape of water white transparency or slightly troubled liquor, i.e. octyl group
/ polyethers amino silicone-230, content about 100%.
Embodiment 2
It is sequentially added in the there-necked flask equipped with thermometer, reflux condensing tube and motor stirrer
30g viscosity is 5900mPa s, Si--H bond content is that the methyl hydrogen silicones of 0.1% is (containing Si-H
Key 0.03mol), 4.62g (0.0405mol) allyl glycidyl ether and 0.76g (0.0045mol) α-
Dodecylene, then at stirring and logical N2100 DEG C it are heated under protection, then to there-necked flask
Middle addition 50ppm catalyst chloroplatinic acid insulation reaction 0.5h, is then 500mmHg, temperature in gauge pressure
Degree is 100 DEG C and removes excess allyl glycidyl ether under reduced pressure, is down to room temperature and obtains total amount about 33.67g's
Water white transparency thick liquid, i.e. intermediate dodecyl/epoxy radicals silicones, containing epoxy radicals about
0.0255mol。
7.04g(0.0306mol is continuously added in intermediate) polyetheramine D230, add after stirring and evenly mixing
Heat is warming up to 45 DEG C of reaction 4h.Reaction terminate after gauge pressure be 600mmHg, temperature be 80 DEG C of conditions
Under remove unreacted low-boiling-point substance under reduced pressure, obtain water white transparency shape thick liquid, i.e. dodecyl/polyethers amino
Silicones-230, content about 100%.
Embodiment 3
It is sequentially added in the there-necked flask equipped with thermometer, reflux condensing tube and motor stirrer
30g viscosity is 130mPa s, Si--H bond content is that the hydrogeneous MQ silicones of 0.8% is (containing Si--H bond
0.24mol), 22.98g (0.2016mol) allyl glycidyl ether, 12.7g (0.0504mol) α-ten
Eight carbenes and 60g isopropanol-toluene Mixed Solvent (isopropanol: the mass ratio=1:1 of toluene), then
At stirring and logical N2It is heated to 80 DEG C under protection, then addition 20ppm urges in there-necked flask
Agent 1,3-divinyl tetramethyl disiloxane is closed platinum complex insulation reaction 3h, is down to room after reaction
The warm water white transparency thick liquid obtaining total amount about 125.68g, i.e. intermediate octadecyl/epoxy radicals silicon tree
The solution of fat, containing epoxy radicals about 0.2016mol.
To the solution of intermediate continuously adds 80.64g(0.2016mol) polyetheramine D400, stirring
Mixing post-heating is warming up to 60 DEG C of reaction 2h.Reaction terminates, and reclaims isopropanol at 85 DEG C of first normal pressures,
The most again gauge pressure be 600mmHg, temperature be 90 DEG C under the conditions of remove toluene under reduced pressure and other are low
Boiling thing, obtains translucent thick liquid, i.e. octadecyl/polyethers amino silicone-400, content about 100%.
Embodiment 4
It is sequentially added in the there-necked flask equipped with thermometer, reflux condensing tube and motor stirrer
The aminomethyl phenyl Silicon Containing Hydrogen resin that 20g viscosity is 3600mPa s, Si--H bond content is 0.3% (contains
Si--H bond 0.06mol), 7.68g (0.054mol) glycidyl methacrylate, 0.68g (0.006mol)
α-octene and 30g propylene glycol monomethyl ether-toluene Mixed Solvent (propylene glycol monomethyl ether: the quality of toluene
Ratio=1:2), then at stirring and logical N285 DEG C it are heated under protection, then in there-necked flask
Add 25ppm catalyst 1,3-dimethyl-1,3-diphenyl-1,3-divinylsiloxanes and close platinum complex
Insulation reaction 2h, is down to room temperature and obtains the water white transparency thick liquid of total amount about 58.36g, i.e. after reaction
The solution of intermediate octyl group/epoxy radicals silicones, containing epoxy radicals about 0.054mol.
34.0g(0.0567mol is continuously added in the solution of intermediate) polyetheramine ED-600, stirring
Mixing post-heating is warming up to 80 DEG C of reaction 3h.Reaction terminates, gauge pressure be 600mmHg, temperature be
Remove toluene and propylene glycol monomethyl ether and low-boiling-point substance under the conditions of 100-120 DEG C under reduced pressure, obtain water white transparency-
Slightly muddy thick liquid, i.e. octyl group/polyethers amino silicone-600, content about 100%.
Embodiment 5
It is sequentially added in the there-necked flask equipped with thermometer, reflux condensing tube and motor stirrer
The aminomethyl phenyl Silicon Containing Hydrogen resin that 10g viscosity is 1060mPa s, Si--H bond content is 0.5% (contains
Si--H bond 0.05mol), 5.23g (0.0459mol) allyl glycidyl ether, 1.14g (0.005mol) α-
Hexadecene and 20g propylene glycol methyl ether acetate-toluene Mixed Solvent (propylene glycol methyl ether acetate:
Mass ratio=the 1:1 of toluene), then at stirring and logical N285 DEG C it are heated under protection, then to
There-necked flask adds 15ppm catalyst 1,3-dimethyl-1,3-diphenyl-1-3-divinylsiloxanes
Close platinum complex insulation reaction 1.5h, be down to after reaction room temperature obtain total amount about 36.37g water white transparency stick
Thick liquid, the i.e. solution of intermediate cetyl/epoxy radicals silicones, epoxy silicone content is about
16.37g, containing epoxy radicals about 0.0459mol.
41.9g(0.0459mol is continuously added in the solution of intermediate) polyetheramine ED-900, stirring
Mixing post-heating is warming up to 110 DEG C of reaction 4h.Reaction is 600mmHg, temperature in gauge pressure after terminating
Under the conditions of 100-120 DEG C, remove solvent and low-boiling-point substance under reduced pressure, obtain water white transparency-translucent viscous fluid
Body, i.e. cetyl/polyethers amino silicone-900, content about 100%.
Alkyl prepared by Example 1-5/polyethers amino silicone spent glycol butyl ether is diluted to 50%,
Adjust pH to be about 6 with acetic acid, then add water and use dispersion machine emulsifying, make the silicon breast that solid content is 15%,
After placing one day, evaluate silicon breast outward appearance with ocular estimate, be the centrifuge of 3000r/m with rotating speed
15min evaluates the relative stability of silicon breast, and reference is the Silicon Containing Hydrogen tree of non-modified in embodiment 1-5
Fat (oil-soluble).Experimental result is shown in Table 1.
The easy emulsifiability of table 1 alkyl/polyethers amino silicone and the performance of relevant emulsion
* dewatering ability: 3000r/m × 15min
From table 1 it follows that chain alkyl/polyethers amino silicone tree prepared by embodiment of the present invention 1-5
Fat water solublity is good, good with its silicon breast dewatering ability made in the presence of butyl glycol ether, and
The Silicon Containing Hydrogen resin of non-modified, insoluble in water, it is dispensed into the emulsion made in water not by force
Stable, easily it is layered floating oil.Visible, alkyl/polyethers amino silicone prepared by the present invention has really
Water-dispersible.
Claims (10)
1. a water dispersibles the preparation method of type alkyl/polyethers amino silicone, it is characterised in that:
Comprise the following steps:
1) by Silicon Containing Hydrogen resin with the raw material containing thiazolinyl by the mol ratio of Si--H bond with thiazolinyl it is
The ratio of 1:1.0-1.5 directly mixes or mixes in a solvent, then carries out hydrosilylation addition reaction and prepares
Alkyl/epoxy radicals silicones intermediate, the described raw material containing thiazolinyl is by little molecule thiazolinyl epoxide
And alpha-olefin composition, little molecule thiazolinyl epoxide is 4-10:1 with the mol ratio of alpha-olefin;
2) alkyl/epoxy radicals silicones intermediate and polyetheramine are pressed alkyl/epoxy radicals silicones intermediate
Epoxy group mixes with the ratio that mol ratio is 1:1-1.2 of polyetheramine, then carries out ammonolysis ring-opening reaction
Obtain alkyl/polyethers amino silicone.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described Silicon Containing Hydrogen resin is containing Si--H bond and trifunctional Si-O in structure
Key and the siloxane polymer in topological structure.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described Silicon Containing Hydrogen resin be methyl hydrogen silicones, phenyl Silicon Containing Hydrogen resin,
Aminomethyl phenyl Silicon Containing Hydrogen resin or hydrogeneous MQ silicones, the Si--H bond content of Silicon Containing Hydrogen resin is
0.1-0.8%, viscosity is 100-6000mPa s.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described little molecule thiazolinyl epoxide be allyl glycidyl ether, third
Olefin(e) acid ethylene oxidic ester or glycidyl methacrylate.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described alpha-olefin is containing C8-18Alpha-carbon alkene.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described solvent is any one mixing with toluene in alcohol, alcohol ether or ether-ether
Thing, solvent load is the 0-200% of Silicon Containing Hydrogen resin quality, alcohol, alcohol ether or ether-ether and the matter of toluene
Amount ratio is 1:1-2.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described hydrosilylation addition reaction is at stirring and N2Carry out under protection, instead
Answering temperature to be 70-100 DEG C, the response time is 0.5-6h, the catalysis that described hydrosilylation addition reaction uses
Agent is chloroplatinic acid, 1,3-divinyl tetramethyl disiloxane conjunction platinum complex, 1,3-dimethyl-1,3-two
Phenyl-1,3-divinylsiloxanes closes platinum complex or 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl ring
Tetrasiloxane closes platinum complex.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described polyetheramine is that end group connection has primary amino radical and mid-block to have polyoxy
One in the diamine of ethylene polyoxypropylene ether group, the mean molecule quantity of polyetheramine is
230-1000。
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: the reaction temperature of described ammonolysis ring-opening reaction is 45-120 DEG C, the response time
For 1-4h.
A kind of water dispersibles the preparation of type alkyl/polyethers amino silicone
Method, it is characterised in that: described alkyl/polyethers amino silicone is to be connected with C in molecular structure simultaneously8-18
Alkyl and polyethers amino group and the siloxane polymer in topological structure.
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CN105694046A (en) * | 2016-02-06 | 2016-06-22 | 浙江汉邦化工有限公司 | Preparation method of highly-branched block polyether-aminosiloxane finishing agent |
CN105694062A (en) * | 2016-02-06 | 2016-06-22 | 陕西科技大学 | Cross-linked structure dendritic amino silicone oil and preparation method thereof |
CN107163254B (en) * | 2017-07-03 | 2021-01-29 | 陕西科技大学 | Preparation method and application of solvent type hydrophobic and oleophobic fluorocarbon silicone resin |
CN107540843B (en) * | 2017-08-31 | 2020-05-22 | 华南理工大学 | Functional assistant with side group containing long-chain alkyl and epoxy polysiloxane and preparation method thereof |
CN109096500B (en) * | 2018-07-06 | 2021-04-13 | 福建拓烯新材料科技有限公司 | Organic silicon resin microemulsion and preparation method thereof |
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CN103214679A (en) * | 2013-05-06 | 2013-07-24 | 江南大学 | Preparation method of aminopolyether modified polysiloxane deforming agent |
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CN103214679A (en) * | 2013-05-06 | 2013-07-24 | 江南大学 | Preparation method of aminopolyether modified polysiloxane deforming agent |
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