CN103897191B - A kind of preparation method of hydroxy-terminated polysiloxane polyalcohol - Google Patents
A kind of preparation method of hydroxy-terminated polysiloxane polyalcohol Download PDFInfo
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- CN103897191B CN103897191B CN201410058037.XA CN201410058037A CN103897191B CN 103897191 B CN103897191 B CN 103897191B CN 201410058037 A CN201410058037 A CN 201410058037A CN 103897191 B CN103897191 B CN 103897191B
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- terminated polysiloxane
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- polyalcohol
- polysiloxane polyalcohol
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- -1 polysiloxane Polymers 0.000 title claims abstract description 31
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 26
- 150000005846 sugar alcohols Polymers 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- 239000010703 silicon Substances 0.000 claims abstract description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 230000006837 decompression Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 241000219289 Silene Species 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 3
- 230000000536 complexating effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 229920002635 polyurethane Polymers 0.000 abstract description 6
- 239000004814 polyurethane Substances 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 4
- 238000006459 hydrosilylation reaction Methods 0.000 abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 2
- 238000007171 acid catalysis Methods 0.000 abstract 1
- AOJHDNSYXUZCCE-UHFFFAOYSA-N dimethylsilyloxy(trimethyl)silane Chemical group C[SiH](C)O[Si](C)(C)C AOJHDNSYXUZCCE-UHFFFAOYSA-N 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
The invention discloses a kind of preparation method of hydroxy-terminated polysiloxane polyalcohol, first by 1, the silicon hydrogenation of 4-dihydroxy-2-butylene and pentamethyl disiloxane forms 1,4-dihydroxy-2-butylene hydrosilation product, carry out acid catalysis ring-opening reaction with annular siloxane again, prepare hydroxy-terminated polysiloxane polyalcohol. Hydroxy-terminated polysiloxane polyalcohol cost prepared by this method is low, siloxanes is positioned at material molecule side chain simultaneously, under the prerequisite that does not reduce the mechanical property of materials, significantly reduce material surface energy, improve the resistance to water of material, be especially suitable for synthetic water-base polyurethane material.
Description
Technical field
The present invention relates to a kind of preparation method of hydroxy-terminated polysiloxane polyalcohol, belong to macromolecular material intermediateThe preparing technical field of polysiloxane polyhydric alcohol.
Background technology
Because polysiloxane polyhydric alcohol exists terminal hydroxy group, be therefore often used as intermediate and prepare polyurethane, polyester etc.Multiple material. The material of preparing as intermediate using silicone glycols has good resistance to water, ageing resistanceWith surface property and good biocompatibility etc., thereby be used widely in a lot of fields.
The method for making of the disclosed a kind of α W siloxane glycol of Chinese patent patent 90105777.0, at acidic catalystSecondary hydrolysis alkoxy silane under agent effect, thus make siloxanes two ends with hydroxy functional group. Due to silicaAlkane is connected hydroxyl poor stability directly, and not too suitable work is prepared the intermediate of the material such as polyurethane, polyester.
The polysiloxane binary alcohol of Chinese patent patent 200810196533.6 disclosed a kind of polyether blocks andPreparation method, first synthetic two hydrogen end-blocking obtains polysiloxanes, then utilizes silicon hydrogenation to access at siloxanes two endsPolyether chain, gained silicone glycols reactivity is high, good stability. But, when polyether block polysiloxanesWhen dihydroxylic alcohols is access in polyurethane chain, because siloxane chain is positioned on main chain, be unfavorable for the rich surface of siloxanesCollection.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of hydroxy-terminated polysiloxane polyalcohol, existing to overcomeLow, the water-fast guards escorting prisoners of polysiloxane binary alcohol reactivity, high in cost of production problem are improved silicone-modified common simultaneouslyMechanical performance when polymers.
Its technical scheme is: a kind of preparation method of hydroxy-terminated polysiloxane polyalcohol, is characterized in that: first willPentamethyl disiloxane and 1,4 ?Er Qiang Ji ?2 ?butylene add in reactor 1:1.2～1 in molar ratio, 70～80 DEG C time, add the platinum metal catalyst of 10～35 μ g by every gram of reactant quality, and 80～120 DEG C of conditionsLower reaction 4～8h; Unreacted pentamethyl disiloxane is removed in decompression distillation, obtain 1,4 ?Er Qiang Ji ?2 ?butyleneSilicon hydrogen addition compound product; By silicon hydrogen addition compound product and annular siloxane 20～2:1 and total reactant in molar ratio0.5～1% acid catalyst of quality reacts 48～72h under 40～60 DEG C of conditions; Reacted mixture warpDeionized water wash-out catalyst, distill out unreacted completely after annular siloxane, obtain the poly-silica of terminal hydroxy groupAlkane polyalcohol.
Described platinum metal catalyst is aqueous isopropanol or the silene complexing platinum catalyst of chloroplatinic acid.
The structural formula of described annular siloxane is:
R in formula1With R2For CH3、CH2CH3Or CH2CH2CH3；m＝3～6。
Described acid catalyst is sulfuric acid or trifluoroacetic acid.
Described hydroxy-terminated polysiloxane polyalcohol, its structural formula is as follows:
R in formula1And R2Be respectively CH3、CH2CH3And/or CH2CH2CH3; N is 1～1000 integer.
Its beneficial effect is: compare with existing polysiloxane polyhydric alcohol, due to the poly-silica of terminal hydroxy group of the present inventionThe raw material of alkane polyalcohol are easy to get, and building-up process is simple, so cost is lower, have very high practical value;Meanwhile, hydroxyl is positioned in siloxane chain, when in the materials such as access polyurethane, polyester, siloxanes easily toSurface migration, makes material have good surface property, can improve the mechanical performance of polysiloxanes, and notUnder the prerequisite of the reduction mechanical property of materials, significantly reduce material surface energy, improve material resistance to water, be especially suitable forSynthetic water-base polyurethane material.
Detailed description of the invention
Embodiment 1. In 500mL there-necked flask, add 47.8g1,4 ?Er Qiang Ji ?2 ?butylene, then add 87.8gPentamethyl disiloxane, adds the chloroplatinic acid isobutanol solution 0.8mL of 3mg/ml while being warming up to 75 DEG C, continueBe warmed up to 100 DEG C of reaction 5h. Remove unreacted pentamethyl disiloxane through decompression distillation, obtain castor oilHydrosilation product 126.6g.
By above-mentioned 126.6g hydrosilation product and 460g octamethylcy-clotetrasiloxane (D4) add one dryBe furnished with in the 1000mL there-necked flask of thermometer, condenser pipe and agitating device, then add the 3.05g concentrated sulfuric acid,At 45 DEG C of reaction 48h; By deionized water, product is washed, decompression distillation obtains the poly-silicon of 563g terminal hydroxy groupOxygen alkane polyalcohol.
Embodiment 2. In 500mL there-necked flask, add 47.8g1,4 ?Er Qiang Ji ?2 ?butylene, then add 87.8gPentamethyl disiloxane, adds the chloroplatinic acid isobutanol solution 0.8mL of 3mg/ml while being warming up to 75 DEG C, continueBe warmed up to 100 DEG C of reaction 5h. Remove unreacted pentamethyl disiloxane through decompression distillation, obtain castor oilHydrosilation product 126.6g.
By above-mentioned 126.6g hydrogenated products and 1000g octamethylcy-clotetrasiloxane (D4) add dry joiningHave in the 2000mL there-necked flask of thermometer, condenser pipe and agitating device, then add the 5.4g concentrated sulfuric acid,45 DEG C of reaction 60h; By deionized water, product is washed, decompression distillation obtains the poly-silica of 963g terminal hydroxy groupAlkane polyalcohol.
Embodiment 3. In 500mL there-necked flask, add 47.8g1,4 ?Er Qiang Ji ?2 ?butylene, then add 87.8gPentamethyl disiloxane, adds silene complexing platinum catalyst 0.8mL to continue to be warmed up to 100 DEG C while being warming up to 80 DEG CReaction 5h. Remove unreacted pentamethyl disiloxane through decompression distillation, obtain 1,4 ?Er Qiang Ji ?2 ?butylene siliconHydrogenated products 126.6g.
By above-mentioned 126.6g hydrosilation product and 1700g octamethylcy-clotetrasiloxane (D4) add one dryBe furnished with in the 3000mL there-necked flask of thermometer, condenser pipe and agitating device, then add 10.1g trifluoroacetic acid,At 45 DEG C of reaction 72h; By deionized water, product is washed, it is poly-that decompression distillation obtains 1657g terminal hydroxy groupSiloxane polyol.
Above-described embodiment 1 ?3 its structural formulas of hydroxy-terminated polysiloxane polyalcohol of preparing be:
R in formula1And R2Be respectively CH3、CH2CH3And/or CH2CH2CH3; N is 1～1000 integer.
Claims (5)
1. a preparation method for hydroxy-terminated polysiloxane polyalcohol, is characterized in that: first by pentamethyl two siliconOxygen alkane and Isosorbide-5-Nitrae-dihydroxy-2-butylene in molar ratio 1:1.2～1 adds in reactor, presses every in the time of 70～80 DEG CGram reactant quality adds the platinum metal catalyst of 10～35 μ g, and reacts 4～8 under 80～120 DEG C of conditionsH; Unreacted pentamethyl disiloxane is removed in decompression distillation, obtains the silicon hydrogen addition of Isosorbide-5-Nitrae-dihydroxy-2-butyleneProduct; By silicon hydrogen addition compound product and annular siloxane in molar ratio 20～2:1 and total reactant quality 0.5～1% acid catalyst reacts 48～72h under 40～60 DEG C of conditions; Reacted mixture is washed through deionizationDenitrating catalyst, distill out unreacted completely after annular siloxane, obtain hydroxy-terminated polysiloxane polyalcohol.
2. the preparation method of a kind of hydroxy-terminated polysiloxane polyalcohol according to claim 1, its featureBe: the isopropyl alcohol alcoholic solution that described platinum metal catalyst is chloroplatinic acid or silene complexing platinum catalyst.
3. the preparation method of a kind of hydroxy-terminated polysiloxane polyalcohol according to claim 1, its featureBe: the structural formula of described annular siloxane is:
R in formula1With R2For CH3、CH2CH3Or CH2CH2CH3；m＝3～6。
4. the preparation method of a kind of hydroxy-terminated polysiloxane polyalcohol according to claim 1, its featureBe: described acid catalyst is sulfuric acid or trifluoroacetic acid.
5. the preparation method of a kind of hydroxy-terminated polysiloxane polyalcohol according to claim 1, its featureBe: the structural formula of described hydroxy-terminated polysiloxane polyalcohol is:
R in formula1And R2Be respectively CH3、CH2CH3And/or CH2CH2CH3; N is 1～1000 integer.
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| CN110606926A (en) * | 2019-10-12 | 2019-12-24 | 成都硅宝科技股份有限公司 | Auxiliary agent for enhancing water resistance of polyurethane and preparation method thereof |
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| CN107652434A (en) * | 2017-10-16 | 2018-02-02 | 德清舒华泡沫座椅有限公司 | A kind of preparation method of organosilicon polyalcohol |
| CN113321571B (en) * | 2021-06-21 | 2023-05-26 | 万华化学集团股份有限公司 | Synthesis method of linear dihydric alcohol |
| CN115678477B (en) * | 2021-07-29 | 2024-05-03 | 万华化学（北京）有限公司 | Double-component solvent-free polyurethane laminating adhesive and preparation method thereof |
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|---|---|---|---|---|
| CN1044100A (en) * | 1990-03-02 | 1990-07-25 | 化工部晨光化工研究院二分厂 | The method for making of α ω siloxane glycol |
| CN101381462A (en) * | 2008-09-10 | 2009-03-11 | 中国科学技术大学 | Polysiloxane binary alcohol with polyether block and preparation method thereof |
| CN101775141A (en) * | 2010-02-25 | 2010-07-14 | 合肥市科天化工有限公司 | Method for preparing castor oil-based polysiloxane polyol |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1044100A (en) * | 1990-03-02 | 1990-07-25 | 化工部晨光化工研究院二分厂 | The method for making of α ω siloxane glycol |
| CN101381462A (en) * | 2008-09-10 | 2009-03-11 | 中国科学技术大学 | Polysiloxane binary alcohol with polyether block and preparation method thereof |
| CN101775141A (en) * | 2010-02-25 | 2010-07-14 | 合肥市科天化工有限公司 | Method for preparing castor oil-based polysiloxane polyol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110606926A (en) * | 2019-10-12 | 2019-12-24 | 成都硅宝科技股份有限公司 | Auxiliary agent for enhancing water resistance of polyurethane and preparation method thereof |
| CN110606926B (en) * | 2019-10-12 | 2022-02-22 | 成都硅宝科技股份有限公司 | Auxiliary agent for enhancing water resistance of polyurethane and preparation method thereof |
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