CN105017450B - Polyvinyl ether synthesis method - Google Patents
Polyvinyl ether synthesis method Download PDFInfo
- Publication number
- CN105017450B CN105017450B CN201510487474.8A CN201510487474A CN105017450B CN 105017450 B CN105017450 B CN 105017450B CN 201510487474 A CN201510487474 A CN 201510487474A CN 105017450 B CN105017450 B CN 105017450B
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- CN
- China
- Prior art keywords
- alcohol
- polyvinyl alcohol
- phase transfer
- transfer catalyst
- carried out
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- 229920001289 polyvinyl ether Polymers 0.000 title claims abstract description 5
- 238000001308 synthesis method Methods 0.000 title abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 16
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000012044 organic layer Substances 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 239000004698 Polyethylene Substances 0.000 claims description 7
- -1 polyethylene Polymers 0.000 claims description 7
- 229920000573 polyethylene Polymers 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 claims description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 239000008236 heating water Substances 0.000 claims 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims 1
- 230000002860 competitive effect Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 4
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- LPHLNZHFRMZONI-UHFFFAOYSA-N methyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[NH2+]C LPHLNZHFRMZONI-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a polyvinyl ether synthesis method. The method comprises the steps that polyvinyl alcohol is dissolved in water, strong acid cation exchange resin and phase transfer catalyst are added, then, methylbenzene or paraxylene and corresponding alcohol are added, heating is carried out at the temperature of 110-140 DEG C, and backflowing and water diversion are carried out. After a reaction is finished, the system carries out cooling and filtering, organic layer saturated salt water washing is carried out, distillation is carried out, and a methylbenzene or paraxylene solution with 40-80% of polyvinyl ether is obtained. The cation exchange resin and the phase transfer catalyst can be recycled, so that waste is effectively reduced, and environmental protection is achieved. The obtained product is high in purity and has competitive advantages.
Description
Technical field
The present invention relates to a kind of method of synthesizing polyethylene ether, belong to technical field of organic synthesis.
Background technology
Polyvingl ether is mainly used in coating, adhesive, auxiliary agent, plasticizer, special may also be used for as boat of structure
Empty hydraulic oil, hydraulic transmission oil, shock absorber fluid.
Art methods, mainly adopt acetylene and alcohol that vinyl ethers are first obtained, and then pass through free radical or activity sun again
Polyvingl ether is obtained after ionic polymerization or copolymerization.The method needs to select different initiators or cation to carry out the length of Quality Initiative
Short, also extremely sensitive to temperature, technical requirements are of a relatively high, further limit the extensive application of such compound.Polyethylene
The current technology of alcohol synthesis is more ripe, and species is also more various, ample supply of commodities on the market, but to obtain inhomogeneity as raw material
The polyvingl ether of type still lacks pertinent literature and patent report.
Content of the invention
In order to overcome the deficiencies in the prior art it is contemplated that polyvinyl alcohol supply producer is more, price also relative moderate, this
Bright providing using polyvinyl alcohol is raw material, by becoming the scheme of ether mode synthesizing polyethylene base ether with dehydration of alcohols.
To achieve these goals, the present invention adopts the following technical scheme that
Polyvinyl alcohol is dissolved in the water, adds storng-acid cation exchange resin and phase transfer catalyst, subsequently add again
Enter toluene or xylol and corresponding alcohol, heat 110-140 DEG C of reflux water-dividing.After detection reaction no longer has moisture to go out, reaction
System is lowered the temperature, and obtains solid and be directly used in lower batch reaction after filtration.Organic layer saturated common salt is washed, and obtains 40-80% after distillation
The toluene of polyvinylether or xylol solution.
Further, in technique scheme, described polyvinyl alcohol, storng-acid cation exchange resin and phase transfer are urged
The mol ratio of agent is 1:1-10:0.01-0.05.
Further, in technique scheme, described polyvinyl alcohol is 1:5-100 with corresponding alcohol mol ratio.
Further, in technique scheme, described polyvinyl alcohol mean molecule quantity is 1.6 ten thousand -22 ten thousand, and alcoholysis degree is big
In 98%.
Further, in technique scheme, described storng-acid cation exchange resin is selected from: polystyrolsulfon acid
Type.
Further, in technique scheme, described alcohol is selected from methanol, ethanol, isopropanol, n-butyl alcohol, isobutanol.
Further, in technique scheme, described phase transfer catalyst is selected from benzyltriethylammoinium chloride, the tetrabutyl
Ammonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride, Dodecyl trimethyl ammonium chloride or ten
Tetraalkyl trimethyl ammonium chloride.
The beneficial effect of the invention
Present invention employs common polyvinyl alcohol on market is raw material, make use of raw material soluble in water, and product is permissible
It is effectively dissolved in toluene or xylol, by can get the polyvinyl of wide variety from different alcohol single step reactions
Ether.In methods described, the solid after filtration is cation exchange resin and phase transfer catalyst, can put into lower batch and continue profit
With effectively reducing garbage, environmental protection, the product purity obtaining is high, has competitive advantage.
Specific embodiment
Embodiment 1
The synthesis of polyvinylmethyl ethers:
In the there-necked flask equipped with reflux water-dividing device, add low viscosity polyvinyl alcohol (mean molecule quantity: 1.6 ten thousand -2
Ten thousand, 0.4 mole) and 20 milliliters of water in, be completely dissolved under stirring.Add storng-acid cation exchange resin (0.4 mole) and four
After butylammonium bromide (4 mmoles), add methanol (2.0 moles) and 180 milliliters of toluene, heat 110 DEG C of reflux water-dividings.Detection is anti-
After should no longer having moisture to go out, reaction system is lowered the temperature, and obtains solid and can be continually used for synthesizing 4-6 activity guarantor of this reaction after filtration
Hold identical activity.Organic layer saturated common salt is washed, and distillation obtains 40% toluene solution of polyvinylmethyl ethers.
Embodiment 2
The synthesis of polyvinyl ethyl ether:
In the there-necked flask equipped with reflux water-dividing device, add low viscosity polyvinyl alcohol (mean molecule quantity: 1.6 ten thousand -2
Ten thousand, 0.4 mole) and 22 milliliters of water in, be completely dissolved under stirring.Add storng-acid cation exchange resin (0.4 mole) and three
After octylmethylammonium chloride (5 mmoles), add ethanol (2.5 moles) and 180 milliliters of toluene, heat 110 DEG C of reflux water-dividings.Inspection
After measured reaction no longer has moisture to go out, reaction system is lowered the temperature, and obtains solid and can be continually used for synthesizing 3-4 work of this reaction after filtration
Property keep identical activity.Organic layer saturated common salt is washed, and distillation obtains 50% toluene solution of polyvinyl ethyl ether.
Embodiment 3
The synthesis of polyvinyl n-butyl ether:
In the there-necked flask equipped with reflux water-dividing device, viscosity polyvinyl alcohol (mean molecule quantity: 110,000-13 in addition
Ten thousand, 0.4 mole) and 30 milliliters of water in, be completely dissolved under stirring.Add storng-acid cation exchange resin (0.4 mole) and ten
After tetraalkyl trimethyl ammonium chloride (8 mmoles), add n-butyl alcohol (4.0 moles) and 220 milliliters of xylol, heat 140 DEG C
Reflux water-dividing.Detection reaction no longer have moisture to go out after, reaction system lower the temperature, obtain after filtration solid can be continually used for synthesis should
4-6 activity of reaction keeps identical activity.Organic layer saturated common salt is washed twice, and distillation obtains the 80% of polyvinyl n-butyl ether
Xylol solution.
Embodiment 4
The synthesis of polyvinyl isobutyl ether:
In the there-necked flask equipped with reflux water-dividing device, viscosity polyvinyl alcohol (mean molecule quantity: 110,000-13 in addition
Ten thousand, 0.4 mole) and 25 milliliters of water in, be completely dissolved under stirring.Add storng-acid cation exchange resin (0.4 mole) and ten
After dialkyl group trimethyl ammonium chloride (12 mmoles), add isobutanol (2.0 moles) and 220 milliliters of xylol, heat 140 DEG C
Reflux water-dividing.Detection reaction no longer have moisture to go out after, reaction system lower the temperature, obtain after filtration solid can be continually used for synthesis should
3-5 activity of reaction keeps identical activity.Organic layer saturated common salt is washed, and distillation obtains 60% couple two of polyvinyl isobutyl ether
Toluene solution.
These are only the present invention preferably specific embodiment, but protection scope of the present invention is not limited thereto, any
Those familiar with the art in the technical scope of present disclosure, technology according to the present invention scheme and its invention
Design in addition equivalent or change, all should be included within the scope of the present invention.
Claims (3)
1. a kind of method of synthesizing polyethylene ether it is characterised in that: polyvinyl alcohol is dissolved in the water, add highly acidic cation
Exchanger resin and phase transfer catalyst, subsequently add toluene or xylol and corresponding alcohol, 110-140 DEG C of backflow point of heating
Water；After detection reaction no longer has moisture to go out, reaction system is lowered the temperature, and obtains solid and be directly used in lower batch reaction after filtration；Organic
Layer saturated common salt washing, obtains toluene or the xylol solution of 40-80% polyvinylether after distillation；Described polyvinyl alcohol, strong acid
Property cation exchange resin and phase transfer catalyst mol ratio be 1:1-10:0.01-0.05；Described polyvinyl alcohol with corresponding
Alcohol mol ratio is 1:5-100；The mean molecule quantity of described polyvinyl alcohol is 1.6 ten thousand -22 ten thousand, and alcoholysis degree is more than 98%；Described alcohol choosing
From methanol, ethanol, isopropanol, n-butyl alcohol or isobutanol.
2. a kind of synthesizing polyethylene ether according to claim 1 method it is characterised in that: described highly acidic cation is handed over
Change resin to be selected from: polystyrene sulfonic acid type.
3. a kind of synthesizing polyethylene ether according to claim 1 method it is characterised in that: the choosing of described phase transfer catalyst
From benzyltriethylammoinium chloride, tetrabutyl ammonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride,
Dodecyl trimethyl ammonium chloride or tetradecyl trimethyl ammonium chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510487474.8A CN105017450B (en) | 2015-08-11 | 2015-08-11 | Polyvinyl ether synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510487474.8A CN105017450B (en) | 2015-08-11 | 2015-08-11 | Polyvinyl ether synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105017450A CN105017450A (en) | 2015-11-04 |
| CN105017450B true CN105017450B (en) | 2017-02-01 |
Family
ID=54407786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510487474.8A Active CN105017450B (en) | 2015-08-11 | 2015-08-11 | Polyvinyl ether synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105017450B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440258B (en) * | 2020-04-30 | 2021-08-03 | 中国科学院兰州化学物理研究所 | Polyvinyl ether compound and preparation method thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345624A (en) * | 1971-12-10 | 1974-01-30 | Rizhskij Med Inst | Derivative of beta-diethylamino-ethyl-ester of p-amino benzoic acid and carboxymethyl ether of polyvinyl alcohol a method of preparing same and uses therefor |
| US3984494A (en) * | 1973-12-21 | 1976-10-05 | Hoechst Aktiengesellschaft | Graft copolymers of vinyl acetate on polyethylene oxide as self-supporting capsules |
| SU802294A1 (en) * | 1977-10-10 | 1981-02-07 | Ленинградский Ордена Октябрьскойреволюции И Ордена Трудовогокрасного Знамени Технологическийинститут Им. Ленсовета | Method of isolatine cyanoethyl ether of polyvinyl alcohol |
| CN101130582A (en) * | 2007-08-07 | 2008-02-27 | 重庆拓桑生物科技有限公司 | Polyvinyl alcohol glycidyl ether crosslinking agent and synthesis method of the same |
| CN101186659A (en) * | 2007-11-12 | 2008-05-28 | 中北大学 | Method for synthesizing etherification modified polyvinyl alcohol |
| WO2011007894A1 (en) * | 2009-07-15 | 2011-01-20 | 住友化学株式会社 | Polyvinyl ether resin |
| US8008355B2 (en) * | 2002-03-11 | 2011-08-30 | Roche Madison Inc. | Endosomolytic poly(vinyl ether) polymers |
| WO2014185825A1 (en) * | 2013-05-17 | 2014-11-20 | Общество С Ограниченной Ответственностью "Научно-Производственный Центр "Амфион" | Hydrogel material based on cross-linked polyvinyl alcohol |
-
2015
- 2015-08-11 CN CN201510487474.8A patent/CN105017450B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345624A (en) * | 1971-12-10 | 1974-01-30 | Rizhskij Med Inst | Derivative of beta-diethylamino-ethyl-ester of p-amino benzoic acid and carboxymethyl ether of polyvinyl alcohol a method of preparing same and uses therefor |
| US3984494A (en) * | 1973-12-21 | 1976-10-05 | Hoechst Aktiengesellschaft | Graft copolymers of vinyl acetate on polyethylene oxide as self-supporting capsules |
| SU802294A1 (en) * | 1977-10-10 | 1981-02-07 | Ленинградский Ордена Октябрьскойреволюции И Ордена Трудовогокрасного Знамени Технологическийинститут Им. Ленсовета | Method of isolatine cyanoethyl ether of polyvinyl alcohol |
| US8008355B2 (en) * | 2002-03-11 | 2011-08-30 | Roche Madison Inc. | Endosomolytic poly(vinyl ether) polymers |
| CN101130582A (en) * | 2007-08-07 | 2008-02-27 | 重庆拓桑生物科技有限公司 | Polyvinyl alcohol glycidyl ether crosslinking agent and synthesis method of the same |
| CN101186659A (en) * | 2007-11-12 | 2008-05-28 | 中北大学 | Method for synthesizing etherification modified polyvinyl alcohol |
| WO2011007894A1 (en) * | 2009-07-15 | 2011-01-20 | 住友化学株式会社 | Polyvinyl ether resin |
| WO2014185825A1 (en) * | 2013-05-17 | 2014-11-20 | Общество С Ограниченной Ответственностью "Научно-Производственный Центр "Амфион" | Hydrogel material based on cross-linked polyvinyl alcohol |
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| CN105017450A (en) | 2015-11-04 |
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Address after: 753299 9 households, including plant 1, No. 98, Shizuishan economic and Technological Development Zone, Huinong District, Shizuishan City, Ningxia Hui Autonomous Region Patentee after: Ningxia Jinghong Technology Co.,Ltd. Address before: 753299 9 households, including plant 1, No. 98, Shizuishan economic and Technological Development Zone, Huinong District, Shizuishan City, Ningxia Hui Autonomous Region Patentee before: NINGXIA JINHONG BIO-TECH Co.,Ltd. |