CN115322360B - Preparation method and application of unit alcohol polymer block polyether - Google Patents
Preparation method and application of unit alcohol polymer block polyether Download PDFInfo
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- CN115322360B CN115322360B CN202211116710.1A CN202211116710A CN115322360B CN 115322360 B CN115322360 B CN 115322360B CN 202211116710 A CN202211116710 A CN 202211116710A CN 115322360 B CN115322360 B CN 115322360B
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- polymer block
- block polyether
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- heating
- unit alcohol
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 53
- 229920000570 polyether Polymers 0.000 title claims abstract description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- 238000003756 stirring Methods 0.000 claims abstract description 35
- 239000000575 pesticide Substances 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 230000032683 aging Effects 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000003995 emulsifying agent Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- -1 [ tri (dimethylamino) phosphoranylideneamino ] phosphorus chloride Chemical compound 0.000 claims description 5
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007664 blowing Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000010926 purge Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002981 blocking agent Substances 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract description 15
- 238000009826 distribution Methods 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 239000000839 emulsion Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000001804 emulsifying effect Effects 0.000 abstract description 2
- 238000005338 heat storage Methods 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 4
- 229940051841 polyoxyethylene ether Drugs 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- IWOUTIHKEQOMCY-UHFFFAOYSA-N 2-ethyl-3,4,5-triphenylphenol Chemical compound C1(=CC=CC=C1)C=1C(=C(C(=C(C1)O)CC)C1=CC=CC=C1)C1=CC=CC=C1 IWOUTIHKEQOMCY-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 239000005502 Cyhalofop-butyl Substances 0.000 description 2
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- ULXGUAKVZXIYJM-UHFFFAOYSA-N CN(C)P(=NP(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)F)(N(C)C)N(C)C Chemical group CN(C)P(=NP(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)F)(N(C)C)N(C)C ULXGUAKVZXIYJM-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical group [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2696—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the process or apparatus used
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Polyethers (AREA)
Abstract
The invention relates to the field of polymers, in particular to a preparation method and application of a unit alcohol polymer block polyether, wherein the reaction temperature, the reaction air pressure and the reaction stirring rate of the prepared unit alcohol polymer block polyether are strictly limited in the synthesis process, so that the molecular weight of the prepared product is 1800-2500, the molecular weight distribution is less than 1.1, the property is stable, the unit alcohol polymer block polyether can be well applied to the compound use of pesticide emulsifiable concentrate, the stability of the emulsifiable concentrate is enhanced, the cold and heat storage resistance of the emulsifiable concentrate is greatly improved, the service time of the emulsifiable concentrate is prolonged, the emulsion difficulty of the emulsifiable concentrate is reduced, and the phenomenon that the stability and the orientation of the pesticide emulsion are poor is improved; the prepared unit alcohol polymer block polyether has excellent performance, strong emulsifying performance and stable property on pesticide emulsifiable concentrate, and has wide application prospect in the related pesticide production field.
Description
Technical Field
The invention relates to the technical field of polymers, in particular to a preparation method and application of a unit alcohol polymer block polyether.
Background
When the high-content emulsifiable concentrate preparation is prepared, the high-content emulsifiable concentrate product has very difficult guarantee of common stability of emulsification and cold and hot storage due to higher solid content. The addition of the amphiphilic unit alcohol polymer block polyether can obviously improve the emulsion stability of the preparation, so that the use amount of an emulsifier is reduced, the addition amount of a cosolvent is increased, and finally, the purpose that the emulsion stability and the cold and hot storage stability reach the standard together is realized.
The conventional unit alcohol block polyether is synthesized by using potassium hydroxide as a catalyst, the relative molecular weight of the product is generally between 500 and 1500, the molecular weight distribution is more than 1.3Mw.Mn -1, and the free polyethylene glycol and polypropylene glycol are more than 3 percent. The lower molecular weight is difficult to have a better steric hindrance structure, the excessively wide molecular weight distribution shows that the product quality is difficult to stabilize, and the existence of excessive free polyethylene glycol and polypropylene glycol reduces the content of the true effective composition of the product, so that the search of a good catalyst for preparing the unit alcohol block polyether with narrow molecular weight distribution is of practical application significance.
Disclosure of Invention
The invention aims to provide a hyaluronic acid-based wound hemostasis repair gel and a preparation method thereof, which are used for solving the problems in the background technology.
In order to solve the technical problems, the invention provides the following technical scheme: a monol polymer block polyether having the following characteristics: the unit alcohol polymer block polyether is prepared by synthesizing low-carbon unit alcohol, ethylene oxide, propylene oxide and an alkyl end capping agent under the catalysis of a reaction catalyst and an end capping catalyst.
Further, the low-carbon number unit alcohol is any one or more of monohydric straight-chain or branched-chain alcohol containing 4-8 carbon atoms; the alkyl end capping agent is one or more of methyl chloride, chlorooctane and chloromonth silane.
The low-carbon unit alcohol is mainly used as an initiator to participate in the synthesis of products, and the effect of the low-carbon unit alcohol is to provide free radicals in the reaction, so that the synthesis reaction can be initiated.
Wherein the alkyl end-capping agent is preferably chlor-lunar silane, and the alkyl end-capping agent has the function of performing end-capping operation on the high polymer block polyether, so that the product performance of the high polymer block polyether is changed to a direction with better fluidity and better wetting permeability
Further, the reaction catalyst is any one or more of phosphonitrile trichloride, polydiphenoxy phosphonitrile, tetra [ tri (dimethylamino) phosphoranylideneamino ] phosphorus chloride and tetra [ tri (dimethylamino) phosphoranylideneamino ] phosphorus fluoride; the end-capping catalyst is any one or more of sodium hydroxide, potassium methoxide and sodium methoxide.
Wherein the reaction catalyst is preferably tetrakis [ tris (dimethylamino) phosphoranylideneamino ] phosphorus fluoride.
Wherein the end-capping catalyst is preferably sodium methoxide; when the end-capped catalyst is used for synthesizing a product, the synthesis reaction rate can be accelerated, the smooth progress of the synthesis reaction is ensured, meanwhile, the molecular weight distribution of the product of the synthesis reaction is narrowed, and the whole structure of the product is more regular; so that more propylene oxide and ethylene oxide can be smoothly added to form a high polymer product.
A preparation method of a monoalcohol polymer block polyether comprises the following steps:
S1, mixing unit alcohol with a reaction catalyst, heating to 120-140 ℃, vacuumizing, introducing nitrogen, and purging for 45-60min to remove redundant water;
S2, maintaining the reaction air pressure at 0.2-0.3MPa, uniformly mixing, heating to 135-145 ℃, controlling the reaction air pressure at 0.15-0.2MPa, introducing propylene oxide, stirring and reacting for about 3-5h until the propylene oxide is introduced, aging and reacting for 1-2h, detecting the reaction air pressure at any time, and vacuumizing and reacting for 30-45min after the reaction air pressure is reduced to 0.08-0.12 MPa;
In the process, propylene oxide and unit alcohol are subjected to addition reaction under the action of a reaction catalyst, and the molecular weight of a reactant is continuously increased through chain growth reaction to form linear unit alcohol polyoxypropylene ether; during synthesis, pressure and temperature control are key to ensure that the chain growth reaction can be smoothly carried out, too low a temperature can lead the reaction to be slow and be unfavorable for continuous carrying out of the chain growth reaction, and too high a temperature can lead reactants to more easily reach the reaction activation energy of chain transfer, so that more byproducts are produced; the control of the stirring speed is a key for ensuring that propylene oxide can be smoothly added, the too slow stirring speed can lead to the too high viscosity of the product and the widened molecular weight distribution, and the too fast stirring speed can lead to the too low viscosity of the product and the increase of small molecular products, so the reaction temperature, the reaction air pressure and the stirring speed in the step S2 are strictly limited to ensure the purity of the synthesized product;
After the propylene oxide is introduced, an aging step is added, the reaction product of the first step is subjected to stabilizing and refining treatment, the aging is used for enabling the molecular weight distribution of the reactant to be narrower, and the vacuumizing is used for removing unreacted micromolecular components, so that possible interference matters in the subsequent reaction are reduced as much as possible.
S3, heating to 135-145 ℃, controlling the reaction air pressure to 0.15-0.2MPa, introducing ethylene oxide, stirring and reacting for about 2-4 hours until the ethylene oxide is introduced, aging for 2-3 hours, detecting the reaction air pressure, and vacuumizing for 30-45 minutes after the reaction air pressure is reduced to 0.08-0.12 MPa;
ethylene oxide continues to undergo a chain extension reaction with the reaction product of step S2, thereby forming a regular block polyether structure; and because the molecular weight of the ethylene oxide is low, the addition reaction is relatively easy to carry out, so the stirring rate is reduced on the basis of the method, and the reaction rate is slowed down.
S4, stopping heating, cooling the reaction product to room temperature, maintaining stirring, adding hydrogen peroxide accounting for 2% of the total mass, continuously blowing nitrogen, vacuumizing for 0.5h, and then finishing washing operation to obtain a refined uncapped low-carbon alcohol high-molecular block polyether product;
S5, mixing the refined uncapped low-carbon alcohol polymer block polyether product with a capping catalyst solution, heating to 120-125 ℃, vacuumizing, stirring for reacting for 1-2 hours, cooling to 60-70 ℃, adding an alkyl capping agent, uniformly mixing, heating to 120-125 ℃, controlling the reaction pressure to 0.3-0.4MPa, reacting for 2-3 hours, vacuumizing for 1-2 hours, and cooling to 60-70 ℃ to obtain a crude product of the monol polymer block polyether;
S6, adding deionized water and H 3PO4 into the unit alcohol polymer block polyether, heating to 85-95 ℃, stirring and reacting for 1-1.5H, heating to 105-110 ℃ when the pH is 4-7, heating and dehydrating, and filtering to obtain the unit alcohol polymer block polyether.
Further, in step S1, the mass ratio of the catalyst to the monohydric alcohol is (50-250 mg): 1Kg.
Further, the mass ratio of the unit alcohol to the propylene oxide to the ethylene oxide is 1: (7-12): (9-16).
Further, in step S2, the stirring reaction rate is 450-600rpm.
Further, in step S3, the stirring reaction rate is 350-450rpm.
Further, in the step S5, the mass ratio of the uncapped low-carbon alcohol polymer block polyether, the capping catalyst and the alkyl capping agent is 1Kg: (2.5-5 g): (0.1-0.15 Kg).
Further, the application of the monoalcohol polymer block polyether is characterized in that: the unit alcohol polymer block polyether is mixed with pesticide emulsifiable concentrate to prepare the emulsifiable concentrate preparation with stable properties.
R1OH+C24H72FN16P5→R1O-C24H72N16P5+HF
R1O-C24H72N16P5+n(CH3CH-O-CH2)→R1O(CH3CHCH2O)n-C24H72N16P5
R1O(CH3CHCH2O)n-C24H72N16P5+n(CH2-O-CH2)→R1O(CH3CHCH2O)n-(CH2CH2O)n-C24H72N16P5
R1O(CH3CHCH2O)n-(CH2CH2O)n-C24H72N16P5+HF→R1O(CH3CHCH2O)n-(CH2CH2O)n-H+C24H72FN16P5
R1O(CH3CHCH2O)n-(CH2CH2O)n-H+CH3ONa→R1O(CH3CHCH2O)n-(CH2CH2O)n-Na+CH3OH
R1O(CH3CHCH2O)n-(CH2CH2O)n-Na+R2-Cl→R1O(CH3CHCH2O)n-(CH2CH2O)n-R2+Na+Cl-
Wherein R 1 is a linear or branched alkyl chain with c=4 to 8, n=18 to 25; r 2 is a linear alkyl chain of c=8 or 12.
Compared with the prior art, the invention has the following beneficial effects: the preparation method has the advantages that the reaction temperature, the reaction air pressure and the reaction stirring rate of the prepared unit alcohol polymer block polyether are strictly limited in the synthesis process, so that the molecular weight of the prepared product is 1800-2500, the molecular weight distribution is less than 1.1, the property is stable, the unit alcohol polymer block polyether can be well applied to the compound use of pesticide emulsifiable concentrate, the stability of the emulsifiable concentrate is enhanced, the cold and heat storage resistance of the emulsifiable concentrate is greatly improved, the service time of the emulsifiable concentrate is prolonged, the emulsion difficulty of the emulsifiable concentrate is reduced, and the phenomenon of poor stability of the pesticide emulsion is improved.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1.
A preparation method of a monoalcohol polymer block polyether comprises the following steps:
S1, mixing 53g of unitary alcohol isobutanol with 2.65mg of phosphazene oxide catalyst, heating to 120 ℃, vacuumizing, introducing nitrogen, and purging for 45min to remove redundant water;
S2, maintaining the reaction pressure at 0.2MPa, heating and maintaining the reaction temperature at 135-145 ℃, controlling the reaction pressure at 0.15-0.2MPa, adding 471g of propylene oxide for reaction, stirring for 3 hours at the stirring speed of 450rpm until the propylene oxide is introduced, aging for 1 hour after the pressure is reduced and stabilized, detecting the reaction pressure at any time, and vacuumizing for 30 minutes after the reaction pressure is reduced to 0.12 MPa;
S3, heating to 135-145 ℃, controlling the reaction pressure to be 0.15MPa, introducing 476g of ethylene oxide for reaction, stirring for 3 hours at the stirring speed of 350rpm until the ethylene oxide is introduced, aging for 2 hours, detecting the reaction pressure, and vacuumizing for 30 minutes after the reaction pressure is reduced to 0.12 MPa;
S4, stopping heating, cooling the reaction product to room temperature, maintaining stirring, adding hydrogen peroxide accounting for 2% of the total mass, continuously blowing nitrogen, vacuumizing for 0.5h, and then finishing washing operation to obtain a refined uncapped low-carbon alcohol high-molecular block polyether product;
s5, mixing 1Kg of refined low-carbon alcohol polymer block polyether product with 4g of sodium methoxide, heating to 120 ℃, vacuumizing, stirring and reacting for 1h, cooling to 60 ℃, adding 105g of chlorlunar silane, uniformly mixing, heating to 120 ℃, controlling the reaction pressure to be 0.3MPa, reacting for 2h, vacuumizing and reacting for 1h, and cooling to 60 ℃ to obtain a crude product of the unit alcohol polymer block polyether;
S6, adding deionized water accounting for 4 weight percent and H 3PO4 with corresponding weight percent into the unit alcohol polymer block polyether, heating to 85 ℃, stirring and reacting for 1H, heating to 105 ℃ when the pH is 7, heating and dehydrating until the water content is 0.5 weight percent, and filtering to obtain the unit alcohol polymer block polyether.
Example 2.
A preparation method of a monoalcohol polymer block polyether comprises the following steps:
s1, mixing 130g of isooctanol and 32.5mg of phosphazene oxide catalyst, heating to 140 ℃, vacuumizing, introducing nitrogen, and purging for 60min to remove redundant water;
S2, maintaining the reaction air pressure at 0.2MPa, heating and maintaining the reaction temperature at 135-145 ℃, controlling the reaction air pressure at 0.15-0.2MPa, adding 406g of propylene oxide for reaction, stirring at the stirring speed of 600rpm for reaction for 4 hours until the propylene oxide is introduced, aging for 2 hours after the pressure is reduced and stabilized, detecting the reaction air pressure at any time, and vacuumizing for reaction for 45 minutes after the reaction air pressure is reduced to 0.08 MPa;
s3, heating to 135-145 ℃, controlling the reaction pressure to 0.2MPa, introducing 396g of ethylene oxide for reaction, stirring for 3 hours at the stirring speed of 450rpm until the ethylene oxide is introduced, aging for 3 hours, detecting the reaction pressure, and vacuumizing for 45 minutes after the reaction pressure is reduced to 0.12 MPa;
S4, stopping heating, cooling the reaction product to room temperature, maintaining stirring, adding hydrogen peroxide accounting for 2% of the total mass, continuously blowing nitrogen, vacuumizing for 0.5h, and then finishing washing operation to obtain a refined uncapped low-carbon alcohol high-molecular block polyether product;
S5, mixing 1Kg of refined low-carbon alcohol polymer block polyether product with 4g of sodium methoxide solution, heating to 125 ℃, vacuumizing, stirring and reacting for 2 hours, cooling to 70 ℃, adding 110g of chlor-moon silane alkyl end-capping agent, uniformly mixing, heating to 125 ℃, controlling the reaction pressure to 0.4MPa, reacting for 3 hours, vacuumizing and reacting for 2 hours, and cooling to 70 ℃ to obtain a crude product of the unit alcohol polymer block polyether;
S6, adding deionized water with the mass fraction of 6wt% and H 3PO4 with the corresponding amount into the unit alcohol polymer block polyether, heating to 95 ℃, stirring and reacting for 1.5H, heating to 110 ℃ when the pH is 4, heating and dehydrating until the water content is 0.5wt%, and filtering to obtain the unit alcohol polymer block polyether.
And (3) detection: the unit alcohol polymer block polyether prepared in the examples 1-4 of the invention is respectively mixed with 400g/L cyhalofop-butyl EC, 5% avermectin, 34% propanil and 20% phenylpropyl, and the emulsion appearance and stability and cold-hot storage stability are detected;
Wherein the stability is qualified, and the 5% avermectin grease is prepared according to national standard GB/T1603-2001, namely: in standard hard water with the temperature of 30 ℃ being 342ppm, after being diluted by 200 times, the water is qualified after no oil slick and precipitation exist within 1 hour. 30% cyhalofop-butyl and 48% chlorpyrifos are detected according to FAO standard MT 36.1.1, namely, after 20 times dilution in standard hard water at 30 ℃ of 342ppm, the ointment is less than 2ml after 0.5 hour, the ointment is less than 4ml after 24 hours, and the floating oil is less than 0.5ml; then emulsifying again, and obtaining qualified ointment after no oil slick exists for 24.5 hours;
Wherein the materials used in the detection are as follows:
the common anionic emulsifier is calcium dodecyl benzene sulfonate; the common nonionic emulsifier is any one of triphenyl ethyl phenol polyoxyethylene ether, castor oil polyoxyethylene ether and fatty alcohol polyoxyethylene ether, and the triphenyl ethyl phenol polyoxyethylene ether is used in the scheme;
The detection results are as follows:
Example 1.
Table 1.
Table 2.
Table 3.
Table 4.
Example 2.
Table 5.
Table 6.
Table 7.
Table 8.
Finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. The application of the monoalcohol polymer block polyether in the pesticide emulsifier is characterized in that: the preparation of the monoalcohol polymer block polyether comprises the following steps:
S1, mixing unit alcohol with a reaction catalyst, heating to 120-140 ℃, vacuumizing, introducing nitrogen, and purging for 45-60min to remove redundant water;
wherein the unit alcohol is any one or more of monohydric straight-chain or branched-chain alcohol containing 4-8 carbon atoms;
S2, maintaining the reaction air pressure at 0.2-0.3MPa, uniformly mixing, heating to 135-145 ℃, controlling the reaction air pressure at 0.15-0.2MPa, introducing propylene oxide, stirring for reaction for 3-5h until the introduction of the propylene oxide is finished, aging for 1-2h, detecting the reaction air pressure at any time, and vacuumizing for 30-45min after the reaction air pressure is reduced to 0.08-0.12 MPa;
S3, heating to 135-145 ℃, controlling the reaction air pressure to be 0.15-0.2MPa, introducing ethylene oxide, stirring and reacting for 2-4h until the ethylene oxide is introduced, aging for 2-3h, detecting the reaction air pressure, and vacuumizing for 30-45min after the reaction air pressure is reduced to 0.08-0.12 MPa;
s4, stopping heating, cooling the reaction product to room temperature, maintaining stirring, adding hydrogen peroxide accounting for 2% of the total mass, continuously blowing nitrogen, vacuumizing for 0.5h, and then finishing washing operation to obtain a refined uncapped low-carbon alcohol high-molecular block polyether product;
s5, mixing the refined uncapped low-carbon alcohol polymer block polyether product with a capping catalyst solution, heating to 120-125 ℃, vacuumizing, stirring for reacting for 1-2 hours, cooling to 60-70 ℃, adding an alkyl capping agent, uniformly mixing, heating to 120-125 ℃, controlling the reaction pressure to 0.3-0.4MPa, reacting for 2-3 hours, vacuumizing for 1-2 hours, and cooling to 60-70 ℃ to obtain a crude product of the monol polymer block polyether;
wherein the alkyl end-capping agent is chloro-laurane;
S6, adding deionized water and H 3PO4 into the unit alcohol polymer block polyether, heating to 85-95 ℃, stirring and reacting for 1-1.5H, heating to 105-110 ℃ when the pH is 4-7, heating and dehydrating, and filtering to obtain the unit alcohol polymer block polyether.
2. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: the reaction catalyst is any one or more of phosphonitrile trichloride, polydiphenoxy phosphonitrile, tetra [ tri (dimethylamino) phosphoranylideneamino ] phosphorus chloride and tetra [ tri (dimethylamino) phosphoranylideneamino ] phosphorus fluoride; the end-capping catalyst is any one or more of sodium hydroxide, potassium methoxide and sodium methoxide.
3. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: in step S1, the mass ratio of the catalyst to the unit alcohol is (50-250 mg): 1Kg.
4. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: the mass ratio of the unit alcohol to the epoxypropane to the epoxyethane is 1: (7-12): (9-16).
5. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: in step S2, the stirring speed is 450-600rpm.
6. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: in step S3, the stirring speed is 350-450rpm.
7. The use of a monoalcohol polymer block polyether in a pesticide emulsifier according to claim 1, wherein: in the step S5, the mass ratio of the unblocked low-carbon alcohol polymer block polyether to the blocking catalyst to the alkyl blocking agent is 1Kg: (2.5-5 g): (0.1-0.15 Kg).
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