CN111548526A - 季铵盐型树枝状聚硫醚改性聚合物微球 - Google Patents
季铵盐型树枝状聚硫醚改性聚合物微球 Download PDFInfo
- Publication number
- CN111548526A CN111548526A CN202010593002.1A CN202010593002A CN111548526A CN 111548526 A CN111548526 A CN 111548526A CN 202010593002 A CN202010593002 A CN 202010593002A CN 111548526 A CN111548526 A CN 111548526A
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- Prior art keywords
- polymer microsphere
- quaternary ammonium
- ammonium salt
- polythioether
- porous polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 115
- 239000004005 microsphere Substances 0.000 title claims abstract description 84
- 229920006295 polythiol Polymers 0.000 title claims abstract description 50
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 21
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 16
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims abstract description 16
- SYFZCLMMUNCHNH-UHFFFAOYSA-N 2-(prop-2-ynoxymethyl)oxirane Chemical compound C#CCOCC1CO1 SYFZCLMMUNCHNH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003899 bactericide agent Substances 0.000 claims abstract description 10
- -1 alkyl dithiol Chemical class 0.000 claims abstract description 9
- DSOJWVLXZNRKCS-UHFFFAOYSA-N octa-1,7-diyne Chemical compound C#CCCCCC#C DSOJWVLXZNRKCS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 21
- 238000005406 washing Methods 0.000 claims description 21
- 238000001035 drying Methods 0.000 claims description 19
- 238000001914 filtration Methods 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical group NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012965 benzophenone Substances 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
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- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000012634 fragment Substances 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 4
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 claims description 3
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 claims description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 3
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 claims description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 claims description 3
- UOQACRNTVQWTFF-UHFFFAOYSA-N decane-1,10-dithiol Chemical compound SCCCCCCCCCCS UOQACRNTVQWTFF-UHFFFAOYSA-N 0.000 claims description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 3
- YMCOIFVFCYKISC-UHFFFAOYSA-N ethoxy-[2-(2,4,6-trimethylbenzoyl)phenyl]phosphinic acid Chemical compound CCOP(O)(=O)c1ccccc1C(=O)c1c(C)cc(C)cc1C YMCOIFVFCYKISC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 claims description 3
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 3
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 3
- KNDRWHMOJREVPO-UHFFFAOYSA-N 2-methylbut-3-en-1-amine Chemical compound NCC(C)C=C KNDRWHMOJREVPO-UHFFFAOYSA-N 0.000 claims description 2
- JEDAVAJXFVJEJG-UHFFFAOYSA-N 2-methylhex-5-en-1-amine Chemical compound NCC(C)CCC=C JEDAVAJXFVJEJG-UHFFFAOYSA-N 0.000 claims description 2
- VWHLBDDPVAKXDL-UHFFFAOYSA-N 2-methylpent-4-en-1-amine Chemical compound NCC(C)CC=C VWHLBDDPVAKXDL-UHFFFAOYSA-N 0.000 claims description 2
- VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 claims description 2
- FICBXRYQMBKLJJ-UHFFFAOYSA-N hex-5-en-1-amine Chemical compound NCCCCC=C FICBXRYQMBKLJJ-UHFFFAOYSA-N 0.000 claims description 2
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 2
- UVBBCQLPTZEDHT-UHFFFAOYSA-N pent-4-en-1-amine Chemical compound NCCCC=C UVBBCQLPTZEDHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 abstract description 8
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- 238000010558 suspension polymerization method Methods 0.000 abstract description 2
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- 150000001345 alkine derivatives Chemical class 0.000 abstract 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 32
- 239000000022 bacteriostatic agent Substances 0.000 description 19
- 241000894006 Bacteria Species 0.000 description 14
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 241000191967 Staphylococcus aureus Species 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 230000003385 bacteriostatic effect Effects 0.000 description 6
- 239000007853 buffer solution Substances 0.000 description 6
- 238000012258 culturing Methods 0.000 description 6
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- 210000000170 cell membrane Anatomy 0.000 description 5
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- 125000000524 functional group Chemical group 0.000 description 4
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- OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl thioacetate Chemical compound CSC(C)=O OATSQCXMYKYFQO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
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- 230000008901 benefit Effects 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
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- 230000036512 infertility Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
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- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 description 1
- RKOOBZIVHDFVFF-UHFFFAOYSA-N 1-amino-3-methylbutane-1-thiol Chemical compound CC(C)CC(N)S RKOOBZIVHDFVFF-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 239000012752 auxiliary agent Substances 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/40—Impregnation
- C08J9/405—Impregnation with polymerisable compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2381/02—Polythioethers; Polythioether-ethers
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Epoxy Resins (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
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Claims (3)
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CN202010593002.1A CN111548526B (zh) | 2020-06-25 | 2020-06-25 | 季铵盐型树枝状聚硫醚改性聚合物微球 |
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CN202010593002.1A CN111548526B (zh) | 2020-06-25 | 2020-06-25 | 季铵盐型树枝状聚硫醚改性聚合物微球 |
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CN111548526A true CN111548526A (zh) | 2020-08-18 |
CN111548526B CN111548526B (zh) | 2022-04-26 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112159593A (zh) * | 2020-08-21 | 2021-01-01 | 烟台优尼泰新材料创新中心有限公司 | 环氧基多孔聚硫醚微球作为环氧结构胶增韧剂的应用 |
CN116333715A (zh) * | 2023-04-03 | 2023-06-27 | 烟台大学 | 一种高负载且交联时间可调节的稠化剂 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108395550A (zh) * | 2018-05-07 | 2018-08-14 | 常州大学 | 一种点击化学制备带有季铵盐结构的聚乙二醇抗菌水凝胶 |
CN110918014A (zh) * | 2019-12-05 | 2020-03-27 | 烟台大学 | 季铵盐型超支化聚硫醚改性的聚合物微球和制备方法 |
-
2020
- 2020-06-25 CN CN202010593002.1A patent/CN111548526B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108395550A (zh) * | 2018-05-07 | 2018-08-14 | 常州大学 | 一种点击化学制备带有季铵盐结构的聚乙二醇抗菌水凝胶 |
CN110918014A (zh) * | 2019-12-05 | 2020-03-27 | 烟台大学 | 季铵盐型超支化聚硫醚改性的聚合物微球和制备方法 |
Non-Patent Citations (1)
Title |
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ZHENG,YC ET AL.,: "Effect of the topology on the antibacterial activity of", 《JOURNAL OF POLYMER SCIENCE》 * |
Cited By (4)
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CN112159593A (zh) * | 2020-08-21 | 2021-01-01 | 烟台优尼泰新材料创新中心有限公司 | 环氧基多孔聚硫醚微球作为环氧结构胶增韧剂的应用 |
CN112159593B (zh) * | 2020-08-21 | 2022-07-22 | 烟台优尼泰新材料创新中心有限公司 | 环氧基多孔聚硫醚微球作为环氧结构胶增韧剂的应用 |
CN116333715A (zh) * | 2023-04-03 | 2023-06-27 | 烟台大学 | 一种高负载且交联时间可调节的稠化剂 |
CN116333715B (zh) * | 2023-04-03 | 2024-02-20 | 烟台大学 | 一种高负载且交联时间可调节的稠化剂 |
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