CN110041199A - A kind of monomer containing o-phthalaldehyde, by the polymer and preparation method and application of monomer preparation - Google Patents
A kind of monomer containing o-phthalaldehyde, by the polymer and preparation method and application of monomer preparation Download PDFInfo
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- CN110041199A CN110041199A CN201910064411.XA CN201910064411A CN110041199A CN 110041199 A CN110041199 A CN 110041199A CN 201910064411 A CN201910064411 A CN 201910064411A CN 110041199 A CN110041199 A CN 110041199A
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- polymer
- monomer
- phthalaldehyde
- reaction
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- 229920000642 polymer Polymers 0.000 title claims abstract description 91
- 239000000178 monomer Substances 0.000 title claims abstract description 69
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229940054441 o-phthalaldehyde Drugs 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 11
- -1 hydroxyl ethyl Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000007870 radical polymerization initiator Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 16
- 102000004169 proteins and genes Human genes 0.000 abstract description 13
- 108090000623 proteins and genes Proteins 0.000 abstract description 13
- 230000005847 immunogenicity Effects 0.000 abstract description 5
- 230000009467 reduction Effects 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000021615 conjugation Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 9
- 229940098773 bovine serum albumin Drugs 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- DYNFCHNNOHNJFG-UHFFFAOYSA-M 2-formylbenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-M 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003141 primary amines Chemical group 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- YEKKYNMBVXLDCB-UHFFFAOYSA-N acetic acid;nitrobenzene Chemical compound CC(O)=O.[O-][N+](=O)C1=CC=CC=C1 YEKKYNMBVXLDCB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- 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
- A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a kind of monomer containing o-phthalaldehyde, by the polymer and preparation method and application of monomer preparation.The wherein monomer of the o-phthalaldehyde, shown in structure such as formula (I).Contain o-phthalaldehyde in monomer structure of the present invention, suitable for preparing polymer antibacterial agent；Polymer prepared therefrom is while with fine antibacterial activity, in use, does not need can be discharged into environment, there is no content reduction, the case where antibacterial action declines, while the problem of residual toxicity is also not present；It can be conjugated simultaneously with efficient, while not influence the immunogenicity of protein also；Furthermore the polymer can choose lipophilic or hydrophilic monomer and polymerize, so as to which different deliquescent polymer are prepared according to demand, convenient for application during preparation.
Description
Technical field
The present invention relates to filed of functional, more particularly, to a kind of monomer containing o-phthalaldehyde, by monomer
The polymer and preparation method and application of preparation.
Background technique
O-phthalaldehyde is the dialdehyde of the adjacent fragrant aldehyde radical with there are two, is a kind of antibacterial agent efficiently, safe, to thin
Bacterium, fungi, virus or even certain helminths have very strong killing effect, have been developed into a kind of novel efficient
Antibacterial agent has simultaneously passed through U.S. FDA certification.
Low molecule organic antibacterial agent belongs to release type antibacterial agent, by being supported on suitable carrier, can be discharged into environment
Bacterium is acted on, to play antibacterial action.The content that this mode will lead to active constituent constantly declines, anti-microbial property
It just constantly reduces therewith, until disappearing, it is therefore desirable to which strict control rate of release is extended the expiration date；Exist simultaneously remaining poison
The problem of property, human health and Environmental security may be jeopardized.And for low relative molecular organic antibacterial agent, polymer antibacterial agent
Have many advantages, such as that performance is stable, non-volatile, safety and effectivity, therefore becomes the emphasis of the area research in recent years.
Therefore, it is directly used compared to o-phthalaldehyde, O-phthalic aldehyde polymer is prepared, as polymer antibacterial agent
It uses, then can be very good to avoid the above problem.Moreover, according to the difference of selected monomer, with other polymerisations
Then available water-soluble polymer antibacterial agent；It polymerize then available oil-soluble polymers antibacterial with other oil-soluble monomers
Agent, application range are more wide.
In addition, protein-polymer conjugates by the performance diversity of the biological function of protein and polymer, conveniently
Treatability combines；After polymeric conjugation, many performances of protein such as dissolubility, stability and bioavilability etc.
It is improved, but also causes the immunogenicity of protein to substantially reduce simultaneously.If after being able to maintain protein and polymeric conjugation
Immunogenicity does not reduce, then is very beneficial for the application of protein-polymer conjugates.
But currently, the research and report about O-phthalic aldehyde polymer are less, O-phthalic aldehyde polymer also has pole
Big research and development application prospect.
Summary of the invention
It is an object of the invention to aiming at the shortcomings in the prior art and defect, provide a kind of list containing o-phthalaldehyde
Body.Contain o-phthalaldehyde in monomer structure of the present invention, suitable for preparing polymer antibacterial agent, and can according to demand,
Selection lipophilicity or hydrophilic monomer polymerization become different deliquescent polymer, are keeping original antibacterial action
Simultaneously, additionally it is possible to the shortcomings that overcoming low molecule antibacterial agent, and different deliquescent polymerizations can be prepared according to demand
Object, convenient for application.
Another object of the present invention is to provide the preparation methods of the monomer containing o-phthalaldehyde.
A further object of the present invention is to provide the polymer by the monomer preparation containing o-phthalaldehyde.
A further purpose of the present invention is to provide the preparation method of the aldehyde polymer containing O-phthalic.
A further purpose of the present invention is to provide the application of the aldehyde polymer containing O-phthalic.
Above-mentioned purpose of the invention is achieved by following scheme:
A kind of monomer containing o-phthalaldehyde, shown in structure such as formula (I):
Monomer of the present invention containing o-phthalaldehyde is methacrylate-based monomer, can be commercialized common third
Olefin(e) acid esters monomer and acrylamide monomers are copolymerized, and the polymer of the base of function containing phthalic aldehyde is prepared.
The present invention also protects the preparation method of the monomer containing o-phthalaldehyde simultaneously, and preparation process is as follows: by first
Base hydroxy-ethyl acrylate, dicyclohexylcarbodiimide and dimethylamino naphthyridine are miscible in organic solvent, then in condition of ice bath
Lower dropwise addition 4- (3,4- dicarbaldehyde)-benzenpropanoic acid, then it is warming up to room temperature reaction, current product can be obtained.
Preferably, the hydroxyethyl methacrylate, dicyclohexylcarbodiimide, dimethylamino naphthyridine and 4- (3,4- bis-
Formaldehyde)-benzenpropanoic acid molar ratio are as follows: 0.5~1.5:0.5~1.5:0.1~0.3:0.5~2；The organic solvent is tetrahydro furan
It mutters, Isosorbide-5-Nitrae-dioxane, one or more of dimethylacrylamide；The time of the reaction is 6~48h.
Preferably, the hydroxyethyl methacrylate, dicyclohexylcarbodiimide, dimethylamino naphthyridine and 4- (3,4- bis-
Formaldehyde)-benzenpropanoic acid molar ratio are as follows: 1.2:1.2:0.24:1；The organic solvent is tetrahydrofuran；The time of the reaction
For for 24 hours.
The present invention also protects a kind of polymer containing o-phthalaldehyde, and the polymer is by containing O-phthalic shown in formula (I)
The monomer and acrylic ester monomer or acrylamide monomers of aldehyde are made by free-radical polymerized.
Preferably, the acrylic ester monomer be methyl acrylate, n-butyl acrylate, methyl methacrylate or
One or more of n-BMA；The acrylamide monomers are acrylamide or N, N- dimethyl allene
Amide.
It is highly preferred that when acrylic ester monomer is butyl acrylate, resulting polymers structural formula such as formula (II) institute
Show,
It is highly preferred that when acrylamide monomers are N,N-DMAA, resulting polymers structural formula such as formula
(III) shown in,
Contain antibacterial activity group o-phthalaldehyde in polymer of the present invention, therefore there is good antibacterial activity,
And it compares and makes while with fine antibacterial activity with low molecular o-phthalaldehyde, polymer of the present invention
With, not needing can be discharged into environment in the process, there is no content reduction, the case where antibacterial action declines, while being also not present
The problem of residual toxicity.And polymer can choose lipophilic or hydrophilic monomer and gathered during preparation
It closes, so as to which different deliquescent polymer are prepared according to demand, convenient for application.
In addition, being covalently attached is one of the main method for preparing protein-polymer conjugates at present, the key of this method
It is the efficient coupling reaction relied between polymer and protein, and the primary amine groups in protein molecule (from the end N- or rely
Histidine residue) it is the most common coupling reaction site being utilized.Reacting between o-phthalaldehyde and primary amine meets biocompatibility
The ideal conditions of chemical conversion, including quick, highly selective, can be under the conditions of room temperature and low concentration of substrate neutral (or close
It is neutral) aqueous solution in carry out.It therefore, can according to actual needs, for biocompatibility, biological degradability and other objects
It is fixed to measure body by the combined polymerization of the monomer with O-phthalic aldehyde group and other function monomer for rationality matter such as intelligent response etc.
System while the polymer with o-phthalaldehyde chemistry characteristic He other specific functions, then by the reaction of o-phthalaldehyde-primary amine
It realizes the efficient conjugation of polymer and protein molecule containing o-phthalaldehyde, while not influencing the immunogenicity of protein also.
The present invention also protects the preparation method of the polymer containing o-phthalaldehyde, including following procedure: will first contain adjacent benzene two
The monomer of carboxaldehyde radicals is dissolved in acrylic ester monomer or acrylamide monomers, obtains monomer mixture solution；Then by monomer
Mixed solution is dissolved in organic solvent, adds initiator for reaction, is precipitated to which n-hexane after reaction, is added
Obtain the polymer containing o-phthalaldehyde.
Preferably, the molar ratio of the monomer of the acrylic ester monomer and the aldehyde radical containing O-phthalic is 5~20；It is described
The molar ratio 5~25 of the monomer of acrylamide monomers and the aldehyde radical containing O-phthalic
Preferably, the initiator is radical polymerization initiator；Preferably, the initiator is azodiisobutyronitrile
Or dibenzoyl peroxide；The temperature of the reaction is 60~80 DEG C, and the reaction time is 6~48h.
It is highly preferred that the temperature of the reaction is 65 DEG C, reaction time 12h.
The polymer containing o-phthalaldehyde as antibacterial agent application also within protection scope of the present invention.
Preferably, the polymer containing o-phthalaldehyde is in coating, plastic applications as the application of antibacterial agent.
The polymer containing o-phthalaldehyde is used to prepare the application of protein-polymer conjugates also of the invention
Within protection scope.
Compared with prior art, the invention has the following advantages:
(1) contain o-phthalaldehyde in monomer structure of the present invention, suitable for preparing polymer antibacterial agent, and can be with
According to demand, selection lipophilicity or hydrophilic monomer polymerization become different deliquescent polymer, are keeping original anti-
While bacterium acts on, additionally it is possible to the shortcomings that overcoming low molecule antibacterial agent, and different dissolubilities can be prepared according to demand
Polymer, convenient for application.
(2) contain antibacterial activity group o-phthalaldehyde in polymer of the present invention, there is good antibacterial activity,
And it compares and makes while with fine antibacterial activity with low molecular o-phthalaldehyde, polymer of the present invention
With, not needing can be discharged into environment in the process, there is no content reduction, the case where antibacterial action declines, while being also not present
The problem of residual toxicity.And polymer can choose lipophilic or hydrophilic monomer and gathered during preparation
It closes, so as to which different deliquescent polymer are prepared according to demand, convenient for application.
(3) polymer of the present invention containing o-phthalaldehyde meets biocompatible chemical with reacting between primary amine and turns
The ideal conditions of change, including it is quick, highly selective, it can be under the conditions of room temperature and low concentration of substrate in neutral (or close neutrality)
Aqueous solution in carry out；Meanwhile it being efficiently conjugated with protein, while not influencing the immunogenicity of protein also.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of the monomer of aldehyde radical containing O-phthalic prepared by embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of the based polyalcohol containing o-phthalaldehyde prepared by embodiment 2.
Fig. 3 is the nucleus magnetic hydrogen spectrum figure of the based polyalcohol containing o-phthalaldehyde prepared by embodiment 3.
Fig. 4 is the gel permeation chromatogram of the polymer of the preparation of embodiment 3, bovine serum albumin and conjugation product, and blue is
Conjugation product, red are bovine serum albumin, and black is polymer.
Fig. 5 is bovine serum albumin and polymer-protein conjugate catalysis acetic acid -4- nitrobenzene prepared by embodiment 4
The ultra-violet absorption spectrum of product when ester hydrolysis.
Specific embodiment
The present invention is made combined with specific embodiments below and further being elaborated, the embodiment is served only for explaining this
Invention, is not intended to limit the scope of the present invention.Test method as used in the following examples unless otherwise specified, is
Conventional method；Used material, reagent etc., unless otherwise specified, for the reagent and material commercially obtained.
The synthesis of 1 monomer of aldehyde radical containing O-phthalic of embodiment
By 15.6g (0.12mol) hydroxyethyl methacrylate, 24.4g (0.12mol) dicyclohexylcarbodiimide (DCC)
It is dissolved in 100mLTHF with 2.9g (0.24mol) dimethylamino naphthyridine (DMAP), 20g (0.1mol) 4- will be contained under ice bath
The 100mL tetrahydrofuran solution of (3,4- dicarbaldehyde)-benzenpropanoic acid is slowly dropped into, and rear normal-temperature reaction is added dropwise for 24 hours.Wait react
After, it filters and removes precipitating, be spin-dried for solvent；Gained crude product ethyl acetate/petroleum ether (volume ratio=3:2) mobile phase
Column chromatography for separation is carried out, light red product liquid 20g is obtained.
Product is subjected to nucleus magnetic hydrogen spectrum characterization, spectrogram is shown in Fig. 1, can prove that the monomer of aldehyde radical containing O-phthalic has synthesized.
The synthesis and application of 2 oil-soluble based polyalcohol containing o-phthalaldehyde of embodiment
(1) synthesis of polymer
It is prepared jointly using monomer prepared by embodiment 1 as raw material and n-BMA monomer, it is different with azo two
Butyronitrile is initiator, according to the proportion in table 1, first will contain O-phthalic aldehyde radical monomer and n-BMA is miscible, and
It is dissolved in dioxane or tetrahydrofuran solvent, every 1g monomer is dissolved in 1mL solvent；Then two isobutyl of initiator azo is added
Nitrile reacts 12h with 65 DEG C after mixing, to after reaction, with n-hexane precipitation polymers product, oil-soluble can be obtained and contain
O-phthalaldehyde based polyalcohol.
1 raw material dosage ratio of table
According to the proportion in table 1, it is prepared for polymer 1 and polymer 2,2 kinds of polymer carry out nucleus magnetic hydrogen spectrum characterization, figure
Spectrum as shown in Figure 2, shows subject polymer to synthesize.
The molecular weight distribution situation of 2 kinds of polymer is shown in Table 2.
The molecular weight and molecular weight distribution of 22 kinds of polymer of table
| Number-average molecular weight | Weight average molecular weight | Molecular weight distribution | |
| Polymer 1 | 18300 | 23900 | 1.31 |
| Polymer 2 | 16500 | 22300 | 1.35 |
The anti-microbial property test of (2) 2 kinds of polymer
Using rubbing method, film is made in resulting polymers, later according to GB/T 21866-2008 the method, is resisted
The test of bacterium property, test result are as shown in table 3.
The antibiotic property test result of 32 kinds of polymer of table
Wherein negative control template A is the face diameter of what not laissez-faire test plate (panel) is 50x50mm in the sterilizes culture dish of 90mm
The blank of product size；Blank template B is the coating test plate (panel) for not adding antibacterial polymer film.Add as shown in Table 3, the present embodiment preparation
2 in polymer there is good fungistatic effect for Escherichia coli and staphylococcus aureus, bacteriostasis rate is up to 99%, table
Face resulting polymers have good antibacterial effect.
The synthesis and application of the water-soluble based polyalcohol containing o-phthalaldehyde of embodiment 3
(1) synthesis of polymer
Referring to the method in embodiment 2, n-BMA monomer is replaced with into N,N-DMAA list
Body is prepared according to the list of ingredients in table 4, obtains water-soluble based polyalcohol containing o-phthalaldehyde.
4 raw material dosage ratio of table
| The monomer of aldehyde radical containing O-phthalic | N, N- dimethylacrylamide | Azodiisobutyronitrile | |
| Copolymer 3 | 3.0g(0.011mol) | 27g(0.272mol) | 0.465g(0.00283mol) |
| Copolymer 4 | 6.0g(0.022mol) | 24g(0.242mol) | 0.434g(0.00264mol) |
According to the proportion in table 4, it is prepared for polymer 3 and polymer 4,2 kinds of polymer carry out nucleus magnetic hydrogen spectrum characterization, spectrum
Figure is shown in Fig. 3, can prove that subject polymer has synthesized.
The molecular weight distribution situation of 2 kinds of polymer is shown in Table 5.
The molecular weight and molecular weight distribution of 52 kinds of polymer of table
| Number-average molecular weight | Weight average molecular weight | Molecular weight distribution | |
| Copolymer 3 | 15800 | 21500 | 1.36 |
| Copolymer 4 | 14900 | 19800 | 1.33 |
The anti-microbial property test of (2) 2 kinds of polymer
Antibiotic property test is carried out referring to the method in embodiment 2, test result is as shown in table 6.
The antibiotic property test result of 62 kinds of polymer of table
As shown in Table 6, polymer has very Escherichia coli and staphylococcus aureus in manufactured in the present embodiment 2
Good fungistatic effect, bacteriostasis rate are up to 99%, and surface resulting polymers have good antibacterial effect.
The conjugate of embodiment 4 based polyalcohol containing o-phthalaldehyde and protein
12mg bovine serum albumin is dissolved in 2mL phosphate buffered saline solution (PBS), 12mg copolymer 3, room temperature are added
Lower stirring conjugation reaction 40 minutes.By reaction solution row gel permeation chromatography test, and use copolymer 3, bovine serum albumin as join
Than.As shown in figure 4, the molecular weight of conjugation product is compared with bovine serum albumin compared with polymer and is increased, it was demonstrated that bovine serum albumin with
Polymer is successfully conjugated.
For detection conjugation after protein activity, using document (Journal of Materials Chemistry,
2011,21,10390-10398) the method is characterized.Pass through analysis bovine serum albumin and the front and back catalysis of the conjugation of copolymer 3
When acetic acid -4- nitrobenzene ester hydrolysis product ultra-violet absorption spectrum (Fig. 5) it is found that conjugation after bovine serum albumin activity compared with
5% is only reduced before conjugation, it was demonstrated that conjugation is on protein active substantially without influence.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than protects to the present invention
The limitation of shield range can also be made on the basis of above description and thinking for those of ordinary skill in the art
Other various forms of variations or variation, there is no necessity and possibility to exhaust all the enbodiments.It is all of the invention
Made any modifications, equivalent replacements, and improvements etc., should be included in the protection of the claims in the present invention within spirit and principle
Within the scope of.
Claims (10)
1. a kind of monomer containing o-phthalaldehyde, which is characterized in that shown in its structure such as formula (I):
2. the preparation method of the monomer described in claim 1 containing o-phthalaldehyde, which is characterized in that its preparation process is as follows: will
Hydroxyethyl methacrylate, dicyclohexylcarbodiimide and dimethylamino naphthyridine are miscible in organic solvent, then in ice bath item
4- (3,4- dicarbaldehyde)-benzenpropanoic acid is added dropwise under part, then is warming up to room temperature reaction, current product can be obtained.
3. the preparation method of the monomer containing o-phthalaldehyde according to claim 2, which is characterized in that the methacrylic acid
The molar ratio of hydroxyl ethyl ester, dicyclohexylcarbodiimide, dimethylamino naphthyridine and 4- (3,4- dicarbaldehyde)-benzenpropanoic acid are as follows: 0.5~
1.5:0.5~1.5:0.1~0.3:0.5~2；The organic solvent is tetrahydrofuran, 1,4- dioxane, dimethyl allene acyl
One or more of amine；The time of the reaction is 6~48h；
Preferably, the hydroxyethyl methacrylate, dicyclohexylcarbodiimide, dimethylamino naphthyridine and 4- (3,4- diformazans
Aldehyde)-benzenpropanoic acid molar ratio are as follows: 1.2:1.2:0.24:1；The organic solvent is tetrahydrofuran；The time of the reaction is
24h。
4. a kind of polymer containing o-phthalaldehyde, which is characterized in that the polymer contains O-phthalic as described in claim 1
The monomer and acrylic ester monomer or acrylamide monomers of aldehyde are made by free-radical polymerized.
5. according to claim 4 containing the polymer of o-phthalaldehyde, which is characterized in that the acrylic ester monomer is third
One or more of e pioic acid methyl ester, n-butyl acrylate, methyl methacrylate or n-BMA；The propylene
Amides monomer is acrylamide or N, N- dimethylacrylamide.
6. the polymer according to claim 4 containing o-phthalaldehyde, which is characterized in that when acrylic ester monomer is third
When olefin(e) acid butyl ester, shown in resulting polymers structural formula such as formula (II),
When acrylamide monomers are N,N-DMAA, shown in resulting polymers structural formula such as formula (III),
7. the preparation method of the polymer described in claim 4 containing o-phthalaldehyde, which is characterized in that including following procedure: first
The monomer of the aldehyde radical containing O-phthalic is dissolved in acrylic ester monomer or acrylamide monomers, monomer mixture solution is obtained；
Then monomer mixture solution is dissolved in organic solvent, adds initiator for reaction, carried out to which n-hexane after reaction, is added
Precipitating, can be obtained the polymer containing o-phthalaldehyde；
Preferably, the initiator is radical polymerization initiator；It is highly preferred that the initiator is azodiisobutyronitrile or mistake
Aoxidize dibenzoyl；The organic solvent is dioxane or tetrahydrofuran；The temperature of the reaction is 60~80 DEG C, when reaction
Between be 6~48h；Preferably, the temperature of the reaction is 65 DEG C, reaction time 12h.
8. any application of the polymer containing o-phthalaldehyde as antibacterial agent of claim 4~6.
9. applying according to claim 8, which is characterized in that the polymer containing o-phthalaldehyde is in coating, plastic collar
As the application of antibacterial agent in domain.
10. any polymer containing o-phthalaldehyde of claim 4~6 is used to prepare protein-polymer conjugates
Using.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5849759A (en) * | 1981-09-21 | 1983-03-24 | Daiichi Seimo Kk | Coating agent for net or rope for cultivation of alga |
| CN102100236A (en) * | 2009-12-16 | 2011-06-22 | 青岛康地恩药业有限公司 | Efficient compound disinfectant and preparation method thereof |
| CN102272244A (en) * | 2008-12-01 | 2011-12-07 | 贝克顿·迪金森公司 | Antimicrobial solvent coating compositions |
| EP1738646B1 (en) * | 2005-06-29 | 2013-03-20 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| CN106614579A (en) * | 2016-10-12 | 2017-05-10 | 南京金甙尔生物技术有限公司 | Disinfectant and application thereof |
-
2019
- 2019-01-23 CN CN201910064411.XA patent/CN110041199B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5849759A (en) * | 1981-09-21 | 1983-03-24 | Daiichi Seimo Kk | Coating agent for net or rope for cultivation of alga |
| EP1738646B1 (en) * | 2005-06-29 | 2013-03-20 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| CN102272244A (en) * | 2008-12-01 | 2011-12-07 | 贝克顿·迪金森公司 | Antimicrobial solvent coating compositions |
| CN102100236A (en) * | 2009-12-16 | 2011-06-22 | 青岛康地恩药业有限公司 | Efficient compound disinfectant and preparation method thereof |
| CN106614579A (en) * | 2016-10-12 | 2017-05-10 | 南京金甙尔生物技术有限公司 | Disinfectant and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| ESRA, BOZKR, NUREN, ET AL.: "Polystyrene Containing Carbinolamine/Azomethine Potentially Useful as Antimicrobial Agent: Synthesis and Biological Evaluation", 《JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS》 * |
| 黄建兵等: "含醛基可降解嵌段共聚物的合成及其生物缀合", 《高分子学报》 * |
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