CN101677536A - 带有杀生物涂层的基底 - Google Patents
带有杀生物涂层的基底 Download PDFInfo
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- CN101677536A CN101677536A CN200880013438A CN200880013438A CN101677536A CN 101677536 A CN101677536 A CN 101677536A CN 200880013438 A CN200880013438 A CN 200880013438A CN 200880013438 A CN200880013438 A CN 200880013438A CN 101677536 A CN101677536 A CN 101677536A
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- CN
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- Prior art keywords
- alkyl
- aryl
- alkylidene
- thiazolinyl
- different
- Prior art date
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- 239000000758 substrate Substances 0.000 title claims abstract description 69
- 238000000576 coating method Methods 0.000 title claims abstract description 33
- 239000011248 coating agent Substances 0.000 title claims abstract description 32
- 230000003115 biocidal effect Effects 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 38
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 27
- -1 R 42 Chemical compound 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000003139 biocide Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011247 coating layer Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
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- 229920000642 polymer Polymers 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002202 Polyethylene glycol Substances 0.000 description 20
- 229920001223 polyethylene glycol Polymers 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229920002554 vinyl polymer Polymers 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
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- 239000004743 Polypropylene Substances 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000919 ceramic Substances 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 208000027418 Wounds and injury Diseases 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- 239000012298 atmosphere Substances 0.000 description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 3
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 230000005670 electromagnetic radiation Effects 0.000 description 3
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- 239000004744 fabric Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001684 low density polyethylene Polymers 0.000 description 3
- 239000004702 low-density polyethylene Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VFFFESPCCPXZOQ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.OCC(CO)(CO)CO VFFFESPCCPXZOQ-UHFFFAOYSA-N 0.000 description 2
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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
-
- 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
- A01N25/08—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 solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- 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
-
- 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
- A01N37/12—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, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
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Abstract
本发明提供了涂布基底表面的方法,包括下列步骤:(i)氧化基底表面,(ii)将包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物施加到基底的氧化表面上,和(iii)固化所述组合物以形成涂层,和可通过这一方法获得的基底。
Description
本发明涉及用杀生物涂层涂布基底表面的方法和可通过这一方法获得的带有杀生物表面的基底。
基底可以用杀生物剂处理以保护基底免受生物侵扰和生长。生物材料,如植物、藻类或微生物在基底表面上的不希望的积聚通常被称作生物污垢。一般防污剂是四丁基锡(TBT)或乙酸苯汞。防污剂会泄漏到环境中并因此污染环境。这些杀生物剂的泄漏会在目标生物体中造成抗性,且由于这些防污剂通常对非目标生物体,如人类和其它哺乳动物而言也是高毒性的,不能排除对这些生物体的不希望的伤害。
因此,过去已作出几种尝试以开发杀生物涂层,其中杀生物剂共价连接到基底表面上,因此不会泄漏到环境中。
DE 102 11 562A1描述了通过用具有至少一个季铵基团和至少一个能与基底形成共价键的基团(该基团优选是伯氨基或仲氨基)的抗菌聚合物或共聚物处理基底表面而制成的带有抗菌表面的基底。
US 2006/0008490A1和WO 2005/084159描述了带有杀生物表面的基底,其如下制备:在基底上固定引发剂、使带有能够转化成生物杀灭活性基团的基团的单体聚合到该固定的引发剂上,并在聚合后,将这些基团转化成生物杀灭活性基团。
DE 102 11 562A1、US 2006/0008490A1和WO 2005/084159中描述的杀生物涂层的缺点在于,不能在现有印刷设备上在大规模连续工艺中简单地制备这些杀生物涂层。
因此,本发明的目的是提供用杀生物涂层涂布基底的方法,该方法在技术上可以在现有印刷设备上以大规模和以连续模式实行,且该方法产生杀生物涂层,其中没有杀生物剂泄漏到环境中。此外,合意的是,该杀生物层表现出高耐久性,这意味着在该杀生物层暴露在各种环境条件下时,例如在该杀生物层长期暴露在水中时,杀生物涂层的生物杀灭活性不会被显著影响。
该目的通过权利要求1的方法、权利要求10的基底和权利要求11的混合物实现。
本发明的涂布基底表面的方法包括下列步骤:
(i)氧化基底表面
(ii)将包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物施加到所述基底的氧化表面上和
(iii)固化所述组合物以形成涂层。
基底可以是二维物体,如板或薄膜,或任何三维物体;其可以是透明或不透明的。基底可以由纸、纸板、木材、皮革、金属、织物、玻璃、陶瓷、石头和/或聚合物制成。
金属的实例是铁、镍、钯、铂、铜、银、金、锌和铝,以及合金,如钢、黄铜、青铜和硬铝。
织物可以由天然纤维,如来自动物或植物来源的纤维,或由合成纤维制成。来自动物来源的天然纤维的实例是羊毛和丝。来自植物来源的天然纤维的实例是棉、亚麻和黄麻。合成织物的实例是聚酯、聚丙烯酰胺、聚烯烃如聚乙烯和聚丙烯、以及聚酰胺如尼龙和莱卡(lycra)。
陶瓷的实例是主要由粘土制成的产品,例如砖、瓷砖和瓷,以及技术陶瓷。技术陶瓷可以是氧化物如氧化铝、二氧化锆、二氧化钛和钛酸钡,碳化物如碳化钠、碳化硅或碳化硼,硼化物如硼化钛,氮化物如氮化钛或氮化硼,以及硅化物如硅化钠或硅化钛。
石头的实例是石灰石、花岗岩、片麻岩、大理石、板岩和砂岩。
聚合物的实例是丙烯酸类聚合物、苯乙烯类聚合物及其氢化产物、乙烯基聚合物及其衍生物、聚烯烃及其氢化或环氧化产物、醛聚合物、环氧化物聚合物、聚酰胺、聚酯、聚氨酯、聚碳酸酯、砜基聚合物和天然聚合物及其衍生物。
丙烯酸类聚合物可以是由至少一种丙烯酸类单体或由至少一种丙烯酸类单体和至少一种其它烯键式不饱和单体,如苯乙烯类单体、乙烯基单体、烯烃单体或马来酸类单体形成的聚合物。
丙烯酸类单体的实例是(甲基)丙烯酸、(甲基)丙烯酰胺、(甲基)丙烯腈、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸缩水甘油酯、甲基丙烯酸乙酰乙酰氧乙酯、丙烯酸二甲基氨基乙酯和丙烯酸二乙基氨基乙酯。苯乙烯类单体的实例是苯乙烯、4-甲基苯乙烯和4-乙烯基联苯。乙烯基单体的实例是乙烯醇、氯乙烯、偏二氯乙烯、乙烯基异丁基醚和乙酸乙烯酯。烯烃单体的实例是乙烯、丙烯、丁二烯和异戊二烯和它们的氯化或氟化衍生物,如四氟乙烯。马来酸类单体的实例是马来酸、马来酸酐和马来酰亚胺。
丙烯酸类聚合物的实例是聚(甲基丙烯酸甲酯)(PMMA)、聚(甲基丙烯酸丁酯)、聚丙烯腈(PAN)、聚丙烯酸、苯乙烯/丙烯酸2-乙基己酯共聚物、苯乙烯/丙烯酸共聚物。
苯乙烯类聚合物可以是由至少一种苯乙烯类单体或由至少一种苯乙烯类单体和至少一种乙烯基单体、烯烃单体和/或马来酸类单体形成的聚合物。苯乙烯类聚合物的实例是聚苯乙烯(PS)、苯乙烯丁二烯苯乙烯嵌段聚合物、苯乙烯乙烯丁二烯嵌段聚合物、苯乙烯乙烯丙烯苯乙烯嵌段聚合物和苯乙烯-马来酸酐共聚物。
乙烯基聚合物可以是由至少一种乙烯基单体或由至少一种乙烯基单体和至少一种烯烃单体或马来酸类单体形成的聚合物。乙烯基聚合物的实例是聚氯乙烯(PVC)、聚偏二氟乙烯(PVDF)、聚乙烯醇、聚乙酸乙烯酯、部分水解的聚乙酸乙烯酯和甲基乙烯基醚-马来酸酐共聚物。它们的衍生物的实例是羧基改性的聚乙烯醇、乙酰乙酰基改性的聚乙烯醇、双丙酮改性的聚乙烯醇和硅改性的聚乙烯醇。
聚烯烃可以是由至少一种烯烃单体或由至少一种烯烃单体和马来酸类单体形成的聚合物。聚烯烃的实例是低密度聚乙烯(LDPE)、高密度聚乙烯(HDPE)、聚丙烯(PP)、双轴取向的聚丙烯(BOPP)、聚丁二烯、聚四氟乙烯(Teflon-PTFE)、氯化聚乙烯和异丙烯-马来酸酐共聚物。
醛聚合物可以是由至少一种醛单体或聚合物和至少一种醇单体或聚合物、胺单体或聚合物和/或脲单体或聚合物形成的聚合物。醛单体的实例是甲醛、糠醛和丁醛。醇单体的实例是苯酚、甲酚、间苯二酚和二甲苯酚。聚醇的实例是聚乙烯醇。胺单体的实例是苯胺和三聚氰胺。脲单体的实例是脲、硫脲和双氰胺。醛聚合物的实例是由丁醛和聚乙烯醇形成的聚乙烯基丁醛。
环氧化物聚合物可以是由至少一种环氧化物单体和至少一种醇单体和/或胺单体形成的聚合物。环氧化物单体的实例是表氯醇和缩水甘油。醇单体的实例是苯酚、甲酚、间苯二酚、二甲苯酚、双酚A和乙二醇。环氧化物聚合物的实例是由表氯醇和双酚A形成的苯氧基树脂。
聚酰胺可以是由至少一种具有酰胺基团或氨基以及羧基的单体或由至少一种具有两个氨基的单体和至少一种具有两个羧基的单体形成的聚合物。具有酰胺基团的单体的实例是己内酰胺。二胺的实例是1,6-二氨基己烷。二羧酸的实例是己二酸、对苯二甲酸、间苯二甲酸和1,4-萘二甲酸。聚酰胺的实例是聚己二酰己二胺和聚己内酰胺。
聚酯可以是由至少一种具有羟基以及羧基的单体或由至少一种具有两个羟基的单体和至少一种具有两个羧基或内酯基团的单体形成的聚合物。具有羟基以及羧基的单体的实例是己二酸。二醇的实例是乙二醇。具有内酯基团的单体的实例是己内酯。二羧酸的实例是对苯二甲酸、间苯二甲酸和1,4-萘二甲酸。聚酯的实例是聚对苯二甲酸乙二酯(PET)。所谓的醇酸树脂也被认为属于聚酯聚合物。
聚氨酯可以是由至少一种二异氰酸酯单体和至少一种多元醇单体和/或聚胺单体形成的聚合物。二异氰酸酯单体的实例是己二异氰酸酯、甲苯二异氰酸酯、异佛尔酮二异氰酸酯和二苯甲烷二异氰酸酯。
聚碳酸酯的实例是聚(芳族碳酸酯)和聚(脂族碳酸酯)。聚(脂族碳酸酯)可以由二氧化碳和至少一种环氧化物形成。
砜基聚合物的实例是聚芳基砜、聚醚砜(PES)、聚苯基砜(PPS)和聚砜(PSF)。聚砜(PSF)是由4,4-二氯二苯砜和双酚A形成的聚合物。
天然聚合物的实例是淀粉、纤维素、明胶、caesin和天然橡胶。衍生物的实例是氧化淀粉、淀粉-乙酸乙烯酯接枝共聚物、羟乙基纤维素、羟丙基纤维素、甲基纤维素、硝基纤维素、乙基纤维素、羧甲基纤维素和乙酰基纤维素。
基底可以是用在医学领域中的基底,如创伤护理绷带、导管、植入物、人造器官、人造关节、人造血管和医用器材,如听诊器、管、注射器和针头。
基底可以是water liner或包装,例如食品包装。基底也可以是膜。
基底可以含有杀生物剂。
优选基底由聚合物制成。更优选基底由选自由苯乙烯聚合物、乙烯基聚合物及其衍生物、聚烯烃、聚酯和砜基聚合物组成的组中的聚合物制成。再更优选基底由聚烯烃制成。最优选基底由聚丙烯(PP)或双轴取向的聚丙烯(BOPP)制成。
优选由聚合物制成的基底是膜。
基底表面的氧化可以例如通过用电晕放电、等离子体、火焰、臭氧、电子束、X-射线或紫外线辐射处理来进行。
电晕放电可以是以电晕为特征的放电,并在气体中的两个电极之一具有使其表面的电场明显高于电极之间的电场的形状时发生。常用空气作为气体。基底通常在环境压力下位于这两个电极之间的放电场中,例如通过使作为基底的薄膜在两个电极之间穿过。
等离子体可以是其中存在电子和离子的气体。等离子体可以通过用高温或高电场处理气体来产生。等离子体处理通常在真空室中在10至100Pa下在由惰性气体或反应性气体,例如氧气构成的气氛中用非热等离子体进行。
火焰可以是在将可燃气体和含氧气体(例如大气空气)合并并燃烧时形成的火焰。可燃气体的实例是丙烷、丁烷或民用燃气。火焰处理通常在环境温度下进行。
臭氧可以在电晕放电中由大气氧产生或通过紫外线辐射产生。
电子束可以由电子束加速器,例如由阴极射线管产生。
X-射线可以由X-射线发生器,例如由X-射线管产生。
优选,表面的氧化通过用电晕放电、等离子体或火焰处理来进行。其更优选通过电晕放电处理进行。
可以使用任何能够聚合的带有一个或多个烯键式不饱和基团的季铵化合物。优选,所述一种或多种带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢、卤素或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基、C2-30-烯基、C3-8-环烷基、芳基,或R4和R5与铵基团的N一起形成4至8元环,其中该环的一个CH2基团可以被NH或O替代,
Q和Y可以相同或不同并且是C1-15-亚烷基,
M是桥连基,
n和m可以相同或不同并且是0或1,
J-是阴离子,
其中C1-30-烷基、C2-30-烯基、C3-8-环烷基或C1-15-亚烷基可以是未取代的或被一个或多个芳基、OC2-6-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中芳基可以是未取代的或被一个或多个C1-6-烷基、C2-6-烯基、OC2-6-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20和R21可以相同或不同并且是氢或C1-6-烷基,
且C1-15-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代。
C1-6-烷基可以是带支链或直链的并且可以是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基或己基。
C1-30-烷基可以是带支链或直链的。C1-30-烷基的实例是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基和三十烷基。
C3-8-环烷基的实例是环丙基、环丁基、环戊基、环己基、环庚基和环辛基。
C2-30-烯基和C1-6-烯基的实例是乙烯基和烯丙基。
芳基可以是苯基或萘基或杂芳基,如咪唑基、吡咯基或异氰尿酰基。优选芳基是苯基。
C1-15-亚烷基的实例是亚甲基、亚丙基和亚丁基。
桥连基M的实例是C3-8-亚环烷基、亚芳基、聚合物、OC(O)、C(O)O、NH(CO)和C(O)NH。亚芳基可以是亚苯基。聚合物的实例是聚乙烯亚胺。
J-可以是任何阴离子,例如硫酸根、亚硫酸根、碳酸根、磷酸根或卤素离子。卤素离子可以是氟离子、氯离子、溴离子或碘离子。
带有一个或多个烯键式不饱和基团的季铵化合物的实例是丙烯酸三甲基氨基乙基酯氯化物、甲基丙烯酸三甲基氨基乙基酯氯化物、丙烯酸三甲基氨基十四烷基酯氯化物、丙烯酸三甲基氨基十六烷基酯氯化物、丙烯酸三甲基氨基十八烷基酯氯化物和二烯丙基二甲基氯化铵和下式的化合物:
和
更优选的带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基或C2-30-烯基,
Q和Y可以相同或不同并且是C1-15-亚烷基,
M是选自由亚芳基、聚合物、OC(O)和C(O)O组成的组的桥连基,
n和m可以相同或不同并且是0或1,
J-是卤素离子,
其中C1-30-烷基、C2-30-烯基或C1-15-亚烷基可以是未取代的或被一个或多个OC2-6-烯基、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20和R21可以相同或不同并且是氢或C1-6-烷基,
且C1-15-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代。
最优选的带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基,
Q和Y可以相同或不同并且是C1-6-亚烷基,
M是选自由聚合物和OC(O)组成的组的桥连基,
n和m可以相同或不同并且是0或1,
J-是卤素离子,
其中C1-30-烷基或C1-6-亚烷基可以是未取代的或被一个或多个OR10取代,
其中R10可以是氢或C1-6-烷基,
且C1-6-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2替代。
C1-6-亚烷基的实例是亚甲基、亚丙基和亚丁基。
化合物1A是尤其优选的带有一个或多个烯键式不饱和基团的季铵化合物。
式1的化合物可以例如通过使下式的胺:
与下式的化合物反应来制备:
J-R4 (3)。
例如,化合物1A可以如S.M.Hamid和D.C.Sherrington,Polymer1987,28,325至331中所述通过使甲基丙烯酸N,N-二甲基氨基乙酯与十二烷基溴反应来制备。
所述包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物还可以包含一种或多种其它烯键式不饱和化合物,其可以是能够聚合的任何烯键式不饱和化合物。
所述其它烯键式不饱和化合物可以是能够形成具有至少五个大分子单体单元的聚合物的大分子单体,该大分子单体具有1’000至1’000’000’000克/摩尔的分子量并带有烯键式不饱和基团。优选的大分子单体是其中烯键式不饱和基团是(甲基)丙烯酰基部分的那些。这类大分子单体的实例是(甲基)丙烯酰基-改性的聚酯、(甲基)丙烯酰基-改性的聚乙烯醇、(甲基)丙烯酰基-改性的部分水解的聚乙酸乙烯酯、(甲基)丙烯酰基-改性的甲基乙烯基醚-马来酸酐共聚物、(甲基)丙烯酰基-改性的甲基异丙烯-马来酸酐共聚物、(甲基)丙烯酰基-改性的聚氨酯和(甲基)丙烯酰基-改性的纤维素。
特别优选的大分子单体是带有至少两个烯键式不饱和基团(其是(甲基)丙烯酰基部分)的那些。
带有至少两个丙烯酰基部分的大分子单体的实例是Sartomercompany出售的Sartomer CN2301,其是含有多个丙烯酸酯官能的支化聚酯丙烯酸酯低聚物。
所述其它烯键式不饱和化合物也可以具有下式:
其中
R22、R23和R24可以相同或不同并且可以是氢、卤素或C1-6-烷基,
A可以是芳基、卤素、CN、C(O)R25、C(O)OR26、OR27、OC(O)R28、NR29C(O)R30或C(O)NR31R32,其中芳基可以是未取代的或如下所述取代,其中
R25、R26、R27、R28、R31和R32可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基、C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2或芳基-C1-30-亚烷基-芳基,且R29和R30可以相同或不同并且可以具有与R26相同的含义,此外,可以与NC(O)一起形成4至7元环,其中
C1-100-烷基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基和C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2可以是未取代的或被一个或多个C3-8-环烷基、芳基、OC2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代;
C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代,
芳基或芳基-C1-30-亚烷基-芳基可以是未取代的或被一个或多个C1-6-烷基、C3-8-环烷基、C2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代,其中
R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46和R47可以相同或不同并且可以是氢或C1-6-烷基,且其中
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
C1-100-烷基可以是带支链或直链的。C1-100-烷基的实例是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基十四烷基、十五烷基、十六烷基、十八烷基、十九烷基(icosyl)、二十烷基、二十二烷基、二十四烷基和三十烷基。
C1-6-亚烷基-芳基-(C1-6-烷基)2的实例是异氰脲酸三乙酯。C1-6-亚烷基-C1-12-环烷基-C1-6-烷基的实例是二甲基三环癸烷。
芳基-C1-30-亚烷基-芳基的实例是苯基-亚乙基-苯基和苯基-亚丙基-苯基。
式4的烯键式不饱和化合物的实例是丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯、丙烯酸2-羟乙酯、甲基丙烯酸缩水甘油酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、丙烯腈、丙烯酰胺、甲基丙烯酸、甲基丙烯酰胺、乙酸乙烯酯、异丁基乙烯基醚、苯乙烯、N-乙烯基吡咯烷酮、氯乙烯、偏二氯乙烯、乙二醇二丙烯酸酯、六亚甲基二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、双酚A二丙烯酸酯、三环癸烷二甲醇二丙烯酸酯、4,4’-双(2-丙烯酰氧基乙氧基)二苯丙烷、丙烯酸乙烯酯、甲基丙烯酸乙烯酯、二乙烯基苯、琥珀酸二乙烯酯、乙二醇二乙烯基醚、二乙二醇二乙烯基醚、三乙二醇二乙烯基醚、甘油乙氧基化物三丙烯酸酯、甘油丙氧基化物三丙烯酸酯、三羟甲基丙烷乙氧基化物三丙烯酸酯、三羟甲基丙烷丙氧基化物三丙烯酸酯、异氰脲酸三丙烯酸2-羟乙酯、季戊四醇乙氧基化物四丙烯酸酯、季戊四醇丙氧基化物三丙烯酸酯、季戊四醇丙氧基化物四丙烯酸酯、三羟甲基丙烷三丙烯酸酯、乙氧基化(6)三羟甲基丙烷三丙烯酸酯、乙氧基化(9)三羟甲基丙烷三丙烯酸酯、乙氧基化(15)三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、新戊二醇乙氧基化物二丙烯酸酯和新戊二醇丙氧基化物二丙烯酸酯、聚乙二醇(400)二丙烯酸酯、聚乙二醇(400)二甲基丙烯酸酯、聚乙二醇(600)二丙烯酸酯、聚乙二醇(600)二甲基丙烯酸酯和聚乙二醇-单-甲基丙烯酸酯。
优选地,R22、R23和R24相同或不同并且是氢或C1-6-烷基。
优选A是C(O)OR26或C(O)NR31R32、其中R26、R31和R32可以相同或不同并且是氢、C1-100-烷基、C2-30-烯基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基或芳基-C1-30-亚烷基-芳基;其中C1-100-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2和C1-6-亚烷基-C1-12-环烷基-C1-6-烷基被一个或多个OC(O)C(R42)=C(R43)R44或NHC(O)C(R39)=C(R40)R41取代,并且可以另外被一个或多个C3-8-环烷基、O-C2-30-烯基、OR36、NR37R38或C(O)OC(R45)=C(R46)R47取代,且芳基被一个或多个C(O)C(R42)=C(R43)R44取代;R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46和R47可-以相同或不同并且是氢或C1-6-烷基,且C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
更优选A是C(O)OR26,其中R26是C1-100-烷基,其中C1-100-烷基被一个或多个OC(O)C(R42)=C(R43)R44取代;R42、R43和R44可以相同或不同并且是氢或C1-6-烷基,且C1-100-烷基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代。
最优选A是C(O)OR26,其中R26是C1-100-烷基,其中C1-100-烷基被一个或多个OC(O)C(R42)=C(R43)R44取代;R42、R43和R44可以相同或不同并且是氢或C1-6-烷基,且C1-100-烷基中的一个或多个CH2-基团可以被-O-替代。
最优选的式4的烯键式不饱和化合物的实例是乙二醇二丙烯酸酯、六亚甲基二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、甘油乙氧基化物三丙烯酸酯、甘油丙氧基化物三丙烯酸酯、三羟甲基丙烷乙氧基化物三丙烯酸酯、三羟甲基丙烷丙氧基化物三丙烯酸酯、季戊四醇乙氧基化物四丙烯酸酯、季戊四醇丙氧基化物三丙烯酸酯、季戊四醇丙氧基化物四丙烯酸酯、三羟甲基丙烷三丙烯酸酯、乙氧基化(6)三羟甲基丙烷三丙烯酸酯、乙氧基化(9)三羟甲基丙烷三丙烯酸酯、乙氧基化(15)三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、新戊二醇乙氧基化物二丙烯酸酯、新戊二醇丙氧基化物二丙烯酸酯、聚乙二醇(400)二丙烯酸酯、聚乙二醇(400)二甲基丙烯酸酯、聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯。
上列化合物可购得。例如,聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯可获自Sartomer Company。或者,这些化合物可以通过使相应的醇分别与丙烯酸甲酯和甲基丙烯酸甲酯反应来制备。例如,聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯可以通过使聚乙二醇(600)分别与丙烯酸甲酯和甲基丙烯酸甲酯反应来制备。
所述其它烯键式不饱和化合物也可以是烯丙基,例如邻苯二甲酸二烯丙酯、磷酸三烯丙酯和异氰脲酸三烯丙酯。
所述包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物还可以包含一种或多种自由基引发剂。
所述一种或多种自由基引发剂可以是热引发剂,如2,2-偶氮二异丁腈或光引发剂。优选所述一种或多种自由基引发剂是光引发剂。
光引发剂可以具有下式:
其中
L可以是氢或
其中C1-6-亚烷基可以是未取代的或被羟基取代,且
R48、R49和R50可以相同或不同并且可以是氢、卤素、羟基、C1-6-烷基、芳基、O-C1-6-烷基、O-芳基、S-C1-6-烷基、S-芳基或NR51R52,其中R51和R52可以相同或不同并且可以是氢或C1-6-烷基,或与氮一起形成5至7元环,其中该环的CH2基团可以被-O-替代,且C1-6-烷基、O-C1-6-烷基和S-C1-6-烷基可以是未取代的或被一个或多个羟基、C2-30-烯基、OC(O)C2-30-烯基或芳基取代,且
X可以是
其中E和G可以是-O-、-S-或NR61,其中R61可以是氢或C1-6-烷基,或R61分别和R53或和R56可以与氮一起形成5至7元环,其中该环的CH2基团可以被-O-、NH、NC(O)C(R62)C=C(R63)R64和/或
R53、R56和R60可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R65;
R57、R58和R59可以相同或不同并且可以是氢、C1-100-烷基、O-C1-100-烷基、S-C1-100-烷基、NR66C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R65,其中R66可以具有与R53相同的含义,且R65可以具有与R57相同的含义;
R54和R55可以具有与R57相同的含义,此外,可以与连接碳原子一起形成5至7元环,
C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、氨基、羟基、CN、COOH、C(O)R67、C(O)OR68、C(O)NR69R70、OR71、OC(O)R72、OC(O)C(R73)=C(R74)R75、C(O)OC(R76)=C(R77)R78、
或取代,
其中R62、R63、R64、R67、R68、R69、R70、R71、R72、R73、R74、R75、R76、R77和R78可以相同或不同并且可以是氢或C1-6-烷基,
芳基可以是未取代的或被一个或多个C1-4-烷基、C3-8-环烷基、C2-30-烯基、卤素、羟基、CN、COOH、C(O)R67、C(O)OR68、C(O)NR69R70、OR71、OC(O)R72、OC(O)C(R73)=C(R74)R75或C(O)OC(R76)=C(R77)R78取代;且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NR61-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
C1-6-亚烷基的实例是亚甲基、亚丙基和亚丁基。
C1-100-烷基可以是带支链或直链的。C1-100-烷基的实例是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基和三十烷基。
式5的光引发剂的实例是苯偶姻醚如苯偶姻乙基醚,苄基单缩酮如2,2-二乙氧基-1-苯基乙酮和2,2-二乙氧基-1,2-二苯基乙酮,α-取代的苯乙酮衍生物如2-羟基-2-甲基1-苯基丙-1-酮(Ciba Specialty Chemicals以商品名CibaDarocure1173出售)、1-羟基环己基苯基酮、2-甲基-4’-(甲硫基)-2-吗啉基苯丙酮和2-苄基-2-(二甲基氨基)-4’-吗啉基苯丁酮,酰基膦氧化物如二苯基(2,4,6-三甲基苯甲酰基)-氧化膦(BASF以商品名LucirinTPO出售)或苯基双(2,4,6-三甲基苯甲酰基)-氧化膦(Ciba Specialty Chemicals以商品名CibaIrgacure 819出售),α-酰基肟酯如1-[4-(苯硫基)苯基]-2-(O-苯甲酰基肟)辛-1,2-二酮,和苯基乙醛酸酯如二乙二醇二(苯基乙醛酸酯)、三乙二醇二(苯基乙醛酸酯)、聚乙二醇(150)二(苯基乙醛酸酯)、聚乙二醇(300)二(苯基乙醛酸酯)、聚乙二醇(400)二(苯基乙醛酸酯)和聚乙二醇(600)二(苯基乙醛酸酯)。
在优选的式5的化合物中,R48、R49和R50可以相同或不同并且是氢、羟基、C1-6-烷基、O-C1-6-烷基、S-C1-6-烷基、S-芳基或NR51R52,其中R51和R52可以相同或不同并且可以是氢或C1-6-烷基,或与氮一起形成5至7元环,其中该环的CH2基团可以被-O-替代,且C1-6-烷基和O-C1-6-烷基可以是未取代的或被羟基、C2-30-烯基或芳基取代,且
X是
其中E和G是-O-或NR61,其中R61可以是氢或C1-6-烷基,或R61分别和R53或和R56可以与氮一起形成5至7元环,其中该环的CH2基团可以被-O-、NH、NC(O)C(R62)C=C(R63)R64和/或
替代,
R53、R56和R60可以相同或不同并且是氢、C1-100-烷基、C2-30-烯基、芳基或C(O)R65;R57、R58和R59可以相同或不同并且是氢、C1-100-烷基、O-C1-100-烷基、芳基或C(O)R65;R54和R55可以具有与R57相同的含义,此外可以与连接碳原子一起形成5至7元环,R65具有与R57相同的含义,
C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个芳基、氨基、羟基、OC(O)C(R73)=C(R74)R75、C(O)OC(R76)=C(R77)R78、
其中R62、R63、R64、R73、R74、R75、R76、R77和R78可以相同或不同并且是氢或C1-6-烷基,
芳基可以是未取代的或被一个或多个C1-4-烷基取代,且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-和/或-NR61替代。
光引发剂也可以是二茂钛,或者是二苯甲酮或噻吨酮衍生物与助引发剂(例如叔胺)的组合。但优选光引发剂为式5的化合物。
所述包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物还可以包含溶剂。
溶剂可以是水、有机溶剂或其混合物。
有机溶剂的实例是C1-4-链烷醇、C2-4-多元醇、C3-6-酮、C4-6-醚、C2-3-腈、硝基甲烷、二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮和环丁砜,其中C1-4-链烷醇和C2-4-多元醇可以被C1-4-烷氧基取代。C1-4-链烷醇的实例是甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、仲丁醇和叔丁醇。其C1-4-烷氧基衍生物的实例是2-乙氧基乙醇和1-甲氧基-2-丙醇。C2-4-多元醇的实例是乙二醇和丙三醇。C3-6-酮的实例是丙酮和甲乙酮。C4-6-醚的实例是二甲氧基乙烷、二异丙基醚和四氢呋喃。C2-3-腈的实例是乙腈。有机溶剂优选选自C1-4-链烷醇、C2-4-多元醇、C3-6-酮、二甲基甲酰胺和二甲基乙酰胺,其中C1-4-链烷醇和C2-4-多元醇可以被C1-4-烷氧基取代。有机溶剂更优选是C1-4-链烷醇。
溶剂优选是水或水和有机溶剂的混合物。
所述包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物还可以包含其他组分,如杀生物剂、表面活性剂和消泡剂。
杀生物剂的实例是5-氯-2-(2,4-二氯苯氧基)苯酚,例如以商品名CibaIrgasanDP300出售;N’-叔丁基-N-环丙基-6-(甲硫基)-1,3,5-三嗪-2,4-二胺,例如以商品名CibaIrgarol1051出售;2-噻唑-4-基-1H-苯并咪唑,例如以商品名CibaIrgaguardF3000出售;氯己定;没食子酸;粘溴酸;衣康酸;和氨基甲酸3-碘-2-丙炔基丁基酯,例如以商品名MaguardTM I-100出售。
表面活性剂的实例是阴离子型表面活性剂,如十二烷基硫酸钠或月桂基硫酸铵,阳离子型表面活性剂,如鲸蜡基三甲基溴化铵或鲸蜡基氯化吡啶鎓,两性表面活性剂,如十二烷基甜菜碱,和非离子型表面活性剂,如聚(环氧乙烷)和聚(环氧丙烷)的共聚物。
所述组合物可以包含基于组合物重量为0.001至100重量%的一种或多种带有一个或多个烯键式不饱和基团的季铵化合物。其优选包含0.01至80重量%,更优选0.1至50重量%,最优选0.1至30重量%的一种或多种季铵化合物。
所述组合物可以包含基于组合物重量为0至99重量%的一种或多种其它烯键式不饱和化合物。其优选包含0.01至80重量%的一种或多种烯键式不饱和化合物,更优选0.1至70重量%。
所述组合物可以包含基于组合物重量为0至50重量%的一种或多种自由基引发剂。其优选包含0.01至20重量%的一种或多种自由基引发剂,更优选0.1至10重量%。
所述组合物可以包含基于组合物重量为0至99.999重量%的溶剂。其优选包含10至99.9重量%的溶剂,更优选20至99.5重量%。
所述组合物可以包含基于组合物重量为0至50重量%的其他组分。其优选包含0.001至10重量%的其他组分,更优选0.01至5重量%。
所述包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物可以是溶液、乳液或分散体。所述组合物优选是溶液。所述组合物可以例如使用线棒或通过浸溃或喷涂法施加。
可以通过所述一种或多种带有一个或多个烯键式不饱和基团的季铵化合物和能够聚合并任选存在于该组合物中的其它组分(例如其它烯键式不饱和化合物)的聚合实现组合物的固化。
如果在基底的氧化表面上存在充足自由基,则所述带有一个或多个烯键式不饱和基团的季铵化合物可以在施加后聚合而无需任何其他处理。但是,通常,通过用热、电子束或电磁辐射处理来引发聚合。电磁辐射的实例X-射线、γ射线、紫外线辐射、红外辐射、可见光或微波。优选通过用电磁辐射处理,更优选通过用紫外线辐射处理来引发聚合。通常,紫外线辐射在60至300瓦特/cm和1至1000米/分钟,优选10至200米/分钟的带速下进行。
优选在仅含痕量氧的惰性气体气氛下进行聚合。惰性气体的实例是氮气、氩气、二氧化碳和氦气。优选,惰性气体气氛中存在的氧的量低于1000体积ppm,更优选低于500体积ppm,最优选低于150体积ppm。
固化涂层可具有0.1至100微米,优选1至50微米的厚度。
此外,杀生物剂可以例如在表面氧化之前(在步骤(i)之前)、在表面氧化之后和在施加所述组合物之前(在步骤(i)之后和在步骤(ii)之前)、在施加所述组合物之后和在固化之前(在步骤(ii)之后和在步骤(iii)之前)或在固化所述组合物之后(在步骤(iii)之后)施加在基底表面上。
基底也可以用另外的涂层涂布,该另外的涂层可以在由本发明的方法形成的涂层之前或之后施加到基底上。
优选地,本发明的方法中所用的基底已经涂有一个或多个预涂层。
优选地,该预涂层通过包含下列步骤的方法形成:
(i)氧化基底表面
(ii)将包含一种或多种烯键式不饱和化合物的组合物施加到所述基底的氧化表面上
(iii)固化该组合物以形成预涂层。
用于形成预涂层的组合物还可以包含一种或多种自由基引发剂、溶剂和其他组分。
用于形成预涂层的组合物还可以包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物,尽管这不是优选的。
烯键式不饱和化合物、自由基引发剂、溶剂、其他组分和带有一个或多个烯键式不饱和基团的季铵化合物的定义与上文中相同。表面的氧化、组合物的施加和组合物的固化也与上述相同。
可通过这一方法获得的基底也是本发明的一部分。
一种或多种带有一个或多个烯键式不饱和基团的季铵化合物和一种或多种烯键式不饱和化合物的混合物也是本发明的一部分,
其中带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢、卤素或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基、C2-30-烯基、C3-8-环烷基、芳基,或R4和R5与铵基团的N一起形成4至8元环,其中该环的一个CH2基团可以被NH或O替代,
Q和Y可以相同或不同并且是C1-6-亚烷基,
M是桥连基,
n和m可以相同或不同并且是0或1,
J-是阴离子,
其中C1-30-烷基、C2-30-烯基、C3-8-环烷基或C1-6-亚烷基可以是未取代的或被一个或多个芳基、OC2-30-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中芳基可以是未取代的或被一个或多个C1-6-烷基、C2-6-烯基、OC2-30-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20和R21可以相同或不同并且是氢或C1-6-烷基,
且C1-6-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代,和
所述一种或多种烯键式不饱和化合物具有下式:
其中
R22、R23和R24可以相同或不同并且可以是氢、卤素或C1-6-烷基,
A可以是芳基、卤素、CN、C(O)R25、C(O)OR26、OR27、OC(O)R28、NR29C(O)R30或C(O)NR31R32、其中芳基可以是未取代的或如下所述取代,其中
R25、R26、R27、R28、R31和R32可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基、C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2或芳基-C1-30-亚烷基-芳基,且R29和R30可以相同或不同并且可以具有与R26相同的含义,此外,可以与NC(O)一起形成4至7元环,其中
C1-100-烷基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基和C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2可以是未取代的或被一个或多个C3-8-环烷基、芳基、OC2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代;
C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代,
芳基或芳基-C1-30-亚烷基-芳基可以是未取代的或被一个或多个C1-6-烷基、C3-8-环烷基、C2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代,其中
R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46和R47可以相同或不同并且可以是氢或C1-6-烷基,且其中
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
对式1和4的化合物给出的优选也适用于这些化合物的混合物。
本发明的方法赋予基底表面生物杀灭活性的用途也是本发明的一部分。
特别地,本发明的方法赋予医学领域中所用的基底的表面生物杀灭活性的用途也是本发明的一部分。这类基底的实例是体内使用的基底,如植入物、人造器官、人造关节、人造血管和医用器材,如创伤护理绷带、导管、听诊器、管、注射器和针头。
本发明的方法的优点在于,可以在现有印刷设备上在大规模连续工艺中简单地用杀生物涂层涂布基底。此外,如果存在一个或多个预涂层,这些预涂层的优点在于,通过本发明的方法形成的杀生物涂层的附着效力和渗透性与基底无关。
在所得杀生物涂层中,杀生物剂共价连接到基底上,因此不会泄漏到环境中。因此,不与基底表面直接接触的活生物体不受基底表面的生物杀灭活性的影响。除了不对非目标生物体造成危害外,也不会在微生物,例如细菌中形成对杀生物剂的抗性。
如果由包含能够形成具有至少五个大分子单体单元的聚合物的大分子单体(该大分子单体具有1’000至1’000’000’000克/摩尔的分子量并带有至少两个烯键式不饱和基团(其是(甲基)丙烯酰基部分))的组合物形成杀生物涂层或如果由包含优选的式4化合物的组合物形成杀生物涂层,则该杀生物涂层也表现出极高耐久性,这意味着在该杀生物层暴露在各种环境条件下时,例如在杀生物层长期暴露在水中时,该杀生物涂层的生物杀灭活性不会被显著影响。
实施例
实施例1
化合物1A的制备
将甲基丙烯酸N,N-二甲基氨基乙酯(28.4克,0.18摩尔)、乙腈(210克)和十二烷基溴(48.2克,0.19摩尔)添加到1000毫升圆底烧瓶中。将该反应混合物在冰水浴中冷却并加入乙醚直至形成沉淀物。过滤该沉淀物并干燥产生白色固体(54.5克,70.8%收率)。1HNMR(300MHz,CDCl3):0.87(t,3H,烷基末端CH3),1.24至1.33(m,18H,烷基CH2),1.7(m,2H,N-CH2CH 2),1.95(s,3H,烯丙基CH3),3.49(s,6H,N(CH3)2),3.6(m,2H,NCH2),4.16(m,2H,O-CH2),4.64(m,2H,O-CH2CH 2),5.67,(s,1H,顺式乙烯基H),6.14(s,1H,反式乙烯基H)。
实施例2
使用包含化合物1A的第一组合物在基底表面上形成涂层
AmTopp供应的“AmTopp-Cl50”,双轴取向聚丙烯(BOPP)膜在一面上使用具有42毫米宽度的电极进行电晕预处理,带速为50米/分钟,电晕放电为680W。然后,使用40微米线棒在该BOPP膜的一面上施加33/65/2(重量/重量/重量)1A/丙烯酸丁酯/CibaIrgacure2022的混合物在甲醇中的75重量%溶液。储存该处理过的BOPP膜直至甲醇蒸发。将该处理过的干的BOPP膜在含有大约500ppm氧的氮气氛下使用在12米/分钟带速下的带有输出为120W/cm的中压汞灯的UV处理器和聚焦椭圆反射镜照射。
CibaIrgacure2022是苯基双(2,4,6-三甲基苯甲酰基)-氧化膦(CibaSpecialty Chemicals出售的CibaIrgacure819)/二苯基(2,4,6-三甲基苯甲酰基)-氧化膦(BASF出售的LucirinTPO)/2-羟基-2-甲基-1-苯基丙-1-酮(Ciba Specialty Chemicals出售的CibaDarocur1173)的17/5/78(重量/重量/重量)混合物。
实施例3
使用包含化合物1A的第二组合物在基底表面上形成涂层
重复实施例2的方法,不同的是使用40微米线棒在该BOPP膜的一面上施加16.4/32.8/1.6/49.2(重量/重量/重量/重量)1A/丙烯酸丁酯/CibaIrgacure2022/Sartomer CN2301的混合物在甲醇中的75重量%溶液代替33/65/2(重量/重量/重量)1A/丙烯酸丁酯/CibaIrgacure2022的混合物在甲醇中的75重量%溶液。
Sartomer CN2301是由Sartomer company出售的含有多个丙烯酸酯官能的支化聚酯丙烯酸酯低聚物。
实施例4
使用包含化合物1A的第二组合物在基底表面上形成涂层
重复实施例3的方法,不同的是使用4微米线棒代替40微米线棒。
对比例1
使用不含化合物1A的第二组合物在基底表面上形成涂层
重复实施例4的方法,不同的是使用49.0/2.0/49.0(重量/重量/重量)丙烯酸丁酯/CibaIrgacure2022/Sartomer CN2301的混合物在甲醇中的75重量%溶液代替16.4/32.8/1.6/49.2(重量/重量/重量/重量)1A/丙烯酸丁酯/CibaIrgacure2022/Sartomer CN2301的混合物在甲醇中的75重量%溶液。
对比例2
在基底表面上形成预涂层
AmTopp供应的“AmTopp-Cl50”,双轴取向聚丙烯(BOPP)膜的表面在一面上使用具有42毫米宽度的电极进行电晕预处理,带速为50米/分钟,电晕放电为680W。然后,用苯胺印刷工作站使用800LPI 2.2BCManilox辊和橡胶套在50米/分钟压制速度下以1克(湿重量)/平方米速率施加31.9/13.7/9.1/22.7/22.7(重量/重量/重量/重量)
/三丙二醇二丙烯酸酯/苯基双(2,4,6-三甲基苯甲酰基)-氧化膦(CibaSpecialty Chemicals出售的CibaIrgacure819)/三环癸烷二甲醇二丙烯酸酯(Sartomer company以SR 833S出售)/异氰脲酸2-羟基乙酯(Sartomer company以SR 368出售)的混合物在异丙醇中的2.2重量%溶液。将该湿幅干燥并使用额定500W/inch(=约200W/cm)并在70%输出下运行的中压汞灯通过UV照射固化。
实施例5
使用包含1A的第二组合物在已具有预涂层的基底表面上形成涂层
重复实施例3的方法,不同的是使用对比例2中获得的BOPP膜。
实施例6
使用包含1A的第二组合物在已具有预涂层的基底表面上形成涂层
重复实施例4的方法,不同的是使用对比例2中获得的BOPP膜。
对比例3
使用不含1A的第二组合物在已具有预涂层的基底表面上形成涂层
重复实施例6的方法,不同的是使用49.0/2.0/49.0(重量/重量/重量)丙烯酸丁酯/CibaIrgacure2022/Sartomer CN2301的混合物在甲醇中的75重量%溶液代替16.4/32.8/1.6/49.2(重量/重量/重量/重量)1A/丙烯酸丁酯/CibaIrgacure2022/Sartomer CN2301的混合物在甲醇中的75重量%溶液。
实施例2至6的处理过的BOPP膜的杀菌活性的测定
实施例2至6中获得的处理过的BOPP膜通过浸入无菌去离子水中1分钟来洗涤,然后在层流下干燥。细菌株(分别为大肠杆菌(Escherichiacoli)ATCC 10536,和金黄色葡萄球菌(Staphylococcus aureus)ATCC 6538)的过夜培养物在含有0.5重量%胰蛋白酶大豆肉汤的0.85重量%NaCl水溶液中稀释1∶1000。将处理过的BOPP膜的样品(2×2厘米)用0.1毫升细菌悬浮液培养,从而产生大约105菌落形成单位(cfu)的活细菌最终浓度。将样品在37℃下培养24小时。培养后,如下测定活细菌浓度[cfu]:首先使用含1重量%Tween 80和0.3重量%卵磷脂作为灭活剂的磷酸盐缓冲液(0.07M,pH 7.4)从处理过的BOPP膜的表面洗脱细菌细胞,逐步1∶10稀释洗脱液,将来自各稀释步骤的等分试样固定在酪蛋白大豆粉胨琼脂板上,将板培养24至48小时,计数菌落数并再计算处理过的BOPP膜表面上的活细菌数。
也用未处理的BOPP膜(对比例4)、用电晕预处理的BOPP膜(对比例5)和用对比例1至3的处理过的BOPP膜重复相同程序。测定在37℃下培养24小时后的活细菌浓度[cfu]。结果列在下表1和2中:
表1.
表2.
根据1和2,包含季铵化合物1A的涂层表现出对金黄色葡萄球菌和大肠杆菌的优异杀菌活性。
实施例7
化合物1B的制备
将在乙醇(60克)中的N-3-氯-2-羟基丙基-N-月桂基-二甲基氯化铵(10.35克)和氢氧化钾(1.71克)添加到聚乙烯亚胺的溶液(分子量=800克/摩尔,BASF以LupasolFG出售)(5克)中,并将该混合物在氮气下在80℃下加热29小时。添加烯丙基溴(5.63克)和氢氧化钾(2.6克),并将该混合物在回流下搅拌6小时。将该反应混合物冷却,过滤并浓缩产生不透明的浅黄色浆(syryp)。在真空中干燥22小时后,获得8.6克化合物1B。可以通过NMR鉴定聚胺、十二烷基和烯丙基部分。对每一个十二烷基部分而言,存在大约一个烯丙基部分,对所存在的每九个亚乙基氨基部分而言,存在大约一个十二烷基部分和一个烯丙基部分。
实施例8
包含1B的第三组合物在基底表面上形成涂层
ExxonMobil Chemical Company供应的50微米宽的双轴取向聚丙烯(BOPP)膜在两面上都使用距BOPP膜0.8毫米的一个陶瓷电极进行电晕预处理,带速为3米/分钟,电晕放电为1×600W。然后,使用4微米线棒在该BOPP膜的两面上都施加90重量%的Sartomer Company以SR-610出售的下式的聚乙二醇(600)二丙烯酸酯
和下式的聚乙二醇(600)二(苯基乙醛酸酯)
的等摩尔混合物(基于4A、5A和1B的总重量)和10重量%季铵化合物1B(基于4A、5A和1B的总重量)在异丙醇中的1重量%溶液。储存该处理过的BOPP膜直至异丙醇蒸发。将该处理过的干的BOPP膜在含有大约500ppm氧的氮气氛下使用在50米/分钟带速下的带有输出为120W/cm的中压汞灯的UV处理器和分色反射镜照射。聚乙二醇(600)二(苯基乙醛酸酯)(5A)如WO 06/067061的实施例3中所述制备。
实施例9
使用包含1A的第三组合物在基底表面上形成涂层
重复实施例8的方法,不同的是在异丙醇中使用10重量%1A(基于4A、5A和1A的总重量)代替10重量1B(基于4A、5A和1B的总重量)。
实施例10
化合物1C的制备
与实施例1类似地制备化合物1C,不同的是使用丙烯酸N,N-二甲基氨基乙酯代替甲基丙烯酸N,N-二甲基氨基乙酯。1HNMR(300MHz,CDCl3):0.82(t,3H,烷基末端CH3),1.10至1.18(m,18H,烷基CH2),1.65(m,2H,N-CH2CH 2),3.45(s,6H,N(CH3)2),3.6(m,2H,NCH2),4.12(m,2H,O-CH2),4.65(m,2H,O-CH2CH 2),5.95,(d,1H,顺式乙烯基H),6.08(dd,1H,反式乙烯基H),6.40(d,1H,gem.乙烯基H)。
Claims (13)
1.涂布基底表面的方法,该方法包括下列步骤:
(i)氧化基底表面
(ii)将包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物的组合物施加到基底的氧化表面上,和
(iii)固化所述组合物以形成涂层。
2.权利要求1的方法,其中所述一种或多种带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢、卤素或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基、C2-30-烯基、C3-8-环烷基、芳基,或R4和R5与铵基团的N一起形成4至8元环,其中该环的一个CH2基团可以被NH或O替代,
Q和Y可以相同或不同并且是C1-15-亚烷基,
M是桥连基,
n和m可以相同或不同并且是0或1,
J-是阴离子,
其中C1-30-烷基、C2-30-烯基、C3-8-环烷基或C1-15-亚烷基可以是未取代的或被一个或多个芳基、OC2-6-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中芳基可以是未取代的或被一个或多个C1-6-烷基、C2-6-烯基、OC2-6-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20和R21可以相同或不同并且是氢或C1-6-烷基,
且C1-15-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代。
3.权利要求1或2的方法,其中所述组合物还包含一种或多种其它烯键式不饱和化合物。
4.权利要求1至3任一项的方法,其中所述组合物还包含一种或多种自由基引发剂。
5.权利要求1至4任一项的方法,其中所述组合物不含一种或多种自由基引发剂。
6.权利要求1至5任一项的方法,其中所述组合物还包含溶剂。
7.权利要求1至6任一项的方法,其中所述组合物还包含其他组分。
8.权利要求1至7任一项的方法,其中将一种或多种杀生物剂在步骤(i)之前、在步骤(i)之后和在步骤(ii)之前、在步骤(ii)之后和在步骤(iii)之前,或在步骤(iii)之后施加在所述基底的表面上。
9.权利要求1至8任一项的方法,其中所述基底已预涂有一个或多个预涂层。
10.可通过权利要求1至9任一项的方法获得的基底。
11.一种或多种带有一个或多个烯键式不饱和基团的季铵化合物和一种或多种烯键式不饱和化合物的混合物,其中
所述带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢、卤素或C1-6-烷基,
R4、R5和R6可以相同或不同并且是C1-30-烷基、C2-30-烯基、C3-8-环烷基、芳基,或R4和R5与铵基团的N一起形成4至8元环,其中该环的一个CH2基团可以被NH或O替代,
Q和Y可以相同或不同并且是C1-6-亚烷基,
M是桥连基,
n和m可以相同或不同并且是0或1,
J-是阴离子,
其中C1-30-烷基、C2-30-烯基、C3-8-环烷基或C1-6-亚烷基可以是未取代的或被一个或多个芳基、OC2-30-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中芳基可以是未取代的或被一个或多个C1-6-烷基、C2-6-烯基、OC2-30-烯基、卤素、CN、C(O)OR7、C(O)NR8R9、OR10、NR11R12、NHC(O)C(R13)=C(R14)R15、OC(O)C(R16)=C(R17)R18或C(O)OC(R19)=C(R20)R21取代;
其中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20和R21可以相同或不同并且是氢或C1-6-烷基,
且C1-6-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代,
所述一种或多种烯键式不饱和化合物具有下式:
其中
R22、R23和R24可以相同或不同并且是氢、卤素或C1-6-烷基,
A是芳基、卤素、CN、C(O)R25、C(O)OR26、OR27、OC(O)R28、NR29C(O)R30或C(O)NR31R32,
其中
R25、R26、R27、R28、R31和R32可以相同或不同并且是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基、C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2或芳基-C1-30-亚烷基-芳基,和R29和R30可以相同或不同并具有与R26相同的含义,或与NC(O)一起形成4至7元环,其中
C1-100-烷基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基和C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2可以是未取代的或被一个或多个C3-8-环烷基、芳基、OC2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代;
C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代;
芳基或芳基-C1-30-亚烷基-芳基可以是未取代的或被一个或多个C1-6-烷基、C3-8-环烷基、C2-30-烯基、卤素、CN、C(O)OR33、C(O)NR34R35、OR36、NR37R38、NHC(O)C(R39)=C(R40)R41、OC(O)C(R42)=C(R43)R44或C(O)OC(R45)=C(R46)R47取代,其中
R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46和R47可以相同或不同并且是氢或C1-6-烷基,且其中
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
12.权利要求1至9任一项的方法赋予基底表面生物杀灭活性的用途。
13.权利要求12的方法,其中所述基底是医学领域中所用的基底。
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CN104383600A (zh) * | 2014-10-20 | 2015-03-04 | 江苏科技大学 | 一种利用臭氧处理改善氮化钛陶瓷涂层生物活性的方法 |
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- 2008-04-15 JP JP2010504622A patent/JP2010531156A/ja active Pending
- 2008-04-15 CN CN200880013438A patent/CN101677536A/zh active Pending
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CN102090392A (zh) * | 2011-01-14 | 2011-06-15 | 浙江大学 | 一种季胺化的可降解抗菌剂的制备方法 |
CN102090392B (zh) * | 2011-01-14 | 2013-06-12 | 浙江大学 | 一种季胺化的可降解抗菌剂的制备方法 |
CN104383600A (zh) * | 2014-10-20 | 2015-03-04 | 江苏科技大学 | 一种利用臭氧处理改善氮化钛陶瓷涂层生物活性的方法 |
CN104383600B (zh) * | 2014-10-20 | 2016-01-13 | 江苏科技大学 | 一种利用臭氧处理改善氮化钛陶瓷涂层生物活性的方法 |
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JP2010531156A (ja) | 2010-09-24 |
EP2160097A2 (en) | 2010-03-10 |
US20100178427A1 (en) | 2010-07-15 |
US8591994B2 (en) | 2013-11-26 |
KR20100022018A (ko) | 2010-02-26 |
WO2008132045A3 (en) | 2009-06-04 |
WO2008132045A2 (en) | 2008-11-06 |
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