JP2008515820A - アルコキシプロピルイソチアゾリノン、およびその製造方法および使用 - Google Patents
アルコキシプロピルイソチアゾリノン、およびその製造方法および使用 Download PDFInfo
- Publication number
- JP2008515820A JP2008515820A JP2007534990A JP2007534990A JP2008515820A JP 2008515820 A JP2008515820 A JP 2008515820A JP 2007534990 A JP2007534990 A JP 2007534990A JP 2007534990 A JP2007534990 A JP 2007534990A JP 2008515820 A JP2008515820 A JP 2008515820A
- Authority
- JP
- Japan
- Prior art keywords
- dichloro
- alkoxypropylisothiazolinone
- isothiazolin
- resin
- alkoxypropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 13
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- OSZKBWPMEPEYFU-UHFFFAOYSA-N methyl 3-[(3-methoxy-3-oxopropyl)disulfanyl]propanoate Chemical compound COC(=O)CCSSCCC(=O)OC OSZKBWPMEPEYFU-UHFFFAOYSA-N 0.000 claims abstract description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 claims abstract description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000007098 aminolysis reaction Methods 0.000 claims abstract 2
- 238000000576 coating method Methods 0.000 claims description 21
- 239000003755 preservative agent Substances 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- -1 Alkoxypropyl isothiazolinone Chemical compound 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DPNNXXVNRSNXHI-UHFFFAOYSA-N 4,5-dichloro-2-(2-propan-2-yloxypropyl)-1,2-thiazol-3-one Chemical compound CC(C)OC(C)CN1SC(Cl)=C(Cl)C1=O DPNNXXVNRSNXHI-UHFFFAOYSA-N 0.000 claims description 9
- 239000004925 Acrylic resin Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000002335 preservative effect Effects 0.000 claims description 9
- FZJPWYQAEZQCON-UHFFFAOYSA-N 2-(2-butoxypropyl)-4,5-dichloro-1,2-thiazol-3-one Chemical compound CCCCOC(C)CN1SC(Cl)=C(Cl)C1=O FZJPWYQAEZQCON-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- WLLPWTDYFMIHJJ-UHFFFAOYSA-N 4,5-dichloro-2-(2-methoxypropyl)-1,2-thiazol-3-one Chemical group COC(C)CN1SC(Cl)=C(Cl)C1=O WLLPWTDYFMIHJJ-UHFFFAOYSA-N 0.000 claims description 5
- 241000588724 Escherichia coli Species 0.000 claims description 5
- 239000000498 cooling water Substances 0.000 claims description 5
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical group COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YYSDNJSAYZUFLN-UHFFFAOYSA-N 2-[3-[2-(2,4,5-trichlorophenoxy)ethoxy]propyl]-1,2-thiazol-3-one Chemical compound ClC1=CC(=C(OCCOCCCN2SC=CC2=O)C=C1Cl)Cl YYSDNJSAYZUFLN-UHFFFAOYSA-N 0.000 claims description 3
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 claims description 3
- LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 claims description 3
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 claims description 3
- VHYUNSUGCNKWSO-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-amine Chemical compound CC(C)OCCCN VHYUNSUGCNKWSO-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 3
- XPLSDXJBKRIVFZ-UHFFFAOYSA-L copper;prop-2-enoate Chemical compound [Cu+2].[O-]C(=O)C=C.[O-]C(=O)C=C XPLSDXJBKRIVFZ-UHFFFAOYSA-L 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims 2
- BRJHFJBCJQNWEQ-UHFFFAOYSA-N 2-[3-(2-methoxyethoxy)propyl]-1,2-thiazol-3-one Chemical group COCCOCCCN1SC=CC1=O BRJHFJBCJQNWEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000006231 alkoxy propyl group Chemical group 0.000 claims 1
- 239000002519 antifouling agent Substances 0.000 abstract description 4
- 239000003973 paint Substances 0.000 abstract description 2
- 239000003899 bactericide agent Substances 0.000 abstract 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- ZSZSVDFDLRCOBM-UHFFFAOYSA-N 4,5-dichloro-2-[3-(2-methoxyethoxy)propyl]-1,2-thiazol-3-one Chemical compound COCCOCCCN1SC(Cl)=C(Cl)C1=O ZSZSVDFDLRCOBM-UHFFFAOYSA-N 0.000 description 5
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- UOVXUJIHCPXTSB-UHFFFAOYSA-N 4,5-dichloro-2-(2-ethoxypropyl)-1,2-thiazol-3-one Chemical compound CCOC(C)CN1SC(Cl)=C(Cl)C1=O UOVXUJIHCPXTSB-UHFFFAOYSA-N 0.000 description 3
- QNQZKBZVMITXKK-UHFFFAOYSA-N N-ethoxy-2-[[[3-(ethoxyamino)-3-oxopropyl]disulfanyl]methyl]pentanamide Chemical group O(CC)NC(CCSSCC(C(=O)NOCC)CCC)=O QNQZKBZVMITXKK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 3
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 3
- 229940112669 cuprous oxide Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- FWGBHTPPUUZGDJ-UHFFFAOYSA-N 5-ethoxy-2-[[[3-oxo-3-(phenoxyamino)propyl]disulfanyl]methyl]-N-phenoxypentanamide Chemical group O(C1=CC=CC=C1)NC(CCSSCC(C(=O)NOC1=CC=CC=C1)CCCOCC)=O FWGBHTPPUUZGDJ-UHFFFAOYSA-N 0.000 description 2
- PDVYHKMVJFIECK-UHFFFAOYSA-N 5-ethoxy-N-methoxy-2-[[[3-(methoxyamino)-3-oxopropyl]disulfanyl]methyl]pentanamide Chemical group CONC(CCSSCC(C(=O)NOC)CCCOCC)=O PDVYHKMVJFIECK-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LQFGIQGGVGHDCL-UHFFFAOYSA-N N-butoxy-2-[[[3-(butoxyamino)-3-oxopropyl]disulfanyl]methyl]pentanamide Chemical group C(CCC)ONC(CCSSCC(C(=O)NOCCCC)CCC)=O LQFGIQGGVGHDCL-UHFFFAOYSA-N 0.000 description 2
- YJSTTXJBBCDWNA-UHFFFAOYSA-N N-methoxy-2-[[[3-(methoxyamino)-3-oxopropyl]disulfanyl]methyl]pentanamide Chemical compound O(C)NC(CCSSCC(C(=O)NOC)CCC)=O YJSTTXJBBCDWNA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000009360 aquaculture Methods 0.000 description 2
- 244000144974 aquaculture Species 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 description 1
- PIORWMKBKAOYMZ-UHFFFAOYSA-N 2-methyl-N-[(propanoylamino)disulfanyl]-5-propan-2-yloxypentanamide Chemical group C(C)(C)OCCCC(C(=O)NSSNC(CC)=O)C PIORWMKBKAOYMZ-UHFFFAOYSA-N 0.000 description 1
- WQFCFMPMUNOOTQ-UHFFFAOYSA-N 3-(2-phenoxyethoxy)propan-1-amine Chemical group NCCCOCCOC1=CC=CC=C1 WQFCFMPMUNOOTQ-UHFFFAOYSA-N 0.000 description 1
- GJXCLGKEGAGUQC-UHFFFAOYSA-N 3-[(3-amino-3-oxopropyl)disulfanyl]propanamide Chemical compound NC(=O)CCSSCCC(N)=O GJXCLGKEGAGUQC-UHFFFAOYSA-N 0.000 description 1
- SHIIPDUYJFVFAL-UHFFFAOYSA-N 3-[[3-oxo-3-(propan-2-yloxyamino)propyl]disulfanyl]-n-propan-2-yloxypropanamide Chemical group CC(C)ONC(=O)CCSSCCC(=O)NOC(C)C SHIIPDUYJFVFAL-UHFFFAOYSA-N 0.000 description 1
- AGXWKEPOTNVEKH-UHFFFAOYSA-N 4,5-dichloro-2-[2-(2,2-dimethoxyethoxy)propyl]-1,2-thiazol-3-one Chemical compound ClC=1C(N(SC1Cl)CC(C)OCC(OC)OC)=O AGXWKEPOTNVEKH-UHFFFAOYSA-N 0.000 description 1
- IPXBRJVVMFFAPP-UHFFFAOYSA-N 4,5-dichloro-2-[2-(2,2-diphenoxyethoxy)propyl]-1,2-thiazol-3-one Chemical compound ClC=1C(N(SC1Cl)CC(C)OCC(OC1=CC=CC=C1)OC1=CC=CC=C1)=O IPXBRJVVMFFAPP-UHFFFAOYSA-N 0.000 description 1
- CGBYMFJTQIKDBX-UHFFFAOYSA-N 4,5-dichloro-2-[3-(2-phenoxyethoxy)propyl]-1,2-thiazol-3-one Chemical group O=C1C(Cl)=C(Cl)SN1CCCOCCOC1=CC=CC=C1 CGBYMFJTQIKDBX-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000237519 Bivalvia Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000238586 Cirripedia Species 0.000 description 1
- JYDZLLKBJBFIBP-UHFFFAOYSA-N ClC=1CN(SC1Cl)CC(C)OCC Chemical compound ClC=1CN(SC1Cl)CC(C)OCC JYDZLLKBJBFIBP-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000251555 Tunicata Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 235000020639 clam Nutrition 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LPUCKLOWOWADAC-UHFFFAOYSA-M tributylstannyl 2-methylprop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C(C)=C LPUCKLOWOWADAC-UHFFFAOYSA-M 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000011787 zinc oxide Substances 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
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Abstract
【選択図】なし
Description
本発明の目的は、海洋防汚コーティングおよび防腐剤の製造に使用して、上述した先行技術の需要を補償する、アルコキシプロピルイソチアゾリノン、およびその製造方法を提供することである。
であるもの:
式中、RはCH3、CH2CH3、CH(CH3)2、CH2CH2CH2CH3、CH2CH2OCH3またはCH2CH2OC6H5Clである。
スターラー、凝縮器および温度計を備えた500mlの三つ口フラスコに、200mlの10%(重量%、以下同様)NaHCO3溶液および21.7g(0.25mo1) のアクリル酸メチルを連続的に添加し、次に系を-5〜10℃に冷却した。この温度を保ちながら、冷却した多硫化ナトリウム(0.19mol、Na2Sによる計算)溶液を0.5〜2時間滴下した。滴下後、氷水浴を外した。混合物を室温で5〜6時間静置した。その後、反応を終了した。得られた混合物を静置し、2層に分離した。水層を除いた。120ml(lmol/L)のNa2SO3溶液を油層に加えた。次に混合物を、反応が終了するまで、50℃ の温度で2〜5時間連続的に反応させた。得られた混合物を再度静置し、層分離した。その後、水層を除き、油層を水洗した。真空蒸留により、26.8gの淡黄色油状物質を得たが、収率は89.3%であり、沸点は182〜185℃/7mmHgである。
スターラー、凝縮器および温度計を備えた500mlの三つ口フラスコに、26.7g(0.3mol)のγ-メトキシプロピルアミン、2.5mlのトリエチルアミンを続けて添加し、反応系の温度を-5〜5℃に制御し維持した。次に、前の工程で製造した23.8g(0.1mo1)のβ-ジチオジプロピオン酸ジメチルを0.5〜1.5時間滴下した。滴下後、氷水浴を外した。反応は室温で24時間静置し、その後、反応を終了した。金色の固体を得た。それから真空濾過により、淡黄色の固体生成物を得た。乾燥後、無水アルコールで再結晶した。24.1gの白色小片結晶を得たが、収率は68.4%であり、沸点は103.3〜105.1℃である。
スターラー、凝縮器および温度計を備えた250mlの三つ口フラスコに、175mlの酢酸エチルおよび18.0g(0.05mo1)のN,N'-ジエトキシプロピルジチオジプロピオンアミドを連続的に添加する。系の温度を-10〜5℃に保ちながら、40.0g(0.3mo1)の塩化スルフリルを3時間滴下した。この温度で反応を3時間継続し、その後反応系の温度を室温までゆっくりと上昇させた。反応が終了するまで、混合物を水浴中30〜35℃でさらに3時間反応させた。得られた溶液に50mlの水を添加した後、3分間振とうした。得られた混合物を静置し、2層に分離した。有機相を無水硫酸マグネシウム(15.0g)で15分間乾燥した後、濾過した。スピン蒸発計で減圧して濾液から溶媒を除去した。15.4gの黄色の濃厚液体が得られたが、一次収率は63.9%であり、カラムで分離した純生成物の収率は56.6%である。
アルコキシプロピルイソチアゾリノンは、海洋防汚コーティングの防汚剤として使用される。
本発明の6種のアルコキシプロピルイソチアゾリノンの最低静菌濃度を、チューブ二重希釈法(tube double dilution method)で測定する。径18×180mmのチューブに、5mlの無菌培地を加え、その後、大腸菌の懸濁液50μlを注入して、菌濃度107cfu/mlの牛抽出ペプトン培養液を調製した後、4,5-ジクロロ-2-イソプロポキシプロピル-4-イソチアゾリン-3-オンを2μg/ml、4μg/ml、8μg/ml、16μg/ml、32μg/mlの濃度で含有するテトラヒドロフラン溶液50μ1をそれぞれ添加した。37℃の一定温度で24時間培養した後、大腸菌に対する4,5-ジクロロ-2-イソプロポキシプロピル-4-イソチアゾリン-3-オンの最低静菌濃度を測定した。結果は8μg/mlである(cfuはコロニー形成単位であり、1cfuは、培養後に寒天板上に1つのコロニーが形成されたことを言う)。
Claims (10)
- 請求項1に記載のアルコキシプロピルイソチアゾリノンの製造方法であって、該方法が以下の反応工程:多硫化ナトリウムをアクリル酸メチルと反応させて、ジチオジプロピオン酸ジメチルを得、その後、アルコキシプロピルアミンでアミノ分解してN,N'-ジアルコキシプロピルジチオ-ジプロピオンアミドを得、次に塩化スルフリルと反応させてアルコキシプロピルイソチアゾリノンを得る工程を含むことを特徴とする、方法。
- 請求項2の方法であって、アルコキシプロピルイソチアゾリノンが4,5-ジクロロ-2-メトキシプロピル-4-イソチアゾリン-3-オン、4,5-ジクロロ-2-エトキシプロピル-4-イソチアゾリン-3-オン、4,5-ジクロロ-2-イソプロポキシプロピル-4-イソチアゾリン-3-オン、4,5-ジクロロ-2-ブトキシプロピル-4-イソチアゾリン-3-オン、4,5-ジクロロ-2-メトキシエトキシプロピル-4-イソチアゾリン-3-オン、または4,5-ジクロロ-2-クロロフェノキシエトキシプロピル-4-イソチアゾリン-3-オンであることを特徴とする、方法。
- 請求項2の方法であって、アルコキシプロピルアミンがγ-メトキシプロピルアミン、γ-エトキシプロピルアミン、γ-イソプロポキシプロピルアミン、γ-ブトキシプロピルアミン、γ-メトキシエトキシプロピルアミンまたはγ-フェノキシエトキシプロピルアミンであることを特徴とする、方法。
- 海洋防汚コーティングを製造するために用いられることを特徴とする、請求項1のアルコキシプロピルイソチアゾリノン。
- 海洋防汚コーティングが、樹脂溶液、可塑剤、1以上のフィラーおよび1以上の請求項1のアルコキシプロピルイソチアゾリノン、それぞれ20〜60、1〜20、1〜30および1〜50重量%で構成され、ここで樹脂溶液の樹脂が、アクリル酸樹脂、塩化ゴム、ジアクリル酸亜鉛樹脂およびアクリル酸銅樹脂から選択される1以上であり、溶媒が酢酸エチル、酢酸ブチル、キシレン、トルエンおよびブタノールから選択される1以上であり、樹脂溶液の濃度が20%〜60%の範囲内であることを特徴とする、海洋防汚コーティング。
- 防腐剤として使用されることを特徴とする、請求項1のアルコキシプロピルイソチアゾリノン。
- 防腐剤によって阻害される腐敗物が黄色ブドウ球菌、大腸菌またはサッカロマイセス・セレヴィシエ(saccharomyces cerevisiae)であることを特徴とする、請求項7のアルコキシプロピルイソチアゾリノン。
- 産業冷却水の防腐剤として使用されることを特徴とする、請求項1のアルコキシプロピルイソチアゾリノン。
- 農業用途の防腐剤として使用される、ことを特徴とする、請求項1のアルコキシプロピルイソチアゾリノン。
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CNB2004100359580A CN1317270C (zh) | 2004-10-10 | 2004-10-10 | 烷氧乙氧基丙基异噻唑啉酮及其制备方法和应用 |
CN200410035990.9 | 2004-10-16 | ||
CN 200410035989 CN1273457C (zh) | 2004-10-16 | 2004-10-16 | 烷氧基丙基异噻唑啉酮及其制备方法和应用 |
CN 200410035990 CN1290415C (zh) | 2004-10-16 | 2004-10-16 | 烷氧基丙基异噻唑啉酮作为杀菌剂的应用 |
CN200410035989.6 | 2004-10-16 | ||
PCT/CN2005/001629 WO2006037274A1 (fr) | 2004-10-10 | 2005-09-30 | Isothiazolinone alcoxypropylique, son procede de preparation et son utilisation |
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WO2006037274A1 (fr) | 2006-04-13 |
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JP4789950B2 (ja) | 2011-10-12 |
DK1810966T3 (da) | 2012-07-30 |
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