JP5670882B2 - アミノアルコールおよび水系システム用の殺生剤組成物 - Google Patents
アミノアルコールおよび水系システム用の殺生剤組成物 Download PDFInfo
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- JP5670882B2 JP5670882B2 JP2011509540A JP2011509540A JP5670882B2 JP 5670882 B2 JP5670882 B2 JP 5670882B2 JP 2011509540 A JP2011509540 A JP 2011509540A JP 2011509540 A JP2011509540 A JP 2011509540A JP 5670882 B2 JP5670882 B2 JP 5670882B2
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- JP
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- Prior art keywords
- amino
- methyl
- ethyl
- composition according
- hexanol
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 69
- 230000003115 biocidal effect Effects 0.000 title claims description 46
- 239000003139 biocide Substances 0.000 title claims description 39
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 4
- 239000012530 fluid Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000005555 metalworking Methods 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- -1 amino alcohol compound Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 claims description 13
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- PDNZJLMPXLQDPL-UHFFFAOYSA-N (1-aminocyclopentyl)methanol Chemical compound OCC1(N)CCCC1 PDNZJLMPXLQDPL-UHFFFAOYSA-N 0.000 claims description 7
- HUHGPYXAVBJSJV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol Chemical compound OCCN1CN(CCO)CN(CCO)C1 HUHGPYXAVBJSJV-UHFFFAOYSA-N 0.000 claims description 7
- ASNUCXNSIMBBMA-UHFFFAOYSA-N 2-amino-2-ethylheptan-1-ol Chemical compound CCCCCC(N)(CC)CO ASNUCXNSIMBBMA-UHFFFAOYSA-N 0.000 claims description 7
- KIOCABJEBRVQNM-UHFFFAOYSA-N 2-amino-2-methylhexan-1-ol Chemical compound CCCCC(C)(N)CO KIOCABJEBRVQNM-UHFFFAOYSA-N 0.000 claims description 7
- PUHONNHQBPIIJT-UHFFFAOYSA-N 2-amino-2-propylhexan-1-ol Chemical compound CCCCC(N)(CO)CCC PUHONNHQBPIIJT-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- QKGFFCDDDREERJ-UHFFFAOYSA-N (1-aminocyclooctyl)methanol Chemical compound OCC1(N)CCCCCCC1 QKGFFCDDDREERJ-UHFFFAOYSA-N 0.000 claims description 6
- PDVDVCSVYXZLOI-UHFFFAOYSA-N 2-amino-2-ethylpentan-1-ol Chemical compound CCCC(N)(CC)CO PDVDVCSVYXZLOI-UHFFFAOYSA-N 0.000 claims description 6
- WYHLKHURMRDRTG-UHFFFAOYSA-N 2-amino-2-methyloctan-1-ol Chemical compound CCCCCCC(C)(N)CO WYHLKHURMRDRTG-UHFFFAOYSA-N 0.000 claims description 6
- WAQCLDRCXNFRBI-UHFFFAOYSA-N 2-amino-2-phenylpropan-1-ol Chemical compound OCC(N)(C)C1=CC=CC=C1 WAQCLDRCXNFRBI-UHFFFAOYSA-N 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 4
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- AHZILZSKKSPIKM-UHFFFAOYSA-N 3-aminooctan-4-ol Chemical compound CCCCC(O)C(N)CC AHZILZSKKSPIKM-UHFFFAOYSA-N 0.000 claims description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
- 150000001414 amino alcohols Chemical class 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000813 microbial effect Effects 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 8
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-UHFFFAOYSA-N 0.000 description 7
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 6
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 6
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 5
- GUQMDNQYMMRJPY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazolidine Chemical compound CC1(C)COCN1 GUQMDNQYMMRJPY-UHFFFAOYSA-N 0.000 description 5
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 5
- ZRCMGIXRGFOXNT-UHFFFAOYSA-N 7a-ethyl-1,3,5,7-tetrahydro-[1,3]oxazolo[3,4-c][1,3]oxazole Chemical compound C1OCN2COCC21CC ZRCMGIXRGFOXNT-UHFFFAOYSA-N 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical class CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 5
- GQHVWDKJTDUZRP-UHFFFAOYSA-N 4-(2-nitrobutyl)morpholine Chemical compound CCC([N+]([O-])=O)CN1CCOCC1 GQHVWDKJTDUZRP-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 4
- MIFZZKZNMWTHJK-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)morpholine Chemical compound C1COCCN1CN1CCOCC1 MIFZZKZNMWTHJK-UHFFFAOYSA-N 0.000 description 3
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000005553 drilling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CNRYJIAFTZIABA-UHFFFAOYSA-N (1-aminocyclododecyl)methanol Chemical compound OCC1(N)CCCCCCCCCCC1 CNRYJIAFTZIABA-UHFFFAOYSA-N 0.000 description 2
- YCUBUBCODJSBIC-UHFFFAOYSA-N (1-aminocycloheptyl)methanol Chemical compound OCC1(N)CCCCCC1 YCUBUBCODJSBIC-UHFFFAOYSA-N 0.000 description 2
- RNMJPIYVCVKBMG-UHFFFAOYSA-N (1-aminocyclononyl)methanol Chemical compound OCC1(N)CCCCCCCC1 RNMJPIYVCVKBMG-UHFFFAOYSA-N 0.000 description 2
- SWZDYPQVZUVWPA-UHFFFAOYSA-N (1-aminocycloundecyl)methanol Chemical compound OCC1(N)CCCCCCCCCC1 SWZDYPQVZUVWPA-UHFFFAOYSA-N 0.000 description 2
- USOLRVZGBJWYTO-UHFFFAOYSA-N (1-nitrocyclohexyl)methanol Chemical compound OCC1([N+]([O-])=O)CCCCC1 USOLRVZGBJWYTO-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 2
- XOILGBPDXMVFIP-UHFFFAOYSA-N 1-(diiodomethylsulfonyl)-4-methylbenzene Chemical compound CC1=CC=C(S(=O)(=O)C(I)I)C=C1 XOILGBPDXMVFIP-UHFFFAOYSA-N 0.000 description 2
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 2
- INUKVBVIJJTDCU-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-2,4,6-trimethyl-1,3,5-triazinan-1-yl]ethanol Chemical compound CC1N(CCO)C(C)N(CCO)C(C)N1CCO INUKVBVIJJTDCU-UHFFFAOYSA-N 0.000 description 2
- GSXBEQWNPZIBLZ-UHFFFAOYSA-N 2-amino-2-butylheptan-1-ol Chemical compound CCCCCC(N)(CO)CCCC GSXBEQWNPZIBLZ-UHFFFAOYSA-N 0.000 description 2
- RDEFHGRTIKHVTK-UHFFFAOYSA-N 2-amino-2-butylhexan-1-ol Chemical compound CCCCC(N)(CO)CCCC RDEFHGRTIKHVTK-UHFFFAOYSA-N 0.000 description 2
- PZAFLOVABHSEPL-UHFFFAOYSA-N 2-amino-2-butylnonan-1-ol Chemical compound CCCCCCCC(N)(CO)CCCC PZAFLOVABHSEPL-UHFFFAOYSA-N 0.000 description 2
- SXUDFXVTAJOHJR-UHFFFAOYSA-N 2-amino-2-butyloctan-1-ol Chemical compound CCCCCCC(N)(CO)CCCC SXUDFXVTAJOHJR-UHFFFAOYSA-N 0.000 description 2
- OCHKJTXOYWDPSK-UHFFFAOYSA-N 2-amino-2-ethyldecan-1-ol Chemical compound CCCCCCCCC(N)(CC)CO OCHKJTXOYWDPSK-UHFFFAOYSA-N 0.000 description 2
- AQVAKYWHEGYKEE-UHFFFAOYSA-N 2-amino-2-ethylhexan-1-ol Chemical compound CCCCC(N)(CC)CO AQVAKYWHEGYKEE-UHFFFAOYSA-N 0.000 description 2
- GQTIGVABHYQSNA-UHFFFAOYSA-N 2-amino-2-ethylnonan-1-ol Chemical compound CCCCCCCC(N)(CC)CO GQTIGVABHYQSNA-UHFFFAOYSA-N 0.000 description 2
- YRJHDFPUSLCJBF-UHFFFAOYSA-N 2-amino-2-ethyloctan-1-ol Chemical compound CCCCCCC(N)(CC)CO YRJHDFPUSLCJBF-UHFFFAOYSA-N 0.000 description 2
- XVLZSRHRQSCUDP-UHFFFAOYSA-N 2-amino-2-methyldecan-1-ol Chemical compound CCCCCCCCC(C)(N)CO XVLZSRHRQSCUDP-UHFFFAOYSA-N 0.000 description 2
- BUSOXNRPZDZCKM-UHFFFAOYSA-N 2-amino-2-methylheptan-1-ol Chemical compound CCCCCC(C)(N)CO BUSOXNRPZDZCKM-UHFFFAOYSA-N 0.000 description 2
- LAXOIQQEPAILKS-UHFFFAOYSA-N 2-amino-2-methylnonan-1-ol Chemical compound CCCCCCCC(C)(N)CO LAXOIQQEPAILKS-UHFFFAOYSA-N 0.000 description 2
- MLNLPPJWJYOGAR-UHFFFAOYSA-N 2-amino-2-methylundecan-1-ol Chemical compound CCCCCCCCCC(C)(N)CO MLNLPPJWJYOGAR-UHFFFAOYSA-N 0.000 description 2
- YZEGBQTVZVXZOC-UHFFFAOYSA-N 2-amino-2-pentylheptan-1-ol Chemical compound CCCCCC(N)(CO)CCCCC YZEGBQTVZVXZOC-UHFFFAOYSA-N 0.000 description 2
- LHOCZVIDCHAIOJ-UHFFFAOYSA-N 2-amino-2-pentyloctan-1-ol Chemical compound CCCCCCC(N)(CO)CCCCC LHOCZVIDCHAIOJ-UHFFFAOYSA-N 0.000 description 2
- IJXJGQCXFSSHNL-UHFFFAOYSA-N 2-amino-2-phenylethanol Chemical compound OCC(N)C1=CC=CC=C1 IJXJGQCXFSSHNL-UHFFFAOYSA-N 0.000 description 2
- CWPUPQHUJOQTFL-UHFFFAOYSA-N 2-amino-2-propyldecan-1-ol Chemical compound CCCCCCCCC(N)(CO)CCC CWPUPQHUJOQTFL-UHFFFAOYSA-N 0.000 description 2
- ZIABYOVGWRVKEO-UHFFFAOYSA-N 2-amino-2-propylheptan-1-ol Chemical compound CCCCCC(N)(CO)CCC ZIABYOVGWRVKEO-UHFFFAOYSA-N 0.000 description 2
- QQKGTPSMBFILQZ-UHFFFAOYSA-N 2-amino-2-propylnonan-1-ol Chemical compound CCCCCCCC(N)(CO)CCC QQKGTPSMBFILQZ-UHFFFAOYSA-N 0.000 description 2
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- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- XPGDDCOXMUFUCB-UHFFFAOYSA-N 4,4'-(ethyl-2-nitropropane-1,3-diyl)bismorpholine Chemical compound C1COCCN1CC([N+]([O-])=O)(CC)CN1CCOCC1 XPGDDCOXMUFUCB-UHFFFAOYSA-N 0.000 description 2
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- KCWRPJRGLLZKRW-UHFFFAOYSA-N 5,5-dibromo-3-octyl-1,2-thiazol-4-one Chemical compound CCCCCCCCC1=NSC(Br)(Br)C1=O KCWRPJRGLLZKRW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 2
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- 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
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
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- 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
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
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- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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Description
本件は、米国仮出願第61/053,408号(2008年5月15日出願)および米国仮出願第61/073,894号(2008年6月19日出願)の利益を主張する。
本発明は、水系システム,例えば金属作動流体において使用するための殺生物組成物、使用方法、および新規なアミノアルコール化合物に関する。
短鎖アミノアルコールは、その腐食防止、中和ならびにpHの調整およびメンテナンスの特性によって、広範な用途で商業的に使用されている。1つのこのような用途は金属作動流体におけるものである。
一側面において、本発明は、殺生物組成物を提供する。該組成物は、殺生物剤および非殺生物性の1級アミノアルコール化合物を含み、該1級アミノアルコール化合物は、式(I):
のものである。
本発明は、殺生剤および以下に定義する式(I)のアミノアルコールを含む殺生物組成物、ならびに水系システムにおける微生物の生育の阻害のためのその使用を提供する。本発明者らは、少なくとも5個の炭素原子を含有する式(I)の1級アミノアルコールが、自身は殺生物性ではないが、驚くべきことに、種々の媒体中で使用される殺生剤の性能を向上させることを見出した。結果として、本発明は、種々の用途における殺生剤の使用の低減、これによる材料、輸送および貯蔵のコストの低減を可能にする。
R1およびR3は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリール(好ましくはフェニル)であり、またはR1、R3およびこれらが付いている炭素がシクロアルキル環を形成し;
R2およびR4は、各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR2、R4およびこれらが付いている炭素がシクロアルキル環を形成し、但しR2およびR4が一緒に3個以上の炭素原子を含有することを条件とし;そして
R5は、不存在またはC1〜C10脂肪族アルキレン(架橋アルキル)、アリーレン(好ましくはフェニル)、−アリーレン−アルキレン−、または−アルキレン−アリーレン−(例えば、ベンジル、フェネチル等)であり;
ここでアルキル、シクロアルキル、アルキレン、アリール、およびアリーレンは任意にアルキルまたはフェニルで置換されている。)
のものである。式(I)の化合物は、少なくとも5個の炭素原子を含有する。幾つかの態様において、化合物は、少なくとも6個の炭素原子を含有する。更に好ましい態様において、化合物は13個以下の炭素原子を含有する。アミノアルコールは、式(I)の2種以上の化合物の混合物の形であることができる。
の化合物が挙げられる。
例A:1−アミノシクロヘキシルメタノール(AcyHM)の調製
2リットルの三口フラスコ(マグネチックスターラー、窒素雰囲気生成装置、熱電対制御加熱マントルおよび添加漏斗を備える)にニトロシクロヘキサン(521g,4.04mol)を入れる。トリエチルアミン触媒(10.0mL)を添加し、そして黄色混合物を、加熱マントルを用いて55℃まで加温する。添加漏斗を介して、水性ホルムアルデヒド(37wt%,330mL,4.4mol)を90分間に亘って滴下添加する。反応は極めて穏やかに発熱し、添加中に60℃まで加温される。全てのホルムアルデヒドを添加した後、反応混合物を60℃で更に2時間保持し、分液漏斗に注ぎ入れ、そして1晩冷却/相分離させる。下部のオレンジ色の生成物層を回収(750.8g,溶解した水を含有する)し、そしてGC分析は、96.9%の純度を、約1.7%のニトロシクロヘキサンおよび1.4%のトリエチルアミンとともに示す。生成物は、更なる精製を伴わずに使用する。
同一配合物(表1)を、例のアミン(A,B,C,D,E,F)の各々で調製し、そして対照(AMP)と比較する。トリアジン3殺生剤(Arch Chemicalより(78%活性トリアジン))を流体濃縮物に1.5%で添加する。流体濃縮物を約5%の程度でミシガン湖の水道水中に希釈し、活性アミノアルコール濃度は希釈時に約0.3%であり、そして活性トリアジン殺生剤用量は約0.058%である。これらの流体を、先の例で記載したのと同じ微生物チャレンジ試験に供する。バクテリア生育および菌類生育の結果を図3および4に示す。本発明の化合物の幾つかを含有する流体は、バクテリア生育に対して耐性であるが、特に菌類生育は、比較AMPを伴うものよりも顕著に長い。
表1中のベース配合物を用いて、AMPとの比較で、BIOBANTM BIT 20との組合せで、本発明のアミンの幾つかを評価する(例A,C,E,F)。BIOBANTM BIT 20は、Dow Chemical Companyより提供され、20%活性ベンズイソチアゾリノン(BIT)を含有する。BITは、MWFにおいては有効な殺生剤であるとは知られていないが、これはホルムアルデヒドから形成されておらず、取扱いまたは使用の間にホルムアルデヒドを放出しないため望ましい。BIOBANTM BIT 20は、1.8%で流体濃縮物に添加し、約0.018%の活性BITを5%希釈で与える。微生物試験の結果を図5および6に記載する。本発明の化合物は、バクテリアおよび菌類の両者に対するBITの性能において、AMP(比較のアミノアルコール)を有する流体と比べて顕著な改善を与える。
本発明は以下の態様を有する。
[1] 殺生物剤;ならびに
式(I):
R 1 およびR 3 は、各々独立にH、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキル、もしくはアリールであり、またはR 1 、R 3 およびこれらが付いている炭素がシクロアルキル環を形成し;
R 2 およびR 4 は各々独立にH、直鎖もしくは分岐鎖のアルキル、シクロアルキル、シクロアルキル−アルキル、アリール、アリール−アルキルであり、またはR 2 、R 4 およびこれらが付いている炭素がシクロアルキル環を形成し、但しR 2 およびR 4 が共に3個以上の炭素原子を含有することを条件とし;そして
R 5 は、不存在またはC 1 〜C 10 アルキレン、アリーレン、−アリーレン−アルキレン−、または−アルキレン−アリーレン−であり;
ここでアルキル、シクロアルキル、アルキレン、アリール、およびアリーレンは任意にアルキルまたはフェニルで置換されている。)
の1級アミノアルコール化合物;
を含む、殺生物組成物。
[2] 式(I)の化合物が、13個以下の炭素原子を含む、上記[1]に記載の組成物。
[3] 2−アミノ−2−メチル−1−プロパノール、2−アミノ−1−エタノール、1−アミノ−2−プロパノール、ビス(2−ヒドロキシプロピル)アミン、トリス(2−ヒドロキシプロピル)アミン、ビス(2−ヒドロキシエチル)アミン、トリス(2−ヒドロキシエチル)アミン、2−(2−アミノエトキシ)エタノール、および3−アミノ−4−オクタノールからなる群から選択される1種以上の化合物を更に含む、上記[1]〜[2]に記載の組成物。
[4] 殺生物剤が、ホルムアルデヒド系または非ホルムアルデヒド系である、上記[1]〜[3]に記載の組成物。
[5] 殺生物剤が、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート(THPS)、1,3,5−トリス(2−ヒドロキシエチル)−s−トリアジン、ヨードプロピニルブチルカルバメート、1,2−ベンズイソチアゾリン−3−オン、4,4−ジメチルオキサゾリジン、7−エチルビシクロオキサゾリジン、4−(2−ニトロブチル)−モルホリンと4,4’−(2−エチル−2−ニトロトリメチレン)ジモルホリンとの組合せ、2−メチル−4−イソチアゾリン−3−オン、5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとの組合せ、2−ブロモ−2−ニトロ−1,3−プロパンジオール、オクチルイソチアゾリノン、ジクロロ−オクチルイソチアゾリノン、ジブロモ−オクチルイソチアゾリノン、フェノール物,例えばo−フェニルフェノールおよびp−クロロ−m−クレゾールならびにその対応するナトリウムおよび/またはカリウム塩、ナトリウムピリチオン、ジンクピリチオン、n−ブチルベンズイソチアゾリノン、1−(3−クロロアリル)−3,5,7−トリアザ−1−アゾニアアダマンタンクロリド、クロロタロニル、カルベンダジム、ジヨードメチルトリルスルホン、トリメチル−1,3,5−トリアジン−1,3,5−トリエタノール、2,2−ジブロモ−3−ニトリロプロピオンアミド、グルタルアルデヒド、N,N’−メチレン−ビス−モルホリン、エチレンジオキシメタノール、フェノキシエタノール、テトラメチロールアセチレンジウレア、ジチオカルバメート、2,6−ジメチル−m−ジオキサン−4−オールアセテート、ジメチロール−ジメチル−ヒダントイン、トリス(ヒドロキシメチル)ニトロメタン、二環式オキサゾリジン、ならびにこれらの2種以上の混合物からなる群から選択される、上記[1]〜[4]に記載の組成物。
[6] 殺生物剤が、テトラキス(ヒドロキシメチル)ホスホニウムスルフェート(THPS)、1,3,5−トリス(2−ヒドロキシエチル)−s−トリアジン、1,2−ベンズイソチアゾリン−3−オン、4,4−ジメチルオキサゾリジンおよび7−エチルビシクロオキサゾリジン、ヨードプロピニルブチルカルバメート、ナトリウムピリチオン、オクチルイソチアゾリノン、5−クロロ−2−メチル−4−イソチアゾリン−3−オンと2−メチル−4−イソチアゾリン−3−オンとの組合せ、フェノール物、グルタルアルデヒド、2,2−ジブロモ−3−ニトリロプロピオンアミド(DBNPA)、1−(3−クロロアリル)−3,5,7−トリアザ−1−アゾニアアダマンタンクロリド、N,N’−メチレン−ビス−モルホリン、ならびにこれらの2種以上の混合物からなる群から選択される、上記[1]〜[5]に記載の組成物。
[7] R 5 が不存在である、上記[1]〜[6]に記載の組成物。
[8] アミノアルコール化合物が、式(II):
[9] R 2 およびR 4 が共に11個以下の炭素原子を含有する、上記[8]に記載の組成物。
[10] R 2 およびR 4 が各々独立に直鎖アルキルである、上記[8]または[9]に記載の組成物。
[11] R 2 およびR 4 のうち、一方がHであり、そして他方が直鎖アルキルである、上記[8]〜[9]に記載の組成物。
[12] R 2 およびR 4 が、これらが付いている炭素と共にシクロアルキル環を形成する、上記[8]〜[9]に記載の組成物。
[13] R 2 およびR 4 のうち、一方がCH 3 であり、そして他方がアリールである、上記[8]〜[9]に記載の組成物。
[14] アミノアルコール化合物が:2−アミノ−2−メチル−1−ヘキサノール、2−アミノ−2−エチル−1−ペンタノール、2−アミノ−2−メチル−1−ヘプタノール、2−アミノ−2−エチル−1−ヘキサノール、2−アミノ−2−プロピル−1−ペンタノール、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、2−アミノ−2−プロピル−1−ヘキサノール、2−アミノ−2−メチル−1−ノナノール、2−アミノ−2−エチル−1−オクタノール、2−アミノ−2−プロピル−1−ヘプタノール、2−アミノ−2−ブチル−1−ヘキサノール、2−アミノ−2−メチル−1−デカノール、2−アミノ−2−エチル−1−ノナノール、2−アミノ−2−プロピル−1−オクタノール、2−アミノ−2−ブチル−1−ヘプタノール、2−アミノ−2−メチル−1−ウンデカノール、2−アミノ−2−エチル−1−デカノール、2−アミノ−2−プロピル−1−ノナノール、2−アミノ−2−ブチル−1−オクタノール、2−アミノ−2−ペンチル−1−ヘプタノール、2−アミノ−2−メチル−1−ドデカノール、2−アミノ−2−エチル−1−ウンデカノール、2−アミノ−2−プロピル−1−デカノール、2−アミノ−2−ブチル−1−ノナノール、2−アミノ−2−ペンチル−1−オクタノール、(1−アミノシクロペンチル)メタノール、(l−アミノシクロヘキシル)メタノール、(l−アミノシクロヘプチル)メタノール、(1−アミノシクロオクチルメタノール、(1−アミノシクロノニル)メタノール、(1−アミノシクロデシルメタノール,(l−アミノシクロウンデシル)メタノール、(l−アミノシクロドデシル)メタノール、2−アミノ−2−フェニル−1−エタノール、2−アミノ−2−フェニル−1−プロパノール、2−アミノ−2−フェニル−1−ブタノール、およびこれらの混合物からなる群から選択される、上記[1]〜[13]に記載の組成物。
[15] アミノアルコールが、2−アミノ−2−メチル−1−ヘキサノール、2−アミノ−2−エチル−1−ペンタノール、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノール、2−アミノ−2−プロピル−1−ヘキサノール、(1−アミノシクロヘキシル)メタノール、(1−アミノシクロオクチル)メタノール、2−アミノ−2−フェニル−1−プロパノール、(1−アミノシクロペンチル)メタノールおよびこれらの混合物である、上記[1]〜[14]に記載の組成物。
[16] 水系システムにおける微生物の生育を阻害する方法であって、該システムに、上記[1]〜[15]のいずれかに記載の殺生物組成物を有効量添加することを含む、方法。
[17] 水系システムが、金属作動流体である、上記[16]に記載の方法。
[18] 上記[1]〜[15]のいずれかに記載の殺生物組成物を含む、金属作動流体濃縮物。
[19] 上記[1]〜[15]のいずれかに記載の殺生物組成物を含む、金属作動流体。
[20] 水および金属作動濃縮物を含む金属作動流体であって、該金属作動濃縮物が上記[1]〜[15]のいずれかに記載の殺生物組成物を含む、金属作動流体。
[21] 組成物中での微生物の生育が阻害されている組成物であって:水系システム;および上記[1]〜[15]のいずれかに記載の殺生物組成物;を含む、組成物。
[22] 水系システムが、ラテックス、水系塗料、水系コーティング、コーク、接着剤、テープ接合コンパウンド、鉱物スラリー、水冷却システム、パーソナルケア製品、ソープおよび洗剤、殺菌剤、洗浄剤、消毒剤、殺虫剤製品、油田水、ならびに油田用途において使用される水系流体,例えば掘削泥水、破砕流体およびハイドロテスト流体である、上記[21]に記載の組成物。
[23] 水系システムが、金属作動流体である、上記[21]に記載の組成物。
Claims (6)
- 2−アミノ−2−メチル−1−プロパノール、2−アミノ−1−エタノール、1−アミノ−2−プロパノール、ビス(2−ヒドロキシプロピル)アミン、トリス(2−ヒドロキシプロピル)アミン、ビス(2−ヒドロキシエチル)アミン、トリス(2−ヒドロキシエチル)アミン、2−(2−アミノエトキシ)エタノール、および3−アミノ−4−オクタノールからなる群から選択される1種以上の化合物を更に含む、請求項1に記載の組成物。
- アミノアルコール化合物が、1−アミノシクロペンチルメタノール、1−アミノシクロオクチルメタノール、2−アミノ−2−フェニル−1−プロパノール、2−アミノ−2−メチル−1−ヘキサノール、2−アミノ−2−エチル−1−ペンタノール、2−アミノ−2−メチル−1−オクタノール、2−アミノ−2−エチル−1−ヘプタノールおよび2−アミノ−2−プロピル−1−ヘキサノールからなる群から選択される、請求項1または2に記載の組成物。
- 1級アミノアルコール化合物が、1−アミノシクロペンチルメタノール、1−アミノシクロオクチルメタノール、2−アミノ−2−メチル−1−ヘキサノールと2−アミノ−2−エチル−1−ペンタノールとの混合物、または2−アミノ−2−メチル−1−オクタノールと2−アミノ−2−エチル−1−ヘプタノールと2−アミノ−2−プロピル−1−ヘキサノールとの混合物である、請求項1に記載の組成物。
- 水系システムにおける微生物の生育を阻害する方法であって、該システムに、請求項1〜4のいずれかに記載の殺生物組成物を有効量添加することを含む、方法。
- 請求項1〜4のいずれかに記載の殺生物組成物を含む、金属作動流体。
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US61/073,894 | 2008-06-19 | ||
PCT/US2009/042032 WO2009140061A2 (en) | 2008-05-15 | 2009-04-29 | Aminoalcohol and biocide compositions for aqueous based systems |
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