EP0773281A2 - Préparations pour refrigerants Inbrifiants stabilisées - Google Patents
Préparations pour refrigerants Inbrifiants stabilisées Download PDFInfo
- Publication number
- EP0773281A2 EP0773281A2 EP96250190A EP96250190A EP0773281A2 EP 0773281 A2 EP0773281 A2 EP 0773281A2 EP 96250190 A EP96250190 A EP 96250190A EP 96250190 A EP96250190 A EP 96250190A EP 0773281 A2 EP0773281 A2 EP 0773281A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- additive mixture
- weight
- mixture according
- cooling lubricant
- stabilizer
- 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 claims abstract 3
- 238000002360 preparation method Methods 0.000 title description 22
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 239000005068 cooling lubricant Substances 0.000 claims abstract description 43
- 239000000654 additive Substances 0.000 claims abstract description 37
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 230000000996 additive effect Effects 0.000 claims abstract description 34
- 239000003381 stabilizer Substances 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 28
- 238000002144 chemical decomposition reaction Methods 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims description 28
- CMNSJKWAGPRSRK-UHFFFAOYSA-N 2-octyl-3h-1,2-thiazole 1-oxide Chemical compound CCCCCCCCN1CC=CS1=O CMNSJKWAGPRSRK-UHFFFAOYSA-N 0.000 claims description 20
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 18
- 229960005323 phenoxyethanol Drugs 0.000 claims description 18
- OAAZUWWNSYWWHG-UHFFFAOYSA-N 1-phenoxypropan-1-ol Chemical class CCC(O)OC1=CC=CC=C1 OAAZUWWNSYWWHG-UHFFFAOYSA-N 0.000 claims description 14
- -1 amino, Carboxy Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- ZHDBTKPXEJDTTQ-UHFFFAOYSA-N dipyrithione Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-] ZHDBTKPXEJDTTQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- XDILZEPJCPEDLT-UHFFFAOYSA-N [Na].[O-][N+]1=CC=CC=C1S Chemical compound [Na].[O-][N+]1=CC=CC=C1S XDILZEPJCPEDLT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 6
- 229960003811 pyrithione disulfide Drugs 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 2
- PCALKHSQMLZQEQ-UHFFFAOYSA-N 1-phenoxybutan-1-ol Chemical class CCCC(O)OC1=CC=CC=C1 PCALKHSQMLZQEQ-UHFFFAOYSA-N 0.000 claims description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 claims description 2
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims description 2
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical group CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical class 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- LOJHHQNEBFCTQK-UHFFFAOYSA-N 2-phenoxypropan-1-ol Chemical compound OCC(C)OC1=CC=CC=C1 LOJHHQNEBFCTQK-UHFFFAOYSA-N 0.000 claims 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 43
- 239000011734 sodium Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 239000002826 coolant Substances 0.000 description 11
- 230000006641 stabilisation Effects 0.000 description 10
- 238000011105 stabilization Methods 0.000 description 10
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 241000321713 Dromus Species 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000013049 sediment Substances 0.000 description 6
- 239000012895 dilution Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 229940051250 hexylene glycol Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005555 metalworking Methods 0.000 description 3
- FDHZSJWAYZGGKD-UHFFFAOYSA-N 3-octyl-1,2-thiazole 1-oxide Chemical compound CCCCCCCCC=1C=CS(=O)N=1 FDHZSJWAYZGGKD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 229940043810 zinc pyrithione Drugs 0.000 description 2
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
- UTBVIMLZIRIFFR-UHFFFAOYSA-N 2-methylthio-1,3-benzothiazole Chemical compound C1=CC=C2SC(SC)=NC2=C1 UTBVIMLZIRIFFR-UHFFFAOYSA-N 0.000 description 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- AGWWTUWTOBEQFE-UHFFFAOYSA-N 4-methyl-1h-1,2,4-triazole-5-thione Chemical compound CN1C=NN=C1S AGWWTUWTOBEQFE-UHFFFAOYSA-N 0.000 description 1
- CDFRIBJXDHLDHP-UHFFFAOYSA-N 5-chloro-2-methyl-3h-1,2-thiazole 1-oxide Chemical compound CN1CC=C(Cl)S1=O CDFRIBJXDHLDHP-UHFFFAOYSA-N 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 239000004158 L-cystine Substances 0.000 description 1
- 235000019393 L-cystine Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/061—Carbides; Hydrides; Nitrides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/16—Carbon dioxide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/18—Ammonia
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
Definitions
- the present invention relates to additive mixtures for cooling lubricant products and cooling lubricant products which contain an isothiazolone and a stabilizer which is effective against chemical decomposition of the isothiazolone.
- Isothiazolone compounds are known to be effective bactericidal and / or fungicidal active ingredients in cooling lubricants for metalworking.
- certain components in metalworking fluids tend to destroy the isothiazolones and thus eliminate their microbiological protective activity. This is particularly the case when the metalworking fluids are in a concentrated form.
- microbicides that are present in combination with isothiazolones can also attack isothiazolones.
- An example of this is the sodium salt of 2-mercapto-pyridine-N-oxide (sodium omadine) that 5-chloro-2-methyl-isothiazolone decomposes in any system in which both are present together.
- isothiazolones can be stabilized against chemical decomposition by adding a metal nitrite or a metal nitrate. It is further disclosed that other common salts, including carbonates, sulfates, chlorates, perchlorates and chlorides, are not effective in stabilizing isothiazolone solutions.
- EP-A-0 425 143, US-A-4 150 026 and US-A-4 241 214 disclose that metal salt complexes of isothiazolones are useful because of their improved thermal stability while maintaining biological activity.
- EP-B-0 443 821 are additive mixtures for cooling lubricant products which, according to the preamble of claim 1, contain an isothiazolone and a stabilizer which is effective against chemical decomposition of the isothiazolone.
- an isothiazolone and a stabilizer which is effective against chemical decomposition of the isothiazolone.
- sulfur-containing compounds or salts thereof which with the Isothiazolone can reversibly form an adduct, especially compounds in which a sulfur atom is attached to an aromatic ring containing nitrogen.
- Suitable compounds are (in EP-B-0 443 821) 4-mercaptopyridine, the sodium salt of 2-mercaptopyridine, 2-mercaptobenzothiazole and 4-methyl-4-H-1,2,4-triazole-3-thiol .
- Other compounds mentioned are 2-methylthiobenzothiazole, 2-thiohydantoin, methylene bisthiocyanate, L-cystine and 4-R (thiazolidene-thione-4-carboxylic acid).
- the ratio of stabilizer to isothiazolone effective for stabilization is at least 0.1: 1, in particular between 0.5: 1 and 1.5: 1.
- compositions of isothiazolone and stabilizer known from EP-B-0 443 821 can additionally contain solvents.
- Preferred solvents are so-called "capped polyols", e.g. Triethylene glycol dimethyl ether.
- the object of the present invention to provide additive mixtures for cooling lubricant products which contain isothiazolones as bactericidal and / or fungicidal active ingredients, which protect cooling lubricant concentrates or cooling lubricants produced therefrom from microbial attack and improve the durability and service life of the cooling lubricant products.
- the additive mixtures according to the invention should themselves be sufficiently stable and storable and durable under practical conditions.
- compositions containing isothiazolone and stabilizer in such a way that they can be metered easily into commercially available cooling lubricants, for example by adding a liquid preparation.
- the metering should be possible in a coolant concentrate or in a coolant, preferably a water-mixed coolant.
- a solubilizer is additionally provided in the additive mixtures, which is selected from phenoxyethanol, phenoxypropanols, phenoxybutanols, dipropylene glycol, 1-methoxypropanol-2, butyl diglycol and mixtures thereof.
- the solubilizer is preferably phenoxyethanol, phenoxypropanol or 1-methoxypropanol-2.
- the solubilizer is, for example, in an amount of 30 to 91.7% by weight, for example 30 to 75, preferably 40 to 70% by weight, more preferably 50 to 65% by weight and in particular approximately 58% by weight Additive mixture included.
- the cooling lubricant products contain an additive mixture according to the invention.
- the cooling lubricant products can be present as a cooling lubricant concentrate or contain the cooling lubricant concentrate. Accordingly, the additives according to the invention can be introduced into cooling lubricant concentrates, which are subsequently diluted to cooling lubricants.
- the cooling lubricant products can be in the form of a solution or an emulsion. Water-mixed cooling lubricants are preferably produced.
- the isothiazolones used in the additive mixture according to the invention include those which are known from EP-B-0 443 821.
- Y is a (C 1 -C 18 ) alkyl or (C 3 -C 12 ) cycloalkyl group which is linked to one or more hydroxyl, halogen, cyano, alkylamino, dialkylamino, aryl, amino, Carboxy, carbalkoxy, alkoxy, aryloxy, alkylthio, arylthio, haloalkoxy, cycloalkylamino, carbamoxy or isothiazolonyl groups, an unsubstituted or halogen-substituted (C 2 -C 8 ) alkenyl or - Alkynyl group, a (C 7 -C 10 ) aralkyl group which may be substituted with one or more halogen atoms or one or more (
- Suitable stabilizers or stabilizer mixtures for the isothiazolone compounds are the compounds known from the prior art, and in particular sulfur-containing compounds or salts thereof, which are reversible with the isothiazolone Can form an adduct.
- Heterocyclic sulfur-nitrogen compounds such as 2-mercaptopyridine-N-oxide and corresponding salts, preferably alkali metal or ammonium salts such as pyrion-Na (40% aqueous solution of 2-mercaptorpyridine-N-oxide sodium salt) are particularly suitable.
- 2-mercaptopyridine-N-oxide metal salt complexes such as zinc-pyrithione (e.g.
- TCMTB Thiocyanatomethyl thio-benzothiazole
- pyrion-Na, zinc pyrithione, pyrion disulfide and 2-mercaptobenzothiazole are preferred.
- mild oxidizing agents such as iodopropynyl butyl carbamate, hydrogen peroxide, t-butyl hydroperoxide, sodium bromate and Cu (II) salts are also suitable as stabilizers or co-stabilizers according to the invention, sodium bromate, hydrogen peroxide, 2-tert-butyl-6-methylphenol and pyrion disulfidals Co-stabilizers are preferred.
- the isothiazolone content in the additive mixture can be 2.25 to 20.25% by weight, for example 6.75 to 20.25% by weight, preferably 9 to 13.5% by weight and in particular approximately 11 % By weight.
- the stabilizer content in the additive mixture can be approximately 1.3 to 10% by weight, for example 4 to 10% by weight, preferably 6 to 8% by weight and in particular approximately 7% by weight, with for example also 0.05 up to 1.0, preferably 0.5 to 0.1% by weight, in particular 0.2% by weight, of cocatalyst can be present.
- the molar ratio of isothiazolone compound: stabilizer is, for example, at least 10: 1, preferably between 1.5: 1 and 1: 1.5 and in particular about 1: 1, such as between 1.1: 1 and 1: 1.27.
- the additive mixtures are preferably incorporated into commercially available coolant concentrates, from which dilutions with water are then made, e.g. 4% dilutions.
- the liquid preparations can optionally contain further additives which support the functional properties of the cooling lubricant or cooling lubricant additive.
- the active ingredient isothiazolone
- the stabilizer for example Pyrion-Na
- the preparation is easy to dose and can be stored and stored even under practical conditions.
- the ease of handling of the preparation is also advantageous compared to the storage, preparation and metering of active ingredients and stabilizers present in two-component systems.
- the additive mixtures according to the invention can be added effectively to cooling lubricant concentrates, so that their durability and the service life of the finished cooling lubricant products are improved compared to known systems.
- the increased stability of the preparations according to the invention is particularly evident in the lower tendency to form sediments.
- Kathon RH 893 denotes a 45% n-octylisothiazolone solution in 1,2-propylene glycol and Pyrion-Na a 40% aqueous 2-mercaptopyridine-N-oxide sodium salt solution.
- Formulations based on Kathon 893 and Pyrion-Na (40%) were dissolved in a molar ratio of 1: 1 to 1: 5 in various solubilizers and examined for compatibility and stability.
- the total active substance content (sum of N-octylisothiazolone and 2-mercaptopyridine-N-oxide-Na salt) was approx. 18%.
- a Boko and Lager Boko test (10 days storage of the cooling lubricant concentrate at 40 ° C) was carried out using the samples A, B, C from Example 6 (preparations based on Kathon 893, Pyrion-Na and solubilizers), the individual active ingredients and a combination of the active ingredients NOITZ (Kathon 893 was used) and Na-Pyrion.
- the preparations or active ingredients were incorporated into the concentrates, from which 4% dilutions were then made in Norderstedter city water.
- Kathon 893, Pyrion-Na and the solubilizer according to the invention not only facilitated the handling and metering of the agent, it also improved the stability and the effectiveness of the biocide mixture.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19534532A DE19534532C2 (de) | 1995-09-08 | 1995-09-08 | Additivmischungen für Kühlschmiermittelprodukte und deren Verwendung |
| DE19534532 | 1995-09-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0773281A2 true EP0773281A2 (fr) | 1997-05-14 |
| EP0773281A3 EP0773281A3 (fr) | 1998-05-13 |
| EP0773281B1 EP0773281B1 (fr) | 2005-10-19 |
Family
ID=7772453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96250190A Expired - Lifetime EP0773281B1 (fr) | 1995-09-08 | 1996-09-05 | Préparations pour refrigerants Inbrifiants stabilisées |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0773281B1 (fr) |
| DE (2) | DE19534532C2 (fr) |
| ES (1) | ES2247597T3 (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6211213B1 (en) * | 1999-04-16 | 2001-04-03 | Rohm And Haas Company | Stable microbicide formulation |
| WO2002067685A1 (fr) * | 2001-02-26 | 2002-09-06 | Lonza Inc. | Preparations de conservateurs stables comprenant des composes halopropynyle et un solvant butoxydiglycol |
| US6607738B2 (en) | 1997-04-24 | 2003-08-19 | Nipa Laboratories, Ltd. | Chemical composition |
| EP1332675A3 (fr) * | 2002-01-31 | 2003-10-01 | Rohm and Haas | Associations microbicides synergiques |
| EP1514473A1 (fr) * | 2003-09-04 | 2005-03-16 | Air Liquide Santé (International) | Composition microbicide à faible teneur en sels ou exempte de ceux-ci à base de dérivés d'isothiazolone et de pyrion disulfure |
| US9034905B2 (en) | 2003-02-05 | 2015-05-19 | Rohm And Haas Company | Synergistic microbicidal combinations |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2320026B (en) | 1996-12-05 | 2000-01-26 | Sunkyong Ind Ltd | Stabilized isothiazolone solution |
| DE19961621C2 (de) * | 1999-12-13 | 2002-11-14 | Schuelke & Mayr Gmbh | Bakterizide und fungizide flüssige Zubereitungen für technische Produkte |
| DE102004052878A1 (de) | 2004-11-02 | 2006-05-04 | Schülke & Mayr GmbH | Isothiazolonhaltige Konservierungsmittel mit verbesserter Stabilität |
| DE102006045066B4 (de) * | 2006-09-21 | 2010-07-01 | Schülke & Mayr GmbH | Mikrobizide Zubereitung auf der Basis von 1,2-Benzisothiazolin-3-on mit einem Gehalt an aromatischem Alkohol |
| DE102009048189A1 (de) * | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Lagerstabile mikrobizide Konzentrate und deren Verwendung als Konservierungsmittel |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870795A (en) * | 1973-02-28 | 1975-03-11 | Rohm & Haas | Stabilization of solutions of 3-isothiazolones employing certain metal nitrates and nitrites |
| DE3904099C1 (fr) * | 1989-02-11 | 1990-07-12 | Schuelke & Mayr Gmbh, 2000 Norderstedt, De | |
| DE3911808A1 (de) * | 1989-04-11 | 1990-10-18 | Riedel De Haen Ag | Fluessiges konservierungsmittel |
| DE58906847D1 (de) * | 1989-11-10 | 1994-03-10 | Thor Chemie Gmbh | Stabilisierte wässrige Lösungen von 3-Isothiazolinonen. |
| GB9003871D0 (en) * | 1990-02-21 | 1990-04-18 | Rohm & Haas | Stabilization of isothiazolones |
| US5037989A (en) * | 1990-04-05 | 1991-08-06 | Rohm And Haas Company | Phenoxyalkanol as a stabilizer for isothiazolone concentrates |
| US5108500A (en) * | 1990-12-10 | 1992-04-28 | Rohm And Haas Company | Stabilization of water insoluble 3-isothiazolones |
| JP3524937B2 (ja) * | 1992-02-10 | 2004-05-10 | 日本エンバイロケミカルズ株式会社 | 工業用殺菌剤 |
| GB9300936D0 (en) * | 1993-01-19 | 1993-03-10 | Zeneca Ltd | Stable liquid compositions and their use |
| JPH07133205A (ja) * | 1993-11-08 | 1995-05-23 | Shinto Paint Co Ltd | 木材用防カビ組成物 |
| US5478797A (en) * | 1994-11-21 | 1995-12-26 | Rohm And Haas Company | Bromate stabilization of nitrate-free 3-isothiazolones at pH 4-5.1 |
| US5599827A (en) * | 1995-05-16 | 1997-02-04 | Rohm And Haas Company | Stable microemulsions of certain 3-isothiazolone compounds |
-
1995
- 1995-09-08 DE DE19534532A patent/DE19534532C2/de not_active Expired - Fee Related
-
1996
- 1996-09-05 DE DE59611282T patent/DE59611282D1/de not_active Expired - Lifetime
- 1996-09-05 ES ES96250190T patent/ES2247597T3/es not_active Expired - Lifetime
- 1996-09-05 EP EP96250190A patent/EP0773281B1/fr not_active Expired - Lifetime
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6607738B2 (en) | 1997-04-24 | 2003-08-19 | Nipa Laboratories, Ltd. | Chemical composition |
| US6211213B1 (en) * | 1999-04-16 | 2001-04-03 | Rohm And Haas Company | Stable microbicide formulation |
| WO2002067685A1 (fr) * | 2001-02-26 | 2002-09-06 | Lonza Inc. | Preparations de conservateurs stables comprenant des composes halopropynyle et un solvant butoxydiglycol |
| EP1332675A3 (fr) * | 2002-01-31 | 2003-10-01 | Rohm and Haas | Associations microbicides synergiques |
| EP1488699A1 (fr) * | 2002-01-31 | 2004-12-22 | Rohm And Haas Company | Associations microbicides synergiques |
| US9426994B2 (en) | 2003-02-05 | 2016-08-30 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9034905B2 (en) | 2003-02-05 | 2015-05-19 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9426993B2 (en) | 2003-02-05 | 2016-08-30 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9474280B2 (en) | 2003-02-05 | 2016-10-25 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9480258B2 (en) | 2003-02-05 | 2016-11-01 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9491945B2 (en) | 2003-02-05 | 2016-11-15 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9497968B2 (en) | 2003-02-05 | 2016-11-22 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9497969B2 (en) | 2003-02-05 | 2016-11-22 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US9532571B2 (en) | 2003-02-05 | 2017-01-03 | Rohm And Haas Company | Synergistic microbicidal combinations |
| JP2005082596A (ja) * | 2003-09-04 | 2005-03-31 | L'air Liquide Sante Internatl | イソチアゾロン誘導体およびピリオンジスルフィドに基づく低塩含量または塩フリーの殺菌剤組成物 |
| EP1514473A1 (fr) * | 2003-09-04 | 2005-03-16 | Air Liquide Santé (International) | Composition microbicide à faible teneur en sels ou exempte de ceux-ci à base de dérivés d'isothiazolone et de pyrion disulfure |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19534532C2 (de) | 1999-04-08 |
| EP0773281B1 (fr) | 2005-10-19 |
| DE19534532A1 (de) | 1997-03-20 |
| ES2247597T3 (es) | 2006-03-01 |
| EP0773281A3 (fr) | 1998-05-13 |
| DE59611282D1 (de) | 2006-03-02 |
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