FI104456B - Synergistiska kombinationer av jodpropargylföreningar med hexahydro-1, 3,5-tris(2-hydroxietyl)-s-triazin för kontroll av svamp- och bakterietillväxt i metallbearbetningsvätskor - Google Patents
Synergistiska kombinationer av jodpropargylföreningar med hexahydro-1, 3,5-tris(2-hydroxietyl)-s-triazin för kontroll av svamp- och bakterietillväxt i metallbearbetningsvätskor Download PDFInfo
- Publication number
- FI104456B FI104456B FI915125A FI915125A FI104456B FI 104456 B FI104456 B FI 104456B FI 915125 A FI915125 A FI 915125A FI 915125 A FI915125 A FI 915125A FI 104456 B FI104456 B FI 104456B
- Authority
- FI
- Finland
- Prior art keywords
- iodopropargyl
- compound
- tris
- hexahydro
- hydroxyethyl
- Prior art date
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- 239000012530 fluid Substances 0.000 title claims abstract description 69
- 238000005555 metalworking Methods 0.000 title claims abstract description 59
- 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 title claims abstract description 48
- 239000011885 synergistic combination Substances 0.000 title abstract description 11
- 230000001580 bacterial effect Effects 0.000 title description 22
- 230000002538 fungal effect Effects 0.000 title description 15
- 229910052740 iodine Inorganic materials 0.000 title description 3
- 239000011630 iodine Substances 0.000 title description 2
- -1 iodopropargyl compounds Chemical class 0.000 claims abstract description 33
- 244000005700 microbiome Species 0.000 claims abstract description 27
- 241000233866 Fungi Species 0.000 claims abstract description 17
- 241000894006 Bacteria Species 0.000 claims abstract description 14
- RCVKZMQGFZRHKO-UHFFFAOYSA-N 1-iodoprop-2-ynyl carbamate Chemical compound NC(=O)OC(I)C#C RCVKZMQGFZRHKO-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- ANMHCSPYNHLSEO-UHFFFAOYSA-N 1-iodohept-1-yn-4-yl carbamate Chemical compound CCCC(OC(N)=O)CC#CI ANMHCSPYNHLSEO-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- ZZHGIUCYKGFIPV-UHFFFAOYSA-M n-butylcarbamate Chemical compound CCCCNC([O-])=O ZZHGIUCYKGFIPV-UHFFFAOYSA-M 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 239000003139 biocide Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000003115 biocidal effect Effects 0.000 description 8
- 230000000813 microbial effect Effects 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 230000002335 preservative effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 4
- 230000002708 enhancing effect Effects 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000003754 machining Methods 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- YFLDZPUXCOSOGU-UHFFFAOYSA-N 1-iodoprop-2-ynyl n-butylcarbamate Chemical compound CCCCNC(=O)OC(I)C#C YFLDZPUXCOSOGU-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002173 cutting fluid Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002855 microbicide agent Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PXQCTMPKKDEGNE-UHFFFAOYSA-N C(CCC)NC(OCC#C)=O.[I] Chemical compound C(CCC)NC(OCC#C)=O.[I] PXQCTMPKKDEGNE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002599 biostatic effect Effects 0.000 description 1
- FMRPTARFPRVQIW-UHFFFAOYSA-N butyl(1-iodoprop-2-ynyl)carbamic acid Chemical compound CCCCN(C(O)=O)C(I)C#C FMRPTARFPRVQIW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/042—Sulfate esters
-
- 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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- 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
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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Claims (25)
1. Komposition för användning för regiering av mikroorganismers tillväxt, kännetecknad där- 5 av, att den innehäller (a) hexahydro-1,3,5-tris(2-hydroxietyl)-s-triazin och (b) en jodpropargylförening, sora är jodpropargylkarbamat eller 3-jodpropargyl-N-butylkarbamat, varvid föreningarna (a) och (b) är närva-rande i en mängd, som synergistiskt minskar mikroorganis-lo mers tillväxt, och förhällandet (a) : (b) är ca 1:99 -99:1.
2. Komposition enligt patentkrav 1, kännetecknad därav, att mikroorganismerna är bakterier eller svampar.
3. Komposition enligt patentkrav 1 eller 2, kännetecknad därav, att förhällandet (a) : (b) är ca 20:80 - 80:20.
4. Komposition enligt patentkrav 3, kännetecknad därav, att förhällandet (a) : (b) är ca 20 40:60 - 60:40.
5. Komposition enligt patentkrav 3, kännetecknad därav, att förhällandet (a) : (b) är 80:20.
6. Komposition enligt nägot av patentkraven 1-5, kännetecknad därav, att jodpropargylföreningen : 25 är jodpropargylkarbamat.
7. Komposition enligt nägot av patentkraven 1-5, kännetecknad därav, att nämnda jodpropargylfö-rening är 3 -jodpropargyl-N-butylkarbamat.
8. Komposition enligt patentkrav 6, k ä n n e -30 tecknad därav, att koncentrationen av föreningen ' *, (a) är ca 0,1 - 5000 ppm och koncentrationen av föreningen (b) är ca 0,1 - 5000 ppm.
9. Komposition enligt patentkrav 7, kännetecknad därav, att koncentrationen av föreningen 35 (a) är ca 0,1 - 1000 ppm och koncentrationen av föreningen (b) är ca 0,1 - 500 ppm. 104456
10. Förfarande för regiering av mikroorganismers tillväxt i en vattenbaserad vätska, känneteck-n a t därav, att tili vätskan sätts en komposition, som innehäller en synergistiskt effektiv mängd av (a) hexahyd- 5 ro-1,3,5-tris(2-hydroxietyl)-s-triazin och (b) en jodpro- pargylförening, som är jodpropargylkarbamat eller 3- jodpropargyl-N-butylkarbamat, varvid förhällandet (a) (b) är ca 1:99 - 99:1.
11. Förfarande enligt patentkrav 10, kanne -ίο tecknat därav, att mikroorganismerna är bakterier eller svampar.
12. Förfarande enligt patentkrav 10 eller 11, kännetecknat därav, att den vattenbaserade vätskan är en metallbearbetningsvätska. 15
13. Förfarande enligt nägot av patentkraven 10 - 12, kännetecknat därav, att jodpropargylföre-ningen är jodpropargylkarbamat.
14. Förfarande enligt nägot av patentkrav 10 - 12, kännetecknat därav, att jodpropargylföreningen 20 är 3 -j odpropargyl-N-butylkarbamat.
15. Metallbearbetningsvätska, känneteck-n a d därav, att den innehäller (a) hexahydro-1,3,5 -tris(2-hydroxietyl)-s-triazin och (b) en jodpropargylföre-ning, som är jodpropargylkarbamat eller 3-jodpropargyl-N- ; 25 butylkarbamat, varvid föreningarna (a) och (b) är närva- rande i en mängd, som synergistiskt minskar mikroorganismers tillväxt, och förhällandet (a) : (b) är ca 1:99 -99:1.
16. Vätska enligt patentkrav 15, k ä n n e -30 tecknat därav, att mikroorganismerna är bakterier eller svampar.
17. Koncentrerad metallbearbetningsvätska, k ä n-netecknad därav, att den innehäller (a) hexahydro-1, 3 , 5-tris (2-hydroxietyl)-s-triazin och (b) en jodpro- 35 pargylförening, som är jodpropargylkarbamat eller 3-jodpropargyl-N-butylkarbamat, varvid föreningarna (a) och (b) är närvarande i en sädan mängd, som minskar mikroorga- 104456 nismers tillväxt i vätskan synergistiskt, dä vätskan utspäds och den används pä metallbearbetningsplatsen.
18. Vätska enligt patentkrav 17, kanne -t e c k n a d därav, att jodpropargylföreningen är jo- 5 dpropargylkarbamat.
19. Vätska enligt patentkrav 17, kanne -t e c k n a d därav, att nämnda jodpropargylförening är 3 -j odpropargyl-N-butylkarbamat.
20. Förfarande för regiering av mikroorganismers ίο tillväxt i en utspädd metallbearbetningsvätska, k ä n - netecknat därav, att tili den utspädda metall-bearbetningsvätskan sätts (a) hexahydro-1,3,5-tris(2-hydroxietyl)-s-triazin och is (b) en jodpropargylförening, som är jodpropargyl- karbamat eller 3-jodpropargyl-N-butylkarbamat, varvid förhällandet tnellan föreningarna (a) : (b) är ca 1.-99 - 99:1 och varvid den totala mängden tillsatta föreningar (a) och (b) reglerar synergistiskt mikroorga-20 nismernas tillväxt i vätskan.
21. Förfarande enligt patentkrav 20, k ä n n e -t e c k n a t därav, att mikroorganismerna är bakterier eller svampar.
22. Förfarande enligt patentkrav 20 eller 21, 25 kännetecknat därav, att förhällandet (a) : (b) är ca 20:80 - 80:20.
23. Förfarande enligt patentkrav 22, kännetecknat därav, att förhällandet (a) : (b) är ca 40:60 - 60:40. 30
24. Förfarande enligt nägot av patentkraven 20 - 23, kännetecknat därav, att jodpropargylföreningen är jodpropargylkarbamat.
* 25. Förfarande enligt nägot av patentkraven 20 - 23, kännetecknat därav, att jodpropargylföre-35 ningen är 3-jodpropargyl-N-butylkarbamat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60681990A | 1990-10-31 | 1990-10-31 | |
| US60681990 | 1990-10-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI915125A0 FI915125A0 (fi) | 1991-10-30 |
| FI915125L FI915125L (fi) | 1992-05-01 |
| FI104456B true FI104456B (sv) | 2000-02-15 |
Family
ID=24429598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI915125A FI104456B (sv) | 1990-10-31 | 1991-10-30 | Synergistiska kombinationer av jodpropargylföreningar med hexahydro-1, 3,5-tris(2-hydroxietyl)-s-triazin för kontroll av svamp- och bakterietillväxt i metallbearbetningsvätskor |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5374631A (sv) |
| EP (1) | EP0484172B1 (sv) |
| JP (1) | JP3075490B2 (sv) |
| AT (1) | ATE165710T1 (sv) |
| AU (1) | AU659615B2 (sv) |
| BR (1) | BR9104795A (sv) |
| CA (1) | CA2054221C (sv) |
| DE (1) | DE69129356T2 (sv) |
| DK (1) | DK0484172T3 (sv) |
| ES (1) | ES2116999T3 (sv) |
| FI (1) | FI104456B (sv) |
| MX (1) | MX174316B (sv) |
| NO (1) | NO179573C (sv) |
| NZ (1) | NZ240393A (sv) |
| ZA (1) | ZA918514B (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5707929A (en) * | 1995-05-08 | 1998-01-13 | Troy Chemical Corporation | Biocidal compositions comprising mixtures of haloproynyl compounds and sulfur containing triazines |
| US5661149A (en) * | 1995-12-29 | 1997-08-26 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative |
| US5716917A (en) * | 1996-09-24 | 1998-02-10 | Cincinnati Milacron Inc. | Machining fluid composition and method of machining |
| DE19709875A1 (de) * | 1997-03-11 | 1998-09-17 | Bayer Ag | Fungizide Benzothiophen-2-carboxamid-S,S-dioxide für Kühlschmiermittel |
| DE19722858B4 (de) | 1997-05-23 | 2004-01-29 | Schülke & Mayr GmbH | Zusammensetzungen auf der Basis von Iodpropinyl- und Formaldehyd-Depot-Verbindungen und deren Verwendung als Konservierungsmittel |
| US6043209A (en) * | 1998-01-06 | 2000-03-28 | Playtex Products, Inc. | Stable compositions for removing stains from fabrics and carpets and inhibiting the resoiling of same |
| US7320758B2 (en) * | 2003-07-30 | 2008-01-22 | Triosyn Holding, Inc. | Method for control of microorganisms in metalworking fluid |
| DE102004059041A1 (de) | 2004-12-07 | 2006-06-08 | Schülke & Mayr GmbH | Verwendung von Formaldehyd und Formaldehyd freisetzenden Verbindungen in einer Zusammensetzung zur Bekämpfung von Mykobakterien |
| CN112136820A (zh) * | 2020-09-21 | 2020-12-29 | 西安三业新材料股份有限公司 | 一种强化型金属加工液防腐杀菌剂及其制备方法和应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US327220A (en) * | 1885-09-29 | John b | ||
| GB960732A (en) * | 1962-01-16 | 1964-06-17 | Dow Chemical Co | Method for preventing the growth of micro organisms in aqueous media |
| US3515671A (en) | 1968-07-19 | 1970-06-02 | Millmaster Onyx Corp | Microbiocidally treated metal working fluids |
| US3879445A (en) * | 1972-04-19 | 1975-04-22 | Phillips Petroleum Co | Monohaloalkenyl benzoates and trihaloalkyl benzoates |
| GB1460279A (en) * | 1973-05-10 | 1976-12-31 | Ici Ltd | Biocidal compositions |
| US3923870A (en) * | 1973-07-11 | 1975-12-02 | Troy Chemical Corp | Urethanes of 1-halogen substituted alkynes |
| GB1476862A (en) * | 1974-11-13 | 1977-06-16 | Rossmore H | Antimicrobial compositions and methods |
| US4055655A (en) | 1975-07-21 | 1977-10-25 | National Research Laboratories | Complexes of heavy metal ions and polyfunctional organic ligands used as antimicrobial agents |
| US4180473A (en) | 1975-07-21 | 1979-12-25 | National Research Laboratories | Method of transporting metal ions |
| CA1116622A (en) * | 1978-03-15 | 1982-01-19 | Yasuhiro Morisawa | Iodopropargyl derivatives their use and preparation |
| US4149983A (en) | 1978-04-03 | 1979-04-17 | Merck & Co., Inc. | Antimicrobial additive for metal working fluids |
| DE3122738A1 (de) * | 1980-06-12 | 1982-03-18 | CIBA-GEIGY AG, 4002 Basel | "verwendung von jodacetamid zur bekaempfung von schadorganismen und mittel fuer die bekaempfung" |
| US4830657A (en) * | 1982-06-21 | 1989-05-16 | Calgon Corporation | Synergistic antimicrobial combination |
| JPS6071009A (ja) * | 1983-09-26 | 1985-04-22 | Sanyo Chem Ind Ltd | 凝集活性物質の製造法 |
| US4616004A (en) * | 1984-09-27 | 1986-10-07 | Chevron Research Company | 1-iodopropargyl-3,4-disubstituted-Δ2 -1,2,4-triazolidin-5-one fungicides |
| DE3510203A1 (de) * | 1985-03-21 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Neue iodpropargylether, ein verfahren zu ihrer herstellung und ihre verwendung |
| US4666616A (en) * | 1985-04-30 | 1987-05-19 | Board Of Governers Of Wayne State University | Synergistic antimicrobial or biocidal mixtures |
| DE3719194A1 (de) * | 1987-06-09 | 1988-12-29 | Henkel Kgaa | Fungizide wirkstoffgemische |
| US4844891A (en) * | 1988-02-03 | 1989-07-04 | Lonza, Inc. | Admixtures of iodopropargyl compounds and a formaldehyde donor |
| DE3828473A1 (de) * | 1988-08-22 | 1990-03-15 | Deggendorfer Werft Eisenbau | Mit stabelektroden arbeitender lichtbogen-schweissautomat und eine bevorzugte anwendung eines solchen |
| US4945109A (en) * | 1988-08-24 | 1990-07-31 | Buckman Laboratories International, Inc. | Ester of carbamic acid useful as a microbicide and a preservative |
-
1991
- 1991-10-25 CA CA002054221A patent/CA2054221C/en not_active Expired - Fee Related
- 1991-10-25 ZA ZA918514A patent/ZA918514B/xx unknown
- 1991-10-29 NZ NZ240393A patent/NZ240393A/en not_active IP Right Cessation
- 1991-10-30 FI FI915125A patent/FI104456B/sv active
- 1991-10-30 NO NO914264A patent/NO179573C/no not_active IP Right Cessation
- 1991-10-30 MX MX9101859A patent/MX174316B/es active IP Right Grant
- 1991-10-30 AU AU86829/91A patent/AU659615B2/en not_active Ceased
- 1991-10-31 AT AT91310106T patent/ATE165710T1/de not_active IP Right Cessation
- 1991-10-31 DK DK91310106T patent/DK0484172T3/da active
- 1991-10-31 ES ES91310106T patent/ES2116999T3/es not_active Expired - Lifetime
- 1991-10-31 DE DE69129356T patent/DE69129356T2/de not_active Expired - Fee Related
- 1991-10-31 JP JP03286732A patent/JP3075490B2/ja not_active Expired - Fee Related
- 1991-10-31 BR BR919104795A patent/BR9104795A/pt not_active IP Right Cessation
- 1991-10-31 EP EP91310106A patent/EP0484172B1/en not_active Revoked
-
1993
- 1993-01-27 US US08/013,552 patent/US5374631A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO914264L (no) | 1992-05-04 |
| FI915125L (fi) | 1992-05-01 |
| EP0484172B1 (en) | 1998-05-06 |
| NZ240393A (en) | 1994-03-25 |
| US5374631A (en) | 1994-12-20 |
| NO914264D0 (no) | 1991-10-30 |
| NO179573B (no) | 1996-07-29 |
| DK0484172T3 (da) | 1998-10-07 |
| AU8682991A (en) | 1992-05-07 |
| BR9104795A (pt) | 1992-06-16 |
| FI915125A0 (fi) | 1991-10-30 |
| DE69129356D1 (de) | 1998-06-10 |
| JPH05124909A (ja) | 1993-05-21 |
| AU659615B2 (en) | 1995-05-25 |
| MX174316B (es) | 1994-05-04 |
| EP0484172A1 (en) | 1992-05-06 |
| ES2116999T3 (es) | 1998-08-01 |
| ATE165710T1 (de) | 1998-05-15 |
| ZA918514B (en) | 1992-11-25 |
| NO179573C (no) | 1996-11-06 |
| CA2054221C (en) | 1999-09-14 |
| JP3075490B2 (ja) | 2000-08-14 |
| CA2054221A1 (en) | 1992-05-01 |
| DE69129356T2 (de) | 1998-09-03 |
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