RU2126272C1 - Композиция, замедляющая рост бактерий (варианты), способ ее получения (варианты) и способ замедления роста бактерий - Google Patents
Композиция, замедляющая рост бактерий (варианты), способ ее получения (варианты) и способ замедления роста бактерий Download PDFInfo
- Publication number
- RU2126272C1 RU2126272C1 RU93036963/14A RU93036963A RU2126272C1 RU 2126272 C1 RU2126272 C1 RU 2126272C1 RU 93036963/14 A RU93036963/14 A RU 93036963/14A RU 93036963 A RU93036963 A RU 93036963A RU 2126272 C1 RU2126272 C1 RU 2126272C1
- Authority
- RU
- Russia
- Prior art keywords
- formaldehyde
- dimethylhydantoin
- composition
- hydantoin
- dmh
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 241000894006 Bacteria Species 0.000 title claims abstract description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 424
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims abstract description 119
- 239000007864 aqueous solution Substances 0.000 claims abstract description 42
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 230000003993 interaction Effects 0.000 claims abstract description 9
- ZNYIPTYJBRGSSL-UHFFFAOYSA-N 1,5,5-trimethylimidazolidine-2,4-dione Chemical compound CN1C(=O)NC(=O)C1(C)C ZNYIPTYJBRGSSL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 75
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 11
- 229940091173 hydantoin Drugs 0.000 claims description 11
- CYFUTQFVJKHZRW-UHFFFAOYSA-N 1,3,5,5-tetramethylimidazolidine-2,4-dione Chemical compound CN1C(=O)N(C)C(C)(C)C1=O CYFUTQFVJKHZRW-UHFFFAOYSA-N 0.000 claims description 10
- 230000001580 bacterial effect Effects 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 abstract description 60
- SIQZJFKTROUNPI-UHFFFAOYSA-N 1-(hydroxymethyl)-5,5-dimethylhydantoin Chemical compound CC1(C)N(CO)C(=O)NC1=O SIQZJFKTROUNPI-UHFFFAOYSA-N 0.000 abstract description 39
- 239000007788 liquid Substances 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 206010040880 Skin irritation Diseases 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 239000002781 deodorant agent Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 abstract description 2
- 239000000839 emulsion Substances 0.000 abstract description 2
- 239000000499 gel Substances 0.000 abstract description 2
- 230000036556 skin irritation Effects 0.000 abstract description 2
- 231100000475 skin irritation Toxicity 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 28
- 239000000047 product Substances 0.000 description 24
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 19
- 229920001817 Agar Polymers 0.000 description 11
- 239000008272 agar Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000001332 colony forming effect Effects 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 238000004851 dishwashing Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 239000008223 sterile water Substances 0.000 description 4
- -1 unpleasant odor Chemical compound 0.000 description 4
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 235000012501 ammonium carbonate Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FHYNZKLNCPUNEU-UHFFFAOYSA-N 4-[(3,4-dihydroxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]oxolan-2-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)OCC1CC1=CC=C(O)C(O)=C1 FHYNZKLNCPUNEU-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SLZAMKNXRDJWLA-UHFFFAOYSA-N 1-(5-acetyl-2,6-dimethyl-1,4-dihydropyridin-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(C)=C(C(C)=O)C1 SLZAMKNXRDJWLA-UHFFFAOYSA-N 0.000 description 1
- DZNJSBHVDXLTIK-UHFFFAOYSA-N 1-(hydroxymethyl)imidazolidine-2,4-dione Chemical compound OCN1CC(=O)NC1=O DZNJSBHVDXLTIK-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- MPVXINJRXRIDDB-VCDGYCQFSA-N dodecanoic acid;(2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCC(O)=O MPVXINJRXRIDDB-VCDGYCQFSA-N 0.000 description 1
- CXPOFJRHCFPDRI-UHFFFAOYSA-N dodecylbenzene;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 CXPOFJRHCFPDRI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000012950 reanalysis Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Communicable Diseases (AREA)
- Plant Pathology (AREA)
- General Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Paper (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88728092A | 1992-05-21 | 1992-05-21 | |
| US07/887280 | 1992-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU93036963A RU93036963A (ru) | 1996-05-20 |
| RU2126272C1 true RU2126272C1 (ru) | 1999-02-20 |
Family
ID=25390816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93036963/14A RU2126272C1 (ru) | 1992-05-21 | 1993-05-20 | Композиция, замедляющая рост бактерий (варианты), способ ее получения (варианты) и способ замедления роста бактерий |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5405862A (enExample) |
| EP (1) | EP0571903B1 (enExample) |
| JP (1) | JP2657148B2 (enExample) |
| KR (1) | KR970002875B1 (enExample) |
| CN (2) | CN1064813C (enExample) |
| AT (1) | ATE141919T1 (enExample) |
| AU (1) | AU662409B2 (enExample) |
| BR (1) | BR9302029A (enExample) |
| CA (1) | CA2093045C (enExample) |
| DE (1) | DE69304253T2 (enExample) |
| DK (1) | DK0571903T3 (enExample) |
| ES (1) | ES2093878T3 (enExample) |
| GR (1) | GR3021711T3 (enExample) |
| HU (1) | HUT64177A (enExample) |
| MX (1) | MX9303006A (enExample) |
| PL (2) | PL173173B1 (enExample) |
| RU (1) | RU2126272C1 (enExample) |
| TW (1) | TW378152B (enExample) |
| UA (1) | UA37187C2 (enExample) |
| ZA (1) | ZA933464B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616722A (en) * | 1995-12-05 | 1997-04-01 | Mcintyre Group, Ltd. | Antimicrobial solution of formaldehyde substituted hydantoin and process for preparation |
| US5882357A (en) * | 1996-09-13 | 1999-03-16 | The Regents Of The University Of California | Durable and regenerable microbiocidal textiles |
| US6241783B1 (en) | 1996-09-13 | 2001-06-05 | The Regents Of The University Of California | Formaldehyde scavenging in microbiocidal articles |
| US6143204A (en) * | 1998-06-19 | 2000-11-07 | Lonza Inc. | Stabilization of iodopropynl compounds |
| US6121302A (en) * | 1999-05-11 | 2000-09-19 | Lonza, Inc. | Stabilization of isothiazolone |
| US6432262B1 (en) | 2000-06-08 | 2002-08-13 | Lonza, Inc. | Method of bleaching recycled papers with hydrogen peroxide stabilized with a methylolhydantoin |
| WO2002067685A1 (en) * | 2001-02-26 | 2002-09-06 | Lonza Inc. | Stable preservative formulations comprising halopropynyl compounds and butoxydiglycol solvent |
| ES2279217T3 (es) * | 2002-08-20 | 2007-08-16 | Lonza, Inc. | Composiciones antimicrobianas sinergicas, estables, a base de donadores de aldehidos y acido dehidroacetico y que son de bajo contenido en formaldehido libre. |
| US8138106B2 (en) | 2005-09-30 | 2012-03-20 | Rayonier Trs Holdings Inc. | Cellulosic fibers with odor control characteristics |
| EP2888340B1 (en) | 2012-08-21 | 2020-12-09 | Lonza, Llc | Method of scavenging sulfhydryl compounds |
| JP2015196745A (ja) * | 2014-03-31 | 2015-11-09 | シヤチハタ株式会社 | 水性インキ |
| US20180208885A1 (en) | 2017-01-24 | 2018-07-26 | Mary Ann Pfannenstiel | Antibiotic-free compositions for the prevention or control of coccidiosis |
| US20200362492A1 (en) * | 2018-01-24 | 2020-11-19 | Mitsui Chemicals, Inc. | Spunbonded nonwoven fabric, hygiene material, and method for producing spunbonded nonwoven fabric |
| CN109503493B (zh) * | 2018-12-23 | 2022-07-01 | 陕西化工研究院有限公司 | 一种防冻型1,3二羟甲基-5,5二甲基海因dmdmh的制备方法 |
| CN111693632A (zh) * | 2020-07-24 | 2020-09-22 | 上海市食品药品检验所 | 一种化妆品中总甲醛的提取方法及快速检测方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987184A (en) * | 1974-06-07 | 1976-10-19 | Glyco Chemicals, Inc. | Dimethylol dimethylhydantoin solution |
| SU1556683A1 (ru) * | 1987-07-13 | 1990-04-15 | Институт Химии Поверхности Ан Усср | Состав дл дезинфекции |
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| US4908456A (en) * | 1989-04-05 | 1990-03-13 | Takatori Corporation | Process for preparing methylolated hydantoins |
| US5036095A (en) * | 1989-11-14 | 1991-07-30 | Guy Andermann | Therapeutic use of DMDM Hydantoin |
| US5037843A (en) * | 1990-03-05 | 1991-08-06 | The Mcintyre Group, Ltd. | Antimicrobial preservative system and method comprising a formaldehyde substituted hydantoin |
-
1993
- 1993-05-18 ZA ZA933464A patent/ZA933464B/xx unknown
- 1993-05-20 KR KR1019930008897A patent/KR970002875B1/ko not_active Expired - Fee Related
- 1993-05-20 HU HU9301478A patent/HUT64177A/hu unknown
- 1993-05-20 CA CA002093045A patent/CA2093045C/en not_active Expired - Lifetime
- 1993-05-20 RU RU93036963/14A patent/RU2126272C1/ru not_active IP Right Cessation
- 1993-05-21 EP EP93108285A patent/EP0571903B1/en not_active Expired - Lifetime
- 1993-05-21 DK DK93108285.3T patent/DK0571903T3/da active
- 1993-05-21 DE DE69304253T patent/DE69304253T2/de not_active Expired - Lifetime
- 1993-05-21 AT AT93108285T patent/ATE141919T1/de not_active IP Right Cessation
- 1993-05-21 PL PL93299028A patent/PL173173B1/pl unknown
- 1993-05-21 JP JP5155999A patent/JP2657148B2/ja not_active Expired - Fee Related
- 1993-05-21 ES ES93108285T patent/ES2093878T3/es not_active Expired - Lifetime
- 1993-05-21 CN CN931082285A patent/CN1064813C/zh not_active Expired - Fee Related
- 1993-05-21 PL PL93318428A patent/PL173873B1/pl unknown
- 1993-05-21 AU AU38726/93A patent/AU662409B2/en not_active Ceased
- 1993-05-21 MX MX9303006A patent/MX9303006A/es unknown
- 1993-05-24 BR BR9302029A patent/BR9302029A/pt not_active Application Discontinuation
- 1993-05-28 UA UA93004631A patent/UA37187C2/uk unknown
- 1993-07-22 TW TW082105854A patent/TW378152B/zh not_active IP Right Cessation
-
1994
- 1994-02-14 US US08/196,894 patent/US5405862A/en not_active Expired - Lifetime
-
1996
- 1996-11-20 GR GR960403104T patent/GR3021711T3/el unknown
-
2000
- 2000-08-21 CN CNB001242547A patent/CN1305859C/zh not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987184A (en) * | 1974-06-07 | 1976-10-19 | Glyco Chemicals, Inc. | Dimethylol dimethylhydantoin solution |
| SU1556683A1 (ru) * | 1987-07-13 | 1990-04-15 | Институт Химии Поверхности Ан Усср | Состав дл дезинфекции |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP0571903B1 (en) | 1996-08-28 |
| MX9303006A (es) | 1997-08-30 |
| CA2093045A1 (en) | 1993-11-22 |
| CA2093045C (en) | 1997-03-18 |
| DE69304253D1 (de) | 1996-10-02 |
| BR9302029A (pt) | 1993-11-30 |
| GR3021711T3 (en) | 1997-02-28 |
| US5405862A (en) | 1995-04-11 |
| ZA933464B (en) | 1993-12-20 |
| AU3872693A (en) | 1993-12-02 |
| ATE141919T1 (de) | 1996-09-15 |
| JP2657148B2 (ja) | 1997-09-24 |
| ES2093878T3 (es) | 1997-01-01 |
| EP0571903A1 (en) | 1993-12-01 |
| PL173173B1 (pl) | 1998-02-27 |
| HU9301478D0 (en) | 1993-09-28 |
| CN1305859C (zh) | 2007-03-21 |
| PL299028A1 (en) | 1994-01-10 |
| CN1087778A (zh) | 1994-06-15 |
| DE69304253T2 (de) | 1997-01-30 |
| TW378152B (en) | 2000-01-01 |
| KR970002875B1 (ko) | 1997-03-12 |
| HUT64177A (en) | 1993-12-28 |
| DK0571903T3 (enExample) | 1997-02-10 |
| KR940005580A (ko) | 1994-03-21 |
| CN1064813C (zh) | 2001-04-25 |
| CN1308067A (zh) | 2001-08-15 |
| UA37187C2 (uk) | 2001-05-15 |
| PL173873B1 (pl) | 1998-05-29 |
| JPH06179658A (ja) | 1994-06-28 |
| AU662409B2 (en) | 1995-08-31 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20030521 |