DK141982B - Antimikrobielt konserveringsmiddel, især til brug i kosmetiske cremer. - Google Patents

Antimikrobielt konserveringsmiddel, især til brug i kosmetiske cremer. Download PDF

Info

Publication number: DK141982B
Authority: DK; Denmark
Prior art keywords: bromo; compound; dioxane; nitro; methyl
Prior art date: 1973-02-16

Application number

DK80174A

Other languages

Danish (da)

English (en)

Other versions

DK141982C (fr

Inventor

Lewis Christopher Lappas

Clarence August Hirsch

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1973-02-16

Filing date

1974-02-15

Publication date

1980-08-04

1974-02-15 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-08-04 Publication of DK141982B publication Critical patent/DK141982B/da

1981-02-16 Application granted granted Critical

1981-02-16 Publication of DK141982C publication Critical patent/DK141982C/da

Links

230000000845 anti-microbial effect Effects 0.000 title description 16
239000003755 preservative agent Substances 0.000 title description 15
230000002335 preservative effect Effects 0.000 title description 14
239000008278 cosmetic cream Substances 0.000 title description 12
150000001875 compounds Chemical class 0.000 description 65
239000000203 mixture Substances 0.000 description 23
VFBSFSGHILWWIJ-UHFFFAOYSA-N 5-bromo-2-methyl-5-nitro-1,3-dioxane Chemical compound CC1OCC(Br)([N+]([O-])=O)CO1 VFBSFSGHILWWIJ-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
238000002474 experimental method Methods 0.000 description 16
244000005700 microbiome Species 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
229940046305 5-bromo-5-nitro-1,3-dioxane Drugs 0.000 description 13
229920001817 Agar Polymers 0.000 description 13
239000008272 agar Substances 0.000 description 13
XVBRCOKDZVQYAY-UHFFFAOYSA-N bronidox Chemical compound [O-][N+](=O)C1(Br)COCOC1 XVBRCOKDZVQYAY-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000002401 inhibitory effect Effects 0.000 description 11
230000035945 sensitivity Effects 0.000 description 11
LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229940126062 Compound A Drugs 0.000 description 8
241000233866 Fungi Species 0.000 description 8
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
239000004599 antimicrobial Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
241000894006 Bacteria Species 0.000 description 6
206010015150 Erythema Diseases 0.000 description 6
206010030113 Oedema Diseases 0.000 description 6
231100000321 erythema Toxicity 0.000 description 6
230000007794 irritation Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
125000000129 anionic group Chemical group 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000006071 cream Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
-1 fungistates Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000000126 substance Substances 0.000 description 4
UPENUQKAOJSMCX-UHFFFAOYSA-N 5-bromo-2-ethyl-5-nitro-1,3-dioxane Chemical compound CCC1OCC(Br)([N+]([O-])=O)CO1 UPENUQKAOJSMCX-UHFFFAOYSA-N 0.000 description 3
YKBOGPGICIIIRV-UHFFFAOYSA-N 5-bromo-5-nitro-2-propyl-1,3-dioxane Chemical compound CCCC1OCC(Br)([N+]([O-])=O)CO1 YKBOGPGICIIIRV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
239000004480 active ingredient Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical compound OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 description 2
DJFLLJHVLVQBJS-UHFFFAOYSA-N 5-bromo-5-nitro-2-propan-2-yl-1,3-dioxane Chemical compound CC(C)C1OCC(Br)([N+]([O-])=O)CO1 DJFLLJHVLVQBJS-UHFFFAOYSA-N 0.000 description 2
241000228197 Aspergillus flavus Species 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
206010040880 Skin irritation Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
HVUMOYIDDBPOLL-IIZJTUPISA-N [2-[(2r,3s,4r)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O HVUMOYIDDBPOLL-IIZJTUPISA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
125000005456 glyceride group Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
231100000475 skin irritation Toxicity 0.000 description 2
230000036556 skin irritation Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000758 substrate Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
DJUVIGPNNOQVTE-UHFFFAOYSA-N 2-nitro-1,3-dioxane Chemical compound [O-][N+](=O)C1OCCCO1 DJUVIGPNNOQVTE-UHFFFAOYSA-N 0.000 description 1
ZWECGWAIOMUNCR-UHFFFAOYSA-N 2-nitropropane-1,3-diol;sodium Chemical compound [Na].OCC(CO)[N+]([O-])=O ZWECGWAIOMUNCR-UHFFFAOYSA-N 0.000 description 1
UHOOGMASJKXTJZ-UHFFFAOYSA-N 5-bromo-2-methyl-1,3-dioxane Chemical compound CC1OCC(Br)CO1 UHOOGMASJKXTJZ-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
235000021537 Beetroot Nutrition 0.000 description 1
101100452784 Caenorhabditis elegans ire-1 gene Proteins 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
235000013175 Crataegus laevigata Nutrition 0.000 description 1
206010051814 Eschar Diseases 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
229910018540 Si C Inorganic materials 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
PMBWYDCSOSTTDK-UHFFFAOYSA-N [Br].CCOC(C)=O Chemical compound [Br].CCOC(C)=O PMBWYDCSOSTTDK-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229940031955 anhydrous lanolin Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000003796 beauty Effects 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
231100000333 eschar Toxicity 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
229940097789 heavy mineral oil Drugs 0.000 description 1
230000001976 improved effect Effects 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000007747 plating Methods 0.000 description 1
229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
229940113115 polyethylene glycol 200 Drugs 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
GJIMNMWWEUBESO-UHFFFAOYSA-M sodium formaldehyde hydroxide Chemical compound [OH-].[Na+].O=C GJIMNMWWEUBESO-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
229940045860 white wax Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DK80174A 1973-02-16 1974-02-15 Antimikrobielt konserveringsmiddel, især til brug i kosmetiske cremer. DK141982B (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US33341873A	1973-02-16	1973-02-16
US33341873		1973-02-16
US38299273A	1973-07-26	1973-07-26
US38299273		1973-07-26

Publications (2)

Publication Number	Publication Date
DK141982B true DK141982B (da)	1980-08-04
DK141982C DK141982C (fr)	1981-02-16

Family

ID=26988729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK80174A DK141982B (da)	1973-02-16	1974-02-15	Antimikrobielt konserveringsmiddel, især til brug i kosmetiske cremer.

Country Status (20)

Country	Link
JP (1)	JPS5821601B2 (fr)
AR (1)	AR200674A1 (fr)
AT (1)	AT339491B (fr)
BG (1)	BG20581A3 (fr)
BR (1)	BR7401142D0 (fr)
CA (1)	CA1010882A (fr)
CH (1)	CH592453A5 (fr)
DD (1)	DD110865A5 (fr)
DE (1)	DE2407289C2 (fr)
DK (1)	DK141982B (fr)
ES (1)	ES423013A1 (fr)
FR (1)	FR2218096B1 (fr)
GB (2)	GB1461312A (fr)
IE (1)	IE38787B1 (fr)
IT (1)	IT1054160B (fr)
NL (1)	NL179443C (fr)
PH (1)	PH11734A (fr)
RO (1)	RO63017A (fr)
SE (1)	SE417266B (fr)
SU (1)	SU496729A3 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2913466A1 (de) *	1979-04-04	1980-10-16	Henkel Kgaa	Verfahren zur herstellung von 5-brom- 5-nitro-1,3-dioxan
DE19739192A1 (de) *	1997-09-08	1999-03-11	Henkel Kgaa	Verfahren zur Herstellung von 5-Brom-5-nitro-1,3-dioxan

1974
- 1974-01-23 IE IE13474A patent/IE38787B1/xx unknown
- 1974-02-05 IT IT2020974A patent/IT1054160B/it active
- 1974-02-07 ES ES423013A patent/ES423013A1/es not_active Expired
- 1974-02-12 GB GB642374A patent/GB1461312A/en not_active Expired
- 1974-02-12 GB GB3319676A patent/GB1461313A/en not_active Expired
- 1974-02-14 AT AT118674A patent/AT339491B/de not_active IP Right Cessation
- 1974-02-14 FR FR7405026A patent/FR2218096B1/fr not_active Expired
- 1974-02-15 DD DD17657774A patent/DD110865A5/xx unknown
- 1974-02-15 AR AR25239274A patent/AR200674A1/es active
- 1974-02-15 DK DK80174A patent/DK141982B/da unknown
- 1974-02-15 BR BR114274A patent/BR7401142D0/pt unknown
- 1974-02-15 CA CA192,648A patent/CA1010882A/en not_active Expired
- 1974-02-15 DE DE19742407289 patent/DE2407289C2/de not_active Expired
- 1974-02-15 NL NL7402164A patent/NL179443C/xx not_active IP Right Cessation
- 1974-02-15 CH CH215574A patent/CH592453A5/xx not_active IP Right Cessation
- 1974-02-15 SE SE7402040A patent/SE417266B/xx not_active IP Right Cessation
- 1974-02-16 RO RO7770674A patent/RO63017A/fr unknown
- 1974-02-16 BG BG025814A patent/BG20581A3/xx unknown
- 1974-02-16 SU SU1998221A patent/SU496729A3/ru active
- 1974-02-16 JP JP49019036A patent/JPS5821601B2/ja not_active Expired
1975
- 1975-02-01 PH PH15471A patent/PH11734A/en unknown

Also Published As

Publication number	Publication date
ES423013A1 (es)	1976-04-16
SU496729A3 (ru)	1975-12-25
DE2407289C2 (de)	1984-01-26
IE38787B1 (en)	1978-06-07
GB1461313A (en)	1977-01-13
AR200674A1 (es)	1974-11-29
BR7401142D0 (pt)	1974-09-10
RO63017A (fr)	1978-05-15
CH592453A5 (fr)	1977-10-31
CA1010882A (en)	1977-05-24
IE38787L (en)	1974-08-16
JPS5821601B2 (ja)	1983-05-02
AU6490974A (en)	1975-07-31
SE417266B (sv)	1981-03-09
NL179443B (nl)	1986-04-16
PH11734A (en)	1978-05-30
DD110865A5 (fr)	1975-01-12
DK141982C (fr)	1981-02-16
ATA118674A (de)	1977-02-15
FR2218096A1 (fr)	1974-09-13
GB1461312A (en)	1977-01-13
AT339491B (de)	1977-10-25
DE2407289A1 (de)	1974-08-22
NL7402164A (fr)	1974-08-20
FR2218096B1 (fr)	1977-06-03
JPS49110674A (fr)	1974-10-22
BG20581A3 (bg)	1975-12-05
IT1054160B (it)	1981-11-10
NL179443C (nl)	1986-09-16

Publication	Publication Date	Title
US4105431A (en)	1978-08-08	3-Isothiazolones as biocides
US4265899A (en)	1981-05-05	Cosmetic formulation comprising 3-isothiazolones
US5593681A (en)	1997-01-14	Glycine anhydride dimethylol as a biocide and preservative
US4252694A (en)	1981-02-24	Cleaning composition containing 3-isothiazolones
JP4681693B2 (ja)	2011-05-11	食品用殺菌剤
WO1981001516A1 (fr)	1981-06-11	Commande de la mastite et compositions utilisees pour ce procede
NO174992B (no)	1994-05-09	Mikrobiocid preparat og anvendelse derav til ihibering av vekst av bakterier, sopp og alger
EP0032500A1 (fr)	1981-07-29	Compositions de conservation.
GB2300565A (en)	1996-11-13	Antimicrobial agent containing quaternary ammonium salt
JP7188558B2 (ja)	2022-12-13	バイオフィルム処理剤及びバイオフィルム処理方法
FR2667220A1 (fr)	1992-04-03	Composition d'agent nettoyant-decontaminant notamment pour instruments chirurgicaux.
DK141982B (da)	1980-08-04	Antimikrobielt konserveringsmiddel, især til brug i kosmetiske cremer.
JPH02134302A (ja)	1990-05-23	抗菌組成物及びその使用方法
NO872142L (no)	1987-11-23	Stoff, farmasoeytisk eller kosmetisk blanding samt fremgangsmaater ved fremstilling derav.
TW202128966A (zh)	2021-08-01	洗淨劑組成物及變色抑制方法
US3459534A (en)	1969-08-05	Methods of controlling bacteria,fungi,nematodes and weed pests with tetrahalohydroxybenzamides
US3265563A (en)	1966-08-09	Phenyl nu-alkyl thiolcarbamate microbiocide
US4025533A (en)	1977-05-24	5-Bromo-5-nitro-2-alkylsubstituted-1,3-dioxane
US3072525A (en)	1963-01-08	Fungicidal composition comprising a salicylate and a pyrazole
Buchanan	1965	Patterns of surfactant toxicity to plant tissues
US3321524A (en)	1967-05-23	1-anilino-1-(2-chloro-6-hydroxy-p-tolyl)-14-[2, 4, 6-trichloro-3-{2-hydroxy-3-<2, 4, 6-trichloro-3-[2-hydroxy-3-(2, 4, 6-trichlorophenoxy)propyl]phenoxy>propyl}phenoxy]
US3151024A (en)	1964-09-29	S-[2-(nu-oxy) pyridyl] thiolcarbonates
KR19990067408A (ko)	1999-08-16	살균 화합물(b)
GB2308812A (en)	1997-07-09	Antiseptic compositions
JPH02231487A (ja)	1990-09-13	置換グアニジン及びアミジン化合物，並びにその製造方法