US3186906A - Processes for disinfecting nonperishable articles - Google Patents
Processes for disinfecting nonperishable articles Download PDFInfo
- Publication number
- US3186906A US3186906A US194982A US19498262A US3186906A US 3186906 A US3186906 A US 3186906A US 194982 A US194982 A US 194982A US 19498262 A US19498262 A US 19498262A US 3186906 A US3186906 A US 3186906A
- Authority
- US
- United States
- Prior art keywords
- articles
- disinfected
- ester
- disinfecting
- diethyl
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 19
- 230000000249 desinfective effect Effects 0.000 title description 4
- -1 DIBUTYL Chemical compound 0.000 claims description 19
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 9
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004659 sterilization and disinfection Methods 0.000 claims description 6
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical compound CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004753 textile Substances 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000007799 cork Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 210000004666 bacterial spore Anatomy 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/20—Gaseous substances, e.g. vapours
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
Description
United States Patent 3,186,906 PROCESSES FOR DISINFECTING NON- PERISHABLE ARTICLES Hermann Genth and Otto Pauli, Krefeld-Bockum,
Germany, assignors to Farbenfabriken Bayer Aktiengesellsehaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed May 15, 1962, Ser. No. 194,982 Claims priority, appli%atigGermany, May 25, 1961,
11 Claims. r. nan-ass 3 sired side effects occur.
We have now found, surprisingly, that pyrocarbonic acid esters are not only elfective as preservatives, i.e., as agents which inhibit bacterial growth, but that they are also fungicidal and have a disinfecting effect. The principal object of the present invention is to provide a process for disinfecting articles of all kinds, such as textiles, packing materials and containers, in which process the articles are treated with pyrocarbonic acid esters.
As a rule, a comparatively short period of time is necessary for the pyrocarbonic esters completely to destroy the bacteria on the articles to be disinfected or, at the very least, to reduce the bacterial count to a value which is, in practice, of no significance.
Examples of pyrocarbonic acid esters which may be used in the processes of the present invention are the dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, diisobutyl, diamyl, dissoamyl, dicyclohexyl, diphenyl, dibenzyl and difurfuryl esters, as well as mixed esters, such as the 2,3-dichlorophenyl ethyl ester and the 3.5-dichlorophenyl benzyl ester.
If personal linen, bed linen, containers or packing materials are to be treated, then the use of the diethyl ester is again of advantage since it decomposes into carbon dioxide and the harmless ethanol.
The articles to be treated can, for example, be sprayed with a pyrocarbonic acid ester of the kind mentioned, dipped into the ester or brought into contact with compositions which contain the pyrocarbonic acid esters, for example, aqueous alcoholic solutions or aqueous dispersions, or with gaseous mixtures of the vapors of the esters ani other gases, such as carbon dioxide, nitrogen or air, Aqueous dispersions can be easily and quickly produced in a short time, for example, with the help of a rapid stirrer and, possibly, with the addition of a wetting or dispersing agent.
Thus, for example, blankets, linen materials, bed linen, packing foils, bags, containers, such as flasks and bottles, metal caps or closures, and cork, rubber or synthetic plastic stoppers for bottles and other containers, can readily be freed from bacteria and/or disinfected. Articles which can be disinfected in the process of the present invention may be formed of metals, such as aluminum, zinc, tin and galvanized or tinned iron, wood and also of synthetic plastics, such as polyethylene, polyamides or polyesters.
The following examples in which the parts mentioned 3,l36,90h Patented June 1, 1965 ice are parts by weight, are given for the purpose of illustrating the present invention:
Example 1 Aluminum casks which are intended for the storage and shipment of beverages and are to be disinfected before being re-used, are filled with a cleaning solution consisting of parts water and 10 parts ethanol. 0.5% pyrocarbonic acid diethyl ester is added and is mixed with the ethanol. After allowing the cask and the solution to stand for about 30 seconds, the initial bacterial count of 8x10 to 10x10 drops to a bacterial count of 1X10 per milliliter of the cleaning solution which is, in practice, insignificant. After rinsing out with clear water, bacterial spores which previously were present were no longer detectable in the beverage with which the cask was filled.
Example 2 Swatches of a blanket (4 x 4 cm.) are infected with a culture of each of two test bacteria (Staphylococcus azcrews and Escherichia coli). After drying at 37 C. a solution of 90 parts water, 9.5 parts ethanol and 0.5 part pyrocarbonic acid diethyl ester are brought into and maintained in contact with the swatches for various dilferent periods of time. The addition of a trace of a wetting agent (alkylaryl sulphonate) has an advantageous elfect. In the case of a period of 10 or 20 minutes contact time of the solution with the infected swatches, a definite killing of the test bacteria can be observed. (For testing purposes, the swatches were placed and incubated at a temperature of 37 C. on the surface of a nutrient medium, the swatches were turned over after 24 hours and placed on a fresh surface of the nutrient medium, in accordance with the method of H. Ostertag that was published in Melliand Textilberichte, vol. 41, pages 763 to 768 (1960).)
It is also possible to kill the mentioned test bacteria on textile materials by diluting vapors of diethylpyrocar bonate with pressurized air in a volume ratio of 12:88 and introducing the gaseous mixture, with the help of a spray device, into a closed chamber in which are contained the infected textiles. In this manner, a contact time of 5-10 hours suffices for the killing, i.e., for complete disinfection. Any diethyl pyrocarbonate which has not reacted hydrolytically with the water already contained in the textile can easily be decomposed into carbon dioxide and ethanol by blowing water vapor into the disinfection chamber. The drying of the textile takes place in the usual manner.
Example 3 Polyethylene tubes are rinsed with a solution of 90 parts water, 9.4 parts ethanol, 0.5 part pyrocarbonic acid diethyl ester and 0.1 part of an emulsifier (an alkylaryl sulphonate). Subsequently, a cosmetic having an egg yoke base was stored for 28-34 days in these rinsed tubes without any sign of fermentation and decomposition.
Example 4 Cork stoppers which are intended for use as closures for fruit juice bottles are sprayed shortly before use in a polyethylene container with diethyl py-rocarbonate or with a solution of diethyl pyrocarbonate in pure ethanol. A pressure container provided with a valve serves for the evaporation of the diethyl pyrocarbonate or ethanol solution of diethyl pyrocarbonate. By shaking up the cork stoppers in the container, all the stoppers are brought into intimate contact with the vapors of the diethyl pyrocarbonate or ethanol solution of diethyl pyrocarbonate. Growth or cultivation of bacteria or fungi in bottles closed with stoppers treated in this manner 3 does not occur. In a control series of bottles which were closed with untreated stoppers between 5 and 18% of the bottles containing a beverage were cloudy and the growth of surface bacteria and bacterial growth on the cork were definitely observed.
We claim: I
1. A process for the disinfection of non-perishable articles which comprises bringing said non-perishable articles that are to be disinfected into contact with an ester of pyrocarbonic acid of the group consisting of the dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, diisobutyl, diamyl, diisoamyl, dicyclohexyl, diphenyl, dibenzyl, difurfuryl, 2,3-dichlorophenyl ethyl, and 2,5-dichlorophenyl benzyl pyrocarbonate.
2. A process as defined in claim 1 in which the article to be disinfected is brought into contact with a solution in aqueous ethanol of an ester of pyrocarbonic acid as defined in claim 1.
3. A process as defined in claim 1 in which the article to be disinfected is brought into contact with an aqueous dispersion of an ester of pyrocarbonic acid as defined in claim 1 containing an emulsifying agent.
4. A process as defined in claim 3 in whichthe emulsifying agent is an alkyl aryl sulf'onate.
5. A process as defined in claim 1 in which the'article to be disinfected is brought into contact with a vapor consisting of an ester of pyrocarbonic acid as defined in claim 1 and a gas of the group consisting of carbon dioxide, nitrogen, and air.
6. A process as defined in claim 1 in which the article to be disinfected is brought into contact with diethyl pyrocarbonate.
7. A process for the disinfection of the surfaces of non-perishable articles which comprises bringing said nonperishable articles that are to be disinfected into contact with an aqueous solution containing 10% by Weight of ethanol and 0.5% by weight of diethyl pyrocarbonate for a period of at least 30 seconds. q
S. A process for the disinfection of the surfaces of non-perishable articles which comprises rinsing said nonperishable articles to be disinfected with an aqueous solution' containing 9.4% by weight of ethanol, 0.5% by weight of diethyl pyrocarbonate and 0.1% by weight of an alkylaryl sulfonate emulsifying agent.
9. The process of claim 1 wherein the non-perishable articles are textiles.
10. The process of claim 1 wherein the non perishable articles are packing materials. a
11. The process of claim 1 wherein the non-perishable" articles are containers.
References Cited by the Examiner UNITED STATES PATENTS 1,599,809 9/26 Cohen et al. 16722 2,317,378 4/43 Harris 16722 2,651,590 9/53 Karsten 167--22 2,885,319 5/59 Ligett et al. 16738.5 2,910,400 10/59 Bernhard et al. 167-22 3,058,877 10/62 Musser 16738.5
OTHER REFERENCES Sargarin: Cosmetics, Science and Technology, Interscience Publishers, Inc., New York 1957, pages 1034- 1037.
LEWIS GOTTS, Primary Examiner.
JULIAN S. LEVITT, Examiner.
Claims (1)
1. A PROCESS FOR THE DISINFECTION OF NON-PERISHABLE ARTICLES WITH COMPRISES BRINGING SAID NON-PERISHABLE ARTICLES THAT ARE TO BE DISINFECTED INTO CONTACT WITH AN ESTER OF PYROCARBONIC ACID OF THE GROUP CONSISTING OF THE DIMETHYL , DIETHYL, DIPROPYL, DIISOPROPYL, DIBUTYL, DIISOBUTYL, DIAMYL, DIISOAMYL, DICYCLOHEXYL, DIPHENYL, DIBENZYL, DIFURFURYL, 2,3-DICHLOROPHENYL ETHYL, AND 2,5-DICHLOROPHENYL BENZYL PYROCARBONATE.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0034011 | 1961-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3186906A true US3186906A (en) | 1965-06-01 |
Family
ID=7095365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US194982A Expired - Lifetime US3186906A (en) | 1961-05-25 | 1962-05-15 | Processes for disinfecting nonperishable articles |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3186906A (en) |
| CH (1) | CH408289A (en) |
| GB (1) | GB956629A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936269A (en) * | 1974-11-25 | 1976-02-03 | Logica International Corporation | Method of cold sterilization using frozen dimethyl dicarbonate |
| US4087543A (en) * | 1975-02-15 | 1978-05-02 | Bayer Aktiengesellschaft | Composition for disinfecting soil and combating plant diseases containing organic dicarbonates |
| US4930731A (en) * | 1987-05-06 | 1990-06-05 | Coors Porcelain Company | Dome and window for missiles and launch tubes with high ultraviolet transmittance |
| US4983555A (en) * | 1987-05-06 | 1991-01-08 | Coors Porcelain Company | Application of transparent polycrystalline body with high ultraviolet transmittance |
| US5082739A (en) * | 1988-04-22 | 1992-01-21 | Coors Porcelain Company | Metallized spinel with high transmittance and process for producing |
| US5244849A (en) * | 1987-05-06 | 1993-09-14 | Coors Porcelain Company | Method for producing transparent polycrystalline body with high ultraviolet transmittance |
| WO2007134710A1 (en) * | 2006-05-18 | 2007-11-29 | Lanxess Deutschland Gmbh | Stabilization of dicarbonic diesters by finely divided solids |
| WO2019097005A1 (en) * | 2017-11-20 | 2019-05-23 | Lanxess Deutschland Gmbh | Aluminum container containing dicarbonate |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1599809A (en) * | 1926-09-14 | Jtoxfljff s | ||
| US2317378A (en) * | 1941-02-05 | 1943-04-27 | Benjamin R Harris | Antiseptic materials |
| US2651590A (en) * | 1951-04-13 | 1953-09-08 | Vanderbilt Co R T | Fumigant composition and process |
| US2885319A (en) * | 1953-12-17 | 1959-05-05 | Pittsburgh Coke And Chemical C | N-phenylmaleamic acid esters as fungicides |
| US2910400A (en) * | 1956-04-13 | 1959-10-27 | Bayer Ag | Process of preserving carbohydratecontaining perishable material |
| US3058877A (en) * | 1960-09-09 | 1962-10-16 | Chicopee Mfg Corp | Germicidal, bactericidal and fungicidal compositions |
-
1962
- 1962-03-28 CH CH371562A patent/CH408289A/en unknown
- 1962-03-28 GB GB11887/62A patent/GB956629A/en not_active Expired
- 1962-05-15 US US194982A patent/US3186906A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1599809A (en) * | 1926-09-14 | Jtoxfljff s | ||
| US2317378A (en) * | 1941-02-05 | 1943-04-27 | Benjamin R Harris | Antiseptic materials |
| US2651590A (en) * | 1951-04-13 | 1953-09-08 | Vanderbilt Co R T | Fumigant composition and process |
| US2885319A (en) * | 1953-12-17 | 1959-05-05 | Pittsburgh Coke And Chemical C | N-phenylmaleamic acid esters as fungicides |
| US2910400A (en) * | 1956-04-13 | 1959-10-27 | Bayer Ag | Process of preserving carbohydratecontaining perishable material |
| US3058877A (en) * | 1960-09-09 | 1962-10-16 | Chicopee Mfg Corp | Germicidal, bactericidal and fungicidal compositions |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936269A (en) * | 1974-11-25 | 1976-02-03 | Logica International Corporation | Method of cold sterilization using frozen dimethyl dicarbonate |
| US4087543A (en) * | 1975-02-15 | 1978-05-02 | Bayer Aktiengesellschaft | Composition for disinfecting soil and combating plant diseases containing organic dicarbonates |
| US4930731A (en) * | 1987-05-06 | 1990-06-05 | Coors Porcelain Company | Dome and window for missiles and launch tubes with high ultraviolet transmittance |
| US4983555A (en) * | 1987-05-06 | 1991-01-08 | Coors Porcelain Company | Application of transparent polycrystalline body with high ultraviolet transmittance |
| US5244849A (en) * | 1987-05-06 | 1993-09-14 | Coors Porcelain Company | Method for producing transparent polycrystalline body with high ultraviolet transmittance |
| US5082739A (en) * | 1988-04-22 | 1992-01-21 | Coors Porcelain Company | Metallized spinel with high transmittance and process for producing |
| WO2007134710A1 (en) * | 2006-05-18 | 2007-11-29 | Lanxess Deutschland Gmbh | Stabilization of dicarbonic diesters by finely divided solids |
| US20090140208A1 (en) * | 2006-05-18 | 2009-06-04 | Lanxess Deutschland Gmbh | Aqueous carbon black formulations for ink jet |
| WO2019097005A1 (en) * | 2017-11-20 | 2019-05-23 | Lanxess Deutschland Gmbh | Aluminum container containing dicarbonate |
| US20200277129A1 (en) * | 2017-11-20 | 2020-09-03 | Lanxess Deutschland Gmbh | Aluminum Container Containing Dicarbonate |
Also Published As
| Publication number | Publication date |
|---|---|
| GB956629A (en) | 1964-04-29 |
| CH408289A (en) | 1966-02-28 |
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