WO2007075281A1 - Denaturant for ethanol - Google Patents
Denaturant for ethanol Download PDFInfo
- Publication number
- WO2007075281A1 WO2007075281A1 PCT/US2006/046561 US2006046561W WO2007075281A1 WO 2007075281 A1 WO2007075281 A1 WO 2007075281A1 US 2006046561 W US2006046561 W US 2006046561W WO 2007075281 A1 WO2007075281 A1 WO 2007075281A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- chlorhexidine
- ethanol
- denaturant
- concentration
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 125
- 239000003398 denaturant Substances 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 35
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960003260 chlorhexidine Drugs 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940123208 Biguanide Drugs 0.000 claims abstract description 7
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical class CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 claims description 9
- 229960003333 chlorhexidine gluconate Drugs 0.000 claims description 8
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 claims description 8
- 229950010221 alexidine Drugs 0.000 claims description 6
- WJLVQTJZDCGNJN-UHFFFAOYSA-N Chlorhexidine hydrochloride Chemical compound Cl.Cl.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WJLVQTJZDCGNJN-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims description 2
- 229960002152 chlorhexidine acetate Drugs 0.000 claims description 2
- 229960004504 chlorhexidine hydrochloride Drugs 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- 229940001447 lactate Drugs 0.000 claims description 2
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 claims description 2
- 229960004329 metformin hydrochloride Drugs 0.000 claims description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 2
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 claims description 2
- 229940075894 denatured ethanol Drugs 0.000 abstract description 7
- 235000019441 ethanol Nutrition 0.000 description 36
- KUXUALPOSMRJSW-IFWQJVLJSA-N 2-[6-[[amino-[[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 KUXUALPOSMRJSW-IFWQJVLJSA-N 0.000 description 11
- 230000000845 anti-microbial effect Effects 0.000 description 9
- 239000011928 denatured alcohol Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 3
- 150000004283 biguanides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000011012 sanitization Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- 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
- A61P31/02—Local antiseptics
-
- 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
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
Abstract
A denatured ethanol composition is provided, the composition consisting essentially of: ethanol and a denaturant selected from the group consisting of chlorhexidine and salts thereof, biguanide and combinations of two or more of the foregoing; and optionally, water.
Description
DENATURANT FOR ETHANOL
The invention relates to ethanol comprising a denaturant and to products comprising the denatured ethanol.
Background
Ethyl alcohol or ethanol is used as an ingredient in any of a number of products that are not intended for consumption. In some products, ethanol is a solvent in which various compositional components are dissolved. Ethanol is often used in the preparation of cosmetics for its solvent properties, or in the formulation of sanitizing compositions for its antimicrobial properties, for example. Because such products are not intended to be ingested, the ethanol used in such products is typically denatured so that it is rendered undrinkable. Moreover, governmental authorities often impose taxes on commercial shipments of pure ethanol (e.g., 190 or 200 proof) even if the ethanol is intended for industrial uses such an ingredient in the aforementioned cosmetic or antimicrobial products.
A number of materials are available for denaturing ethyl alcohol including methanol, isopropanol, iodine, formaldehyde solution, phenylethyl alcohol, chloroform and diethyl phthalate. The known denaturants have several disadvantages that can lower the quality of the product they are associated with. Diethyl phthalate, for example, is known to cause sneezing when used in aerosol formulations. Other denaturants, such as isopropanol and methyl isobutyl ketone, influence the odor character of perfumed products and some of them are known to be color-unstable. Some denaturants (e.g., methanol, iodine, formaldehyde, chloroform) are potentially hazardous to handle and can be toxic if consumed.
Summary
The present invention provides a composition in the form of a denatured alcohol. In a first aspect, the composition consists essentially of: Ethanol;
A denaturant selected from the group consisting of chlorhexidine and salts thereof, biguanide and combinations of two or more of the foregoing; and
Optionally, water.
In another aspect, the invention provides a composition that consists essentially of:
Ethanol;
Chlorhexidine Gluconate; and Optionally, water.
Those skilled in the art will further appreciate the various aspects of the invention upon reviewing the remainder of the disclosure, including the detailed description of the various embodiments and the appended claims.
Detailed Description
The present invention provides materials suitable for use as ethanol denaturants. The materials described herein, while useful as denaturants, do not possess the hazardous properties of denaturants that are already known and used. Moreover, denatured alcohol of the invention can be incorporated into other compositions in which the denatured alcohol will provide additional antimicrobial or antiseptic character.
Denaturants suitable for use in the present invention include chlorhexidine and salts thereof. Suitable chlorhexidine salts include without limitation chlorhexidine gluconate, chlorhexidine lactate, chlorhexidine acetate, chlorhexidine isobutyrate, chlorhexidine glucoheptonate, chlorhexidine methanesulphonate and chlorhexidine hydrochloride. Other suitable denaturants include biguanides such as metformin hydrochloride as well as alexidine salts (l,r-Hexamethylene-bis[5-(2-
ethylhexyl)biguanide]) such as alexidine dihydrochloride, alexidine dihydrofloride and alexidine diacetate. Combinations of two or more of the foregoing denaturants are also contemplated.
In embodiments of the invention, chlorhexidine gluconate ("CHG") is used as the denaturant without adding to the safety hazards of the alcohol to those in the workplace or to a potential abuser. CHG is often used as an antiseptic agent. While CHG has been used in cleansers, for surgical scrubs, for treating skin wounds, as a germicidal hand rinse and as an antibacterial dental rinse, it has previously been unrecognized as a denaturant for ethanol. CHG is well suited as a denaturant because it is highly soluble in alcoholic solutions, has a low toxicity and possesses an ability to bind to mucosal tissues in the mouth to provide a persistently unpleasant bitter taste.
In the foregoing embodiments, CHG as well as other chlorhexidine salts can be used as a denaturant while also providing additional benefits as an antimicrobial and preservative. Thus, the chlorhexidine salts are useful in first providing utility as a denaturant and thereafter being useful as an antimicrobial in a composition that incorporates the denatured ethanol as a component. In other words, compositions that include ethanol and CHG, for example, as individual components, could be formulated with denatured alcohol as a source for the ethanol and the CHG components.
In embodiments of the invention, biguanide compounds are used for denaturing ethanol. Biguanides also exhibit germicidal and antimicrobial activities. With certain types of substituents, the compositions are also useful as components of hair-care products and other items of personal hygiene.
In addition to providing a bitter and unpleasant taste, the denaturants described herein can, upon repeated exposure, stain or discolor teeth, and simple tooth brushing is generally ineffective in removing the stain. This additional effect provides another incentive to not abuse alcohol products denatured with these agents, and it potentially serves as an indicator of those who have abused the denatured alcohol.
The compositions according to the invention can be prepared by mixing the individual components. Denaturants used in the present invention can be added to 190 to 200 proof ethanol to provide a final denaturant concentration of at least about 0.01% by weight. In some embodiments, the concentration of the denaturant may be within the range from about 0.01% to about 20 % by total weight. In other embodiments, the final denaturant concentration may fall within the range from about 0.08 % to about 1.5 % by total weight. The determination of the fitness (or unfitness) of an ethanol / denaturant solution according to the present invention may be made according to the methods set forth, for example, in 27 CFR 17.134 which provides, in part, that a product's unfitness for beverage purposes may be determined by organoleptic examination. In such an examination, the product may be diluted with water to an alcoholic concentration of 15% and tasted. Other methods for the determination of a products fitness for beverage purposes may also be employed.
The denatured ethanol of the invention can be further used in the preparation of other products that require ethanol and the denaturant as components thereof. These products may comprise from 1 to 99% by weight of the denatured ethanol. In some embodiments, the denatured alcohol may be a component in a sanitizing lotion, for example, that requires ethanol and denaturant, although the denaturant may be required for its antimicrobial properties in the sanitizing lotion. In some embodiments, the denatured alcohol may be a component in a cosmetic product that requires ethanol and denaturant, although the denaturant may be useful for its antimicrobial properties in the cosmetic. In formulating these other products, the denatured alcohol may simply be added to the other components of the product formulation to provide the ethanol and denaturant at concentrations needed for the particular product. Those skilled in the art will appreciate that the concentration of the denaturant in the ethanol composition may be supplemented with additional denaturant to bring the concentration of the denaturant to the level needed for antimicrobial efficacy, for example.
EXAMPLES
Additional features of the embodiments of the invention are further described in the following non-limiting examples. Unless indicated otherwise, all parts and percentages are on a weight basis.
Components used in formulations described in the various Examples are listed in
Table 1.
Table 1 Components
1. British Pharmacopoeia
Examples 1-3, Comparative Examples A, B and C
The ethanol solutions of Examples 1-4 and Comparative Examples A and B were prepared by adding the components listed in Table 1 according to the amounts listed in Table 2 to a clean glass container. The solutions were mixed by shaking. A determination of unfitness for beverage purposes was made for each of the ethanol solutions by organoleptic examination, as described in 27 CFR 17.134, by tasting samples of the product diluted with water to an alcohol concentration of 15% by volume. Two individuals, one male, one female, tasted 0.5 grams of each of the ethanol solutions to demonstrate the effectiveness of the identified denaturant.
The compositions and the taste observations of the various ethanol solutions are set forth in Table 2.
Table 2 Examples 1-3 and Comparative Examples A, B and C
Examples 4-6
The Examples presented in Table 3 represent the amounts and concentrations for the process of denaturing 100 gallons (378.5 liters) of 190 proof ethanol ("EtOH") at three different levels of CHG. For instance, Example 6 was prepared by adding 1.23 kg of 20% w/v CHG to 100 gallons (378.5 liters) of 190 proof ethanol. This resulted in a solution of denatured ethanol with 285 kg pure ethanol, 24.3 kg of water and a concentration of 0.08 % w/w CHG. If the ethanol solutions of Examples 4-6 were diluted down to 15% v/v ethanol as permitted under 27 CFR 17.134 ("Determination of unfitness for beverage purposes"), the resulting CHG concentrations in the diluted solutions would be 0.10% w/w, 0.05% w/w and 0.01%w/w, respectively.
Table 3 Examples Denatured Ethanol Formulations
The present invention has been described with reference to embodiments thereof. It will be apparent by those skilled in the art that changes, modifications or additions can be made to the described embodiments without departing from the scope of the present invention.
Claims
1. A composition, consisting essentially of: ethanol; a denaturant selected from the group consisting of chlorhexidine and salts thereof, biguanide and combinations of two or more of the foregoing; and optionally, water.
2. The composition of claim 1 wherein the chlorhexidine salts are selected from the group consisting of chlorhexidine gluconate, chlorhexidine lactate, chlorhexidine acetate, chlorhexidine isobutyrate, chlorhexidine glucoheptonate, chlorhexidine methanesulphonate, chlorhexidine hydrochloride and combinations of two or more of the foregoing.
3. The composition of claim 1 wherein the biguanide is selected from the group consiting of metformin hydrochloride, alexidine salts and combinations of two or more of the foregoing.
4. The composition of claim 3 wherein the alexidine salts are selected from the group consisting of alexidine dihydrochloride, alexidine dihydrofloride, alexidine diacetate and combinations of two or more of the foregoing.
5. The composition of claim 1 wherein the denaturant is present in the composition at a concentration of at least about .01% by weight.
6. The composition of claim 1 wherein the denaturant is present in the composition at a concentration in the range between .01% and 20% by weight.
7. The composition of claim 1 wherein the denaturant is present in the composition at a concentration in the range between .08% and 1.5% by weight.
8. A composition, consisting essentially of: ethanol; chlorhexidine gluconate; and optionally, water.
9. The composition of claim 8 wherein the chlorhexidine gluconate is present in the composition at a concentration of at least about .01% by weight.
10. The composition of claim 8 wherein the chlorhexidine gluconate is present in the composition at a concentration in the range between .01% and 20% by weight.
11. The composition of claim 8 wherein the chlorhexidine gluconate is present in the composition at a concentration in the range between .08% and 1.5% by weight.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06839099A EP1971314A1 (en) | 2005-12-21 | 2006-12-06 | Denaturant for ethanol |
| AU2006329961A AU2006329961A1 (en) | 2005-12-21 | 2006-12-06 | Denaturant for ethanol |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/314,761 | 2005-12-21 | ||
| US11/314,761 US20070138439A1 (en) | 2005-12-21 | 2005-12-21 | Denaturant for ethanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2007075281A1 true WO2007075281A1 (en) | 2007-07-05 |
Family
ID=38172410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2006/046561 WO2007075281A1 (en) | 2005-12-21 | 2006-12-06 | Denaturant for ethanol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070138439A1 (en) |
| EP (1) | EP1971314A1 (en) |
| CN (1) | CN101340890A (en) |
| AU (1) | AU2006329961A1 (en) |
| TW (1) | TW200731995A (en) |
| WO (1) | WO2007075281A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2580284A4 (en) | 2010-06-09 | 2015-04-22 | Mannington Mills | Floor covering composition containing renewable polymer |
| US9970303B2 (en) | 2014-05-13 | 2018-05-15 | Entrotech, Inc. | Erosion protection sleeve |
| CA3078628A1 (en) | 2017-10-12 | 2019-04-18 | Medline Industries, Inc. | Antiseptic wipes |
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| US5968535A (en) * | 1997-04-09 | 1999-10-19 | Haarmann & Reimer Gmbh | Denaturant for ethanol |
| WO2004018003A1 (en) * | 2002-08-20 | 2004-03-04 | Alda Pharmaceuticals Corp. | A wide spectrum disinfectant |
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| US8906413B2 (en) * | 2003-05-12 | 2014-12-09 | Supernus Pharmaceuticals, Inc. | Drug formulations having reduced abuse potential |
| US7670997B2 (en) * | 2006-06-08 | 2010-03-02 | Bausch & Lomb Incorporated | Ophthalmic compositions comprising a branched, glycerol monoalkyl compound and a fatty acid monoester |
-
2005
- 2005-12-21 US US11/314,761 patent/US20070138439A1/en not_active Abandoned
-
2006
- 2006-12-06 EP EP06839099A patent/EP1971314A1/en not_active Withdrawn
- 2006-12-06 CN CNA2006800477921A patent/CN101340890A/en active Pending
- 2006-12-06 WO PCT/US2006/046561 patent/WO2007075281A1/en active Application Filing
- 2006-12-06 AU AU2006329961A patent/AU2006329961A1/en not_active Abandoned
- 2006-12-20 TW TW095147981A patent/TW200731995A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870108A (en) * | 1988-09-20 | 1989-09-26 | Page Leslie A | Liquid antiseptic composition |
| US5968535A (en) * | 1997-04-09 | 1999-10-19 | Haarmann & Reimer Gmbh | Denaturant for ethanol |
| WO2004018003A1 (en) * | 2002-08-20 | 2004-03-04 | Alda Pharmaceuticals Corp. | A wide spectrum disinfectant |
Non-Patent Citations (1)
| Title |
|---|
| TOCA-HERRERA J.L. ET AL.: "Chemical and thermal denaturation of crystalline bacterial S-layer proteins: an atomic force microscopy study", MICROSCOPY RESEARCH AND TECHNIQUES, vol. 65, no. 4/5, 3 January 2005 (2005-01-03), pages 226 - 234, XP003014897 * |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200731995A (en) | 2007-09-01 |
| AU2006329961A1 (en) | 2007-07-05 |
| CN101340890A (en) | 2009-01-07 |
| EP1971314A1 (en) | 2008-09-24 |
| US20070138439A1 (en) | 2007-06-21 |
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