US2582395A - Ointments containing oil-soluble antioxidants - Google Patents

Ointments containing oil-soluble antioxidants Download PDF

Info

Publication number
US2582395A
US2582395A US581323A US58132345A US2582395A US 2582395 A US2582395 A US 2582395A US 581323 A US581323 A US 581323A US 58132345 A US58132345 A US 58132345A US 2582395 A US2582395 A US 2582395A
Authority
US
United States
Prior art keywords
dimercaptopropanol
mercapto compound
ointment
weight
oxidant
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
Application number
US581323A
Inventor
George W Rigby
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to US581323A priority Critical patent/US2582395A/en
Application granted granted Critical
Publication of US2582395A publication Critical patent/US2582395A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels

Definitions

  • This invention relates to therapeutic compositions and more particularly it relates to ointments for arsenic therapy.
  • a number of common ointment bases such as, for example, those containing peanut oil, lanolin and the like as the vehicle for the medicament are suitable in consistency and spreading quality for the preparation of ointments containing 2,3-dimercaptopropanol as the therapeutic agent.
  • these 2,3-dimercaptopropanol ointments are susceptible to oxidation when exposed to air. Oxygen readily reacts with the thiol groups of the dimercaptopropanol to form polymeric disulfides which are therapeutically inactive. Such ointments thus lose their efiicacy on intermittent or continuous exposure to air.
  • the particular sensitivity of the dimercaptopropanol and the necessity for keeping these compositions at a precise level of therapeutic activity creates a special problem, to which the application of the general antioxidant art does not provide a solution.
  • An object of this invention is to provide more useful therapeutic compositions containing 2,3- dimercaptopropanol than have heretofore been available.
  • a further object is to provide ointments containing 2,3-dimercaptopropanol which retain their efiicacy for long periods, particularly when they are exposed to air. More specifically it is an object of this invention to retard the rate of oxidation of 2,3-dimercaptopropanol in ointments containing this therapeutic agent.
  • pure 2,3-dimercaptopropanol obtainable by the reaction of sodium hydrosulfide with glycerol dichlorohydrin, and about 0.5 to 2.0% of its weight of the oil-soluble anti-oxidant, are compounded at room temperature with a cold uniformly melt-blended oily base preferably comprising a fatty material such as peanut oil or lanolin or both.
  • the oilscluble anti-oxidants which have given the best results are the tocopherols, preferably the mixture of the several isomers available as a fish oil distillate.
  • the resulting ointments absorb oxygen at a considerably less rapid rate than similar ointments not containing an oil-soluble antioxidant.
  • One part of the ointment absorbs only 4.6 10 part of oxygen under these conditions while an equal weight of an ointment containing the same ingredients in the same proportions, with the exception that no tocopherols are present, absorbs 10 10- part of oxygen.
  • Example I The above ingredients are made up into an ointment in the manner given in Example I.
  • the examples illustrate the use of mixed tocopherols as the anti-oxidant for 2,3-dimercaptopropanol ointments.
  • the individual alpha-, beta-, and gamma-tocopherols and other oil-soluble antloxidants e. g., palmitoyl ascorbate and hydroquinone, which are not reactive with thiol groups,
  • the tocopherols are the most effective of these oil-soluble anti-oxidants. As previously indicated, they are commercially available as a 40% concentrate distilled from fish oil. More specifically, this concentrate is a distilled mixture of the alpha-, beta-, and gamma-tocopherols, and it may be used in the ointments of this invention without separation of the isomers or further purification.
  • the individual tocopherols may be used, if desired, but they have different degrees of effectiveness.
  • the alpha-tocopherol for example, is somewhat less effective than the other isomers or the commercial mixture.
  • the gamma-tocopherol is the most effective of the individual isomers.
  • the proportions of oil-soluble anti-oxidant employed in these ointments may vary over a wide range depending on the amount of 2, 3- dimercaptopropanol present and on the degree of oxygen exposure expected to be encountered. Thus, amounts ranging from 0.5% to 10.0% of the weight of the dimercaptopropanol may be used. Under mild conditions of exposure, 0.5% is sufficient, While 10.0% is required when the ointment is to be exposed to oxygen or air for long periods at relatively high temperatures. For ordinary exposures the preferred amount is 0.5% to 2.0% or" the weight of the dimercaptopropanol.
  • B-dimereaptopropanol is subject to other types of chemical transformation, such to polymeric sulfides by heat in the absence of oxygen, in contrast to disulfides formed by oxidation.
  • this type of transiormation may be minimized by careful control of water content, iron content, and pH.
  • the ointments of highest heat stability must (1) contain less than about 0.5% water, (2) contain less than 1 part per million, and preferably less than 0.5 part per million, of iron and other heavy metals, and (3) have a pH within the range of 4-5, an equilibrium value obtained with a pH meter and glass electrode on a portion of the aqueous layer obtained by treating a sample of the ointment with sufficient freshly boiled distilled Water to have a ratio or" Water to dimercaptopropanol of 99 to 1.
  • oily bases may be used in these ointments.
  • nondrying vegetable oils such as olive oil and castor oil, non-drying animal oils, or other types of non-drying oils such as mineral oils may be used if desired.
  • the ointments of this invention are of great value in neutralizing chemical warfare vesicants containin arsenic, particularly the arsines, and in arsenic and cadmium therapy in general.
  • arsenic particularly the arsines
  • arsenic and cadmium therapy in general.
  • the presence of the oil-soluble anti-oxidant renders them sufficiently inert to oxidation to permit their use under practical conditions Without excessive loss in efficacy.
  • a stable ointment comprising an oily vehicle, 2,3-dimercaptopropanol, and an oil-soluble antioxidant for the mercapto compound selected from the group consisting of tocopherol and palmitoyl ascorbate, the anti-oxidant being present in an amount of at least 0.5 per cent by weight of the said mercapto compound.
  • An anti-vesicant composition containing, 2,3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of at least 0.5 per cent by weight of the said mercapto compound.
  • An anti-vesicant composition containing, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of from 0.5-10% of the weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of at least 0.5 per cent by weight .of the said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of from 0.5-10% of the Weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of at least 0.5 per cent by weight of the said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.5-,l0% of the weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.52.0% of the weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and anti-oxidant for said mercapto compound consisting of gamma-tocopherol in an amount of at least 0.5 per cent by weight of the said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, non-dryin vegetable oils, 2, B-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.5- 10% of the weight of said mercapto compound.
  • a stable ointment as set forth in claim 9 characterized in that it-has a pH range of from 4-5 and contains less than about 0.5% water and less than 1 part per million of heavy metals.
  • a stable ointment as set forth in claim 11 characterised in that it has a pH range of from 45 and contains less than about 05% water and less than 1 part per million of heavy metals.
  • a stable ointment for arsenic and cadmium therapy containing, peanut oil, 2, 3-dimercaptopropanol, and an anti-oxdiant for said mercapto compound comprising mixed natural tocopherols in an amount of from 05-10% of the weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy containing, anhydrous lanolin, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 05-10% of the weight of said mercapto compound.
  • a stable ointment for arsenic and cadmium therapy comprising in parts by weight:
  • Peanut 011 36.95 Lanolin, anhydrous 8.00 Cetyl alcohol 10.00 Glyceryl monostearate 10.00 White petrolatum, soft 25.00 Benzyl benzoate 5.00 Mixed natural tocopherols 0.05 2, 3-dimercaptopropanol 5.00
  • a stable ointment for arsenic and cadmium therapy comprising in parts by Weight:

Description

Patented Jan. 15, 1952 OINTMENTS CONTAINING OIL- SOLUBLE AN TIOXIDAN TS George W. Rigby, Wilmington, Del., assignor, by memo assignments, to the United States of America as represented by the Secretary of War No Drawing. Application March 6, 1945, Serial No. 581,323
17 Claims.
This invention relates to therapeutic compositions and more particularly it relates to ointments for arsenic therapy.
A number of common ointment bases such as, for example, those containing peanut oil, lanolin and the like as the vehicle for the medicament are suitable in consistency and spreading quality for the preparation of ointments containing 2,3-dimercaptopropanol as the therapeutic agent. However, these 2,3-dimercaptopropanol ointments are susceptible to oxidation when exposed to air. Oxygen readily reacts with the thiol groups of the dimercaptopropanol to form polymeric disulfides which are therapeutically inactive. Such ointments thus lose their efiicacy on intermittent or continuous exposure to air. The particular sensitivity of the dimercaptopropanol and the necessity for keeping these compositions at a precise level of therapeutic activity creates a special problem, to which the application of the general antioxidant art does not provide a solution.
'An object of this invention is to provide more useful therapeutic compositions containing 2,3- dimercaptopropanol than have heretofore been available. A further object is to provide ointments containing 2,3-dimercaptopropanol which retain their efiicacy for long periods, particularly when they are exposed to air. More specifically it is an object of this invention to retard the rate of oxidation of 2,3-dimercaptopropanol in ointments containing this therapeutic agent.
These objects are accomplished by admixing with an oily vehicle the desired medicament, viz., 2,3-dimercaptopropanol, and a small amount of an oil soluble anti-oxidant, whereby there is obtained an ointment comprising these components which is useful in arsenic therapy and more stable than ointments previously available.
In the practice of the invention, pure 2,3-dimercaptopropanol, obtainable by the reaction of sodium hydrosulfide with glycerol dichlorohydrin, and about 0.5 to 2.0% of its weight of the oil-soluble anti-oxidant, are compounded at room temperature with a cold uniformly melt-blended oily base preferably comprising a fatty material such as peanut oil or lanolin or both. The oilscluble anti-oxidants which have given the best results are the tocopherols, preferably the mixture of the several isomers available as a fish oil distillate. The resulting ointments absorb oxygen at a considerably less rapid rate than similar ointments not containing an oil-soluble antioxidant.
The following examples illustrate the invention in greater detail.
In these examples proportions of ingredients are expressed as parts by weight unless otherwise specified.
Mixed natural tocopherols (4.0%) 0.05 2,3-dimercaptopropanol 5.00
All the above ingredients with the exception of the last two mentioned are heated together until a uniform melt is obtained. This melt is cooled with stirring to room temperature, and the tocopherols and 2,3-dimercaptopropanol then Worked into it with a spatula, putty knife, or an appropriate mechanical mixer designed for handling pasty masses. A composition useful for external arsenic therapy is obtained. Its 10W oxidation susceptibility is shown by the following test. An accurately weighed sample of the ointment is stored under pure oxygen at 50 C. and atmospheric pressure, and the amount of oxygen absorbed is measured after 48 hours. One part of the ointment absorbs only 4.6 10 part of oxygen under these conditions while an equal weight of an ointment containing the same ingredients in the same proportions, with the exception that no tocopherols are present, absorbs 10 10- part of oxygen.
Example II Parts Lanolin, anhydrous 80.0 Benzyl benzoate 10.0 Mixed natural tocopherols (40%) 0.1 2,3-dimercaptopropanol I- 10.0
The above ingredients are made up into an ointment in the manner given in Example I. One part of this ointment when tested as described in Example I, absorbs 2.7 l0- part of oxygen on exposure to pure oxygen for 48 hours at 50 C. A control ointment containing no added tocopherols absorbs 15.7 10- part of oxygen.
The examples illustrate the use of mixed tocopherols as the anti-oxidant for 2,3-dimercaptopropanol ointments. Instead of the mixed tocopherols, the individual alpha-, beta-, and gamma-tocopherols and other oil-soluble antloxidants, e. g., palmitoyl ascorbate and hydroquinone, which are not reactive with thiol groups,
may be used. The tocopherols are the most effective of these oil-soluble anti-oxidants. As previously indicated, they are commercially available as a 40% concentrate distilled from fish oil. More specifically, this concentrate is a distilled mixture of the alpha-, beta-, and gamma-tocopherols, and it may be used in the ointments of this invention without separation of the isomers or further purification. The individual tocopherols may be used, if desired, but they have different degrees of effectiveness. The alpha-tocopherol, for example, is somewhat less effective than the other isomers or the commercial mixture. The gamma-tocopherol is the most effective of the individual isomers.
The proportions of oil-soluble anti-oxidant employed in these ointments may vary over a wide range depending on the amount of 2, 3- dimercaptopropanol present and on the degree of oxygen exposure expected to be encountered. Thus, amounts ranging from 0.5% to 10.0% of the weight of the dimercaptopropanol may be used. Under mild conditions of exposure, 0.5% is sufficient, While 10.0% is required when the ointment is to be exposed to oxygen or air for long periods at relatively high temperatures. For ordinary exposures the preferred amount is 0.5% to 2.0% or" the weight of the dimercaptopropanol.
2, B-dimereaptopropanol is subject to other types of chemical transformation, such to polymeric sulfides by heat in the absence of oxygen, in contrast to disulfides formed by oxidation. In the present ointments, this type of transiormation may be minimized by careful control of water content, iron content, and pH. More specifically, the ointments of highest heat stability must (1) contain less than about 0.5% water, (2) contain less than 1 part per million, and preferably less than 0.5 part per million, of iron and other heavy metals, and (3) have a pH within the range of 4-5, an equilibrium value obtained with a pH meter and glass electrode on a portion of the aqueous layer obtained by treating a sample of the ointment with sufficient freshly boiled distilled Water to have a ratio or" Water to dimercaptopropanol of 99 to 1. These factors are controlled by (1) use of only anhydrous ingredients, (2) use of ingredients together containing less than the above-specified quantity of heavy metals, and formulating the ointments in vessels WhiCh'dO not introduce any more of these metals, and (3) the use of ingredients having a neutral or slightly acid reaction or by adding suflicient acid to the f nal ointment to bring its pH Within the preferred range.
In place of the specific oily vehicles disclosed in the examples, other oily bases may be used in these ointments. For example, other nondrying vegetable oils such as olive oil and castor oil, non-drying animal oils, or other types of non-drying oils such as mineral oils may be used if desired.
The ointments of this invention are of great value in neutralizing chemical warfare vesicants containin arsenic, particularly the arsines, and in arsenic and cadmium therapy in general. The presence of the oil-soluble anti-oxidant renders them sufficiently inert to oxidation to permit their use under practical conditions Without excessive loss in efficacy.
Having thus described my invention, what I claim as new and wish to secure by Lette s Patent is:
l. A stable ointment comprising an oily vehicle, 2,3-dimercaptopropanol, and an oil-soluble antioxidant for the mercapto compound selected from the group consisting of tocopherol and palmitoyl ascorbate, the anti-oxidant being present in an amount of at least 0.5 per cent by weight of the said mercapto compound.
2. An anti-vesicant composition containing, 2,3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of at least 0.5 per cent by weight of the said mercapto compound.
3. An anti-vesicant composition containing, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of from 0.5-10% of the weight of said mercapto compound.
4. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of at least 0.5 per cent by weight .of the said mercapto compound.
5. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising tocopherol in an amount of from 0.5-10% of the Weight of said mercapto compound.
6. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of at least 0.5 per cent by weight of the said mercapto compound.
2'. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.5-,l0% of the weight of said mercapto compound.
8. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.52.0% of the weight of said mercapto compound.
9. A stable ointment for arsenic and cadmium therapy containing, non-drying oils, 2, 3-dimercaptopropanol, and anti-oxidant for said mercapto compound consisting of gamma-tocopherol in an amount of at least 0.5 per cent by weight of the said mercapto compound.
10. A stable ointment for arsenic and cadmium therapy containing, non-dryin vegetable oils, 2, B-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.5- 10% of the weight of said mercapto compound.
11. A stable ointment as set forth in claim 9 characterized in that it-has a pH range of from 4-5 and contains less than about 0.5% water and less than 1 part per million of heavy metals.
12. A stable ointment for arsenic and cadmium therapy containing, non-drying animal oils,
, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 0.5- 10% of the weight of said mercapto compound.
13. A stable ointment as set forth in claim 11 characterised in that it has a pH range of from 45 and contains less than about 05% water and less than 1 part per million of heavy metals. 14. A stable ointment for arsenic and cadmium therapy containing, peanut oil, 2, 3-dimercaptopropanol, and an anti-oxdiant for said mercapto compound comprising mixed natural tocopherols in an amount of from 05-10% of the weight of said mercapto compound.
15. A stable ointment for arsenic and cadmium therapy containing, anhydrous lanolin, 2, 3-dimercaptopropanol, and an anti-oxidant for said mercapto compound comprising mixed natural tocopherols in an amount of from 05-10% of the weight of said mercapto compound.
16. A stable ointment for arsenic and cadmium therapy comprising in parts by weight:
Peanut 011 36.95 Lanolin, anhydrous 8.00 Cetyl alcohol 10.00 Glyceryl monostearate 10.00 White petrolatum, soft 25.00 Benzyl benzoate 5.00 Mixed natural tocopherols 0.05 2, 3-dimercaptopropanol 5.00
6 17. A stable ointment for arsenic and cadmium therapy comprising in parts by Weight:
Lanolin, anhydrous 80.0 Benzyl benzoate 10.0 Mixed natural tocopherols, 0.1 2, 3-dimercaptopropanol 10.0
GEORGE W. RIGBY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS

Claims (2)

1. A STABLE OINTMENT COMPRISING AN OILY VEHICLE, 2,3-DIMERCAPTOPROPANOL, AND AN OIL-SOLUBLE ANTIOXIDANT FOR THE MERCAPTO COMPOUND SELECTED FROM THE GROUP CONSISTING OF TOCOPHEROL AND PALMITOYL ASCORBATE, THE ANT-OXIDANT BEING PRESENT IN AN AMOUNT OF AT LEAST 0.5 PER CENT BY WEIGHT OF THE SAID MERCAPTO COMPOUND.
2. AN ANTI-VESICANT COMPOSITION CONTAINING, 2,3-DIMERCAPTOPROPANOL, AND AN ANTI-OXIDANT FOR SAID MERCAPTO COMPOUND COMPRISING TOCOPHEROL IN AN AMOUNT OF AT LEAST 0.5 PER CENT BY WEIGHT OF THE SAID MERCAPTO COMPOUND.
US581323A 1945-03-06 1945-03-06 Ointments containing oil-soluble antioxidants Expired - Lifetime US2582395A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US581323A US2582395A (en) 1945-03-06 1945-03-06 Ointments containing oil-soluble antioxidants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US581323A US2582395A (en) 1945-03-06 1945-03-06 Ointments containing oil-soluble antioxidants

Publications (1)

Publication Number Publication Date
US2582395A true US2582395A (en) 1952-01-15

Family

ID=24324739

Family Applications (1)

Application Number Title Priority Date Filing Date
US581323A Expired - Lifetime US2582395A (en) 1945-03-06 1945-03-06 Ointments containing oil-soluble antioxidants

Country Status (1)

Country Link
US (1) US2582395A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169143A (en) * 1978-07-10 1979-09-25 Irving Haimowitz Method for treating hemorrhoid symptoms and composition for use therein
US4410517A (en) * 1980-05-20 1983-10-18 Theodore Stillman Vitamin E (tocopherol) compositions which resemble petrolatum
US4551332A (en) * 1981-08-05 1985-11-05 Theodore Stillman Vitamin E compositions and methods
US4664914A (en) * 1984-10-17 1987-05-12 Theodore Stillman Jojoba oil compositions and methods
WO1992000077A1 (en) * 1990-06-28 1992-01-09 Medicis Corporation Improved ointment base and method of use
US20070083999A1 (en) * 2005-10-13 2007-04-19 Leskowicz James J Deodorizing compositions
US20070083998A1 (en) * 2005-10-13 2007-04-19 Leskowicz James J Deodorizing compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2267224A (en) * 1940-09-09 1941-12-23 Gen Mills Inc Process of stabilizing shortening
US2317353A (en) * 1940-08-31 1943-04-27 Distillation Products Inc Purification or concentration of tocopherol
US2333655A (en) * 1942-03-31 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
US2333657A (en) * 1942-05-26 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
US2361624A (en) * 1941-09-20 1944-10-31 Frederick M Turnbull Stabilized therapeutic agents
US2363722A (en) * 1941-11-10 1944-11-28 Sonneborn Sons Inc L Stabilized medicinal white oils

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2317353A (en) * 1940-08-31 1943-04-27 Distillation Products Inc Purification or concentration of tocopherol
US2267224A (en) * 1940-09-09 1941-12-23 Gen Mills Inc Process of stabilizing shortening
US2361624A (en) * 1941-09-20 1944-10-31 Frederick M Turnbull Stabilized therapeutic agents
US2363722A (en) * 1941-11-10 1944-11-28 Sonneborn Sons Inc L Stabilized medicinal white oils
US2333655A (en) * 1942-03-31 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
US2333657A (en) * 1942-05-26 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169143A (en) * 1978-07-10 1979-09-25 Irving Haimowitz Method for treating hemorrhoid symptoms and composition for use therein
US4410517A (en) * 1980-05-20 1983-10-18 Theodore Stillman Vitamin E (tocopherol) compositions which resemble petrolatum
US4551332A (en) * 1981-08-05 1985-11-05 Theodore Stillman Vitamin E compositions and methods
US4664914A (en) * 1984-10-17 1987-05-12 Theodore Stillman Jojoba oil compositions and methods
WO1992000077A1 (en) * 1990-06-28 1992-01-09 Medicis Corporation Improved ointment base and method of use
US20070083999A1 (en) * 2005-10-13 2007-04-19 Leskowicz James J Deodorizing compositions
US20070083998A1 (en) * 2005-10-13 2007-04-19 Leskowicz James J Deodorizing compositions
US7261742B2 (en) 2005-10-13 2007-08-28 S.C. Johnson & Son, Inc. Method of deodorizing a textile
US7407515B2 (en) 2005-10-13 2008-08-05 S.C. Johnson & Son, Inc. Method of deodorizing a textile
US7407922B2 (en) 2005-10-13 2008-08-05 S.C. Johnson & Son, Inc. Deodorizing compositions

Similar Documents

Publication Publication Date Title
EP0229652B1 (en) Stabilized tocopherol in dry, particulate, free-flowing form
US2582395A (en) Ointments containing oil-soluble antioxidants
Skriver et al. Temperature-induced changes in fatty acid unsaturation of Tetrahymena membranes do not require induced fatty acid desaturase synthesis
ES507807A0 (en) PROCEDURE FOR OBTAINING TRICYCLIC DERIVATIVES FROM CYTOSINE.
US2255191A (en) Preserving materials
US2056208A (en) Acetyl-salicylic acid composition
GB1070517A (en) X-ray contrast medium
US2614963A (en) Keratin exfoliative compositions
EP0090378B1 (en) Isoprenylcarboxylic acid-containing composition for external use
GB2135577A (en) Hydrocortisone butyrate propionate ointments
GB444276A (en) An improved process for the manufacture of medicinal preparations containing chlorophyll or chlorophylline
US2758049A (en) Iodine dissolved in an aqueous solution of polyacrylic acid
JPH054925A (en) Soft capsule preparation of alpha calcidiol
US2572828A (en) Alkoxyalkyl esters of monoiodomono-alkoxybenzoic acids
US2567584A (en) Colloidal iodine preparation and method of making the same
Kern et al. Vitamin A Alcohol Stability and Absorption: Influence of Antioxidants
US2758931A (en) Antioxidant composition
US3035078A (en) Stabilized polyisocyanate compositions
ES480091A1 (en) (Omega-aminoalkoxy) bibenzyls, processes for their preparation and pharmaceutical compositions containing these substances.
RU2107491C1 (en) Preparation for protecting hand skin
US2609323A (en) Alkyl vanillate ointment
Buchthal et al. Application of adenosine triphosphate and related compounds to mammalian striated and smooth muscle
SU812290A1 (en) Method of stabilizing ethers of unsaturated fatty acids
US2281937A (en) Therapeutic composition
US2494717A (en) Peanut products and process for preparing the same