US3766052A - Process for the purification of coal tar - Google Patents
Process for the purification of coal tar Download PDFInfo
- Publication number
- US3766052A US3766052A US00236954A US3766052DA US3766052A US 3766052 A US3766052 A US 3766052A US 00236954 A US00236954 A US 00236954A US 3766052D A US3766052D A US 3766052DA US 3766052 A US3766052 A US 3766052A
- Authority
- US
- United States
- Prior art keywords
- coal tar
- acid ester
- fatty acid
- squalane
- hydrocarbon
- 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
- 239000011280 coal tar Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000000746 purification Methods 0.000 title abstract description 5
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- -1 fatty acid ester Chemical class 0.000 claims abstract description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 17
- 239000000194 fatty acid Substances 0.000 claims abstract description 17
- 229930195729 fatty acid Natural products 0.000 claims abstract description 17
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940032094 squalane Drugs 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical group O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 6
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 claims description 3
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000284 extract Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000002674 ointment Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000000622 irritating effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940031439 squalene Drugs 0.000 description 2
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940052228 zinc oxide paste Drugs 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940057004 coal tar extract Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/18—Working-up tar by extraction with selective solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
Definitions
- ABSTRACT A process for the purification of coal tar. This process comprises treating commercially available coal tar with a fatty acid ester, extracting the fatty acid ester treated coal tar with a higher molecular weight hydrocarbon such as squalane and recovering the hydrocarbon-extracted product.
- the coal tar thus treated is dermatologically more acceptable and clinically more effective than known coal tar extracts or preparations and can be incorporated into many dermatologically acceptable vehicles.
- the present invention is concerned with a novel process and, more particularly, the present invention is concerned with a novel process for the purification of coal tar to obtain a product which has all the desirable therapeutic features of coal tar but without the staining and irritating properties.
- the present invention also embraces within its scope the purified coal tar as well as compositions containing the same.
- coal tar is obtained as a by-product during the destructive distillation of bituminous coal. It occurs as a black viscous liquid having a characteristic naphthalene-like odor.
- dermatologically acceptable vehicles such as ointments, lotions or solutions, it is useful in the treatment of a variety of chronic skin diseases. Because of its characteristic irritation index and because of the fact that coal tar does form a dark stain, these properties do render coal tar less desirable for application to the skin.
- a primary object of the invention is to provide a process for extracting the dermatologically active fractions of coal tar to yield a product without the staining and irritating properties of untreated coal tar.
- Another object of this invention is to provide a pro cess for preparing a coal tar extract which is therapeutically potent and can be incorporated into dermatologically acceptable dosage forms.
- Yet another object of this invention is to provide dosage forms incorporating the purified coal tar of this invention.
- a further object of this invention is to provide a process whereby crude coal tar can be readily purified.
- crude coal tar is treated with a fatty acid ester followed by treating the fatty acid ester treated coal tar through an extraction process employing high molecular weight hydrocarbon such as squalane.
- a fatty acid ester is added to crude coal tar.
- squalane is added which causes the precipitation of a pitch-like substance.
- the supernatant liquid is recovered by separation procedures such as decantation and the pitch-like substance is discarded.
- fatty acid esters which can be advantageously employed in the practice of this invention are those having a total of 15 to 22 carbon atoms, for example, isopropyl myristate, isopropyl palmitate, butyl stearate and the like. While squalane is the preferred hydrocarbon, other branched chain hydrocarbons such as squalene may also be advantageously employed.
- the temperature to effect the process of this invention is not critical and can be carried out at an ambient temperature, e.g., between 2030C.
- the new coal tar derivative of this invention can be incorporated in many dosage forms where the new coal tar derivative of this invention can be incorporated are, for example, shampoo, ointment, lotion, solutions and the like.
- These dermatologically known vehicles are well known to the pharmacists art. Generally speaking, from 1 to 10 percent by weight is incorporated into such vehicles.
- the coal tar derivative of this invention can be prepared as an ointment by mixing 10 grams with 990 grams of Zinc Oxide Paste, U.S.P. The patient applies such an ointment liberally to the affected site two or three times daily.
- EXAMPLE 1 Into a vessel there is charged 100 grams of Coal Tar, U.S.P. While agitating, 25 grams of isopropyl myristate is added gradually until a homogenous mixture is obtained. To this is added 25 grams of squalane, with agitation, until precipitation is complete. The mixture is allowed to stand and the supernatant liquid is recovered by careful decantation. The recovered supernatant liquid has a viscosity of 10 to 50 cps as determined by the Brookfield Viscometer No. l spindle at 60 rpm and a spec. grav. at 25C of 0.88 to 0.95.
- EXAMPLE 2 A new coal tar ointment is prepared as follows: 10 grams of the coal tar as prepared from Example 1 is mixed with 5 grams of polysorbate and the resulting mixture is blended with 985 grams of Zinc Oxide Paste, U.S.l.
- a process for the purification of coal tar which comprises:
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Abstract
A process is disclosed for the purification of coal tar. This process comprises treating commercially available coal tar with a fatty acid ester, extracting the fatty acid ester treated coal tar with a higher molecular weight hydrocarbon such as squalane and recovering the hydrocarbon-extracted product. The coal tar thus treated is dermatologically more acceptable and clinically more effective than known coal tar extracts or preparations and can be incorporated into many dermatologically acceptable vehicles.
Description
at I].
[ POCESS FOR THE PIURHJFII' CATION 0F 00AM. TAR
[75] Inventors: Michnei lnseph Bordovsky; William Henry Woiler, both of San Antonio, Tex.
[73] Assignee: Warner-Lambert Company, Morris Plains, NJ.
[22] Filed: Mar. 22, 11972 [21] Appl. No.: 236,954
[52] US. "Cl. 208/45 [51] ilnt. Cl. (1110c 3/00 [58] Field of Search 208/39, 43, 44, 45
n11 @ct. M, 11073 Chem. Abstr. Vol. 67: 120,130x 1967 [5 7] ABSTRACT A process is disclosed for the purification of coal tar. This process comprises treating commercially available coal tar with a fatty acid ester, extracting the fatty acid ester treated coal tar with a higher molecular weight hydrocarbon such as squalane and recovering the hydrocarbon-extracted product. The coal tar thus treated is dermatologically more acceptable and clinically more effective than known coal tar extracts or preparations and can be incorporated into many dermatologically acceptable vehicles.
6 Claims, No Drawings PROCESS FOR THE lPlUlltlllFllCATllON OlF COAL TAR The present invention is concerned with a novel process and, more particularly, the present invention is concerned with a novel process for the purification of coal tar to obtain a product which has all the desirable therapeutic features of coal tar but without the staining and irritating properties.
The present invention also embraces within its scope the purified coal tar as well as compositions containing the same.
The therapeutic use of coal tar is well recognized; for example, the US. Pharmacopeia contains a monograph for this product. Commercially, coal tar is obtained as a by-product during the destructive distillation of bituminous coal. It occurs as a black viscous liquid having a characteristic naphthalene-like odor. When coal tar is incorporated into dermatologically acceptable vehicles such as ointments, lotions or solutions, it is useful in the treatment of a variety of chronic skin diseases. Because of its characteristic irritation index and because of the fact that coal tar does form a dark stain, these properties do render coal tar less desirable for application to the skin.
Accordingly, a primary object of the invention is to provide a process for extracting the dermatologically active fractions of coal tar to yield a product without the staining and irritating properties of untreated coal tar.
Another object of this invention is to provide a pro cess for preparing a coal tar extract which is therapeutically potent and can be incorporated into dermatologically acceptable dosage forms.
Yet another object of this invention is to provide dosage forms incorporating the purified coal tar of this invention.
A further object of this invention is to provide a process whereby crude coal tar can be readily purified.
Other objects and advantages of this invention will become more apparent from the following detailed description.
According to the present invention, crude coal tar is treated with a fatty acid ester followed by treating the fatty acid ester treated coal tar through an extraction process employing high molecular weight hydrocarbon such as squalane. Thus, for example, in a typical practice of this invention, a fatty acid ester is added to crude coal tar. Then squalane is added which causes the precipitation of a pitch-like substance. The supernatant liquid is recovered by separation procedures such as decantation and the pitch-like substance is discarded.
Generally speaking, for each 100 parts by weight of crude coal tar, about 25 to 50 parts by weight of the fatty acid ester is added. Also, for each 100 parts of crude coal tar, about 25 to 50 parts by weight of squalane is employed However, in order to obtain the most desirable results, it is most advantageous to maintain a one to one ratio of squalane to the fatty acid ester. For example, if 25 parts of the fatty acid ester are utilized in the initial step, 25 parts of squalane are employed in the second step. Further, to obtain optimum separation, it is critical to adhere to a definite order of treatment; that is, the coal tar is first treated with the fatty acid ester and then treated with the squalane. The resulting product thus obtained exhibits all the desirable therapeutic properties of coal tar but is less irritating and staining upon contact with the skin.
Among the fatty acid esters which can be advantageously employed in the practice of this invention are those having a total of 15 to 22 carbon atoms, for example, isopropyl myristate, isopropyl palmitate, butyl stearate and the like. While squalane is the preferred hydrocarbon, other branched chain hydrocarbons such as squalene may also be advantageously employed.
The temperature to effect the process of this invention is not critical and can be carried out at an ambient temperature, e.g., between 2030C.
Consequently, an added advantage of this process resides in that no distillation or other high temperature or pressure equipment is needed to effect the extraction.
Among the many dosage forms where the new coal tar derivative of this invention can be incorporated are, for example, shampoo, ointment, lotion, solutions and the like. These dermatologically known vehicles are well known to the pharmacists art. Generally speaking, from 1 to 10 percent by weight is incorporated into such vehicles. For example, the coal tar derivative of this invention can be prepared as an ointment by mixing 10 grams with 990 grams of Zinc Oxide Paste, U.S.P. The patient applies such an ointment liberally to the affected site two or three times daily.
In order to further illustrate the practice of this in vention, the following examples are included.
EXAMPLE 1 Into a vessel there is charged 100 grams of Coal Tar, U.S.P. While agitating, 25 grams of isopropyl myristate is added gradually until a homogenous mixture is obtained. To this is added 25 grams of squalane, with agitation, until precipitation is complete. The mixture is allowed to stand and the supernatant liquid is recovered by careful decantation. The recovered supernatant liquid has a viscosity of 10 to 50 cps as determined by the Brookfield Viscometer No. l spindle at 60 rpm and a spec. grav. at 25C of 0.88 to 0.95.
EXAMPLE 2 A new coal tar ointment is prepared as follows: 10 grams of the coal tar as prepared from Example 1 is mixed with 5 grams of polysorbate and the resulting mixture is blended with 985 grams of Zinc Oxide Paste, U.S.l.
EXAMPLE 3 A shampoo containing the coal tar of this invention is obtained by blending together the following ingredients:
Polyoxyethylene lauryl ether 20% Sodium lauryl sulfate l5-20% Coal Tar of Example 1 10% Water to make l00% EXAMPLE 4 Another ointment is prepared by blending together the following ingredients:
Fatty alcohols l0-l5% Mineral oil 8% Petrolatum 25% Sodium lauryl sulfate l-2% Coal Tar to Example l ll0% Water to make We claim: ll. A process for the purification of coal tar which comprises:
a. mixing the coal tar with afatty acid ester having 15 3. A process according to claim 1 wherein 25-50 22 carbon atoms, parts by weight of the hydrocarbon is employed for b. adding to (a) a branched chain higher molecular each 100 parts by weight of the coal tar.
weight hydrocarbon selected from the group con- 4. A process according to claim 1 wherein the hydrosisting of squalane and squalene, and carbon is squalane.
c. recovering the purified coal tar as a supernatant 5. A process according to claim 1 wherein said fatty liquid while keeping the ratio of the fatty acid ester acid ester is isopropyl myristate, isopropyl palmitate or to the hydrocarbon at 1:1. butyl stearate.
2. A process according to claim 1 wherein 25-50 6. A process according to claim 5 wherein said fatty parts by weight of fatty acid ester is added to each 100 acid ester is isopropyl myristate.
parts by weight of the coal tar.
Claims (5)
- 2. A process according to claim 1 wherein 25-50 parts by weigHt of fatty acid ester is added to each 100 parts by weight of the coal tar.
- 3. A process according to claim 1 wherein 25-50 parts by weight of the hydrocarbon is employed for each 100 parts by weight of the coal tar.
- 4. A process according to claim 1 wherein the hydrocarbon is squalane.
- 5. A process according to claim 1 wherein said fatty acid ester is isopropyl myristate, isopropyl palmitate or butyl stearate.
- 6. A process according to claim 5 wherein said fatty acid ester is isopropyl myristate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23695472A | 1972-03-22 | 1972-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3766052A true US3766052A (en) | 1973-10-16 |
Family
ID=22891715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00236954A Expired - Lifetime US3766052A (en) | 1972-03-22 | 1972-03-22 | Process for the purification of coal tar |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3766052A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512275A (en) * | 1994-11-22 | 1996-04-30 | Buck; Carol J. | Topical lotion and method for treatment of androgenic alopecia |
| US5609858A (en) * | 1994-11-22 | 1997-03-11 | Buck; Carol J. | Method for treatment of androgenic alopecia |
| RU2221587C1 (en) * | 2003-02-06 | 2004-01-20 | Фармацевтическое научно-производственное предприятие "Ретиноиды" (Закрытое акционерное общество) | Medicinal agent for dermatosis treatment, method for its preparing (variants) and method for treatment of skin disease |
| US11318161B2 (en) * | 2018-10-09 | 2022-05-03 | Carol J. Buck | Methods of treating basal cell carcinoma and glioblastoma |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060447A (en) * | 1930-05-26 | 1936-11-10 | Ig Farbenindustrie Ag | Working-up of carbonaceous materials |
-
1972
- 1972-03-22 US US00236954A patent/US3766052A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060447A (en) * | 1930-05-26 | 1936-11-10 | Ig Farbenindustrie Ag | Working-up of carbonaceous materials |
Non-Patent Citations (2)
| Title |
|---|
| Chem. Abst. Vol. 64: 17,351d 1966 * |
| Chem. Abstr. Vol. 67: 120,130x 1967 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512275A (en) * | 1994-11-22 | 1996-04-30 | Buck; Carol J. | Topical lotion and method for treatment of androgenic alopecia |
| US5609858A (en) * | 1994-11-22 | 1997-03-11 | Buck; Carol J. | Method for treatment of androgenic alopecia |
| RU2221587C1 (en) * | 2003-02-06 | 2004-01-20 | Фармацевтическое научно-производственное предприятие "Ретиноиды" (Закрытое акционерное общество) | Medicinal agent for dermatosis treatment, method for its preparing (variants) and method for treatment of skin disease |
| US11318161B2 (en) * | 2018-10-09 | 2022-05-03 | Carol J. Buck | Methods of treating basal cell carcinoma and glioblastoma |
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