CA1229795A - Method for the prevention of phototoxic reactions - Google Patents
Method for the prevention of phototoxic reactionsInfo
- Publication number
- CA1229795A CA1229795A CA000447775A CA447775A CA1229795A CA 1229795 A CA1229795 A CA 1229795A CA 000447775 A CA000447775 A CA 000447775A CA 447775 A CA447775 A CA 447775A CA 1229795 A CA1229795 A CA 1229795A
- Authority
- CA
- Canada
- Prior art keywords
- oil
- approximately
- odorant substance
- dimethylethyl
- methoxydibenzoylmethane
- 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
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 13
- 231100000760 phototoxic Toxicity 0.000 title claims abstract description 13
- 230000002265 prevention Effects 0.000 title claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 23
- 239000003205 fragrance Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 235000019198 oils Nutrition 0.000 claims description 5
- GVOWHGSUZUUUDR-UHFFFAOYSA-N methyl N-methylanthranilate Chemical compound CNC1=CC=CC=C1C(=O)OC GVOWHGSUZUUUDR-UHFFFAOYSA-N 0.000 claims description 4
- VDBHOHJWUDKDRW-UHFFFAOYSA-N 1-(1,1,2,3,3,6-hexamethyl-2h-inden-5-yl)ethanone Chemical compound CC1=C(C(C)=O)C=C2C(C)(C)C(C)C(C)(C)C2=C1 VDBHOHJWUDKDRW-UHFFFAOYSA-N 0.000 claims description 3
- 244000061520 Angelica archangelica Species 0.000 claims description 2
- 235000007129 Cuminum cyminum Nutrition 0.000 claims description 2
- 244000304337 Cuminum cyminum Species 0.000 claims description 2
- 235000001287 Guettarda speciosa Nutrition 0.000 claims description 2
- 235000019501 Lemon oil Nutrition 0.000 claims description 2
- 235000019502 Orange oil Nutrition 0.000 claims description 2
- 239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 claims description 2
- 239000010501 lemon oil Substances 0.000 claims description 2
- 239000010502 orange oil Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 2
- 239000010651 grapefruit oil Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010040914 Skin reaction Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000035483 skin reaction Effects 0.000 description 2
- 231100000430 skin reaction Toxicity 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 description 1
- 235000019499 Citrus oil Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010500 citrus oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960004469 methoxsalen Drugs 0.000 description 1
- SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- 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
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
Abstract A method for the prevention of phototoxic reactions caused by odorant substances or odorant substance composi-tions is described. The method comprises using 4-(1,1-di-methylethyl)-4'-methoxydibenzoylmethane for this purpose.
Description
~2~3'7~1~
It is known that a series of organoleptically-active substances, especially odorant substances, produce undesired ~i.e. phototoxic) reactions on or in the skin when they are applied to the skin (e.g. as components of cosmetic preparations) and are there-lpon exposed to the influence of light.
These reactions can be accompanied by subjective and objective phenomena of the exposed skin such as itchillg, inflammations, swellings, reddenings, burnings.
The present invention is concerned with a method for the prevention of such phototoxic reactions caused by odorant substances or odorant substance compositions; the method comprises using for this purpose 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, a substance which has been found to have a very good tolerance both dermally and systemically.
The present invention therefore provides a method for the prevention of phototoxic reactions caused by application to skin of an odorant substance or of a composition containing an odorant substance, which method comprises applying to the skin an amount of 4-(1,1-dimethylethyl)-4'-methoxydibenzoyl-methane which is effective to prevent phototoxic reactions.
The invention is also concerned with odorant substances or odorant substance compositions which contain 4-(1,1-dimethylethyl)-4'-methoxydiben-zoylmethane.
The invention is also concerned with the use of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, also referred to hereinafter as l'dibenzoylmethane", for the prevention of phototoxic reactions caused by odorant substances or odorant substance compositions.
; - 2 --~2~7~S
The most important produc:ts which usually produce phototoxic reactions are odorant substance ccmpositions of natural origin, especially a series of citrus oils such as, for example, bergamot oil, lemon oil, lime oil, orange oil and grapefrult oil. However, angelica oil or cumin oil can also be mentioned in this connection.
As synthetic, organoleptically-active substances which usualLy produce phototoxic reactions there can be mentioned, in particular, methyl N-methylanthranilate and 5-acetyl-1,1,2,3,3,6-hexamethylindane ("Phantolide").
The amount of dibenzoylmethane to be added con-veniently lies in the r~nge of about o.l to about 5 weightpercent, preferably about 0.1 to about 2 weight percent, of the product to be protected.
The dibenzoyLmethane can be added to the product 20 as such or dissolved in a solvent or solv~nt mixture (~Og.
in ethanol).
The following Example illustrates the present invention: ' Example Determination of the phototoxic potential of various products; guinea pigs were used as the experimental animals.
The investigations were carried out under standard conditioni. With the exception of the irradiation periods the animals were kept permanently in wire cages at a temperature of 22 + 2C and a relative atmospheric humidity of 45 - 10%. The daylight cycle was 12 hours/day.
Diet: standard feed and fresh water ad llbitum.
Light source: W-Lamp Westinghouse FS 40 "Blac~
Lamp"; energy: 1 x 104 erg/cm2/sec., spectrum: 320-400 nm, irradiation dosage: 20 j/cm2.
The male and female guinea pigs used weighed between 300-~So g.
Prior to the experimental periods it was ensured that all experimental animals were healthy.
The testmaterial(with or withoutadded dibenzoylmethane) wasapplied inthe highestpossible concentrationwhich was ini -tiallynon-irritating to the skin.Alcohol, acetone,water, pe-trolatum or other suitable solvents were used to dilute or susperd the test material.In addition,2%of dimethylsulphoxide were added to the solutions or incorporated into the preparation in order to increase the skin Penetration.
The test preparations were used as such or option-ally diluted.
~97~i Dosage: For the experiments the ~lcoholic, aceto-nic or aqueous solutions were applied to the skin in an amount of 0.025 ml/cm by means of a pipette. In the case of solutions in petrolatum or ir the case or preparations such as creams, salves, lotions etc amounts of 0.01 ml/2 cm2 were applied~
Observation periods: Obser~ation and evaluation of the skin reaction was carried out 4, 24 and 48 hours after the application of the test material.
Experimental proceduxe: A group of 4 guinea pigs was used to determine the tolerance threshold of the individual test materials p~ior to the induction phase.
In order to determine the highest possible concentration, the test material was applied to the flank (0.25 ml/2 cm2) not only undiluted but also diluted or suspended in suitable solvents in concentrations of 30%, 10%, 3~ and 1%
(or when necessary in even lower concentrations) and left uncovered.
Ex~erimental phase (induction phase): Both flanks of at least 10 guinea pigs were shaved a~ least 2 hours prior to the application of the test material. Thereupon, a maximum of 5 circles each of 2 cm2 were marked on each flank. On 4 of these circular sites there was applied 0.025ml of alcoholic, acetonic or a~ueous test solution (highest initially non-irritating concentration) or O.Cl ml of test solution, which was applied using other solvents or preparations such as creams, salves or lotions.
The fifth application site was in each case treated with a 0.1% alcoholic solution of 8-methoxypsoralen and served as the control.
~22979~
30 minutes after the application of the test material the left flank of each experimental animal was exposed to a non-erythema producing W-A irradiation (20 j/cm2). The right fla~k remained non-irradiated aftex the application of the test material and served as the control.
Observation and evaluation: The animals were investigated for erythema and oedema formation 4, 24 and 48 hours after the application of the test material. ~he skin reaction was evaluated either with -, which signified no reaction, or with +, which signified a positive re-action.
- 6 ~ ~L~297~95 L ~LLL ~ _ a~ ~ i i ~r l l C ~ ~ l l~a 1, ~
~ ~ . _.
C n m O
' ~ u7 ~ _+ l l + + + + +
O O ~0 ~ l +
X i _~ _ + _ + ._ O H :~ + + l l l l + l +
O O ~ + + l l + l + ~ +
~: ~ t- + + + + + + _ +
O ___ _ _ _ ~P ~ dP
,~ d~ ~ ~D ~O ~ u~ ~ ~O ~D
~ . D. ~ 8 ~ a) 8 q ~~ ~
_i h C 8 ~, c N ~ O al u~ ai au ~Z .--1 ~:: E~ ~ O ~,1 u~ _~ ~ J~
.a u~ ~ E~ C:~ C ~ ~ L C ~ ~ X
~ O ~ ~ O ~ V ~C ~ 5 ~1
It is known that a series of organoleptically-active substances, especially odorant substances, produce undesired ~i.e. phototoxic) reactions on or in the skin when they are applied to the skin (e.g. as components of cosmetic preparations) and are there-lpon exposed to the influence of light.
These reactions can be accompanied by subjective and objective phenomena of the exposed skin such as itchillg, inflammations, swellings, reddenings, burnings.
The present invention is concerned with a method for the prevention of such phototoxic reactions caused by odorant substances or odorant substance compositions; the method comprises using for this purpose 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, a substance which has been found to have a very good tolerance both dermally and systemically.
The present invention therefore provides a method for the prevention of phototoxic reactions caused by application to skin of an odorant substance or of a composition containing an odorant substance, which method comprises applying to the skin an amount of 4-(1,1-dimethylethyl)-4'-methoxydibenzoyl-methane which is effective to prevent phototoxic reactions.
The invention is also concerned with odorant substances or odorant substance compositions which contain 4-(1,1-dimethylethyl)-4'-methoxydiben-zoylmethane.
The invention is also concerned with the use of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, also referred to hereinafter as l'dibenzoylmethane", for the prevention of phototoxic reactions caused by odorant substances or odorant substance compositions.
; - 2 --~2~7~S
The most important produc:ts which usually produce phototoxic reactions are odorant substance ccmpositions of natural origin, especially a series of citrus oils such as, for example, bergamot oil, lemon oil, lime oil, orange oil and grapefrult oil. However, angelica oil or cumin oil can also be mentioned in this connection.
As synthetic, organoleptically-active substances which usualLy produce phototoxic reactions there can be mentioned, in particular, methyl N-methylanthranilate and 5-acetyl-1,1,2,3,3,6-hexamethylindane ("Phantolide").
The amount of dibenzoylmethane to be added con-veniently lies in the r~nge of about o.l to about 5 weightpercent, preferably about 0.1 to about 2 weight percent, of the product to be protected.
The dibenzoyLmethane can be added to the product 20 as such or dissolved in a solvent or solv~nt mixture (~Og.
in ethanol).
The following Example illustrates the present invention: ' Example Determination of the phototoxic potential of various products; guinea pigs were used as the experimental animals.
The investigations were carried out under standard conditioni. With the exception of the irradiation periods the animals were kept permanently in wire cages at a temperature of 22 + 2C and a relative atmospheric humidity of 45 - 10%. The daylight cycle was 12 hours/day.
Diet: standard feed and fresh water ad llbitum.
Light source: W-Lamp Westinghouse FS 40 "Blac~
Lamp"; energy: 1 x 104 erg/cm2/sec., spectrum: 320-400 nm, irradiation dosage: 20 j/cm2.
The male and female guinea pigs used weighed between 300-~So g.
Prior to the experimental periods it was ensured that all experimental animals were healthy.
The testmaterial(with or withoutadded dibenzoylmethane) wasapplied inthe highestpossible concentrationwhich was ini -tiallynon-irritating to the skin.Alcohol, acetone,water, pe-trolatum or other suitable solvents were used to dilute or susperd the test material.In addition,2%of dimethylsulphoxide were added to the solutions or incorporated into the preparation in order to increase the skin Penetration.
The test preparations were used as such or option-ally diluted.
~97~i Dosage: For the experiments the ~lcoholic, aceto-nic or aqueous solutions were applied to the skin in an amount of 0.025 ml/cm by means of a pipette. In the case of solutions in petrolatum or ir the case or preparations such as creams, salves, lotions etc amounts of 0.01 ml/2 cm2 were applied~
Observation periods: Obser~ation and evaluation of the skin reaction was carried out 4, 24 and 48 hours after the application of the test material.
Experimental proceduxe: A group of 4 guinea pigs was used to determine the tolerance threshold of the individual test materials p~ior to the induction phase.
In order to determine the highest possible concentration, the test material was applied to the flank (0.25 ml/2 cm2) not only undiluted but also diluted or suspended in suitable solvents in concentrations of 30%, 10%, 3~ and 1%
(or when necessary in even lower concentrations) and left uncovered.
Ex~erimental phase (induction phase): Both flanks of at least 10 guinea pigs were shaved a~ least 2 hours prior to the application of the test material. Thereupon, a maximum of 5 circles each of 2 cm2 were marked on each flank. On 4 of these circular sites there was applied 0.025ml of alcoholic, acetonic or a~ueous test solution (highest initially non-irritating concentration) or O.Cl ml of test solution, which was applied using other solvents or preparations such as creams, salves or lotions.
The fifth application site was in each case treated with a 0.1% alcoholic solution of 8-methoxypsoralen and served as the control.
~22979~
30 minutes after the application of the test material the left flank of each experimental animal was exposed to a non-erythema producing W-A irradiation (20 j/cm2). The right fla~k remained non-irradiated aftex the application of the test material and served as the control.
Observation and evaluation: The animals were investigated for erythema and oedema formation 4, 24 and 48 hours after the application of the test material. ~he skin reaction was evaluated either with -, which signified no reaction, or with +, which signified a positive re-action.
- 6 ~ ~L~297~95 L ~LLL ~ _ a~ ~ i i ~r l l C ~ ~ l l~a 1, ~
~ ~ . _.
C n m O
' ~ u7 ~ _+ l l + + + + +
O O ~0 ~ l +
X i _~ _ + _ + ._ O H :~ + + l l l l + l +
O O ~ + + l l + l + ~ +
~: ~ t- + + + + + + _ +
O ___ _ _ _ ~P ~ dP
,~ d~ ~ ~D ~O ~ u~ ~ ~O ~D
~ . D. ~ 8 ~ a) 8 q ~~ ~
_i h C 8 ~, c N ~ O al u~ ai au ~Z .--1 ~:: E~ ~ O ~,1 u~ _~ ~ J~
.a u~ ~ E~ C:~ C ~ ~ L C ~ ~ X
~ O ~ ~ O ~ V ~C ~ 5 ~1
Claims (9)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for the prevention of photo-toxic reactions caused by application to skin of an odorant substance or of a composition containing an odorant substance, which method comprises applying to the skin an amount of 4-(1,1-dimethylethyl)-4'-methoxy-dibenzoylmethane which is effective to prevent phototoxic reactions.
2. A method according to claim 1 wherein the odorant substance is present in an odorant substance composition.
3. A method according to claim 2, wherein the odorant substance is bergamot oil which is treated with 4-(1,1-dimethyl-ethyl)-4'-methoxydibenzoylmethane.
4. A method according to any one of claims 1 to 3, wherein 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane is used in an amount of approximately 0.1 to approximately 5 weight percent of the odorant substance or odorant substance composition.
5. A method according to any one of claims 1 to 3, wherein 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane is used in an amount of approximately 0.1 to approximately 2 weight percent.
6. An odorant substance composition which contains at least one of the ingredients of the group consisting of bergamot oil, lemon oil, lime oil, orange oil, grapefruit oil, angelica oil, cumin oil, methyl N-methylanthranilate and 5-acetyl-1,1,2,3,3,6-hexamethylindane, as ingredients which are prone to cause photo-toxic reactions, and 4-(1,1-dimethylethyl)-4'-methoxydibenzol-methane.
7. A composition according to claim 6, wherein the odorant substance is bergamot oil or the odorant substance composition contains bergamot oil.
8. A composition according to claim 6 or 7 which contains approximately 0.1 to approximately 5 weight percent of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane.
9. A composition according to claim 6 or 7 which contains approximately 0.1 to approximately 2 weight percent of 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH927/83 | 1983-02-18 | ||
| CH927/83A CH653255A5 (en) | 1983-02-18 | 1983-02-18 | Perfumes or perfume compositions containing agents to prevent phototoxic reactions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1229795A true CA1229795A (en) | 1987-12-01 |
Family
ID=4198406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000447775A Expired CA1229795A (en) | 1983-02-18 | 1984-02-17 | Method for the prevention of phototoxic reactions |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU560945B2 (en) |
| BR (1) | BR8400693A (en) |
| CA (1) | CA1229795A (en) |
| CH (1) | CH653255A5 (en) |
| ES (1) | ES8604713A1 (en) |
| IL (1) | IL70825A (en) |
| IT (1) | IT1209497B (en) |
-
1983
- 1983-02-18 CH CH927/83A patent/CH653255A5/en not_active IP Right Cessation
-
1984
- 1984-01-30 IL IL70825A patent/IL70825A/en not_active IP Right Cessation
- 1984-02-09 IT IT8419537A patent/IT1209497B/en active
- 1984-02-10 AU AU24450/84A patent/AU560945B2/en not_active Expired
- 1984-02-16 BR BR8400693A patent/BR8400693A/en not_active IP Right Cessation
- 1984-02-17 CA CA000447775A patent/CA1229795A/en not_active Expired
- 1984-02-17 ES ES529843A patent/ES8604713A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH653255A5 (en) | 1985-12-31 |
| ES529843A0 (en) | 1986-02-16 |
| IL70825A (en) | 1989-03-31 |
| ES8604713A1 (en) | 1986-02-16 |
| AU2445084A (en) | 1984-08-23 |
| AU560945B2 (en) | 1987-04-30 |
| IT1209497B (en) | 1989-08-30 |
| BR8400693A (en) | 1984-09-25 |
| IT8419537A0 (en) | 1984-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |