DE959052C - Light stabilizers - Google Patents
Light stabilizersInfo
- Publication number
- DE959052C DE959052C DEK25419A DEK0025419A DE959052C DE 959052 C DE959052 C DE 959052C DE K25419 A DEK25419 A DE K25419A DE K0025419 A DEK0025419 A DE K0025419A DE 959052 C DE959052 C DE 959052C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- light stabilizers
- aminobenzoic acid
- solution
- 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
- 239000004611 light stabiliser Substances 0.000 title claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- -1 Amines benzenesulfonic acids Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000003883 ointment base Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
Description
Lichtschutzmittel Es wurden schon zahlreiche Stoffe zur Verwendung als. Lichtschutzmittel vorgeschlagen, unter denen die Aminobenzolcarbonsäuren und Amine benzolsulfönsäuren bzw. deren. Abkömmlinge mehrfach vertreten sind.Light stabilizers Numerous substances have already been used as. Proposed light stabilizers, among which the aminobenzenecarboxylic acids and Amines benzenesulfonic acids or their. Descendants are represented several times.
So ist z. B. das SulfanilsäureEanilid, das eine starke Absorptionswlirkung mit einem Maximum bei 265 mlc besitzt, als Lichtschutzmittel- durchaus brauchbar. Sowohl bei Bestrahlung mit künstlicher Höhensonne als auch bei natürlicher Sonnenbestrahlung bietet es wirksamen Schutz gegen die verbrennenden, Strahlen. Nachteilig ist jedoch seine schwere Wasserlöslichkeit; wässrige Lösungen dieser Verbindung können nur bei hohem pE hergestellt werden Hierdurch ist die Einarbeitung in Cremes und Salben schwienig, da die verwendeten Salbengrundlagen -bei der alkalischen Reaktion leicht zersetzt werden. So is z. B. the sulfanilic acid eanilide, which has a strong absorption effect with a maximum of 265 mlc, quite useful as a light stabilizer. Both with irradiation with artificial sunlamps and with natural solar irradiation it offers effective protection against the burning rays. However, it is disadvantageous its poor solubility in water; aqueous solutions of this compound can only are produced at high pE This means that they can be incorporated into creams and ointments Difficult because the ointment bases used - easy in the alkaline reaction be decomposed.
In der 4-Aminobenzoesäure-N-benzoyl-4'-aminomethansulfonsäure bzw. in deren Salzen mit anorganischen oder organischen Basen wurden nun Verbindungen gefunden, die eine sehr hohe Lichtabsorption und gleichzeitig bedeutende Wasserlöslichkeit bei dem günstigen pE = 8 besitzen. Dabei haben sich sowohl die trockenen Salze als auch deren wäßrige Lösungen als unbedingt lichtbeständig erwiesen. In the 4-aminobenzoic acid-N-benzoyl-4'-aminomethanesulfonic acid or in their salts with inorganic or organic bases there were now compounds found that have a very high light absorption and at the same time significant water solubility have at the favorable pE = 8. Both the dry salts and their aqueous solutions have also been shown to be absolutely lightfast.
Das Absorptionsmaximum der neuen Verbindungen liegt bei 3Iom,u; Die neuen Verbindungn werden in an sich bekannter Weise dadurch gewonnen, daß man auf eine alkalische Lösung der 4'-Aminobenzoyl- 4-aminobenzoesäure Formaldehyd-bisulfit einwirken läßt. Zum Beispiel läßt man. auf eine Lösung aus 5I2 g 4'-Aminobenzoyl-4-aminobenzoesäure und 85 g Natriumhydroxyd in 2,51 Wasser eine zweite Lösung einwirken, die aus 208 g Natriumbisulfit in 300 ccm Wasser und 200g 31% Formaldehyd bereitet wurde. Die Reattionsmischung wird 8 Stunden am Rückfluß gekocht, darauf mit Kohle gereinigt, durch Zusatz von Essigsäure auf PH = 4 eingestellt, worauf das Mononatriumsalz der 4-Aminobenzoesäure-N-benzoyl-4'-aminosulfonsäure in einer Menge von 660 g = 80% der Theorie ausfällt. Zur Gewinnung des Dinatriumsalzes wird das Mononatriumsalz mit der berechneten Menge Natriumhydroxyd umgesetzt. The absorption maximum of the new compounds is 3Iom, u; the new connections are obtained in a manner known per se by clicking on an alkaline solution of the 4'-aminobenzoyl 4-aminobenzoic acid formaldehyde bisulfite can act. For example one lets. to a solution of 5I2 g of 4'-aminobenzoyl-4-aminobenzoic acid and 85 g of sodium hydroxide in 2.5 liters of water act a second solution that consists of 208 g of sodium bisulfite in 300 cc of water and 200 g of 31% formaldehyde was prepared. the Reaction mixture is refluxed for 8 hours, then cleaned with charcoal, adjusted to pH = 4 by adding acetic acid, whereupon the monosodium salt of 4-aminobenzoic acid-N-benzoyl-4'-aminosulfonic acid in an amount of 660 g = 80% the theory fails. The monosodium salt is used to obtain the disodium salt reacted with the calculated amount of sodium hydroxide.
Zur Gewinnung des 4-AminobenzoesäureFN-betlzoyl-4'-aminosulfonsäure- di- (mono- äthanolamin)-Salzes (C19 H27 N4 °8 S) wird eine Lösung aus 32 g Athanolamin, I28 g 4'-Aminobenzoyl-4-aminobenzoesäure und 450 ccm Wasser mit einer zweiten Lösung versetzt, die dadurch erhalten wird, daß man in eine Lösung von 30,5 g Äthanolamin in 100 cm Wasser 32 g Schwefligsäuregas einleitet und die erhaltene Reaktionsmischung mit 50 ccm 3I,6°/oiger Formalinlösung versetzt. Die Mischung der beiden Lösungen wird 4 Stunden am Rüchfluß gekocht darauf mit Kohle gereinigt, klar filtriert und im Vakuum eingedampft. Das hinterbleibende zähe Öl wird in 11 Alkohol auf dem Wasserbad gelöst, und man erhält nah dem Abkühlen II5 g eines Kristallisats, das mit Alkohol und Äther gewaschen wird und bei I850 (unter Zersetzung) schmilzt. Ausbeute: etwa 50°/o der Theorie. To obtain the 4-aminobenzoic acid FN-betlzoyl-4'-aminosulfonic acid di- (mono- ethanolamine) salt (C19 H27 N4 ° 8 S) is a solution of 32 g of ethanolamine, I28 g of 4'-aminobenzoyl-4-aminobenzoic acid and 450 cc of water with a second solution added, which is obtained by adding to a solution of 30.5 g of ethanolamine 32 g of sulfuric acid gas are introduced into 100 cm of water and the reaction mixture obtained mixed with 50 ccm of 3I, 6% formalin solution. The mixture of the two solutions is boiled under reflux for 4 hours, then cleaned with charcoal, filtered clear and evaporated in vacuo. The remaining viscous oil is in 11 alcohol on a water bath dissolved, and close to cooling II5 g of crystals obtained with alcohol and ether is washed and melts at 1850 (with decomposition). Yield: about 50 per cent of theory.
Aus den beschriebenen Salzen der 4-Aminobenzoesäure-N-benzoyl-4'-aminosulfonsäure lassen sich hochprozentige wäßrige Lösungen herstellen, die zur Gewinnung von Wasser-in-Öl- und Öl-in-Wasser-Emulsionen geeignet sind. Eine bevorzugte Anwendungsform der neuen Lichtschutzmittel ist die von leicht auftragbaren Cremes, die mittels der üblichen Salbengrundlagen gewonnen werder. From the described salts of 4-aminobenzoic acid-N-benzoyl-4'-aminosulfonic acid high-percentage aqueous solutions can be produced, which are used to obtain water-in-oil and oil-in-water emulsions are suitable. A preferred form of application of the new Sunscreen is that of easy-to-apply creams made by means of the usual Ointment bases are obtained.
FATENTANSPRACHE: I. Lichtschutzmittel, enthaltend 4-Aminobenzoesäure-N-benzoyl-4'- aminomethansulfonsäure bzw. deren Salze mit anorganischen oder organischen Basen. DEFINITIVE LANGUAGE: I. Sunscreens containing 4-aminobenzoic acid-N-benzoyl-4'- aminomethanesulfonic acid or its salts with inorganic or organic bases.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK25419A DE959052C (en) | 1955-04-03 | 1955-04-03 | Light stabilizers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK25419A DE959052C (en) | 1955-04-03 | 1955-04-03 | Light stabilizers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE959052C true DE959052C (en) | 1957-02-28 |
Family
ID=7217301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK25419A Expired DE959052C (en) | 1955-04-03 | 1955-04-03 | Light stabilizers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE959052C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0095097A1 (en) * | 1982-05-25 | 1983-11-30 | Haarmann & Reimer Gmbh | Para-sulpho-phenyl amides of cinnamic acid, or salts thereof, process for their preparation and their use as sun-screening agents |
-
1955
- 1955-04-03 DE DEK25419A patent/DE959052C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0095097A1 (en) * | 1982-05-25 | 1983-11-30 | Haarmann & Reimer Gmbh | Para-sulpho-phenyl amides of cinnamic acid, or salts thereof, process for their preparation and their use as sun-screening agents |
| US4455295A (en) * | 1982-05-25 | 1984-06-19 | Haarmann & Reimer Gmbh | N-(p-Sulfophenyl) cinnamamide as sunscreen agent |
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