US3538009A - Method for reducing skin irritation in detergent compositions - Google Patents

Method for reducing skin irritation in detergent compositions Download PDF

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Publication number
US3538009A
US3538009A US613095A US3538009DA US3538009A US 3538009 A US3538009 A US 3538009A US 613095 A US613095 A US 613095A US 3538009D A US3538009D A US 3538009DA US 3538009 A US3538009 A US 3538009A
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United States
Prior art keywords
detergent
mildness
additive
detergents
skin
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Expired - Lifetime
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US613095A
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English (en)
Inventor
Ralph Kelly
Edmond Jean Ritter
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.)
Milacron Inc
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Cincinnati Milling Machine Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/03—Hair bleach

Definitions

  • the present invention relates to novel detergent compositions of reduced skin irritation that is normally associated with the use of detergents, to additives employed in combination with skin-irritating detergents, and to detergent formulations containing such additives.
  • the detergent compositions of the present invention comprise a detergent in combination with a mildness additive; said mildness additive or its salt being soluble or, when liquid, colloidally dispersible; the polar groups of the mildness additive being compatible with those of the detergent and stable in aqueous media; the weight ratio of said mildness additive to said detergent varying from 0.005 to 10.
  • soluble and dispersible are meant to define solubility or dispersibility of the mildness additive in concentrations in which the mildness additive is employed in actual use, e.g., 0.5 to 5% by weight.
  • the irritation of the skin by the action of detergents is believed to be caused by the penetration of the detergent into the skin, causing separation and/or degradation of the protein molecules of the keratin layer, thereby exposing the living cells of the skin to the detergent and, more significantly, exposing these cells to other, more irritating compounds associated with the detergent.
  • the damage to the cells caused by this contact is believed to result in irritation, inflammation, and dermatitis.
  • the mildness additives employed in the detergent compositions of the present invention are believed to counteract this breakdown by providing additional bridges between the keratin molecules, thereby preventing the penetration of the detergent molecules through the keratin into the living tissue. It is to be understood, however, that we do not wish to be bound by the foregoing explanation of the activity of the mildness additives of the present invention, and that such explanation is only set forth for a better understanding of the present invention.
  • the preferred mildness additives employed in combination with irritating detergents are the polymerized ethylenically unsaturated C -C fatty acids and polar group-containing derivatives thereof.
  • the polymerized fatty acids contain from 2 to 4 monomeric acid units and, consequently, from 2 to 4 carboxyl groups.
  • the polymerization of ethylenically unsaturated fatty acids into dimer, trimer, and tetramer acids is known in the art and generally results in a cycloaliphatic ring structure.
  • the dimer acid derived from linoleic acid has the structure
  • the dimer, trimer, and tetramer acids are commercially available.
  • the mildness additive need not be pure, but that a mixture of mildness additives can be employed such as the mixture of dimer and trimer acids, and that the mildness additive can, furthermore, contain compounds which do not add to the mildness properties of the additive such as unpolymerized fatty acids.
  • Suitable mildness additives which are based on a fatty acid dimer linking radical include the following in which [D] represents the carboxyl-free residue of a dimerized fatty acid and [T] represents the carboxyl-free residue of a trimer acid:
  • mildness additives described hereinabove can be employed with any detergent, anionic, cationic, nonionic, or amphoteric in nature. It will be apparent, however, that the polar groups of the mildness additive should be compatible with those of the detergent to avoid insolubilization of both detergent and additive. The reduction of skin irritation will be observable in all compatible combinations, although the extent of the anti-irritant effect will differ with the various mildness additives discussed,
  • the described mildness additive is less useful, although the mildness effect of the additive can be established when such detergents, which at normally used concentrations cause little or no skin irritation, are tested at high concentrations and/or longer periods of contact with the skin.
  • the anti-irritation effect of the mildness additive is exhibited over a wide range of proportions of additive to detergent as indicated above. However, optimum results are generally obtained when the ratio of detergent to mildness additive is in the range of 3:1 to 1:3. This preferred range is applicable regardless of whether the detergent is employed in a dilute or concentrated form.
  • Anionic detergents which are improved by combination with the described mildness additive include both the soap and the non-soap detergents.
  • soaps are the sodium, potassium, ammonium, and alkylolammonium salts of higher fatty acids (C to C
  • Nonsoap anionic detergents with which the described mildness additives are suitably employed include alkyl sulfates, alkyl sul onates, alkyl benzene sulfonates, alkyl phenyl polyoxyalkylene sulfonates, alkyl glyceryl ether sulfonates, alkyl monoglyceride sulfates, alkyl monoglyceride sulfonates, alkyl polyoxyethylene ether sulfates, acyl sarcosinates, acyl esters of isethionates, acyl-N-methyl taurides, dialkyl esters of sulfosuccinic acid, and mixture
  • the alkyl or acyl radicals contain from 9 to carbon atoms.
  • these detergents are employed in the form of sodium, potassium, ammonium, and alkylolammonium salts, as well as similar water-soluble salts.
  • Specific examples include sodium lauryl sulfate, potassium-N-methyl lauroyl tauride, triethanol-ammonium dodecyl sulfonate, potassium polypropylene benzene sulfonate, sodium lauryl sulfonate, dioctyl ester of sodium sulfosuccinic acid, sodium salt of lauryl polyoxyethylene sulfate, and sodium salt of tridecylether polyoxyethylene sulfate.
  • the cationic detergents which can be reduced in their skin irritation by the addition of the mildness additives of the present invention include, in particular, quaternary ammonium salts which contain at least one alkyl group having from 12 to 20 carbon atoms.
  • quaternary ammonium salts which contain at least one alkyl group having from 12 to 20 carbon atoms.
  • the halide ions are the preferred anions, other suitable anions include acetate, phosphate, sulfate, nitrite, and the like.
  • Specific cationic detergents include distearyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, stearyl trimethyl ammonium chloride, coco dimethyl benzyl ammonium chloride, dicoco dimethyl ammonium chloride, cetyl pyridinium chloride, cetyl trimethyl ammonium bromide, stearyl amine salts that are soluble in water such as stearyl amine acetate and stearyl amine hydrochloride, stearyl dimethyl amine hydrochloride, distearyl amine hydrochloride, alkyl phenoxyethoxyethyl dimethyl ammonium chloride, decyl pyridinium bromide.
  • Amphoteric, also referred to as ampholitic, detergents which can be improved by the addition of the described mildness additives include alkyl B iminodipropionate, alkyl-fl-arninopropionate, fatty imidazolines, betaines, and mixtures thereof.
  • alkyl B iminodipropionate alkyl-fl-arninopropionate
  • fatty imidazolines fatty imidazolines
  • betaines betaines
  • amphoteric detergents are 1 coco-5-hydroxyethyl-5-carboxymethyl imidazoline, dodecyl-fl-alanine, the inner salt of 2-trimethylamino lauric acid, and N-dodecyl-N,N-dimethyl aminoacetic acid.
  • the mildness additives of the present invention can also be employed in combination with nonionic detergents, although the beneficial effects of the addition of the mildness additive are less pronounced since nonionic detergents are inherently not as irritating as the above-described detergents.
  • Nonionic detergents include, in particular, the alkylene oxide ethers of phenols, fatty alcohols, and alkyl mercaptans, the alkylene oxide esters of fatty acids, the alkylene oxide ethers of fatty acid amides, the condensation products of ethylene oxide with partial fatty acid esters, and mixtures thereof.
  • the polyoxyalkylene chain in such agents can contain from 5 to 30 alkylene oxide units in which each alkylene unit has from 2 to 3 carbon atoms.
  • nonionic detergents include nonyl phenol polyoxyethylene ether, tridecyl alcohol polyoxyethylene ether, dodecyl mercaptan polyoxyethylene thioether, the lauric ester of polyethylene glycol, the lauric ester of methoxy polyethylene glycol, the lauric ester of sorbitan polyoxyethylene ether, and mixtures thereof.
  • the mildness additives of the present invention are particularly effective in reducing the irritation caused by such anionic detergents as the alkyl sulfates and sulfonates and the alkyl benzene sulfates and sulfonates, and by such cationic detergents as the described fatty alkyl-containing quaternary ammonium compounds.
  • detergents described hereinabove are employed in their commercial applications in combination with builders or other additives, depending on the intended commercial utility of the detergent.
  • the presence of such additives does not affect the ability of the mildness additive to counteract the skin irritation caused by the detergent.
  • the skin irritation is caused by the action of the detergent on the skin in causing the keratin of the skin to break down.
  • the detergent itself may not be extremely irritating, it allows other materials employed in combination with the detergent which are highly irritating to come in contact with the living tissue of the skin, even though in the absence of the detergent such materials are nonirritating in not being able to break down the keratin of the skin.
  • the mildness additives of the present invention are, therefore, capable of protecting the skin against skin irritation caused by such additives.
  • Builders employed in commercial detergent formulations are generally alkali salts of weak inorganic acids used alone or in admixtures, such as alkali metal, ammonium or substituted ammonium salts of carbonates, borates, phosphates, polyphosphates, bicarbonates, and silicates. Specific examples of such salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium pyrophosphate, sodium bicarbonate, potassium bicarbonate,.sodium monoand di-orthophosphate, sodium metasilicate, and mixtures thereof.
  • the built detergent compositions of the present invention can, furthermore, contain other adjuvants normally employed in detergent compositions such as perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, fabric softeners, oxygen or chlorine bleaches, suds builders, suds depressors, sequestrants, and the like.
  • adjuvants normally employed in detergent compositions such as perfumes, anti-tarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, fabric softeners, oxygen or chlorine bleaches, suds builders, suds depressors, sequestrants, and the like.
  • the inorganic builders or the combination of the builders an the adjuvants described can constitute up to of the built detergent composition, the remainder of the built detergent composition being the detergent and the mildness additive.
  • the detergent compositions of the present invention include laundry detergents, kitchen detergents, shampoos, industrial detergents, and the like.
  • the use of the mildness additive of the present invention does not affect the effective concentrations of the detergent, and hence concentrations of detergents heretofore employed are also applicable in the modified compositions of the present invention.
  • the use of the mildness additive is, however, not limited to unbuilt or built detergent compositions.
  • the additive can be employed in any compositions in which a detergent of the type described is employed in aqueous solution in the presence of other materials which may cause skin irritation such as, in particular, in aqueous following additional ingredients were added as indicated: lubricants containing inorganic salts, a particular example Igepal CA-630, a commercially available nonionic Wetof which is aqueous cutting fluids.
  • the detercipal test employed in the data presented below is an gent and the mildness additive are each p y in the nimal i m i t t using f l lbi guinea i data illustrated below in a concentration of Weight The anim l, Weighing bo t 300 t 325 i i d percent based on the described 100 g. concentrate.
  • Each 15 accordingly adlhsted t0 takelnto Conslderatlon t e animal is thoroughly rinsed and dried after each immerlower actWe detergent eoheehtratlohsion.
  • the skin of 15 f vvlflg examples Illustrate the effect of the each animal i x mined for gross h d grades mildness additives of the present invention on skin irriare assigned which represent the degree of damage to the tatlon Caused y detergents, 118mg the above-described skin. In general, three animals are tested simultaneously testin the same solution.
  • the grading system is based on a MPLES 1 to 6 Scale to 10 whlch the numbers have the followmg
  • the detergent employed in this series of tests was an meanings. alkyl benzene sulfonate having the formula Grade or rating Gross reaction Skin damage -OH2O 11H23 1 Severe cracking and bleeding, Extremely severe,
  • test solution a g. concentrate is The tests and determination of results illustrated in first prepared which is then employed in the test solution Examples 1-6 were repeated using sodium lauryl sulphate in 1% by volume concentration. In order to prepare a. instead of the alkyl benzene sulfonate. The results are homogeneous concentrate which is readily dilutable, the illustrated in Table II.
  • the concentrate contained 22.5% of the Amphicide and was employed as a 2% test solution containing EXAMPLES 28 AND 29
  • the tests and determination of results illustrated in Examples 1-6 were repeated using Standpol ES-2, a commercially available 26% active detergent containing the sodium salt of lauryl 0 through C diether sulfate.
  • the foregoing examples have illustrated the mildnessinducing etfect of the mildness additives when employed in combination with skin irritating detergents.
  • the skin irritation caused by the detergent is compounded by detergent builders or other components present in the composition.
  • the foregoing examples clearly demonstrate that the mildness agents employed in combination with the detergents are particularly effective in reducing skin irritation where the skin irritation is compounded by the presence of other agents, organic or inorganic.
  • the overall chemical structure of the mildness additives of the present invention is similar to that of a detergent, it will be apparent that the mildness additives of the present invention can be employed in combination with a skin irritating detergent in any environment, i.e., in the presence of any component in which the detergent can exist.
  • the foregoing examples further illustrate that the greatest benefit of the described invention is realized when the mildness additives are combined with detergents or with detergent-containing compositions which cause skin irritation.
  • an aqueous detergent composition involving contact with the skin, said detergent composition containing a skin irritating detergent selected from the group consisting of anionic, cationic, non-ionic, and amphoteric organic detergents, the improvement comprising reducing the skin irritation of said composition by incorporating therein a mildness additive in an amount of .005 to 10 parts by weight based on said skin irritating detergent, said mildness additive comprising the polymerized product of 2 t0 4 molecules of a monomeric C to C fatty acid, said product containing 2 to 4 carboxyl or carboxyl salt groups, said mildness additive being soluble or colloidally dispersible in aqueous media, the mildness additive and detergent compositions being stable and compatible in aqueous media.
  • a skin irritating detergent selected from the group consisting of anionic, cationic, non-ionic, and amphoteric organic detergents
  • anionic detergent is alkyl benzene sulfonate, alkyl sulfate, alkyl benzene sulfates, or alkyl sulfonate.
  • the detergent composition contains from 10 to by weight of the composition of water soluble inorganic detergent builders.
  • amphoteric detergent is an alkyl-B-imino propionate.
  • the detergent composition contains from 10 to 80% by weight of the composition of water soluble inorganic detergent builders.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
US613095A 1967-02-01 1967-02-01 Method for reducing skin irritation in detergent compositions Expired - Lifetime US3538009A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US61309567A 1967-02-01 1967-02-01
US69650968A 1968-01-09 1968-01-09
NL6802006.A NL160162C (nl) 1967-02-01 1968-02-13 Werkwijze voor het op op zichzelf bekende wijze bereiden van een preparaat, dat ten minste een wasactieve stof en ten minste een huidverzachter bevat.
US14057671A 1971-05-05 1971-05-05
US14060471A 1971-05-05 1971-05-05
US05/406,955 US3947382A (en) 1967-02-01 1973-10-16 Mildness additive

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US3538009A true US3538009A (en) 1970-11-03

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Application Number Title Priority Date Filing Date
US613095A Expired - Lifetime US3538009A (en) 1967-02-01 1967-02-01 Method for reducing skin irritation in detergent compositions
US696509A Expired - Lifetime US3630934A (en) 1967-02-01 1968-01-09 Mildness additive
US05/046,560 Expired - Lifetime US4067345A (en) 1967-02-01 1970-06-15 Method and compositions for retarding chemical damage to hair with treating agents containing two or more polar groups
US05/046,561 Expired - Lifetime US4075318A (en) 1967-02-01 1970-06-15 Skin protective compositions
US00140604A Expired - Lifetime US3769242A (en) 1967-02-01 1971-05-05 Mildness additive
US00140576A Expired - Lifetime US3798182A (en) 1967-02-01 1971-05-05 Mildness additive
US05/406,955 Expired - Lifetime US3947382A (en) 1967-02-01 1973-10-16 Mildness additive

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Application Number Title Priority Date Filing Date
US696509A Expired - Lifetime US3630934A (en) 1967-02-01 1968-01-09 Mildness additive
US05/046,560 Expired - Lifetime US4067345A (en) 1967-02-01 1970-06-15 Method and compositions for retarding chemical damage to hair with treating agents containing two or more polar groups
US05/046,561 Expired - Lifetime US4075318A (en) 1967-02-01 1970-06-15 Skin protective compositions
US00140604A Expired - Lifetime US3769242A (en) 1967-02-01 1971-05-05 Mildness additive
US00140576A Expired - Lifetime US3798182A (en) 1967-02-01 1971-05-05 Mildness additive
US05/406,955 Expired - Lifetime US3947382A (en) 1967-02-01 1973-10-16 Mildness additive

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US (7) US3538009A (OSRAM)
AT (1) AT295007B (OSRAM)
BE (1) BE726664A (OSRAM)
CH (1) CH515990A (OSRAM)
DE (1) DE1717099B2 (OSRAM)
FR (1) FR1602753A (OSRAM)
GB (1) GB1221241A (OSRAM)
NL (1) NL160162C (OSRAM)

Cited By (7)

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US3947382A (en) * 1967-02-01 1976-03-30 Cincinnati Milacron, Inc. Mildness additive
US4076799A (en) * 1972-12-27 1978-02-28 Cincinnati Milacron, Inc. Method of inhibiting skin irritation
US4110263A (en) * 1977-06-17 1978-08-29 Johnson & Johnson Baby Products Company Mild cleansing compositions containing alkyleneoxylated bisquaternary ammonium compounds
US4247425A (en) * 1979-05-07 1981-01-27 Sherex Chemical Company, Inc. Light duty non-irritating detergent compositions
US4256611A (en) * 1978-09-13 1981-03-17 Sherex Chemical Company, Inc. Light duty non-irritating detergent compositions
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US20090012166A1 (en) * 2005-07-11 2009-01-08 Hans Uwe Wolf Oligomers of Straight-Chain and Unbranched Fatty Acids and Drugs Containing These

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US3981990A (en) * 1967-02-01 1976-09-21 Cincinnati Milacron, Inc. Skin protective compositions
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DE4314678C1 (de) * 1993-05-04 1994-09-22 Dalli Werke Waesche & Koerperp Stückförmige Körperreinigungsmittel
FR2706304B1 (fr) * 1993-06-15 1995-09-01 Carita Sa Utilisation des huiles de Chaulmoogra dans le domaine cosmétique et pharmaceutique, notamment en dermatologie, pour harmoniser la pigmentation de la peau.
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US5958397A (en) * 1996-07-22 1999-09-28 Schering-Plough Healthcare Products, Inc. Method and composition for protecting against jellyfish stings
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US7036602B2 (en) 2003-07-14 2006-05-02 Weatherford/Lamb, Inc. Retrievable bridge plug
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US20070169285A1 (en) * 2006-01-25 2007-07-26 Saroja Narasimhan Method and kit for coloring hair
US20100193253A1 (en) * 2009-01-30 2010-08-05 Massey Alan J Earth-boring tools and bodies of such tools including nozzle recesses, and methods of forming same
US12233289B2 (en) 2013-08-01 2025-02-25 Olaplex, Inc. Methods for fixing hair and skin
US9095518B2 (en) 2013-08-01 2015-08-04 Liqwd, Inc. Methods for fixing hair and skin
CN106413673A (zh) 2014-05-16 2017-02-15 利奎德股份有限公司 角蛋白处理制剂和方法
US9597273B2 (en) 2015-04-24 2017-03-21 Liqwd, Inc. Methods for treating relaxed hair
CN105267066B (zh) * 2015-10-08 2019-06-11 知识产权全资有限公司 用于处理头发的方法及其试剂盒
EP3175837A1 (en) * 2015-12-01 2017-06-07 Noxell Corporation Method for treating hair
CN105496804A (zh) * 2015-12-25 2016-04-20 知识产权全资有限公司 用于处理头发以及治疗头部牛皮藓的配方及其试剂盒和应用
US20170216175A1 (en) * 2016-02-01 2017-08-03 Active Concepts, LLC Use of bis-amino compounds for treatment of hair
US9872821B1 (en) 2016-07-12 2018-01-23 Liqwd, Inc. Methods and formulations for curling hair
WO2022169633A1 (en) 2021-02-02 2022-08-11 Federici Brands, Llc Composition comprising a hydrolyzed keratin and a silane crosslinking agent and process for hair protection during bleaching

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US3947382A (en) * 1967-02-01 1976-03-30 Cincinnati Milacron, Inc. Mildness additive
US4160819A (en) * 1972-12-27 1979-07-10 Cincinnati Milacron, Inc. Method of inhibiting skin irritation
US4076799A (en) * 1972-12-27 1978-02-28 Cincinnati Milacron, Inc. Method of inhibiting skin irritation
US4137301A (en) * 1972-12-27 1979-01-30 Cincinnati Milacron, Inc. Method of inhibiting skin irritation
US4141966A (en) * 1972-12-27 1979-02-27 Cincinnati Milacron Method of inhibiting skin irritation
US4144319A (en) * 1972-12-27 1979-03-13 Cincinnati Milacron, Inc. Method of inhibiting skin irritation
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US20090012166A1 (en) * 2005-07-11 2009-01-08 Hans Uwe Wolf Oligomers of Straight-Chain and Unbranched Fatty Acids and Drugs Containing These
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Also Published As

Publication number Publication date
NL160162C (nl) 1979-05-15
US4075318A (en) 1978-02-21
US3630934A (en) 1971-12-28
AT295007B (de) 1971-12-27
DE1717099B2 (de) 1973-10-04
US3798182A (en) 1974-03-19
BE726664A (OSRAM) 1969-06-16
DE1717099A1 (de) 1972-04-20
US4067345A (en) 1978-01-10
NL160162B (nl) 1979-05-15
FR1602753A (OSRAM) 1971-01-25
US3947382A (en) 1976-03-30
US3769242A (en) 1973-10-30
NL6802006A (OSRAM) 1969-08-15
CH515990A (de) 1971-11-30
GB1221241A (en) 1971-02-03

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