CH625121A5 - Process for preparing an insecticidal shampoo - Google Patents
Process for preparing an insecticidal shampoo Download PDFInfo
- Publication number
- CH625121A5 CH625121A5 CH1425377A CH1425377A CH625121A5 CH 625121 A5 CH625121 A5 CH 625121A5 CH 1425377 A CH1425377 A CH 1425377A CH 1425377 A CH1425377 A CH 1425377A CH 625121 A5 CH625121 A5 CH 625121A5
- Authority
- CH
- Switzerland
- Prior art keywords
- volume
- shampoo
- added
- acetic acid
- wetting agent
- Prior art date
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- 239000002453 shampoo Substances 0.000 title claims description 26
- 230000000749 insecticidal effect Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 16
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 9
- 239000000080 wetting agent Substances 0.000 claims description 8
- 241000282472 Canis lupus familiaris Species 0.000 claims description 6
- 240000004784 Cymbopogon citratus Species 0.000 claims description 6
- 235000017897 Cymbopogon citratus Nutrition 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000000590 parasiticidal effect Effects 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 235000007303 Thymus vulgaris Nutrition 0.000 claims description 4
- 240000002657 Thymus vulgaris Species 0.000 claims description 4
- 239000000686 essence Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002297 parasiticide Substances 0.000 claims description 4
- 239000001585 thymus vulgaris Substances 0.000 claims description 4
- 241000238876 Acari Species 0.000 claims description 3
- 241000723346 Cinnamomum camphora Species 0.000 claims description 3
- 244000223760 Cinnamomum zeylanicum Species 0.000 claims description 3
- 235000005979 Citrus limon Nutrition 0.000 claims description 3
- 244000131522 Citrus pyriformis Species 0.000 claims description 3
- 244000166675 Cymbopogon nardus Species 0.000 claims description 3
- 235000018791 Cymbopogon nardus Nutrition 0.000 claims description 3
- 240000008853 Datura stramonium Species 0.000 claims description 3
- 241000721662 Juniperus Species 0.000 claims description 3
- 235000013628 Lantana involucrata Nutrition 0.000 claims description 3
- 244000178870 Lavandula angustifolia Species 0.000 claims description 3
- 235000010663 Lavandula angustifolia Nutrition 0.000 claims description 3
- 244000246386 Mentha pulegium Species 0.000 claims description 3
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 3
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 3
- 235000006677 Monarda citriodora ssp. austromontana Nutrition 0.000 claims description 3
- 240000007673 Origanum vulgare Species 0.000 claims description 3
- 244000178231 Rosmarinus officinalis Species 0.000 claims description 3
- 240000004460 Tanacetum coccineum Species 0.000 claims description 3
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 3
- 229960000846 camphor Drugs 0.000 claims description 3
- 229930008380 camphor Natural products 0.000 claims description 3
- 235000017803 cinnamon Nutrition 0.000 claims description 3
- 235000001050 hortel pimenta Nutrition 0.000 claims description 3
- 239000001102 lavandula vera Substances 0.000 claims description 3
- 235000018219 lavender Nutrition 0.000 claims description 3
- 229940015367 pyrethrum Drugs 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 2
- 241000018646 Pinus brutia Species 0.000 claims description 2
- 235000011613 Pinus brutia Nutrition 0.000 claims description 2
- 244000223014 Syzygium aromaticum Species 0.000 claims description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 1
- 240000007313 Tilia cordata Species 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 natural or synthetic Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- 241001674048 Phthiraptera Species 0.000 description 10
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 8
- 229960002809 lindane Drugs 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 244000045947 parasite Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229940085790 synthetic camphor Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 244000089742 Citrus aurantifolia Species 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000517307 Pediculus humanus Species 0.000 description 2
- 241000258242 Siphonaptera Species 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000010634 clove oil Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 238000011418 maintenance treatment Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000001307 Myosotis scorpioides Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000021425 apple cider vinegar Nutrition 0.000 description 1
- 229940088447 apple cider vinegar Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 210000003689 pubic bone Anatomy 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A61Q17/02—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 containing insect repellants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/24—Lauraceae [Laurel family], e.g. laurel, avocado, sassafras, cinnamon or camphor
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/40—Liliopsida [monocotyledons]
- A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Emergency Medicine (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Botany (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Description
La présente invention se rapporte à un procédé de préparation d'un shampooing insecticide comprenant un agent mouillant et à l'utilisation des produits obtenus comme parasiticides et insecticides, particulièrement pour le traitement des chiens contre les tiques et les puces. The present invention relates to a process for the preparation of an insecticidal shampoo comprising a wetting agent and to the use of the products obtained as parasiticides and insecticides, particularly for the treatment of dogs against ticks and fleas.
On connaît différents constituants susceptibles de détruire des insectes comme le DDT, l'hexachlorocyclohexane ou le lindane. Toutefois, ces produits se présentent généralement sous forme de poudre, et leur toxicité élevée rend dangereuse leur utilisation par contact direct avec la peau des mammifères. Various components are known which are capable of destroying insects such as DDT, hexachlorocyclohexane or lindane. However, these products are generally in powder form, and their high toxicity makes them dangerous to use by direct contact with the skin of mammals.
Or, si l'on prend l'exemple des poux et des puces, ces fléaux atteignent de préférence des individus jeunes, donc des individus particulièrement sensibles aux substances toxiques. However, if we take the example of lice and fleas, these plagues preferably affect young individuals, therefore individuals particularly sensitive to toxic substances.
De plus, on sait que certains constituants acides sous forme liquide tels que l'acide acétique sont actifs contre les insectes et les parasites, notamment lorsque ces produits sont utilisés en solution concentrée à pH voisin de 2. In addition, it is known that certain acid constituents in liquid form such as acetic acid are active against insects and parasites, in particular when these products are used in concentrated solution at a pH close to 2.
Toutefois, à ces pH, les produits liquides agresseraient de façon sensible la peau de sorte qu'on est obligé de les utiliser en solution diluée, ce qui diminue notablement leur efficacité. However, at these pHs, the liquid products would appreciably attack the skin so that they are forced to use them in dilute solution, which significantly reduces their effectiveness.
L'objet de la présente invention est le procédé, défini dans la revendication 1, permettant d'obtenir des produits stables, qui pallient ces inconvénients et dont l'action permet, d'une part, de supprimer efficacement les insectes et les parasites et, d'autre part, d'en prévenir le retour sur les parties traitées. The object of the present invention is the process, defined in claim 1, making it possible to obtain stable products which overcome these drawbacks and whose action makes it possible, on the one hand, to effectively suppress insects and parasites and , on the other hand, to prevent the return on the treated parts.
Le procédé selon l'invention peut consister à ajouter de 2 à 12% en volume d'acide acétique, de façon à ajuster le pH de l'ensemble à une valeur inférieure à 3,5, ainsi que 0,5 à 20%, plus particulièrement 0,5 à 3%, en volume de substances insecticides et/ou parasiticides issues de substances naturelles ou obtenues par synthèse, telles que les extraits ou essences de girofle, de lavande, de menthe poivrée, d'origan, de romarin, de tilleul, de genévrier, de citron, de citronelle, de thym, de Datura stramonium, de pin, le pyrèthre, la pyréthrine et des huiles essentielles d'écorce ou de feuilles de canelle de Ceylan. The process according to the invention can consist in adding from 2 to 12% by volume of acetic acid, so as to adjust the pH of the whole to a value lower than 3.5, as well as 0.5 to 20%, more particularly 0.5 to 3%, by volume of insecticidal and / or parasiticidal substances derived from natural substances or obtained by synthesis, such as extracts or essences of cloves, lavender, peppermint, oregano, rosemary, lime, juniper, lemon, lemongrass, thyme, Datura stramonium, pine, pyrethrum, pyrethrin and essential oils of bark or Ceylon cinnamon leaves.
En outre, on peut ajouter avantageusement une substance insectifuge et cicatrisante telle que du camphre naturel ou synthétique, selon des proportions en volume comprises entre 1,5 et 5% et de préférence entre 0,5 et 1,5%. In addition, one can advantageously add an insect repellent and healing substance such as natural or synthetic camphor, in proportions by volume of between 1.5 and 5% and preferably between 0.5 and 1.5%.
Pour mieux faire comprendre les avantages et mettre en valeur le mode d'action des shampooings obtenus par le procédé selon l'invention, on va décrire ci-après des exemples de réalisation du procédé ainsi que l'utilisation des produits obtenus. To better understand the advantages and highlight the mode of action of the shampoos obtained by the process according to the invention, the following will be described examples of carrying out the process as well as the use of the products obtained.
Pour chaque formulation, on constatera que la proportion d'agent mouillant est importante. For each formulation, it will be noted that the proportion of wetting agent is important.
En effet, il a été constaté de façon surprenante que l'effet insecticide de l'acide acétique est considérablement augmenté par l'addition d'agents mouillants tels que les laurylesulfates de sodium, d'ammoniaque ou de triéthanolamine, les bases cationiques classiques ou les produits non ioniques utilisés classiquement dans le domaine des shampooings et que les produits ainsi obtenus étaient remarquablement stables. Indeed, it has surprisingly been found that the insecticidal effect of acetic acid is considerably increased by the addition of wetting agents such as sodium laurylesulfates, ammonia or triethanolamine, conventional cationic bases or the nonionic products conventionally used in the field of shampoos and that the products thus obtained were remarkably stable.
Cette constatation peut être vérifiée à l'aide du test suivant, effectué sur des charançons, des fourmis, des perce-oreilles, des poux et des puces: on dilue, en tiers en volume, le produit réalisé dans les exemples ci-après décrits puis on place quelques gouttes sur chaque insecte pris entre des lamelles, de façon à ce que le corps de l'insecte soit imprégné à peu près au trois-quarts. This observation can be verified using the following test, carried out on weevils, ants, earwigs, lice and fleas: we dilute, in thirds by volume, the product produced in the examples described below then place a few drops on each insect caught between coverslips, so that the body of the insect is impregnated about three-quarters.
On mesure alors le temps nécessaire pour que l'insecte ne soit plus parcouru de mouvements. On compare ce temps à celui obtenu à l'aide d'une solution aqueuse d'acide acétique de pH équivalent. We then measure the time necessary for the insect to no longer be moved. This time is compared to that obtained using an aqueous solution of acetic acid of equivalent pH.
Les résultats constatés montrent que les temps sont en moyenne de deux à cinq fois moindres dans le cas du shampooing que dans le cas de l'acide acétique pur (20 à 50 s au lieu de 1 à 3 mn). The results observed show that the times are on average two to five times shorter in the case of shampoo than in the case of pure acetic acid (20 to 50 seconds instead of 1 to 3 minutes).
Exemple 1: Example 1:
Shampooing efficace contre les poux. Shampoo effective against lice.
Les proportions sont indiquées en volume. The proportions are indicated by volume.
Agent mouillant Texapant "- N 40 (Henkel) dilué à 30% 75 à 95% Texapant "wetting agent - N 40 (Henkel) diluted to 30% 75 to 95%
Camphre synthétique 0,5 à 1,5% Synthetic camphor 0.5 to 1.5%
Citronelle 0,5 à 1,5% Lemongrass 0.5 to 1.5%
Acide acétique 5 à 10% Acetic acid 5 to 10%
Ph 1,8 à 3,5% Ph 1.8 to 3.5%
Le procédé de préparation du shampooing stable est le suivant: The process for preparing the stable shampoo is as follows:
On prépare une solution d'agent mouillant Texapant11 que l'on dilue à 30% dans de l'eau en utilisant une cuve munie d'un agitateur à vitesse lente. A solution of Texapant11 wetting agent is prepared which is diluted to 30% in water using a tank fitted with a slow speed stirrer.
On introduit ensuite le camphre synthétique et la citronelle selon les proportions indiquées ci-dessus jusqu'à complète dissolution. The synthetic camphor and the citronella are then introduced in the proportions indicated above until complete dissolution.
On introduit alors lentement, par l'intermédiaire d'une ampoule à décanter, de l'acide acétique technique en contrôlant le pH, par exemple à l'aide d'un pH-mètre. Technical acetic acid is then introduced slowly, via a separating funnel, by controlling the pH, for example using a pH meter.
On arrête l'addition d'acide acétique lorsque le pH est voisin de 3 et on cesse l'agitation au bout de 5 mn. The addition of acetic acid is stopped when the pH is close to 3 and the stirring is stopped after 5 min.
Traitement des puces, poux et tiques chez les chiens. Treatment of fleas, lice and ticks in dogs.
On a utilisé un shampooing préparé comme décrit dans ce qui précède, contenant 6% d'acide acétique, 1,5% de citronelle et 1,5% d'essence de girofle, et 91 % de Texapant* dilué à 30% (pH ajusté à 2). We used a shampoo prepared as described above, containing 6% acetic acid, 1.5% lemongrass and 1.5% clove oil, and 91% Texapant * diluted to 30% (pH adjusted to 2).
On traite un chien adulte de race teckel infesté de puces. An adult dachshund dog infested with fleas is treated.
Un lavage avec un shampooing de formule vétérinaire ci-dessus est pratiqué un matin à 8 h. A 12 h le chien ne présente plus de puces et n'est plus contaminé pendant 3 j malgré un environnement défavorable. Washing with a shampoo of the above veterinary formula is carried out one morning at 8 a.m. At 12 noon the dog no longer has fleas and is no longer contaminated for 3 days despite an unfavorable environment.
Un traitement d'entretien consistant à pulvériser une lotion constituée d'une solution de décoction de thym à 25%, de vinaigre de cidre à 73% et de citronelle à 2% permet d'éviter tout retour des parasites jusqu'à désinfection complète de l'environnement (locaux et tissus) à l'aide des produits de l'exemple 3. A maintenance treatment consisting of spraying a lotion consisting of a 25% thyme decoction solution, 73% apple cider vinegar and 2% lemongrass prevents any return of the parasites until complete disinfection of the environment (premises and fabrics) using the products of Example 3.
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Exemple 2: Example 2:
Traitement de locaux et tissus. Treatment of premises and fabrics.
On a utilisé un shampooing préparé comme dans l'exemple 1 et composé de 10% d'acide acétique, 2% d'essence de citronelle et 2% de camphre (pH ajusté à 1,8). We used a shampoo prepared as in Example 1 and composed of 10% acetic acid, 2% citronella essence and 2% camphor (pH adjusted to 1.8).
Dans une pièce inoccupée depuis quelque temps et mal fermée, comportant des objets disparates et des tissus, une prolifération de puces a été constatée. In a room that has been vacant for some time and has been poorly closed, containing disparate objects and fabrics, a proliferation of fleas has been observed.
Après rangement des objets, le tapis recouvrant une partie du sol et le carrelage sont aspergés avec le shampooing dilué dans deux fois son volume d'eau. 2 h plus tard les puces ne donnent plus signe de vie. After storage of the objects, the carpet covering part of the floor and the tiles are sprayed with the shampoo diluted in twice its volume of water. 2 hours later, the fleas no longer show any signs of life.
De la même façon, on a traité avec succès des manteaux, couvertures et paniers à chien en les traitant avec des solutions de 5 cm3 de shampooing pour 11 d'eau. Likewise, dog coats, blankets and baskets have been successfully treated by treating them with solutions of 5 cm3 of shampoo per 11 of water.
D'une façon générale, le mode d'action des produits obtenus par le procédé selon l'invention est le suivant: on pratique un shampooing des parties à traiter à l'aide des produits décrits ci-dessus, on laisse les produits agir pendant une durée généralement comprise entre 1 et 10 mn pour les individus et entre 5 et 20 mn pour les objets. In general, the mode of action of the products obtained by the process according to the invention is as follows: shampooing of the parts to be treated is carried out using the products described above, the products are left to act for a duration generally between 1 and 10 minutes for individuals and between 5 and 20 minutes for objects.
On rince abondamment, ce qui entraîne l'acide acétique ou ses équivalents ainsi que les insectes et les parasites. Rinse thoroughly, resulting in acetic acid or its equivalents as well as insects and parasites.
Après le lavage, on constate que les produits répulsifs des insectes restent en quantité suffisante pour protéger contre de nouvelles infections. After washing, it is found that the insect repellants remain in sufficient quantity to protect against new infections.
Toutefois, dans de nombreux cas, on a intérêt à continuer le traitement par des lavages successifs espacés jusqu'à disparition complète des larves ainsi qu'à appliquer un traitement d'entretien comprenant des pulvérisations ou sprays des différentes essences de produits insecticides ou parasiticides cités plus haut, avec ou sans camphre mais de préférence sans acide acétique, c'est-à-dire de citronelle, d'essence de girofle, de lavande, de menthe poivrée, d'origan, de romarin, de tilleul, de genévrier, de citron, de thym, de Datura stramonium, de pyrèthre ou d'huile essentielle de canelle de Ceylan. However, in many cases, it is advantageous to continue the treatment with successive washes spaced until the larvae have completely disappeared, as well as to apply a maintenance treatment comprising sprays or sprays of the different species of insecticide or parasiticide products mentioned. above, with or without camphor but preferably without acetic acid, that is to say, lemon grass, clove oil, lavender, peppermint, oregano, rosemary, lime, juniper, lemon, thyme, Datura stramonium, pyrethrum or Ceylon cinnamon essential oil.
Ces pulvérisations protègent durablement les sujets entre chaque shampooing. These sprays durably protect the subjects between each shampoo.
On a en outre comparé l'action insecticide du shampooing conforme à celui utilisé dans le cas 1 de l'exemple 1 par rapport à une préparation de lindane en poudre à 15% en poids de la façon suivante: We also compared the insecticidal action of the shampoo in accordance with that used in case 1 of Example 1 with respect to a preparation of lindane powder at 15% by weight as follows:
1. Essais sur un pou adulte: 1. Tests on an adult louse:
Dans une coupelle, on met 5 cm3 de shampooing pur, puis on y dépose 5 poux (Pediculus humanus). La mort est immédiate. Afin d'être certain du résultat, un autre essai a été fait en laissant seulement 10 s les poux dans le shampooing et en les retirant avec une baguette en bois. On les met sous une loupe et on constate la mort effective des poux. In a dish, put 5 cm3 of pure shampoo, then place 5 lice (Pediculus humanus) in it. Death is immediate. In order to be certain of the result, another test was made by leaving the lice in the shampoo for only 10 s and removing them with a wooden stick. We put them under a magnifying glass and we note the actual death of lice.
On opère de la même manière avec le shampooing dilué à 50% puis à 25%, afin de se rapprocher des concentrations d'utilisation qui varient de 25 à 100%. The operation is carried out in the same way with the shampoo diluted to 50% then to 25%, in order to approach the use concentrations which vary from 25 to 100%.
La mort des poux est plus lente avec ces deux dilutions, et le test de récupération des poux montre qu'après 30 s les poux ne reviennent pas à la vie. Lice death is slower with these two dilutions, and the lice recovery test shows that after 30 s the lice do not come back to life.
Les mêmes essais sont pratiqués sur l'espèce Phtiriuspubis avec le même pourcentage de mortalité de 100% après 30 s. Ces essais sont repris en comparaison avec une préparation de lindane en poudre à 1,5%. The same tests are carried out on the species Phtiriuspubis with the same percentage of mortality of 100% after 30 s. These tests are repeated in comparison with a 1.5% powdered lindane preparation.
(Tableau en tête de la colonne suivante) (Table at the top of the next column)
Le même essai a été effectué sur des adultes de Phtirius pubis avec des résultats identiques. The same test was carried out on adults of Phtirius pubis with identical results.
Le produit est donc plus actif qu'une formulation de lindane à 1,5%. The product is therefore more active than a 1.5% lindane formulation.
Le tableau ci-après résume les résultats obtenus. Essais sur les Pediculus humanus adultes: The table below summarizes the results obtained. Tests on adult Pediculus humanus:
Pourcentage de mortalité Percentage of mortality
Après 10 s After 10 s
Après 30 s After 30 s
Après 2 h After 2 h
R.S. 206 pur R.S. 206 pure
100% 100%
100% 100%
100% 100%
R.S. 206 dilué à 50% R.S. 206 diluted to 50%
20% 20%
100% 100%
100% 100%
R.S. 206 dilué à 25% R.S. 206 diluted to 25%
0% 0%
100% 100%
100% 100%
Lindane poudre Lindane powder
à 1,5% at 1.5%
0% 0%
0% 0%
50% 50%
Les formulations de lindane à 0,4 et 0,8% ont une action insuffisante pour être utilisées comme élément de comparaison. The 0.4 and 0.8% Lindane formulations have insufficient action to be used as a comparison.
De plus, l'action bactériostatique des produits par le procédé selon l'invention a été vérifiée, et cela bien qu'ils ne contiennent aucun des bactéricides habituellement utilisés tels que paraoxyben-zoate de méthyle, mais divers essais ont montré qu'aucune bactérie ne se développait dans le produit pur ou dilué à 50%. In addition, the bacteriostatic action of the products by the process according to the invention has been verified, and this although they do not contain any of the bactericides usually used such as methyl paraoxyben-zoate, but various tests have shown that no bacteria only developed in the pure product or diluted to 50%.
L'étude faite pour vérifier que la préparation était exempte de bactéries a été poursuivie devant les résultats intéressants obtenus. The study made to verify that the preparation was free of bacteria was continued in front of the interesting results obtained.
La technique utilisée a été la suivante, avec le shampooing préparé selon l'exemple 1 : The technique used was as follows, with the shampoo prepared according to Example 1:
1) ensemencement sur gélose ordinaire, 1) inoculation on ordinary agar,
2) conservation en étuve à 37°C pendant 48 h puis pendant 7 j. 2) storage in an oven at 37 ° C for 48 h and then for 7 days.
Résultats: Results:
Après 48 h Après 7 j After 48 h After 7 days
Shampooing pur 0 colonie 0 colonie Pure shampoo 0 colony 0 colony
Shampooing dilué à 50% 0 colonie 0 colonie Shampoo diluted to 50% 0 colony 0 colony
Après ensemencement avec Escherichia coli: After seeding with Escherichia coli:
Après 48 h Après 7 j After 48 h After 7 days
Shampooing pur 0 colonie 0 colonie Pure shampoo 0 colony 0 colony
Shampooing dilué à 50% 0 colonie 0 colonie Shampoo diluted to 50% 0 colony 0 colony
Enfin, les toxicités relevées peuvent varier de façon importante, ce qui renforce l'intérêt de l'acide acétique associé en synergie avec un agent mouillant, lui conférant un pouvoir insecticide accru tout en maintenant sa toxicité dans des limites tout à fait compatibles avec son utilisation en contact avec des épidermes sensibles. Finally, the toxicities noted can vary significantly, which reinforces the interest of the acetic acid associated in synergy with a wetting agent, giving it an increased insecticidal power while maintaining its toxicity within limits entirely compatible with its use in contact with sensitive skin.
En effet, la toxicité F.O. obtenue par administration du shampooing conforme à l'exemple 1 à des souris river mâles, de poids moyen: 25 g, indique pour dose maximale tolérée 24 ml/kg et pour dose léthale 100, une valeur de 40 ml/kg. Indeed, the F.O. obtained by administration of the shampoo in accordance with Example 1 to male river mice, of average weight: 25 g, indicates for maximum tolerated dose 24 ml / kg and for lethal dose 100, a value of 40 ml / kg.
Les résultats ne permettent pas d'évaluer une dose léthale 50. Par comparaison, on peut rappeler que la dose léthale 50 pour lindane, observée avec des préparations aqueuses administrées par voie orale à des souris, est à peu près de 300 mg/kg. The results do not allow a lethal dose 50 to be evaluated. By comparison, it may be recalled that the lethal dose 50 for lindane, observed with aqueous preparations administered orally to mice, is approximately 300 mg / kg.
Enfin, l'étude de la tolérance locale cutanée a permis de déterminer un indice d'irritation primaire de 0,3, donc faible; les essais d'application répétée sur l'oreille de souris ont permis de conclure que le shampooing n'était pas irritant, et les applications répétées sur le pelage du lapin ont montré une excellente tolérance. Finally, the study of local skin tolerance made it possible to determine a primary irritation index of 0.3, therefore low; the repeated application tests on the mouse ear made it possible to conclude that the shampoo was not irritating, and the repeated applications on the rabbit's coat showed excellent tolerance.
Seuls les essais au niveau oculaire font penser que le shampooing peut être irritant mais que cette action irritative est très faible après une dilution correspondant à l'utilisation du produit. Only eye tests suggest that the shampoo may be irritating but that this irritant action is very weak after dilution corresponding to the use of the product.
D'autres applications et variantes de l'invention seront aisément réalisées par l'homme de l'art sans pour cela sortir du cadre de l'invention, notamment en substituant des équivalents avec différents produits décrits ci-dessus, par exemple en remplaçant l'acide acétique par des acides homologues, mais il a été constaté que les résultats obtenus pouvaient être sensiblement inférieurs, en particulier avec les acides propionique et caprilique. Other applications and variants of the invention will be easily carried out by those skilled in the art without departing from the scope of the invention, in particular by substituting equivalents with the various products described above, for example by replacing the acetic acid by homologous acids, but it was found that the results obtained could be significantly lower, in particular with propionic and caprilic acids.
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Claims (9)
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AT (1) | AT362617B (en) |
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FR2553664A1 (en) * | 1983-10-25 | 1985-04-26 | Charnay Sylvie | Composition based on essential oils from plants, for destroying lice and nits |
IL74067A0 (en) * | 1985-01-16 | 1985-04-30 | Ataron Dev 1985 Ltd | Compositions containing quaternary ammonium compounds |
AU602144B2 (en) * | 1986-05-08 | 1990-10-04 | R & C Products Pty Limited | Animal repellant composition and method |
JPH01149402U (en) * | 1988-04-07 | 1989-10-17 | ||
JPH0211105U (en) * | 1988-07-04 | 1990-01-24 | ||
JPH02115107A (en) * | 1988-10-22 | 1990-04-27 | Matsushita Electric Works Ltd | Antibiotic agent |
US5288483A (en) * | 1990-04-18 | 1994-02-22 | The Procter & Gamble Company | Anti-lice treatment compositions |
EP0525078B1 (en) * | 1990-04-18 | 1997-07-23 | The Procter & Gamble Company | Anti-lice treatment compositions |
AU659625B2 (en) * | 1991-01-18 | 1995-05-25 | Clilco, Ltd. | Lice-repellant compositions |
US5227163A (en) * | 1991-01-18 | 1993-07-13 | Clilco, Ltd. | Lice-repellant compositions |
WO1994016665A2 (en) * | 1993-01-25 | 1994-08-04 | Seleznev, Alexandr Georgievich | Agent to combat lice infestation |
FR2732591B1 (en) * | 1995-04-07 | 1997-06-13 | Benwaiche Joseph | PEST CONTROL SHAMPOO |
DE19631596A1 (en) * | 1996-08-05 | 1998-02-12 | Henkel Kgaa | Washing process |
FR2759546A1 (en) * | 1997-02-19 | 1998-08-21 | Soc Et De Rech De Travaux D Or | Use of citronella components as insecticides |
US20030194454A1 (en) | 1998-07-28 | 2003-10-16 | Bessette Steven M. | Pesticidal compositions containing rosemary oil and wintergreen oil |
GB2347082A (en) * | 1999-02-24 | 2000-08-30 | Margaret Mary Seale | Treatment or prevention of parasitic infection using acetic acid |
GB2355404A (en) * | 1999-08-20 | 2001-04-25 | Polyatomic Apheresis Res Ltd | Vinegar for treating parasites |
WO2001032133A2 (en) * | 1999-11-05 | 2001-05-10 | Nature Plus Inc. | Improved nit removal product |
WO2001060163A2 (en) | 2000-02-17 | 2001-08-23 | Ecosmart Technologies, Inc. | Plant essential oils cointaining pediculicidal compositions |
SE0103401D0 (en) * | 2001-10-12 | 2001-10-12 | Natalie Fresia | Means against lice as well as vermin |
EP1954142B1 (en) * | 2005-11-18 | 2017-04-19 | Wild Child | Pediculicide/ovicide composition |
WO2011154958A1 (en) * | 2010-06-08 | 2011-12-15 | Sequent Scientific Limited | Herbal topical formulation |
NO344832B1 (en) * | 2018-11-02 | 2020-05-18 | Inakva As | Composition for use in the prevention or treatment of attacks or infection of parasites on fish |
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US1589866A (en) * | 1924-11-17 | 1926-06-22 | Siegler Edouard Horace | Insecticide and process of preparing the same |
US2788308A (en) * | 1953-07-07 | 1957-04-09 | Irving L Ochs | Topical non-aqueous acetic compositions |
DE1105549B (en) * | 1957-07-06 | 1961-04-27 | Johannes Roedger Dr Med | Disinfecting detergents and cleaning agents |
NL279632A (en) * | 1962-02-09 | 1964-11-25 | ||
US3650964A (en) * | 1968-05-13 | 1972-03-21 | Basf Wyandotte Corp | Low foam anionic acid sanitizer compositions |
GB1249674A (en) * | 1968-11-28 | 1971-10-13 | Exxon Research Engineering Co | Novel agricultural compositions and leaf-desiccating method |
GB1438946A (en) * | 1972-06-15 | 1976-06-09 | Nat Res Dev | Control of fungi |
GB1438945A (en) * | 1972-06-15 | 1976-06-09 | Nat Res Dev | Control of fungi |
DD111633A1 (en) * | 1974-01-16 | 1975-03-05 | ||
US3969258A (en) * | 1974-10-10 | 1976-07-13 | Pennwalt Corporation | Low foaming acid-anionic surfactant sanitizer compositions |
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NO149718B (en) | 1984-03-05 |
CA1096771A (en) | 1981-03-03 |
JPS54119035A (en) | 1979-09-14 |
ATA834877A (en) | 1980-10-15 |
GB1593601A (en) | 1981-07-22 |
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DK146112C (en) | 1983-11-28 |
DE2752140A1 (en) | 1978-05-24 |
NL188555B (en) | 1992-03-02 |
FR2371190B1 (en) | 1981-06-19 |
BE861000A (en) | 1978-05-22 |
PT67304A (en) | 1977-12-01 |
FR2371190A1 (en) | 1978-06-16 |
AT362617B (en) | 1981-06-10 |
NL188555C (en) | 1992-08-03 |
DE2752140C2 (en) | 1994-02-10 |
LU78565A1 (en) | 1978-04-20 |
AU3083777A (en) | 1979-05-31 |
AU518341B2 (en) | 1981-09-24 |
ES464354A1 (en) | 1978-12-01 |
DK146112B (en) | 1983-07-04 |
NO149718C (en) | 1984-06-13 |
NL7712875A (en) | 1978-05-24 |
ZA776910B (en) | 1978-09-27 |
OA08256A (en) | 1987-10-30 |
SE7713126L (en) | 1978-05-23 |
JPS6113443B2 (en) | 1986-04-14 |
GR70301B (en) | 1982-09-06 |
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