US3562806A - Rumen stable medicament and/or nutrient compositions - Google Patents

Rumen stable medicament and/or nutrient compositions Download PDF

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Publication number
US3562806A
US3562806A US758874A US3562806DA US3562806A US 3562806 A US3562806 A US 3562806A US 758874 A US758874 A US 758874A US 3562806D A US3562806D A US 3562806DA US 3562806 A US3562806 A US 3562806A
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rumen
cellulose
materials
medicament
composition
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US758874A
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English (en)
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Peter M Grant
John W Mench
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Eastman Kodak Co
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Eastman Kodak Co
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
    • A23K40/35—Making capsules specially adapted for ruminants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • the present invention relates to special compositions that are specially useful for preserving sensitive materials from undesired reaction when they are subjected to degradative environments. More specifically this invention relates to compositions containing a significant amount of a cellulosic material such as cellulose propionate 3-morpholinobutyrate effective in inhibiting such undesired reaction.
  • a cellulosic material such as cellulose propionate 3-morpholinobutyrate
  • ruminants such as sheep and cattle
  • medicaments having enteric coating are, unfortunately, not protected from the drastic treatments afforded in the rumens of such animals.
  • Medicaments given orally to ruminants pass directly irst into the rumen (which has a large population of microorganisms and is either neutral or slightly acidic). From the rumen the materials then pass into the more acidic abomasum, and subsequently into the animals intestine.
  • many medicaments including many desirable nutrients such as vita-mins, amino acids, and the like, are decomposed or metabolized to at least some extent in an undesirable manner in the environment of the rumen.
  • materials intended to be administered orally to ruminants can be eiiectively protected from the rumen environment if the materials are first coated with a cellulosic material having the 3,562,806 Patented Feb. 9, 1971 proper characteristics.
  • Materials having the proper characteristics are those that resist not only the extremely corrosive microorganism environment of the rumen, but also the solubilizing action of the in vivo rumen fluid (which has a pH of from about 5.5 to about 6.5 or more).
  • the cellulosic materials that have been found particularly useful in this respect are those that are the products of the reaction of organic nitrogen-containing bases (wherein there is at least one replaceable hydrogen connected directly to a nitrogen atom; thus, HN with unsaturated cellulose derivatives such as the unsaturated cellulose ethers, unsaturated cellulose ester and unsaturated mixed ethers and esters of cellulose.
  • the unsaturated esters may be aliphatic (substituted or unsubstituted) or unsaturated mononuclear aryl and aralkyl esters of cellulose such as cellulose crotonate, cellulose oleate, cellulose cinnamate, cellulose tiglate, cellulose linoleate, or cellulose ricinoleate.
  • the useful, unsaturated cellulose ethers can be the simple unsaturated aliphatic ethers such as allyl cellulose, vinyl cellulose, or crotonyl cellulose or of the cyclic series, as for example styryl cellulose. Not all the substituent groups on the cellulose molecule need be unsaturated.
  • the useful cellulose molecules can contain saturated ester and ether groups, as for example acetyl, formyl, propionyl, butyryl, isobutyryl, benzoyl, methyl, ethyl, propyl, benzyl; hydroxyalkyl groups such as hydroxymethyl, hydroxyethyl, or hydroxypropyl; and mixtures of any of these.
  • saturated ester and ether groups as for example acetyl, formyl, propionyl, butyryl, isobutyryl, benzoyl, methyl, ethyl, propyl, benzyl; hydroxyalkyl groups such as hydroxymethyl, hydroxyethyl, or hydroxypropyl; and mixtures of any of these.
  • Two or more unsaturated ester or ether groups and/ or two or more saturated ester or ether groups may be present in the cellulose molecules that are reacted with the organic bases as described above.
  • unsaturated mixed ether-esters can
  • the organic bases with which the unsaturated cellulose derivatives are reacted in accordance with these procedures can be aliphatic, alkyl, aromatic, or alicyclic, and preferably should contain from 1 to about 20 carbon atoms. They can be either primary or secondary amines, with secondary amines being preferred. Still further preferred are the cyclic secondary amines such as, for example, piperidine, morpholine and the like.
  • Typical, nonlimiting examples of useful organic bases are methylamine, ethylamine, propylamine, amylamine, hexylamine, dimethylamine, diethylamine, ethanolamine, diethanolamine, 2,2-dichloroethylamine, cyclohexylamine, benzylamine, methyl benzylamine, piperidine, morpholine, and the like.
  • Some of the most valuable medicament or nutrient compositions of the present invention are those in which the medicament or nutrient is coated with cellulose propionate 3-morpholinobutyrate having certain ratios of its .various substituents on the cellulose backbone
  • the cellulose propionate 3-morpholinobutyrate having the properties essential for the success of the present invention are those containing ratios of propionyl, hydroxyl and morpholinobutyryl groups such that they fall within the shaded area designated A in the drawing.
  • Particularly preferred cellulose propionate 3-morpholinobutyrates in this group are those containing from about 13 to about 30% of propionyl from about 0 to about 4 weight percent of hydroxyl, and from about 22 to about 50 weight percent of morpholinobutyryl.
  • the protected medicament and nutrient compositions of this invention can be used successfully when the composition consists mainly of the material to be protected, covered with a very thin continuous coating of at least one of the effective nitrogen-containing cellulosic materials (wherein the weight of the coating can represent as little as about 0.5 weight percent or less, but is preferably at least about 1 weight percent, of the total weight of the composition). It is generally preferred, in the successful practice of this invention, that the medicament and/or nutrient compositions of this invention be blends of (a) one or more medicaments and/or nutrients with (b) one or more of the effective cellulosic materials. Generally, in such blends, the effective cellulosic material(s) will represent at least about Weight percent of the total medicament compositions.
  • the medicament or nutrient portion of the rumenstable compositions of this invention should be solid at temperatures below about 40 C.
  • medicaments that can be utilized in the practice of this invention include antibiotics (such as chlortetracycline, chloramphenicol, bacitracin zinc, erythromycin, oxytetracycline and the like) antibacterials, antivirals, growth stimulants, sulfonamides, anthelmintics, coccidiostats, hormones, vaccines, estrogens, androgens, steroids, tranquilizers and analgesics as well as materials that are often considered as nutrients such as carbohydrates, proteins, amino acids, vitamins and materials.
  • antibiotics such as chlortetracycline, chloramphenicol, bacitracin zinc, erythromycin, oxytetracycline and the like
  • antibacterials antivirals
  • growth stimulants such as chlortetracycline, chloramphenicol, bacitracin zinc, erythromycin, oxytetracycline
  • coated medicaments in the practice of the present invention, one needs simply to dissolve the special cellulosic coating material in an organic solvent such as acetone, methylene chloride, ethylacetate, alcohol, alcohol mixtures, and the like, and subsequently spray the resulting solution over particles of the medicament that is to be protected.
  • the particles generally result from simply compressing the material to be protected into a so-called unit dosage form such as a tablet or a smaller particle, several of which can be used simultaneously as a unit dose, if desired.
  • the solvent can readily be evaporated from the surface of the particles, thereby leaving behind the desired continuous protective coating.
  • Such particles generally have a desirable, hard shiny appearance.
  • Other conventional methods for coating particulated medicaments and nutrients such as, for example, pore coating or fluidized bed procedures can also be used.
  • the resulting coated medicament and/ or nutrient material is surprisingly rumen-stable.
  • compositions of this invention are rumen-stable is that the rumen environment is designed specially to degrade cellulosic materials, while the protecting materials of this invention are cellulosic in nature. Thus, one would ordinarily expect the useful cellulosic materials of this invention to be unstable in the remen environment.
  • a surprisingly high degre of protection can also be afforded medicament materials in the rumen environment if the medicaments are physically blended, initially, with one or more of the nitrogen-containing cellulosic materials of this invention.
  • the medicament can simply be admixed in a conventional stainless steel dough-mixer, for example, preferably with a small amount of solvent for the cellulosic material.
  • the resulting blend can simply be removed from the mixer, cooled if necessary to thoroughly solidify the blend, and ground or crushed to yield particles of the desired size.
  • the rumen-stable medicament and/ or nutrient compositions of the present invention are generally admixed with the ordinary feed that the ruminants are to consume. Therefore, improved feed compositions comprising a blend of common animal food material with a solid, particulated rumen-stable nitrogencontaining cellulosic material that can be solubilized in the presence of a strong acid (which materials have been described in detail hereinbefore), wherein the rumenstable cellulosic material is preferably one of the cellulose propionate 3-morpholinobutyrates having substituents such that it falls within the shaded area in the drawing stabilized with an antioxidant), constitutes one of the preferred embodiments of the present invention.
  • the nitrogen-containing cellulosic materials that are useful in the practice of the present invention degrade spontaneously when they are exposed to air and warmed to slightly elevated temperatures (above about F.) or when they are stored under ambient conditions for an extended period of time. SuchV degradation results in the ultimate insolubilization of the material in the desired medium. It has been found, however, that although the protected compositions of the present invention have utility as rumen-stable compositions over very long periods of time when the nitrogencontaining cellulosic material, per se, is used, the shelf life of the compositions of this invention can be significantly prolonged if there is also present in such compositions an effective amount of an organic antioxidant material.
  • Typical examples of organic antioxidants that can be used successfully to accomplish the desired stabilization of cellulose propionate 3-morpholinobutyrate include butylated hydroxytoluene, pmethoxyphenol, p-tertiary-butylphenol, t-butyl hydroquinone, hydroquinone, thymol, 2,5-bis(1,1-dimethylpropyl) hydroquinone and mixtures thereof. Of these, particularly preferred materials are butylated hydroxytoluene and pmethoxy phenol.
  • the particular antioxidant (or antioxidant mixture) that is utilized, and even the particular nitrogen-containing cellulosic derivative to be stabilized thereby generally from about 0.05 to about 5 weight percent or more (and preferably from about 0.2 and about 2 weight percent), based on the weight of the nitrogen-containing cellulosic material being stabilized can be used.
  • the cellulosic compositions of this invention need not necessarily be used in the pure state for successful results.
  • other materials in addition to the medicament and/ or nutrient
  • Materials such as dyes, pigments, plasticizers (such as diethyl phthalate, triacetin, triphenyl phosphate, polyethylene glycol and the like) can be present in the protected medicaments and/or nutrients of this invention, in some instances, in amounts up to as much as 5 Weight percent or more, if desired.
  • one or more plasticizers be present in the coating layers in order to give the coating improved flexibility.
  • EXAMPLE 1 Into a conventional stainless steel sigma blade mill are introduced 75,000 parts of (82% active) chlortetracycline (CTC), 25,000 parts of a blend of (1) cellulose propionate 3-morpholinobutyrate containing 2% hydroxyl, 19% propionyl, 43% 3-morpholinobutyryl, and having an average molecular weight of about 45,000, with (2) 125 parts of butylated hydroxyphenol (an antioxidant), and 125,000 parts of methylene chloride. The resulting mixture is blended for 20 minutes. The resulting thick, viscous mass is air dried to remove the methylene chloride, Whereupon it becomes solid. It is then ground to pass through a U.S. standard 16 mesh screen.
  • CTC chlortetracycline
  • the resulting product is then blended with a complete lamb feed at the level of 20 grams of CTC per ton of feed. After 10 weeks, the average weight gain of l0 lambs fed with this feed composition has increased more than 5.5 pounds per lamb (15.8%) as compared with the weight gained by a control group of 10 lambs that had been fed the same type of treated feed, except that the CTC in the feed given to the control group was not blended with any of the nitrogen-containing cellulosic materials in accordance with the present invention.
  • EXAMPLE l1 Two hundred sixty seven milligrams of granules of a blend of cellulose propionate 3-morpholinobutyrate and CTC prepared as in Example l, above (that pass through a U.S. Standard 16-mesh screen, but are retained on a U.S. Standard 60-rnesh screen) containing 75% CTC and 25% cellulose propionate 3-morpholinobutyrate are administered abomasally to a live sheep via abomasal cannula. As a control, 200 mg. of CTC are administered in the same manner (but without the cellulose propionate 3-morpholinobutyrate) to a second live sheep. Urine is continually collected through a urethral catheter. It is then analyzed for CTC. Practically the same amount of CTC is recovered from both sheep, indicating that CTC is readily and effectively released in the in vivo abomasal iluid from compositions of the present invention.
  • the medicament compositions described above are stable when they are subjected to the rumen environment and also will dissolve in an aqueous acidic solution having a pH below about 5, the utility of the coated compositions and blends described hereinbefore is not at all limited to application to ruminants.
  • the medicament compositions of this invention demonstrate an effectively prolonged storage life when the compositions are exposed to relatively higher temperatures and humid atmospheres.
  • the coating procedures and blending procedures described above are useful in conjunction with any material that will ultimately be exposed to an aqueous acidic environment (such as is present in the stomach of any animal, including man) and for which is a desire to improve the stability of the material to be protected either when the material is exposed to human conditions or when it is exposed initially to alkaline, neutral, or slightly acidic environments.
  • EXAMPLE 12 Fifteen hundred parts of cellulose propionate 3- morpholinobutyrate (having 1.75 propionyl groups and 1.25 morpholinobutyryl groups per anhydroglucose unit and stabilized with 0.7 weight percent of butylated hydroxytoluene) and 375 parts of diethyl phthalate (plasticizer) are dissolved in 10,0100 parts of a solvent blend of acetonezmethylene chloridezethanol in weight ratios, respectively of 35 960:5. This solution is divided into ten equal portions, each of which is poured gradually over 50,000 parts of deep concave 11/32 inch core tablets of compressed dicalcium orthaphosphate, while the tablets are slowly stirred. After each portion of solution is poured onto the tablets, the solvent is evaporated therefrom by stirring the tablets continuously in a dry, cool air stream.
  • the resulting coated tablets have an excellent, smooth appearance.
  • the tablets do not dissolve or disintegrate in water at room temperature, even after 2 hours such exposure. However, they dissolve readily (in less than 2 minutes) in fresh abomasal uid from a sheep and in U.S.P. simulated gastric fluid.
  • EXAMPLE 13 Two hundred parts of cellulose propionate 3-morpholinobutyrate (having 1.55 propionyl units, 1.05 morpholinobutyryl units and 0.4 hydroxyl units per anhydroglucose unit and stabilized with 0.5 weight percent of ptertiary butylphenol) and 30 parts of diethyl phthalate (plastisizer) are dissolved in 350 parts of methylene chloride. The resulting solution is sprayed gradually onto 6700 parts of dicalcium phosphate deep concave tablets in a conventional tablet coating pan. When finish dried, the resulting tablets are found to have the type of smooth, hard, glossy finish that is considered to be very desirable as a tablet coating uish by the pharmaceutical trade. These tablets do not disintegrate or dissolve in water at room temperature, even though they are stored in contact with water for one week. They can be dissolved in U.S.P. simulated gastric fluid in only one minute, however.
  • EXAMPLE 14 Six parts of the cellulose propionate 3-morpholinobutyrate used in Example 13 is dissolved in 50 parts of methylene chloride. Into this solution is mixed 1 part of powdered chlortetracycline hydrochloride. The resulting slurry is then permitted to dry at room temperature. ⁇ It is then a hard plaque. It is ground into 12/ 30 mesh size granules. These granules release only 2% of their medicament into water in 24 hours, but dissolve completely in U.S.P. simulated gastric fluid in only 2 minutes, completely releasing the medicament into the gastric fluid.
  • a rumen-stable composition which is protected from degradation when said composition is passed through the rumen of a ruminant and which is soluble in abomasal fluid, said composition comprising:
  • An improved feed composition comprising a blend of (a) common animal food material coated with (b) a solid, particulated, rumen-stable composition that is soluble in an aqueous solution having a pH below about 5; said rumen-stable composition comprising:
  • a coated composition comprising:
  • a core material selected from the group consisting of oral ruminant medicaments, nutrients and mixtures thereof, and coated with (b) a coating material; said coating material comprising at least one rumenstable nitrogen-containing cellulosic derivative; said nitrogen-containing cellulosic derivative being a product vfrom the reaction of an unsaturated derivative of cellulose selected from the group consisting of unsaturated cellulose esters, unsaturated cellulose ethers and unsaturated cellulosic mixed ether-esters with an organic base containing at least one H-N group in its molecule.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Husbandry (AREA)
  • Birds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Fodder In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US758874A 1968-09-10 1968-09-10 Rumen stable medicament and/or nutrient compositions Expired - Lifetime US3562806A (en)

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US84295A Expired - Lifetime US3697640A (en) 1968-09-10 1970-10-27 Rumen stable medicament and/or nutrient compositions

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US (2) US3562806A (xx)
AT (1) AT305686B (xx)
BE (1) BE735073A (xx)
CA (1) CA969474A (xx)
CH (1) CH540015A (xx)
CS (1) CS161092B2 (xx)
DE (1) DE1945650A1 (xx)
DK (1) DK125737B (xx)
ES (1) ES370952A1 (xx)
FR (1) FR2081320B1 (xx)
GB (1) GB1283054A (xx)
IT (1) IT1019508B (xx)
NL (1) NL6913734A (xx)
SE (1) SE377043B (xx)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4469684A (en) * 1982-10-15 1984-09-04 The Procter & Gamble Company Storage stable topical pharmaceutical composition containing zinc erythromycin and low dielectric solvents
US4675175A (en) * 1981-10-08 1987-06-23 A.E.C. Societe De Chimie Organique Et Biologique Coated methionine granules for ruminants
US4808412A (en) * 1987-06-11 1989-02-28 Eastman Kodak Company Rumen-stable compositions
US4876097A (en) * 1984-12-20 1989-10-24 Rhone-Poulenc Sante Compositions for coating feeding stuff additives intended for ruminants and feeding stuff additives thus coated
US5152995A (en) * 1986-12-18 1992-10-06 Syntex (U.S.A.) Inc. Stable antibiotic ester feed compositions
US12031128B2 (en) 2021-04-07 2024-07-09 Battelle Memorial Institute Rapid design, build, test, and learn technologies for identifying and using non-viral carriers
US12109223B2 (en) 2020-12-03 2024-10-08 Battelle Memorial Institute Polymer nanoparticle and DNA nanostructure compositions and methods for non-viral delivery

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EG10802A (en) * 1971-02-19 1976-10-31 Bayer Ag A process for embeding veterinary substances and their protection against the influence of the gastric juice of the rumen
US4181709A (en) * 1977-09-02 1980-01-01 Eastman Kodak Company Rumen-stable pellets
FR2401620A1 (fr) * 1977-09-02 1979-03-30 Eastman Kodak Co Granules indegradables dans la panse des ruminants
FR2401619A1 (fr) * 1977-09-02 1979-03-30 Eastman Kodak Co Procede pour preparer des granules indegradables dans la panse des ruminants
US4177255A (en) * 1977-09-02 1979-12-04 Eastman Kodak Company Rumen-stable pellets
US4595584A (en) * 1983-05-26 1986-06-17 Eastman Kodak Company Rumen-stable pellets
AU581691B2 (en) * 1985-10-14 1989-03-02 Balfour Manufacturing Company Limited Process for the production of feedstuffs
US4780315A (en) * 1985-11-25 1988-10-25 Eastman Kodak Company Rumen-stable pellets
CA1331713C (en) * 1988-12-29 1994-08-30 Hitoshi Iijima Granular composition for ruminant
US5089271A (en) * 1989-09-18 1992-02-18 Smithkline Beecham Corporation Stabilized antibiotic compositions for animal feeding
US5149775A (en) * 1991-01-25 1992-09-22 Eastman Kodak Company Method for purifying high molecular weight vinylpyridine/styrene polymers from solution
US5419897A (en) * 1993-04-09 1995-05-30 Buckman Laboratories International, Inc. Ionene polymers as anthelmintics in animals
US6797291B2 (en) 2002-01-09 2004-09-28 Balchem Corporation Stable hygroscopic compositions and methods for stabilizing hygroscopic ingredients
US20050106250A1 (en) * 2002-05-10 2005-05-19 Hasseberg Hans A. Protected active compound formulations of amino acids and process for their preparation
WO2007014122A2 (en) * 2005-07-22 2007-02-01 Clemson University Treated feed supplement capsule for ruminants

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE717719A (xx) * 1967-07-17 1968-12-16

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675175A (en) * 1981-10-08 1987-06-23 A.E.C. Societe De Chimie Organique Et Biologique Coated methionine granules for ruminants
US4469684A (en) * 1982-10-15 1984-09-04 The Procter & Gamble Company Storage stable topical pharmaceutical composition containing zinc erythromycin and low dielectric solvents
US4876097A (en) * 1984-12-20 1989-10-24 Rhone-Poulenc Sante Compositions for coating feeding stuff additives intended for ruminants and feeding stuff additives thus coated
US5152995A (en) * 1986-12-18 1992-10-06 Syntex (U.S.A.) Inc. Stable antibiotic ester feed compositions
US4808412A (en) * 1987-06-11 1989-02-28 Eastman Kodak Company Rumen-stable compositions
US12109223B2 (en) 2020-12-03 2024-10-08 Battelle Memorial Institute Polymer nanoparticle and DNA nanostructure compositions and methods for non-viral delivery
US12031128B2 (en) 2021-04-07 2024-07-09 Battelle Memorial Institute Rapid design, build, test, and learn technologies for identifying and using non-viral carriers

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Publication number Publication date
BE735073A (xx) 1969-12-01
IT1019508B (it) 1977-11-30
CH540015A (fr) 1973-08-15
US3697640A (en) 1972-10-10
FR2081320A1 (xx) 1971-12-03
NL6913734A (xx) 1970-03-12
SE377043B (xx) 1975-06-23
ES370952A1 (es) 1972-01-01
GB1283054A (en) 1972-07-26
CA969474A (en) 1975-06-17
DE1945650A1 (de) 1970-05-14
CS161092B2 (xx) 1975-05-04
DK125737B (da) 1973-04-30
FR2081320B1 (xx) 1974-04-12
AT305686B (de) 1973-03-12

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