SE302075B - - Google Patents

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Publication number
SE302075B
SE302075B SE8182/63A SE818263A SE302075B SE 302075 B SE302075 B SE 302075B SE 8182/63 A SE8182/63 A SE 8182/63A SE 818263 A SE818263 A SE 818263A SE 302075 B SE302075 B SE 302075B
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Sweden
Prior art keywords
cis
hept
enal
acid
diyne
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SE8182/63A
Inventor
J Schogt
P Begemann
Jong K De
Koster J Rademaker
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Unilever Nv
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Publication of SE302075B publication Critical patent/SE302075B/xx

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/18—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/206—Dairy flavours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
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    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
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    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
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    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/12—Straight chain carboxylic acids containing eighteen carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Edible Oils And Fats (AREA)
  • Confectionery (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Seasonings (AREA)

Abstract

The following hydrocarbons are prepared: Hexa-1,5-diene, in Example 6, by treating allyl chloride with Mg. metal in ether; Hexa - 1,5 - diyne, in Example 6, by treating 1,2,5,6-tetrabromohexane in ether with sodamide in liquid ammonia; Octa - 1,5 - diyne, in Example 6, by reacting hexa-1,5-diyne with ethyl iodide in ether in the presence of sodamide in liquid ammonia; Hepta - 1,6 - diyne, in Example 8, by reacting sodium acetylide in liquid ammonia with 1,3-dibromopropane; Nona - 1,6 - diyne, in Example 8, by reacting hepta-1,6-diyne with ethyl iodide in ether in the presence of sodamide in liquid ammonia.ALSO:A cream- or butter-like flavouring principle for foods consists of the novel compounds cis-hept-4-enal and/or trans-hept-4-enal or precursor compounds which form the cis- or trans-hept-4-enal as by hydrolysis, oxidation or antoxidation in situ in the foodstuff, for instance during cooking or storage. The following precursors are mentioned: (1) the diethyl acetal of cis- or trans-hept-4-enal; (2) cis- or trans-hept-4-en-1-ol; (3) cis-cis-octadeca-11,15-dienoic acid. cis-cis-octadeca-10,15-dienoic acid and their stereo-isomers, either as the free acids or in the form of their functional derivatives, such as the ethyl esters, triglycerides and partial glycerides, and alkali metal salts; (4) 2-amino-oct-5-enoic acid, which is particularly effective as a precursor during the heating or frying of foods if sugars or dicarbonyl substances are present; (5) the reaction product of hept-4 enal with an edible amino acid containing a primary amino group and a mercapto group attached to adjacent carbon atoms, or a polypeptide or protein derived from it, as exemplified by cysteine or b -lactoglobulin. It is stated that cysteine and b -lactoglobulin react with the hept-4-enal apparently forming compounds with a thiazolidine ring. According to the examples: (1) cis-hept-4-enal is prepared by increasing the chain length of cis-hex-3-en-1-ol by one carbon atom through the bromide and nitrile to cis-hept-4-enoic acid and converting this to cis-hept-4-enal via the acyl chloride and N-methyl anilide; (2) cis-hept-4-enal diethyl acetal is prepared from cis-1romohex-3-ene; (3) cis-hept-4-enal is prepared from cis - hept - 4 - enal diethyl acetal; (4) trans-hept-4-enal diethyl acetal is prepared by converting trans-hex-3-en-1-ol into trans-1-bromohex-3-ene and converting the bromide into the acetal; (5) trans-hept-4-enal diethyl acetal is hydrolysed to trans-hept-4-enal; (6) cis-cis-octadeca-11,15-dienoic acid is prepared by first preparing hexa-1,5-diene from allyl chloride by a coupling reaction using magnesium, converting to hexa-1,5-diyne by bromination and dehydro-bromination, and replacing one of the active hydrogen atoms with an ethyl group to give octa-1,5-diyne, 1-chloro-9-iodononane prepared from 1,9-dichlorononane by exchange with sodium iodide is coupled with the octa-1,5-diyne through its remaining active hydrogen atom to give 1-chloro-heptadeca-10,14-diyne, 14-diyne, which is converted through the nitrile to octadeca-11,15-diynoic acid, and then by selective hydrogenation with a Lindler catalyst to the diene; (7) cis-cis-octadeca-11,15-dienoic acid is prepared by selective hydrogenation of 1-chloroheptadeca-10,14,diyne to cis-cis-1-chloroheptadeca-10,14-diene, which is then converted into a Grignard reagent and carbonated to give the desired acid; (8) cis-cis-octadeca-10, 15-dienoic acid is prepared by first producing hepta-1,6-diyne (from sodium acetylide and 1,3-dibromopropane) and converting this to nona-1,6-diyne, 1-chloro-8-iodo-octane is coupled with the nona-1,6-diyne through its remaining active hydrogen atom to give 1-chloroheptadeca-9, 14-diyne, this is converted by selective hydrogenation with Lindlar catalyst to cis - cis - 1 - chloro - heptadeca - 9,14-diene, which is finally converted to a Grignard reagent and carbonated to give the desired acid; (9) gives a preparation of cis-cis-octadeca-10,15-dienoic acid; and (10) gives a preparation of cis-2-amino-oct-5-enoic acid. Examples 11 and 12 relate to the reaction products of cis-hept-4 enal with cysteine and b -lactoglobulin, respectively.ALSO:A precursor for the cream- or butter-like flavouring cis-hept-4-enal or trans-hept-4-enal giving the flavour during cooking or storage of food in which it is incorporated, consists of the reaction product of the hept-4-enal with an edible amino acid containing a primary amino group and a mercapto group attached to adjacent carbon atoms, or a polypeptide or protein derived from it, exemplified by cysteine or b -lactoglobulin. According to an example, b -lactoglobulin (0.5 g.) and cis-hept-4-enal (0.02 g.) were dissolved in water (20 ml.) and the solution was kept overnight in a refrigerator for the reaction product to precipitate out.ALSO:Cream- or butter-like flavour is imparted to, or enhanced in, margarine, products containing butter fat, shortenings, artificial cream, ice-cream, chocolate, soups, sauces, processed cheese, bakery products and ingredients, and confectionery such as sweets, toffees and fudge, by incorporating therein a minute proportion of cis-hept-4-enal or trans-hept-4-enal, or a precursor which forms the cis- or trans-hept-4-enal as by hydrolysis, oxidation or auto-oxidation in situ in the foodstuff, for instance during cooking or storage. The following precursors are mentioned: (1) the diethyl acetal of cis- or trans-hept-4-enal; (2) cis- or trans-hept-4-en-1-ol; (3) cis-cis-octadeca-11, 15-dienoic acid or cis-cis-octadeca-10, 15-dienoic acid and their stereoisomers, either as the free acids or in the form of their functional derivatives such as the ethyl esters, triglycerides and partial glycerides, and alkali metal salts; (4) 2-amino-oct-5-enoic acid, which is particularly effective as a precursor during the heating and frying of foods if sugars or dicarbonyl substances are present; (5) the reaction product of hept-4-enal with an edible amino acid containing a primary amino group and a mercapto group attached to adjacent carbon atoms, or a polypeptide or protein derived from it, as exemplified by cysteine or b -lactoglobulin. It is stated that cysteine and b -lactoglobulin react with the hept-4-enal apparently forming compounds with a thiazolidine ring. Larger proportions (specified) of trans-hept-4-enal are needed than when the cis-form is employed. The flavour imparted by the hept-4-enal may be supported by such additional flavouring agents as: (1) a lactone of a d - or g -hydroxy straight chain aliphatic monocarboxylic acid of from 8 to 14 carbon atoms, (2) diacetyl, or (3) a fatty acid of from 4 to 10 carbon atoms. In order to obtain a margarine that develops the same flavour as butter on heating, a precursor such as octadeca-11, 15-dienoic acid or octadeca-10 15-dienoic acid may be employed in addition to the hept-4-enal. In bakery products such as biscuits and cakes, and confectionery such as fudge, containing fat subject to autoxidation, the hept-4-enal is used in conjunction with a precursor giving rise to the free aldehyde on autoxidation. A flavouring agent comprising hept-4-enal or its precursor in a refined edible oil may be applied to foods by dipping, sprinkling or spraying. The flavouring compounds can also be applied to the crust of a bakery product or incorporated in foods by exposing them to a gas containing a sufficient amount of the vapour of the flavouring substance. According to the examples: (13) a flavouring agent for incorporation in margarine was made by dissolving in refined groundnut oil, d -hydroxy-n-dodecanoic acid lactone, d -hydroxy-n-butyric acid lactone, g -hydroxy-n-octanoic acid lactone, e -hydroxy-n-dodecanoic acid lactone, butyric, caproic caprylic and capric acids, diacetyl, acetyl methylcarbinol and cis-hept-4-enal; (16) there was incorporated into a vanilla ice-cream of 10% fat content, butyric acid, diacetyl and cis-hept-4-enal; and (20) shortbread was made from the following ingredients:- wheat flour, margarine, sugar, salt, baking powder, water and cis-cis-octadeca-11, 15-dienoic acid.
SE8182/63A 1962-07-24 1963-07-24 SE302075B (en)

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DE (4) DE1517128C3 (en)
DK (1) DK108516C (en)
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Publication number Priority date Publication date Assignee Title
NL185194C (en) * 1976-07-27 1990-02-16 Naarden International Nv METHOD FOR PREPARING PERFUME COMPOSITIONS AND METHOD FOR PREPARING AN PERFUME
EP0021481B2 (en) * 1979-06-12 1990-04-04 THE PROCTER & GAMBLE COMPANY Artifically flavoured edible oils or fats
US4338472A (en) * 1981-01-21 1982-07-06 Hydrocarbon Research, Inc. Catalytic hydrogenolysis of alditols to produce polyols
US5204023A (en) * 1989-04-12 1993-04-20 Unilever Patent Holdings B.V. Malodors reduction
GB8908199D0 (en) * 1989-04-12 1989-05-24 Unilever Plc Malodors reduction
EP0729931B1 (en) * 1995-03-03 1998-08-19 Dow Corning Corporation Process for the preparation of 1,5-hexadiene
US6790815B1 (en) 1998-07-10 2004-09-14 Procter & Gamble Company Amine reaction compounds comprising one or more active ingredient

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DE1030329B (en) * 1952-08-08 1958-05-22 Unilever Nv Process for the production of the lactone of O € -oxydodecanoic acid (ª € -oxylauric acid) serving as a flavoring agent
DE1030328B (en) * 1952-08-08 1958-05-22 Unilever Nv Process for the production of the ªŠ-oxycarboxylic acids serving as flavoring agents with 9 to lactones saturated straight-chain carbon atoms
DE1038549B (en) * 1952-08-08 1958-09-11 Unilever Nv Process for the production of ª € -oxydekaneeurelactone serving as a flavoring agent
DE1030327B (en) * 1952-08-08 1958-05-22 Unilever Nv Process for the production of the ª € -oxycaprinsaeurelactons serving as a flavoring agent
DE1077952B (en) * 1955-02-07 1960-03-17 Unilever Nv Process for preserving and flavoring fatty foods

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Publication number Publication date
ES290416A1 (en) 1963-12-01
FI40430B (en) 1968-09-30
DE1303074C2 (en) 1973-05-17
DE1517128C3 (en) 1980-09-18
DE1517128A1 (en) 1969-04-03
LU44128A1 (en) 1963-09-24
DE1493297B2 (en) 1973-01-25
DK108516C (en) 1967-12-27
GB1068712A (en) 1967-05-10
DE1493297A1 (en) 1972-04-20
DE1277836B (en) 1968-09-19
DE1795617A1 (en) 1972-08-03
DE1795617B2 (en) 1976-11-04
DE1517128B2 (en) 1973-04-26
CH470848A (en) 1969-04-15
DE1303074B (en) 1972-09-07
AT262733B (en) 1968-06-25

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