DE688379C - Process for the production of nitrogen- and sulfur-containing resins - Google Patents

Process for the production of nitrogen- and sulfur-containing resins

Info

Publication number
DE688379C
DE688379C DE1937I0057587 DEI0057587D DE688379C DE 688379 C DE688379 C DE 688379C DE 1937I0057587 DE1937I0057587 DE 1937I0057587 DE I0057587 D DEI0057587 D DE I0057587D DE 688379 C DE688379 C DE 688379C
Authority
DE
Germany
Prior art keywords
sulfur
nitrogen
containing resins
production
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE1937I0057587
Other languages
German (de)
Inventor
Dr Josef Duesing
Dr Paul Esselmann
Dipl-Ing Karl Koesslinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to DEI56786D priority Critical patent/DE676197C/en
Priority claimed from GB632837A external-priority patent/GB491565A/en
Priority claimed from DEI57563D external-priority patent/DE678907C/en
Priority claimed from DEI57565D external-priority patent/DE678908C/en
Priority to DE1937I0062013 priority patent/DE688337C/en
Priority to DE1937I0062012 priority patent/DE692695C/en
Priority to DE1937I0062014 priority patent/DE688380C/en
Priority to DE1937I0057587 priority patent/DE688379C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB14300/37A priority patent/GB496052A/en
Priority to FR49310D priority patent/FR49310E/en
Priority to FR835387D priority patent/FR835387A/en
Priority to NL86984A priority patent/NL48276C/en
Priority to NL92542A priority patent/NL48331C/xx
Publication of DE688379C publication Critical patent/DE688379C/en
Application granted granted Critical
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Description

Verfahren zur Herstellung von stickstoff- und schwefelhaltigen Harzen Es ist bereits vorgeschlagen worden (Patent 676 r97), aus cyclischem Athylenimin, Polymeren desselben oder deren Homologen und Schwefelkohlenstoff unlösliche schwefelhaltige Stoffe herzustellen, die sich durch verhältnismäßig hohen Stickstoffgehalt auszeichnen.Process for the production of nitrogen- and sulfur-containing resins It has already been proposed (patent 676 r97), from cyclic ethyleneimine, Polymers of the same or their homologues and carbon disulfide insoluble sulfur-containing To produce substances that are characterized by a relatively high nitrogen content.

Es wurde nun gefunden, daß man künstliche stickstoff- und schwefelhaltige Harze gewinnen kann, wenn man cyclisches Äthylenimin, seine Homologen, Substitutionsprodukte oder Polymeren oder Gemische von diesen Stoffen und Kohlenoxysulfid bis zur Bildung eines in Wasser und in wäßrigen Lösungen von Säuren und Alkalien unlöslichen Produktes aufeinander einwirken läßt.It has now been found that artificial nitrogen and sulfur-containing Resins can be obtained by using cyclic ethyleneimine, its homologues, substitution products or polymers or mixtures of these substances and carbon oxysulphide to the point of formation a product insoluble in water and in aqueous solutions of acids and alkalis can act on each other.

Die Umsetzung zwischen den stickstoffhaltigen Basen und dem Kohlenoxysulfid kann in wäßriger Lösung oder in organischen indifferenten Lösungsmitteln, z. B. in Kohlenwasserstoffen, Alkoholen, Essigestern o. dgl., durchgeführt werden. In allen Fällen muß die Einwirkung der beiden harzbildenden Ausgangsstoffe so lange fortgeführt werden, bis ein in Wasser und in wäßrigen Lösungen von' Säuren und Alkalien unlöslicher Stoff entstanden ist. Die Umsetzung kann durch Erhitzen beschleunigt oder beendet werden. Auch ein Erhitzen in Gegenwart von verdünnten Säuren fördert die Bildung der unlöslichen Endstoffe. Schließlich kann der noch nicht unlöslich gewordene Anteil des Umsetzungsgemisches durch Auskochen mit verdünnten Säuren oder Alkalien entfernt werden.The reaction between the nitrogenous bases and the carbon oxysulphide can in aqueous solution or in organic inert solvents such. B. in hydrocarbons, alcohols, ethyl acetate o. The like., Be carried out. In In all cases, the action of the two resin-forming starting materials must be so long be continued until one in water and in aqueous solutions of 'acids and alkalis insoluble matter has arisen. The implementation can be accelerated by heating or terminated. Heating in the presence of dilute acids is also beneficial the formation of the insoluble end products. After all, it cannot be insoluble the proportion of the reaction mixture that has become due to boiling with dilute acids or Alkalis are removed.

Die unlöslichen stickstoff- und schwefelhaltigen Harze können als Kunstharze oder als Lackkompositionen benutzt werden.The insoluble nitrogen- and sulfur-containing resins can be used as Synthetic resins or as lacquer compositions are used.

Beispiele i. In eine i 5prozentige wäßrige Lösung von Äthylenimin wird reines Kohlenoxysulfid eingeleitet; wobei man die Mengenverhältnisse so wählt, daß auf i Mol Äthylenimin i Mol Kohlenoxysulfid trifft. Die Lösung, aus der nach kurzer Zeit das ungelöste Harz ausfällt, wird einige Stunden unter Rückfluß zum Sieden erhitzt. Bei Anwendung von nicht polymerisierter Äthyleniminlösung entsteht auf diese Weise ein Harz, das nach gründlicher'-. Reinigung i4,6% Stickstoff und 22,9 Schwefel enthält und einen Schmelzpunkt von 18 i ° aufweist.Examples i. Pure carbon oxysulphide is introduced into a 5 percent aqueous solution of ethyleneimine; the proportions being chosen so that one mole of ethyleneimine meets one mole of carbon oxysulfide. The solution, from which the undissolved resin precipitates after a short time, is heated to boiling under reflux for a few hours. When using non-polymerized ethyleneimine solution, a resin is formed in this way, which after thorough'-. Cleaning i4,6% nitrogen and 22.9 sulfur and has a melting point of 1 8 i °.

2. 4,5 1 einer wäßrigen Lösung, die 5 monomeres Äthylenimin enthält, werden mit 5ooccm einer i5prozentigen Lösung von polymerem Äthylenimin vermischt, und in diese Lösung wird Kohlenoxysulfid eingeleitet, bis keine Fällung mehr auftritt. Dann wird das Gemisch einige Stunden auf dem Dampfbad erhitzt. Das gereinigte weiße Umsetzungsgut enthält 14,00/0 Stickstoff und i i,9 % Schwefel und hat den Schmelzpunkt23i°.2. 4.5 l of an aqueous solution containing 5 monomeric ethyleneimine, are mixed with 5ooccm of a 15 percent solution of polymeric ethyleneimine, and carbon oxysulphide is passed into this solution until no more precipitation occurs. Then the mixture is heated on the steam bath for a few hours. The purified white Reaction material contains 14.00 / 0 nitrogen and i i.9% sulfur and has a melting point of 23 °.

3. In 5oo ccm einer wäßrigen 2oprozentigen Lösung von N-Methyläthylenimin wird ein mit konzentrierter Schwefelsäure getrockneter Strom von Kohlenoxysulfid bei Temperaturen zwischen 25. bis 35° so lange eingeleitet, als sich der entstandene weiße Niederschlag noch vermehrt. Die Umsetzung ist beendet, wenn in einer abfiltrierten Probe der Flüssigkeit durch Kohlenoxysulfid kein weiterer Niederschlag mehr entsteht. Das Umsetzungsgemisch wird zusammen mit dem gebildeten weißen Niederschlag noch 1/2 Stunde erhitzt und nach dem Abkühlen der Flüssigkeit der Niederschlag abfiltriert und getrocknet. Zur Reinigung wird die Masse nacheinander mit verdünnter Säure, mit verdünntem Alkali und mit Wasser ausgekocht. Man erhält so ein schwachgelbes unlösliches Harz, das in heißem Eisessig, Pyridin und Anilin löslich ist.3. In 500 cc of an aqueous 2% solution of N-methylethyleneimine becomes a stream of carbon oxysulphide dried with concentrated sulfuric acid initiated at temperatures between 25. to 35 ° as long as the resulting white precipitate increased. The reaction is complete when filtered off in one Sample of the liquid by carbon oxysulphide no more precipitate forms. The reaction mixture is still together with the white precipitate formed Heated for 1/2 hour and, after the liquid had cooled, the precipitate was filtered off and dried. To clean the mass, one after the other with diluted acid, boiled with dilute alkali and water. So you get a pale yellow insoluble resin that is soluble in hot glacial acetic acid, pyridine, and aniline.

Statt N-Methyläthylenimin können auch andere N-Alkyläthylenimine verwendet werden. Wasserunlösliche Imine, wie z. B. Benzyläthylenimin, werden zweckmäßig in benzolischer Lösung umgesetzt. 4. 5o g N-Phenyläthylenimin werden in 5oo g Benzol gelöst; bei 4o° wird mit konzentrierter Schwefelsäure getrocknetes Kohlenoxysulfid in die Lösung eingeleitet. Das Umsetzungsgut scheidet sich in Form von weißen Flocken aus der Lösung aus. Es wird abfiltriert und auf dem Wasserbad einige Stunden getrocknet. Es schmilzt dabei zu einem braungelben Harz zusammen, das nach dem Abkühlen fein gepulvert und nacheinander mit ioprozentiger Schwefelsäure, 3prozentiger Natronlauge und mit heißem Wasser gewaschen wird.Instead of N-methylethyleneimine, other N-alkylethyleneimines can also be used will. Water-insoluble imines, such as. B. Benzyläthylenimin are appropriate in benzene solution implemented. 4. 50 g of N-phenylethyleneimine are dissolved in 500 g of benzene solved; at 40 °, carbon oxysulphide is dried with concentrated sulfuric acid initiated into the solution. The material to be converted separates in the form of white flakes out of the solution. It is filtered off and dried on a water bath for a few hours. It melts together to form a brown-yellow resin, which after cooling becomes fine powdered and one after the other with 10% sulfuric acid, 3% sodium hydroxide solution and washed with hot water.

5. Eine 3oprozentige wäßrige Lösung von Propylenimin wird nach Einleiten von Kohlensäure 2 Stunden bei 2o° gehalten. In der entstandenen viscosen Lösung hat sich Polypropylenimin gebildet, das wie in den vorangehenden Beispielen mit Kohlenoxysulfid umgesetzt wird. Beim Einleiten von mit konzentrierter Schwefelsäure getrocknetem Kohlenoxysulfid scheidet sich ein schwer löslicher weißer Stoff ab, der 3 Stunden im Umsetzungsgemisch auf dem Wasserbad erhitzt wird. Der Niederschlag wird von der Flüssigkeit abgetrennt, mit verdünnter Säure, verdünnter Lauge und heißem Wasser gewaschen und schließlich auf dem Wasserbad getrocknet, wobei er zu einem gelbbraunen Harz zusammenschmilzt.5. A 3% aqueous solution of propyleneimine is introduced after introduction held by carbonic acid at 20 ° for 2 hours. In the resulting viscous solution Polypropylenimine has formed, as in the previous examples with Carbon oxysulfide is implemented. When introducing with concentrated sulfuric acid a sparingly soluble white substance separates from dried carbon oxysulphide, which is heated in the reaction mixture on a water bath for 3 hours. The precipitation is separated from the liquid with dilute acid, dilute alkali and washed with hot water and finally dried on a water bath, taking it too a yellow-brown resin melts together.

Claims (1)

PATENTANSPRUCH: Verfahren- zur Herstellung von stickstoff- und schwefelhaltigen Harzen, dadurch gekennzeichnet, daß man Äthylenimin oder seine Homologen oder seine bzw. ihre Substitutionsprodukte oder seine bzw. ihre Polymeren oder Gemische von diesen Stoffen und Kohlenoxysulfid bis zur Bildung eines in Wasser und verdünnten Säuren und Alkalilen unlöslichen Stoffen aufeinander einwirken läßt.PATENT CLAIM: Process for the production of nitrogen and sulfur-containing Resins, characterized in that one ethyleneimine or its homologues or its or their substitution products or his or her polymers or mixtures of these substances and carbon oxysulphide to form one in water and diluted Allow acids and alkaline insoluble substances to act on one another.
DE1937I0057587 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins Expired DE688379C (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DEI56786D DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062013 DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062014 DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
GB14300/37A GB496052A (en) 1937-01-05 1937-05-22 Manufacture of products containing nitrogen and sulphur
FR49310D FR49310E (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
FR835387D FR835387A (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
NL86984A NL48276C (en) 1937-01-05 1938-03-19 Process for preparing nitrogen and sulfur-containing resins
NL92542A NL48331C (en) 1937-01-05 1939-03-21

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
DEI56786D DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
GB632837A GB491565A (en) 1937-03-03 1937-03-03 Manufacture of products containing nitrogen and sulphur and their application in thetextile industry
DEI57565D DE678908C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur
DEI57563D DE678907C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur
DE1937I0062014 DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062013 DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
GB14300/37A GB496052A (en) 1937-01-05 1937-05-22 Manufacture of products containing nitrogen and sulphur
FR831554T 1937-12-31
GB102138 1938-01-12
NL92542A NL48331C (en) 1937-01-05 1939-03-21
NL173088 1952-10-13

Publications (1)

Publication Number Publication Date
DE688379C true DE688379C (en) 1940-02-19

Family

ID=41650096

Family Applications (5)

Application Number Title Priority Date Filing Date
DEI56786D Expired DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062013 Expired DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 Expired DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 Expired DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062014 Expired DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins

Family Applications Before (2)

Application Number Title Priority Date Filing Date
DEI56786D Expired DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062013 Expired DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE1937I0062012 Expired DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062014 Expired DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins

Country Status (4)

Country Link
DE (5) DE676197C (en)
FR (2) FR49310E (en)
GB (1) GB496052A (en)
NL (2) NL48276C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4582900A (en) * 1983-12-17 1986-04-15 Hoechst Aktiengesellschaft Water-soluble mixed ethers of β-cyclodextrin and a process for their preparation
US4638058A (en) * 1983-12-17 1987-01-20 Hoechst Aktiengesellschaft Ethers of beta-cyclodextrin and a process for their preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4582900A (en) * 1983-12-17 1986-04-15 Hoechst Aktiengesellschaft Water-soluble mixed ethers of β-cyclodextrin and a process for their preparation
US4638058A (en) * 1983-12-17 1987-01-20 Hoechst Aktiengesellschaft Ethers of beta-cyclodextrin and a process for their preparation

Also Published As

Publication number Publication date
GB496052A (en) 1938-11-22
FR49310E (en) 1939-02-17
DE676197C (en) 1939-05-27
FR835387A (en) 1938-12-20
DE688337C (en) 1940-02-17
NL48331C (en) 1940-04-15
DE688380C (en) 1940-02-19
DE692695C (en) 1940-06-25
NL48276C (en) 1940-04-15

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