NO127814B - - Google Patents
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- NO127814B NO127814B NO00170961A NO17096167A NO127814B NO 127814 B NO127814 B NO 127814B NO 00170961 A NO00170961 A NO 00170961A NO 17096167 A NO17096167 A NO 17096167A NO 127814 B NO127814 B NO 127814B
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- Prior art keywords
- resin
- inclusion
- resins
- cross
- compounds
- Prior art date
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- 239000011347 resin Substances 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920000858 Cyclodextrin Polymers 0.000 claims description 7
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003463 adsorbent Substances 0.000 claims description 4
- 239000003223 protective agent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000856 Amylose Polymers 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- FSBYOEHUNSUUTD-UHFFFAOYSA-N 2-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)ethanol Chemical compound C1(C2C(O2)O1)OCCO FSBYOEHUNSUUTD-UHFFFAOYSA-N 0.000 description 1
- LSTZTHCEEPHCNQ-UHFFFAOYSA-N 3-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)-2,5-dioxabicyclo[2.1.0]pentane Chemical compound C1(C2C(O2)O1)OC1C2C(O2)O1 LSTZTHCEEPHCNQ-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical class N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- 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
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/72—Encapsulation
-
- 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
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/74—Fixation, conservation, or encapsulation of flavouring agents with a synthetic polymer matrix or excipient, e.g. vinylic, acrylic polymers
-
- 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
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Vannuoppløselig inklusjonsharpiks for anvendelse som
selektivt adsorbsjonsmiddel og beskyttelsesmiddel
samt fremgangsmåte til fremstilling derav.
Foreliggende oppfinnelse vedrører vannuoppiøsenglnKiusjoiia-harpiks for anvendelse som selektivt adsorbsjonsmiddel og beskyttelsesmiddel samt fremgangsmåte til fremstilling derav.
Med uttrykket "inklusjonsharpiks" menes harpiksholdige stoffer som er uoppløselige i vann og som har den egenskap at de danner inklusj onskomplekser,
Flere karbohydrater kan danne inklusjonskomplekser med forbindelser av lav molekylvekt. De karbohydrater som har denne egenskap har hule spiralformede eller sylindriske molekyler som har evne til å inneslutte flere forskjellige uorganiske og organiske forbindelser i hulrommene i molekylet. De resulterende inklusjonskomplekser består av to forskjellige komponenter, vertmolekylet og gjestmolekylet.
Kreftene som binder vert- og gjestmolekylene sammen er av
I
Van der Waal typen,| dvs. snarere fysiske enn kjemiske krefter. Kom-pleksene er imidlertid temmelig stabile og gjestmolekylene er beskyt-tet, f.eks. mot enzymatisk eller oksyderende angrep, og har-i alminne-lighet nedsatt flyktighet.
Et trekk ved inklusjonsharpiksen er at ved dannelsen av inklusj onskomplekser jer harpiksene selektive fordi gjestmolekylene om-sluttes ifølge derejs form og ikke ifølge ladning eller molekylvekt. En anvendelse av harpiksene er således i en ny type kromatografi hvor to eller flere strukturelle isomerer kan skilles ved bruk av en harpiks som spesifikt bare inneholder en av isomerene.
I norsk søknad nr. 157 873 beskrives en vannuoppløselig in-klus j onsharpiks sorri består av en kryssbundet forbindelse valgt fra cyklo-dextrin, acyklisk diextrin og amylose, hvilken forbindelse er kryssbundet med et kryssbindemiddel ved dens reaktive hydroksylgruppe. Disse inklusj onsharpikser som er uoppløselige i vann og oppviser inklusjonsegenskaper overfor spesielle organiske og uorganiske forbindelser, fremstilles ved at minSjt noen av de reaktive hydroksylgrupper i cyklodextrin, acyklisk dextjrin eller amylose omsettes med et kryssbindemiddel som kan danne kryssbindinger med de reaktive hydroksylgrupper, hvor det som kryssbindemiddel anvendes formaldehyd eller en bifunksjonell forbindelse.
Blant forbindelser som kan anvendes for dannelse av kryss-
1
bindinger med hydroksylgrupper er forbindelser med reaktive halogen-atomer, særlig klorjatomer, og også forbindelser med epoksygrupper. Spesielt egnede forbindelser er epiklorhydrin, diklorhydrin, diepoksy-butan, diepoksy-propyleter, etylenglykoldiepoksy-propyleter og beslekt-ede forbindelser.
Det er ijfølge oppfinnelsen funnet at det er mulig å modifi-sere strukturen til den ovenfor omtalte cyklodextrinharpiks slik at det oppnåes en-inklusjonsharpiks med andre reaksjonsegenskaper. Ifølge foreliggende oppfinnelse er det således tilveiebragt vannuoppløselig inklusjonsharpiks som er kjennetegnet ved at den består av en med hensyn til de sekundære hydroksylgrupper oksydert kryssbundet cyklodextrinharpiks.
Denne inklusjonsharpiks som oppviser inklusjonsegenskaper overfor spesielle organiske og uorganiske forbindelser og som kan anvendes som selektivt adsorbsjonsmiddel og kjemisk beskyttelsesmiddel, fremstilles ifølge oppfinnelsen ved at de sekundære hydroksylgrupper i kryssbundne cyklodefxtrinharpikser oksyderes og at det som oksydasjons-
i
middel anvendes et per.jodat. Oksvdas.i onen med per.iodat leder til dannelse av aldehydgrupper istedenfor de sekundære hydroksyl-gruppene i karbohydratet. Slike produkter er spesielt nyttige som sul-fittfjerningsmidler og er stabile overfor alkalier. De oksyderte harpikser kan om ønsket behandles med hydroksylamin, hvilket resulterer i reaksjonsprodukter av oksim-typen, som har en betydelig affinitet overfor metallioner. Strukturen til de oksyderte harpikser kan også modifiseres ved reduksjon f.eks. med natriumborhydrid eller litiumaluminium-hydrid. De oksyderte harpiksene kan om ønsket videre modifiseres f. eks. ved en annen oksydasjon med et mildt oksydasjonsmiddel slik som natriumkloritt, og dette gir de karboksylderivater, som danner stabile salter med tunge metallioner. Disse harpikser er således også i stand til å virke som meget spesifikke ioneutvekslingsharpikser.
Inklusjonsharpiksene ifølge foreliggende oppfinnelse kan anvendes til forskjellige formål. Inklusjonskompleksene kan f.eks. dannes mellom harpiksene og spesielle forbindelser som er tilstede i bland-ing med andre forbindelser. Dette kan gjøres ved ganske enkelt å til-sette harpiksen, i pulverform eller granulatform, til en oppløsning inneholdende den ønskede forbindelse og blandingen gis anledning til å nå likevektsbetingelser. Separeringen kan alternativt foretas i en kolonne ved bruk av en spesiell temperatur, pH og/eller oppløsnings-middelgradienter, idet harpiksen omslutter gjestmolekylet i overens-stemmelse med dets form. Inklusjonskomplekset kan deretter fjernes f.eks. ved filtrering eller dekantering og forbindelsen kan gjenvinnes fra komplekset f.eks. ved oppvarming til forhøyet temperatur eller ved dampdestillasjon.
Inklusjonskompleksene kan alternativt dannes ved å føre en oppløsning inneholdende den ønskede forbindelse gjennom en kolonne inneholdende inklusj onsharpiksen.
En videre anvendelse av inklusjonsharpiksene, er til stabi-lisering av flyktige og/eller ustabile stoffer slik som vitaminer og flyktige aromatiske bestanddeler som finnes i matvarer.
Følgende eksempel illustrerer oppfinnelsen.
Eksempel 1
7 g av en inklusjonsharpiks fremstilt fra cyklodextrin og epiklorhydrin, innføres i en oppløsning inneholdende 3 % vekt/volum av natriumklorid og 200 ml 0.4M natriumperjodat. Reaksjonsblandingen holdes på et mørkt sted i 24 timer ved 4°C. Det resulterende dialdehyd-derivat av harpiksen vaskes med etylenglykol og frigjøres fra jodatet
med vann. Sluttlig vaskes det med aceton og tørkes under forminsket trykk. 1 g av<1>den oksyderte harpiks tilsettes til 100 ml. 0.1 N bi-sulfittoppløsning. Når likevekt er nådd har harpiksen absorbert 5 milliekvivalenter (dvs. mer enn 50 %) av den tilstedeværende bisulfitt.
Claims (2)
1. Vannuoppløselig inklusjonsharpiks for anvendelse som selektivt adsorbsjonsmiddel og beskyttelsesmiddel,karakterisertved at den består av en med hensyn til de sekundære hydroksylgrupper oksydert kryssbundet cyklodextrinharpiks.
2. Fremgangsmåte til fremstilling av inklusjonsharpiks ifølge krav 1,karakterisert vedat de sekundære hydroksylgrupper i kryssbundne cyklodextrinharpikser oksyderes og at det som oksydasjonsmiddel; anvendes et perjodat.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH561564A CH445129A (fr) | 1964-04-29 | 1964-04-29 | Procédé pour la préparation de composés d'inclusion à poids moléculaire élevé |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127814B true NO127814B (no) | 1973-08-20 |
Family
ID=4296563
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00157873A NO126377B (no) | 1964-04-29 | 1965-04-28 | |
| NO00170961A NO127814B (no) | 1964-04-29 | 1967-12-13 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00157873A NO126377B (no) | 1964-04-29 | 1965-04-28 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3420788A (no) |
| BE (1) | BE662174A (no) |
| CH (1) | CH445129A (no) |
| DK (1) | DK132259C (no) |
| ES (1) | ES312034A1 (no) |
| GB (1) | GB1091637A (no) |
| IT (1) | IT961352B (no) |
| NL (1) | NL6505361A (no) |
| NO (2) | NO126377B (no) |
| SE (2) | SE365234B (no) |
Families Citing this family (112)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU177419B (en) * | 1978-07-13 | 1981-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing threedimensional,retentive polymers consisting of cyclodextrin and polyvinylalcohol units,capable of forming inclusion complexes in the form of bead,fibre or mainly block |
| EP0013688B1 (en) * | 1978-12-15 | 1984-02-01 | Kyoshin Co., Ltd. | A perfumed synthetic resin product and a method of producing said product |
| JPS609524B2 (ja) * | 1979-06-01 | 1985-03-11 | 理化学研究所 | シクロデキストリンの回収法 |
| HU184066B (en) * | 1979-12-28 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Plant growth regulating substance and process for preparing such compound |
| HU181733B (en) * | 1980-08-07 | 1983-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing sorbents containing cyclodextrin on cellulose base |
| JPS57130914A (en) * | 1981-02-04 | 1982-08-13 | Agency Of Ind Science & Technol | Prolongation of activity retention |
| HU189534B (en) * | 1981-09-09 | 1986-07-28 | Chinoin Rt.,Hu | Process for producing new tablets containing cyclodextrin polymer as desintegrator |
| US4448789A (en) * | 1982-08-27 | 1984-05-15 | Warner-Lambert Company | Enhanced flavor-releasing agent |
| HU191101B (en) * | 1983-02-14 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing water-soluble cyclodextrin polymers substituted with ionic groups |
| JPS6081166A (ja) * | 1983-10-11 | 1985-05-09 | Fujisawa Pharmaceut Co Ltd | ２−ニトロオキシメチル−６−クロロピリジンのβ−シクロデキストリン包接化合物およびその製造法 |
| JPS60202115A (ja) * | 1984-03-27 | 1985-10-12 | Ichiro Shibauchi | エポキシ樹脂用硬化剤 |
| US4596795A (en) * | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
| US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
| JPS61152765A (ja) * | 1984-12-27 | 1986-07-11 | Nippon Ekishiyou Kk | シクロデキストリン類で包接された化合物を含有した合成樹脂製品及びその製造方法 |
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Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801184A (en) * | 1952-01-18 | 1957-07-30 | Miyamoto Katsuhei | Colloidal suspension of amylose and alpha-amylodextrin |
| NL224464A (no) * | 1958-01-29 | |||
| US2977356A (en) * | 1958-05-27 | 1961-03-28 | Anheuser Busch | Process for preparing cross-linked starch ethers in granule form |
| US2973243A (en) * | 1958-08-26 | 1961-02-28 | Kudera Dieter | Process for producing threads, foils, tubes and the like from amylose and/or starch carbohydrates containing amylose |
| NL126243C (no) * | 1959-06-12 | |||
| US2989521A (en) * | 1959-06-30 | 1961-06-20 | Frederic R Senti | Method of cross-linking and oxidizing starch |
| US3282870A (en) * | 1963-11-29 | 1966-11-01 | Dow Chemical Co | Starch and polycarboxamide reaction products |
-
1964
- 1964-04-29 CH CH561564A patent/CH445129A/fr unknown
-
1965
- 1965-04-06 IT IT7649/65A patent/IT961352B/it active
- 1965-04-07 BE BE662174D patent/BE662174A/fr unknown
- 1965-04-20 GB GB16550/65A patent/GB1091637A/en not_active Expired
- 1965-04-20 US US449619A patent/US3420788A/en not_active Expired - Lifetime
- 1965-04-20 ES ES0312034A patent/ES312034A1/es not_active Expired
- 1965-04-27 NL NL6505361A patent/NL6505361A/xx unknown
- 1965-04-28 DK DK215765A patent/DK132259C/da active
- 1965-04-28 NO NO00157873A patent/NO126377B/no unknown
- 1965-04-28 SE SE12182/69A patent/SE365234B/xx unknown
- 1965-04-28 SE SE5582/65A patent/SE333240B/xx unknown
-
1967
- 1967-12-13 NO NO00170961A patent/NO127814B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK132259C (da) | 1976-05-03 |
| DE1493047B2 (de) | 1973-01-11 |
| GB1091637A (en) | 1967-11-22 |
| BE662174A (no) | 1965-10-07 |
| ES312034A1 (es) | 1966-02-01 |
| DE1493047A1 (de) | 1969-01-02 |
| NO126377B (no) | 1973-01-29 |
| US3420788A (en) | 1969-01-07 |
| DK132259B (da) | 1975-11-17 |
| NL6505361A (no) | 1965-11-01 |
| CH445129A (fr) | 1967-10-15 |
| IT961352B (it) | 1973-12-10 |
| SE365234B (no) | 1974-03-18 |
| SE333240B (sv) | 1971-03-08 |
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