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WO2008133847A1 - Procédé de fabrication d'un polysaccharide dialdéhyde ayant une pureté élevée - Google Patents

Procédé de fabrication d'un polysaccharide dialdéhyde ayant une pureté élevée Download PDF

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Publication number
WO2008133847A1
WO2008133847A1 PCT/US2008/005013 US2008005013W WO2008133847A1 WO 2008133847 A1 WO2008133847 A1 WO 2008133847A1 US 2008005013 W US2008005013 W US 2008005013W WO 2008133847 A1 WO2008133847 A1 WO 2008133847A1
Authority
WO
WIPO (PCT)
Prior art keywords
dialdehyde
polysaccharide
dextran
polysaccharide dialdehyde
salt
Prior art date
Application number
PCT/US2008/005013
Other languages
English (en)
Inventor
Jeffrey David Cohen
Henry Keith Chenault
Rinaldo S. Schiffino
Original Assignee
E.I. Du Pont De Nemours And Company
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
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to EP08743049A priority Critical patent/EP2137219A1/fr
Priority to JP2010506221A priority patent/JP2010525140A/ja
Publication of WO2008133847A1 publication Critical patent/WO2008133847A1/fr

Links

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
    • C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
    • 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

Definitions

  • the problem to be solved is to provide a method for making polysaccharide dialdehydes that provides a product that has a low level of iodine-containing species and is simple and rapid.
  • R is a hydrocarbylene group having 2 to 5 carbon atoms.
  • the purified polysaccharide dialdehyde may be dried using any suitable method, for example, using heat, vacuum, a combination of heat and vacuum, or flowing a stream of dry air or a dry inert gas such as nitrogen over the purified polysaccharide dialdehyde.
  • the purified polysaccharide dialdehyde is dried in a vacuum oven at 20 °C for about 16 to 24 hours.
  • the reactor contents were transferred to a beaker and the beaker was chilled in an ice/acetone bath until a precipitate comprising a periodate salt was formed.
  • the mixture was then transferred back to the reactor and stirred for 30 min at 2 0 C.
  • the reactor contents were filtered, yielding 17.13 g of solids.
  • the filtrate was transferred to a beaker and 18.75 g of CaCI 2 .2H 2 O was added to the filtrate.
  • the mixture was stirred for 30 min at room temperature forming a precipitate comprising calcium iodate.
  • the precipitate was filtered, yielding 21.45 g of solids.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'invention porte sur un procédé de fabrication de polysaccharide dialdéhydes, qui utilise une combinaison d'étapes de précipitation et de séparation pour purifier le polysaccharide dialdéhyde formé par oxydation d'un polysaccharide par un periodate. Le procédé est simple, rapide et fournit un polysaccharide dialdéhyde ayant de très faibles taux d'espèces à teneur en iode. Le polysaccharide dialdéhyde est particulièrement approprié pour préparer des adhésifs en hydrogel pour des applications médicales.
PCT/US2008/005013 2007-04-24 2008-04-18 Procédé de fabrication d'un polysaccharide dialdéhyde ayant une pureté élevée WO2008133847A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP08743049A EP2137219A1 (fr) 2007-04-24 2008-04-18 Procédé de fabrication d'un polysaccharide dialdéhyde ayant une pureté élevée
JP2010506221A JP2010525140A (ja) 2007-04-24 2008-04-18 高純度を有する多糖ジアルデヒドを製造する方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US92594807P 2007-04-24 2007-04-24
US60/925,948 2007-04-24

Publications (1)

Publication Number Publication Date
WO2008133847A1 true WO2008133847A1 (fr) 2008-11-06

Family

ID=39615615

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/005013 WO2008133847A1 (fr) 2007-04-24 2008-04-18 Procédé de fabrication d'un polysaccharide dialdéhyde ayant une pureté élevée

Country Status (4)

Country Link
EP (1) EP2137219A1 (fr)
JP (1) JP2010525140A (fr)
CN (1) CN101663328A (fr)
WO (1) WO2008133847A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010059279A2 (fr) 2008-11-19 2010-05-27 E. I. Du Pont De Nemours And Company Adhésif de type hydrogel pour tissus formés à partir de polysaccharide aminé et de polyéther à plusieurs bras fonctionnalisé par aldéhyde
WO2010111594A1 (fr) 2009-03-27 2010-09-30 E. I. Du Pont De Nemours And Company Adhésif et agent de scellement tissulaire comprenant un polymère de polyglycérol et d'aldéhyde
WO2011002956A1 (fr) 2009-07-02 2011-01-06 E. I. Du Pont De Nemours And Company Polysaccharides fonctionnalisés par aldéhyde
WO2011002888A2 (fr) 2009-07-02 2011-01-06 E. I. Du Pont De Nemours And Company Adhesif de type hydrogel pour tissu a usage medical
US20120009132A1 (en) * 2008-12-15 2012-01-12 Council Of Scientific & Industrial Research Transparent Xyloglucan/Chitosan Gel and a Process for the Preparation Thereof
WO2012012359A1 (fr) * 2010-07-19 2012-01-26 Actamax Surgical Materials, Llc Procédé de préparation d'un dialdéhyde polysaccharidique de pureté élevée
WO2013030264A1 (fr) 2011-08-31 2013-03-07 Ecosynth Bvba Procédé pour modifier des glucides
WO2024033633A1 (fr) * 2022-08-08 2024-02-15 Innospec Limited Composition comprenant un polysaccharide oxydé
CN118697011A (zh) * 2024-06-04 2024-09-27 广东中耀环境科技有限公司 一种高分散碱式氯化铜及其制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103030701B (zh) * 2012-12-05 2015-07-08 深圳先进技术研究院 改性淀粉交联剂的制备方法
CN103709267A (zh) * 2013-11-28 2014-04-09 江南大学 一种双醛羧甲基壳聚糖的制备方法
US10787524B2 (en) * 2015-04-03 2020-09-29 Dupont Industrial Biosciences Usa, Llc Oxidized dextran
JP6811956B2 (ja) * 2016-09-06 2021-01-13 国立大学法人北陸先端科学技術大学院大学 分解制御性ハイドロゲル
CN106835367B (zh) * 2017-02-23 2019-04-16 东北师范大学 一种交联多糖纤维及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997041899A1 (fr) * 1996-05-03 1997-11-13 Innogenetics N.V. Nouveaux medicaments contenant de la gelatine reticulee avec des polysaccharides oxydes
WO2000075070A1 (fr) * 1999-06-07 2000-12-14 Sca Hygiene Products Zeist B.V. Procede de regeneration d'acide periodique
US20050002893A1 (en) 2001-10-24 2005-01-06 Helmut Goldmann Composition consisting of a polymer containing amino groups and an aldehyde containing at least three aldehyde groups
US20060078536A1 (en) 2004-10-07 2006-04-13 Kodokian George K Polysaccharide-based polymer tissue adhesive for medical use

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997041899A1 (fr) * 1996-05-03 1997-11-13 Innogenetics N.V. Nouveaux medicaments contenant de la gelatine reticulee avec des polysaccharides oxydes
WO2000075070A1 (fr) * 1999-06-07 2000-12-14 Sca Hygiene Products Zeist B.V. Procede de regeneration d'acide periodique
US20050002893A1 (en) 2001-10-24 2005-01-06 Helmut Goldmann Composition consisting of a polymer containing amino groups and an aldehyde containing at least three aldehyde groups
US20060078536A1 (en) 2004-10-07 2006-04-13 Kodokian George K Polysaccharide-based polymer tissue adhesive for medical use

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
HALSALL ET AL., J. CHEM. SOC., 1947, pages 1427 - 1432
MO ET AL., J. BIOMATER. SCI. POLYMER EDN., vol. 11, 2000, pages 341 - 351
SEITZ ET AL., JOURNAL FOR PRAKTISHE CHEMIE (LEIPZIG), vol. 311, no. 1, 1969, pages 141 - 146
URAZ ET AL., CARBOHYDRATE POLYMERS, vol. 34, 1997, pages 127 - 130

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010059279A2 (fr) 2008-11-19 2010-05-27 E. I. Du Pont De Nemours And Company Adhésif de type hydrogel pour tissus formés à partir de polysaccharide aminé et de polyéther à plusieurs bras fonctionnalisé par aldéhyde
US20120009132A1 (en) * 2008-12-15 2012-01-12 Council Of Scientific & Industrial Research Transparent Xyloglucan/Chitosan Gel and a Process for the Preparation Thereof
US8623336B2 (en) * 2008-12-15 2014-01-07 Council Of Scientific & Industrial Research Transparent xyloglucan/chitosan gel and a process for the preparation thereof
WO2010111594A1 (fr) 2009-03-27 2010-09-30 E. I. Du Pont De Nemours And Company Adhésif et agent de scellement tissulaire comprenant un polymère de polyglycérol et d'aldéhyde
WO2011002956A1 (fr) 2009-07-02 2011-01-06 E. I. Du Pont De Nemours And Company Polysaccharides fonctionnalisés par aldéhyde
WO2011002888A2 (fr) 2009-07-02 2011-01-06 E. I. Du Pont De Nemours And Company Adhesif de type hydrogel pour tissu a usage medical
WO2012012359A1 (fr) * 2010-07-19 2012-01-26 Actamax Surgical Materials, Llc Procédé de préparation d'un dialdéhyde polysaccharidique de pureté élevée
WO2013030264A1 (fr) 2011-08-31 2013-03-07 Ecosynth Bvba Procédé pour modifier des glucides
WO2024033633A1 (fr) * 2022-08-08 2024-02-15 Innospec Limited Composition comprenant un polysaccharide oxydé
CN118697011A (zh) * 2024-06-04 2024-09-27 广东中耀环境科技有限公司 一种高分散碱式氯化铜及其制备方法

Also Published As

Publication number Publication date
EP2137219A1 (fr) 2009-12-30
CN101663328A (zh) 2010-03-03
JP2010525140A (ja) 2010-07-22

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