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WO2008007321A2 - Chitosane rÉticulÉ et procÉdÉ de rÉticulation - Google Patents

Chitosane rÉticulÉ et procÉdÉ de rÉticulation Download PDF

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Publication number
WO2008007321A2
WO2008007321A2 PCT/IB2007/052659 IB2007052659W WO2008007321A2 WO 2008007321 A2 WO2008007321 A2 WO 2008007321A2 IB 2007052659 W IB2007052659 W IB 2007052659W WO 2008007321 A2 WO2008007321 A2 WO 2008007321A2
Authority
WO
WIPO (PCT)
Prior art keywords
chitosans
ranges
degree
suspension
aliphatic aldehyde
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.)
Ceased
Application number
PCT/IB2007/052659
Other languages
English (en)
Other versions
WO2008007321A3 (fr
Inventor
Cosmo Mezzina
Giovanni Scapagnini
Ivo Volpato
Bernard Bizzini
Giovanni Franchi
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.)
Sirc SpA Natural & Dietetic Foods
Original Assignee
Sirc SpA Natural & Dietetic Foods
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 Sirc SpA Natural & Dietetic Foods filed Critical Sirc SpA Natural & Dietetic Foods
Priority to EP07805070A priority Critical patent/EP2044127A2/fr
Publication of WO2008007321A2 publication Critical patent/WO2008007321A2/fr
Publication of WO2008007321A3 publication Critical patent/WO2008007321A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof

Definitions

  • This invention relates to chitosans, which are polymers of D-glucosamine, in crosslinked form, and to a process for producing chitosans in crosslinked form.
  • Said polymers are a basic component of some diet supplements, possibly in association with other compounds, used to produce cholesterol-lowering and lipid-lowering effects and to reduce sugar absorption and body weight, as described, for example, in Italian patent 1284638 filed by the Applicant.
  • the chitosans are poly( ⁇ - 1 ,4-glucosamine).
  • chitosans are crosslinkable.
  • the crosslinking reaction involves the free amine functional groups present in the macromolecule of the chitosans. These functional groups react with a suitable crosslinker, forming stable bonds with them.
  • chitosans cross-linked according to this invention have crosslinking bonds which are irreversible under the physiological conditions of the human body.
  • the crosslinked chitosans according to this invention compared with the non-crosslinked form, therefore cannot be attacked or degraded (or are attacked or degraded to a much lesser extent) by digestive enzymes and/or the physiological conditions of the gastrointestinal tract, such as the pH. As a result, said chitosans pass through the entire digestive apparatus practically unchanged.
  • This invention consequently relates to chitosans in crosslinked form wherein the crosslink derives from the reaction of said polymer with a crosslinker chosen from among the group of aliphatic aldehydes.
  • the crosslinked chitosans according to this invention can have a very broad range of crosslinking, from totally cross-linked to very slight crosslinking.
  • degree of crosslinking means the ratio between the number of functional amine groups (-NH2) which have reacted with a functional aldehyde group of the crosslinker and the total number of functional amine groups present in the polymer.
  • the crosslinked chitosans according to the invention have a degree of crosslinking which varies between approximately 1 :10 and 1 :200, preferably between 1 :30 and 1 :150, and more preferably between 1 :60 and 1 :120.
  • the aliphatic aldehyde is preferably a hydrocarbon with a C1-C10 alky] chain.
  • the aldehyde is preferably chosen from among the monoaldehydes and dialdehydes.
  • the preferred example of monoaldehyde is formaldehyde.
  • the particularly preferred example of dialdehydes is glutaraldehyde ((OHC-(CH 2 )S-CHO)).
  • Any chitosan can be crosslinked.
  • the crosslinked chitosans used according to this invention have an apparent density which ranges between approximately 0.3 and 0.80 g/ml, and preferably between 0.5 and 0.7 g/ml.
  • the particle size of these polymers typically ranges between 80 and 400 mesh, and preferably between 80 and 20 mesh.
  • the chitosans have a degree of deacetylation which typically ranges between 89 and 95%, but those with a degree of deacetylation exceeding 90% are preferred.
  • the crosslinking process which is a further subject of this invention, comprises the following stages:
  • Said buffer solution is obtained by adding acid salts of alkaline metals to the water, preferably a pair of sodium acid phosphates, namely Na 2 HPO 4 and NaH 2 PO 4 , or the sodium carbonate/bicarbonate pair.
  • Said buffer solution has a salt molarity of between approximately 0.01 and 0.5, and preferably between 0.05 and 0.1.
  • the quantity of aliphatic aldehyde reacted with the polymer to be crosslinked is chosen on the basis of the degree of crosslinking to be obtained and the number of functional aldehyde groups in the molecule.
  • the ratio between chitosan and crosslinker, expressed as moles of glucose contained in the polymer compared with the moles of crosslinker, typically ranges between 1 :1 -1CM and 1 :1 -10- 3 .
  • the crosslinker can be added, for example, in the form of an aqueous solution.
  • the molarity of the crosslinker namely the aldehyde, can range, for example, between 0.1 and 10, and preferably between 0.5 and 2.
  • Said organic amine compound is preferably an aminoacid, such as glycine or lysine. Said amine compound is added greatly in excess of the aldehyde functions which have not yet reacted; it is generally a solution which has approximately the same molarity as the solution containing the aldehyde.
  • the suspension is preferably stirred at stages (2) and (3).

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

La présente invention porte sur des chitosanes sous forme réticulée, la réticulation résultant de la réaction desdits chitosanes avec un agent de réticulation sélectionné au sein du groupe des aldéhydes aliphatiques. La présente invention porte également sur un procédé de réticulation des chitosanes comprenant les étapes suivantes : 1) suspension de chitosane dans une solution tampon de pH compris entre 7,5 et 9,5, préférentiellement entre 8,0 et 9,0, et plus préférentiellement entre 8,1 et 8,3 (suspension 1); 2) mise en contact de la suspension (1) avec un aldéhyde aliphatique au titre d'agent de réticulation et réaction pendant 1 à 24 heures à une température comprise entre 15 °C et 40 °C (suspension 2); et éventuellement : 3) traitement de la suspension (2) par une amine organique.
PCT/IB2007/052659 2006-07-10 2007-07-06 Chitosane rÉticulÉ et procÉdÉ de rÉticulation Ceased WO2008007321A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07805070A EP2044127A2 (fr) 2006-07-10 2007-07-06 Chitosane reticule et procede de reticulation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI20061335 ITMI20061335A1 (it) 2006-07-10 2006-07-10 Chitosano reticolato e processo di reticolazione
ITMI2006A001335 2006-07-10

Publications (2)

Publication Number Publication Date
WO2008007321A2 true WO2008007321A2 (fr) 2008-01-17
WO2008007321A3 WO2008007321A3 (fr) 2008-03-20

Family

ID=38846828

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2007/052659 Ceased WO2008007321A2 (fr) 2006-07-10 2007-07-06 Chitosane rÉticulÉ et procÉdÉ de rÉticulation

Country Status (3)

Country Link
EP (1) EP2044127A2 (fr)
IT (1) ITMI20061335A1 (fr)
WO (1) WO2008007321A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018119320A1 (fr) * 2016-12-21 2018-06-28 Cresilon, Inc. Compositions hémostatiques comprenant des agents antifibrinolytiques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH596233A5 (fr) * 1975-04-10 1978-03-15 Nestle Sa
US5019509A (en) * 1988-04-20 1991-05-28 Genetics Institute, Inc. Method and compositions for the production of l-alanine and derivatives thereof
US5328939A (en) * 1993-04-27 1994-07-12 Alliedsignal Inc. Rigid materials having high surface area and low density
DE19920557B4 (de) * 1999-05-05 2004-09-09 Biotec Asa Verfahren zur Herstellung von Kollagenfreien kosmetischen Zubereitungen
ATE494309T1 (de) * 2001-11-15 2011-01-15 Biosyntech Canada Inc Zusammensetzung und verfahren um chitosan unter neutralen bedingungen homogen zu modifizieren oder vernetzen

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018119320A1 (fr) * 2016-12-21 2018-06-28 Cresilon, Inc. Compositions hémostatiques comprenant des agents antifibrinolytiques

Also Published As

Publication number Publication date
EP2044127A2 (fr) 2009-04-08
ITMI20061335A1 (it) 2008-01-11
WO2008007321A3 (fr) 2008-03-20

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