WO1997008208A1 - Verfahren zur herstellung versprühbarer kationischer biopolymere - Google Patents

Verfahren zur herstellung versprühbarer kationischer biopolymere Download PDF

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Publication number
WO1997008208A1
WO1997008208A1 PCT/EP1996/003635 EP9603635W WO9708208A1 WO 1997008208 A1 WO1997008208 A1 WO 1997008208A1 EP 9603635 W EP9603635 W EP 9603635W WO 9708208 A1 WO9708208 A1 WO 9708208A1
Authority
WO
WIPO (PCT)
Prior art keywords
chitosans
cationic biopolymers
hydrogen peroxide
process according
weight
Prior art date
Application number
PCT/EP1996/003635
Other languages
German (de)
English (en)
French (fr)
Inventor
Peter Horlacher
Rolf Wachter
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU68739/96A priority Critical patent/AU6873996A/en
Priority to EP96929271A priority patent/EP0847403A1/de
Publication of WO1997008208A1 publication Critical patent/WO1997008208A1/de
Priority to NO975791A priority patent/NO975791D0/no

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024Homoglycans, 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
    • C08B37/00272-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003Chitin, 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/736Chitin; Chitosan; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the invention relates to a method for producing sprayable cationic biopolymers by degrading chitosan powders with hydrogen peroxide.
  • Chitosans are biopolymers and belong to the group of hydrocolloids. Chemically speaking, they are partially deacetylated chitins of different molecular weights that contain the - idealized - following idealized monomer building block:
  • chitosans are cationic biopolymers under these conditions.
  • the positively charged chitosans can interact with oppositely charged surfaces and are therefore used in cosmetic hair and body care products
  • a problem in the production of chitosans is that the aqueous or glycolic acid solutions of the products have too high a viscosity for the production of spray formulations even when diluted strongly (1 to 3% by weight), so that the incorporation of Chitosan, an excellent film-forming agent, for example in hair sprays, is not readily possible.
  • Another disadvantage is that the chitosans have a reddish color due to the production process, which is not desirable for a large number of cosmetic applications
  • the object of the invention was therefore to develop a process for the production of cationic biopolymers, especially chitosans, whose solutions are low-viscosity at the same time, can be easily sprayed and have an advantageously high color quality.
  • the invention relates to a process for the preparation of sprayable cationic biopolymers, in which powdered chitosans are broken down in a mixing device with an aqueous hydrogen peroxide solution and then dissolved in polar media
  • the selection of the chitosans to which the degradation process extends is not critical in itself. This means that neither the degree of deacylation nor the average molecular weight of the biopolymers have a significant influence on the resulting viscosity, color and stability of the products.
  • the grain size of the chitosan used there have been slight advantages for microcrystalline products, but the use of chitosans of conventional grain size distribution, such as those that occur in spray drying, steam drying or freeze drying, if necessary after subsequent mechanical comminution and autoclaving, leads to excellent product qualities .
  • the method is also applicable to derivatized chitosans such as e.g. quaternary products of the type of hydroxypropylchitosan and applicable to anionic reaction products of chitosans with dicarboxylic anhydrides.
  • the chitosan powder which may have a residual moisture content of 5 to 35% by weight, is placed in a mixer, for example a ploughshare mixer from Lödige or a Drais mixer, and the corresponding amount of hydrogen peroxide solution is added. If necessary, the product can then be subjected to further drying. The degradation is usually carried out over a period of 0.5 to 5, preferably 1 to 3, hours. Practically colorless, storage-stable products are obtained whose solutions can be easily sprayed.
  • Polar media for example a ploughshare mixer from Lödige or a Drais mixer
  • Suitable solvents for the degraded chitosan powder are water and organic acids, preferably glycolic or acetic acid.
  • the powders are usually dissolved in amounts of 0.5 to 5 and preferably 1 to 3% by weight.
  • the chitosan additives obtainable by the process according to the invention are dissolved in water or organic acids, the 1 to 5% by weight solutions show a surprisingly low viscosity and can be sprayed easily. They are also practically colorless and stable in storage.
  • the cationic biopolymers obtainable by the process according to the invention are therefore suitable • both as powder and in the form of said solutions - as raw materials for the preparation of hair and body preparations, in which they are present in amounts of 0.5 to 10, preferably 1 to 5 wt .-% - based on the agent - may be included.
  • Another object of the invention therefore relates to the use of the chitosans obtainable by the process described for the production of spray formulations, in particular hair sprays.
  • a typical spray formulation is shown in Table 1; Percentages as% by weight.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
PCT/EP1996/003635 1995-08-28 1996-08-19 Verfahren zur herstellung versprühbarer kationischer biopolymere WO1997008208A1 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU68739/96A AU6873996A (en) 1995-08-28 1996-08-19 Process for producing sprayable cationic biopolymers
EP96929271A EP0847403A1 (de) 1995-08-28 1996-08-19 Verfahren zur herstellung versprühbarer kationischer biopolymere
NO975791A NO975791D0 (no) 1995-08-28 1997-12-09 Fremgangsmåte for fremstilling av spraybare, kationiske biopolymerer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19537001A DE19537001C2 (de) 1995-08-28 1995-08-28 Haarsprays
DE19537001.5 1995-08-28

Publications (1)

Publication Number Publication Date
WO1997008208A1 true WO1997008208A1 (de) 1997-03-06

Family

ID=7774028

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/003635 WO1997008208A1 (de) 1995-08-28 1996-08-19 Verfahren zur herstellung versprühbarer kationischer biopolymere

Country Status (5)

Country Link
EP (1) EP0847403A1 (no)
AU (1) AU6873996A (no)
DE (1) DE19537001C2 (no)
NO (1) NO975791D0 (no)
WO (1) WO1997008208A1 (no)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6444659B1 (en) 1996-11-28 2002-09-03 Cognis Deutschland Gmbh Use of mixtures of active substances, containing phytostenols and/or phytostenol esters and potentiators, for the production of hypocholesterolemic agents
DE19730649C1 (de) 1997-07-17 1998-09-24 Henkel Kgaa Detergensgemische
JP2002520511A (ja) 1998-07-16 2002-07-09 コグニス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Pitエマルジョンの使用
DE19911040A1 (de) 1999-03-12 2000-09-21 Cognis Deutschland Gmbh Tensidgranulate
ATE304343T1 (de) 1999-07-02 2005-09-15 Cognis Ip Man Gmbh Mikrokapseln - iv
ATE258417T1 (de) 1999-07-02 2004-02-15 Cognis Iberia Sl Mikrokapseln - i
DE59912559D1 (de) 1999-07-02 2005-10-20 Cognis Ip Man Gmbh Mikrokapseln - III
ES2213948T3 (es) 1999-07-02 2004-09-01 Cognis Iberia, S.L. Microcapsulas ii.
DE19960632A1 (de) * 1999-12-16 2001-07-05 Cognis Deutschland Gmbh Kosmetische Mittel enthaltend natürliche Chitosane
DE10014529A1 (de) 2000-03-23 2001-09-27 Cognis Deutschland Gmbh Desodorierende Zubereitungen mit nanoskaligen Chitosanen und/oder Chitosanderivaten
DE10018812A1 (de) 2000-04-15 2001-10-25 Cognis Deutschland Gmbh Verfahren zur Herstellung von nichtionischen Tensidgranulaten
FR2814380B1 (fr) 2000-09-25 2002-11-08 Serobiologiques Lab Sa Poudre de microcapsules et procede d'obtention
DE10105623A1 (de) 2001-02-08 2002-08-14 Cognis Deutschland Gmbh Verfahren zur antibakteriellen Ausrüstung von Fasern oder Vliesstoffen
DE102004007115A1 (de) 2004-02-13 2005-08-25 Cognis Deutschland Gmbh & Co. Kg Chitosanhaltige Wundauflagen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0222301A (ja) * 1988-07-12 1990-01-25 Nippon Kayaku Co Ltd 水溶性キトサンの製造方法
CN1082883A (zh) * 1993-05-18 1994-03-02 国家海洋局杭州水处理技术开发中心 一种含壳聚糖的发胶

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3903797A1 (de) * 1989-02-09 1990-08-16 Hoechst Ag Verfahren zur herstellung von aktivierten chitosanen und deren verwendung bei der herstellung von chitosanderivaten
FI86068C (fi) * 1989-10-20 1992-07-10 Firextra Oy Foerfarande foer framstaellning av kitosan och andra produkter fraon skal av organismer, isynnerhet fraon skal av havsorganismer.
JP2779555B2 (ja) * 1991-04-05 1998-07-23 花王株式会社 毛髪化粧料
DE4343378C1 (de) * 1993-12-18 1995-03-30 Kao Corp Gmbh Haarpflegemittel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0222301A (ja) * 1988-07-12 1990-01-25 Nippon Kayaku Co Ltd 水溶性キトサンの製造方法
CN1082883A (zh) * 1993-05-18 1994-03-02 国家海洋局杭州水处理技术开发中心 一种含壳聚糖的发胶

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 117, no. 26, 28 December 1992, Columbus, Ohio, US; abstract no. 258043, "Oxidative degradation of chitosan in the presence of hydroperoxide" XP002019681 *
CHEMICAL ABSTRACTS, vol. 122, no. 4, 23 January 1995, Columbus, Ohio, US; abstract no. 38524, "Hair sprays containing chitosan and surfactants" XP002019682 *
CHEMICAL ABSTRACTS, vol. 92, no. 18, 1980, Columbus, Ohio, US; abstract no. 148883, page 121; column r; XP002019680 *
PATENT ABSTRACTS OF JAPAN vol. 14, no. 171 (C - 706)<4114> 3 April 1990 (1990-04-03) *
SHENG Y. ET AL., ZHONGGUO YAOKE DAXUE XUEBAO, vol. 23, no. 3, 1992, CHINA, pages 173 - 176 *

Also Published As

Publication number Publication date
DE19537001C2 (de) 1997-12-11
NO975791L (no) 1997-12-09
DE19537001A1 (de) 1997-03-06
AU6873996A (en) 1997-03-19
NO975791D0 (no) 1997-12-09
EP0847403A1 (de) 1998-06-17

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