WO1989002900A1 - Polysaccharides from the endosperm of seeds of prosopis juliflora, process for extracting them, and their use - Google Patents

Polysaccharides from the endosperm of seeds of prosopis juliflora, process for extracting them, and their use Download PDF

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Publication number
WO1989002900A1
WO1989002900A1 PCT/DE1988/000608 DE8800608W WO8902900A1 WO 1989002900 A1 WO1989002900 A1 WO 1989002900A1 DE 8800608 W DE8800608 W DE 8800608W WO 8902900 A1 WO8902900 A1 WO 8902900A1
Authority
WO
WIPO (PCT)
Prior art keywords
thickening
polysaccharides
endosperm
prosopis
juliflora
Prior art date
Application number
PCT/DE1988/000608
Other languages
German (de)
English (en)
French (fr)
Inventor
Nikolaos Keramaris
Nikolaus Kottmair
Manfred Kuhn
Ulrich Beck
Friedrich Bayerlein
Original Assignee
Diamalt Aktiengesellschaft
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 Diamalt Aktiengesellschaft filed Critical Diamalt Aktiengesellschaft
Priority to IN942/CAL/88A priority Critical patent/IN170235B/en
Publication of WO1989002900A1 publication Critical patent/WO1989002900A1/de

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/46—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
    • D06P1/48—Derivatives of carbohydrates
    • 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
    • D06P5/001—Special chemical aspects of printing textile materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/016—Macromolecular compounds

Definitions

  • the Mimosacee Prosopis juliflora (also called Prosopis chilensis or Ceratonia chilensis or Mimosa juliflora) is a shrub or tree that thrives in dry areas, is particularly resistant to brackish water and industrial wastewater and is cultivated, for example, in India and Brazil to line roads, dunes to prevent hiking from supplying firewood and green fodder for camels and cattle. The fruits (pods) fall off when ripe and the roaming cattle eat this additional feed. Otherwise the pods are of no use. According to the literature ("The Wealth of India" Volume 8, 1969, 245-249) in America the pods freed from the seeds are to be ground to flour, which can be used for cakes and for beverage production. It has been found that the polysaccharide from the endosperm of the seed of Prosopis juliflora has particularly interesting chemical and physical properties.
  • galactomannans The endosperm cells of many legume seeds are known to contain polysaccharides which are galactomannans. Like starch, these are vegetable reserve polysaccharides. When the seeds germinate, they are broken down enzymatically and serve as nutrients for the seedling.
  • the collective term galactomannan or polygalactomannan encompasses all polysaccharides which are made up of galactose or mannose building blocks and moreover may also have other sugar building blocks to a lesser extent. Depending on their origin, there are a relatively large number of galactomannans that differ chemically and in their physical properties.
  • galactomannans found in the endosperm sections and seeds of various legumes such as guar, carob, tara, honey bean, flame tree, sesbania and cassia species are mainly known and used industrially.
  • DE-OS 33 35 593 describes gelling and thickening agents based on cassia galactomannans. Substituted alkyl ethers of cassia polysaccharides and their use as thickeners are disclosed in DE-OS 33 47 469. No. 2,477,544 describes carboxyalkyl ethers of polygalactomannans which are derived from guar gum, locust bean gum, honey locus, flame tree and the like, and their use as thickeners in printing pastes. Figueiredo describes in Cienc. Tecnol. Aliment. 3 (1) pp.
  • the polysaccharides according to the invention which are produced by shear grinding from the endosperm of the seed of Prosopis juliflora, are polygalactomannans from galactose and mannose in a ratio of about 1: 1. For example, an analytical ratio of 42% galactose to 58% mannose with a provenance from India was determined. Similar values were determined for other provenances / within the scope of a deviation of approx. 5%. It has surprisingly been found that this polygalactomannan is readily soluble in cold water and has a relatively high viscosity. Because of its clear solubility in cold water, it is ideal as a thickener for aqueous systems.
  • Prosopis Galactomannan does not have to improve the Solubility can be derivatized, but is already cold, clearly soluble in water as unchanged galactomannan.
  • a 1% solution in water of the galactomannan according to the invention has a viscosity of about 3000 mPas at room temperature.
  • the polygalactomannan according to the invention can be obtained from the seed by peeling methods known per se for separating the seedling and the shell.
  • the cleaned seed of Prosopis juliflora is roasted in a rotary tube oven at 200-250 ° C. for about 1-3 minutes and then the husks and seedlings are removed in peeling mills. After a visual process, the endosperm is obtained, which if necessary is subjected to the peeling process once more to improve the peeling.
  • the polygalactomannan according to the invention can then by Grinding can be released from the endosperm in a simple manner.
  • the invention thus relates to the polysaccharide essentially free of seedling and shell from the endosperm of the seeds of Prosopis juliflora (syn .: Prosopis chilensis, Ceratonia chilensis, Mimosa juliflora).
  • the polygalactomannan according to the invention has a galactose to mannose ratio of 1: 1 to 1: 1.5. These values were determined using HPLC.
  • the advantage of the polysaccharide according to the invention lies precisely in the fact that it does not need to be derivatized, the invention naturally also includes its ether and ester derivatives and its partially depolymerized derivatives.
  • Preferred ether derivatives are the C 1 -C 4 alkyl ethers and the corresponding substituted alkyl ethers, for example carboxy-C 1 -C 4 alkyl ethers and hydroxy-C 1 -C 4 alkyl ethers.
  • a particularly suitable ether derivative is hydroxypropyl ether.
  • Derivatives of the polygalactomannan according to the invention are prepared in a manner known per se. Usual methods are described for example in EP 146 911. In this way, highly viscous ether and ester derivatives soluble in cold water are obtained.
  • the depolymerization of such polygalactomannans is known per se and can be carried out thermally, oxidatively, hydrolytically or enzymatically.
  • the invention also includes the polysaccharide from the endosperm of the seed of Prosopis juliflora in partially depolymerized form.
  • the depolymerization can preferably be carried out by swelling the endosperm with water containing oxidizing agents and grinding it wet with shear during the grinding process. Hydrogen peroxide or sodium peroxide is particularly suitable as an oxidizing agent.
  • the polysaccharides according to the invention are particularly well suited for use as thickeners for aqueous systems. They are very well suited for thickening printing pastes in textile printing, for flotation of ores, as dispersing agents in paper production and finishing, for thickening food, for thickening drilling fluids and for preparing oil wells.
  • the polygalactomannans according to the invention are particularly suitable for the production of printing pastes, for thickening drilling fluids and for preparing oil wells because of their low residue solubility. Due to this low residue solubility, clogging of stencils can be avoided in textile printing, especially in rotary film printing. This eliminates costly intermediate cleaning and machine downtimes.
  • the low residue solubility is also important in the preparation of oil drilling sites (enhanced oil recovery) because the thickener according to the invention can penetrate the rock spores without clogging.
  • the polysaccharides according to the invention are readily water-soluble and therefore do not necessarily have to be derivatized, they have excellent biodegradability and are superior in this respect to the known cold-water-soluble derivatives of polysaccharides such as carboxymethyl cellulose, hydroxypropyl guar, etc.
  • the polygalactomannans according to the invention can also undergo crosslinking crosslinking reactions, and the invention therefore also includes the products crosslinked in this way.
  • crosslinkers are boric acid and its salts, as well as salts and organometallic compounds of A1, Sb, Cr, Fe, Co, Cu, Mg, Mn, Ni, Ti, V, Zn, Sn, Zr, which are particularly strong Carry out cross-linking reactions.
  • the polygalactomannans according to the invention are characterized by a particularly strong gel formation after such crosslinking reactions in aqueous solution.
  • the compounds according to the invention have particularly advantageous properties when used as thickeners, e.g. in printing pastes for aqueous textile printing and continuous dyeing of textile substrates.
  • the printing pastes can include noun dyes, acid and metal complex dyes, disperse dyes, basic dyes and others. contain.
  • the use as a thickener for aqueous systems is not limited to textile auxiliaries.
  • the natural substances according to the invention can be used for thickening. Their area of application extends to thickeners for adhesives, drilling fluids, paper coating slips, explosive solutions, plant treatment agents, for ceramic compounds and finished plasters as well as flotation aids.
  • the polysaccharides according to the invention can be used in admixture with other thickeners, for example one or more thickeners from the group consisting of starch, guar, xanthan, carrageenan, agar, locust bean gum, tare, honey bean, flame tree, sesbania, Cassi species, derivatives of such polysaccharides such as alkyl ethers, substituted alkyl ethers, carboxyalkyl ethers and phosphoric acid esters, and poly (meth) acrylates.
  • thickeners for example one or more thickeners from the group consisting of starch, guar, xanthan, carrageenan, agar, locust bean gum, tare, honey bean, flame tree, sesbania, Cassi species, derivatives of such polysaccharides such as alkyl ethers, substituted alkyl ethers, carboxyalkyl ethers and phosphoric acid esters, and poly (meth) acrylates.
  • the low-residue filterability of the polygalactomannan according to the invention can be illustrated by the suction test.
  • the polysaccharides were dissolved 1% in water (3.0 g in 297 g water).
  • the negative pressure was generated with a membrane vacuum pump KF-Neuberger type N 035 AN 18 with suction filter, manometer and vacuum meter. The time was measured until the pressure minimum was reached (approx. 800 mbar).
  • locust bean gum nor guar gum could be filtered off (suctioned off).
  • the cooked 1% aqueous batches of locust bean gum and guar gum could not be filtered off (suctioned off).
  • Trunk thickening x g combination of two
  • Printing paste 100 g C.I. Vat-Brown 5 900 g stock thickening 1 000 g
  • the stock thickening I consisted of a thickener powder combination of
  • the two stock thickenings had the same viscosity (measuring device: Brookfield RVT - 20 ° C - 20 rpm - spindle 4).
  • the pressure comparison was carried out on cotton cretonne using a rotary printing machine (System Stork, type RD-4).
  • the prints were fixed in saturated steam (10 min. - 102 ° C).
  • the comparison of the prints prepared from the thickening I and II shows that, with regard to the printing criteria: color depth, levelness, brilliance, penetration, the printing paste made from the thinner stem thickening II produced the same pressure drop as the printing ink prepared from thickening I.
  • the thickening solution of color paste 1 was prepared at 4%, while the thickening solutions 2 and 3 had to be prepared at 8% in order to have the same viscosity as color paste 1.
  • the thickening solutions consisted of:
  • Thickening solution 1 depolymerized galactomannan
  • Base guar thickening solution 3 alkoxylated galactomannan based
  • the printing was done on a Buser flat printing machine.
  • the prints were fixed in saturated steam at 102 ° C for 20 minutes.
  • the pressure prepared with the thickening according to the invention shows less frosting effect than the pressure knocked off with depolymerized galactomannan based on guar.
  • the pressure prepared with thickening solution 1 thickening according to the invention
  • gave as good a result as the printing with thickening solution 3 alkoxylated galactomannan based on guar.
  • the brilliance of the thickening according to the invention was also superior to both the depolymerized and the ethoxylated galactomannan based on guar.
  • Two carpet printing inks were prepared with the thickening A according to the invention based on Prosopis juliflora and with the comparative thickening B based on guar.
  • the carpet printing was carried out on a planographic printing machine.
  • Two carpet printing inks were prepared with the thickening A according to the invention based on Prosopis juliflora and with the comparative thickening B based on guar.
  • the carpet printing was carried out on a planographic printing machine.
  • the prints were steamed for 10 minutes at 100 ° C. without intermediate drying.
  • the thickening A according to the invention showed less frosting effect and higher color yield.
  • the results were comparable in terms of washability, brilliance and levelness.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paper (AREA)
  • Grain Derivatives (AREA)
PCT/DE1988/000608 1987-10-01 1988-09-30 Polysaccharides from the endosperm of seeds of prosopis juliflora, process for extracting them, and their use WO1989002900A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IN942/CAL/88A IN170235B (enrdf_load_stackoverflow) 1987-10-01 1988-11-11

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3733234.1 1987-10-01
DE19873733234 DE3733234A1 (de) 1987-10-01 1987-10-01 Polysaccharide aus dem endosperm des samens von prosopis juliflora, verfahren zu deren gewinnung und ihre verwendung

Publications (1)

Publication Number Publication Date
WO1989002900A1 true WO1989002900A1 (en) 1989-04-06

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PCT/DE1988/000608 WO1989002900A1 (en) 1987-10-01 1988-09-30 Polysaccharides from the endosperm of seeds of prosopis juliflora, process for extracting them, and their use

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Country Link
EP (1) EP0380528A1 (enrdf_load_stackoverflow)
JP (1) JPH03500302A (enrdf_load_stackoverflow)
DE (1) DE3733234A1 (enrdf_load_stackoverflow)
ES (1) ES2012125A6 (enrdf_load_stackoverflow)
IN (1) IN170235B (enrdf_load_stackoverflow)
WO (1) WO1989002900A1 (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5811148A (en) * 1990-05-17 1998-09-22 National Starch And Chemical Investment Holding Corporation Bulking agents and processes for preparing them from food gums

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6033469A (en) * 1995-07-25 2000-03-07 Dyckerhuff Ag Injection preparation suspension free of sodium bentonite
DE19537616C2 (de) * 1995-07-25 1998-01-22 Dyckerhoff Ag Natriumbentonitfreie Injektionsmittelsuspension
DE19630879A1 (de) * 1996-07-31 1998-02-05 Hanno Lutz Prof Dr Baumann Verfahren zur Herstellung blutverträglicher Werkstoffe durch Oberflächenbeschichtung von synthetischen Polymeren mit wasserlöslichen Substanzen aus natürlichen oder modifizierten Oligo- und Polysacchariden über kovalente Bindungen
DE19717828A1 (de) * 1997-04-26 1998-10-29 Arnold Prof Dr Wartenberg Verfahren zur Herstellung von Pigmenten aus Textilfarbstoffen und partikulierter Cellulose und Verwendung dieser Pigmente zur Herstellung von Farben, vorzugsweise von Künstlerfarben
ES2136038B1 (es) * 1998-02-03 2000-07-01 Consejo Superior Investigacion Fibra dietetica conteniendo galactomananos.
TW200503762A (en) * 2003-05-09 2005-02-01 Toho Chem Ind Co Ltd Cation-modified galactomannan polysaccharide and cosmetic composition containing the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3347469A1 (de) * 1983-12-29 1985-07-11 Diamalt AG, 8000 München Substituierte alkylaether von cassia-polysacchariden und deren verwendung als verdickungsmittel

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3347469A1 (de) * 1983-12-29 1985-07-11 Diamalt AG, 8000 München Substituierte alkylaether von cassia-polysacchariden und deren verwendung als verdickungsmittel

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 100, No. 1,2, January 1984, (Columbus, Ohio, US), McCLEARY B.V. et al., "Action Patterns and Substrate-Binding Requirements of-D-Mannanase with Mannosaccharides and Mannan-Type Polysaccharides", page 227, Abstract 2613j; & CARBOHYDR. RES., 1983, 119, 191-219. *
CHEMICAL ABSTRACTS, Volume 103, No. 20, 18 November 1985, (Columbus, Ohio, US), page 91, Abstract 162124r; & JP,A,60 144 302, (SOCIETE FRANCAISE HOECHST S.A.), 14 December 1983. *
CHEMICAL ABSTRACTS, Volume 94, No. 13, 30 March 1981, (Columbus, Ohio, US), CHURMS S.C. et al., "Smith Degradation of Gum exudates from Some Prosopis Species", pages 438-439, Abstract 99825y; & CARBOHYDR. RES., 1981, 90(2), 261-267. *
CHEMICAL ABSTRACTS, Volume 99, No. 23, 5 December 1983, (Columbus, Ohio, US), FIGUEIREDO A., "Extraction, Identification and Characteristics of the Polysaccharide from Mesquite Beans (Prosopis Juliflora DC)", page 630, Abstract 193419u; & CIENC. TECHNOL. ALIMENT., 1983, 3(1), 82-89. *
DIALOG INFORMATION SERVICES, File 5: Biosis Previews 69-88/Dec., Accession No. 86084961, SONI P.L. et al., "Sem Studies on Monosaccharides Disaccharides and Polysaccharides"; & INDIAN FOR, 114(1), 1988, 26-28. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5811148A (en) * 1990-05-17 1998-09-22 National Starch And Chemical Investment Holding Corporation Bulking agents and processes for preparing them from food gums
US6299924B1 (en) 1990-05-17 2001-10-09 National Starch And Chemical Investment Holding Corporation Bulking agents and processes for preparing them from food gums

Also Published As

Publication number Publication date
EP0380528A1 (de) 1990-08-08
JPH03500302A (ja) 1991-01-24
ES2012125A6 (es) 1990-03-01
DE3733234A1 (de) 1989-04-13
IN170235B (enrdf_load_stackoverflow) 1992-02-29

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