WO1992022698A1 - Verwendung von alkylglykosiden als textilhilfsmittel - Google Patents

Verwendung von alkylglykosiden als textilhilfsmittel Download PDF

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Publication number
WO1992022698A1
WO1992022698A1 PCT/EP1992/001287 EP9201287W WO9222698A1 WO 1992022698 A1 WO1992022698 A1 WO 1992022698A1 EP 9201287 W EP9201287 W EP 9201287W WO 9222698 A1 WO9222698 A1 WO 9222698A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl glycosides
general formula
alkyl
use according
liquor
Prior art date
Application number
PCT/EP1992/001287
Other languages
German (de)
English (en)
French (fr)
Inventor
Bernd Wahle
Jörg SCHAD
Manfred Weuthen
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 EP92912343A priority Critical patent/EP0589978B1/de
Priority to JP4511039A priority patent/JPH06508184A/ja
Priority to DE59201470T priority patent/DE59201470D1/de
Publication of WO1992022698A1 publication Critical patent/WO1992022698A1/de

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • D06L1/14De-sizing
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/13Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen using inorganic agents
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/20Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/38Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table

Definitions

  • alkyl glycosides as textile additives
  • the invention relates to the use of special alkyl glycosides as surfactants in the textile pretreatment of textile fabrics, yarns or flakes.
  • the aim of the textile pretreatment is to remove the accompanying substances of the textile fabrics, yarns or flakes as easily and gently as possible, which disrupt the finishing processes, such as dyeing, printing, optical brightening or finishing.
  • the pretreated goods must not contain any disruptive amounts of dirt, preparations, sizes and natural fibers.
  • the goods must have a sufficiently high degree of whiteness and show uniform and high dye absorption and absorbency.
  • Synthetic textile fabrics or yarns generally contain spin finishes, size and dirt which are to be removed by washing processes. Natural textile fabrics and yarns are much more difficult to separate from the disruptive accompanying substances such as size, preparations, waxes, pectins etc.
  • the primary purpose is alkaline boiling.
  • Desizing and bleaching are suitable as pretreatment processes for synthetic and / or natural fibers, but are mostly chosen alone or in combination with alkaline decoction for natural fibers.
  • the textile goods are first brought into contact with a chemical-containing liquor that contains surfactants.
  • surfactants have the task of permitting wetting and penetration of the textiles and removing size, preparations, dirt of all kinds and fiber accompanying substances from the textile material.
  • Such surfactants must be alkali-stable and temperature-resistant, compatible with other finishing chemicals, such as oxidizing agents, in bleaching and desizing, and have a high affinity for fibers to deaerate textile materials.
  • the tensides should be subject to environmental contracts, that is to say they should be biodegraded well, and should not have any toxic effects on aquatic organisms.
  • alkyl glycosides Because of their biological compatibility and their known wetting properties, alkyl glycosides have recently been used increasingly in household detergents and cleaning agents. Household detergents containing alkyl glycosides in combination with at least one customary anionic surfactant are described in European patent application EP 70 074. Furthermore, liquid detergents are known from European patent application EP 105 556, which contain alkyglycosides, certain other nonionic surfactants and anionic surfactants. From international patent application WO 86/2943, alkyl detergent-containing liquid detergents are known which contain conventional anionic surfactants.
  • surfactants for textile pretreatment are subject to significantly higher requirements than household detergents.
  • surfactants for textile pretreatment need a larger chemical Show kali and temperature resistance and also solve more and above all other disruptive accompanying substances of the textile fabrics, yarns and flakes as dirt such as size, preparations, pectins etc. in a shorter time.
  • the detergent concentrates used in dilute form show in commercial operations at water hardness of 0 ° dH for household-typical soiling of the type dust-wool fat, blood, milk cocoa, dust-house fat
  • the textile pretreatment also includes sizes, preparations, pectins, hemicelluloses, (cotton) waxes, metal salts and to solve similar things.
  • the object of the present invention was to provide a surfactant aid suitable for textile pretreatment, which is resistant to chemicals and alkali, shows high wetting and dispersing capacity and the textile materials treated with it have excellent absorbency and in combination gives a high degree of whiteness with a bleach.
  • the surfactant auxiliary should be contracted to a large extent, that is, non-toxic and completely biodegradable in the shortest possible time.
  • the object was achieved by using alkyl glycosides of the general formula I
  • R 1 is an alkyl radical with 8 to 14 C atoms
  • G is a glycose unit
  • n is a number from 1 to 3 as a surfactant in the textile pretreatment of natural and / or synthetic textile fabrics, yarns or flakes.
  • textile fabrics is understood to mean woven, knitted, knitted and nonwoven fabrics.
  • the concept of textile pretreatment includes washing, alkaline boiling, bleaching and desizing.
  • alkyl glycosides used according to the invention are known compounds, their preparation in numerous publications, such as in US Pat. Nos. 3547828, 3772269, 3839318 and European patent applications EP 301 298, EP 357969, EP 362671 and German published application DE 3927919 is described.
  • the reaction products referred to as alkylglycosides can be prepared from glycoses and alcohols either by direct reaction with an excess of the alcohol and an acid as a catalyst or by transacetalization with the use of a lower alcohol as solvent and reactant.
  • the alkylglycosides used in accordance with the invention are reaction products from the glycoses glucose, fructose, mannose, galactose, talose, gulose, Allose, Al- trose, idose, arabinose, X lose, lyxose and ribose and alcohols with 8 to 14 carbon atoms, whereby the glycoses can be linked glycosidically.
  • the number of linked glycoses is characterized by the so-called degree of oligomerization, which is represented as n in general formula I.
  • the degree of oligomerization n can also assume fractional numerical values as the quantity to be determined analytically; it is usually from 1 to 3 and in particular from 1.1 to 1.4.
  • G is derived from glucose.
  • R * denotes an alkyl radical having 8 to 14 carbon atoms.
  • R * is derived from straight-chain alcohols having 8 to 14 carbon atoms, which are known to be accessible from renewable raw materials as fatty alcohols.
  • Compounds of the general formula I in which R 1 is a branched alkyl radical having 8 to 14 carbon atoms, which is derived from branched alcohols, can also be used.
  • the branched alcohols are accessible, for example, as so-called oxo alcohols by means of oxo synthesis.
  • R can of course also be mixtures of alkyl radicals having 8 to 14 carbon atoms. Mixtures of this type can be derived in particular from the technical mixtures of straight-chain alcohols with 8 to 14 carbon atoms customary in fat chemistry.
  • Alkyl glycosides of the general formula I in which R is a straight-chain alkyl radical having essentially 10 carbon atoms are particularly preferred.
  • the term “essentially” in this context means that R * represents 80 to 100% of the n-decyl radical.
  • R can be derived from alcohol mixtures which are present in amounts of 80 to 100% by weight. Contain n-decyl alcohol and in amounts of 0 to 20% by weight an alcohol with 8 to 14 carbon atoms, preferably with 8 carbon atoms.
  • Alkyl glycosides of the general formula I are very particularly preferred, in which G for a glucose unit, n is a number between 1.1 and 1.4 and R is a straight-chain alkyl radical with essentially 10 carbon atoms.
  • the alkyl glycosides to be used according to the invention may contain small amounts, preferably below 2% by weight, of unreacted alcohols having 8 to 14 carbon atoms due to the production process, which has no disadvantageous effect on the use.
  • the alkyl glycosides can be used in a simple manner as solutions or as dispersions in the pretreatment liquors.
  • Water and / or organic solvents especially n-butanol, 2-ethylhexanol and / or glycerol, can be used as solvents or dispersants.
  • the aqueous dispersions of alkyl glycosides are also understood to mean the products known to the person skilled in the art as "paste".
  • the alkyl glycosides are used in the form of their solutions or dispersions in amounts such that the active substance content of alkyl glycoside in one liter of the corresponding pretreatment liquor is in the range from 0.1 to 10 g per liter.
  • Alkyl glycosides of the general formula I are added to the wash liquor in such amounts that the active substance content of alkyl glycoside in the wash liquor is in the range from 0.5 to 2.5 g per liter of wash liquor.
  • conventional sequestering agents can be used in amounts of 0.5 to 2.5 g per liter of washing liquor of the phosphonate, gluconate and / or polyacrylate type and in particular phosphonates such as Securon ⁇ 540 from Henkel KGaA, in a mixture with alkyl glycosides.
  • the alkylglycosides are preferably used for washing synthetic textile fabrics, yarns or flakes, in particular made of polyester, polyamide, viscose, acetate fibers and / or polyacrylonitrile.
  • the washing is carried out under customary temperature conditions, preferably at 40 to 80 ° C.
  • alkyl glycosides of the general formula I are preferably used as surfactants in desizing, in alkaline boiling and / or in bleaching.
  • the alkyl glycosides are used in the liquor in the form of their aqueous solutions or dispersions in such quantities that the amount of alkyl glycoside active substance is in the range from 1 to 4 g per liter of desizing liquor.
  • the alkyl glycosides can be used in combination with conventional enzymes, such as alylases, in conventional amounts for desizing.
  • the enzymes are then generally used in amounts of 2 to 15 g per liter of desizing liquor in combination with the alkyl glycosides.
  • Desizing is carried out in a conventional manner.
  • the woven fabric obtained shows excellent degrees of desizing.
  • the alkyl glycosides are used in the form of their aqueous solutions or dispersions in such amounts that the active substance content is in the range from 0.25 to 7.5 g per liter of bleaching liquor.
  • the alkylglycosides are preferred for the bleaching of natural and / or synthetic textile fabrics, yarns or flakes, and particularly for the aqueous alkaline bleaching of cotton, cotton / polyester, cotton / polyacrylonitrile, construction wool / viscose or Cotton / polyamide used.
  • These bleaching liquors contain hydrogen peroxide or compounds that form hydrogen peroxide in water as the bleaching agent.
  • the pH of these bleaching agents is adjusted to at least 9 using alkalis, preferably sodium hydroxide and / or potassium hydroxide.
  • the bleaching liquors usually contain 5 to 100 ml of 35% by weight hydrogen peroxide, 0.5 to 50 g of sodium hydroxide and / or potassium hydroxide, 2.5 to 50 ml of stabilizers, in particular sodium and / or potassium silicate solutions, per liter, 0.1 to 1.0 g of magnesium salts, in particular magnesium sulfate, 0.5 to 10 g of sequestering agent of the phosphonate type, gluconates and / or polyacrylates and in particular phosphonates such as Securon R 540 Henkel KGaA, the rest being one liter to be filled with water.
  • the bleaching is carried out at temperatures between 20 (cold bleach) and 120 ° C (hot bleach), preferably between 70 and 120 ° C.
  • hot bleach preferably between 70 and 120 ° C.
  • the alkyl glycosides are used for bleaching according to the invention, firstly a very good liquor absorption, that is to say large amounts of bleaching liquor absorbed onto the textile fabrics, yarns or flakes, and secondly a very high degree of whiteness is obtained.
  • the textile fabrics, fibers or flakes after bleaching in the presence of alkyl glycosides are characterized by very good absorbency and show a uniform and high dye absorption capacity.
  • alkyl glycosides in the form of their aqueous solutions or dispersions are used in such amounts that the active substance content is in the range from 0.25 to 7.5 g per liter of decoction liquor.
  • the boiling liquors are all adjusted to an alkaline pH of 10 to 14. Appropriately 0.25 to 7.5 g, based on the active substance content, of alkyl glycosides in the form of their aqueous solutions or dispersions in a mixture with 2 to 100 g of alkalis, preferably sodium hydroxide and / or potassium hydroxide, 0 to 5 g of sequestering agent per liter of decoction liquor type already used.
  • the alkaline boiling can take place in a conventional manner, preferably between 95 and 120 ° C. Through the use of alkyl glycosides during boiling, very high liquor uptake can be achieved in the continuous range, which enables short contact times.
  • alkyl glycosides Through the use of the alkyl glycosides according to the invention, very good liquor absorption is achieved in all cases of textile pretreatment, which enables short contact times between the material to be treated and pretreatment baths.
  • Information on technical pretreatment which primarily depends on the textile material and the desired type of pretreatment, can also be found in Ullmann's Encyclopedia of Industrial Chemistry, volume 23, pages 29-31, Verlag Chemie, Weinheim 1983. Examples
  • Cotton twill sized with starch was impregnated on a laboratory continuous system with a liquor containing 5 g of enzyme (Enzylase R HT, from Diamalt) 5 g of alkyl glucoside according to Example A) per liter.
  • the impregnation temperature was 70 ° C. and the liquor intake was 100%.
  • steaming in saturated steam (102 ° C.) was carried out in a continuous steamer for 8 minutes. It was then washed out hot on a continuous washing machine (6 washing compartments) and dried on a tenter.
  • the iodine solution is prepared as follows: 10 g of KJ were dissolved in 100 ml of H2O, 0.635 g of iodine added, shaken and until the iodine had completely dissolved touched. The mixture was then made up to 800 ml with water and finally to 1 liter with ethanol.
  • the tissue sample was rinsed briefly with cold water, blotted with a filter paper and immediately compared with the violet scale according to TEGEWA.
  • This scale is subdivided into grades from 1-9, with grade 9 documenting complete freedom from size and from grade 6 there is a sufficiently desized product.
  • the mark 9 was determined using the violet scale, d. H. there was no more size on the goods.
  • Desized cotton twill was impregnated on a laboratory continuous system with a liquor containing 40 g NaOH (100% by weight) per liter
  • Cotton starch cleaned with starch was, as described under Example B 2), boiled alkaline and washed out, but not neutralized. Subsequently, an intermediate drying took place on the stenter before the goods were impregnated with a liquor, the per liter
  • the degree of desizing was determined by inserting a tissue sample into the test solution described in Example B 1), then rinsing with cold water, dabbing with a filter paper and immediately comparing it with the violet scale. In the case of the alkaline-boiled and then bleached goods, the rating was 8-9, d. H. the goods were almost plain free. b) Determination of the whiteness

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
PCT/EP1992/001287 1991-06-18 1992-06-09 Verwendung von alkylglykosiden als textilhilfsmittel WO1992022698A1 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP92912343A EP0589978B1 (de) 1991-06-18 1992-06-09 Verwendung von alkylglykosiden als textilhilfsmittel
JP4511039A JPH06508184A (ja) 1991-06-18 1992-06-09 織物の前処理における助剤としての特別なアルキルグリコシドの使用
DE59201470T DE59201470D1 (de) 1991-06-18 1992-06-09 Verwendung von alkylglykosiden als textilhilfsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4120084A DE4120084A1 (de) 1991-06-18 1991-06-18 Verwendung von speziellen alkylglykosiden als hilfsmittel in der textilen vorbehandlung
DEP4120084.5 1991-06-18

Publications (1)

Publication Number Publication Date
WO1992022698A1 true WO1992022698A1 (de) 1992-12-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/001287 WO1992022698A1 (de) 1991-06-18 1992-06-09 Verwendung von alkylglykosiden als textilhilfsmittel

Country Status (6)

Country Link
EP (1) EP0589978B1 (enrdf_load_stackoverflow)
JP (1) JPH06508184A (enrdf_load_stackoverflow)
DE (2) DE4120084A1 (enrdf_load_stackoverflow)
ES (1) ES2069432T3 (enrdf_load_stackoverflow)
TW (1) TW212821B (enrdf_load_stackoverflow)
WO (1) WO1992022698A1 (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0716180A1 (de) * 1994-12-08 1996-06-12 Ciba-Geigy Ag Mercerisiernetzmittelzusammensetzungen
US5741783A (en) * 1994-12-22 1998-04-21 Ciba Specialty Chemicals Corporation N-cyanomethylated chitosans and hydrolysates thereof
EP0919608A1 (en) * 1997-11-25 1999-06-02 The Procter & Gamble Company Use of a polyhydroxyfatty acid amide compound as a softening compound
CN1332012C (zh) * 1997-10-29 2007-08-15 阿克佐诺贝尔公司 含有己基糖苷作为水溶助长剂的强碱性组合物

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9618575D0 (en) * 1996-09-05 1996-10-16 Courtaulds Fibres Holdings Ltd Fibre treatment
DE10030648A1 (de) * 2000-06-29 2002-01-10 Stockhausen Chem Fab Gmbh Verwendung von Alkylpolyglucosiden als Modifizierungsmittel zur Hertellung von Cellulosefasern nach dem Viskoseverfahren
DE10303328B4 (de) * 2003-01-28 2007-04-26 A. Monforts Textilmaschinen Gmbh & Co.Kg Verfahren zum kontinuierlichen enzymatischen Entschlichten
JP5647515B2 (ja) * 2007-04-27 2014-12-24 フォルシュングスツェントルム ユーリッヒ ゲゼルシャフト ミット ベシュレンクテル ハフツングForschungszentrum Juelich GmbH アルキルポリグルコシド、共界面活性剤および高分子添加剤を含む混合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1905523A1 (de) * 1968-02-07 1969-09-25 Atlas Chem Ind Glycoside mit hoeher molekularem Alkoholrest und Verfahren zu deren Herstellung
US3640998A (en) * 1969-06-18 1972-02-08 Richard C Mansfield Alkylene oxide adducts of alkyloligosaccharides and their mixtures with alkylene oxide adducts of bord alkyl glucosides and alkanols
WO1988002041A1 (en) * 1986-09-17 1988-03-24 A.E. Staley Manufacturing Company Enhanced transfer printability treatment method and composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1905523A1 (de) * 1968-02-07 1969-09-25 Atlas Chem Ind Glycoside mit hoeher molekularem Alkoholrest und Verfahren zu deren Herstellung
US3598865A (en) * 1968-02-07 1971-08-10 Atlas Chem Ind Polyglycosides and process of preparing mono and polyglycosides
US3640998A (en) * 1969-06-18 1972-02-08 Richard C Mansfield Alkylene oxide adducts of alkyloligosaccharides and their mixtures with alkylene oxide adducts of bord alkyl glucosides and alkanols
WO1988002041A1 (en) * 1986-09-17 1988-03-24 A.E. Staley Manufacturing Company Enhanced transfer printability treatment method and composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0716180A1 (de) * 1994-12-08 1996-06-12 Ciba-Geigy Ag Mercerisiernetzmittelzusammensetzungen
US5709810A (en) * 1994-12-08 1998-01-20 Ciba Specialty Chemicals Corporation Mercerization wetting agent compositions
US5741783A (en) * 1994-12-22 1998-04-21 Ciba Specialty Chemicals Corporation N-cyanomethylated chitosans and hydrolysates thereof
CN1332012C (zh) * 1997-10-29 2007-08-15 阿克佐诺贝尔公司 含有己基糖苷作为水溶助长剂的强碱性组合物
EP0919608A1 (en) * 1997-11-25 1999-06-02 The Procter & Gamble Company Use of a polyhydroxyfatty acid amide compound as a softening compound
WO1999027045A1 (en) * 1997-11-25 1999-06-03 The Procter & Gamble Company Use of a polyhydroxy fatty acid amide compound as a softening compound

Also Published As

Publication number Publication date
DE59201470D1 (de) 1995-03-30
ES2069432T3 (es) 1995-05-01
EP0589978A1 (de) 1994-04-06
DE4120084A1 (de) 1992-12-24
TW212821B (enrdf_load_stackoverflow) 1993-09-11
JPH06508184A (ja) 1994-09-14
EP0589978B1 (de) 1995-02-22

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