WO1999064659A1 - Alkyl polyglycosides and alkyl sulfates as penetrants in mercerizing baths - Google Patents

Alkyl polyglycosides and alkyl sulfates as penetrants in mercerizing baths Download PDF

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Publication number
WO1999064659A1
WO1999064659A1 PCT/US1999/011807 US9911807W WO9964659A1 WO 1999064659 A1 WO1999064659 A1 WO 1999064659A1 US 9911807 W US9911807 W US 9911807W WO 9964659 A1 WO9964659 A1 WO 9964659A1
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Prior art keywords
alkyl
composition
sulfates
general formula
glycosides
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PCT/US1999/011807
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French (fr)
Inventor
Howard Cole
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Cognis Corporation
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Publication date
Priority to US8879198P priority Critical
Priority to US60/088,791 priority
Priority to US31433299A priority
Priority to US09/314,332 priority
Application filed by Cognis Corporation filed Critical Cognis Corporation
Publication of WO1999064659A1 publication Critical patent/WO1999064659A1/en

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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • 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 System
    • 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
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/262Sulfated compounds thiosulfates
    • 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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03Polysaccharides or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146Sulfuric acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives

Abstract

Blends of alkyl polyglycosides and alkyl sulfates are useful as wetting agents and textile pretreatment penetrants in baths containing high concentrations of alkali metal hydroxides.

Description

ALKYL POLYGLYCOSIDES AND ALKYL SULFATES AS PENETRANTS IN MERCERIZING BATHS
Background of the Invention
Field of the Invention
This invention relates to the use of blends of alkyl polyglycosides with various alkyl sulfates as wetting agents and textile pretreatment penetrants in baths containing extremely high concentrations of caustic soda, and more particularly, for the mercerization of cotton yarn, knit goods and woven goods. The object of pretreating textiles is to free the textile materials, yarns or flocks in a simple and careful manner from impurities which interfere with various treatment processes, such as dyeing, printing, optical brightening or finishing. In dyeing, for example, the pretreated material must not contain any troublesome quantities of soil, finishes, sizes and natural fiber impurities. At the same time, the material must have a sufficient degree of whiteness, uniformity, high dye- ability and absorbency. Synthetic sheet-form textile materials or yarns generally contain spinning finishes, size and soil which should be removed by washing processes. Natural textile materials and yarns are much more difficult to free from troublesome impurities, such as size, finishes, waxes, pectins, etc. In addition to desizing, alkaline scouring is mainly used for this purpose. Desizing and bleaching are suitable pretreatments for synthetic and/or natural fibers, but are generally applied to natural fibers either individually or in combination with alkaline scouring. In the above-mentioned pretreatments, namely washing, alkaline scouring, desizing and bleaching, the textile material is first contacted with a chemical liquor containing surfactants.
Mercerization is a customary step in the processing of cellulose- containing fiber materials and consists in treating these materials with aqueous alkali metal hydroxide. Mercerization wetting compositions must meet various application requirements. On the one hand, they must develop adequate wetting power in the strongly alkaline mercerizing liquors. Since in high-speed mercerizing machines the material to be mercerized moves through the liquor at high speed, it has to be wetted within a shorter time than is the case in machines working at slower speed. The higher speed of the material to be mercerized is responsible for increasing foaming on the liquor, which for example in yarn mercerization prevents not only rapid but also uniform wetting of the yarn. A further criterion for a good mercerization wetting composition is therefore the prevention of foaming in the mercerizing liquor. Furthermore, the formation of voluminous foam layers also interferes with the concentrating and recovery of the alkali metal hydroxide in the wash baths following the mercerizing bath.
Mercerization imparts to cellulose fibers for example higher luster. At the same time, their dye affinity and the breaking strength are improved. These fibers are for this purpose treated with concentrated alkali metal hydroxide solutions (about 22 to 28%), for example aqueous solutions of lithium, sodium or potassium hydroxide or mixtures of these hydroxides. In the process, the fibers can be subjected to a simultaneous drawing step, which makes it possible to achieve a further increase in the luster effect. The most frequently employed variant is cold mercerization (in contradistinction to hot mercerization, which is carried out at a bath temperature of 20°-80°C); In cold mercerization, the bath temperature is from about -20° to +20° C. Special effects, for example transparency effects, can be obtained by using baths cooled down to -20° C. Preferably, however, the temperature is 5° to 20° C. Depending on whether the fibers are mercerized in the dry, prescoured or prewetted state, the mercerization is known as dry or wet mercerization. Especially the variant of dry mercerization understandably makes the use of highly effective mercerization wetting compositions necessary.
Discussion of Related Art
By virtue of their biological compatibility and their known wetting properties, alkyl glycosides have recently been used to an increasing extent in domestic detergents. However, surfactants for the pretreatment of textiles have to meet far more stringent requirements than domestic detergents. Thus, surfactants for the pretreatment of textiles must have a higher resistance to chemicals and heat and, in addition, have to separate more and, above all, other troublesome impurities from the textile materials, yarns and flocks than soil, such as sizes, finishes, pectins, etc., in a shorter time.
One such attempt to provide a mercerization wetting composition is disclosed in U.S. Patent 5,464,547 which employs carbohydrate-based materials such as alkyl glycosides or alkyl carboxamidoglycosides. In addition, EP-A-0 102 930 discloses mercerization wetting compositions which are based on sulfuric esters of fatty alcohols and which are not only high-wetting but also low- foaming in use. Unfortunately, these wetting compositions are less advantageous from an ecological point of view, since they are slow to biodegrade.
The problem addressed by the present invention was to provide a surfactant-containing composition suitable for the pretreatment of textiles which would be resistant to chemicals and alkalis, would have a high wetting and dispersing power and would provide the treated textile materials with excellent absorbency and, in combination with a bleach, with a high degree of whiteness. In addition, the surfactant-containing composition would be ecologically safe, i.e. would be non-toxic and completely biodegradable in a short time.
Description of the Invention
This problem has been solved by the use of alkyl glycosides corresponding to general formula I
R1 - O - (G)n (I) in which R is a C8.14 alkyl radical, G is a glycose unit and n is a number of 1 to 3, in combination with various alkyl sulfates as surfactant-containing compositions in the mercerizing of cotton sheet-form textile materials, yarns or flocks.
In the context of the invention, sheet-form textile materials are understood to be woven and knitted fabrics and nonwovens. The textile pretreatment encompasses washing, alkaline scouring, bleaching and desizing. The term alkyl glycosides is intended as usual to apply to alkyl monoglycosides (n = 1 ) and to mixtures thereof with alkyl oligoglycosides having a degree of oligomerization n of no higher than 3.
The alkyl glycosides used in accordance with the invention are compounds known per se the production of which is described in numerous publications, for example in U.S. Patents 3,547,828, 3,772,269 and 3,839,318, in European patent applications EP 301 298, EP 357 969 and EP 362 671 and in DE-OS 39 27 919. The reaction products of glycoses and alcohols referred to as alkyl glycosides may be prepared either by direct reaction with an excess of the alcohol and an acid as catalyst or by transacetalization using a lower alcohol as solvent and reactant. The alkyl glycosides used in accordance with the invention are reaction products of the glycoses glucose, fructose, mannose, galactose, talose, gulose, allose, altrose, idose, arabinose, xylose, lyxose and ribose and alcohols containing 8 to 14 carbon atoms wherein the glycoses may be attached to one another by glycoside bonds. The number of glycoses attached to one another is characterized by the so-called degree of oligomerization which is denoted as n in general formula I. As an analytically determined value, the degree of oligomerization n may also be an uneven number. It is generally between 1 and 3 and, more particularly, between 1.1 and 1.4. The glycose units derived from the glycoses mentioned are denoted by the letter G in general formula I. In the context of the invention, G is preferably derived from glucose. R in general formula I is an alkyl radical containing 8 to 14 carbon atoms. R1 is best derived from linear alcohols containing 8 to 14 carbon atoms which, as fatty alcohols, can be obtained in known manner from renewable raw materials. It is also possible to use compounds corresponding to general formula I in which R1 is a branched alkyl radical containing 8 to 14 carbon atoms which is derived from branched alcohols. The branched alcohols may be obtained, for example, as so-called oxoalcohols by oxosynthesis. R1 may of course also represent mixtures of alkyl radicals containing 8 to 14 carbon atoms. Mixtures such as these may be derived in particular from mixtures of linear alcohols containing 8 to 14 carbon atoms typically encountered in oleochemistry. Alkyl glycosides corresponding to general formula I in which R1 is a linear alkyl radical containing 8 to 12 carbon atoms, are preferred for the purposes of the invention. Alkyl glycosides corresponding to general formula I in which R1 is a linear alkyl radical essentially containing 10 carbon atoms, are particularly preferred. In the context of the invention, the term "essentially" in this connection means that 80 to 100% of R1 represents the n-decyl radical. Accordingly, R1 may be derived from alcohol mixtures which contain n-decyl alcohol in quantities of 80 to 100% by weight and an alcohol containing 8 to 14 carbon atoms and preferably 8 carbon atoms in quantities of 0 to 20% by weight. Alkyl glycosides corresponding to general formula I in which G is a glucose unit, n is a number of 1.1 to 1.4 and R1 is a linear alkyl radical essentially containing 10 carbon atoms, are most particularly preferred.
From their production, the alkyl glycosides to be used in accordance with the invention may contain small quantities, preferably below 2% by weight, of unreacted alcohols containing 8 to 14 carbon atoms, although this does not adversely affect their use.
The alkyl glycosides may readily be used in the form of solutions or dispersions in the pretreatment liquors. Water and/or organic solvents, above all n-butanol, 2-ethyl hexanol and/or glycerol, may be used as solvents or dispersants. Aqueous solutions or aqueous dispersions of alkyl glycosides, which contain water in quantities of 50 to 100% by weight as solvent or dispersant and organic solvents in quantities of 0 to 50% by weight, based on solvent and dispersant, are preferred. Aqueous dispersions of alkyl glycosides are also understood to include the products known to the expert as "pastes". In general, the alkyl glycosides are used in the form of solutions or dispersions in such quantities that the active substance content of alkyl glycoside in 1 liter of the corresponding pretreatment liquor is in the range from 0.1 to 10 g. per liter. The alkyl sulfates, also known as fatty alcohol sulfates, employed with the alkyl glycosides in the pretreatment compositions of this invention correspond to general formula II
R - CH2 - O - S03 Na (II) in which R is a C6.8 alkyl radical. Preferably, the fatty alcohol sulfates employed in the composition of this invention are selected from the group consisting of 2-ethylhexyl sulfate and n- octyl sulfate, sodium salt.
The alkyl glycosides and alkyl sulfates employed in this invention may be present in a weight ratio of from about 80:20 to 20:80, preferably in a weight ratio of from about 60:40 to 40:60.
According to the invention, the surfactant combination is preferably used for the bleaching of natural or synthetic sheet-form textiles, yarns or flocks and, more particularly, for the aqueous alkaline bleaching of cotton, cotton/polyester, cotton/polyacrylonitrile, cotton/viscose or cotton/polyamide. The bleaching liquors contain as bleaching agent hydrogen peroxide or compounds which form hydrogen peroxide in water. The ph value of the bleaches is adjusted to at least 9 with alkalis, preferably sodium hydroxide and/or potassium hydroxide. The bleaching liquors typically contain, per liter, 5 to 100 ml 35% by weight hydrogen peroxide, 0.5 to 50 g. sodium hydroxide or potassium hydroxide, 2.5 to 50 ml stabilizers, more particularly sodium or potassium silicate solutions, 0.1 to 1.0 g. magnesium salts, more particularly magnesium sulfate, 0.5 to 10 g. sequestrants of the phosphorate, gluconate or polyacrylate type, more particularly phosphonates such as Securon® 540 (a product of Henkel KGaA), the balance to 1 liter being made up by water. Bleaching is carried out at temperatures of 20° C (cold bleaching) to 120° C (hot bleaching) and preferably at temperatures of 70 to 120° C. The use of the alkyl glycosides and alkyl sulfates in accordance with the invention for bleaching is distinguished on the one hand by very good liquor uptake, i.e., large quantities of bleaching liquor are absorbed by the sheet- form textile materials, yarns or flocks, and on the other hand by a very high degree of whiteness. In addition, the sheet-form textiles, fibers or flocks are characterized after bleaching in the presence of alkyl glycosides and alkyl sulfates by very high absorbency and by a high and uniform dye absorption capacity. For the alkaline scouring or mercerizing of cotton-containing sheet-form textile materials, yarns or flocks, preferably for pure cotton, the alkyl glycosides and alkyl sulfates are used in the form of aqueous solutions or dispersions in such quantities that the active substance content of alkyl glycoside is in the range from 0.25 to 7.5 g. per liter scouring liquor, and that of the alkyl sulfates is in the range from 0.1 to 7.25 g. per liter scouring liquor. The scouring liquors are generally alkalized to a pH value of 10 to 14. The alkyl glycosides and alkyl sulfates are used in admixture with 2 to 300 g. alkalis, preferably sodium hydroxide or potassium hydroxide, and 0 to 5 g. sequestrants of the above- described type, per liter scouring liquor. Alkaline scouring may be carried out in the usual way, preferably at temperatures of 95°C to 100° C. Very high liquor uptakes which allow short contact times can be obtained by the use of alkyl glycosides and alkyl sulfates for continuous scouring.
Additions of typical foam inhibitors, such as silicones, mineral oils or phosphoric acid esters, may be of advantage for continuous textile pretreatment processes.
In all textile pretreatments, the use of the alkyl glycosides and alkyl sulfates in accordance with the invention provides for very high liquor uptakes which in turn allow short contact times between the material to be treated and the pretreatment baths. In addition, the surfactant combination is readily biodegradable and contains no phosphates or phenols. Further, mercerization wetting compositions of the invention also permit a rapid and trouble-free recovery of the alkali metal hydroxide from the wash baths following the mercerizing bath. In the course of distillative removal of water from these baths to concentrate the alkali metal hydroxide to the alkali metal hydroxide content of the mercerizing bath, these mercerization wetting compositions have only a very minimal tendency to form a foam. The concentrated alkali metal hydroxide solution obtained can then be re-used in the mercerizing bath.
The examples which follow illustrate the invention without limiting it thereto. Parts and percentages are by weight, unless otherwise stated.
Example I
Desized, scoured cotton twill was impregnated, wet on wet, in a continuous laboratory machine with an aqueous liquor containing, per liter, 250 g. NaOH (100%). 1 to 5 g. alkyl glucoside having a degree of oligomerization (n) of 1.25 and obtained by direct synthesis from decanol and anhydrous glucose, and 1 to 4 g. of a sodium salt of an alkyl sulfate based on n-octanol or 2 ethylhexanol. The impregnation temperature was 70° F, and the liquor uptake was
60% owg (120% owg total - 60% original water content). After impregnation, the fabric was continuously held for 30 to 60 seconds, followed by washing and neutralization carried out in a continuous washing range with 4 to 6 washing compartments.
Evaluation
To determine the effect of the mercerization process, the fabric was tested using the AATCC Test Method 89-1994 "Mercerization in Cotton" which produces a Barium Number that is a measure of the degree of mercerization. The higher the Barium Number, the higher the degree of mercerization. The results are shown in Table 1.
Table 1 Treatment Barium Number
1. bleached, unmercerized 100.0
2. mercerized, sodium 2-ethylhexyl sulfate 125.9 3. mercerized, 80:20 sodium 2-ethylhexyl sulfate: 137.0
GLUCOPON® 425 N 4. mercerized, 70:30 sodium 2-ethylhexyl sulfate: 140.7 GLUCOPON®425 N
5. mercerized, 60:40 sodium 2-ethylhexyl sulfate: 151.8 GLUCOPON®425 N 6. mercerized, 80:20 sodium N-octyl sulfate: 148.1
GLUCOPON®425 N
7. mercerized, 70:30 sodium N-octyl sulfate: 140.7 GLUCOPON®425 N
8. mercerized: 60:40 sodium N-octyl sulfate: 144.1 GLUCOPON®425 N
Note: GLUCOPON® 425 N is a C8 - C16 alkyl polyglucoside having a degree of oligomerization n of about 1.6.

Claims

What is Claimed is:
1. The process of treating textile materials comprising contacting said textile materials with a treatment composition containing alkyl glycosides corresponding to general formula I
R1 - O - (G)n (I) in which R1 is a C8.14 alkyl radical, G is a glycose unit and n is a number of 1 to 3, and alkyl sulfates, corresponding to general formula II
R-CH2-0-S03 Na (II) in which R is a C6.8 alkyl radical.
2. A process as in claim 1 wherein R1 is a linear C8.12 alkyl radical.
3. A process as in claim 1 wherein in said alkyl glycosides corresponding to general formula I, n is a number of 1.1 to 1.4.
4. A process as in claim 1 wherein G is a glucose unit.
5. A process as in claim 1 wherein said alkyl sulfates are selected from the group consisting of 2-ethylhexyl sulfate and n-octyl sulfate.
6. A process as in claim 1 wherein said alkyl glycosides are present in the form of solutions or dispersions in such quantities that the active substance content per liter of treating liquor is in the range from 0.1 to 10 g.
7. A process as in claim 1 wherein said alkyl alycosides are present in the amount of 0.25 to 7.5 g. per liter of treating liquor and said alkyl sulfates are present in the amount of 0.1 to 7.25 g. per liter of treating liquor.
8. A process as in claim 1 wherein said alkyl glycosides and said alkyl sulfates are present in a weight ratio of from 80:20 to 20:80.
9. A process as in claim 1 wherein said treatment composition has a pH of from 10 to 14.
10. A surfactant composition for the mercerization of cotton, said composition comprising alkyl glycosides corresponding to general formula I
R1 - O - (G)n (I) in which R1 is a C8.14 alkyl radical, G is a glycose unit and n is a number of 1 to 3, and alkyl sulfates, corresponding to general formula II
R-CH2-0-S03Na (II) in which R is a C6-8 alkyl radical.
11. A composition as in claim 10 wherein R1 is a linear C8-12 alkyl radical.
12. A composition as in claim 10 wherein in said alkyl glycosides corresponding to general formula I, n is a number of 1.1 to 1.4.
13. A composition as in claim 10 wherein G is a glucose unit.
14. A composition as in claim 10 wherein said alkyl sulfates are selected from the group consisting of 2-ethylhexyl sulfate and n-octyl sulfate.
15. A composition as in claim 10 wherein said alkyl glycosides and said alkyl sulfates are present in a weight ratio of from 80:20 to 20:80.
PCT/US1999/011807 1998-06-10 1999-06-08 Alkyl polyglycosides and alkyl sulfates as penetrants in mercerizing baths WO1999064659A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US8879198P true 1998-06-10 1998-06-10
US60/088,791 1998-06-10
US31433299A true 1999-05-19 1999-05-19
US09/314,332 1999-05-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102277736A (en) * 2010-06-11 2011-12-14 沂水祥腾化工有限公司 Highly-alkaliproof mercerizing and infiltrating refining agent

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5753606A (en) * 1993-08-04 1998-05-19 Henkel Kommanditgesellschaft Auf Aktien Low-foaming detergents or cleaning formulations
US5773406A (en) * 1995-07-18 1998-06-30 Henkel Corporation Foaming composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5753606A (en) * 1993-08-04 1998-05-19 Henkel Kommanditgesellschaft Auf Aktien Low-foaming detergents or cleaning formulations
US5773406A (en) * 1995-07-18 1998-06-30 Henkel Corporation Foaming composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102277736A (en) * 2010-06-11 2011-12-14 沂水祥腾化工有限公司 Highly-alkaliproof mercerizing and infiltrating refining agent

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