WO2005090366A1 - Liquid textile-pretreating agent - Google Patents

Liquid textile-pretreating agent Download PDF

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Publication number
WO2005090366A1
WO2005090366A1 PCT/IB2005/000569 IB2005000569W WO2005090366A1 WO 2005090366 A1 WO2005090366 A1 WO 2005090366A1 IB 2005000569 W IB2005000569 W IB 2005000569W WO 2005090366 A1 WO2005090366 A1 WO 2005090366A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
weight
compound
composition
Prior art date
Application number
PCT/IB2005/000569
Other languages
English (en)
French (fr)
Inventor
Manfred Jungen
Original Assignee
Clariant International Ltd
Clariant Finance (Bvi) Limited
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 Clariant International Ltd, Clariant Finance (Bvi) Limited filed Critical Clariant International Ltd
Priority to EP05708677A priority Critical patent/EP1737873A1/en
Priority to US10/593,169 priority patent/US20080254695A1/en
Priority to BRPI0508910-7A priority patent/BRPI0508910A/pt
Publication of WO2005090366A1 publication Critical patent/WO2005090366A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/091Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • 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
    • 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
    • D06M13/282Treating 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 phosphorus
    • D06M13/292Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/295Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
    • 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
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer

Definitions

  • the present invention concerns a liquid textile-pretreating agent useful in all continuous and batch pretreatment operations which is based on phosphoric esters of alkoxylated Guerbet alcohols and is very stable to alkali not only in the formulation but also in the liquor.
  • the pretreatment of the natural or synthetic fibre materials constitutes an important basis for the further processing.
  • the various operations such as desizing, scouring, bleaching or mercerizing employ a wide range of textile chemicals, examples being surfactants, dispersants, emulsif ⁇ ers, bleaches, foam suppressants or defoamers.
  • these auxiliaries as they are known have to meet is high stability to alkali, especially in the alkaline scouring of woven cotton fabric. There is accordingly a constant need for new active compounds having a suitable performance profile.
  • n is from 1 to 3
  • x is from 4 to 12
  • R is a radical of the formula (II)
  • the present compounds are highly stable surfactants which can be present as a highly concentrated, for example 60% solution in water without any need for additives. This combines with good wettability and low foam-forming tendency into a unique performance profile. Especially the extremely high stability to alkali not only in the formulation but also in the liquor predestines these compounds for the alkaline scour, but use as a dispersant, as an emulsif ⁇ er or as a defoamer component is also possible.
  • n is 2 or 3
  • s is from 0 to 4
  • the sum total of (r + s) is from 5 to 7.
  • the index m is an average value, and a particularly preferred value for m is from 1.2 to 1.3.
  • the present compounds are prepared by alkoxylation of appropriate Guerbet alcohols as described in WO 03/091192 Al and subsequent phosphation, preferably with phosphorus pentoxide.
  • the alkylene oxide units of the Guerbet alcohols used are mostly ethylene oxide or propylene oxide units, but mainly ethylene oxide units combined with low fractions of propylene oxide or else only ethylene oxide units.
  • Phosphation is effected by portionwise addition of the phosphating agent at 90 to 120°C during 4 to 24 hours in the absence of air.
  • the present compounds can be used as such or in the form of an aqueous composition for pretreating textiles.
  • the present invention thus further provides a composition comprising an aqueous solution of one or more compounds of the formula (I) and also further auxiliaries.
  • the aqueous composition comprises 40% to 70% by weight of compound (I), although about 2% to 4% by weight can also be present in the form of the sodium salts.
  • the composition may further comprise 0.1% to 3.5% by weight of further auxiliary materials, examples being surfactants, biocides, defoamers or foam suppressants.
  • composition according to the invention is obtainable by simply mixing its constituents.
  • a preferred use of compounds of the formula (I) or of the abovementioned aqueous composition is the pretreatment of textiles in continuous or batch operations under alkaline conditions.
  • Alkali stability What is tested is the alkali stability of 5 g/1 of surfactant, with 100 ml of liquor being made up in each case. The test takes place at room temperature 20 to 25°C. The required amount of aqueous sodium hydroxide solution is weighed into a glass beaker and made up to 95 ml with demineralized water. 5 ml of a 10% surfactant solution are added to the alkali batches with stirring. The glass beakers are left to stand at room temperature for 24 hours without stirring.
  • a 1000 ml graduated cylinder 60 mm in internal diameter and 430 mm in internal height is used.
  • the test liquid is allowed to pour out from a 2 1 separating funnel through a capillary 70 mm in length and 2 mm in internal diameter from a height of 600 mm, measured from the outlet of the capillary above the floor of the cylinder.
  • 500 ml of the solution to be tested are filled into the separating funnel and allowed to flow out into the graduated cylinder through the capillary-controlled efflux rate of about 0.17 1/min.
  • a stopwatch is started and the entire volume (foam volume plus solution volume) is read off the cylinder scale. The reading is repeated after one minute.
  • the alkaline foam performance is tested using a surfactant concentration of 2 g/1 in 2° Be NaOH solution in demineralized water, with 2° Be NaOH being equivalent to 12 g/1 of NaOH solid or 30 ml/1 of NaOH 36° Be.
  • the test temperature is 20 to 25°C.
  • This test method determines the number of seconds a fabric sample takes to sink to the bottom of a glass beaker 1 1 in content, 14 cm in height and 10 cm in diameter in a surfactant solution.
  • the fabric sample used is a cotton test cloth, from EMPA Testmaterialien AG of St. Gallen, Switzerland. Circularly round discs 3.5 cm in diameter are die cut out of this cloth and dipped with a special holder into the surfactant solution. The wetting action is tested in 2° Be NaOH at

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/IB2005/000569 2004-03-17 2005-03-02 Liquid textile-pretreating agent WO2005090366A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05708677A EP1737873A1 (en) 2004-03-17 2005-03-02 Liquid textile-pretreating agent
US10/593,169 US20080254695A1 (en) 2004-03-17 2005-03-02 Liquid Textile-Pretreating Agent
BRPI0508910-7A BRPI0508910A (pt) 2004-03-17 2005-03-02 agente para pré-tratamento de têxteis lìquido

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP04006338 2004-03-17
EP04006338.0 2004-03-17

Publications (1)

Publication Number Publication Date
WO2005090366A1 true WO2005090366A1 (en) 2005-09-29

Family

ID=34924502

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2005/000569 WO2005090366A1 (en) 2004-03-17 2005-03-02 Liquid textile-pretreating agent

Country Status (8)

Country Link
US (1) US20080254695A1 (forum.php)
EP (1) EP1737873A1 (forum.php)
KR (1) KR20070005627A (forum.php)
CN (1) CN1930177A (forum.php)
BR (1) BRPI0508910A (forum.php)
IN (1) IN2006CH03368A (forum.php)
MX (1) MXPA06010103A (forum.php)
WO (1) WO2005090366A1 (forum.php)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008012242A1 (de) 2006-07-24 2008-01-31 Basf Se Zusammensetzung zur verbesserten schaumbildung bei der gewinnung von erdöl- oder erdgas
WO2009015857A3 (de) * 2007-08-02 2009-08-20 Clariant Int Ltd Wässrige zusammensetzungen enthaltend alkoxylierte phosphorsäuretriester
CN102869746A (zh) * 2010-04-23 2013-01-09 巴斯夫欧洲公司 使用基于含C32 Guerbet、C34 Guerbet、C36 Guerbet烷基烷氧基化物的混合物的表面活性剂开采矿物油的方法
US8389756B2 (en) 2007-08-02 2013-03-05 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
US8686033B2 (en) 2007-08-02 2014-04-01 Clariant Finance (Bvi) Limited Phosphoric acid esters containing phosphorus atoms bridged by diol units

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116143828A (zh) * 2023-04-23 2023-05-23 四川科宏达集团有限责任公司 一种高双酯含量磷酸酯表面活性剂的合成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05140174A (ja) * 1991-11-20 1993-06-08 Sakai Chem Ind Co Ltd りん酸トリエステルの製造方法
WO2002008164A1 (de) * 2000-07-21 2002-01-31 Basf Aktiengesellschaft Sekundäre c10-c18-tensidalkohole
DE20303420U1 (de) * 2003-03-03 2003-09-25 Sasol Germany GmbH, 22297 Hamburg Alkoholmischungen und deren Derivate
WO2003091192A1 (de) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10 -alkanolalkoxylat-gemische und ihre verwendung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4453946A (en) * 1981-04-29 1984-06-12 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing synthetic fibre material

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05140174A (ja) * 1991-11-20 1993-06-08 Sakai Chem Ind Co Ltd りん酸トリエステルの製造方法
WO2002008164A1 (de) * 2000-07-21 2002-01-31 Basf Aktiengesellschaft Sekundäre c10-c18-tensidalkohole
WO2003091192A1 (de) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10 -alkanolalkoxylat-gemische und ihre verwendung
DE20303420U1 (de) * 2003-03-03 2003-09-25 Sasol Germany GmbH, 22297 Hamburg Alkoholmischungen und deren Derivate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CARIES RESEARCH , 25(1), 51-7 CODEN: CAREBK; ISSN: 0008-6568, 1991, XP009034124 *
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1994, WACHI, TOSHIO ET AL: "Preparation of phosphate triesters", XP002289140, retrieved from STN Database accession no. 1994:54693 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008012242A1 (de) 2006-07-24 2008-01-31 Basf Se Zusammensetzung zur verbesserten schaumbildung bei der gewinnung von erdöl- oder erdgas
US7842650B2 (en) 2006-07-24 2010-11-30 Basf Aktiengesellschaft Mixture for improved foaming in the extraction of petroleum or natural gas
EA018168B1 (ru) * 2006-07-24 2013-06-28 Басф Се Применение состава для образования пены из водных жидкостей, способ добычи нефти и/или природного газа, способ третичной добычи нефти и способ бурения с применением вспениваемого промывочного бурового раствора
WO2009015857A3 (de) * 2007-08-02 2009-08-20 Clariant Int Ltd Wässrige zusammensetzungen enthaltend alkoxylierte phosphorsäuretriester
US8389756B2 (en) 2007-08-02 2013-03-05 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
US8686033B2 (en) 2007-08-02 2014-04-01 Clariant Finance (Bvi) Limited Phosphoric acid esters containing phosphorus atoms bridged by diol units
US8841475B2 (en) 2007-08-02 2014-09-23 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
CN102869746A (zh) * 2010-04-23 2013-01-09 巴斯夫欧洲公司 使用基于含C32 Guerbet、C34 Guerbet、C36 Guerbet烷基烷氧基化物的混合物的表面活性剂开采矿物油的方法

Also Published As

Publication number Publication date
EP1737873A1 (en) 2007-01-03
BRPI0508910A (pt) 2007-08-14
US20080254695A1 (en) 2008-10-16
MXPA06010103A (es) 2006-11-01
KR20070005627A (ko) 2007-01-10
CN1930177A (zh) 2007-03-14
IN2006CH03368A (forum.php) 2007-06-22

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