US20090031504A1 - Method for Chemically Cleaning Textile Material - Google Patents

Method for Chemically Cleaning Textile Material Download PDF

Info

Publication number
US20090031504A1
US20090031504A1 US11/886,541 US88654106A US2009031504A1 US 20090031504 A1 US20090031504 A1 US 20090031504A1 US 88654106 A US88654106 A US 88654106A US 2009031504 A1 US2009031504 A1 US 2009031504A1
Authority
US
United States
Prior art keywords
alkyl
formula
cleaning
process according
iso
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US11/886,541
Other languages
English (en)
Inventor
Frank-Peter Lang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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 Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Assigned to CLARIANT PRODUKTE (DEUTSCHLAND) GMBH reassignment CLARIANT PRODUKTE (DEUTSCHLAND) GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LANG, FRANK-PETER
Publication of US20090031504A1 publication Critical patent/US20090031504A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents

Definitions

  • Halogenated hydrocarbons are still being used as dry-cleaning medium. They include the hydrochlorocarbons trichloroethene, 1,1,1-trichloroethane and dichloromethane which are no longer permissible in Germany for example. Similarly, the chlorofluorocarbons (CFCs), which used to be widely used in dry cleaning, are no longer permitted for this application in many countries.
  • CFCs chlorofluorocarbons
  • Tetrachloroethene perchloroethylene, perchlorethylene, perc, PER.
  • Tetrachloroethene is a volatile chlorinated hydrocarbon which, by virtue of its fat-dissolving ability, has come to be widely used in industry, including dry cleaning, as a solvent/cleaner.
  • PER PER are in particular its potential carcinogenic effect on humans; its high volatility; its ready solubility in fat-containing foods; and its strongly water-endangering properties.
  • PER is classified as dangerous in the EU's Black List and Germany's Haz Chem regulations.
  • Dry cleaning solvents pose dangers if allowed to pass into the environment.
  • Potential sources of emissions are the cleaning machine, the drying air, the contact water, the distillation sludge, the textile material if inadequately dried and/or due to solvent retention, as well as accidents.
  • Halogen-free hydrocarbon solvents have now been used for some time as technical alternatives to the banned CFCs as well as to the widely used PER. Originally, HCS solvents were only considered as a replacement for CFCs with regard to the cleaning of particularly sensitive textiles.
  • the HCS solvents are straight-chain aliphatics or mixtures of straight-chain, branched and cyclic aliphatics having 10 to 14 carbon atoms. Their higher boiling range from about 180 to 210° C. makes them distinctive from the petroleum fractions formerly likewise used in dry cleaning, or from perchloroethylene which has a boiling point of only 121° C. HCS solvents are widely used in dry cleaning in the US and Japan.
  • one disadvantage with the use of HCS is that, as a consequence of the low vapor pressures, the drying temperatures have to be raised and/or the drying times distinctly extended. This imposes a distinctly greater thermal and mechanical stress on sensitive textiles, which shortens their useful consumer lives.
  • the PER cleaning process consists of three stages:
  • the cleaning with HCS in principle involves the same stages as the PER cleaning process.
  • the cleaning techniques on offer from various producers differ by separation of cleaning and drying (reloading technique), cleaning and drying being integrated in one machine (closed circuit) and also by inertization during cleaning and drying (nitrogen, combination of fresh air and circulating air or vacuum).
  • organic solvents contemplated as an alternative to perchloroethylene and/or to the hydrocarbon solvents Good cleaning power in general and good ability to detach water-soluble or water-swellable soil and pigmentary soil, if appropriate through water-surfactant combinations (cleaning boosters); very good dissolving capacity for fats and oils; good dispersing capacity and sufficient dispersion stability for pigmentary soil to avoid graying; very little if any influencing of fibers, dyeings and finishes, i.e., only limited swelling of fibers, no adverse influence on the felting shrinkage of wool, negligible changes to the thermo-mechanical properties of fibers, no detachment of dyes, finishes, hotmelt adhesives, etc.
  • the present invention has for its object to provide organic solvents which achieve the aforementioned dry cleaning requirements better than prior art solvents and which possess a better toxicological and ecological profile.
  • the present invention accordingly provides for the use of compounds of the formula (1) as an organic cleaning agent and solvent in the dry cleaning of textiles
  • R 1 , R 2 , R 3 and R 4 identically or independently are C 1 to C 13 -n- and/or iso-alkyl, C 5 - or C 6 -cycloalkyl, phenyl-C 1 -C 2 -alkyl, C 1 -C 9 -alkylphenyl or phenyl and a is an integer from 0 to 2.
  • R 1 , R 2 , R 3 and R 4 identically or independently are C 1 to C 8 -n- and/or iso-alkyl, cyclohexyl, benzyl or phenyl and a is 0 or 1.
  • R 1 , R 2 , R 3 and R 4 identically or independently are C 1 to C 3 -n- and/or iso-alkyl and a is 0.
  • R 1 to R 4 radicals are for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, tert-amyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, cyclohexyl, octyl, decyl, isotridecyl, phenyl, benzyl, phenylethyl, nonylphenyl.
  • the compounds of the general formula (1) are acetals.
  • Acetals are generally obtained by reaction of aldehydes with 2 mol of an alcohol per carbonyl group in the presence of catalysts, such as dry hydrogen chloride for example.
  • Dialdehydes have to be used to synthesize compounds of the formula (1).
  • Preferred dialdehydes for synthesizing compounds of the formula (1) are glyoxal, malonaldehyde (1,3-propanedial, 1,3-propanedialdehyde), 1,4-butanedial and terephthalaldehyde.
  • a particularly preferred compound for the purpose described is tetramethoxyethane (2) from Clariant
  • Compounds of the formula (1) can be utilized at various stages of the dry cleaning process, both in the industrial and institutional sector and in domestic dry cleaning. These include in particular the use as a dissolving and cleaning agent in the basic cleaning operation.
  • the compounds of the formula (1) can wholly replace the cleaning agents perchloroethylene, hydrocarbons and also other solvents.
  • Process modifications or modifications to the cleaning machines may be necessary, depending on the physical-chemical properties of specific compounds of the formula (1). For instance, different boiling points, due to different R 1 to R 4 radicals and/or different a values, may necessitate different drying temperatures and, for example, variations in the distillation conditions to recover the solvent (pressure, temperature).
  • Flashpoints other than those of the HCS solvents used may also necessitate safety-engineering modifications, for example through the type of inertization (residual oxygen contents).
  • the organic R radicals in the solvents of the formula 1 can be varied to control the dissolving power for apolar substances (other solvents, fats, oils) and also for polar substances and solvents (including water).
  • HCS machines utilize higher g factors than PER machines.
  • solvents of the formula (1) include, for example, cleaning time, liquor ratio, reversing rhythm, load level, identity and amount of cleaning booster used, application of a whirlbath through injection of an air-solvent mixture for gentle cleaning of sensitive textiles.
  • Dry cleaning processes are further distinguished between the one bath process and the two bath process.
  • Standard work is generally cleaned in the two bath process by employing a short liquor ratio in the first bath and a longer liquor ratio in the second bath.
  • the first bath serves to detach the main soil.
  • Solvents of the formula (1) can be used in the one bath process and in the two bath process.
  • compounds of the formula (1) can also be utilized in spotting agents, in cleaning activators or in cleaning boosters.
  • Spotting agents are used for spot removal from textiles in industrial textile cleaning. The following groups of spotting agents are distinguished:
  • Cleaning activators are used to remove spots and may also comprise odor absorbents for example. They are applied in the pretreatment bath and, being soil dissolvers, obviate any brushing.
  • Cleaning boosters being added to the organic solvent used as cleaning medium, are intended to enhance the cleaning performance and, more particularly, also to effect the detachment of water-soluble or water-swellable soils which are only sparingly soluble, if at all, in the organic solvent.
  • water-soluble compounds include gritting salt (NaCl in high purity or else in mixture with CaCl 2 or MgCl 2 sols) as used in winter to deice sidewalks and streets. They shall further remove insoluble, pigmentary soil and exhibit a pigment-dispersing capacity and so inhibit the redeposition of detached particulate soil. They further serve to avoid pilling and to improve fabric hand.
  • Cleaning boosters typically comprise surfactants (in particular anionic, nonionic, amphoteric surfactants or else cationic surfactants), solvents, antistats, softeners or hand-improving additives and, if appropriate, specialty adds such as disinfectants and bleaching agents. Furthermore, the cleaning booster can be used to introduce small amounts of water into the cleaning bath that is emulsified into the organic solvents with the surfactants.
  • the cleaning agent bath i.e., the solvent of the formula (1) used for the basic cleaning operation, the spotting agents, the cleaning activators and the cleaning boosters comprising solvent of the formula (1) may comprise the following further soil release enhancers.
  • Surfactants which may be used in addition to or in the cleaning agents of the formula (1), for example in tetramethoxyethane (2), are:
  • Useful anionic surfactants include sulfates, sulfonates, carboxylates, phosphates and mixtures thereof.
  • Suitable cations are alkali metals, for example sodium or potassium, or alkaline earth metals, for example calcium or magnesium, and also ammonium, substituted ammonium compounds, including mono-, di- or triethanolammonium cations, and mixtures thereof.
  • anionic surfactants are particularly preferred: alkyl ester sulfonates, alkyl sulfates, alkyl ether sulfates, alkylbenzenesulfonates, alkanesulfonates and soaps as described in what follows.
  • Alkyl ester sulfonates include linear esters of C 8 -C 2 2 -carboxylic acids (i.e., fatty acids) which are sulfonated with gaseous SO 3 .
  • Suitable starting materials are natural fats, such as tallow, coco oil and palm oil for example. But the carboxylic acids may also be synthetic in nature.
  • Preferred alkyl ester sulfonates are compounds of the formula
  • R 1 is a C 8 -C 20 -hydrocarbyl radical, preferably alkyl
  • R is a C 1 -C 6 -hydrocarbyl radical, preferably alkyl
  • M represents a cation which forms a water-soluble salt with the alkyl ester sulfonate. Suitable cations are sodium, potassium, lithium or ammonium cations, such as monoethanolamine, diethanolamine and triethanolamine.
  • R 1 is C 10 -C 16 -alkyl and R is methyl, ethyl or isopropyl. Particular preference is given to methyl ester sulfonates wherein R 1 is C 10 -C 16 -alkyl.
  • Alkyl sulfates are salts or acids of the formula ROSO 3 M, where R is a C 10 -C 24 -hydrocarbyl radical, preferably an alkyl or hydroxyalkyl radical having a C 10 -C 20 -alkyl component, more preferably a C 12 -C 18 alkyl or hydroxyalkyl radical.
  • M is hydrogen or a cation, for example an alkali metal cation (examples being sodium, potassium, lithium) or ammonium or substituted ammonium, for example methyl-, dimethyl- and trimethylammonium cations and quaternary ammonium cations such as tetramethylammonium and dimethylpiperidinium cations and quaternary ammonium cations derived from alkylamines, such as ethylamine, diethylamine, triethylamine and mixtures thereof.
  • alkali metal cation examples being sodium, potassium, lithium
  • ammonium or substituted ammonium for example methyl-, dimethyl- and trimethylammonium cations and quaternary ammonium cations such as tetramethylammonium and dimethylpiperidinium cations and quaternary ammonium cations derived from alkylamines, such as ethylamine, diethylamine, triethyl
  • Alkyl ether sulfates are salts or acids of the formula RO(A) m SO 3 M, where R is an unsubstituted C 10 -C 24 -alkyl or hydroxyalkyl radical, preferably a C 12 -C 20 alkyl or hydroxyalkyl radical, more preferably a C 12 -C 18 -alkyl or hydroxyalkyl radical.
  • A is an ethoxy or propoxy unit
  • m is a number greater than 0, preferably between about 0.5 and about 6, and more preferably between about 0.5 and about 3
  • M is a hydrogen atom or a cation, for example sodium, potassium, lithium, calcium, magnesium, ammonium or a substituted ammonium cation.
  • substituted ammonium cations are methyl-, dimethyl- and trimethylammonium and quaternary ammonium cations such as tetramethylammonium and dimethylpiperidinium cations and also those derived from alkylamines, such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • Examples which may be mentioned are C 12 - to C 18 -fatty alcohol ether sulfates wherein the EO content is 1, 2, 2.5, 3 or 4 mol per mole of the fatty alcohol ether sulfate and wherein M is sodium or potassium.
  • the alkyl group in secondary alkanesulfonates may be either saturated or unsaturated, branched or linear and optionally hydroxy substituted.
  • the sulfo group may be situated on any position of the carbon chain, although the primary methyl groups at either end of the chain do not possess any sulfonate groups.
  • the preferred secondary alkanesulfonates comprise linear alkyl chains having about 9 to 25 carbon atoms, preferably about 10 to about 20 carbon atoms and more preferably about 13 to 17 carbon atoms.
  • the cation is for example sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium, or mixtures thereof. Sodium is the preferred cation.
  • primary alkanesulfonates can likewise be used in the washing compositions of the present invention.
  • the preferred alkyl chains and cations are as for the secondary alkanesulfonates.
  • Useful anionic surfactants further include alkenyl- or alkylbenzenesulfonates.
  • the alkenyl or alkyl group may be branched or linear and optionally hydroxyl substituted.
  • the preferred alkylbenzenesulfonates comprise linear alkyl chains having about 9 to 25 carbon atoms and preferably from about 10 to about 13 carbon atoms; the cation is sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
  • Magnesium is the preferred cation for mild surfactant systems, whereas sodium is the preferred cation for standard applications. The same applies to alkenylbenzenesulfonates.
  • anionic surfactants also comprehends olefinsulfonates, which are obtained by sulfonation of C 8 -C 24 -olefins and preferably C 14 -C 16 - ⁇ -olefins with sulfur trioxide and subsequent neutralization. Their method of production is such that these olefinsulfonates may comprise minor amounts of hydroxyalkanesulfonates and alkanedisulfonates.
  • Preferred anionic surfactants further include carboxylates, examples being fatty acid soaps and comparable surfactants.
  • the soaps may be saturated or unsaturated and may comprise various substituents, such as hydroxyl groups or ⁇ -sulfonate groups. Preference is given to linear saturated or unsaturated hydrocarbyl radicals as a hydrophobic moiety having about 6 about 30 and preferably about 10 to about 18 carbon atoms.
  • Useful anionic surfactants further include salts of acylamino carboxylic acids, acyl sarcosinates formed by reaction of fatty acid chlorides with sodium sarcosinate in an alkaline medium; fatty acid-protein condensation products obtained by reaction of fatty acid chlorides with oligopeptides; salts of alkylsulfamido carboxylic acids; salts of alkyl and alkylaryl ether carboxylic acids; sulfonated polycarboxylic acids; alkyl and alkenyl glycerol sulfates such as oleyl glycerol sulfates, alkylphenol ether sulfates, alkyl phosphates, alkyl ether phosphates, isethionates, such as acyl isethionates, N-acyltaurides, alkyl succinates, sulfosuccinates, monoesters of sulfosuccinates (particularly saturated
  • the alkyl chain of the aliphatic alcohols may be linear or branched, primary or secondary, and comprises in general from about 8 to about 22 carbon atoms. Particular preference is given to the condensation products of C 10 - to C 20 -alcohols with about 2 to about 18 mol of ethylene oxide per mole of alcohol.
  • the alkyl chain may be saturated or else unsaturated.
  • the alcohol ethoxylates may comprise the ethylene oxide in a narrow homolog distribution (“narrow range ethoxylates”) or in a broad homolog distribution (“broad range ethoxylates”). This class of product includes for example the Genapol® brands (from Clariant).
  • Condensation products of ethylene oxide with a hydrophobic base formed by condensation of propylene oxide with propylene glycol.
  • the hydrophobic part of these compounds preferably has a molecular weight between about 1500 and about 1800.
  • the addition of ethylene oxide onto this hydrophobic part leads to improved solubility in water.
  • the product is liquid up to a polyoxyethylene content of about 50% of the overall weight of the condensation product, which corresponds to a condensation with up to about 40 mol of ethylene oxide.
  • Commercially available examples of this class of products are the ®Genapol PF brands (from Clariant).
  • the hydrophobic unit of these compounds consists of the reaction product of ethylenediamine with excess propylene oxide and generally has a molecular weight in the range of about 2500 to 3000. Ethylene oxide is added onto this hydrophobic unit up to a level of about 40% to about 80% by weight of polyoxyethylene and a molecular weight of about 5000 to 11 000.
  • Commercially available examples of this class of compounds are the ®Tetronic brands from BASF and the ®Genapol PN brands from Clariant GmbH.
  • nonionic compounds comprises water-soluble amine oxides, water-soluble phosphine oxides and water-soluble sulfoxides, each having an alkyl radical of about 10 to about 18 carbon atoms.
  • Semipolar nonionic surfactants further include amine oxides of the formula
  • R is an alkyl, hydroxyalkyl or alkylphenol group having a chain length of about 8 to about 22 carbon atoms
  • R 2 is an alkylene or hydroxyalkylene group having about 2 to 3 carbon atoms or mixtures thereof
  • every R 1 radical is an alkyl or hydroxyalkyl group having about 1 to about 3 carbon atoms or a polyethylene oxide group having about 1 to about 3 ethylene oxide units and x is from 0 to about 10.
  • the R 1 groups may be joined together via an oxygen or nitrogen atom and thus form a ring.
  • Amine oxides of this kind are particularly C 10 -C 18 -alkyldimethylamine oxides and C 8 -C 12 -alkoxyethyldihydroxyethylamine oxides.
  • Fatty acid amides have the formula
  • R is an alkyl group having about 7 to about 21 and preferably about 9 to about 17 carbon atoms and every R 1 radical is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl or (C 2 H4O) x H, where x varies from about 1 to about 3.
  • C 8 -C 20 amides, monoethanolamides, diethanolamides and isopropanolamides are preferred.
  • Useful nonionic surfactants further include alkyl and alkenyl oligoglycosides and also fatty acid polyglycol esters or fatty amine polyglycol esters each having 8 to 20 and preferably 12 to 18 carbon atoms in the fatty alkyl moiety, alkoxylated triglycamides, mixed ethers or mixed formyls, alkyl oligoglycosides, alkenyl oligoglycosides, fatty acid N-alkyl glucamides, phosphine oxides, dialkyl sulfoxides and protein hydrolyzates.
  • Polyethylene, polypropylene and polybutylene oxide condensates of alkylphenols.
  • These compounds comprise the condensation products of alkylphenols having a C 6 - to C 20 -alkyl group, which may be either linear or branched, with alkene oxides. Preference is given to compounds having about 5 to about 25 mol of alkene oxide per mole of alkylphenol.
  • Commercially available surfactants of this type are for example the ®Arkopal N brands (from Clariant). These surfactants are referred to as alkylphenol alkoxylates, an example being alkylphenol ethoxylates.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkylamide betaines, aminopropionates, aminoglycinates, or amphoteric imidazolinium compounds of the formula
  • R 1 denotes C 8 -C 22 -alkyl or -alkenyl
  • R 2 denotes hydrogen or CH 2 CO 2 M
  • R 3 denotes CH 2 CH 2 OH or CH 2 CH 2 OCH 2 CH 2 CO 2 M
  • R 4 denotes hydrogen, CH 2 CH 2 OH or CH 2 CH 2 COOM
  • Z denotes CO 2 M or CH 2 CO 2 M
  • n denotes 2 or 3, preferably 2
  • M denotes hydrogen or a cation such as alkali metal, alkaline earth metal, ammonium or alkanolammonium.
  • Preferred amphoteric surfactants of this formula are monocarboxylates and dicarboxylates. Examples thereof are cocoamphocarboxypropionate, cocoamido carboxy propionic acid, cocoamphocarboxyglycinate (or else referred to as cocoamphodiacetate) and cocoamphoacetate.
  • Preferred amphoteric surfactants further include alkyl dimethyl betaines (®Genagen LAB/Clariant GmbH) and alkyl dipolyethoxy betaines having an alkyl radical of about 8 to about 22 carbon atoms, which may be linear or branched, preferably 8 to 18 carbon atoms and more preferably having about 12 to about 18 carbon atoms.
  • alkyl dimethyl betaines ®Genagen LAB/Clariant GmbH
  • alkyl dipolyethoxy betaines having an alkyl radical of about 8 to about 22 carbon atoms, which may be linear or branched, preferably 8 to 18 carbon atoms and more preferably having about 12 to about 18 carbon atoms.
  • Useful cationic surfactants include substituted or unsubstituted straight-chain or branched quaternary ammonium salts of the type R 1 N(CH 3 ) 3 + X ⁇ , R 1 R 2 N(CH 3 ) 2 + X ⁇ , R 1 R 2 R 3 N(CH 3 ) + X ⁇ or R 1 R 2 R 3 R 4 N + X ⁇ .
  • the R 1 , R 2 , R 3 and R 4 radicals may preferably independently be unsubstituted alkyl having a chain length of between 8 and 24 carbon atoms and especially between 10 and 18 carbon atoms, hydroxyalkyl having about 1 to about 4 carbon atoms, phenyl, C 2 - to C 18 -alkenyl such as, for example, tallow alkyl or oleyl, C 7 - to C 24 -aralkyl, (C 2 H 4 O ) x H, where x is from about 1 to about 3, or else alkyl radicals comprising one or more ester groups, or cyclic quaternary ammonium salts.
  • X is a suitable anion.
  • odor absorbents As well as surfactants, further materials may be present: odor absorbents, deodorants, scents, antistats, microbicides such as bactericides and fungicides, preservatives, solubilizers, fiber regenerants, finishes, emulsifiers, enzymes, impregnants and also water in small amounts.
  • TBE tetramethoxyethane
  • test fabrics used were:
  • test fabrics were each soiled with paraffin oil colored with the fat-soluble dye Sudan Red. The reflectance (whiteness) of the soiled fabrics was measured. The test fabrics were then washed with tetramethoxyethane and the reference solvents at room temperature in a Linitest laboratory washing machine. For each type of fabric the wash included an unstained white fabric of the same type in order that the soil transfer/redeposition may be investigated. After the wash, the test fabrics were dried and assessed as follows.
  • the reflectance (whiteness) of the cleaned fabrics was determined and the difference to the values measured for the soiled fabrics was calculated.
  • the power to remove a vegetable oil stain from various Wäschereiutzs GmbH Krefeld laundry research institute standard test fabrics was investigated.
  • the vegetable oil used was sunflower oil, likewise colored with Sudan Red.
  • the cleaning power of tetramethoxyethane compared with PER and HCS was investigated on various standardized soiled fabrics from the Wäschereiutzs GmbH Krefeld laundry research institute.
  • the following test fabrics were used: cotton-polyester wfk 20C (blend fabric with fat-pigment soiling) and cotton-polyester wfk 20D (blend fabric with synthetic sebum soiling).
  • the test fabrics were washed in a Linitest laboratory washing machine at room temperature.
  • the wash included unsoiled cotton-polyester white fabric wfk 20A in order that the soil transfer from soiled to white test fabrics may be investigated.
  • the stability of textile dyeings was tested on various commercially available colored fabrics.
  • the colored fabrics were:
  • One of the colored swatches and two of the white swatches were removed after 10 min. The second colored swatch and the remaining two white swatches were each washed for another 50 minutes.
  • the color difference dE to the unwashed colored fabrics was determined to quantify the preservation of the color of the colored fabrics. The lower the dE color differences, the less the dyeings are attacked by the cleaning agent.
  • a possible color transfer due to detached dye was quantified by measuring the color different dE of the washed white swatches to the unwashed white fabric. The lower the dE value, the less the white fabrics were stained by the colored fabrics.
  • the dE values are zero both for the preservation of color and for the transfer of color.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US11/886,541 2005-03-15 2006-03-06 Method for Chemically Cleaning Textile Material Abandoned US20090031504A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102005011722A DE102005011722B4 (de) 2005-03-15 2005-03-15 Verfahren zur chemischen Reinigung von Textilmaterial
DE102005011722.8 2005-03-15
PCT/EP2006/002014 WO2006097213A1 (de) 2005-03-15 2006-03-06 Verfahren zur chemischen reinigung von textilmaterial

Publications (1)

Publication Number Publication Date
US20090031504A1 true US20090031504A1 (en) 2009-02-05

Family

ID=36293716

Family Applications (1)

Application Number Title Priority Date Filing Date
US11/886,541 Abandoned US20090031504A1 (en) 2005-03-15 2006-03-06 Method for Chemically Cleaning Textile Material

Country Status (8)

Country Link
US (1) US20090031504A1 (enExample)
EP (1) EP1861543A1 (enExample)
JP (1) JP2008535951A (enExample)
CN (1) CN101151411A (enExample)
CA (1) CA2601177A1 (enExample)
DE (1) DE102005011722B4 (enExample)
RU (1) RU2404315C2 (enExample)
WO (1) WO2006097213A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080194453A1 (en) * 2005-03-15 2008-08-14 Frank-Peter Lang Washing and Cleaning Agents Containing Acetales as Organic Solvents
US9261246B2 (en) 2010-03-11 2016-02-16 Panasonic Intellectual Property Management Co., Ltd. Light-emitting module, light source device, liquid crystal display device, and method of manufacturing light-emitting module
US20170236848A1 (en) * 2010-07-30 2017-08-17 Semiconductor Energy Laboratory Co., Ltd. Semicondcutor device and manufacturing method thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009027206A1 (de) * 2009-06-25 2010-12-30 Chemische Fabrik Kreussler & Co. Gmbh Verwendung von Dietherverbindungen bei der chemischen Reinigung von Textil-, Leder- oder Pelzwaren
CN103103742A (zh) * 2012-12-14 2013-05-15 常熟市琴达针织印染有限公司 一种布料印花工艺
DE102017012021A1 (de) 2017-12-22 2019-06-27 Friedrich-Schiller-Universität Jena Acetalischer Elektrolyt
CN107988728B (zh) * 2017-12-27 2019-11-05 宁波高新区盛文途纺织品有限公司 一种纺织品清理方法

Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US30429A (en) * 1860-10-16 Blind-slat machine
US801157A (en) * 1905-02-11 1905-10-03 Robert R Raymond Camp-table.
US847976A (en) * 1905-09-05 1907-03-19 Frederick C Warren Fruit-jar and can closure.
US1084232A (en) * 1913-06-11 1914-01-13 Herman Reis Manufacture of radiators.
US1184448A (en) * 1916-01-07 1916-05-23 Charles Lowry Device for handling a plurality of train-orders and messages.
US1460052A (en) * 1921-03-07 1923-06-26 Westfield Mfg Company Cycle
US2132898A (en) * 1938-03-25 1938-10-11 Hamel Lionel Attachment for electric razors
US2194405A (en) * 1940-03-19 Process of producing tetba-acetals
US2321094A (en) * 1941-03-18 1943-06-08 Carbide & Carbon Chem Corp Tetraacetals of glyoxal with glycol monoethers and process of making them
US2785947A (en) * 1954-01-08 1957-03-19 Quaker Chemical Products Corp Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom
US4541837A (en) * 1979-12-11 1985-09-17 Aeci Limited Fuels
US4619668A (en) * 1985-09-11 1986-10-28 The United States Of America As Represented By The Secretary Of Agriculture Dyed wrinkle-resistant and durable-press cotton fabrics
US5191127A (en) * 1991-08-13 1993-03-02 Loyola University Of Chicago Glyoxal derivatives and method for making the same
US5269958A (en) * 1993-01-13 1993-12-14 S. C. Johnson & Son, Inc. Self-pressurized aerosol spot dry cleaning compositions
US5766758A (en) * 1996-03-27 1998-06-16 Kuraray Co., Ltd. Fiber of ethylene-vinyl alcohol copolymer and process for production thereof
US6013842A (en) * 1996-12-11 2000-01-11 Basf Aktiengesellschaft Preparation of glyoxal monoacetals
US6054519A (en) * 1996-09-09 2000-04-25 Clariant Gmbh Polyvinyl alcohol compositions
US6177070B1 (en) * 1998-01-05 2001-01-23 Una E. Lynch Deodorant composition
US20010022007A1 (en) * 1997-08-27 2001-09-20 The Procter & Gamble Company Bagless dry cleaning kits and processes for dry cleaning
US20010031716A1 (en) * 2000-02-07 2001-10-18 Grant Gary Alan Detergent compositions
US20020061827A1 (en) * 2000-08-30 2002-05-23 Clariant Gmbh Aqueous liquids comprising a surfactant and an acetal
US20040106274A1 (en) * 2002-11-21 2004-06-03 International Business Machines Corporation Gate structure with independently tailored vertical doping profile
US6749643B2 (en) * 2000-12-26 2004-06-15 Shin-Etsu Chemical Co., Ltd. Method of dry cleaning and dry cleaning solvent therefor
US20040186304A1 (en) * 2003-03-21 2004-09-23 Degussa Ag Process for continuously preparing acetals of alpha, beta-dicarbonyl compounds
US20040226105A1 (en) * 1997-04-04 2004-11-18 Rynex Holdings, Inc. Biodegradable ether dry cleaning solvent
US20070073088A1 (en) * 2003-05-22 2007-03-29 Clariant (France) Process for the separation, by countercurrentwise liquid-liquid extraction, of a glyoxal diacetal from a crude mixture comprising it

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1594232A1 (ru) * 1987-07-20 1990-09-23 Омский технологический институт бытового обслуживания Состав дл удалени гидрофобных загр знений
GB9714707D0 (en) * 1997-07-11 1997-09-17 Johnson & Son Inc S C Compositions suitable for use in aerosol dispensers

Patent Citations (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2194405A (en) * 1940-03-19 Process of producing tetba-acetals
US30429A (en) * 1860-10-16 Blind-slat machine
US801157A (en) * 1905-02-11 1905-10-03 Robert R Raymond Camp-table.
US847976A (en) * 1905-09-05 1907-03-19 Frederick C Warren Fruit-jar and can closure.
US1084232A (en) * 1913-06-11 1914-01-13 Herman Reis Manufacture of radiators.
US1184448A (en) * 1916-01-07 1916-05-23 Charles Lowry Device for handling a plurality of train-orders and messages.
US1460052A (en) * 1921-03-07 1923-06-26 Westfield Mfg Company Cycle
US2132898A (en) * 1938-03-25 1938-10-11 Hamel Lionel Attachment for electric razors
US2321094A (en) * 1941-03-18 1943-06-08 Carbide & Carbon Chem Corp Tetraacetals of glyoxal with glycol monoethers and process of making them
US2785947A (en) * 1954-01-08 1957-03-19 Quaker Chemical Products Corp Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom
US4541837A (en) * 1979-12-11 1985-09-17 Aeci Limited Fuels
US4541835A (en) * 1979-12-11 1985-09-17 Aeci Limited Fuels
US4619668A (en) * 1985-09-11 1986-10-28 The United States Of America As Represented By The Secretary Of Agriculture Dyed wrinkle-resistant and durable-press cotton fabrics
US5191127A (en) * 1991-08-13 1993-03-02 Loyola University Of Chicago Glyoxal derivatives and method for making the same
US5269958A (en) * 1993-01-13 1993-12-14 S. C. Johnson & Son, Inc. Self-pressurized aerosol spot dry cleaning compositions
US5766758A (en) * 1996-03-27 1998-06-16 Kuraray Co., Ltd. Fiber of ethylene-vinyl alcohol copolymer and process for production thereof
US6054519A (en) * 1996-09-09 2000-04-25 Clariant Gmbh Polyvinyl alcohol compositions
US6013842A (en) * 1996-12-11 2000-01-11 Basf Aktiengesellschaft Preparation of glyoxal monoacetals
US20040226105A1 (en) * 1997-04-04 2004-11-18 Rynex Holdings, Inc. Biodegradable ether dry cleaning solvent
US7008458B2 (en) * 1997-04-04 2006-03-07 Hayday William A Biodegradable ether dry cleaning solvent
US20010022007A1 (en) * 1997-08-27 2001-09-20 The Procter & Gamble Company Bagless dry cleaning kits and processes for dry cleaning
US6177070B1 (en) * 1998-01-05 2001-01-23 Una E. Lynch Deodorant composition
US20010031716A1 (en) * 2000-02-07 2001-10-18 Grant Gary Alan Detergent compositions
US20020061827A1 (en) * 2000-08-30 2002-05-23 Clariant Gmbh Aqueous liquids comprising a surfactant and an acetal
US6749643B2 (en) * 2000-12-26 2004-06-15 Shin-Etsu Chemical Co., Ltd. Method of dry cleaning and dry cleaning solvent therefor
US20040106274A1 (en) * 2002-11-21 2004-06-03 International Business Machines Corporation Gate structure with independently tailored vertical doping profile
US20040186304A1 (en) * 2003-03-21 2004-09-23 Degussa Ag Process for continuously preparing acetals of alpha, beta-dicarbonyl compounds
US20070073088A1 (en) * 2003-05-22 2007-03-29 Clariant (France) Process for the separation, by countercurrentwise liquid-liquid extraction, of a glyoxal diacetal from a crude mixture comprising it

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080194453A1 (en) * 2005-03-15 2008-08-14 Frank-Peter Lang Washing and Cleaning Agents Containing Acetales as Organic Solvents
US7632793B2 (en) * 2005-03-15 2009-12-15 Clariant Produkte (Deutschland) Gmbh Washing and cleaning agents containing acetals as organic solvents
US9261246B2 (en) 2010-03-11 2016-02-16 Panasonic Intellectual Property Management Co., Ltd. Light-emitting module, light source device, liquid crystal display device, and method of manufacturing light-emitting module
US20170236848A1 (en) * 2010-07-30 2017-08-17 Semiconductor Energy Laboratory Co., Ltd. Semicondcutor device and manufacturing method thereof

Also Published As

Publication number Publication date
JP2008535951A (ja) 2008-09-04
RU2404315C2 (ru) 2010-11-20
WO2006097213A1 (de) 2006-09-21
DE102005011722A1 (de) 2006-09-21
RU2007137825A (ru) 2009-04-20
EP1861543A1 (de) 2007-12-05
CN101151411A (zh) 2008-03-26
CA2601177A1 (en) 2006-09-21
DE102005011722B4 (de) 2010-04-08

Similar Documents

Publication Publication Date Title
AU2001275510B2 (en) Biodegradable ether dry cleaning solvent
US5888250A (en) Biodegradable dry cleaning solvent
AU736088B2 (en) Dry cleaning methods and compositions
US6172031B1 (en) Compositions and methods for use in cleaning textiles
IL140832A (en) Method for dry and solvent cleaning
US20090031504A1 (en) Method for Chemically Cleaning Textile Material
JPH0551598A (ja) ドライクリーニング溶剤
AU2005205524A1 (en) Biodegradable ether dry cleaning solvent
RU2543715C2 (ru) Применение простых диэфиров при химической чистке текстильных, кожаных или меховых изделий
JP2005530884A (ja) 布地の洗浄
US20100040785A1 (en) Method For Dry-Cleaning Leather
EP0042779B1 (fr) Procédé pour diminuer la redéposition des salissures au cours du nettoyage à sec et composition pour sa mise en oeuvre
US3772205A (en) Cleaning agent for textiles
CA2474357C (en) A method of dry cleaning articles using densified carbon dioxide
JP2007504371A (ja) ジプロピレングリコールｎ−プロピルエーテルを使用するドライクリーニング方法
CA2577566A1 (en) Drycleaning method using dipropylene glycol dimethyl ether
CA2522643C (en) Dry cleaning textiles
EP1343931B1 (en) Fabric cleaning system
WO1994001522A1 (en) 1,1-dichloro-1-fluoroethane based dry cleaning composition

Legal Events

Date Code Title Description
AS Assignment

Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:LANG, FRANK-PETER;REEL/FRAME:019883/0466

Effective date: 20070903

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE