US3821023A - Crease resistant finish for textiles having improved soil repellent properties - Google Patents

Crease resistant finish for textiles having improved soil repellent properties Download PDF

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US3821023A
US3821023A US00210116A US21011671A US3821023A US 3821023 A US3821023 A US 3821023A US 00210116 A US00210116 A US 00210116A US 21011671 A US21011671 A US 21011671A US 3821023 A US3821023 A US 3821023A
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acid
compound
resin
radical
methylol
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W Amati
R Hochreuter
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Sandoz AG
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Sandoz AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating 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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating 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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid

Definitions

  • ABSTRACT Compounds for the soil repellent finishing of textiles of the general formula wherein R stands for a p-valent radical of an organic compound which has one to 40 carbon atoms and contains at least one active hydrogen atom,
  • R for hydrogen or for a saturated orunsaturated alkyl or an aromatic radical or an aliphatic carboxylic acid radical which has one to 30 .carbon atoms or for the radical of an inorganic 14 Claims, No Drawings CREASE RESISTANT FINISH FOR TEXTILES HAVING IMPROVED SOIL REPELLENT PROPERTIES and where the molecule has a minimum molecular weight of 100 and bears at least one free acid group.
  • the p-valent radical R is the radical of a compound
  • textiles of the various synthetic and cel- R(H), having at least p active hydrogen atoms. which lulosic fibres, alone or in blends, in particular polyester fibre textiles, which have been finished with N- methylol resins, show enhanced power of soil retention whichmeans that they become heavily soiled in use and when washed cannot readilybe cleared of the impurities.
  • textiles of these fibres are finished with hydrophilic compounds.
  • the products which have found acceptance in the textile industry for this purpose include the polyacrylic acid derivatives disclosedin US. Pat. No. 3,377,249, the polyoxyalkylene glycol terephthalic acid copolymers disclosed in French Pat. No. 1,502,969, the monostearic acid polyglycol esters disclosed in British Pat. No. 738,379 and the adducts of ethylene oxide and propylene oxide on alkyl phenols which are described in the published Swiss Pat. application 6149/68 and the published German Pat. application 1,914,389.
  • the polyacrylic acid derivatives impart a harsh, stiff handle to the finished fabric
  • the polyoxyalkylene glycolterephthalic acid copolymers are not applicable to cotton, while the monostearic acid-polyglycol esters, and the ethylene oxide and propylene oxide adducts on alkyl phenols leave the fabric with unsatisfactory wash resistance and impair the fastness properties .of dyed goods, especially if they have been dyed with disperse dyes.
  • This invention therefore relates to the use for the soil repellent finishing of textile fibres, yarns and fabrics of compounds agreeing with the general formula where R stands for a p-valent radical of anorganic compound which has oneto 40 carbon atoms and contains at least one active hydrogen atom,
  • R for hydrogen or for a saturated or unsaturated alkyl or an aromatic radical or an aliphatic carboxylic acid radical which has 1 to 30 carbon atoms or for the radical of an inorganic acid which may be esterified,
  • n for zero or a value from 1 to 100
  • the p-valent radical R consists of an optionally further unsubstituted or substituted alkyl, alkenyl or aromatic radical having one to 40 carbon atoms, these atoms bearing at least one of the aforenamed alcoholic, thioalcoholic, acid or amidated groups which is capable of binding an active hydrogen atom.
  • the preferred unsubstituted or substituted alkyl radicals have one to 40 carbon atoms, special preference being given to aliphatic hydrocarbon radicals with two to 22 carbon atoms which may bear aromatic ring systems as substituents.
  • the substituents on the alkyl radicals are preferably phenyl, naphthyl, diphenyl, diphenylether, diphe nylsulphide or diphenylmethane radicals, which may be further substituted by hydroxyl, lower alkyl or an acid radical.
  • the v disclosed compounds are further characterized by the fact that the value of it may vary within wide limits.
  • Compounds with high n values are of major interest for the finishing of white goods.
  • the introduction of several free acid groups, in particular carboxymethyl groups or phosphorus or sulphonic acid groups which may if desired by esterified has a favourable effect.
  • the compounds of this invention contain at least one but preferably not more than five free acid groups, which may be present as alkali-metal or ammonium salts. Optimally one to three acid groups are present.
  • the compound of formula I should have a minimum molecular weight of 100.
  • the compounds employed in accordance with this invention can be produced by known methods or in analogy with known methods, with the necessary condition that one free acid group remains in the reaction product or is introduced into it. A number of these methods are outlined below.
  • the carboxylic acids may be saturated or unsaturated, aliphatic or aromatic monoor p0ly-carboxylic acids, preferably polycarboxylic and/or sulphocarboxylic acids, or their derivatives such as the anhydrides, esters or halides, notably the chlorides or bromides.
  • saturated dibasic acids may be named oxalic, malonic, succinic, adipic and azelaic acid; of the unsaturated dibasic acids maleic and fumaric acid; of the hydroxyl-substituted acids maleic, tartaric and citric acid; of the aromatic dicarboxylic acids phthalic, isophthalic and terephthalic acid; of the aromatic tricarboxylic acids trimellitic, hemimellitic and trimesic acid; of the aromatic tetracarboxylic acids mellophanic and pyromellitic acid; and as hexacarboxylic acid mellitic acid.
  • diphenyldicarboxylic acid aliphatic and aromatic sulphocarboxylic acids, sulphuric acid esters such as sulphosuccinic and sulphotricarballylic acid, the sulphation products of fatty acids such as oleic acid, sulphuric acid esters of monoand di-oxystearic acid, sulphobenzoic, sulphophenylacetic, sulphophenoxyacetic and sulphophthalic acids, sulphophthalic acid amides, naphthalenesulphonic and naphthalenepolysulphonic acids and their alkyl derivatives in which the alkyl chains bear one to 24 carbon atoms, alkanc and alkene acids having preferably eight to 30 carbon atoms, for example caproic, caprylic, cypric, lauric, myristic, stearic, arachic, be-
  • henic, oleic and ricinoleic acid the corresponding sulphonic acids, the sulphates of the corresponding alcohols, aromatic monocarboxylic and monosulphonic acids such as phenolcarboxylic acids (salicylic acid), phenolsulphonic acids. their condensation products with formaldehyde, mono-, diand tri-alkylphenolsulphonic acids, alkylphenylphosphoric acid esters such as amyl and diamyl derivatives, nonyl derivatives, dodecyl and octadecyl derivatives.
  • saturated or unsaturated hydroxy compounds having preferably six to 30 carbon atoms are suitable, examples being octyl, lauryl, stearyl, behenyl, oleyl and bezyl alcohol, phenols, naphthols and their alkylation products, ethylene and propylene adducts from the aforenamed compounds which have one to 90, preferably one to 60, alkylene oxide units.
  • polyglycols and copolymers of polyethylene and polypropylene oxide the compounds having a molecular weight of about 200 to 6,000 deserve special mention.
  • the suitable sulphonating agents include sulphuric acid, sulphur trixode, chlorosulphonic acid, bisulphite and sulphur dioxide, in the presence of chlorine or oxygen.
  • the resins applied in conjunction with the disclosed compounds are preferably aminoplasts, which impart a crease resistant finish to textile substrates.
  • N-methylol urea or M-methylol melamine compounds can be used for this purpose with good success.
  • Other suitable resins are urea, melamines, e.g.
  • alkylolamides e.g. methylol formamide, methylolacetamide
  • acrylamides e.g. N- methylolformamide, N-methylolmetacrylamide, N-methylmethylolacrylamide
  • diureas e.g. trimethylol and tetramethylol acetylene diurea
  • triazones e.g. dimethylol-N-ethyltriazone
  • haloacetamides e.g.
  • N- methylol-N-methylchloracetamide urones, e.g. dimethylolurone and dihydroxydimethylolurone, and mixtures of these resins.
  • the resin finishing of textiles is carried out preferably in the presence of catalysts.
  • the salts of multivalent metals with strong mineral acids, ammonium and amine salts and acids are used as catalysts for the reaction of N-methylol compounds.
  • the suitable salts include the magnesium and zinc nitrates. phosphates and halides, zinc oxychloride, combinations of boric acid and calcium chloride, acetates. e.g. of zinc or magnesium.
  • Ammonium sulphate, chloride and bromide are suitable ammonium salts; monoammonium and diammonium phosphate and alkanolamino hydrochlorides such as mono-. diand triethanolamino hydrochloride can also be used.
  • acids examples include hydrochloric, sulphuric and phosphoric acid, but preference is given to lower aliphatic acids such as propionic, glycolic, lactic, tartaric, citric and oxalic acid, and in particular formic or acetic acid, either alone or in combination with the aforestated metal salts.
  • succinic, maleic, sulphanilic and other acids are also suitable. These acids can be used alone or in combination.
  • the compounds of this invention are applied to textile substrates in combination with a resin, preferably one of the aforenamed N- methylol resins, and a catalyst. They are applicable to natural cellulosic (cotton, linen, hemp) and regenerated cellulosic fibres (viscose and cuprammonium rayon, polynosic and high wet modulus fibres), polyester, polyacrylonitrile, polypropylene, polyamide and other synthetic fibres, including blends of these fibres. They are of special interest for finishing cotton and polyester textiles.
  • the substrate may be present as loose fibre, yarn, woven or knit fabric, carpeting, felts or nonwovens, or in other textile forms.
  • the compounds of formula (I) are applied to the high-polymer textile substrates in combination with optionally precondensed resins from aqueous-organic or preferably aqueous medium using the known methods. It is preferable to employ the said compounds and resins in the form of preparations which may contain, for example, 10 to 90 percent of a compound of formula (I) and 10 to 90 percent resin, though the optimum ratio of the compound to the resin is :30 to l0z90. Any of the standard methods of application is employable by means of which the preparations, if necessary after prior dilution, can be deposited on the substrate, for example padding, spraying, coating, dipping, printing, screen or foam application.
  • the substrate prefferably finished with 0.01-10 percent or preferably 0.1-3 percent (relative to its weight) of the selected compound of formula (I) in combination with the resin.
  • the textiles are dry heat treated for fixation of the finish.
  • a suitable technique for applying the products of this invention jointly with N-methylol type resins is as follows. 50-300 or preferably 200-250 parts by weight of an approximately 50 percent aqueous solution of the N-methylol compound, which may if desired be partially condensed, are mixed with 20-300 or preferably 100-200 parts by weight of an almost neutral (pH-- 6-7), approximately 25 percent aqueous solution or dispersion of acompound of this invention, with the addition of 5-75 or preferably 20-30 parts by weight of one of the aforecited catalysts. The solution or dispersion is diluted to 1,000 parts with water.
  • nonylphenylpolyglycol ether with ethylene oxide groups or in place of trimellitic anhydride and oleylpolyglycol ether with 40 ethylene oxide groups 1d.
  • trimellitic anhydride and oleylpolyglycol ether with ethylene oxide groups or in place of trimellitic anhydride and oleylpolyglycol ether with 40 ethylene oxide groups 1d.
  • phthalic anhydride and oleylpolyglycol ether with ethylene oxide groups
  • EXAMPLE 3 A solution of 192 parts (1 mol) of trimellitic anhydride, 270 parts (1 mol) of stearyl alcohol and 600 parts 1 mol) of polyethylene glycol, molecular weight 600, is reacted in analogy with the preceding Example. 104 Parts (0.1 mol) of the resulting trimellitic acid diester are dissolved in 200 parts of carbon tetrachloride, after which 23 parts (0.15 mol) of phosphorus oxychloride are added The solution is held at 60 until the cal- 55 culated amount of hydrogen chloride gas has escaped, upon which the solvent is evaporated and water added to hydrolyse the residue to the phosphoric acid ester.
  • the product thus obtained is well soluble in water and is especially suitable for combined application with N- methylol compounds to produce durable soil and oil repellent finishes on textiles; these finishes impart a soft handle to the textiles and a very good antistatic effect. Moreover they have no adverse effect on the fastness properties of dyed goods.
  • polyethylene glycol of molecular weight 600 and trimellitic anhydride 3a polyethylene glycol (molecular weight 1000) and phthalic anhydride. or in place of stearyl alcohol and polyethylene glycol (molecular weight 600) 3b. stearyl amine andpolyethylene glycol (molecular weight 2.000) are used.
  • EXAMPLE 4 104 Parts (0.1 mol) of the trimellitic acid diesterobtained as intermediate in Example 3 are dissolved in 200 parts of carbon tetrachloride, with the subsequent dropwise addition of 1 1.7 parts (0.1 mol) of chlorosulphonic acid. The solution is maintained at 60 until the calculated amount of hydrogen chloridegas has escaped, then the solvent is evaporated.
  • the sulphuric acid ester thus formed is well dispersible in water and is excellent for soil repellent finishing, having compara bly good properties to the products obtained by the 20 procedure of Example 3.
  • EXAMPLE 5 A solution of 296 parts (2 mols) of phthalic anhydride and 1,000 parts (1 mol) of polyethylene glycol, molecular weight 1,000, is held at 160180 until the acid number reaches the value calculated for 2 equivaboil and held at this temperature long enough for the calculated amount of water to be distilled and the acid number to reach approximately the theoretical value. The solvent is then removed by distillation. A soft, waxlike product of beige colour is obtained when in the form of the sodium salt is readily soluble in water and shows particularly good soil repellent and antistatic properties.
  • polyethylene glycol molecular weight 1,000
  • stearyl alcohol 5a molecular weight 600
  • octanol can be employed, on which a product with comparable properties is formed.
  • EXAMPLE 6 A solution of 19.2 parts (0.1 mol) of citric acid, 203 parts (0.1 mol) of oleylpolyglycol ether with 40 ethylene oxide groups, 0.2 part of p-toluenesulphonic acid and 150 parts of xylene is set for reaction in a vessel equipped with stirrer and water separator. It is raised to the boil and held at this temperature until the acid number reaches the calculated value. After removal of the solvent by distillation, a pale, wax-like product of 7 soft texture is obtained which is well soluble in water and is highly suitable for the soil repellent finishing of textiles.
  • EXAMPLE 7 A solution of 19.2 parts (0.2 mol) of maleicanhydride and 274 parts (0.2 mol) of oleylpolyglycol ether with 25 ethylene oxide groups is reacted at 130-l50 until the acid number reaches the theoretical value. A solution of 25.2 parts (0.2 mol) of sodium sulphite in 100 ml of water is added, after which stirring is continued for 2 to 3 hours at 80. The iodine consumption of a sample drops virtually to zero after this time. A 25 percent aqueous solution is obtained which has very good soil repellent and antistatic properties.
  • Products with equally good properties can be obtained by substituting for oleylpolyglycol ether with 25 ethylene oxide groups 7a. nonylphenylpolyglycol ether with 12 ethylene oxide groups or 7b. nonylphenylpolyglycol ether with 30 ethylene oxide groups.
  • EXAMPLE 8 The solution for reaction is prepared with 137 parts (0.1 mol) of oleylpolyglycol ether having 25 ethylene oxide groups, 11.6 parts (0.1 mol) of the sodium salt of monochloracetic acid, 4 parts of sodium hydroxide, 0.16 part of sodium carbonate and 0.6 part of water. It is reacted for 5 hours at 100, during which time the acid consumption of a sample decreases practically to zero. The product is readily soluble in water and has notably good power of soil repellency.
  • EXAMPLE 9 In analogy with Example 8, a solution of 150 parts (0.2 mol) of glycerotripolyglycol ether having three times 5 ethylene oxide groups, 70 parts (0.6 mol) of the sodium salt of monochloracetic acid, 24 parts (0.6 mol) of sodium hydroxide, 1 part of sodium carbonate and 5 parts of water is reacted to yield a yellowish product which is well soluble in water. It is highly suitable for the soil repellent and antistatic finishing of textiles.
  • 9a glycerotripolyglycol ether with three times 20 ethylene oxide groups or 9b. glycerotripolyglycol ether with three times 40 ethylene oxide groups.
  • EXAMPLE 10 A solution of 500 parts (0.25 mol) of polyethylene glycol, molecular weight 2,000. 46.2 parts (05 mol) of epichlorohydrin and a small amount of borotritluoroetherate is reacted in the known manner to form the dichlorohydrin ether. A solution of 20 parts (0.5 mol) of sodium hydroxide in 20 parts of water is added to convert the ether into the diepoxide. The separated sodium chloride is removed by filtration and the diepoxide dropped into 250 parts of 25 percent ammonia at room temperature for conversion into the diamine. When the end-point of the reaction is reached the batch is evaporated to dryness. A clear brownish product is obtained in a yield of 481 parts, its content of diamine (determined by filtration with perchloric acid) being approximately percent.
  • the polyethylene glycol of molecular weight 2,000 can be replaced by 10a.
  • the molar ratio of the chosen polyethylene glycol of molecular weight 300-2,000 to the sodium salt of monochloracetic acid can be changed from 1:2 to a ratio between 1:4 and 1:6, upon which products with comparable properties are formed.
  • EXAMPLE 1 l EXAMPLE 12
  • a solution of 49 parts (0.5 mol) of maleic anhydride, 270 parts (0.1 mol) of stearyl alcohol, 0.5 part of p-toluenesulphonic acid as catalyst and parts of toluene as decelerating agent is prepared in a sulphonation vessel titted with a water separator. It is reacted for 5 hours at boiling temperature with reflux, during which time 8 millilitres of water is collected while the acid number decreases practically to zero.
  • a blend fabric of 67 percent polyester fibre and 35 percent cotton is padded with an aqueous dispersion containing 250 g/l of 50 percent aqueous dimethylol dihydroxyethyl urea, 25 g/l of Zn(NO -6l-1 O and 200 g/l of the 25 percent aqueous (pH 6.5-7) product of Example 1, the expression on the padding machine giving a 75-80 percent increase on the dry weight.
  • the fabric is dried at 120 and dry heat treated for 5 minutes at 160 for fixation of the finish. It is then cut into two halves. The first half is washed once and the second five times for 30 minutes at 60 with a commercial detergent. The two samples are then submitted to the tests described below.
  • a. Oil spotting test The sample is spotted with used automobile oil, washed and assessed for ease of oil removal.
  • b. Soil deposition in washing The sample is washed, dried and washed again in a wash bath set with 6 g/l of a fully active detergent and 5 g/l of an artificial soil mixture consisting of 38 peat l7 cement l7 china clay diatomaceous earth 0.5 Zn ferric oxide automobile oil gas soot flame soot The degree of greying due to deposition of these impurities on the fabric in washing is assessed.
  • APPLICATION EXAMPLE B A fabric of 67 percent polyester fibre and 33 percent cotton is padded at a liquor pickup of 75-85 percent with a liquor containing 250 g/l of percent aqueous dimethylol methylcarbamate, 25 g/l of'zinc chloride and 200 g/l of the 25 percent aqueous (pH 6.5-7) prod uct of Example 4. After drying at 120 the finish is fixed by dry heat treatment for 5 minutes. The fabric is cut in two and the two samples tested for soil repellency and soil deposition in washing by the methods given in the preceding Application Example.
  • test results are evaluated on a numerical scale from 1 to 5, where 5 represents excellent and 1 poor behaviour in the test.
  • the two synthetic resins referred to in the first column of the table are di methyl dihydroxy ethylene urea (I) and dimethylol propylene urea (11).
  • R is hydrogen or a saturated or unsaturated alkyl or an aromatic radical or an aliphatic carboxylic acid radical which has one to 30 carbon atoms or the radical of an inorganic acid,
  • n is zero or 1 to 100
  • y is zero or 1
  • p 1 to 4
  • X is -NH- or COO wherein B is hydrogen or an alkali-metal ion and d is l or 2,
  • R is an alkyl radical which has eight to 30 carbon atoms
  • n zero or 1 to 10
  • R contains one to 40 carbon atoms and is an alkyl, alkenyl or phenyl radical bound to the remainder of the compound of formula (I) through p groups capable of binding an active hydrogen and selected from -O-, -S-,
  • L is alkyl or alkenyl of one to 30 carbon atoms, said R, when alkyl, being unsubstituted or substituted by phenyl, naphthyl, diphenylether, diphenylsulphide or diphenylmethane, and
  • R is a member of the group consisting of hydrogen
  • a process as in claim 1 wherein the textile material consists of cellulosic fibers, synthetic fibers, or mixtures thereof.
  • aliphatic carboxyllc acid radical WhlCh has one to Hg-0- v 30 carbon atoms or a radical of an organic acid, 000- CH1-o- 0Hcoo- E is oxygen or -NH-, 6H, (om), HO- COOH R gsiilclgldrogen or a saturated or unsaturated alkyl OOH HPCOOH r R is hydrogen or a carboxyl or sulphoxyl group, CXBHNWW 0113130001 OHHHCOCP, 918E130, R is hydrogen or a carboxyl group, and 6111133000 n is zero or a value from one to 100. d 10.
  • R2 is a sulphoxyl group, 12.
  • a process according to claim 6 wherein in com- 13.
  • a process as in claim 8 wherein the compound of pound formula (I) and the methylol compound are used in the R is weight ratio of 1:04 to 1:10.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US00210116A 1970-12-22 1971-12-20 Crease resistant finish for textiles having improved soil repellent properties Expired - Lifetime US3821023A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959230A (en) * 1974-06-25 1976-05-25 The Procter & Gamble Company Polyethylene oxide terephthalate polymers
US4702857A (en) * 1984-12-21 1987-10-27 The Procter & Gamble Company Block polyesters and like compounds useful as soil release agents in detergent compositions
CN103628312A (zh) * 2013-11-27 2014-03-12 常熟市赵市圣丹龙制衣厂 纯棉织物抗皱整理方法
ITMI20122127A1 (it) * 2012-12-13 2014-06-14 Epitech Group Srl Derivati polietilenglicolici di palmitoiletanolammide e aciletanolammidi analoghe

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Publication number Priority date Publication date Assignee Title
DE3247407A1 (de) * 1982-12-22 1984-06-28 Chemische Fabrik Pfersee Gmbh, 8900 Augsburg Waessrige emulsionen und verfahren zum weichmachen von fasermaterial, insbesondere von textilmaterial

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FR767736A (d) * 1933-01-30 1934-07-23
CH210762A (de) * 1935-06-18 1940-07-31 Chem Ind Basel Verfahren zur Darstellung eines Oxyketonesters der Androstenreihe.
US3003954A (en) * 1957-07-19 1961-10-10 Staley Mfg Co A E Methods and compositions of matter for softening textile fibers, yarns, and fabrics
GB895098A (en) * 1958-01-06 1962-05-02 Calico Printers Ass Ltd Improvements in the finishing of cellulosic textiles
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959230A (en) * 1974-06-25 1976-05-25 The Procter & Gamble Company Polyethylene oxide terephthalate polymers
US4702857A (en) * 1984-12-21 1987-10-27 The Procter & Gamble Company Block polyesters and like compounds useful as soil release agents in detergent compositions
ITMI20122127A1 (it) * 2012-12-13 2014-06-14 Epitech Group Srl Derivati polietilenglicolici di palmitoiletanolammide e aciletanolammidi analoghe
EP2742957A1 (en) * 2012-12-13 2014-06-18 Epitech Group S.r.l. Polyethylene glycol derivatives of palmitoylethanolamide and analogous acylethanolamides
US9522192B2 (en) 2012-12-13 2016-12-20 Epitech Group S.R.L. Polyethylene glycol derivatives of palmitoylethanolamide and analogous acylethanolamides
CN103628312A (zh) * 2013-11-27 2014-03-12 常熟市赵市圣丹龙制衣厂 纯棉织物抗皱整理方法

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IT943286B (it) 1973-04-02
BR7108419D0 (pt) 1973-06-14
NL7117643A (d) 1972-06-26
CH1894970A4 (d) 1974-05-15
BE777170A (fr) 1972-06-22
NL158862B (nl) 1978-12-15
CA979157A (en) 1975-12-09
AU3670571A (en) 1973-06-14
GB1379899A (en) 1975-01-08
FR2119010A1 (d) 1972-08-04
DE2162620B2 (de) 1977-05-12
HK29977A (en) 1977-06-17
ES398153A1 (es) 1975-03-16
CH555926A (d) 1974-11-15
JPS5221120B1 (d) 1977-06-08
FR2119010B1 (d) 1975-03-14
DE2162620A1 (de) 1972-09-14

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