WO1992017336A1 - Composition d'appret intachable destinee a des tissus en polyester - Google Patents

Composition d'appret intachable destinee a des tissus en polyester Download PDF

Info

Publication number
WO1992017336A1
WO1992017336A1 PCT/US1992/002450 US9202450W WO9217336A1 WO 1992017336 A1 WO1992017336 A1 WO 1992017336A1 US 9202450 W US9202450 W US 9202450W WO 9217336 A1 WO9217336 A1 WO 9217336A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
composition
soil release
polyester textile
polyester
Prior art date
Application number
PCT/US1992/002450
Other languages
English (en)
Inventor
William A. Williams, Jr.
Original Assignee
Ppg Industries, Inc.
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 Ppg Industries, Inc. filed Critical Ppg Industries, Inc.
Publication of WO1992017336A1 publication Critical patent/WO1992017336A1/fr

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • D06M13/152—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 having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • D06M15/507—Polyesters

Definitions

  • polyester textiles are commonly used in a wide variety of consumer and industrial applications.
  • One disadvantage of polyester textiles is the difficulty in removing oily residues, i.e., naphthenic, aliphatic or alkane hydrocarbon residues, such as motor oil, tar, pitch, lubricating oil or the like, from the material once it has been soiled with such residues. This is in part due to the hydrophobic nature of the polyester textile which makes the material difficult to wet with aqueous laundering materials.
  • soil release compositions have been developed for application to polyester textiles.
  • These soil release compositions which are typically comprised of non-fiber forming polyether-polyester copolymers, modify the polyester textile surface to enable release and removal of oily residues from the polyester textile using conventional laundry techniques.
  • Typical polymeric soil release compositions are described, e.g., in U.S. Patent No. 3,416,952.
  • Heat setting aligns the crystal morphology of the polyester fibers to a more parallel rather than random orientation.
  • heat setting is typically effected at a temperature of at least about 375° F. (about 191° C.) to speed throughput and to better control fabric shrinkage. Such temperatures may range up to about 405° F. (about 207° C.) or so.
  • an antioxidant material may be included in the soil release composition to retard or prevent its thermal degradation during the heat setting step.
  • antioxidant materials typically used to impart thermal stability to the polymeric soil release compositions described therein include sterically hindered phenols, aromatic amines or organic sulfur compounds.
  • none of the antioxidant materials specifically disclosed therein satisfactorily retard or 5 prevent thermal degradation of the polymeric soil release composition at polyester textile heat set temperatures of about 375" F. (191° C.) or higher.
  • polyester textiles finished with such soil release compositions and heat set at such elevated temperatures have unsatisfactory soil release properties resulting 10 in incomplete removal of oily residues from the textile when using conventional laundering techniques.
  • Figure 1 is a high performance liquid chromatographic 15 (HPLC) tracing of a sample of antioxidant material used in the soil release composition of the invention.
  • This invention provides a thermally stable soil release 20 composition for application to polyester textiles, particularly to polyester textiles that are heat set at temperatures of at least about 375" F. (191° C.)
  • the soil release composition of the invention when applied to or finished on polyester textile prior to heat setting is not only durable at such heat set temperatures but 25 also enables release and removal.of oily residue from the polyester textile without staining or discoloration when using conventional laundering techniques.
  • the term heat set as used herein is intended to mean the thermal treatment of polyester textile, typically at a temperature in the range of from about 375° F. (191° C.) to about 30 405° F.
  • Oily residues as used herein are meant to include naphthenic, aliphatic or alkane hydrocarbons such as motor 5 oil, pitch, tar, or the like.
  • Conventional laundry techniques are those employed to wash and dry fabrics using commercially available detergents and laundry aids with washing and drying apparatus found in the home or commercial laundries.
  • the soil release composition of the invention comprises a non-fiber forming polyester-poiyether copolymer and a sterically hindered phenol antioxidant material, the latter of which is the butylated reaction product of p-cresol and dicyclopentadiene.
  • Non-fiber forming polyester-poiyether copolymers e.g., polyethylene terephthalate - polyoxyethylene terephthalate (PET - POET) copolymers and their use as soil release promoting agents for polyester textiles are well known to the art.
  • PET - POET copolymers typically having an average molecular weight in the range of from about 5,000 to about 50,000, may be prepared, e.g., by the ester interchange and subsequent polymerization of dimethyl terephthalate (WT) and ethylene glycol (EG) in the presence of a mixed catalyst system as described in U.S. Patent No. 3,557,039.
  • U.S. Patent No. 3,959,280 describes a similar mode of preparation using polyethylene oxide in addition to the DMT and EG reactants.
  • PET - POET soil release promoting copolymers are commercially available from a number of manufacturers.
  • the copolymeric material of which the soil release composition of the invention is comprised preferably contains from about 10 to 50% by weight of ethylene terephthalate repeat units together with from about 90 to 50% by weight of polyoxyethylene terephthalate repeat units which have been derived from a polyoxyethylene glycol having an average molecular weight of from about 1000 to about 4000, and wherein the molar ratio of ethylene terephthalate repeat units to polyoxyethylene terephthalate repeat units is from about 2:1 to about 6:1.
  • a preferred copolymeric material for use in the composition of the invention comprises the reaction product of ethylene glycol, dimethyl terephthalate and a polyoxyethylene glycol containing from 1 to about 50 ethylene oxide repeat units which may be prepared as described, e.g., in Example 11 of U.S. Patent 3,416,952.
  • a particularly preferred copolymeric material of which the soil release composition of the invention is comprised is commercially available from PPG Industries, Inc. under the trademark, "Larosol 214A". This material is available as an aqueous dispersion of the reaction product of ethylene glycol, 5 dimethyl terephthalate and polyoxyethylene glycol, the latter having an average molecular weight of about 1450.
  • PET - POET type polymeric composition particularly suitable for use in the invention is a product sold by ICI America under the trademark, "Milease T".
  • the Milease T material believed to be that prepared according to Example 19 of U.S. Patent 3,416,952 also contains an antioxidant believed to consist of zinc dinonyldithiocarbamate and 2- ⁇ -methylcyclohexyl-4,6-dimethylphenol.
  • the antioxidant material used in the soil release composition of the invention is the butylated reaction product of dicyclopentadiene and p-cresol This antioxidant is a sterically hindered phenol, the field absorption mass spectrum of which is depicted and discussed in Rubber Chem. Technol., Vol. 53(1), pp. 154-155 (1980). This antioxidant material may be prepared in a manner analogous to that described in U.S. Patent No. 3,935,281, the teachings of which respecting the mode of preparation are incorporated by reference herein.
  • the antioxidant material may be prepared by reacting dicyclopentadiene with p-cresol in the presence of an inert organic solvent followed by reaction of the product with isobutene in the presence of a suitable alkylation catalyst.
  • the antioxidant material of which the soil release composition of the invention is comprised is also commercially available from The Goodyear Tire & Rubber Co. under the trademark, "Wingstay L".
  • Figure 1 is an HPLC tracing of a sample of Lot No. 10218-4 of said commercially available Wingstay L material.
  • the major component which is believed to be the active component, elute ⁇ at a retention time of about 31.8 minutes, this component having an area % of about 40. (The sharp peak eluting at a retention time of about 33 minutes is, of course, characteristic of the carrier solvent.)
  • Said major component has the empirical formula, C ⁇ H ⁇ O and may be represented by the structural formula:
  • each R represents a methyl group.
  • the HPLC tracing of Figure 1 was generated using a Hewlett Packard 1090L high performance liquid chromatograph equipped with a diode array detector and autosampler using a PE Nelson Access Chrome Data System for quantitation.
  • the column was a 4.6 mm X 15 cm Dychrom column packed with Chemcosorb 5-ODS-UH and the guard column was a 2 cm X 2 mm Upchurch column packed with Per aphase ODS.
  • the column temperature was 40° C
  • the injection volume was 1 microliter
  • the detector wavelength was 280 nm (bandpass 4 nm) with reference at 550 nm (bandpass 50 nm).
  • Mobile phase program A was water with 0.005% v/v triethylamine and mobile phase program B was acetonitrile with 0.005% v/v triethylamine.
  • the flow rate was 1.5 milliliters per minute.
  • the effective amount of antioxidant material incorporated in the soil release composition is an antioxidant effective amount, i.e., an amount which provides thermal stability to the copolymeric material at heat set temperatures of at least 375° F. (191° C.) and which does not adversely affect the durability of the copolymeric material.
  • an antioxidant effective amount i.e., an amount which provides thermal stability to the copolymeric material at heat set temperatures of at least 375° F. (191° C.) and which does not adversely affect the durability of the copolymeric material.
  • the herein described antioxidant material is used most advantageously in the invention composition in antioxidantly effective or thermal stabilizing amount ranging from about 0.5 to about 2.0% by weight, and preferably from about 0.75 to about 1.5% by weight based on the weight of the copolymeric material.
  • Polyester textiles to which the soil resistant composition of the invention may be applied include dyed or undyed, woven or nonwoven polyester cloth as well as polyester fiber, filament or yarn used to make such cloth, which polyester fiber may also be blended with varying amounts of natural materials, e.g., wool or cotton.
  • the polyesters commonly used as textiles are those fiber forming polyesters which are typically made by reacting a dicarboxylic acid or ester forming derivative thereof with a glycol to form the bis-glycol esters of the acid. The ester is then typically condensed at elevated temperature and reduced pressure to eliminate excess glycol and produce the glycol ester polymer of the dicarboxylic acid.
  • Suitable glycols used in the manufacture of fiber forming polyester include, e.g., ethylene glycol, diethylene glycol, polyethlyene glycol or other alkylene glycols, including mixtures thereof.
  • dicarboxylic acids terephthalic acid is commonly used in the manufacture of fiber forming polyester although a portion of the terephthalic acid may be replaced by one or more other dicarboxylic acids, such as adipic acid, sebacic acid, isophthalic acid or the like.
  • the soil release composition of the invention is typically formulated as an aqueous emulsion containing at least about 60% by weight of water and typically from about 70 to about 90% by weight water.
  • the aqueous emulsion contains about 85% by weight water and the balance active material, i.e., the antioxidant-containing copolymeric material.
  • the invention composition may be applied to the polyester textile by any conventional technique, e.g., padding, pressure jet, dye vat, or the like. Regardless of the mode of application, sufficient of the invention composition is applied to or finished on the polyester textile so as to provide from about 0.3 to about 1.5% by weight, and preferably from about 0.5 to about 0.9% by weight of the active soil release composition, i.e., undiluted invention composition, based on the weight of polyester textile undergoing treatment.
  • the soil release composition of the invention is compatible with other typically used polyester textile treatment or conditioning materials such as, e.g., dyes, dye carriers, defoa ers, anti-cracking aids, brightening agents, other antioxidant materials, or the like.
  • Example 1 An aqueous dispersion containing about 15% by weight of Larosol 214A copolymeric material comprising the reaction product of ethylene glycol, dimethyl terephthalate and polyoxyethylene glycol, the latter having an average molecular weight of about 1450 was applied to 6" X 18" swatches of Dacron type 54 and type 64 100% polyester fabrics, each swatch weighing about 12.5 grams.
  • the copolymeric material was applied to the fabric from an aqueous bath adjusted to pH 4.5 to 5.0 with acetic acid and containing about 1.0% by weight on weight of fabric of Palanil Yellow 3GN dye (DISPERSE YELLOW #64, CI No.
  • a 6" X 6" portion of the fabric swatch was spotted with about 0.1 milliliter of filtered, used crankcase oil, which oil was allowed to wick into the fabric. The fabric swatch was then washed and rinsed in a conventional home washing machine using 90 grams of AATCC standard laundry detergent #124. The oil spotted portion was severed from the swatch and the remaining 2/3 of the swatch was washed four times more and dried. Another 6" X 6" portion of the swatch was oil spotted, washed and dried once as before and severed from the swatch. The remaining 6" X 6" portion of the swatch was washed five more times and the drying, oil spotting and washing procedure was repeated.
  • the fabric swatches were then visually evaluated for soil release properties and durability, i.e., soil release as a function of the number of washing - drying cycles. More particularly, the soil release properties of the fabric swatches were evaluated using the following Rating Scale:
  • Table 1 summarizes the results of the test swatches of Dacron 54 an 64 treated in accordance with this Example 1.
  • Example 2 The test procedure described in Example 1 was repeated except that the Dacron polyester fabric swatches were undyed and heat set at a temperature of 375° F. (191° C). None of the tested swatches exhibited acceptable soil release properties, i.e., durability was poor and discoloration progressively worsened as a function of repeat washing cycles. More particularly, using the Rating Scale described in Example 1, the swatches tested in accordance with this Example 2 are as set forth in Table 2, as follows:
  • Example 2 A number of commercially available materials were evaluated to determine their ability to thermally stabilize the copolymeric soil release material, i.e., Larosol 214A, described in Example 1 at a heat set temperature of about 395° F. (202° C).
  • the materials evaluated were Irganox 1010, Irganox 1035 and Irganox 1076 polymeric sterically hindered phenols (trademarked products of Ciba Geigy); butylated hydroxy toluene (BHT); Cyanox LTDP dilaurylthiodi- propionate (trademarked product of American Cyanamid Co.); Plas-Chek 775 epoxidized soybean oil (trademarked product of Ferro, Inc.); and Wingstay L (Lot No.

Abstract

Cette invention concerne une composition d'apprêt intachable destinée à être appliquée sur un tissu en polyester ou à être utilisée dans le traitement de finition dudit tissu. Ladite composition est thermofixée à une température au moins égale à 375 °F (191 °C) et comprend un copolymère polyester-polyéther non fibrogène et une quantité efficace au niveau antioxydant du produit de réaction butylé du dicyclopentadiène avec du p-crésol.
PCT/US1992/002450 1991-04-08 1992-03-26 Composition d'appret intachable destinee a des tissus en polyester WO1992017336A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68128591A 1991-04-08 1991-04-08
US681,285 1991-04-08

Publications (1)

Publication Number Publication Date
WO1992017336A1 true WO1992017336A1 (fr) 1992-10-15

Family

ID=24734614

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/002450 WO1992017336A1 (fr) 1991-04-08 1992-03-26 Composition d'appret intachable destinee a des tissus en polyester

Country Status (2)

Country Link
MX (1) MX9201607A (fr)
WO (1) WO1992017336A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7144600B2 (en) * 2003-02-18 2006-12-05 Milliken & Company Wax-free lubricant for use in sizing yarns, methods using same and fabrics produced therefrom
WO2007012575A2 (fr) * 2005-07-25 2007-02-01 Basf Se Preparations pigmentaires solides contenant des additifs tensioactifs solubles dans l'eau et des agents antioxydants
US7579047B2 (en) 2003-05-20 2009-08-25 Milliken & Company Lubricant and soil release finish for textured yarns, methods using same and fabrics produced therefrom
CN104508199A (zh) * 2012-06-15 2015-04-08 罗地亚经营管理公司 恢复或增加聚酯织物吸水性的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3416952A (en) * 1963-06-05 1968-12-17 Ici Ltd Surface modifying treatment of shaped articles made from polyesters
US3979306A (en) * 1972-11-21 1976-09-07 Kao Soap Co., Ltd. Method and composition for finishing clothings to prevent yellowing

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3416952A (en) * 1963-06-05 1968-12-17 Ici Ltd Surface modifying treatment of shaped articles made from polyesters
US3979306A (en) * 1972-11-21 1976-09-07 Kao Soap Co., Ltd. Method and composition for finishing clothings to prevent yellowing

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7144600B2 (en) * 2003-02-18 2006-12-05 Milliken & Company Wax-free lubricant for use in sizing yarns, methods using same and fabrics produced therefrom
US7579047B2 (en) 2003-05-20 2009-08-25 Milliken & Company Lubricant and soil release finish for textured yarns, methods using same and fabrics produced therefrom
WO2007012575A2 (fr) * 2005-07-25 2007-02-01 Basf Se Preparations pigmentaires solides contenant des additifs tensioactifs solubles dans l'eau et des agents antioxydants
WO2007012575A3 (fr) * 2005-07-25 2008-01-03 Basf Ag Preparations pigmentaires solides contenant des additifs tensioactifs solubles dans l'eau et des agents antioxydants
CN104508199A (zh) * 2012-06-15 2015-04-08 罗地亚经营管理公司 恢复或增加聚酯织物吸水性的方法

Also Published As

Publication number Publication date
MX9201607A (es) 1992-10-01

Similar Documents

Publication Publication Date Title
US3981807A (en) Durable textile treating adducts
EP0428639B1 (fr) Traitement antitaches pour fibres polyamides
US4219625A (en) Fluorinated polyol esters
US3854871A (en) Textile cleaning process for simultaneous dry cleaning and finishing with stain repellent
US4614519A (en) Soil release agent for textiles
US5234753A (en) Soil release composition for use with polyester textiles
US4330588A (en) Process for modifying the surfaces of polyester fibers
US5935484A (en) Lubricant and soil release finish for yarns
EP0002951B1 (fr) Des matériaux textiles ayant des caractéristiques durables de dégagement de saletés et de transport d'humidité et procédé pour la production de ces matériaux textiles
US4803256A (en) Method of altering the surface of a solid synthetic polymer
EP0002950B1 (fr) Des matériaux textiles ayant des caractéristiques durables de dégagement de saletés et de transport d'humidité et procédé pour la production de ces matériaux textiles
US3784355A (en) Solvent dyeing or solvent creaseproofing with steam and solvent vapor drying
US3521993A (en) Soil releasing textiles
US3598515A (en) Methods fof applying soil-release compositions to textile materials
WO1992017336A1 (fr) Composition d'appret intachable destinee a des tissus en polyester
US5370933A (en) Soil release composition for use with polyester textiles
US3597268A (en) Method of imparting soil resistance to synthetic textile materials and the resulting materials
US3956350A (en) Process for the production of textile softeners
EP0372782A2 (fr) Méthode de traitement de fibres cellulosiques
EP0051353B1 (fr) Procédé de modification de la surface de fibres synthétiques
US3843579A (en) Water in oil fluoropolymer emulsion containing hydrocarbon or halogenated hydrocarbon solvent
CA1050208A (fr) Agent d'ignifugation de matiere synthetique fibreuse
CA1181205A (fr) Procede d'obtention d'un pli permanent au moyen de composes d'organosilicium sans formaldehyde et textiles ainsi traites
US3457213A (en) Coapplication of softeners with an acid halide containing polymeric shrinkproofing agent to textile fibers
CA1071225A (fr) Traitement antitaches pour survetements

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): BR CA JP KR

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA