EP0105464A2 - Agents de finissage pour textile - Google Patents

Agents de finissage pour textile Download PDF

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Publication number
EP0105464A2
EP0105464A2 EP83109682A EP83109682A EP0105464A2 EP 0105464 A2 EP0105464 A2 EP 0105464A2 EP 83109682 A EP83109682 A EP 83109682A EP 83109682 A EP83109682 A EP 83109682A EP 0105464 A2 EP0105464 A2 EP 0105464A2
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EP
European Patent Office
Prior art keywords
radical
carbon atoms
composition
weight
radicals
Prior art date
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Application number
EP83109682A
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German (de)
English (en)
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EP0105464A3 (fr
Inventor
David S. Ansel
Eugene Ray Martin
Paul A. Manis
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Wacker Chemical Corp
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Wacker Chemical Corp
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Publication of EP0105464A2 publication Critical patent/EP0105464A2/fr
Publication of EP0105464A3 publication Critical patent/EP0105464A3/fr
Withdrawn legal-status Critical Current

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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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences

Definitions

  • the present invention relates to textile finishes and more particularly to textile finishing compositions for treating textile materials to impart dimensional stability, improved wetting properties and softness to the treated materials and to a process for applying textile finishing compositions to textile materials.
  • Textile materials have been treated with silicone containing materials to impart a soft hand to the treated materials.
  • U. S. Patent No. 3,812,201 to Bey discloses treating textile materials with a composition containing a carboxy functional siloxane and a durable press resin to improve the tear strength, abrasion resistance and flat appearance.
  • U. S. Patent No. 4,170,581 to Griffin discloses treating cellulose containing fabrics with a silicone-containing durable, press resin composition obtained from the polymerization of a polydimethylsiloxane which has been emulsified in an aqueous solution of dimethylolethylene urea or dimethyloldihydroxyethylene urea to provide wrinkle-recovery and impart durable press properties to cellulose containing fabrics.
  • silicones and silicone containing materials are generally good softeners, they impart hydrophobicity to a textile article which can impede printing and make the article uncomfortable to wear due to the fact that the article does not wick away body perspiration.
  • cotton material has been treated with aldehydes, acetals and aldehyde-urea reaction products to improve the dimensional stability of the treated material.
  • fabrics treated with aldehydes or acetals have generally been unsatis-factory due to poor uniformity of treatment which leads to variable dimensional stability.
  • Fabrics treated with dimethylol dihydroxyethylene urea give good dimensional stability; however, the residual formaldehyde levels on the treated fabric are high due to the degradation products of this compound.
  • the toxicological properties of formaldehyde are increasingly becoming a concern of the textile industry.
  • a textile finishing composition which improves the uniformity of I treatment with an aldehyde and/or acetal, thereby enhancing dimensional stability.
  • Another object of this invention is to provide a textile finishing composition which when applied to textile materials provides a finish which does not release high levels of formaldehyde.
  • Another object of this invention is to provide a textile finish which has wetting properties that allow good printing and allow body perspiration to be wicked away.
  • a further object of this invention is to provide a textile finishing composition, which when applied to textile materials, imparts a soft hand to the treated materials.
  • a textile finishing composition comprising (1) a silylated polyether, (2) a compound selected from the group consisting of (a) aldehydes, (b) acetals and (c) mixtures thereof and (3) a diluent.
  • the textile finishing composition may be combined with an acid catalyst in a treating bath and applied to textile materials to impart dimensional stability, improved wetting properties and a soft hand.
  • A which may be the same or different is a silicon containing radical selected from the group consisting of cationic or anionic radicals of the formula and nonionic radicals of the formula R 2 and R 3 which may be the
  • A is a divalent radical and contains a dication or dianion
  • the ratio of A to R is 1:2 and when R is a cation, then A must be an anion, and when R is an anion, then A must be a cation and when R is a nonionic radical, then A must be a nonionic radical
  • a is a number of from 0 to 4
  • b, c and d are each 0 or 1, the sum of b, c and d must be at least 1, and when b, c or d are 0, then R must be NH 2 , hydroxyl or hydrocarbonoxy radical or a radical of the formula e is a number of from 0 to 2, f which may be the same or different is 0 or 1, and when f is 0, then R 5 is a divalent hydrocarbonoxy radical linked to the silicon atom through a carbon-carbon bond, n is 2, 3 or 4, x is a number of
  • the silylated polyethers used in the textile finishes may be prepared by reacting a dicarboxylic acid or anhydride thereof with an oxyalkylene glycol or copolymers thereof or an amine terminated polymeric oxyalkylene or copolymers thereof at a temperature of from about 0 to 185°C and thereafter reacting the resultant product with an aminofunctional silane or siloxane having at least one alkoxy group at a temperature of from 0 to 110°C.
  • the silylated polyethers may also be prepared by reacting an aminofunctional silane or siloxane with a dicarboxylic acid or anhydride thereof at a temperature up to about 110°C, and thereafter reacting the resultant carboxylic acid functional silane or siloxane with an amine terminated oxyalkylene polymer or copolymer at a temperature of up to about 110°C.
  • the silylated polyethers may be prepared by reacting an oxyalkylene glycol or copolymers thereof with a dicarboxylic acid or anhydride thereof and thereafter reacting the resultant carboxylic acid polymer with a haloalkylalkoxysilane or siloxane in the presence of a basic compound such as triethylamine at a temperature up to about 150°C.
  • a basic compound such as triethylamine
  • Still another method for preparing the silylated polyethers is to react an amine terminated oxyalkylene polymer or copolymer thereof with a haloalkylalkoxysilane or siloxane at a temperature up to about 150°C and thereafter reacting the resultant product with a sodium alkoxide at a temperature up tc about 150°C.
  • Aldehydes which may be employed in the finishing compositions of this invention are saturated or unsaturated, conjugated and unconjugated aliphatic aldehydes having from 1 t 20 carbon atoms. Suitable examples include formaldehyde, ethar propanal, propenal, propynal; and various isomers of butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, unde- canal, dodecanal, tridecanal, tetradecanal, pentadecanal, hexadecanal, heptadecanal, octadecanal, ecosanal, butenal, hexenal, undecenal, furfural, and the like.
  • saturated and unsaturated conjugated and unconjugated substitut aldehydes are haloalkanals, such as chloroethanal, dichloroetha bromal, chloral, 2-bromopropanal., 2-chloropropanal, 3-chloropr panal, 2-chloro-2-methylpropanal, 2,3-dibromopropanal, 2,3-dichloropropanal, 2,2,3-trichloropropanal, 4-chlorobutanal, 2,3 dichlorobutanal, 2,2,3-trichlorobutanal and the like; hydroxy- alkanals such as glycolaldehyde, 2,'3-dihydroxypropanal, 3-hydroxybutanal, 4-hydroxypentanal, 3-hydroxy-2-methylpentanal and the like; alkylalkanals such as 2,2-dimethylpropanal, 2-ethylbutanal, 2-methylbutanal, 3-methylbutanal, 2-ethylhexanal
  • aromatic substituted or unsubstitut aldehydes examples include benzaldehyde, tolualdehydes, salicylaldehyde, 1-phenylpro p ynal, 2-benz y lidenebutanal, 2-benzylideneheptanal, hydroxybenzaldehydes, anisaldehyde, vanillan, piperanal, cinnam dehyde, carboxybenzaldehydes and the like.
  • the acetals used in the textile finishing composition of this invention may be represented by the formulas wherein R 7 may be hydrogen or a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, R 8 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms and R 9 is a divalent hydrocarbon radical having from 2 to.10 carbon atoms
  • suitable monovalent hydrocarbon radicals represented bv R 7 and R 8 above are alkyl radicals such as the methvl, ethyl, propyl, isopropyl, butvl, amvl, hexvl, octyl, decyl, dodecyl and octadecyl radicals. substituted alkyl radicals such as chloroethyl, and methoxvethvl.
  • alkenvl radicals such as vinyl, allyl, butenyl, butadienyl, 1-pentenyl, 1-decenyl, and 1-octadecenyl
  • aryl radicals such as the phenyl radical
  • aralkyl radicals such as the phenylmethyl, phenylethyl, or phenylbutyl radicals
  • alkaryl radicals such as the tolyl, xylyl, and ethylphenyl radicals
  • hydroxy and carboxy aryl, aralkyl, and alkaryl radicals alkenvl radicals such as vinyl, allyl, butenyl, butadienyl, 1-pentenyl, 1-decenyl, and 1-octadecenyl
  • aryl radicals such as the phenyl radical
  • aralkyl radicals such as the phenylmethyl, phenylethyl, or phenylbutyl
  • divalent radicals are ethylene, propylene, butylene, hexylene, octylene, decylene, ethenylene, propenylene, 1-butenylene, 2-butenylene, cyclohexylene, 3-cyclohexene-1,2-ylene and naphthenylene.
  • acetals are dimethoxymethane, diphenoxymethane, 1,1-dimethoxy-2-tolylethane, 2,2-diphenoxy- propane, 3-ethoxy-l,3-dimethoxybutane, 2,2-dimethyl-l,3-dioxo- lane and 3-chloro-1,1-diethoxypropane.
  • the textile finishing compositions of this invention may also contain from 99.5 to 50 percent by weight of a diluent based on the weight of the composition.
  • Suitable diluents are water and aliphatic alcohols having from 1 to 10 carbon atoms. Specific examples of suitable alcohols are methanol, ethanol, propanol, butanol, hexanol, octanol and decanol.
  • the diluent may be a solvent or an emulsifier or a dispersant for the silylated polyether, aldehyde or acetal.
  • the textile finishing compositions of this invention may also include silanol containing organopolysiloxanes having c viscosity of from 15 to 1,000,000 mPa.s at 25°C and more preferably from 25 to 500,000 mPa.s at 25°C.
  • the preferred organopolysiloxanes are silanol terminated polydimethylsiloxanes, although other alkylpolysiloxanes may be employed.
  • These finishes may contain from 0.5 to 99.5 percent by weight of silanol containing organopolysiloxanes and from 99.5 to 0.5 percent by weight of silylated polyethers, based on the weight of the silanol containing organopolysiloxanes and the silylated j polyethers.
  • the silylated polyether, aldehyde or acetal or mixtures thereof and diluent may be mixed in any order and at temperatures ranging from about 10° to 90°C.
  • the finishing composition may be applied to any textil material.
  • suitable textile materials are cotton, rayon, polyester, polypropylene, polyethylene, polyurethane, polyamide, wool, hemp, natural silk, cellulose acetate and polyacrylonitrile fibers as well as mixtures of these fibers.
  • the textile materials may consist of staple or monofilament fibers and fabrics made thereof.
  • finishing compositions of this invention may be applied to the textile materials by any means known in the art, such as by spraying, immersion, foaming, padding, calendering o: by gliding the fibers across a base which has been saturated with the compositions of this invention.
  • a preferred method for treating textile materials is to use a finishing bath containing from 0.16 to 30 percent by weight of silylated polyether, from 0.04 to 40 percent by weight of an aldehyde or an acetal or mixtures thereof and from 99.8 tc 30 percent by weight of diluent based on the weight of the finishing composition.
  • An acid catalyst is preferably added to the bath in an amount of from 0.5 to 50 percent by weight based on the weight of the finishing composition.
  • the acid catalyst is preferably added to the finishin bath containing the silylated polyether, aldehyde or acetal and diluent just prior to use.
  • the acid catalyst is generally present in an amount of from 0.5 to about 50 percent by weight, preferably from about 1 to 40 percent by weight and more preferably from about 2 to 30 percent by weight based on the weight of the composition containing the silylated polyether, aldehyde or acetal and diluent.
  • Suitable acid catalysts are water soluble metallic salts such as magnesium chloride, magnesium nitrate, magnesium sulfate, magnesium dihydrogenphosphate, zinc nitrate, zinc chloride, zinc tetrafluoroborate, aluminum chlorohydrate, aluminum chloride and mixtures of the above salts; water soluble ammonium and amine salts such as ammonium chloride, ammonium sulfate, aminomethylpropanol hydrochloride and aminomethylpropanol nitrate and mixtures thereof in combination with the metallic salts described above.
  • water soluble metallic salts such as magnesium chloride, magnesium nitrate, magnesium sulfate, magnesium dihydrogenphosphate, zinc nitrate, zinc chloride, zinc tetrafluoroborate, aluminum chlorohydrate, aluminum chloride and mixtures of the above salts
  • water soluble ammonium and amine salts such as ammonium chloride, ammonium sulfate, aminomethylpropanol hydrochloride and aminomethylpropano
  • catalysts which may be employed are acids such as oxalic acid, gluconic acid, phosphoric acid, tartaric acid, maleic acid, para-toluenesulfonic acid and acetic acid; and mixtures containing the above acids and the metallic salts described above.
  • the finishing bath may be'further diluted with diluent prior to treating the textile materials. It is preferred that the diluent be the same as, or at least compatible with the diluent present in the finishing composition.
  • the textile material is passed through the treating bath to provide a wet pick-up rate of from about 10 to 85 percent based on the weight of the textile material.
  • the amount of composition applied to the textile material depends on the properties desired in the treated material.
  • the treated material After applying the composition to the textile material, the treated material is heated at an elevated temperature, e.g., from 80 to 200°C for a period of time ranging from about 1.5 to about 15 minutes. If desired, the treated textile material can be dried at a temperature of about 50 to 95°C for a period of time ranging from about 1 to 10 minutes and then cured at'a temperature of from about 125 to 200°C for from about 15 to 60 seconds.
  • an elevated temperature e.g., from 80 to 200°C for a period of time ranging from about 1.5 to about 15 minutes.
  • the treated textile material can be dried at a temperature of about 50 to 95°C for a period of time ranging from about 1 to 10 minutes and then cured at'a temperature of from about 125 to 200°C for from about 15 to 60 seconds.
  • finishing compositions or the finishing baths of this invention are agents which improve abrasion resistance of the treated fibers, hand builders, materials which improve the fragrance of the treated textile materials, aminoplast or other types of thermosetting resins, antistatic agents, lubricants, fire retardant agents, soil resistant materials, organic softeners and other hydrophi oleophilic, or hydrophobic agents.
  • Anionic, cationic, nonioni and amphoteric surfactants may also be incorporated in the finishing bath of this invention.
  • Suitable organic softeners are various fatty amides, fatty amines, and fatty amido amines, amido amines, mono- and diglycerides, quaternized fatty amines, hydroxyethyldiethyl ammonium sulfate and ethoxylated stearic quaternary ammonium compounds; various fatty esters such as bu stearates, glycerol stearates; diethylene glycol stearates, an sulfonated fatty esters of polyethylene glycols and diethylene glycols; various oxyalkylene polymers such as oxyethylene polymers, oxypropylene polymers and copolymers thereof, sodium salts of long chain alcohol sulfates, and fatty alcohol/fatty amide blends; fatty acids such as lauric, myristic, palmitic, oleic, and stearic acids; diethyl- and dipropylbenzoates; poly ethylene polymers and sodium
  • Textile materials treated with the finishing compositions of this invention exhibit the hand and wetting characteristics common to textile materials treated with conventional softeners; however, the addition of an aldehyde or acetal to t: textile finish enhances the durability of the textile finish a: provides for a soft hand and improved wetting characteristics even after repeated home launderings.
  • the presence of the aldehyde or acetal component with the silylated polyether results in improved dimensional stability properties of the textile material over those treated solely with an aldehyde.
  • the wetting characteristics and dimensional stability characteristics are determined in accordance with the test procedures described in the Technical Manual of the American Association of Textile Chemists and Colorists (AATCC), test methods 39-1980 and 135-1978, respectively.
  • the silylated polyether emulsion in Table I is prepared by heating a mixture containing 124 parts of succinic anhydride and 2,278 parts of oxyethylene-oxypropylene triol copolymer, having a molecular weight of 6360 and a'weight ratio of oxyethylene to oxypropylene of 7 to 3, for eighteen hours at 120°C.
  • the resultant product is a yellow liquid having a viscosity of 4,168 mPa.s at 25°C and an acid content of 0.58 milliequivalents per gram (theoretical 0.5 meq/g).
  • the resultant product is then mixed with 238 parts of aminopropyltriethoxysilane and heated at 70°C for 3 hours.
  • the product i-s a yellow liquid having a viscosity of about 30,000 mPa.s at 25°C.
  • the product is then mixed with 660 parts of a hydroxyl terminated polydimethylsiloxane having a viscosity of 60 mPa.s at 25°C and a hydroxyl content of about 2.5 percent and heated at 50°C for 6 hours.
  • a white, opaque fluid having a viscosity of about 60,000 mPa.s at 25°C is recovered.
  • This product is. combined with 6700 parts of water to form a white, opaque emulsion having a viscosity of 50 mPa.s at 25°C.
  • the silylated polyether in Table II is prepared by heating a mixture containing 150 parts of succinic anhydride and 2880 parts of oxyethylene-oxypropylene triol copolymer, having a molecular weight of 6360 and a weight ratio of oxyethylene to oxypropylene of 7 to 3, for eighteen hours at 120°C.
  • the product is a yellow liquid having a viscosity of 4,168 mPa.s at 25°C, and an acid content of 0.58 millie q uivalents per gram (theoretical 0.5 meq/g).
  • the resultant product is then mixed with 300 parts of, aminopropyltriethoxysilane and heated at 70°C for 2 hours.
  • the product is a yellow liquid having a viscosity of about 30,000 mPa.s at 25°C.
  • the resultant product is then mixed with 6670 parts of water to form a clear, straw-colored solution having a viscosity of 50 mPa.s at 25°C.
  • silylated polyethers used in the finishing compositions of Table III are prepared in the following manner:
  • the resultant product is an opaque, orange liquid having a viscosity of 275 mPa.s at 25°C.
  • About 300 parts of water are then added to form a yellow liquid having a viscosity of 25 mPa.s at 25°C and a base equivalent of 0.61 m eq/g (theoretical 0.4 meq/g).
  • the resultant composition has a 40 percent by weight solids content.
  • a silylated polyether is prepared by heating a mixture containing 1270 parts of an oxyethylene diol having a molecular weight of about 400 and 630 parts of succinic anhydride in a reaction vessel to 175°C. The vessel is cooled to 90°C and 1400 parts of aminopropyltriethoxysilane are added. After mixing for two hours, a clear amber liquid is obtained having a viscosity of 2116 mPa.s at 25°C.
  • A'silylated polyether is prepared by heating in a reaction vessel a mixture containing about 48 parts of succinic anhydride and 899 parts of an oxyethylene-oxypropylene triol copolymer having a molecular weight of 6360 and a weight ratio of oxyethylene to oxypropylene of 7 to 3, for eighteen hours at 120°C.
  • the resultant product is a yellow liquid having a viscosity of 4,165 mPa.s at 25°C and an acid content of 0.58 milliequivalents per gram (theoretical 0.5 meq/g).
  • the product is then mixed with 53 parts of aminoethyl- aminopropyltrimethoxysilane and heated at 70°C for three hours.
  • the resulting product is an amber liquid having a viscosity of 12,535 mPa.s at 25°C.
  • a silylated polyether is prepared by heating in a reaction vessel a mixture containing 800 parts of an amine having the general formula 264.7 parts of chloropropyltrimethoxysilane and 141.6 parts of triethylamine at 85°C for eight hours, and thereafter the resultant product is filtered through a celite mat. The filtrate is vacuum stripped to 100°C to form an orange liquid having a viscosity of 100 mPa.s at 25°C and a silicon content of 3.04 percent (theoretical 3.41 percent).
  • a silylated polyether is prepared by heating in a reaction vessel 300 parts of succinic anhydride and 2600 parts of an oxyethylene-oxypropylene copolymer, having a molecular weight of approximately 2600 and a weight ratio of oxyethylene to oxypropylene of 1.7 to 1, for eighteen hours at 120°C.
  • the resultant product is a yellow liquid having a viscosity of 1,698 mPa.s at 25°C and an acid content of 1.12 meq/g (theoretical 1.03 meq/g).
  • the above product is mixed with 664 parts of an aminopropyltriethoxysilane and heated at 70°C for three hours.
  • the resultant yellow liquid has a viscosity of 30,000 mPa.s at 25°C and a 33 percent by weight solids content.
  • This product is then combined with 7236 parts of water to form a clear, yellow solution having a viscosity of 18 mPa.s at 25°C.
  • a silylated polyether is prepared by heating in a reaction vessel 120 parts of succinic anhydride and 1000 parts of an oxyethylene-oxypropylene triol copolymer, having a molecular weight of 2600 and a weight ratio of oxyethylene to oxypropylene of 1.7 to 1 for eighteen hours at 120°C.
  • the resultant product is a clear, amber liquid having a viscosity of 1700 mPa.s at 25°C and an acid content of 1.12 milliequivalents per gram (theoretical 1.03 meq/g).
  • the above product is cooled to room temperature after which 238 parts of chloropropyltrimethoxysilane in 200 milliliters of xylene and 49.2 parts by weight of triethylamine are added and refluxed for 12 hours.
  • the resulting fluid is then filtered and the filtrate vacuum stripped to 90°C.
  • About 938 parts of water are immediately added to the residue and the resulting product is then cooled to room temperature.
  • the resultant amber colored liquid has a viscosity of 72.2 mPa.s at 25°C and a 60 percent by weight solids content.
  • a silylated polyether is prepared by heating 400 parts of oxypropylene diol, having a molecular weight of approximately 400, and 200 parts by weight of succinic anhydride at 120°C for eighteen hours in a reaction vessel. The resultant liquid is cooled to 70°C and then 238 parts of aminopropyltrimethoxysilane are added. After mixing at 70°C for two hours a clear, amber liquid having a viscosity of 1350 mPa.s at 25°C is obtained.
  • Three textile finishing baths are prepared by dispersing the ingredients listed in Table IV in water. These compositions are padded onto samples of polyester/cotton (65/35) fabric at 50 percent wet pick-up. The fabric is dried for 60 seconds at 120°C and cured for 20 seconds at 204°C. The treated fabric is then evaluated for (a) dimensional stability through five home launderings and (b) fabric hand. The results, in Table IV, show that textile finishes containing dimethoxymethane impart dimensional stability through five home launderings.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP83109682A 1982-09-30 1983-09-28 Agents de finissage pour textile Withdrawn EP0105464A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43189282A 1982-09-30 1982-09-30
US431892 1982-09-30

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EP0105464A2 true EP0105464A2 (fr) 1984-04-18
EP0105464A3 EP0105464A3 (fr) 1985-03-20

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Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4312993A (en) * 1979-09-10 1982-01-26 Sws Silicones Corporation Silylated polyethers
US4352917A (en) * 1980-09-18 1982-10-05 Sws Silicones Corporation Hydrophilic coatings for textile materials

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EP0105464A3 (fr) 1985-03-20
AU1417383A (en) 1984-04-05
JPS5982471A (ja) 1984-05-12

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