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US3238166A - Brocess for endowing permanent dirtpreventing property and hardness to fabrics of synthetic fibers, and resin composition therefor - Google Patents

Brocess for endowing permanent dirtpreventing property and hardness to fabrics of synthetic fibers, and resin composition therefor Download PDF

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US3238166A
US3238166A US22917162A US3238166A US 3238166 A US3238166 A US 3238166A US 22917162 A US22917162 A US 22917162A US 3238166 A US3238166 A US 3238166A
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fabrics
hardness
resin
permanent
aqueous solution
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Kawai Euchi
Matsumoto Tadao
Tajima Shigeru
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters 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
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
    • D06M15/333—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof of vinyl acetate; Polyvinylalcohol
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D06M2101/08—Esters or ethers of cellulose
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/26—Polymers or copolymers of unsaturated carboxylic acids or derivatives thereof
    • D06M2101/28—Acrylonitrile; Methacrylonitrile
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/04—Polyester fibers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric

Definitions

  • This invention relates to a process for imparting permanent and excellent hardness and soil resistance to fabrics of synthetic, hydrophobic fibers, particularly fabrics of polyester, polyacrylic, or partially acetylated cellulose fiber, or mixed spun fabrics thereof with cellulose or animal fibers, and to a resin composition therefor.
  • the present invention relates to a process for imparting permanent soil resistance and hardness to fabrics as mentioned above, by soaking the same in a resin bath containing an aqueous solution of a vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with acrolein or acrolein di- 3,238,166 Patented Mar. 1, 1966
  • fabrics of synthetic fibers are widely utilized as clothing because of their ease of washing and their excellent wrinkleor crease-resistance.
  • the most significant drawbacks of such fabrics reside in that it is difiicult to control the handling of fabric and that dirts tend to be adsorbed.
  • aqueous solution being added with magnesium chloride as catalyst, and then subjecting the fabrics to conventional resin processing procedures such as preliminary drying, curing, soaking, etc.
  • the present invention relates to a process for imparting more permanent soil resistance and hardness to such fabrics, by carrying out the above-mentioned process by combined use of at least one of other processing resin, such as dimethylolethyleneurea, dimethylolurone, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone, and their alkylated compounds.
  • other processing resin such as dimethylolethyleneurea, dimethylolurone, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone, and their alkylated compounds.
  • the present inventors have found, through broad researches on resins capable of yielding an excellent hardening effect to polyester, polyacrylonitrile and partially acetylated cellul'osic fiber fabrics, that such effect is easily obtained by employing a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponifying a copolymer of vinyl acetate with acrolein or with acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
  • catalyst employed in the aforesaid patents are maleic acid, glycolic acid and others.
  • the present inventors discovered after minute studies to find out a catalyst effective in applying said water soluble vinyl polymer to polyester, polyacrylonitrile and partially acetylated cellulosic fiber fabrics, that magnesium chloride can give surprisingly signficant hardness and soil resistance compared with other catalysts.
  • Table 2 shows the hardening effect obtained by using in combination with various catalyst a vinyl polymer resin A, prepared in accordance with the example described later.
  • the water soluble vinyl polymers employed in the present invention are those having the structure obtained, as mentioned before, by saponifying a copolymer of vinyl acetate with acrolein or acrolein diacetate, wherein X and Y are respectively whole numbers, and the ratio of X:Y is 5-20:9580.
  • the vinyl polymers particularly suitable to accomplish the object of the present invention are those containing acrolein units in an amount between about 5 and 20 mol percent, ordinarily about 10 mol percer'ai', on the basis of the vinyl polymer.
  • the vinyl polymers employed may be any of those having a molecular Weight of more than about 20,000 and less than about 1,000,000, and being water soluble. In case vinyl polymers having a molecular weight of less TABLE 2.HARDENING EFFECT OBTAINED BY TREATING PARTIALLY ACETYLATED CELLULOSIO FIBER FABRICS WITH A VINYL POLYMER RESIN A OF THE EXAMPLE IN COMBINATION WITH CAT- ALYSTS. (BEND LENGTH, MM.)
  • An object of the invention is to provide a novel process for imparting permanent soil resistance and hardness to fabrics of synthetic fibers, especially to fabrics of polyester, polyacrylic, and partially acetylated cellulose fibers, of which the improvement as shown above has not yet been attained.
  • Another object of the invention is to provide a resin composition used for the processing as abovementioned. Other objects would be apparent as the description proceeds.
  • the present invention provides a resin composition used for the processing of fabrics of hydrophobic fibers to endow them with permanent soil resistance and hardness, which comprises an aqueous solution of a vinyl polymer composed of vinyl alcohol and acrolein units, said aqueous solution containing magnesium chloride as catalyst. Further, the invention provides a process for imparting permanent soil resistance and hardness to fabrics of hydrophobic fibers, which comprises soaking a fabric of a hydrophobic fiber in a resin bath containing an aqueous solution of a vinyl polymer composed of vinyl alcohol and acrolein units, said aqueous solution containing magnesium chloride as catalyst.
  • the present invention provides a process for imparting permanent soil resistance and hardness to fabrics of synthetic, hydrophobic fibers, which comprises soaking a fabric containing at least partially a fiber of the group of polyester, polyacrylonitrile and partially acetylated cellulose fibers, in a resin bath containing an aqueous solution of a vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein or acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
  • the present invention provides a process for imparting permanent soil resistance and hardness to such fabrics, which comprises soaking the fabric in a resin bath containing an aqueous solution of such vinyl polymer and an aminoplast, said aqueous solution being added with magnesium chloride as catalyst.
  • Preferable magnesium chloride catalyst for the purpose of the present invention is prepared, for example, by adding more than about 15% of an aqueous 30% magnesium chloride solution to a 15% paste of said vinyl polymer.
  • the aminoplasts used in combination with the vinyl polymer for further increasing the permanent hardening and soil resistance are one or more of urea resins such as dimethylolurea, dimethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives.
  • urea resins such as dimethylolurea, dimethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives.
  • the available amounts of said urea resins added to the vinyl polymers are Within the range from about half the amount to 10 times the amount of the latter.
  • the fabric as above-identified is soaked in an aqueous solution containing the vinyl polymer and, if desired, the aminoplast, as above-mentioned, along with magnesium chloride, and then the soaked fabric is subjected to the conventional procedures which are known in the general resin-finishing processes.
  • the fabric issqueezed by means of rolls or a mangle, or by means of centrifugation, and then dried at a temperature below C.
  • the fabric is cured by heat-treatment at a temperature of to 200 0, preferably to C., for a few seconds to about 10 minutes, then washed with an alkaline solution to remove the residual acid in the fabric, and then dried.
  • the fabrics which are advantageously processed according to the invention include those of such synthetic hydrophobic fibers, as polyester, polyacrylic, and partially acetylated cellulose fibers.
  • the typical polyester is polyethylene terephthalate and its anologs.
  • the polyacrylic fibers include those made of acrylonitrile polymer and 5 copolymers containing a major part of acrylonitrile.
  • the partially acetylated cellulose fibers include those obtained from cellulose acetylated in various degree or those obtained by after-acetylation of cellulose fibers.
  • resin C This paste was referred to as resin C.
  • Resin baths Resins Dimethoxy- Dimethylol Dimethylol 30% mag- (part) methyluron ethyleneurea glyoxal mononesium (part of 50% (part of 50% ureine (part chloride Resin A aq. sol.) aq. sol.) of 50%)aq. (part) Resin B Resin Norm-The volume of each bath was made 100 cc. by addition of water.
  • Vinyl polymers were obtained according to the following processes:
  • Resin B To a mixture comprising 150 parts of vinyl acetate, 54 parts of acrolein diacetate, and 44 parts of methanol, there was added 0.2 part of benzoyl peroxide. After 48 hours polymerization under stirring at 60 C., the reaction mass was mixed with 750 parts of methanol and parts of caustic soda and saponified for 2 hours at 40 C. The resulting white powdery resin (molecular weight: 73,000) was separated and dissolved in water to yield a paste. This paste was referred to as resin B.
  • Resin C To a mixture comprising 13 parts of acrolein, 237 parts of vinyl acetate and 62 parts of methanol, there was added 7.5 parts of a,a-azobisisobutyr-onitrile, and the mixture was allowed to polymerize with agitation at 60 C. for hours. The resulting polymerizate was Subsequently, partially after-acetylated cellulose fiber fabrics muslin and a mix-spun
  • the P.V.A. bath was prepared by dissolving 1.5 parts of polyvinyl alcohol to make the volume of the resulting solution 100 cc.
  • Each dirt test was carried out by putting a test cloth (5 cm. x 5 cm.) in a Launder-O-meter containing the following dirtying bath at a bath ratio of 1:50, taking out the cloth after one minntes operation, washing the cloth with water, drying, and then judging the dirting degree by naked eyes.
  • the dirtying bath was prepared by dissolving in 250 cc. of carbon tetrachloride, 1 g. of carbon black, 0.5 g. of beef tallow and 2 g. of liquid parafiin.
  • the bath shown in the table was prepared by dissolving 5 parts of this resin paste and 0.5 part of 2-amino-2-methylpropanol hydrochloride in water to make the volume of the resulting solution 100 cc.
  • the P.V.A. bath was prepared by dissolving 1.5 parts of polyvinyl alcohol to make the volume of the resulting solution 100 cc.
  • a resin composition used for the processing of fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers to endow them with permanent soil resistance and hardness, which consists essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponi-"fication of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said aqueous solution containing magnesium chloride as catalyst.
  • a resin composition used for the processing of fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers to endow them with permanent soil resistance and hardness, which consists essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said aqueous solution containing magnesium chloride as catalyst and at least one aminoplast selected from the group consisting of dimethylolurea, dirnethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives.
  • a process for imparting permanent soil resistance and hardness to fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers, which comprises soaking said fabric in a resin bath consisting essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and a aldehyde groups in the molecule, which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acroiein and acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
  • a process for imparting permanent soil resistance and hardness to fabrics comprising fibers selected from the group consisting of polyester, polyarcylic and partially acetylated cellulosic fibers, which comprises soaking said fabric in a resin bath consisting essentially of an aqueous solution of a water soluble vinyl polymer and at least one aminoplast, said vinyl polymer containing hydroxyl and aldehyde groups in the molecule, which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said amino-plast being a member selected from the group consisting of dimethylolurea, dimethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives, and said aqueous solution being added with magnesium chloride as catalyst.

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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)

Description

United States Patent O 3,238,166 ITQOCESS FOR ENDOWING PERMANENT DIRT- .PREVENTING PROPERTY AND HARDNESS T FABRICS 0F SYNTHETIC FIBERS, AND RESIN COMPOSITION THEREFOR Eiichi Kawai, Takatsnki-shi, Tadao Matsumoto, Toyonaka-shi, and Shigeru Tajima, Ashiya-shi, Japan, assignors to Sumitomo Chemical Company, Ltd., Osaka, Japan, a corporation of Japan No Drawing. Filed Oct. 8, 1962, Ser. No. 229,171 Claims priority, application Japan, Oct. 10, 1961, 36/36,747 4 Claims. (Cl. 260-2941) This invention relates to a process for imparting permanent and excellent hardness and soil resistance to fabrics of synthetic, hydrophobic fibers, particularly fabrics of polyester, polyacrylic, or partially acetylated cellulose fiber, or mixed spun fabrics thereof with cellulose or animal fibers, and to a resin composition therefor.
More particularly, the present invention relates to a process for imparting permanent soil resistance and hardness to fabrics as mentioned above, by soaking the same in a resin bath containing an aqueous solution of a vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with acrolein or acrolein di- 3,238,166 Patented Mar. 1, 1966 At present, fabrics of synthetic fibers are widely utilized as clothing because of their ease of washing and their excellent wrinkleor crease-resistance. However, the most significant drawbacks of such fabrics reside in that it is difiicult to control the handling of fabric and that dirts tend to be adsorbed. Because of their ease of washing, which is one of the characteristics of the fabrics of synthetic fibers, they have been utilized mainly for those clothings which are laundered repeatedly, such as white shirts, blouses and sport shirts. Therefore, an indispensable requirement for synthetic fabric involves permanent improvement in handling and dirt-resistance. These improvements have been sought by those in the trade. Regarding polyamide and polyvinyl fiber fabrics, such improvements have recently been almost achieved. Regarding polyester, polyacryl'ic and partially acetylated cellulosic fiber fabrics, however, no satisfactory improvement has yet been obtained.
That is to say, fabrics of polyamide and polyvinyl fibers, have been treated, as in the case of cellulose fiber fabrics, with arninoplast, particularly with melamine resin, to obtain a durable, strong hardness. Polyester, polyacrylic and partially acetylated cellulosic fiber fabrics, however, have less aflinity to such resins, hence, it is difficult to obtain permanent hardness by bondage of such resins, as shown in Table 1.
TABLE 1.EFFECTS OF HARDENING AGENTS TO VARIOUS FABRICS Treated with a highly Treated with a methyl- Non-treated condensed urea.- ated trimethylol- Treated with P.V.A.
formaldehyde resin 1 melamine 8 Before After Before After Before After Before After washing washing 5 washing washing washing washing washing washing 40s cotton broad cloth 83 78 115 105 90 88 132 87 Sheer nylon 57 89 80 107 103 87 60 Sheet polyethylene terephthalate 77 81 101 86 129 91 102 83 Polyacrylonitrile fiber fabric muslin. 45 46 53 98 68 50 Partially after-acetylated cellulosic-fiber fabric tropical 66 60 125 65 153 110 60 weft directions (mm).
1 The effect of each hardening agent is determined by measuring the bending lengths and summing up the values of warp and (OCC-T-191b method No. 5206) 2 The resin was applied to the respective fabrics according to the following recipe:
A highly condensed urea-formaldehyde resinl0 g. Accelerator ACX(2-amino-2-methylpr0panol hydr0chloride)-l g. Total amount was made cc. by addition of water.
i The methylated trimethylolmelamine was applied to the respective fabrics according to the following recipe:
A methylated trimethylol amine-10 g. Accelerator ACX-1 g. Total amount was made 100 cc. by addition of water. 4 P.V.A. is a 2% aqueous solution of polyvinyl alcohol. 5 Respective washing was repeated 5 times by h0me-washing machine.
acetate, said aqueous solution being added with magnesium chloride as catalyst, and then subjecting the fabrics to conventional resin processing procedures such as preliminary drying, curing, soaking, etc.
Further, the present invention relates to a process for imparting more permanent soil resistance and hardness to such fabrics, by carrying out the above-mentioned process by combined use of at least one of other processing resin, such as dimethylolethyleneurea, dimethylolurone, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone, and their alkylated compounds.
The present inventors have found, through broad researches on resins capable of yielding an excellent hardening effect to polyester, polyacrylonitrile and partially acetylated cellul'osic fiber fabrics, that such effect is easily obtained by employing a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponifying a copolymer of vinyl acetate with acrolein or with acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
Methods for producing the above-mentioned watersoluble vinyl polymer are well known from the description in United States Patent Nos. 2,569,932, 2,485,239 and 2,657,192. Also, these patents describe that said water soluble vinyl polymer may be employed as an adhesive for cellophanes, paper or clothes or a sizing agent for nylon fabrics. However, there was no disclosure that such vinyl polymer can advantageously be utilized in imparting permanent hardness and soil resistance effect to specific textile fabrics.
Moreover, catalyst employed in the aforesaid patents are maleic acid, glycolic acid and others. The present inventors, however, discovered after minute studies to find out a catalyst effective in applying said water soluble vinyl polymer to polyester, polyacrylonitrile and partially acetylated cellulosic fiber fabrics, that magnesium chloride can give surprisingly signficant hardness and soil resistance compared with other catalysts.
Table 2 shows the hardening effect obtained by using in combination with various catalyst a vinyl polymer resin A, prepared in accordance with the example described later.
The water soluble vinyl polymers employed in the present invention are those having the structure obtained, as mentioned before, by saponifying a copolymer of vinyl acetate with acrolein or acrolein diacetate, wherein X and Y are respectively whole numbers, and the ratio of X:Y is 5-20:9580.
Thus, the vinyl polymers particularly suitable to accomplish the object of the present invention are those containing acrolein units in an amount between about 5 and 20 mol percent, ordinarily about 10 mol percer'ai', on the basis of the vinyl polymer.
Also, the vinyl polymers employed may be any of those having a molecular Weight of more than about 20,000 and less than about 1,000,000, and being water soluble. In case vinyl polymers having a molecular weight of less TABLE 2.HARDENING EFFECT OBTAINED BY TREATING PARTIALLY ACETYLATED CELLULOSIO FIBER FABRICS WITH A VINYL POLYMER RESIN A OF THE EXAMPLE IN COMBINATION WITH CAT- ALYSTS. (BEND LENGTH, MM.)
2-amino- MgCh-i- Catalyst N ontreated Malelc (N11 HPO; Z-methyl Zn(N0 MgCl, dimethylolcloth acid propanol uron hydrochloride Beforewash ing 62 92 9O 98 93 114 120 After washing r. 71 68 81 77 100 112 An object of the invention is to provide a novel process for imparting permanent soil resistance and hardness to fabrics of synthetic fibers, especially to fabrics of polyester, polyacrylic, and partially acetylated cellulose fibers, of which the improvement as shown above has not yet been attained. Another object of the invention is to provide a resin composition used for the processing as abovementioned. Other objects would be apparent as the description proceeds.
Accordingly, the present invention provides a resin composition used for the processing of fabrics of hydrophobic fibers to endow them with permanent soil resistance and hardness, which comprises an aqueous solution of a vinyl polymer composed of vinyl alcohol and acrolein units, said aqueous solution containing magnesium chloride as catalyst. Further, the invention provides a process for imparting permanent soil resistance and hardness to fabrics of hydrophobic fibers, which comprises soaking a fabric of a hydrophobic fiber in a resin bath containing an aqueous solution of a vinyl polymer composed of vinyl alcohol and acrolein units, said aqueous solution containing magnesium chloride as catalyst. More particularly, the present invention provides a process for imparting permanent soil resistance and hardness to fabrics of synthetic, hydrophobic fibers, which comprises soaking a fabric containing at least partially a fiber of the group of polyester, polyacrylonitrile and partially acetylated cellulose fibers, in a resin bath containing an aqueous solution of a vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein or acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
Furthermore, the present invention provides a process for imparting permanent soil resistance and hardness to such fabrics, which comprises soaking the fabric in a resin bath containing an aqueous solution of such vinyl polymer and an aminoplast, said aqueous solution being added with magnesium chloride as catalyst.
than such limitation are employed, the desired object of the present invention is hardly achieved.
Preferable magnesium chloride catalyst for the purpose of the present invention is prepared, for example, by adding more than about 15% of an aqueous 30% magnesium chloride solution to a 15% paste of said vinyl polymer.
The aminoplasts used in combination with the vinyl polymer for further increasing the permanent hardening and soil resistance are one or more of urea resins such as dimethylolurea, dimethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives. The available amounts of said urea resins added to the vinyl polymers are Within the range from about half the amount to 10 times the amount of the latter.
In case other aminoplasts, such as melamine resins, are employed, no permanent hardening effect is obtained through such effect is displayed at the initial stage, and therefore it is hardly possible to attain the object of the present invention.
In carrying out the process of the present invention, the fabric as above-identified is soaked in an aqueous solution containing the vinyl polymer and, if desired, the aminoplast, as above-mentioned, along with magnesium chloride, and then the soaked fabric is subjected to the conventional procedures which are known in the general resin-finishing processes. For example, the fabric issqueezed by means of rolls or a mangle, or by means of centrifugation, and then dried at a temperature below C. Thereafter the fabric is cured by heat-treatment at a temperature of to 200 0, preferably to C., for a few seconds to about 10 minutes, then washed with an alkaline solution to remove the residual acid in the fabric, and then dried.
The fabrics which are advantageously processed according to the invention include those of such synthetic hydrophobic fibers, as polyester, polyacrylic, and partially acetylated cellulose fibers. The typical polyester is polyethylene terephthalate and its anologs. The polyacrylic fibers include those made of acrylonitrile polymer and 5 copolymers containing a major part of acrylonitrile. The partially acetylated cellulose fibers include those obtained from cellulose acetylated in various degree or those obtained by after-acetylation of cellulose fibers.
In the following, the present invention will be illustrated with reference to examples.
6 subjected to the same saponification as in the case of resin B to obtain a resin (molecular weight: about 22,000), which was then dissolved in water to form a 15% paste. This paste was referred to as resin C.
By use of said resins A, B and C, the following 12 kinds of resin baths were prepared:
Components Resin baths Resins Dimethoxy- Dimethylol Dimethylol 30% mag- (part) methyluron ethyleneurea glyoxal mononesium (part of 50% (part of 50% ureine (part chloride Resin A aq. sol.) aq. sol.) of 50%)aq. (part) Resin B Resin Norm-The volume of each bath was made 100 cc. by addition of water.
Vinyl polymers were obtained according to the following processes:
Resin A 172 parts of vinyl acetate and 32 parts of acrolein diacetate were dispersed in 320 parts of water together with 0.1 part of polyvinyl alcohol (a dispersing agent). To the resulting dispersion, 0.2 part of benzoyl peroxide was added, and the mixture was allowed to polymerize for 5 hours at 70 C. The granular polymer yielded was separated, dried and then dissolved in methanol so as to form a 20% solution. 18 parts of caustic soda was added to the solution and the saponification was effected for 2 hours at 35 C. The precipitated white powdery resin (molecular weight: about 200,000) was separated from the methanol by filtration and then dissolved in water to form a 15% paste. This paste was referred to as resin A.
Resin B To a mixture comprising 150 parts of vinyl acetate, 54 parts of acrolein diacetate, and 44 parts of methanol, there was added 0.2 part of benzoyl peroxide. After 48 hours polymerization under stirring at 60 C., the reaction mass was mixed with 750 parts of methanol and parts of caustic soda and saponified for 2 hours at 40 C. The resulting white powdery resin (molecular weight: 73,000) was separated and dissolved in water to yield a paste. This paste was referred to as resin B.
Resin C To a mixture comprising 13 parts of acrolein, 237 parts of vinyl acetate and 62 parts of methanol, there was added 7.5 parts of a,a-azobisisobutyr-onitrile, and the mixture was allowed to polymerize with agitation at 60 C. for hours. The resulting polymerizate was Subsequently, partially after-acetylated cellulose fiber fabrics muslin and a mix-spun |broad of polyethylene terephthalate fibers and cotton were immersed in each of these baths, squeezed by means of a mangle, dried at C. for 2 minutes, heat-treated at 140 C. for 4 rhinutes, washed with an alkaline cleanser and then dried.
The hardening and soil resistance were as shown in the following tables.
TABLE 3.RESULTS OF TESTS WITH PARTIALLY ACETYLATED CELLULOSE MUSLIN 2 The bath shown in the table was prepared by dissolving 5 parts of this resin paste and 0.5 part of 30% 2-amino-2-1nethylpropanol hydrochloride in water to make the volume of the resulting solution cc.
3 The P.V.A. bath was prepared by dissolving 1.5 parts of polyvinyl alcohol to make the volume of the resulting solution 100 cc.
TABLE 4.RESULTS OF TESTS WITH A MIX-SPUN FABRIC OF A POLYETHYLENE TEREPHTHALATE FIBER WITH COTTON Bending Bending Dirt test (naked eyes) Dirt test 1 (brightness) length before length after Processing washing washing (warp and (warp and Before After Before After weft) (mm) weft) (1pm.) washing 2 washing 2 washing 2 washing 2 Non-processed cloth 76 35 34 Resin bath:
A-.. 100 61 53 A-l- 121 64 58 A2 110 55 49 A-3. 118 59 54 B 98 59 51 13-1- 111 61 56 B-2 107 55 49 B- 112 59 52 C 58 50 C-1. 109 59 55 C- 102 54 50 C- 107 59 51 A methylated 90 43 37 methylolmelarnine paste. P.V.A. 89 42 36 1 The brightness was determined by measurement of reflexing ratio at 550 m based upon magnesium oxide white, by use of Recording Spectrophotometer made by General Electric Co.
2 Each dirt test was carried out by putting a test cloth (5 cm. x 5 cm.) in a Launder-O-meter containing the following dirtying bath at a bath ratio of 1:50, taking out the cloth after one minntes operation, washing the cloth with water, drying, and then judging the dirting degree by naked eyes. The dirtying bath was prepared by dissolving in 250 cc. of carbon tetrachloride, 1 g. of carbon black, 0.5 g. of beef tallow and 2 g. of liquid parafiin.
3 The bath shown in the table was prepared by dissolving 5 parts of this resin paste and 0.5 part of 2-amino-2-methylpropanol hydrochloride in water to make the volume of the resulting solution 100 cc.
4 The P.V.A. bath was prepared by dissolving 1.5 parts of polyvinyl alcohol to make the volume of the resulting solution 100 cc.
0scareely made dirty. Asomewhat made dirty. X-rnade dirty. Furthermore, the etfectivenesses of the combined use of the various aminoplasts according to the invention are set forth in the following Table 5.
TABLE 5.EFFECTIVENESSES OF THE COMBINED USE OF VARIOUS AMINOPLASTS (A MIXED SPUN POLYETHYL- ENE TEREPHTHALATECOTTON BROADCLOTH).
What we claim is:
1. A resin composition used for the processing of fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers to endow them with permanent soil resistance and hardness, which consists essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponi-"fication of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said aqueous solution containing magnesium chloride as catalyst.
2. A resin composition used for the processing of fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers to endow them with permanent soil resistance and hardness, which consists essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and aldehyde groups in the molecule which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said aqueous solution containing magnesium chloride as catalyst and at least one aminoplast selected from the group consisting of dimethylolurea, dirnethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives.
3. A process for imparting permanent soil resistance and hardness to fabrics comprising fibers selected from the group consisting of polyester, polyacrylic and partially acetylated cellulosic fibers, which comprises soaking said fabric in a resin bath consisting essentially of an aqueous solution of a water soluble vinyl polymer containing hydroxyl and a aldehyde groups in the molecule, which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acroiein and acrolein diacetate, said aqueous solution being added with magnesium chloride as catalyst.
4. A process for imparting permanent soil resistance and hardness to fabrics comprising fibers selected from the group consisting of polyester, polyarcylic and partially acetylated cellulosic fibers, which comprises soaking said fabric in a resin bath consisting essentially of an aqueous solution of a water soluble vinyl polymer and at least one aminoplast, said vinyl polymer containing hydroxyl and aldehyde groups in the molecule, which is obtained by saponification of a copolymer of vinyl acetate with a member selected from the group consisting of acrolein and acrolein diacetate, said amino-plast being a member selected from the group consisting of dimethylolurea, dimethylolethyleneurea, dimethyloluron, dimethylolglyoxalmonourein, tetramethylolacetylenediurea, dimethyloltriazone and their alkylated derivatives, and said aqueous solution being added with magnesium chloride as catalyst.
References Cited by the Examiner UNITED STATES PATENTS 2,485,239 10/1949 Izard 260-73 2,569,932 10/1951 Izard 26073 2,950,553 8/1960 Hur-Witz 117-143 3,149,999 9/1964 Enders et a1. 1l7161 MURRAY TILLMAN, Primary Examiner.
JAMES A. SEIDLECK, Examiner.
E. I. TROJNAR, J. C. BLEUTGE, Assistant Examiners.

Claims (1)

  1. 2. A RESIN COMPOSITION USED FOR THE PROCESSING OF FABRICS COMPRISING FIBERS SELECTED FROM THE GROUP CONSISTING OF POLYESTER, POLYACRYLIC AND PARTIALLY ACETYLATED CELLULOSIC FIBERS TO ENDOW THEM WITH PERMANENT SOIL RESISTANCE AND HARDNESS, WHICH CONSISTS ESSENTIALLY OF AN AQUEOUS SOLUTION OF A WATER SOLUBLE VINYL POLYMER CONTAINING HYDROXYL AND ALDEHYDE GROUPS IN THE MOLECULE WHICH IS OBTAINED BY SAPONIFICATION OF A COPOLYMER OF VINYL ACETATE WITH A MEMBER SELECTED FROM THE GROUP CONSISTING OF ACROLEIN AND ACROLEIN DIACETATE, SAID AQUEOUS SOLUTION CONTAINING MAGNESIUM CHLORIDE AS CATALYST AND AT LEAST ONE AMINOPLAST SELECTED FROM THE GROUP CONSISTING OF DIMETHYLOLUREA, DIMETHYLOLETHYLENEUREA, DIMETHYLOLURON, DIMETHYLOGLYOXALMONOUREIN, TETRAMETHYLOLACETYLENEDIUREA, DIMETHYLOLTRIAZONE AND THEIR ALKYLATED DERIVATIVES.
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US3833397A (en) * 1970-05-04 1974-09-03 Sandoz Ltd Process for the resin finishing of cellulosic fabrics and cellulosic blend fabrics with simultaneous improvement of their affinity for optical brighteners
US4314805A (en) * 1979-10-29 1982-02-09 Mcknight Eugene A Laundry process and method for treating textiles

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Publication number Priority date Publication date Assignee Title
US5407728A (en) 1992-01-30 1995-04-18 Reeves Brothers, Inc. Fabric containing graft polymer thereon
US5486210A (en) 1992-01-30 1996-01-23 Reeves Brothers, Inc. Air bag fabric containing graft polymer thereon

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US2485239A (en) * 1945-03-06 1949-10-18 Du Pont Polymers containing recurring aldehyde groups and derivatives thereof and process for preparing same
US2569932A (en) * 1945-11-21 1951-10-02 Du Pont Cross-linked hydrolyzed interpolymer of vinyl acetate and allylidene diacetate and process
US2950553A (en) * 1957-01-16 1960-08-30 Rohm & Haas Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics
US3149999A (en) * 1960-09-22 1964-09-22 Pfersee Chem Fab Process for treating textiles

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Publication number Priority date Publication date Assignee Title
US2485239A (en) * 1945-03-06 1949-10-18 Du Pont Polymers containing recurring aldehyde groups and derivatives thereof and process for preparing same
US2569932A (en) * 1945-11-21 1951-10-02 Du Pont Cross-linked hydrolyzed interpolymer of vinyl acetate and allylidene diacetate and process
US2950553A (en) * 1957-01-16 1960-08-30 Rohm & Haas Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics
US3149999A (en) * 1960-09-22 1964-09-22 Pfersee Chem Fab Process for treating textiles

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3833397A (en) * 1970-05-04 1974-09-03 Sandoz Ltd Process for the resin finishing of cellulosic fabrics and cellulosic blend fabrics with simultaneous improvement of their affinity for optical brighteners
US4314805A (en) * 1979-10-29 1982-02-09 Mcknight Eugene A Laundry process and method for treating textiles

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