US3123496A - Process for the finishing of textile - Google Patents

Process for the finishing of textile Download PDF

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US3123496A
US3123496A US3123496DA US3123496A US 3123496 A US3123496 A US 3123496A US 3123496D A US3123496D A US 3123496DA US 3123496 A US3123496 A US 3123496A
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parts
acid
vinyl
dispersion
fabric
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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
    • D06M15/263—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
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31725—Of polyamide
    • Y10T428/3175—Next to addition polymer from unsaturated monomer[s]
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic
    • Y10T428/31895—Paper or wood
    • Y10T428/31906—Ester, halide or nitrile of addition polymer
    • 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
    • Y10T442/2164—Coating or impregnation specified as water repellent
    • Y10T442/2172—Also specified as oil repellent
    • 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
    • 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
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • acyl urethanes in the copolymer used in the present invention can vary within wide limits. In general, there are used quantities of about 0.5 to 90 parts by weight, preferably about 2 to 20 parts by weight, of acyl urethanes per 100 parts by weight of copolymer.
  • acyl urethanes there are used compounds of the general formula in which R-CO represents the radical of a monobasic or polybasic carboxylic acid which is unsaturated in one or several positions and which, in the case of a polybasic carboxylic acid, may additionally be esterified with aliphatic alcohols of low molecular weight containing 1-6 carbon atoms, or the carboxyl groups of which may be substituted by the carbamic acid ester radical X stands for oxygen or sulfur, and R stands for a low molecular weight alkyl, cycloalkyl, aryl or aralkyl radical which, if desired, may be substituted, in particular by alkoxy radicals.
  • R-CO represents the radical of a monobasic or polybasic carboxylic acid which is unsaturated in one or several positions and which, in the case of a polybasic carboxylic acid, may additionally be esterified with aliphatic alcohols of low molecular weight containing 1-6 carbon atoms, or the carb
  • the group RCO there enters into consideration preferably the radical of a mono or dibasic carboxylic acid containing up to 6 carbon atoms and one As such, there are mentioned by way of example: acrylic acid,methacrylic acid, crotonic acid, itaconic acid,-citraconic acid, mesaconic acid, muconic acid, maleic acid, aconitic acid, etc. Mixtures of the acyl-urethanes may also be used.
  • acylurethanes of the above-indicated formula when compounds are used in which R means a cycloalkyl or an alkyl radical containing up to 6 carbon atoms, which radical maybe substituted by methoxy or ethoxy radicals, for example the methyl, ethyl, isopropyl, butyl, isobutyl, n-hexyl, isohexyl, or also the ,B-methoxyethyl radical.
  • N-acryloyl carbamic acid-butyl ester N-acryloyl carbamic acid isopropyl ester
  • compounds that contain vinyl groups and that may be used' for the copolymerization with the unsaturated acyl urethanes there are suitable compounds which con tain one or several polymerizable ethylene double linkages as for example: the unsaturated alcohol esters more particularly the allyl, methallyl, crotyl, vinyl, propargyl, etc., esters of saturated and unsaturated, aliphatic and aromatic, monobasic and polybasic acids such as, for example, acetic, propionic, butyric, acrylic and alpha-substituted acrylic (including alkacrylic, e.g.
  • methacrylic etc. methacrylic etc.,) crotonic, malonic, adipic, maleic, citraconic, itaconic, acetylene dicarboxylic, phthalic, etc., acids; the saturated monohydric alcohol esters, e.g. the methyl, ethyl, propyl, isopropyl, butyl, sec.-butyl, amyl, etc., esters of unsaturated aliphatic mono-basic acids and polybasic acids; vinyl cyclic compounds (including monovinyl aromatic hydrocarbons), e.g.
  • styrene o-, mand p-chlorostyrenes, o-, mand pmethylstyrenes
  • the various poly-substituted styrenes such, for example, as vinyl cyclohexane, vinyl pyridine, divinyl benzene, allyl benzene, the various allyl cyanostyrenes, the various alpha-substituted styrenes and alphasubstituted ring-substituted styrenes, e.g., alpha-methyl styrene, alpha-methyl-para-methyl styrene, etc.; unsaturated ethers, e.g., ethylvinyl ether, diallyl ether, ethyl methallyl ether, etc.; unsaturated amides, e.g., acrylamide, and N-substituted acrylamides, e.g
  • N-methylol acrylamide, N-methyl acrylamide, etc. unsaturated ketones, e.g. methyl vinyl ketone, methyl allyl ketone, etc.; butadienes, e.g. 1,3-butadiene, Z-chlorobutadiene, etc.; unsaturated polyhydric alcohol (e.g., butenediol, etc.); esters of saturated and unsaturated, aliphatic and aromatic, monobasic aud polybasic acids.
  • acyl urethanes examples include the vinyl halides, more particularly vinyl chloride, and the various vinylidene compounds, including the vinylidene halides, e.g., vinylidene chloride.
  • the vinyl compounds may be copolymerized in the form of solution, bulk, emulsion or dispersion polymers, individually or in admixture with the acyl urethanes, according to a mechanism which uses for the polymerization either the relations between the radicals or ionic relations.
  • the following monomers that contain vinyl groups can be used with special advantage: the vinyl esters of ali phatic, low molecular carboxylic acids containing 1 to 4 carbon atoms, e.g. vinyl acetate and vinyl propionate, vinyl ethers of aliphatic low molecular alcohols containing l-6 Water or in inert organic solvents, for example in hydrocanbons such as benzine, benzene, toluene, or in liquid aliphatic chlorinated hydrocarbons of low molecular Weight, for example methylene chloride, carbon tetrachloride, trichlorethylene, ethylene chloride, tetrachlorethane, etc., or as aqueous dispersions or emulsions.
  • the vinyl esters of ali phatic, low molecular carboxylic acids containing 1 to 4 carbon atoms e.g. vinyl acetate and vinyl propionate
  • the textile material treated with these copolymers, if desired together with other known finishing or auxiliary agents, is then dried at an elevated temperature in order to be fixed. Temperatures higher than 60 C. to about 180 C. are suitable for this purpose, temperatures in the range of about 100-150 C., being preferred.
  • the heating periods required may vary within Wide limits. Above all, they depend on the temperatures applied. At more elevated drying temperatures of about l30180 C., a heating period of only a few minutes is sufiicient in order to produce good wash-fast finishes. In practice, drying periods of about 1 to about 30 minutes are applied. These periods are approximate data only. In special cases the periods may be longer or shoiter.
  • copolymers of the present invention there can be produced, for example, wash-fast filling or sizing finishes, embossing finishes, and finishes that are waterrepellent, oil-repellent, dirt-repellent or resistant to swelling and creasing.
  • wash-fiastness of these finishes can often be increased by adding potential acid donators such as the ammonium salts of strong acids, for example ammonium chloride and ammonium nitrate, salts of bivalent metals with strong acids, for example magnesium chloride, zinc chloride or zinc nitrate. It is, however, also possible to apply the copolymers in an alkaline medium whereby very favorable results are likewise obtained.
  • potential acid donators such as the ammonium salts of strong acids, for example ammonium chloride and ammonium nitrate, salts of bivalent metals with strong acids, for example magnesium chloride, zinc chloride or zinc nitrate.
  • the copolymers may also be used together with anionic, non-ionogenic or cationic agents that are conventionally used in the textile industry, for example, softening agents, emulsifying agents, pigments, hydrophobizing agents, insecticides, fungicides, or high quality finishes, for example anti-swelling and anti-creasing agents.
  • anionic, non-ionogenic or cationic agents that are conventionally used in the textile industry, for example, softening agents, emulsifying agents, pigments, hydrophobizing agents, insecticides, fungicides, or high quality finishes, for example anti-swelling and anti-creasing agents.
  • finishing agents that may be used simultaneously, there are mentioned by way of example: urea precondensates or melamine-formaldehyde precondensates, methylol compounds of cyclic urea derivatives, tri-azinones, and the like, further also precondensates of epoxide resins etc.
  • Other two-dimensional structures of fibrous nature for example, paper, felt, etc. are likewise suitable.
  • Example 1 315 parts of a solution of 5% strength of a polyvinyl alcohol having a K-value of 50 were introduced into a four-neck flask provided with thermometer, stirrer, reflux cooler, and a dropping funnel. In this solution was then dispersed to obtain an emulsion, with intensive stirring and at room temperature, a solution of 9 parts of N- acryloyl-carbamic acid-butyl ester in 300 parts of vinyl acetate. The pH was adjusted to 3 by means of formic acid, and 2.2 parts of hydrogen peroxide of 33% strength were added as activator.
  • the mixture was heated to the boiling point of the azeotrope of vinyl acetate and water (66 C.) and after beginning of the polymerization the mixture was kept for 4 hours at this temperature. There was obtained a dispersion of polymeric material having a residual content of monomers of less than 0.7%.
  • a fabric from polyester fibers was immersed into a solution containing per liter 60 grams of the above-mentioned dispersion, then centrifuged to about 80% of residual moisture and dried at 90 C. After 3 washes in a house-hold washing machine withthe usual quantity of coarse detergent, the fabric had a residual stiffness in bend of 42% of its stiffness prior to the Washing.
  • Example 2 In the apparatus described in Example 1 was introduced the following polymerization mixture:
  • the pH was adjusted to 5-6 by means of acetic acid. This mixture was then heated on a water bath having 80 C. and a solution of 6 parts of N-acryloyl-carbamic acid-butyl ester in 54 parts of vinyl acetate is dropwise added during 15 minutes so as to obtain an emulsion, and then a solution of 3 parts of sodium persulfate in 50 parts of water is added dropwise. After the polymerization had started, a residual mixture of monomer consisting of 54 parts of N-acryloyl-carbamic acid-butyl ester and 480 parts of vinyl acetate was added within 1 hour and at a temperature of the reaction mixture of 80 C. The polymerization was terminated after a further 1 /2 hours. There was obtained a very fine dispersion which had a low viscosity.
  • a piece of cotton shirt poplin treated with lye was padded with a solution containing per liter 100 grams of this dispersion, squeezed on a padding mangle, and dried at C. After 10 washes at boiling temperatures, a residual stiffness in bend of 79% was still present, whereas a piece of cotton shirt poplin that had been padded with a solution containing per liter grams of the dispersion prepared according to the above prescription, however without addition of acyl urethane, exhibited after the same treatment and the same number of washes a residual stiffness in bend of 47% only.
  • the coating obtained was transparent.
  • the water-repellency of the coating produced with the dispersion containing acyl urethane was substantially better than that of a coating prepared with a pure polyvinyl acetate dispersion.
  • Example 3 Into the apparatus described in Example 1 was introduced a bath of the following composition:
  • the pH was adjusted to 3 by means of formic acid, and the whole was heated to 80 C.; into this mixture was dispersed so as to obtain an emulsion, a solution of 5 grams of N-crotonyl carbamic acid-[fl-methoxyethyl ester] in 45 grams of vinyl acetate. 1.1 parts of hydrogen peroxide of 30% strength were then added dropwise. After the polymerization had started, a solution of 45 parts of N-crotonyl-carbamic acid [ti-methoxyethyl ester] in 405 parts of vinyl acetate was added dropwise during 2 hours, while keeping the reaction temperature at 80 C. After a further 4 hours, the polymerization was terminated. There was obtained a dispersion having medium viscosity and a residual content of monomers of less than 1%.
  • a fabric of mercerized cotton shirt poplin was impregnated on a padding machine with a bath' containing per liter 100 grains of the above dispersion, and, in addition thereto, per liter 15 grams of dimethylol-ethylene urea and 10 grams of magnesium chloride; the fabric was then predried at 60 C. and after-heated for 5 minutes to 150 C.
  • the crease recovery test in the moist state exhibited a crease angle of 213 and after 10 washes at boiling temperatures an angle of 252.
  • Example 4 To a dyebath containing per liter 100 grams of the dispersion described in Example 2 there were added per liter grams of magnesium chloride. A fabric of viscose staple fibers was padded with this bath, dried at 100 C., and after-dried for 5 minutes at 140 C. For comparison, a similar fabric was finished in the same manner with a dispersion that contained an equal quantity of pure polyvinyl acetate together with magnesium chloride. In the wet state, the last-mentioned fabric exhibited a crease recovery of 77% of that of the first-mentioned fabric. After 10 washes at boiling temperatures, the crease recovery of the fabric that had been finished with the pure polyvinyl acetate dispersion was still 85% of that of the fabric finished with the dispersion containing acyl urethane.
  • the above dispersion was applied in a dilution of 60 grams/ liter to a staple fiber fabric and dried at 90 C.
  • Example 6 Into the apparatus described in Example 1 were introduced 450 parts of a solution of 0.1% strength of the ammonium salt of a copolymer of maleic acid and styrene. 15 parts of crotonic acid were added. In order to neutralize the crotonic acid, 35 parts of an unsaturated solution of sodium carbonate were added to the mixture which was then adjusted to a pH of 5. After having heated to 70 C., a solution of 15 parts of acryloyl-carbamic acid-butyl ester and 3 parts of benzoyl-peroxide in 270 parts of vinyl acetate were added with intensive stirring in the course of 4 hours. There were obtained clear glassy pearls which after washing and drying exhibited a residual monomer content of less than 0.3%.
  • copolymer pearls prepared by the above method were dissolved in aqueous alcoholic ammonia to such an extent that 50 grams of solid substance were present per liter of solution which had a pH of 8.5.
  • similar polymer pearls were also prepared without adding acyl urethane; these pearls were likewise dissolved in aqueous alcoholic ammonia at a pH of 8.5 so that the solution contained per liter 50 grams of solid substance.
  • cotton calico fabrics were treated with these solutions and dried at 100 C.
  • Example 7 A dispersion was prepared as described in Example 2, but instead of N-acryloyl-carbamic acid-butyl ester the same quantity of N-acryloyl-carbamic acid-isopropyl ester was used as copolymer component.
  • a staple fiber fabric was made crease-proof by impregnating it with:
  • a wool flannel was impregnated with an aqueous solution containing per liter 25 grams of the above-described copolymer and then dried at 90 C.
  • the flannel so treated showed a firm, full hand even after several washes, whereas a finish produced with a solution in water containing per liter 25 grams of polyacrylamide completely disappeared after one wash.
  • a process for the finishing of textile material which comprises treating the textile material with a liquid medium comprising copolymers of (A) 0.5 up to 90 parts by weight of unsaturated acyl urethanes of the general formula wherein R represents a member selected from the group consisting of an alkyl radical containing 1 to 6 carbon atoms, an alkyl radical with up to 6 carbon atoms being substituted by an alkoxy radical with up to 2 carbon atoms, the cyclohexyl radical, an aryl radical of low molecular weight and an aralkyl radical of low molecular weight, X represents a memher selected from the group consisting of oxygen and sulfur, and R-CO- represents a member selected from the group consisting of a radical of a carboxylic acid containing up to 2 carboxyl groups, up to 2 ethylene linkages and up to 6 carbon atoms, a radical of a monoester of a dibasic carboxylic acid, said acid containing up to 2 ethylene linkages and up
  • monomers which contain vinyl groups and which are selected from the group consisting of styrene, a vinyl ester of carboxylic acids with up to 6 carbon atoms, a vinyl ether of alkanols with up to 6 carbon atoms, an unsaturated carboxylic acid containing up to 2 carboxyl groups up to 6 carbon atoms, an amide of said unsaturated carboxylic acid, and an
  • component (A) 2-20 parts by weight of component (A) are copolymerized with 98 80' parts by weight of component (B).

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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)
US3123496D 1959-10-09 Process for the finishing of textile Expired - Lifetime US3123496A (en)

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Application Number Priority Date Filing Date Title
DEF29567A DE1145574B (de) 1959-10-09 1959-10-09 Verfahren zum Ausruesten von Textilmaterial

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US3123496A true US3123496A (en) 1964-03-03

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US (1) US3123496A (en, 2012)
CH (1) CH367145A (en, 2012)
DE (1) DE1145574B (en, 2012)
GB (1) GB908956A (en, 2012)
NL (1) NL103980C (en, 2012)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3634131A (en) * 1969-02-12 1972-01-11 Deering Milliken Res Corp Fugitively colored solid materials
US4710407A (en) * 1985-12-10 1987-12-01 Keeton Richard L Method for preserving fishing nets

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2335582A (en) * 1940-10-30 1943-11-30 Du Pont Fabric and finish

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL200174A (en, 2012) * 1952-04-16
US2719072A (en) * 1953-04-10 1955-09-27 Rohm & Haas The stabilization of protein-containing textiles and the resulting products
DE1011850B (de) * 1956-01-07 1957-07-11 Bayer Ag Verfahren zum Bedrucken, Klotzen oder Impraegnieren von Textilien oder anderen Fasersubstraten

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2335582A (en) * 1940-10-30 1943-11-30 Du Pont Fabric and finish

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3634131A (en) * 1969-02-12 1972-01-11 Deering Milliken Res Corp Fugitively colored solid materials
US4710407A (en) * 1985-12-10 1987-12-01 Keeton Richard L Method for preserving fishing nets

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NL103980C (en, 2012) 1900-01-01
GB908956A (en) 1962-10-24
DE1145574B (de) 1963-03-21
CH367145A (de) 1963-03-29
CH1117860A4 (en, 2012) 1962-10-31

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