US3224991A - Finishing process and composition comprising ethylenetriazine-urea-formaldehyde resin, melamine-formaldehyde resin and urea-formaldehyde resin - Google Patents

Finishing process and composition comprising ethylenetriazine-urea-formaldehyde resin, melamine-formaldehyde resin and urea-formaldehyde resin Download PDF

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Publication number
US3224991A
US3224991A US246354A US24635462A US3224991A US 3224991 A US3224991 A US 3224991A US 246354 A US246354 A US 246354A US 24635462 A US24635462 A US 24635462A US 3224991 A US3224991 A US 3224991A
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United States
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urea
fabric
formaldehyde resin
melamine
ethylenetriazine
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Expired - Lifetime
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US246354A
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English (en)
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Wilfert Gustav
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Akzona Inc
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American Enka Corp
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/30Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic and acyclic or carbocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated 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
    • Y10T442/2369Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2385Improves shrink resistance
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated 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
    • Y10T442/2369Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • This invention relates generally to the production of rayon lining material and more particularly to a finishing process and composition for producing nonshrinking rayon lining material having an improved crease recovery.
  • Wash-and-wear clothing made of fabrics comprising blends of synthetic yarns and wool or cotton does not shrink from laundering and needs little or no ironing.
  • the use to an increasing extent of such clothing requires an adequate supply of nonshrinking accessories of washand-wear quality, such as stiffening material, sewing yarn, and especially lining fabrics.
  • nonshrinking accessories of washand-wear quality such as stiffening material, sewing yarn, and especially lining fabrics.
  • cotton and rayon fabrics have been made shrink and crease resistant by finishing them with mixtures of various types of resins.
  • these treatments also result in a considerable deterioration of the physical properties of the fabrics. In particular, abrasion resistance and folding number are reduced considerably. Thus, the fabric becomes weak and brittle and consequently useless.
  • Another object of this invention is to provide a finishing process and composition for making cellulosic fabrics shrink resistant and having high crease recovery without substantially reducing the abrasion resistance and folding number of the fabric.
  • Still another object of this invention is to provide a finishing process and composition for rendering cotton and rayon fabric shrink and crease resistant without causing the fabric to become weak and brittle.
  • the cellulosic fabrics are treated with a composition comprising a mixture of 85-95 grams per liter ethylenetriazine-urea resin, 25-35 grams per liter melamine resin, and a very small amount of an urea resin in an aqueous medium and in the presence of a wash-fast substance which imparts improved hand and firmness, a wetting agent, a wash-fast hydrophobic softening agent, and a diammonium phosphate catalyst.
  • an organic complexing agent may be used if desired.
  • an exceptionally good finishing effect not heretofore obtained is produced, resulting in cellulosic fabrics that are very suitable for use as lining material in the manufacture of wash-and-wear clothing.
  • a critical feature of the finish composition is its very low urea resin content which must be maintained between 3,224,991 Patented Dec. 21, 1965 10 and 12 grams per liter of finishing bath. This is in contrast with known finish compositions using 60 to grams per liter to increase wet strength and shrink-fastness, and to grams per liter with an added catalyst for obtaining crease resistance and a wash-fastness. Surprisingly, the same finishing effects, particularly greater dry crease recovery, are obtained using a fraction of the commonly used amount of urea resin. Moreover, by thus considerably reducing the amount of urea resin, the undesirable action thereof on the fabric is avoided. This is of decisive importance for producing a practical fabric.
  • the desirable effect of the finishing process is attributed to the fact that the various known finishing agents used together surprisingly complement each other and that any unfavorable effects which result from their use are avoided by using very critical amounts.
  • ethylenetriazine-urea resin by itself produws good resistance to shrinkage and a satisfactory wet crease recovery, but poor dry crease recovery.
  • the urea resin necessary to improve the dry crease recovery impairs the other properties of the fabric, particularly, considerably reducing the folding number if used in the customary amount. By reducing that amount, these drawbacks are eliminated and it is still possible when used in combination with ethylenetriazine-urea resin in critical quantities to produce the desired dry crease recovery in the fabric.
  • the melamine component of the mixture further improves the wet crease recovery and favorably influences the hand as well as the Wash-fastness of the finishing effect.
  • addition of an organic complexing agent to the finish solution contributes to the improvement of the fabric properties, and the presence of a wash-fast substance to impart hand and firmness improves the character of the fabric, particularly the abrasion resistance.
  • Abrasion resistance and hand are also improved by a softening agent, for example, polyethylene imine.
  • Knittex CR neu The ethylenetriazine-urea resins used in the present in vention, identified by the trade name Knittex CR neu, correspond to the following type formula.
  • the ethylenetriazine ureas are mainly present in the monomolecular phase and react with the cellulose by splitting off water on the methylol groups.
  • the urea resins utilized in the present invention identified by the Sandoz carbamide composition Finish EN, belong to the so-called aminoplasts. These compounds are of the synthetic resin type and are obtained by the condensation of urea or thiourea and formaldehyde. Addition of the urea to formaldehyde produces a mixture of monomethylol urea, dimethylol urea, trimethylol urea, and tetramethylol urea. By increasing the amount of formaldehyde added, the composition of the mixture shifts toward the polymethylol compounds. In the desired reaction, one mole of urea is reacted with 2 to 3 moles of formaldehyde.
  • one methylol group reacts with one amino or imino group of the urea While splitting off water. This reaction may result in linear, branched, or cross-linked macromolecules, as is illustrated by the following equations.
  • the melamine resins useful in the present invention are those of the type referred to by the trade name Knittex MM.
  • the primary reaction is the addition of formaldehyde to form methylol groups, which continue to react, forming methylene ether bridges in an intermolecular fashion, or methylene bridges with NH or NH radicals.
  • the molar ratios of melamine/formaldehyde are generally between 1:3 to 1:6, with the properties of the resins being more or less dependent upon the number of bonded methylol groups.
  • the ethylenetriazine-urea resins and the melamine resins used in the present invention are products of Chemische Fabrik Pfersee.
  • the urea resin of the present invention identified by trade name Finish EN, is a product of Sandoz, Inc.
  • a typical wetting agent which may be used in the present invention is Nekanil LN, an alkylphenol polyglycolether produced by Badische Anilinand Soda-Fabrik A.G.
  • Typical of washfast hydrophobic softening agents which may be used in the present invention are Primenit VS, an octadecyl ethylene urea produced by Farbwerke Hoechst and Phobol PS (111), a dispersed synthetic resin made by Chemische Fabrik Pfersee and described in Lindners Tenside-Textilhesstoff-Waschrohstoife, 1964.
  • Particular polyacrylic ester dispersions and polyethylene dispersions which may be used in the present invention are Perapret HV and Perapret TX-1233, respectively, produced by Badische Anilinand Soda-Fabrik A.G.
  • an organic chelating or complexing agent it may be desirable to use an organic chelating or complexing agent to improve fabric properties.
  • Trilon B a sodium ethylenediamine tetra-acetate produced by Badische Anilinand Soda- Fabrik A.G.
  • Diamm-onium phosphate has been found to be a particularly suitable catalyst.
  • magnesium chloride, zinc chloride, or zinc nitrate were customarily HOHzC CI'IgO H used.
  • Such catalysts caused a high decrease in strength of the fabrics in contrast to diammonium phosphate which has only a mild effect, so that the fabric is not damaged as a result of a too violent condensation reaction of the finishing agents.
  • definite conditions must be observed in connection with the retreatment of the fabric and passage of the fabric through the machine. Particular attention must be paid to the reaction temperature, which must be chosen such that after pre-drying, a certain amount of moisture is left in the fabric.
  • EXAMPLE I An aqueous finishing bath was prepared containing the following agents per liter of solution. grams ethylenetriazine-urea resin (Knittex CR neu), 30 grams melamine resin (Knittex MM), 10 grams urea resin (Finish EN), 70 grams polyacrylic ester dispersion (Perapret HV), 2 grams wetting agent (Nekanil LN), 0.8 gram sodium ethylenediaminetetra acetate (T rilon B), 8 grams wash-fast hydrophobic softening agent (Phobol PS 111), 6 grams diamrnonium phosphate.
  • a rayon fabric was conventionally washed, preferably using an anionic detergent and thereafter dyed and dried between 90 and C. Finish was applied to the material by padding on a fowlard with a squeezing effect of about 75%. Subsequently the fabric was dried at about 70 C, such that about 10% of the moisture was retained. Thereafter, the material was cured for eight minutes at C. while in a relaxed state so as to allow the fabric to shrink freely. Subsequently, the cloth was calendered at 40 to 60 C. to obtain a satisfactory hand. Alternatively, a fine material having a good band may be obtained if after pre-drying and application of the finish, the fabric is calendered and then subjected to curing.
  • n( nshrink fabrics having improved crease recovery without loss in abrasion resistance.
  • the fabrics may be washed in any conventional manner at customary washing temperatures and have an excellent hand after drying. Because of their improved properties, they need not be ironed and thus may be used advantageously as lining material in Wash-and-wear clothing.
  • a process for producing nonshrinking rayon fabric having a high degree of crease recovery comprising fininshing the fabric with an aqueous solution containing a mixture of 85 to 95 grams per liter of an ethylenetriazine-urea resin having as its principal reactive component molecules of the formula H2CCH2 N 1'12C-CH2 l l I-IO.HQO.N NC CN N-CHzOH O (I!
  • a composition of matter comprising an equeous solution containing to grams per liter of an ethylenetriazine-urea resin having as its principal reactive component molecules of the formula 25 to 35 grams per liter of a melmamine resin having as its principal reactive components molecules of the formulae r urcmon o l C NIICI ⁇ QOI'I Trimethylol melamine HOHzQNDH OII Hexamethylol melamine 25 to 35 grams per liter of a melmarnine resin having as 1ts prmclpal reactive components molecules of the formulae NH.
  • a finishing composition for use in imparting shrink resistance and high crease recovery to cellulosic fabrics comprising an aqueous solution containing 85 to 95 grams per liter of an ethylenetriazine-urea resin having as its principal reactive component molecules of the formula 25 to 35 grams per liter of a melamine resin having as its principal reactive components molecules of the formulae Trimethylol melamine and I'IOH2C.1 ⁇

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US246354A 1962-01-04 1962-12-21 Finishing process and composition comprising ethylenetriazine-urea-formaldehyde resin, melamine-formaldehyde resin and urea-formaldehyde resin Expired - Lifetime US3224991A (en)

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Application Number Priority Date Filing Date Title
DEV0021830 1962-01-04

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US3224991A true US3224991A (en) 1965-12-21

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US (1) US3224991A (de)
AT (1) AT238679B (de)
BE (1) BE625594A (de)
CH (1) CH392450A (de)
DE (1) DE1444135A1 (de)
DK (1) DK104727C (de)
FI (1) FI41264B (de)
NL (1) NL286975A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531806A (en) * 1966-06-24 1970-10-06 Metro Atlantic Inc Production of durable shaped fabric articles using two-stage curing
US3920868A (en) * 1971-10-22 1975-11-18 Hoechst Ag Process for the manufacture of a chemically bonded non-woven fiber material in sheet form
US3956243A (en) * 1972-12-15 1976-05-11 Ciba-Geigy Corporation Process for flameproofing organic fibre material
US4400284A (en) * 1980-06-12 1983-08-23 Union Oil Company Of California Boron derivatives as lubricant additives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524727A (en) * 1947-01-30 1950-10-03 American Cyanamid Co Reaction products of an aldehyde and a triazine derivative
US2846337A (en) * 1955-09-28 1958-08-05 American Cyanamid Co Magnesium chloride catalyst for modified urea resins

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524727A (en) * 1947-01-30 1950-10-03 American Cyanamid Co Reaction products of an aldehyde and a triazine derivative
US2846337A (en) * 1955-09-28 1958-08-05 American Cyanamid Co Magnesium chloride catalyst for modified urea resins

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531806A (en) * 1966-06-24 1970-10-06 Metro Atlantic Inc Production of durable shaped fabric articles using two-stage curing
US3920868A (en) * 1971-10-22 1975-11-18 Hoechst Ag Process for the manufacture of a chemically bonded non-woven fiber material in sheet form
US3956243A (en) * 1972-12-15 1976-05-11 Ciba-Geigy Corporation Process for flameproofing organic fibre material
US4400284A (en) * 1980-06-12 1983-08-23 Union Oil Company Of California Boron derivatives as lubricant additives

Also Published As

Publication number Publication date
BE625594A (de) 1900-01-01
CH392450A (de) 1965-09-30
FI41264B (de) 1969-06-30
AT238679B (de) 1965-02-25
NL286975A (de) 1900-01-01
CH1400162A4 (de) 1965-02-15
DK104727C (da) 1966-06-27
DE1444135A1 (de) 1969-03-27

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