US3627556A - Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins) - Google Patents

Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins) Download PDF

Info

Publication number
US3627556A
US3627556A US3627556DA US3627556A US 3627556 A US3627556 A US 3627556A US 3627556D A US3627556D A US 3627556DA US 3627556 A US3627556 A US 3627556A
Authority
US
United States
Prior art keywords
fabric
imidazolidinone
melamine
wool
dihydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Inventor
Philip B Roth
Somerset County
Herbert Jack Leavitt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Koratron Co Inc
Original Assignee
Koratron Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Koratron Co Inc filed Critical Koratron Co Inc
Application granted granted Critical
Publication of US3627556A publication Critical patent/US3627556A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/48—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing the ethylene imine ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—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
    • D06M15/37—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
    • D06M2101/10—Animal fibres
    • D06M2101/12—Keratin fibres or silk
    • 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
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • 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
    • D06M2200/45—Shrinking resistance, anti-felting 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
    • 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

  • a method for imparting durable press prop- This invention relates to durable press finishes. More particularly, it relates to a method for imparting durable press properties to textile materials containing protein fiber such as wool or mohair and cellulosic fibers by applying an aqueous solution of a resin forming material such as a combination of methylol melamine and 1,3-dialkylol-4,5 dihydroxy-Z-imidazolidinone and curing the finish in the presence of a curing catalyst. Still more particularly the invention relates to the curing of the resin finish by a deferred curing operation. Furthermore, it also relates to the textile materials thus treated.
  • a resin forming material such as a combination of methylol melamine and 1,3-dialkylol-4,5 dihydroxy-Z-imidazolidinone
  • Durable press finishes for cellulosic textile materials are well known.
  • the deferred curing technology of such finishes is also well known.
  • Large amounts of fabric are treated with the finishes and dried.
  • Manufacturers then cut and sew the fabric into garments and the garments are pressed to impart creases where creases are desired and smoothness and shape where creases are not desired.
  • Finished garments are then heated in an oven, or otherwise, to effect the curing of the finish on the completed garment.
  • the Koret patent, US. 2,974,432 describes the above process, now known as the Koratron process.
  • the preferred finish for use in the Koratron process contains 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, commonly called dimethylol-dihydroxy-ethyleneurea.
  • a curing catalyst such as zinc nitrate, is also normally present in the finish.
  • the finish when applied by a deferred cure process, imparts excellent durable press properties to cellulosic fibers, and blends of cellulosic and synthetic fibers.
  • the object of this invention is to provide a single bath, durable press finish for textile materials containing a protein fiber such as wool or mohair and cellulosic fibers, i.e., a finish suitable for the deferred curing method.
  • a finish suitable for the deferred curing method should not only provide crease retention where creases are desired, and smoothness of fabric where creases and wrinkles are not desired, but these qualities nited States Patent 0 must persist after laundering.
  • the finish should provide resistance to shrinkage due to laundering, and the hand of the fabric should be satisfactory.
  • the treated and dried fabric must be stable to storage before curing.
  • Fabric to be treated by the process of this invention contains at least 40%, preferably at least 45%, of wool fibers and at least 20%, preferably at least 25 of cellulosic fibers.
  • Cellulosic fibers include cotton and regenerated cellulose, i.e., rayon, particularly viscose rayon.
  • Other fibers may be present, including the synthetic fibers such as the polyamide (nylon) fibers, polyester (Dacron) fibers and polyacrylic (Orlon and Creslan) fibers.
  • the two types of aminoplast resins or reactants are (1) methylol melamines containing at least two methylol groups and (2) 1,3-dialkloyl-4,5-dihydroxy-2-imidazolidinone, wherein said alkylol group has from 1 to 3 carbon atoms, preferably 1,3-dimethylol-4,S-dihydroxy 2 imidazolidinone.
  • Both types of aminoplasts are well known and find extensive use on cellulosic fibers.
  • the methylol melamines also find use on wool to reduce shrinkage and felting.
  • melamine-based resins which may be used are methylated trimethylol melamine, methylated pentamethylol melamine, and methylated hexamethylol melamine, including hexa(methoxymethyl)melamine.
  • the preferred resin is a methylated trimethylol melamine, having at least 50% of the methylol groups methylated.
  • trimethylolmelamine it will be understood that the average number of methylol groups is from about 2.8 to 3.2. Combinations of 2 or more melamine-based resins may be used.
  • the two types of aminoplast resins are compatible in aqueous solutions.
  • the wool/cellulosic fabric is impregnated with the resin solution by any of the well-known procedures, including dipping, padding, spraying, etc.
  • the amount of melamine-based resin applied on the fabric is between 3% and 25% based on the weight of the fabric (O.W.F.), preferably between 4% and 18% O.W.F.
  • the amount of imidazolidinone-based resin ap plied is between 2% and 18%, preferably 3.5% and 12% O.W.F.
  • the total aminoplast resin should be at least 8% O.W.F., preferably at least 12% O.W.F.
  • the amount of melamine-based resin in the solution will be between 4% and 20% of the solution, preferably between 6% and 15%.
  • the amount of imidazolidinone-based resin will be between 3% and 15% preferably between 5% and 10%.
  • the catalyst utilized may be free acid. acid salts, alkanolamine salts, metal salts and the like.
  • concentration of catalyst employed may range from about 0.1 to about 25% or higher, based on the weight of the resin solids, depending upon the particular catalyst type employed.
  • a free acid such as phosphoric, tartaric, oxalic or the like
  • ammonium chloride amounts of from between 0.5 and about 10% are used.
  • amine salts including alkanolamine salts, such as diethanolamine hydrochloride, from about 1.0 to about 10% are most useful, while the respect to salts such as magnesium chloride, zinc chloride, zinc nitrate, and aluminum chloride,
  • the fabric After impregnation with the resin and catalyst solution, the fabric is dried at a temperature below 250 F., preferably at a temperature between 200 F. and 230 F. At the preferred range, between 1 and 10 minutes will normally be required.
  • the treated and dried fabric can be cured immediately, or after storage, in the fiat state, full benefit of this invention is obtained by cutting and sewing the treated, dried fabric into garments, which are pressed and shaped as desired.
  • the garments are then heated, as in an oven, for a sufficient length of time, to effect a cure of the finish on the fabric of the garment.
  • the garment thus acquires a durable press, with shape, desired creases and smoothness where each is desired.
  • the recommended curing temperature is between 290 F. and 350 F., preferably between 300 F. and 340 F.
  • the curing time will range from A. to 30 minutes, depending on the temperature used.
  • additives include softeners, water repellents, surface active agents, etc.
  • the precentages are by weight.
  • the retention of creases was evaluated by the AATCC Tentative Test Method 88C-1964T.
  • the smoothness of the fabric, i.e., the minimum care appearance, was evaluated by AATCC Tentative Test Method 88A 1964T, employing overhead lighting.
  • the fabrics were rated on a scale of 1-5, 5 representing the smoothest appearance and best retention of the original condition and 1 representing the poorest appearance and poorest retention of the original condition.
  • EXAMPLE 1 A 50/ 50 wool/rayon fabric was immersed in an aqueous solution containing 11.3% of partially methylated trimethylol melamine (Resin A), 7.0% of 1,3-dimethyl- 01-4,5-dihydroxy-2-imidazodinone (Resin B), 1.8% of zinc nitrate (Catalyst A), 1.1% of stearoylethyl dihydroxypropyl dimethyl ammonium chloride (Softener A) and 0.25% of ethylene oxide aciduct of nonylphenol (Surfactant A). The fabric was then passed through suitable rolls, as in a padder, so that the fabric had a 95% wet pickup. The fabric was dried at 210 F. for minutes. The treated fabric contained 10.7% of melamine resin and 6.7% of imidazolidinone resin.
  • a portion of the dried fabric was pressed to impart a crease and then cured by heating in an oven at 315 F. for 10 minutes.
  • the cured fabric was washed in a home-style, automatic washing machine using water at 140 F. and a detergent.
  • the washed fabric was tumble dried after each washing.
  • the shrinkage of the pressed and cured fabric was measured before and after 5 washing cycles.
  • the shrinkage of the untreated fabric was also measured. The results are shown in Table I as the percent shrinkage of warp (W) and fill (F).
  • the cured fabric exhibits excellent crease retention and excellent minimum care appearance after the washings.
  • Pad bath 1 Pad bath 2
  • Pad bath 3 Resin A, percent 11. 3 8. 0 6. 0 Resin B, percent 7.1 7. 1 7. 1 Catalyst A. percent 1. 8 1. 4 1. 2
  • Softener A percent 1.1 1.1 1.1 Surfactant A, percent- 0. 25 l). 25 0. 2
  • the pad baths were applied to 50/ 40/ 10 wool/rayon/ nylon fabric by a standard padding procedure obtaining a wet pick-up of
  • the fabrics were dried at 225 F. for 4 minutes.
  • the fabrics contained 9.0%, 6.4% and 4.8% of melamine resin and 5.7% of imidazolidinone resin.
  • Swatches of the dried fabric were creased by pressing for 10 minutes at 310 F.
  • the swatches were then heated in an oven at 340 F. for 10 minutes.
  • the swatches were washed five times in a home-style washing machine using water at 140 F., tumble drying after each washing cycle.
  • the shrinkage of the washed fabric, including a swatch of washed, untreated fabric, is shown in Table III as percent shrinkage of warp and fill. Crease retention and minimum care appearance of the washed fabrics are also shown in the table.
  • Fabrics 1, 2 and 3 correspond with pad baths 1, 2 and 3, respectively.
  • Swatches of the dried fabric were creased by pressing at 325 F. for 15 seconds, (1) immediately after drying, (2) after 14 days at F., and (3) after 7 weeks at room temperature. The swatches were then heated in an oven at 350 F. for 10 minutes.
  • EXAMPLE 4 A 50/50 wool/rayon fabric was immersed in an aqueous solution containing 8.4% of dimethylol melamine, 5.3% of Resin B, 1.0% of Water Repellent A, 3.1% of a textile softener (mixed cationic and anionic long-chain derivatives), 1.65% of Catalyst B and 0.25% of Surfactant A. The fabric was squeezed through rollers to impart a 95% wet pick-up. The fabric was dried at 225 F.
  • the fabric contained 8.0% of melamine resin and 5.0% of imidazolidinone resin.
  • a swatch of the dried fabric was pressed at 310 F. for 15 seconds and then heated in an oven at 317 F. for minutes.
  • the fabric demonstrated excellent crease retention after five washings in an automatic washing machine using water at 140 F.
  • a method for imparting durable press properties to textile fabrics containing protein and cellulose fibers comprising impregnating said fabric with an aqueous medium containing a polymethylol melamine, 1,3-dialkylol-4,S-dihydroxy-Z-imidazolidinone and a delayed action catalyst, said melamine being from about 3 to about 25 and said imidazolidinone being from about 2 to about 18% based on the weight of said fabric, and sub sequently drying and curing said impregnated fabric.
  • polymethylolmelamine is a methylated trimethylolmelamine having at least 50% of the methylol groups methylated.
  • imidazolidinone is 1,3-dimethylol-4,5-dihydroxy-2-imidazo1idinone.
  • a method of forming permanently creased garments comprising the steps of impregnating a fabric comprising a blend of cellulose and protein fibers with a single liquid formulation comprising an aqueous medium containing a resin forming material comprising polymethylol melamine and 1,3-dia1kylo1-4,5-dihydroxy-2- imidazolidinone and a catalyst, said melamine being from about 3 to about 25% and said imidazolidinone being from about 2 to about 18% based on the weight of said fabric with the total weight of the resin forming material being at least about 8% based on the weight of said fabric, drying and forming said impregnated fabric into a garment and imparting at least one crease thereto, and subsequently curing said creased garment to impart to said garment the property of crease retention.
  • imidazolidinone is 1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone.

Landscapes

  • 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)

Abstract

A METHOD FOR IMPARTING DURABLE PRESS PROPERTIES TO TEXTILE FABRICS CONTAINING A PROTEIN FIBER SUCH AS WOOL AND CELLULOSE FIBERS COMPRISING IMPREGNATING SAID FABRIC WITH A SINGLE BATH COMPRISING A RESIN FORMING MATERIAL WHICH MAY COMPRISE A COMBINATION OF MATERIAL, I.E., A POLYMETHYLO! MELAMINE AND 1,3-DIALKYLOL-4,5-DIHYDROXY2-IMIDAZOLIDINONE AND A DELAYED ACTION CATALYST, DRYING AND SUBSEQUENTLY CURING SAID METHYLOL MELAMINE AND 1,3-DIALKYLOL-4.5-DIHYDROXY-2-IMIDAZOLIDINONE ON SAID FABRIC, THE COMPOSITION FOR THE METHOD AND THE TREATED FABRIC.

Description

3,627,556 DURABLE PRESS FINISH FOR WOOL/CELLU- LOSIC FABRICS (MELAMINE/DIHYDROXY- IMIDAZOLIDIN ONE RESINS) Philip B. Roth, Bridgewater Township, Somerset County, N.J., and Herbert Jack Leavitt, Millbrae, Calif.; said Roth assignor to Koratron Company, Incorporated, San Francisco, Calif.
No Drawing. Filed July 29, 1968, Ser. No. 748,174
Int. Cl. D06m /54, 15/70 US. Cl. 117--10 Claims ABSTRACT OF THE DISCLOSURE A method for imparting durable press prop- This invention relates to durable press finishes. More particularly, it relates to a method for imparting durable press properties to textile materials containing protein fiber such as wool or mohair and cellulosic fibers by applying an aqueous solution of a resin forming material such as a combination of methylol melamine and 1,3-dialkylol-4,5 dihydroxy-Z-imidazolidinone and curing the finish in the presence of a curing catalyst. Still more particularly the invention relates to the curing of the resin finish by a deferred curing operation. Furthermore, it also relates to the textile materials thus treated.
Durable press finishes for cellulosic textile materials, particularly for blends of cellulosic textile synthetic fibers such as Dacron and nylon, are well known. The deferred curing technology of such finishes is also well known. Large amounts of fabric are treated with the finishes and dried. Manufacturers then cut and sew the fabric into garments and the garments are pressed to impart creases where creases are desired and smoothness and shape where creases are not desired. Finished garments are then heated in an oven, or otherwise, to effect the curing of the finish on the completed garment. The Koret patent, US. 2,974,432, describes the above process, now known as the Koratron process.
The preferred finish for use in the Koratron process contains 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, commonly called dimethylol-dihydroxy-ethyleneurea. A curing catalyst, such as zinc nitrate, is also normally present in the finish. The finish, when applied by a deferred cure process, imparts excellent durable press properties to cellulosic fibers, and blends of cellulosic and synthetic fibers.
Satisfactory durable press properties are not obtained when the above finish is applied by the deferred curing method to blends of wool and cellulosic fibers. Although good durable press properties can be imparted by applying two textile finishes in separate operations to blends of wool and cellulosic fibers, such operations are obviously time-consuming and undesirable.
The object of this invention is to provide a single bath, durable press finish for textile materials containing a protein fiber such as wool or mohair and cellulosic fibers, i.e., a finish suitable for the deferred curing method. Also, the finish should not only provide crease retention where creases are desired, and smoothness of fabric where creases and wrinkles are not desired, but these qualities nited States Patent 0 must persist after laundering. Furthermore, the finish should provide resistance to shrinkage due to laundering, and the hand of the fabric should be satisfactory. Lastly, the treated and dried fabric must be stable to storage before curing. It has now been discovered that the above objects can be attained by (1) applying, as a single bath, an aqueous solution which may contain two types of aminoplast resin to a textile fabric containing wool and cellulosic fibers, (2) drying the treated fabric of a temperature below the curing temperature, and (3) subjecting the dried fabric to a curing operation, either conventional or deferred.
Fabric to be treated by the process of this invention contains at least 40%, preferably at least 45%, of wool fibers and at least 20%, preferably at least 25 of cellulosic fibers. Cellulosic fibers include cotton and regenerated cellulose, i.e., rayon, particularly viscose rayon. Other fibers may be present, including the synthetic fibers such as the polyamide (nylon) fibers, polyester (Dacron) fibers and polyacrylic (Orlon and Creslan) fibers.
The two types of aminoplast resins or reactants (i.e., the resin or reactant precondensates) are (1) methylol melamines containing at least two methylol groups and (2) 1,3-dialkloyl-4,5-dihydroxy-2-imidazolidinone, wherein said alkylol group has from 1 to 3 carbon atoms, preferably 1,3-dimethylol-4,S-dihydroxy 2 imidazolidinone. Both types of aminoplasts are well known and find extensive use on cellulosic fibers. The methylol melamines also find use on wool to reduce shrinkage and felting.
Among the melamine-based resins which may be used are methylated trimethylol melamine, methylated pentamethylol melamine, and methylated hexamethylol melamine, including hexa(methoxymethyl)melamine. The preferred resin is a methylated trimethylol melamine, having at least 50% of the methylol groups methylated. By trimethylolmelamine, it will be understood that the average number of methylol groups is from about 2.8 to 3.2. Combinations of 2 or more melamine-based resins may be used.
The two types of aminoplast resins are compatible in aqueous solutions. The wool/cellulosic fabric is impregnated with the resin solution by any of the well-known procedures, including dipping, padding, spraying, etc.
The amount of melamine-based resin applied on the fabric is between 3% and 25% based on the weight of the fabric (O.W.F.), preferably between 4% and 18% O.W.F. The amount of imidazolidinone-based resin ap plied is between 2% and 18%, preferably 3.5% and 12% O.W.F. The total aminoplast resin should be at least 8% O.W.F., preferably at least 12% O.W.F.
Since the treated wool/cellulosic fabrics will normally pick up between 70% and of their weight of treating solution, the amount of melamine-based resin in the solution will be between 4% and 20% of the solution, preferably between 6% and 15%. The amount of imidazolidinone-based resin will be between 3% and 15% preferably between 5% and 10%.
The catalyst utilized may be free acid. acid salts, alkanolamine salts, metal salts and the like. The concentration of catalyst employed may range from about 0.1 to about 25% or higher, based on the weight of the resin solids, depending upon the particular catalyst type employed. Thus, for example, from between about 0.1 and about 10% of a free acid such as phosphoric, tartaric, oxalic or the like, may be employed, while in the case of ammonium chloride, amounts of from between 0.5 and about 10% are used. In the case of amine salts, including alkanolamine salts, such as diethanolamine hydrochloride, from about 1.0 to about 10% are most useful, while the respect to salts such as magnesium chloride, zinc chloride, zinc nitrate, and aluminum chloride,
3 amounts of between about 5 and 25%, preferably 8 to 15%, have been successfully employed. In all instances, the concentration of the catalyst is based on the Weight of the resin solids employed.
After impregnation with the resin and catalyst solution, the fabric is dried at a temperature below 250 F., preferably at a temperature between 200 F. and 230 F. At the preferred range, between 1 and 10 minutes will normally be required.
Although the treated and dried fabric can be cured immediately, or after storage, in the fiat state, full benefit of this invention is obtained by cutting and sewing the treated, dried fabric into garments, which are pressed and shaped as desired. The garments are then heated, as in an oven, for a sufficient length of time, to effect a cure of the finish on the fabric of the garment. The garment thus acquires a durable press, with shape, desired creases and smoothness where each is desired.
The recommended curing temperature is between 290 F. and 350 F., preferably between 300 F. and 340 F. The curing time will range from A. to 30 minutes, depending on the temperature used.
If desired, other textile treating agents and additives may be present in the resin/catalyst impregnating solution. These additives include softeners, water repellents, surface active agents, etc.
In the following examples, the precentages are by weight. The retention of creases was evaluated by the AATCC Tentative Test Method 88C-1964T. The smoothness of the fabric, i.e., the minimum care appearance, was evaluated by AATCC Tentative Test Method 88A 1964T, employing overhead lighting. The fabrics were rated on a scale of 1-5, 5 representing the smoothest appearance and best retention of the original condition and 1 representing the poorest appearance and poorest retention of the original condition.
The following examples are given to illustrate the invention and are not intended to be limitative.
EXAMPLE 1 A 50/ 50 wool/rayon fabric was immersed in an aqueous solution containing 11.3% of partially methylated trimethylol melamine (Resin A), 7.0% of 1,3-dimethyl- 01-4,5-dihydroxy-2-imidazodinone (Resin B), 1.8% of zinc nitrate (Catalyst A), 1.1% of stearoylethyl dihydroxypropyl dimethyl ammonium chloride (Softener A) and 0.25% of ethylene oxide aciduct of nonylphenol (Surfactant A). The fabric was then passed through suitable rolls, as in a padder, so that the fabric had a 95% wet pickup. The fabric was dried at 210 F. for minutes. The treated fabric contained 10.7% of melamine resin and 6.7% of imidazolidinone resin.
A portion of the dried fabric was pressed to impart a crease and then cured by heating in an oven at 315 F. for 10 minutes. The cured fabric was washed in a home-style, automatic washing machine using water at 140 F. and a detergent. The washed fabric was tumble dried after each washing. The shrinkage of the pressed and cured fabric was measured before and after 5 washing cycles. The shrinkage of the untreated fabric was also measured. The results are shown in Table I as the percent shrinkage of warp (W) and fill (F).
The cured fabric exhibits excellent crease retention and excellent minimum care appearance after the washings.
A portion of the dried, but uncured, fabric was stored for 7 weeks. Samples of this fabric were pressed to form EXAMPLE 2 Three pad baths were prepared of the following composition:
TABLE II Pad bath 1 Pad bath 2 Pad bath 3 Resin A, percent 11. 3 8. 0 6. 0 Resin B, percent 7.1 7. 1 7. 1 Catalyst A. percent 1. 8 1. 4 1. 2 Softener A. percent 1.1 1.1 1.1 Surfactant A, percent- 0. 25 l). 25 0. 2
The pad baths were applied to 50/ 40/ 10 wool/rayon/ nylon fabric by a standard padding procedure obtaining a wet pick-up of The fabrics were dried at 225 F. for 4 minutes. The fabrics contained 9.0%, 6.4% and 4.8% of melamine resin and 5.7% of imidazolidinone resin.
Swatches of the dried fabric were creased by pressing for 10 minutes at 310 F. The swatches were then heated in an oven at 340 F. for 10 minutes. The swatches were washed five times in a home-style washing machine using water at 140 F., tumble drying after each washing cycle. The shrinkage of the washed fabric, including a swatch of washed, untreated fabric, is shown in Table III as percent shrinkage of warp and fill. Crease retention and minimum care appearance of the washed fabrics are also shown in the table. Fabrics 1, 2 and 3 correspond with pad baths 1, 2 and 3, respectively.
TABLE III Minimum care appearance Shrinkage F percent Crease percent Untreated EXAMPLE 3 A 50/50 wool/rayon fabric was immersed in an aqueous solution containing 8.4% of resin A, 5.3% of resin B, 1.05% of mixed siloxanes (water repellent A) and 1.65% of magnesium chloride (Catalyst B). The fabric was squeezed through rollers to impart a wet pick-up and the fabric was dried at 225 F. for 3.0 minutes. The fabric contained 8.8 melamine resin and 5.6% imidazolidinone resin.
Swatches of the dried fabric were creased by pressing at 325 F. for 15 seconds, (1) immediately after drying, (2) after 14 days at F., and (3) after 7 weeks at room temperature. The swatches were then heated in an oven at 350 F. for 10 minutes.
All of the fabrics demonstrated excellent crease re tention after five washings in an automatic washing machine using water at 120 F.
EXAMPLE 4 A 50/50 wool/rayon fabric was immersed in an aqueous solution containing 8.4% of dimethylol melamine, 5.3% of Resin B, 1.0% of Water Repellent A, 3.1% of a textile softener (mixed cationic and anionic long-chain derivatives), 1.65% of Catalyst B and 0.25% of Surfactant A. The fabric was squeezed through rollers to impart a 95% wet pick-up. The fabric was dried at 225 F.
for 4 minutes. The fabric contained 8.0% of melamine resin and 5.0% of imidazolidinone resin.
A swatch of the dried fabric was pressed at 310 F. for 15 seconds and then heated in an oven at 317 F. for minutes.
The fabric demonstrated excellent crease retention after five washings in an automatic washing machine using water at 140 F.
While certain specific embodiments and preferred modes of practice of the invention have been described, it will be understood that this is solely for illustration, and that various changes and modifications of the invention may be made without departing from the spirit of the disclosure or the scope of the appended claims.
We claim:
1. A method for imparting durable press properties to textile fabrics containing protein and cellulose fibers comprising impregnating said fabric with an aqueous medium containing a polymethylol melamine, 1,3-dialkylol-4,S-dihydroxy-Z-imidazolidinone and a delayed action catalyst, said melamine being from about 3 to about 25 and said imidazolidinone being from about 2 to about 18% based on the weight of said fabric, and sub sequently drying and curing said impregnated fabric.
2. The method of claim 1 wherein said catalyst is a zinc salt.
3. The method of claim 2 wherein said catalyst is zinc nitrate.
4. The method of claim 1 wherein said melamine and imidazolidinone are applied in a combined weight between about 8% and 30% on the weight of fabric.
5. The method of claim 1 wherein said polymethylolmelamine is a methylated trimethylolmelamine having at least 50% of the methylol groups methylated.
6. The method of claim 1 wherein said textile fabric contains at least 40% wool and at least 20% cellulose.
7. The method of claim 1 wherein said textile fabric contains synthetic fibers.
8. A textile material having crease resistant properties as produced by the method of claim 1.
9. The method of claim 1 wherein said imidazolidinone is 1,3-dimethylol-4,5-dihydroxy-2-imidazo1idinone.
10. The method of claim 1 in which said impregnated fabric is dried at a temperature below about 250 F.
11. The method of claim 1 in which said impregnated fabric is cured at a temperature within the range of about 290 to about 350 F. for approximately to about 30 minutes.
12. The method of claim 7 in which said blend of fibers contains at least about 40% by weight protein fibers and at least about 20% by weight cellulose fibers.
13. The method of claim 10 in which said impregnated 6 fabric is dried at a temperature within the range of about 200 to about 230 F. for approximately 1 to about 10 minutes.
14. A method of forming permanently creased garments comprising the steps of impregnating a fabric comprising a blend of cellulose and protein fibers with a single liquid formulation comprising an aqueous medium containing a resin forming material comprising polymethylol melamine and 1,3-dia1kylo1-4,5-dihydroxy-2- imidazolidinone and a catalyst, said melamine being from about 3 to about 25% and said imidazolidinone being from about 2 to about 18% based on the weight of said fabric with the total weight of the resin forming material being at least about 8% based on the weight of said fabric, drying and forming said impregnated fabric into a garment and imparting at least one crease thereto, and subsequently curing said creased garment to impart to said garment the property of crease retention.
15. The method of claim 14 wherein said imidazolidinone is 1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone.
16. A permanently creased garment as produced by the method of claim 14.
17. The method of claim 14 in which said blend of fibers contains at least about 40% by weight protein fibers and at least about 20% by weight cellulose fibers.
18. The method of claim 14 in which said impregnated fabric is cured at a temperature within the range of about 290 to about 350 F. for approximately to about 30 minutes.
19. A textile material containing wool and cellulose fibers and impregnated with about 3 to about 25% based on the weight of said material of a polymethylol melamine, about 2 to about 18% based on the weight of said material of 1,3 dialkylol4,5-dihydroxy-2-imidazolidinone and a delayed action catalyst.
20. The textile material of claim 19 wherein said imidazolidinone is l,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone.
References Cited UNITED STATES PATENTS 2,731,364 1/-1956 Reibnitz et al. 117139.4 2,974,432 3/1961 Warnock et al. 1l7139.4 3,079,279 2/1963 Van Loo 117139.4 3,116,967 1/1964 Goldstein et al. 117139.4 X
WILLIAM D. MARTIN, Primary Examiner T. G. DAVIS, Assistant Examiner US. Cl. X.R.
US3627556D 1967-10-13 1968-07-29 Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins) Expired - Lifetime US3627556A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US67503867A 1967-10-13 1967-10-13
US67606767A 1967-10-18 1967-10-18
US74817568A 1968-07-29 1968-07-29
US74817468A 1968-07-29 1968-07-29

Publications (1)

Publication Number Publication Date
US3627556A true US3627556A (en) 1971-12-14

Family

ID=27505361

Family Applications (2)

Application Number Title Priority Date Filing Date
US3542505D Expired - Lifetime US3542505A (en) 1967-10-13 1967-10-13 Treatment of textiles with aziridine-modified polyurethanes
US3627556D Expired - Lifetime US3627556A (en) 1967-10-13 1968-07-29 Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins)

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US3542505D Expired - Lifetime US3542505A (en) 1967-10-13 1967-10-13 Treatment of textiles with aziridine-modified polyurethanes

Country Status (6)

Country Link
US (2) US3542505A (en)
CH (1) CH1524468D (en)
DE (1) DE1802808A1 (en)
FR (1) FR1588662A (en)
GB (1) GB1250332A (en)
NL (1) NL6814683A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide
US4306872A (en) * 1980-01-17 1981-12-22 American Cyanamid Company Imidazolidinones in a durable press process
US4307146A (en) * 1979-04-02 1981-12-22 Sumitomo Chemical Company, Limited Process for resin-finishing of textile fabrics and knitted goods

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2243068A1 (en) * 1972-09-01 1974-03-07 Bayer Ag PROCESS FOR THE FINISHING OF TEXTILE MATERIALS FROM FIBERS CONTAINING KERATIN
DE2914659A1 (en) * 1979-04-11 1980-10-23 Agfa Gevaert Ag MAGNETIC STORAGE MEDIUM AND METHOD FOR THE PRODUCTION THEREOF
US4263188A (en) * 1979-05-23 1981-04-21 Verbatim Corporation Aqueous coating composition and method
DE3435619A1 (en) * 1984-09-28 1986-04-03 Chemische Fabrik Pfersee Gmbh, 8900 Augsburg METHOD FOR SHRINKING AND FELT-FASTENING TEXTILE MATERIAL CONTAINING KERATINE FIBERS
IL123321A (en) * 1997-03-04 2001-01-11 Ciba Sc Pfersee Gmbh Process for treating wool-comprising fabrics
CN114940739B (en) * 2022-06-08 2023-07-11 万华化学集团股份有限公司 High-heat-resistance and easily-soluble TPU and preparation method thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881046A (en) * 1959-04-07 Process for reacting protein fibers with
NL55567C (en) * 1940-07-19 1900-01-01
US2891877A (en) * 1956-06-05 1959-06-23 Leon H Chance Flame resistant organic textiles and method of production
US3285798A (en) * 1962-06-06 1966-11-15 Stevens & Co Inc J P Chemical composition, process using same and resulting product
US3300274A (en) * 1963-10-22 1967-01-24 Allen G Pittman Process of treating textiles with perfluoroacyl bis-(1-aziridine) compounds and resulting textile products
US3279882A (en) * 1964-07-07 1966-10-18 Stevens & Co Inc J P Process of stabilizing proteinaceous materials through treatment with a polyethyleneimine and a polyaziridine
US3454671A (en) * 1964-11-02 1969-07-08 Bayer Ag Polyurethanes having improved dyeability,light fastness and fastness to waste gases and method of preparing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide
US4307146A (en) * 1979-04-02 1981-12-22 Sumitomo Chemical Company, Limited Process for resin-finishing of textile fabrics and knitted goods
US4306872A (en) * 1980-01-17 1981-12-22 American Cyanamid Company Imidazolidinones in a durable press process

Also Published As

Publication number Publication date
FR1588662A (en) 1970-04-17
DE1802808A1 (en) 1970-01-08
GB1250332A (en) 1971-10-20
CH1524468D (en) 1900-01-01
NL6814683A (en) 1969-04-15
US3542505A (en) 1970-11-24

Similar Documents

Publication Publication Date Title
US3649165A (en) Soil-release characteristics of textile materials
US2950553A (en) Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics
US3138802A (en) Process for imparting durable creases, wrinkle resistance and shape retention to cellulosic textile articles
US2137465A (en) Process of finishing textiles
US3676207A (en) Permanent sizing of yarns and fibers with durable polymers and copolymers for the production of fabrics with improved properties for particular end uses
US2804402A (en) Treatment of cellulose containing textile materials and compositions therefor
US2839429A (en) Treatment of cellulosic textile materials
US3540835A (en) Carboxylic acid group containing copolymer is applied to textile which has been treated with an aminoplast resin to improve soil release characteristics thereof
US2899263A (en) Eneurea
US2426770A (en) Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms
US3627556A (en) Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins)
US3472606A (en) Two-component wet fixation process for imparting durable press to cellulosecontaining materials
US3458869A (en) Method of producing press-free garments and products thereof
US3653805A (en) Delayed cure process using formaldehyde vapor to cause creaseproofing
US2739908A (en) Method of impregnating textile fabric with resin
US3094705A (en) Method for producing a pucker-free seam in a garment
US3546006A (en) Wet-fixation process for cellulosic fabrics using low add-ons of resins
US3181927A (en) Process of wet and dry wrinkleproofing cellulose fabric with an aminoplast resin and zinc chloride
US2988416A (en) Process of creaseproofing linen fabric by applying resin, mercerizing and reapplyingresin and product produced thereby
US3617188A (en) Soil release fabrics and method for producing same
US2378724A (en) Textile finishing and composition therefor
US3039167A (en) Method for improving the properties of fabrics containing cross-linked regenerated cellulose material
US3175875A (en) Cellulosic fabrics and methods for making the same
US3639096A (en) Process of treating direct dyed cellulosic textiles with a mixture of aminoplast creaseproofing agents and products resulting therefrom
US3526474A (en) Abrasion-resistant durably-pressed cellulosic textiles