Classifications

• • 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
  • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
  • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
  • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
  • C08G12/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted diazines, diazoles or triazoles
• • 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
• • 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

• ABSTRACT Crotonylidenediurea is reacted between about 2.80 molar proportions and about 5.0 molar proportions of formaldehyde in aqueous medium to produce an aminoplast material.
• the aminoplast material forms a finish which imparts permanent press properties to the fabric.
• This invention relates to a novel aminoplast material.
• the invention also relates to a process for producing the aminoplast material and to the method for using same to impart permanent press properties to fabrics, particularly cellulosic fabrics.
• the term permanent press resins is understood to mean substances which, when applied to fabrics, impart to the fabrics properties of wrinkle resistance and durable press".
• the property of wrinkle resistance (which is synonomous with terms such as wrinkle-recovery, crease resistance,” and the like) refers to the ability ofa fabric to resist wrinkling and to retain smoothness of shape and hand upon repeated wear and laundering.
• the property of durable press (which is synonomous with terms such as crease retention and the like) is understood to mean the ability of a treated fabric to drip-dry without loss of crease and to be worn without ironing, although fastidious wearers may insist on some touch-up" ironing.
• textile finishing agents should impart to the substrate fabric a finish which does not suffer nor otherwise cause acid damage to the substrate fabric as a result of hypochlorite bleaching, and should be durable to alkaline conditions normally encountered in laundering.
• Another object is to provide a process for producing a novel composition of matter which, when applied to a fabric, and particularly to a cellulosic fabric, imparts a colorless, permanent press finish thereto, said finish having improved resistance to acid and alkaline degra dation normally encountered under ordinary bleaching and laundering conditions, which does not retain an undesirable amount of chlorine, and which does not cause substantial and unsightly discoloration of the fabric upon scorching.
• Another object is to provide a permanent press fabric finish having improved resistance to acid and alkaline degradation normally encountered under ordinary bleaching and laundering conditions, which does not retain an undesirable amount of chlorine, and which does not cause substantial and. unsightly discoloration of the fabric upon scorching.
• Yet another object is to provide a process for applying to a fabric, and particularly to a cellulosic fabric, a permanent press finish, said finish having improved resistance to acid and alkaline degradation normally encountered under ordinary bleaching and laundering conditions, which does not retain and undesirable amount of chlorine, and which does not cause substantial and unsightly discoloration of the fabric upon scorching.
• the product resulting from the reaction of crotonylidenediurea with formaldehyde according to the present invention is an aminoplast material comprising trimethylol crotonylidenediarea which has the following structural formula:
• HOH2CN N-CH2OH O Hue omort A H H The material crotonylidenediurea can be made by reacting urea with acetaldehyde in an acidic hydroxylic medium, for example, as described in US. letters Pat. No. 3,190,741.
• the crotonylidenediurea starting material must be employed in a high state of purity, i.e., in crystalline form.
• the crotonylidenediurea be free of color bodies or substances which give rise to color bodies which become noticeable when the aminoplast is applied to a fabric, or during the lifetime of the treated fabric.
• the novel aminoplast material of the present invention is not produced when formaldehyde is contacted in situ with the crude reaction product of urea and crotonaldehyde as described in US. letters Pat. No. 3,329,519.
• Crotonylidenediurea suitable for use in the present invention is conveniently and preferably prepared according. to the following procedure, it being understood, of course, that other methods of synthesis can be used without departing from the spirit of the invention:
• 270 parts by weight of urea are added to a mixtureof 99 parts of acetaldehyde and 600 parts of distilled water in a suitable-conventional reaction vessel.
• the resultant solution is heated to a temperature of about 60C.
• Thirty parts of phosphoric acid (catalyst) are then added and the temperature is thereafter maintained at between about 60C. and about 70C for 1 hour.
• the reaction mixture is subsequently cooled to ambient temperature whereupon the crotonylidenediurea crystallizes.
• the reaction of crotonylidenediurea with formaldehyde to produce the novel aminoplastic material of the present invention is accomplished by contacting crotonylidenediurea with between about 2.80 and about 5.0 molar equivalents of formaldehyde in a hydroxylic medium.
• the hydroxylic solvent used should be capable of dissolving the reactants and also capable of being separated from the aminoplast material formed in the reaction by evaporative means.
• the preferred solvent is water.
• concentrations of the reactants in the hydroxylic medium are not critical provided the dissolution of the reactants can take place. However.
• the concentrationsof reactants are preferably those which result in a concentration of aminoplast material which in turn determines the amount of resin pickup" experienced by the fabric within the pad bath.
• the reaction is conducted in formalin, i.e., an aqueous solution of formaldehyde in which the concentration of the latter is between about 35 and about 40 percent.
• formalin i.e., an aqueous solution of formaldehyde in which the concentration of the latter is between about 35 and about 40 percent.
• the amount of formaldehyde used can range between 2.80 and 5.0 molar proportions, and preferably between about 2.90 and about 3.05 molar proportions per molar proportion of crotonylidenediurea.
• the reaction between crotonylidenediurea and formaldehyde according to the present invention is catalysed by acid or base.
• the reaction can be conducted at a pH of less than or greater than 7.
• the reaction is conducted under basic conditions.
• the reaction is conducted at a pH of greater than about 8 and less than about 12, with a pH of between about 9 and about 10 being especially preferred.
• the temperature and pressure at which the crotonylidenediurea and formaldehyde are reacted are not critical. Desirably, the reaction is conducted at an elevated temperature and atmospheric pressure, with a temperature corresponding to the atmospheric reflux temperature of the reaction menstruum being preferred.
• the time required for completion of the reaction is generally less than 1 hour. The exact time required depends upon the reaction temperature, concentration of the catalyst (i.e., the pH) and reactants.
• a conventional titration method for determing when a particular reaction system has reached equilibrium is referred to in connection with Example 1 hereinbelow.
• the aminoplast material of the present invention is water-soluble, and is conveniently applied to a fabric as an aqueous solution. Accordingly, the reaction mixture, and preferably the aqueous reaction mixture, in which the aminoplast material is formed, can be used directly as the pad bath solution into which the fabric to be treated is immersed or dip treated. The fabric is then wrung out by conventional means (e.g., be-
• the curing of the aminoplast resin on the substrate. fabric is performed according to the present invention under conditions of elevated temperature and acid catalysis.
• a temperature of between about 50C and about 200C is generally effective in curing the instant aminoplast material to form a permanent press finish on the treated fabric.
• a curing temperature of between about C and about 200C is employed.
• the time required for curing depends upon the curing temperature and catalyst concentration.
• the curing step is completed between 1 and about 30 minutes and preferably between about 3 and about 15 minutes.
• Substances suitable for catalysing the curing process include any conventional acidic catalyst or catalysts heretofore known to be useful in catalysing the curing of conventional aminoplast materials.
• Such acid catalysts are employed in conventional amounts e.g., at a concentration of between about 1 percent and about 50 percent by weight based on the weight of aminoplast materials and includes as a general category those water-soluble inorganic salts which behave as so-called Bronsted acids. e.g., ammonium chloride, magnesium chloride, zinc nitrate, and the like.
• the aqueous reaction mixture containing the novel aminoplast material dissolved therein is cooled to ambient temperature, brought to a pH of about 7.0, and filtered to remove any insolubles which may or may not be present. Then, a conventional amount of an acidic curing catalyst is dissolved in the filtrate, and the fabric to be treated is immersed therein.
• the amount of resin picked-up" by the substrate fabric is determined in large measure by the concentration of the aminoplast material in the aqueous pad-bath solution.
• the concentration of the aminoplast-material in the pad bath solution (which can be determined gravimetrically) ranges between about 2 percent or less and about 65 percent by weight or more for cellulosic fabrics.
• a pad-bath concentration of between about 5 percent and about 45 percent is used, with a concen tration of between percent and about percent being especially preferred.
• the particular desired concentration of aminoplast material in any given instance is conveniently achieved by appropriate adjustment of the concentrations of reactants (i.e., fofmaldehyde and crotonylidenediurea) or by the judicious addition of water to an initially relatively highly concentrated solution of aminoplast material.
• the treated fabric is withdrawn from the bath, wrung between rollers made of an inert material (e.g., metal, ceramic, and the like), preferably stainless steel rollers, and simultaneously or subsequently heat cured at a temperature within the aforementioned range.
• the heat curing step can. if desired, be conducted by contacting the fabric with heated metal rollers, preferably heated stainless steel rollers, which rollers can be-the same or different than the rollers used in the wringing operation.
• Fabrics, particularly cellulosic fabrics, treated with the aminoplast material according to the present invention exhibit excellent permanent press properties.
• such fabrics are free of undesirable amounts of chlorine, and white fabrics so treated are not discolored nor does appreciable discoloration occur upon aging or scorching.
• EXAMPLE 1 This example illustrates the novel aminoplast of the present invention and the process for producing same.
• EXAMPLE 2 This example illustrates a variant of the procedure used in Example 1 to produce the trimethylol crotonylidenediurea aminoplast material of the present invention.
• EXAMPLE 3 This example illustrates the process of treating a cellulosic fabric (100 percent cotton) with the trimethylol crotonylidenediurea aminoplast material of the present invention.
• the pad baths used in this evaluation were prepared at two different concentrations, namely, 10 percent by weight permanent press resin and 25 percent by weight permanent press resin. Twenty percent Zinc nitrate (curing catalyst) based on the weight of aminoplast material was also included in each pad bath.
• a rating of l is ⁇ ery wrinkled and a rating of 5 is wrinkle-free (excellent durable press).
• the test procedure used is described in AAATC No. l24-I967 (2) A rating of l corresponds to an acceptably "soft feel: a rating of 5 corresponds to an undesirably stiff feel.
• EXAMPLE 4 The aqueous pad bath used in this example has the We claim: 1.
• a process for imparting a permanent press finish to a fabric comprising:
• ollowrng composition -HOH2C-N N-CHzOH CHQOH o t... Aminoplast 20 percent H H 5 b.
• conducting step (a) 1n the presence of an acid curzinc nitrate (curing catalyst) 4 percent (i.e.. 20 mg catalyst; and
• the fabric is a cellulosic fabric; Trim" X4000 05 percent the concentration of the aminoplast material in the aqueous solution used 1n step (a) IS between about d d 2 percent and about 65 percent by weight; Three 5amples (Nos; 7 9) 0ff1bnc are treats decor the acid curing catalyst used in step (b) is selected mg to the present mvemlon l three. sampkis T from the group consisting of inorganic salts which 1-3) are used as a control. After immersion, t e behave as Bronsted acids; and samples are wrung and cured for five minutes at 170 C.
• Step (c) Test results for the treated fabric are summarized 1n about 100C and about 200C.

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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)
• Phenolic Resins Or Amino Resins (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=26731362

Family Applications (1)

Country Status (4)

Cited By (1)

Citations (10)

• 1971
  • 1971-07-06 FR FR7124732A patent/FR2098212A1/fr not_active Withdrawn
  • 1971-07-07 DE DE19712133919 patent/DE2133919A1/de active Pending
  • 1971-07-07 GB GB3179371A patent/GB1307454A/en not_active Expired
• 1973
  • 1973-04-25 US US35383573 patent/US3876458A/en not_active Expired - Lifetime

Patent Citations (10)

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