Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/04—Ortho-condensed systems
• • 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
• • 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

Definitions

• 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 fab rics, 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.
• Another object is to provide a permanent press fabric finish
• Yet another object is to provide a process for applying to a fabric, and particularly to a cellulosic fabric, a permanent press finish.
• the product resulting from the reaction of compound (A), above, with formaldehyde according to the present invention is a novel aminoplast material, (B), comprising mono, di-, tri-, and tetramcthylolated 2,7dioxo-4,5-dimethyldecahydropyrimido-l4,5-d1-pyrimidine.
• the various compounds constituting this aminoplast material are collectively represented by following structural formula:
• whercin n represents an integer from 1 to 4, inclusive.
• the compound 2,7-dioxo-4,5-dimethyldecahydropyrimido-[4,5-dj-pyrimidine, is reported in 92 Monurslzqfrefrwr Chcmit 31 l96l) as a crystalline solid melting at 277C.
• This material can be prepared according to the aforementioned reference by the acid catalysed reaction between acetaldehyde and urea in aqueous mcnstruum.
• the ratio of the concentration of acetaldchyde to that of urea in the reaction system is at least about l.5, and preferably between about 1.8 and about 2.2.
• the reaction is desirably conducted at atmospheric pressure and at an elevated temperature, preferably at a temperature of between about 50C. and about C, with the atmospheric reflux temperature of the reaction system being especially preferred.
• lt is a feature of the present invention that the 2,7- dioxo-4,5-dimethyl-dccahydropyrimido-[ 4,5-d lpyrimidine must be employed in a high state of purity, i.c., in crystalline form.
• this material it is especially important that this material be free of color bodies which become noticeable when the aminoplast (B) is applied to a fabric, or during the lifetime of the treated fabric.
• a suitable cooling means e.g., an ice-bath
• the rate of addition is adjusted, if necessary, in order to maintain the reaction system at a temperature of about 20C.
• the reaction mixture is heated to atmospheric reflux temperature and maintained thereat for l hour. Thereafter, the reaction mixture is cooled to abient temperature, diluted with water, and filtered to isolate the crystalline product, (A).
• the product is washed with water, then with methanol, and finally recrystallized from water. After drying the recrystallized product at 70C., it weighs 1467 parts (25 percent of the theoretical yield based on urea) and melts at 275280C. Elemental analysis of the product corresponds to the formula C,,H N,O
• the reaction of 2,7-dioxo-4,5-dimethyldecahydropyrimido-[4,5-d]-pyrimidine, (B), with formaldehyde to produce the novel aminoplast material of the present invention is accomplished by con tacting (A) 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 dissolution of the reactants can take place.
• the concentrations of reactants are preferably those which result in a concentration of aminoplast material which in turn results in the desired amount of resin pick-up" 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.
• paraformaldehyde can be used in lieu of or in addition to formalin as the formaldehyde source.
• 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 2,7-dioxo-4,5-dimethyldecahydropyrimido-[4,5-dl-pyrimidine.
• the reaction between 2,7-dioxo-4,5-dimethyldecahydropyrimido[4,5-dj-pyrimidine and formalde hyde 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 2,7- dioxo-4,5-dimethyl-deeahydropyrimido-[4,5-d]- pyrimidine and formaldehyde are reacted are not critical. Desirably, the reaction is conducted at an elevated temperature and atmospheric pressure, with a tempera ture 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 determining when a particular reaction system has reached equilibrium is referred to in concentration with Example I hereinbelow.
• the aminoplast material (B) of the present invention is water-soluble, and is conveniently applied to a fabric in the form of 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., between a pair of rollers) to remove excess liquid, and subsequently cured.
• 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 275F. and about 425F. 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 300F. and about 350F. is employed.
• the time required for curing depends upon the curing temperature and catalyst concentration.
• the curing step is completed between about 5 seconds and about 30 minutes and preferably between about 3 and about l5 minutes.
• Substances suitable for catalysing the curing process include any conventional acid catalysts heretofore known to be useful in catalysting the curing of conventional aminoplast materials.
• Such catalysts are employed in conventional amounts, e.g., at concentrations 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 latent acid catalysts, e.g., ammonium chloride, magnesium chloride, zinc nitrate, and the like.
• the aqueous reaction mixture containing the novel aminoplast material (B) dissolved therein is cooled to ambient temperature, brought to a pH of about 7.0, and filtered to remove any insolubles which may be present. Then, a conventional amount ofa 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 padbath concentration of between about 5 percent and about 45 percent is used, with a concentration of between percent and about 25 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., formaldehyde and 2,7- dioxo-4,5-dimethyl-decahydropyrimido-[4,5-d]- pyrimidine) or by the judicious addition of water to an initially relatively highly concentrated solution of aminoplast materialv
• the treated fabric is withdrawn from the bath, wrung between rollers made of an inert material (e.g., metal, ceramic, rubber, and the like), preferably rubber rollers or adjacent, cooperatively functioning stainless steel/rubber rollers, dried 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.
• the percent pickup of the aminoplast composition is measured as: 70 Wet Pickup, after immersion in the pad bath solution; Dry Pickup, after curing; /r Dry Pickup, after I wash; and "/1 Dry Pickup, after 21 washes.
• Fabric, particularly cellulosic fabrics, treated with compound (B) according to the present invention exhibit, as will be seen hereinafter, very desirable and valuable permanent press properties.
• the examples which follow teach the novel composition of the instant discovery and processes for preparing same.
• treatment of fabrics with aminoplast material (B) is fully disclosed, as well as a number of tests comparing the latters efficacy with that of the following commercially popular resin forming compounds:
• PERMAFRESH* 113B (dimethyloldihydroxyethyleneurea) DMDHEU Trademark for permanent press compound sold by Sun Chemical (0., Wood River Junction, R.l. Trademark for permanent press compound sold by American (yanamid Cd, Bound Brook, NJ.
• Example I This example illustrates the novel aminoplast material (B) of the present invention and the process for producing same.
• the clear filtrate contains 2.5 percent free formaldehyde as determined by the sodium sulfite method" described in Walker, Formaldehyde, 3d ed., p. 486 (Reinhold, N.Y., l964).
• the concentration of aminoplast material in the aqueous fil trate is 60 percent by weight as determined gravimetrieally, i.e., by evaporating an aliquot sample of the solution at C. for 6 hours and weighing the residue.
• Example ll This example illustrates a variant of the procedure used in Example I to produce the aminoplast material of the present invention.
• the product 2,7-dioxo-4,S-dimethyl-dccahydropyrimido-l4,5-d1-pyrimidine/formaldchyde composition (8) of Example II. above, is used to treat plain weave white 50/50 cottonpolyester (PE) cloth, of the type used in shirts or household goods (e.g., sheets and pillowcases).
• PE cottonpolyester
• Example II TABLE V TEARING STRENGTH BY THE TONGUE (SINGLE RIP) METHOD Break Load (in pounds) Conventional soil redeposition test showed the product of Example II, i.e., compound (B), to be superior to Pcrmafrcsh l I3B (DMDHEU). Using a small amount of anti-soiI-rcdeposition agent for polyester/- cotton blends when subjecting the fabric of Example II, treated as taught in the same Example.
• the anti-soil-redeposition agent used is a water-soluble methyl cellulose derivative (4000 cps) bearing the trademark METHOCEL--HG and sold by Dow Chemical Corp., Midland, Michigan.
• a concentration of 1%, by weight, of Mcthocel'HG is added to the conventional soil redeposition test soiling bath alluded to hereinabove; the concentration, viz., 171 by weight, is based on the total weight of the soil bath.
• the use of methyl cellulose derivatives (Methocel) is claimed in copending application Scr. No. 22,140, filed Apr. 2, I970, by A. S. Fort et al and now Pat. No. 3,668,000.
• a process for imparting a permanent press finish to a cellulosic fabric wherein the fabric is contacted with an aqueous solution of an aminoplast material, said aminoplast material being a product of the reaction of and a molar excess of formaldehyde, and reaction with the fabric is effected at an elevated temperature in the presence of an acidic catalyst 2.
• the process of claim I wherein the aminoplast is tetramcthylolatcd.
• a process for imparting a permanent press finish to a cellulosic fabric comprising:
• step (a) conducting step (a) in the presence of an acid curing catalyst
• step (b) subsequently exposing the fabric treated in step (b) to an elevated temperature to cure the aminoplast material, said aminoplast material being formed by l. contacting a molar proportion ofa compound having the formula I l H H with between about 2.8 and about 5.0 molar proportions of formaldehyde;
• step (1) in an aqueous medium; 3. conducting step l in the presence of a catalytic amount of an acid or base; and 4. conducting step l) at a temperature between ambient temperature and the reflux temperature of the aqueous medium to effect reaction between said depicted compound and formaldehyde.
• step l at a temperature between ambient temperature and the reflux temperature of the aqueous medium to effect reaction between said depicted compound and formaldehyde.
• step (a) contacting the fabric with an aqueous solution of an aminoplast material; b. conducting step (a) in the presence of an acid curing catalyst; and e. subsequently exposing the fabric treated in step (b) to a temperature of at least about 275F. to cure the aminoplast material, said aminoplast material being formed by l. contacting a molar proportion of initially crystalline 2,7-dioxo-4,5-dimethyl-decahydropyrimido- [4,5-d]-pyrimidine with between about 2.80 and about 5.0 molar proportions of formaldehyde; 2. conducting step l in an aqueous medium; 3. conducting step l in the presence of a catalytic amount of an acid or base; and 4.
• step (1) at a temperature between ambient temperature and the reflux temperature of the aqueous medium to effect reaction be tween the 2,7-dioxo-4,5-dimcthyldecahydropyrimido-[ 4,5-d ]-pyrimidine and formaldehyde,
• the concentration of the aminoplast material in the aqueous solution used in step (a) is between about 2 percent and about percent by weight;
• the acid curing catalyst used in step (b) is selected from the group consisting of inorganic salts which behave as latent acid catalysts;
• the temperature employed in step (c) is between about 300F. and about 350F.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Priority Applications (10)

Applications Claiming Priority (1)

Publications (1)

Family

ID=22469610

Family Applications (1)

Country Status (10)

Cited By (1)

Citations (1)

• 0
  • CH CH580972D patent/CH580972D/xx unknown
• 1971
  • 1971-04-20 US US135776A patent/US3902846A/en not_active Expired - Lifetime
• 1972
  • 1972-04-18 FR FR7213548A patent/FR2133841A1/fr not_active Withdrawn
  • 1972-04-19 IT IT23385/72A patent/IT959603B/it active
  • 1972-04-19 LU LU65194D patent/LU65194A1/xx unknown
  • 1972-04-19 CA CA140,041A patent/CA988928A/en not_active Expired
  • 1972-04-20 BR BR2412/72A patent/BR7202412D0/pt unknown
  • 1972-04-20 DE DE19722219368 patent/DE2219368A1/de active Pending
  • 1972-04-20 NL NL7205317A patent/NL7205317A/xx unknown
  • 1972-04-20 BE BE782389A patent/BE782389A/xx unknown

Patent Citations (1)

Also Published As

Similar Documents