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
  • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
• • 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

• the present invention relates to a method for treating fibrous materials in order to improve the properties thereof and to the improved fibrous materials produced thereby. More particularly, the present invention relates to a method for improving the receptivity of fibrous materials, preferably of the cellulosic variety, including blends thereof with other fibrous materials of the natural and/ or synthetic types, to dyestuffs and fluorescent brightening agents not ordinarily substantive thereto. This invention also relates to an improvement in such other properties of fibrous materials as resistance to attack by mildew, laundry souls and the like, and to shrinking, washing and the like.
• fibrous materials consisting in whole or in part of cellulosic materials such as cotton and the like in general possess poor receptivity for aconsiderable number of the commercially available dyestuffs commonly employed in fiber coloring operations.
• Certain fiber-pretreatment methods have heretofore been proposed by which the physical and/ or chemical characteristics of cellulosic fibrous material are altered to thereby produce a fibrous material.
• Another object of this invention resides in the provision of fibrous materials having improved properties. Still other objects and advantages of the invention will become further apparent from the following detailed description thereof.
• the invention also comprises the provision of fibrous materials having improved receptivity to dyestuffs which ordinarily display but negligible aflinity for cellulosic fibrous materials such as those employed in coloring wool, nylon and the like. Moreover, it has been found that when fibrous materials are treated according to the present invention there is obtained a fiber product,
• a preferred class of compounds for use in the present invention is the class of compounds of the above formula wherein R represents the carbon atoms necessary to complete a 2-pyrrolidone ring, i.e., R in the above formula is ethylene.
• R represents the carbon atoms necessary to complete a 2-pyrrolidone ring, i.e., R in the above formula is ethylene.
• CH C O and the ring carbon-lower alkyl substituted derivatives thereof, where R is hydrogen or lower alkyl.
• R is hydrogen or lower alkyl.
• Com pounds of the above formula where R is lower alkyl can be formed by reacting Z-pyrrolidone with a mixture of paraformaldehyde and an alcohol.
• R represents the carbon atoms necessary to complete either a Z-piperidone or -caprolact am ring, i.e., R is propylene or butylene, respectively, are also highly effective agents for increasing the dye and fluorescent brightener recep- 3. tivity of fibrous materials treated therewith.
• the compounds can be structurally depicted as follows:
• the process of the present invention is applicable in general to fibrous materials constituted in whole or in part by labile hydrogen-containing substances such as cotton and other materials of the cellulosic type.
• textiles comprising 100 percent cotton, linen and the like and blends of fibers of cellulosic materials with fibers of other materials such as regenerated cellulose, e.g., viscose rayon or cuprammonium rayon, polyamides such as nylon, e.g., the polyamide of hexarnethylene diamine and adipic acid or of 6-aminocaproic acid; polyurethanes; acrylonitrile polymers and copolymers; polyesters such as polyethylene terephthalate; animal fibers such as wool and mohair; cellulose esters, e.g., cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate-propionate, cellulose acetate-butyrate and the like and cellulose
• an aqueous medium containing at least one lactam derivative of the type depicted in the foregoing formulae is applied to the fibrous material, following which the material so treated is dried and cured.
• the aqueous medium may be in the form of a solution, emulsion, suspension or other type of dispersion depending for example upon the physical properties of the particular lactam derivative employed, although the lactam derivatives of the present invention are all readily water soluble or dispersible, it may in some instances be desired to promote lactam solubility as for example by moderate heating of the aqueous media.
• the aqueous medium may further contain any suitable stabilizer, surface active agent and the like to assist in providing a suitably uniform medium for the fiber treatment.
• the aqueous medium may in addition contain a swelling agent for the fibrous material such as, for example, the butyl ether of ethylene glycol, acetone, dioxane and the like to promote conformity of distribution of the lactam derivative throughout the fibrous material.
• the aqueous treating medium is further. provided with an acid catalyst.
• Suitable catalysts are those which are acidic at the temperatures employed when applying the lactam solution to the fibrous material.
• these may be mentioned by way of illustrationammonium phosphate, also known as accelerator 187, Zinc chloride and zinc nitrate and the like.
• Acid-bound alkanol amines such as 2-methyl-2-amino-l-propanol hydrochloride, also known as catalyst A are particularly effective catalysts for carrying out the present invention.
• Other suitable catalysts are ammonium sulfate, oxalic acid and the amine hydrochloride known as Aerotex Accelerator 187 and the like.
• the catalyst may advantageously be added to the aqueous treating medium in the form of an aqueous solution just before the mixture is applied to the textile material.
• Catalyst proportions are not particularly critical and may range from about .1 percent to percent and higher based on the weight of lactam.
• the amount of catalyst should be increased. For example, if an alkaline substance is present in the fibrous material, e.g., as an impurity, it will probably poison the catalyst by reacting therewith, thereby reducing the effective amount of catalyst available for the fiber treatment. Accordingly, in such a case, the amount of catalyst should be increased to provide the desired effective amount thereof.
• the concentration of the lactam derivative in the aqueous medium is not particularly critical and may range from about 0.5 to 50 percent and higher, depending for example upon the method employed for applying the medium to the fibrous material, the particular lactam derivative and fibrous material employed, the properties desired in the fibrous material, etc.
• the aqueous treat ing compositions may be applied to the fibrous material by immersion, padding, spraying, painting or any other desired manner, continuous or otherwise. When overall effects are desired in the fabric material, it is preferred to apply an excess of the aqueous treating composition thereto followed by removal of excess as by squeezing, spinning, etc.
• the fibrous material is dried and then cured at a temperature of at least about C.
• the drying can be effected at temperatures of up to about 95 C. and higher, depending merely on the rate of drying desired.
• the duration of the curing step will in general vary inversely with the temperature employed although, of course, the temperature and time factors will also depend somewhat upon the type of fibrous material being treated, the particular lactam treating agent employed, the results desired, etc. In any event, the optimum curing parameters of time and/or temperature, may, in any particular instance, be readily determined by routine experimentation.
• the curing time will usually range up to five minutes or more for temperatures in the vicinity of approximately C.- C. with cotton materials, while the use of higher temperatures, e.g., up to 250 C. and higher, reduce proportionately the curing time required toin some instances-a matter of seconds.
• the fibrous material is desirably washed, preferably in the presence of a mild detergent, to remove any residual acidity, etc., and prevent the development of odor.
• the mechanism by which the process and compositions of the present invention yield fibrous materials having improved properties of the type enumerated hereinabove is not completely understood but can be postulated as follows.
• the labile hydrogen atoms present in the molecular structure of the fibrous material being treated enter into reaction with the N-methylol or N-alkoxymethyl substituent of the lactam derivative.
• an initial hydrolysis reaction occurs with the N-alkoxymethyl derivatives whereby such groups are converted to methylol.
• the labile hydrogen of the fibrous material may be present in the form of hydroxy, carboxy, amido, amino and/or cyano (hydrolysis provides amido and carboxyl hydrogen) and the like.
• the hydroxy groups may be present in the form of alkylol, e.g., methylol such as found in cellulose, its partial ethers and esters and cellulosic type materials such as cotton, or as glycol residues containing free hydroxy such as found in synthetic polyesters of the linear variety or such groups in vinyl type synthetic polymers.
• alkylol e.g., methylol such as found in cellulose, its partial ethers and esters and cellulosic type materials such as cotton, or as glycol residues containing free hydroxy such as found in synthetic polyesters of the linear variety or such groups in vinyl type synthetic polymers.
• the materials which contain and/ or provide labile hydrogen in the form of carboxy are the synthetic vinyl-type polymers known as the acrylics, synthetic polymers of the polyester type containing free carboxy within the molecular structure thereof, and materials which contain functional groups convertible to carboxy under the conditions of the treatment process described herein such as wool and polymers from acrylonitrile and the like.
• lact-am derivatives of the present invention chemically combine with the fibrous material being treated as evidenced by chemical analysis of the treated fiber product, application of severe wash tests, etc., as will be apparent from the examples given hereinbelow.
• the process of this invention is found to be highly effective for improving the properties of fibrous materials containing labile hydrogen within the molecular structure thereof, e.g., cellulosic materials such as cotton and the like, synthetic and animal fibers of the type indicated hereinabove, and blends of two or more of the foregoing materials.
• the fibrous material may be in any of the usual forms, e.g., staple, fiber or continuous filament in bulk form or in the form of tow, rope, yarns, slubbings, warps, fabrics, felts, and the like, and treated as a wound package, running length fibrous stock, bulk,
• the fibrous materials obtained by the process of the present invention exhibit a pronounced animalization effect which is probably due to the presence therein of chemically bound nitrogen, e.g., in the form of amide groups, resulting from the chemicalinteraction of the fibrous material and lactam derivative. Accordingly, the resultant fibrous material is characterized by many woollike properties, such as a pronouncedreceptivity for acid dyes, basic dyes, wool dyes, etc., fluorescent brighteners and the like.
• EXAMPLE 1 An aqueous solution containing parts of N-hydroxymethylpyrrolidone and 0.36 part of the. catalyst 2-methyl- Z-a-mino-l-propanol hydrochloride, which is added in the form of a 25 percent aqueous solution thereof, is applied by padding to cotton print cloth, 80 x. 80, at room temperature. The treated cloth is squeezed through rubber rollers to 100 percent weight pickup of solution and thereafter dried at about 80 C.85 C. The dried cloth is thereafter heat aired at 150 C.155 C. for approximately 3 minutes. Following this, the fabric is rinsed with cold water, boiled for approximately 10 minutes in the presence of a small amount of non-ionic detergent and rinsed again in cold water. Chemical analysis (Kjeldahl method) of the treated cloth indicates that approximately 83 percent of the N-hydroxymethylpyrrolidone-2, over and above that lost by sublimation (approximately 36 percent), is introduced into the treated cloth.
• Example 1 is repeated except that the cotton print cloth is replaced by a sample of Dacron-ccitton (60/40) fabric. Results s milar to those of Example I are obtained.
• the fibrous materials obtained from Examples 1 and 2 are found to posses in comparison to untreated control samples of the foregoing fibrous materials, significantly improved receptivity for basic dyes, acid dyes, wool dyes, etc., which are conventially employed in dyeing wool, nylon and the like and which possess little or no affinity for untreated cellulose materials. Further surprising is the discovery that the fibrous materials provided by the foregoing examples display, in addition to the above mentioned properties, a pronounced aflinity for fluorescent brightening agents commonly employed with wool, nylon, etc., as compared to untreated control samples of such fibrous materials.
• EXAMPLE 3 The cotton print cloth obtained from Example 1 and the Dacron-cotton (60/40) material obtained from Example 2 are each treated separately with an aminoooumarin fluorescent brightening agent of the following formula:
• the above compound is found to be substantive to each of the cloth samples which display a pronounced flourescent brightness in comparison to untreated control samples of each of these fibrous materials.
• fluorescent brightening agents which may be used with fibrous materials treated according to the present invention with the intention of like re sults there may be mentioned by way of example the amino coumarins described in U.S. Patent 2,610,152, the 4,4 di trizyldiaminostilbene 2,2 disulf nic acid derivatives described in U.S. Patent 2,612,501; the bis(2- morpholino 4 amino 1,3,5 triazyl (6) 4,4- diaminostilbene sulfonic and carboxylic acid materials described in U.S. Patent 2,618,636; the hydroxybenzimido-azolylstilbene carboxy esters described in U.S. Patent 2,937,997; the 4,5-diphenyl glyoxalone-disulfonic acid derivatives described in U.S. Patent 2,691,653; and the brightening agents described in U.S. Patent 2,688,777.
• EXAMPLE 4 Samples of cotton print cloth, x 80, and Dacroncotton, 60/40) treated according to the process described in Example 1 are dyed at the boil with a 1 percent aqueous solution of the acid dyestuif Colour Index Acid Yellow 121; C.I. No. 18690.
• the foregoing dyestuff exhibits a pronounced affinity for each of the cloth samples treated therewith which exhibit a vivid overall yellow color.
• Control samples of the untreated cloth materials exhibit negligible receptivity for the same dyestulf.
• Example 1 Furthermore, similar improved results as regards dye and fluorescent brightener receptivity are obtained when the procedure of Example 1 is repeated utilizing similar weight proportions of catalyst and lactam material but wherein the following compounds are substituted for the N-hydroxymethylpyrrolidone-Z compound of Example 1.
• Pyrrolidones N-methoxymethyl pyrrolidone-Z 3 ,3-dimethyl-N-hydroxymethylpyrrolidone-Z 3 ,3 ,5 -trimethyl-N-hydroxymethylpyrrolidone-2 3,3 ,5 -trimethyl-N-methoxymethylpyrrolidone-2 3-propyl, 5-methyl-N-hydroxymethylpyrrolidone-Z Piperidones N-hydroxymethylpiperidone-2 N-methoxymethylpiperidone-2 4,4-dimethyl-N-hydroxymethylpiperidone-2 6-propy1-N-methoxymethylpiperidone-2 4,4-dimethyl-N-ethoxymethylpiperidone-2 Epsilon-caprolactams 3,3,S-trimethyl-N-hydroxymethyl-E-caprolactam N-hydroxymethyl-E-caprolactam N-methoxymethyl-E-caprolactam 4,4-dimethyl-N-ethoxymethyl-E-caprolactam In each case, the samples of cotton print
• the fibrous materials provided by the process of the present invention are additionally characterized by an improvement in such other properties, such as resistance to attack by mildew as will be apparent from the following example:
• EXAMPLE 5 Samples of cotton print cloth, 80 x80 and Dacron-cotton (60/40) each treated in accordance with the process of Example 1 are subjected, along with untreated control samples of the foregoing materials, to soil burial tests for a period of approximately two weeks. In each case, the treated cloth samples exhibited improved resistance to mildew as compared to the untreated samples.
• the cellulosic materials treated in accordance with the present invention are capable of complexing or compounding with a variety of germicidal agents such as iodine and reducing the vapor pressure of the germicidal agent so that it remains on the cloth for substantial periods of time.
• germicidal agents such as iodine and reducing the vapor pressure of the germicidal agent so that it remains on the cloth for substantial periods of time.
• the combination of iodine and other germicidal and disinfecting agents with cloth treated in accordance with the present invention to produce germicidal bandages, surgical dressings, and the like forms the subject matter of the copending application of Leon Katz, filed Oct. 22, 1965, Ser. No. 502,618, now Patent 3,401,006 which most fully describes and claims the same.
• a process comprising treating fibrous materials containing labile hydrogen atoms with a composition consisting essentially of a compound selected from the group consisting of lactam derivatives of the formula:
• R represents a lower alkylene group necessary to complete a 5 to 7 membered heterocycle and R is selected from the group consisting of hydrogen and lower alkyl, and an acid catalyst contained in an aqueous medium, then drying and curing the fibrous material at a temperature of at least about C.
• lactam derivative is N-methoxyrnethylpyrrolidone-2-.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Microbiology (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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Cited By (3)

Citations (1)

• 1965
  • 1965-10-22 US US502387A patent/US3486838A/en not_active Expired - Lifetime
• 1966
  • 1966-10-19 BE BE688519D patent/BE688519A/xx unknown

Patent Citations (1)

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