GB855547A - Cellulosic textile materials and processes for making the same - Google Patents

Cellulosic textile materials and processes for making the same

Info

Publication number
GB855547A
GB855547A GB8834/57A GB883457A GB855547A GB 855547 A GB855547 A GB 855547A GB 8834/57 A GB8834/57 A GB 8834/57A GB 883457 A GB883457 A GB 883457A GB 855547 A GB855547 A GB 855547A
Authority
GB
United Kingdom
Prior art keywords
weight
hydroxide
dichloro
cross
propanol
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
Application number
GB8834/57A
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.)
Deering Milliken Research Corp
Milliken Research Corp
Original Assignee
Deering Milliken Research Corp
Milliken Research Corp
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 Deering Milliken Research Corp, Milliken Research Corp filed Critical Deering Milliken Research Corp
Publication of GB855547A publication Critical patent/GB855547A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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 sulfur or phosphorus
    • D06M13/248Treating 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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/272Unsaturated compounds containing sulfur atoms
    • D06M13/278Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/11Compounds containing epoxy groups or precursors thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/144Alcohols; Metal alcoholates
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/02Vinyl sulfones and precursors thereof

Abstract

Configuration-retaining properties are imparted to fabrics and yarns containing or consisting of cellulosic fibres having an average of at least 1,8 hydroxy groups per anhydroglucose unit by applying to the fibres (1) a proportion of water at least sufficient to swell them, but not exceeding 130% by weight of the bone-dry cellulosic fibres, (2) a catalyst which is an alkali metal hydroxide or an alkali-metal salt which, as a 1% aqueous solution, has a pH of at least 10, or a quaternary ammonium hydroxide, the proportion of hydroxide on a dry weight basis and calculated as sodium hydroxide being 2-30% by weight of the total water present and, where a salt is employed, the limits of the proportions being those equivalent to the proportions of hydroxide employed by the above definition, and the numerical product of the proportion of catalyst employed, calculated as sodium hydroxide and in terms of per cent by weight of the total water present, times the proportion of water present, in terms of per cent. by weight of the bone-dry cellulosic fibres, being not more than 4,000 and (3) at least 1% by weight of the cellulosic fibres of a cross-linking agent which forms a cross-linkage including a chain of at least 3 carbon atoms and is represented by one of the formulae: <FORM:0855547/IV(a)/1> wherein X represents halogen, R1, R2 and R3\t represent, in each instance, hydrogen or monovalent non-functional organic radicals, R4 represents a divalent connecting organic radical and Z, in each instance, is a divalent organic radical represented by one of the formulae: <FORM:0855547/IV(a)/2> wherein R5 and R6, in each instance, represent hydrogen or monovalent non-functional organic radicals, and X represents halogen. In a modification of the process the cross-linking agent is applied to the dry textile material and the catalyst is thereafter applied in the form of an aqueous solution. Alternatively the catalyst in the form of an aqueous solution may be applied to the textile material and the cross-linking agent thereafter applied. The cellulose fibres may be natural or may be composed of regenerated or partially esterified cellulose. Preferred crosslinking agents are 1, 3-dichloro-2-propanol and 2, 3-dichloro-1-propanol. Other agents which may be used are m-di (b , y-epoxypropoxy)-benzene; 1, 3-di(b -hydroxy-g -chloropropoxy)-2-propanol; 1, 2-di-(b -hydroxy-g -chloropropoxy) ethane; 1, 2-di(b ,g -epoxypropoxy)ethane; 1, 2, 3, 4-diepoxybutane; 1, 2, 5, 6-diepoxyhexane; 1, 5-dihydroxy-2, 4-dichloro-cyclohexane and 2, 6-dichloro-3, 4, 5-trihydroxy-5-hydroxymethyl-heptane. The preferred catalyst is sodium hydroxide, but trimethylphenylammonium hydroxide, sodium silicate or sodium sulphide may also be used. The proportion of cross-linking agent employed is preferably 6 to 30% by weight of the cellulosic fibres. In an example, a length of dry, desized and mercerised cotton material is impregnated with about 15% by weight of a mixture of about 70% of 2, 3-dichloro-1-propanol and 30% of 1, 3-dichloro-2-propanol and then passed through a 10% aqueous sodium hydroxide solution containing 2% sodium 2-ethyl-hexyl sulphate as a wetting agent to give about 70% pick up. The cotton is then passed through a short tenter frame, wound into a tight roll, stored at room temperature for 12 hours wrapped in polythene, unwound, scoured, washed and dried. Fabrics treated according to the invention can be repeatedly bleached with chlorine bleaches without yellowing.ALSO:Configuration-retaining properties are imparted to fabrics and yarns containing or consisting of cellulosic fibres having an average of at least 1,8 hydroxy groups per anhydroglucose unit by applying to the fibres (1) a proportion of water at least sufficient to swell them, but not exceeding 130% by weight of the bone-dry cellulosic fibres, (2) a catalyst which is an alkalimetal hydroxide or an alkali-metal salt which, as a 1% aqueous solution, has a pH of at least 10, or a quaternary ammonium hydroxide, the proportion of hydroxide on a dry weight basis and calculated as sodium hydroxide being 2-30% by weight of the total water present and, where a salt is employed, the limits of the proportions being those equivalent to the proportions of hydroxide employed by the above definition, and the numerical product of the proportion of catalyst employed, calculated as sodium hydroxide and in terms of per cent by weight of the total water present, times the proportion of water present, in terms of per cent by weight of the bone-dry cellulosic fibres, being not more than 4,000 and (3) at least 1% by weight of the cellulosic fibres of a cross linking agent which forms a cross linkage including a chain of at least 3 carbon atoms is represented by one of the formulae: <FORM:0855547/IV (c)/1> wherein X represents halogen, R1 R2 and R3 represent, in each instance, hydrogen or monovalent non-functional organic radicals, R4 represents a divalent connecting organic radical and Z, in each instance, is a divalent organic radical represented by one of the formulae: <FORM:0855547/IV (c)/2> wherein R5 and R6, in each instance, represent hydrogen or monovalent non-functional organic radicals, and X represents halogen. In a modification of the process the cross-linking agent is applied to the dry textile material and the catalyst is thereafter applied in the form of an aqueous solution. Alternatively the catalyst in the form of an aqueous solution may be applied to the textile material and the cross-linking agent thereafter applied. The cellulosic fibres may be natural or may be composed of regenerated or partially esterified cellulose. Preferred cross-linking agents are 1, 3- dichloro -2- propanol and 2, 3- dichloro -1- propanol. Other agents which may be used are mdi(b , g - epoxypropoxy) -benzene; 1, 3-di(b - hydroxyg - chloropropoxy) -2- propanol; 1, 2 -di-(b - hydroxy-g -chloropropoxy) ethane; 1, 2- di(b , g -epoxypropoxy) ethane; 1, 2; 3, 4- diepoxybutane; 1, 2; 5, 6- diepoxyhexane; 1, 5- dihydroxy-2, 4-dichlorocyclohexane and 2, 6- dichloro -3, 4, 5-trihydroxy -5- hydroxymethyl-heptane. The preferred catalyst is sodium hydroxide, but trimethylphenylammonium hydroxide, sodium silicate or sodium sulphide may also be used. The proportion of cross-linking agent employed is preferably 6-30% by weight of the cellulosic fibres. In an example, a length of dry, desized and mercerised cotton material is impregnated with about 15% by weight of a mixture of about 70% of 2, 3- dichloro -1- propanol and 30% of 1, 3- dichloro -2- propanol and then passed through a 10% aqueous sodium hydroxide solution containing 2% sodium 2- ethylhexyl sulphate as a wetting agent to give about 70% pick-up. The cotton is then passed through a short tenter frame, wound into a tight roll, stored at room temperature for 12 hours wrapped in polythene, unwound, scoured, washed and dried. Fabrics treated according to the invention can be repeatedly bleached with chlorine bleaches without yellowing. Permanent pleats may be imparted to fabrics by conducting the cross-linking while the fabric is in a pleated condition.
GB8834/57A 1956-04-03 1957-03-18 Cellulosic textile materials and processes for making the same Expired GB855547A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US575716A US2985501A (en) 1956-04-03 1956-04-03 Process of producing flat drying, wet crease resistant cellulosic fabrics by reaction with cross-linking agents and products produced thereby

Publications (1)

Publication Number Publication Date
GB855547A true GB855547A (en) 1960-12-07

Family

ID=24301419

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8834/57A Expired GB855547A (en) 1956-04-03 1957-03-18 Cellulosic textile materials and processes for making the same

Country Status (5)

Country Link
US (1) US2985501A (en)
BE (1) BE556279A (en)
DE (1) DE1221188B (en)
FR (1) FR1172972A (en)
GB (1) GB855547A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5320645A (en) * 1990-07-12 1994-06-14 Logue Bobby T Process for imparting wrinkle resistance and durable press finish to a fibrous garment

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3194627A (en) * 1956-04-03 1965-07-13 Deering Milliken Res Corp Processes for producing modified cellulosic textile materials
GB854962A (en) * 1958-05-19 1960-11-23 Ici Ltd New water-soluble reactive dyestuffs
NL113784C (en) * 1959-01-29
US3061399A (en) * 1959-02-09 1962-10-30 Stevens & Co Inc J P Treating cotton to improve wet and dry crease recovery in one operation
US3175875A (en) * 1960-04-25 1965-03-30 Deering Milliken Res Corp Cellulosic fabrics and methods for making the same
US3173750A (en) * 1960-10-19 1965-03-16 Deering Milliken Res Corp Method of imparting wet and dry crease recovery to cellulose textile fabric
BE618943A (en) * 1961-06-15
US3178250A (en) * 1961-07-10 1965-04-13 Gen Aniline & Film Corp Fiber improving process and product
NL283032A (en) * 1961-09-11
US3148236A (en) * 1961-10-30 1964-09-08 Monsanto Co Creasing process for thermoplastic materials
NL288980A (en) * 1962-02-15
US3069311A (en) * 1962-03-28 1962-12-18 Hercules Powder Co Ltd Paper manufacture
US3301631A (en) * 1962-08-21 1967-01-31 Deering Milliken Res Corp Process of modifying cellulosic textiles with epihalohydrin-triazone reaction products
US3259452A (en) * 1962-10-15 1966-07-05 Deering Milliken Res Corp Fabric formed from yarns which have a chemically induced configurational memory
US3445177A (en) * 1963-06-20 1969-05-20 Deering Milliken Res Corp Discharge printing a direct-dye dyed haloalkanol crosslinked cellulose fabric and creaseproofing with an aminoplast
US4009329A (en) * 1975-11-14 1977-02-22 Union Carbide Corporation Bioresistant cellulose ethers
US8821907B2 (en) * 2005-03-11 2014-09-02 Auburn University Office Of Technology Transfer Biocidal N-halamine epoxides

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL19083C (en) * 1924-04-04
GB510511A (en) * 1937-11-02 1939-08-02 Roger Wallach Improvements in the manufacture of textile fibres composed of cellulose ethers
US2524399A (en) * 1948-07-07 1950-10-03 Us Rubber Co Cellulose treated with di-vinyl sulfone to shrinkproof
BE491553A (en) * 1948-10-07
FR996986A (en) * 1948-10-07 1951-12-31 Fothergill & Harvey Ltd Process for treating textiles and the like, and products obtained by this process
GB724096A (en) * 1951-09-01 1955-02-16 Fothergill & Harvey Ltd Process for the dimensional stabilisation of cellulose fabrics
US2727034A (en) * 1952-05-31 1955-12-13 Roland R Mclaughlin Primary aromatic amino ether of cellulose and preparation of same
US2730427A (en) * 1952-08-13 1956-01-10 American Cyanamid Co Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5320645A (en) * 1990-07-12 1994-06-14 Logue Bobby T Process for imparting wrinkle resistance and durable press finish to a fibrous garment

Also Published As

Publication number Publication date
BE556279A (en)
FR1172972A (en) 1959-02-18
DE1221188B (en) 1966-07-21
US2985501A (en) 1961-05-23

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