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US3165424A - Treatment of cellulose textiles - Google Patents

Treatment of cellulose textiles Download PDF

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Publication number
US3165424A
US3165424A US20268A US2026860A US3165424A US 3165424 A US3165424 A US 3165424A US 20268 A US20268 A US 20268A US 2026860 A US2026860 A US 2026860A US 3165424 A US3165424 A US 3165424A
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US
United States
Prior art keywords
cellulose
water soluble
textile material
substance
treated
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
US20268A
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English (en)
Inventor
Konig Josef
Egon N Petersen
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.)
Phrix Werke AG
Original Assignee
Phrix Werke AG
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Filing date
Publication date
Application filed by Phrix Werke AG filed Critical Phrix Werke AG
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Publication of US3165424A publication Critical patent/US3165424A/en
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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
    • D06M13/10Treating 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
    • D06M13/12Aldehydes; Ketones
    • D06M13/127Mono-aldehydes, e.g. formaldehyde; Monoketones
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00Preparation of cellulose ethers
    • C08B11/02Alkyl or cycloalkyl ethers
    • C08B11/04Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/14Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with nitrogen-containing groups
    • 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
    • D06M13/12Aldehydes; Ketones
    • 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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03Polysaccharides or derivatives thereof
    • D06M15/05Cellulose or derivatives thereof
    • D06M15/09Cellulose ethers
    • 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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins

Definitions

  • the present invention relates to the treatment of textile materials so as to render the same crease resistant and wrinkle resistant, and more particularly to the treatment of cellulose materials to impart crease resistant and wrinkle resistant properties to the same while maintaining the strength of the material.
  • the textile material is coated with cellulose ethers of different kinds.
  • alkyl cellulose products such as methyl cellulose or methyl ethyl cellulose, which preferably should be completely etherified because otherwise they are not sufiiciently water-soluble, are not suitable because they can not prevent the stiffness and brittleness of a textile mate rial caused by the deposition of synthetic resins.
  • the present invention provides a method of providing crease resistance to cellulose material by a procedure which avoids all of the above and other enumerated disadvantages of the prior art.
  • the present invention mainly concerns a method of improving the upon heating to a predetermined temperature below the temperature at which damage to the cellulose textile material occurs is transformed into an insoluble resinous substance, the water soluble resin-forming substance con taining hydroxyl. groups, and also containing in solution a water soluble alkyloxy cellulose containing free bydroxyl'groups, and heating the thus treated cellulose textile material to the predetermined temperature so as to convert the water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the' same and the water soluble alkyloxy cellulose, thereby forming a treated cellulose textile material having improved properties.
  • the treating of the textile material may be carried out by spraying the same with the aqueous liquor, but is preferably accomplished by immersing thetextile material in the liquor.
  • the heating temperature is generally above 100 C. and is most-preferably at a temperature between 100 and 150 C.
  • the method of the present invention makes it possible to improve textile material of the cellulose type with respect to the crease resistance thereof while retaining the properties of strength and also while giving to the textile material a good feel.
  • the method of the present invention is particularly advantageous in that the crease resistance which is imparted to the textiles remains even after laundering.
  • This is achieved in accordance with the present inventionby the use of the cellulose mixed ether, that is the alkoxy cellulose which contains free hydroxyl groups in the cellulose molecule, these free hydroxyl Such" groups reacting with and cross linking the resin-forming substance, for example the dimethylol urea.
  • the cellulose mixed ether also has the advantage'of a good water solubility and the possibility of producing stable, non-flocculating solutions.
  • the alkyloxy alkyl celluloses which are utilized'in the present invention are produced by reacting an alkali cellulose with about 1 mol of a common alkylating agent and'about 3 mols of a common alkoxyl-ating agent, calculated per each mol of glucose anhydride of the cellulose.
  • I alkoxylating agent it is possible to use a lower alkylene Particularly good properties of the treated textile with re spect to crease or wrinkle resistance and good feel are achieved by maintaining the mol ratios of the produced cellulose ether as set forth above.
  • Celluloses of this type are suitable as starting material for the production of the mixed cellulose ethers of the present invention.
  • alkylating agent it is possible to use a "lowe'r alkyl halogenide such as methyl bromide,
  • oxide such as ethylene oxide, propylene oxide, ethylene I magnesium chloride, aluminum chloride, ammonium chlo-f ride,-ammonium nitrate, borax, etc. 1
  • suitable resin-forming substances for the purpose of the present invention are formaldehyde or such as methylol urea, dimethylol urea, melamine-formal-v dehyde condensates, methylol biuret, dimethylol biuret, the reaction product in neutral to slightly alkaline medium of methylol urea and glyoxal and similar products;
  • the textile material which has been treated with the liquor in accordance with the present invention, which actually have been impregnated with the liquor, for example'by spraying the liquor onto the textile material or preferably by immersing the material in the liquor, is
  • this predried textile material can be heated to a temperature up to 150 C. depending upon the duration of heating. 7
  • the Y drying and heating can also be carried out in a single step.
  • samples of the same cotton fabric were treated under the same conditions withliquors which instead of containing the etherified cellulose ethyloxyethyl cellulose in a mol ratio of 1:113, contained ethyloxy cellulose which was produced in a ratio of 0121- 1 luloseicalculated as glucose anhydride) to ethyl chloride to ethylene oxide in a mol ratio of 1:1:2 andin another test in a mol ratio of 1:1;4'.
  • Y The creaseangles'in Weft and warp threads and the feel characteristics of the treated samples and of the untreated samples were determined and are set forth in the following table:- e
  • the yellowish-brown reaction"productq' is filtered 01f by suction, pressed sharply-and dried under vacuum over calcium chloride.
  • the product is easilysoluble in cold water and no fiber residue remains upon dissolution.
  • Y yieldof thevdry reaction product is 60 to .g.
  • the diluting agent must be peroxide-free, ;To removethe peroxideithe. tetrahydrofurane is allowed to stand with concentrated potassium hydroxide with shaking frorn tirne to time, and after separation of the .potassium hydroxide liquor is'rectified.
  • a v a I I I EXAMPLE .II' V A treating 'liquidis used containing aper"liter l00 grams of technicalglyoxal .(consisting of 20% glyoxalic ,acid, 50% acetic acid and 30% glyorgal),"25 grams of technical borax and 2 grams. of an ethyloxyethyl cellu- .lose (molar relationship 111:3) prepared asndescribed in: Example I The solution 11am pH or 3.7. V
  • EXAMPLE III A rayon shirt material as described in Example II is soaked in a treating liquid containing 90 grams of the reaction product obtained by reaction of dirnethylol urea and glyoxal in aqueous solution at a pH of 7.5, 11.5 grams of AlCl .6H O, 10 grams of boric acid and 2 grams of the mixed cellulose ether described in Example II.
  • the pH-of the treating liquid is 3.6. Liquidis squeezed off to a residual moisture content of 100% and the material is then dried at between 100 and 110 C.
  • the thus treated material has a crease angle of 123/ 115, or of 108/ 120 after one washing'with sodium lauryl sulfonate, a rub resistance of 890 and pleasant'soft feel (touch).
  • the material finished with the same treating liquid except for the absence of'cellulose ether and under otherwise similar conditions has a crease angle of 128/131, or 11 l/111. after one washing with sodiuin laurylsulfonate and a rub resistance of 659.
  • a treating liquid is prepared which contains per liter 100 grams of dimethylol urea 100%, grams of NH NO and 2 grams of the ethyloxyethyl cellulose (molar relationship 1:1:3) similar to the ether used in Example Ill.
  • a sample of the rayon shirtmaterial'of Example 111 is soaked in this treating liquid and after removal of excess liquid by squeezing, the sampleis subjected to'a single drying step carried out forfive minutes at 130 C.
  • the crease angles in warp and Weft of the treated material are 142/140, or 122/130 after one washing with sodium lauryl sulfonate.
  • a sample of similar material finished with a treating liquid free of the addition of cellulose ether has crease angles-of '129/129, or 115/127.a'fter one washing with sodium lauryl sulfonate.
  • Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulosetextile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance which upon heating to a temperature between and C. is transformed into an insoluble resinousvsubstance, said water soluble resin-forming substance containing. hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether.
  • Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles comprising the steps of treating acellulose textile material'with an acid aqueous liquor containing in. solution a water soluble resin-forming substance which upon heating to a predeterminedtemperature below the temterial occurs is transformed into an insoluble resinous substance, said Water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol ofa lower alkyl halogenide as, an alkylating agent and about 3 mols of a lower alkylene oxide as an alkoxylatingagent calculated per eachmol of glucose anhydride of saidalkali cellulose; and heating the thus treated cellulose textile material to said predetermined temperature so as. to convert said water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction
  • Method of improving properties such'as the crease resistance and non-shrinking properties of cellulose textiles comprising the steps ;of treating a cellulose textile 'material'withan acid aqueous liquor containing in solution a water soluble resin-forming substance whichupon j heating-to a predetermined temperature below the temperature at which damage to said cellulose textile ma-zx terial occurs is transformed into an insoluble resinous,"- substance said water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a Water soluble alkyloxy alkyl cellulose mixed ,ether 7 containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol of an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bromide and ethyl chloride'and'about?
  • an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bro
  • an alkoxylating agent selected from the group consisting of ethylene oxide, propylene oxide and ethylene chlorohydrinycalculated ,per each mol of glucose an! hydride of said alkali cellulose; and heatingvithe thus 7 7:.-'Method of. improving properties such asi thecrease resistance and non-shrinkingproperties of cellulose textiles, comprising vthe stepsfof treatinga cellulose textile material with 'anyacid aqueousflliquorfliaving a pHbe ':tween 3 and 5 and containing in solution a water soluble resin-forming substance which upon'heatingato atemperature between '100 and 150" C.
  • said water soluble resin- 4 forming substance containing hydroxyl groups, and also containing'in solutiona Water soluble alkyloxy alkyl cellulose mixed ether containing ether'groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about-l mol of an alkylati'ng agent and about-3 mols of an, alkoxylating agent'calculatedper' eachrnol of glucose anhydride of saidj'alkalicellulose;
  • Method of improving properties such as the crease resistance and non-shrinkingproperties of cellulose textiles, comprising the steps of treatingacellulose textile material with an acid aqueous liquor containing in solu tion a Water soluble resin-forming substance which upon same' and saidwater soluble alkyloxy alkyl cellulose, thereby forming a treated'cellulose textile'rnaterial having improved properties.
  • Methodho d of improving properties such as the crease resistance and 'nonshrinking properties of cellulose textiles comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solu-- tion a 'waterisoluble resin-forming ,substancelwhiich upon heating to atemperature between 1.00 and 150 is transformed into an insoluble resinous substance; said '.water soluble resin-forming substance containing/hydroxyl groups, and "also containing in solution 1-;5 g.
  • tiles comprising the stepsof treatingla cellulose textile "material with'an acid aqueous liquor' haying av pH'be tween 3 and, 5 and containing in solution a wate'r solublei resin-forming" substance which' upon heating'to atem perature between and 15Q-C,. is trahsforrned into an insoluble resinous substance,"said*watersoluble'resinforming substance.
  • an alkali I cellulosel with about "1 fmol "of an alkylating agent”selected from the group;consist ing of methyl bromide, methyl chloride, 'eth yl bromide andiethyl chloride and about 3 mols of ani,,alkoxylating. agent selected from thegroup consisting of ethylene oxide; propylene oxide-and ethylene. chlorohydrin calculated pereach' molof glucose 'anhydridef of said'.
  • Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methylol urea and glyoxal which upon heating to a predetermined temperature below the temperature at which damage to said cellulose textile material occurs is transformed into an insoluble resinous substance, said water-soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose
  • Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor having a pH between 3 and 5 and containing in solution a Water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methyiol urea and glyoxal which upon heating to a termperature between and C.
  • a Water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methyiol

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth 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)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US20268A 1959-04-06 1960-04-06 Treatment of cellulose textiles Expired - Lifetime US3165424A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP22536A DE1093319B (de) 1959-04-06 1959-04-06 Verfahren zum Knitterfest- und Krumpffreimachen von Textilien aus nativer oder regenerierter Cellulose

Publications (1)

Publication Number Publication Date
US3165424A true US3165424A (en) 1965-01-12

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US20268A Expired - Lifetime US3165424A (en) 1959-04-06 1960-04-06 Treatment of cellulose textiles

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US (1) US3165424A (de)
CH (1) CH369102A (de)
DE (1) DE1093319B (de)
FR (1) FR1250302A (de)
GB (1) GB921058A (de)
NL (1) NL249295A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1652868A1 (de) * 2004-10-29 2006-05-03 Clariant (France) Aminoplastharzzusammensetzung

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4233497A1 (de) * 1992-10-06 1994-04-07 Basf Ag Verwendung von wäßrigen Polymerisatdispersionen als Textilhilfsmittel zur pflegeleichten Veredlung von Textilien

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1505043A (en) * 1922-06-10 1924-08-12 Lilienfeld Leon Cellulose ether and process of making same
US2190451A (en) * 1935-11-09 1940-02-13 Du Pont Cellulose derivatives
US2469431A (en) * 1945-09-27 1949-05-10 Carbide & Carbon Chem Corp Insolubilization of water-soluble hydroxyl-containing polymeric materials
US2644818A (en) * 1949-02-25 1953-07-07 British Celanese Manufacture of cellulose ethers
US2672427A (en) * 1951-05-26 1954-03-16 American Viscose Corp Process for rendering films and the like water-repellent, greaseproof, and moistureproof
US2949452A (en) * 1956-04-30 1960-08-16 Dow Chemical Co Process for preparing alkyl hydroxyalkyl cellulose ethers and the product obtained thereby

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB516624A (en) * 1938-06-29 1940-01-08 Roger Wallach Improvements in or relating to the treatment of textile materials
US2469348A (en) * 1945-04-07 1949-05-03 Dow Chemical Co Cellulose derivative compositions
BE495775A (de) * 1949-05-20
GB683069A (en) * 1949-09-13 1952-11-19 Courtaulds Ltd Improvements in and relating to the production of water-soluble mixed cellulose ethers
US2802752A (en) * 1953-12-30 1957-08-13 Apponaug Company Process of treating textile fabric

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1505043A (en) * 1922-06-10 1924-08-12 Lilienfeld Leon Cellulose ether and process of making same
US2190451A (en) * 1935-11-09 1940-02-13 Du Pont Cellulose derivatives
US2469431A (en) * 1945-09-27 1949-05-10 Carbide & Carbon Chem Corp Insolubilization of water-soluble hydroxyl-containing polymeric materials
US2644818A (en) * 1949-02-25 1953-07-07 British Celanese Manufacture of cellulose ethers
US2672427A (en) * 1951-05-26 1954-03-16 American Viscose Corp Process for rendering films and the like water-repellent, greaseproof, and moistureproof
US2949452A (en) * 1956-04-30 1960-08-16 Dow Chemical Co Process for preparing alkyl hydroxyalkyl cellulose ethers and the product obtained thereby

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1652868A1 (de) * 2004-10-29 2006-05-03 Clariant (France) Aminoplastharzzusammensetzung
US20060093843A1 (en) * 2004-10-29 2006-05-04 Clariant International Ltd. Aminoplast resin compositions
US7169881B2 (en) 2004-10-29 2007-01-30 Clariant (France) Aminoplast resin compositions
US20070100117A1 (en) * 2004-10-29 2007-05-03 Clariant (France) Aminoplast resin composition
US7399529B2 (en) 2004-10-29 2008-07-15 Clariant (France) Aminoplast resin composition

Also Published As

Publication number Publication date
CH369102A (de) 1963-06-29
DE1093319B (de) 1960-11-24
FR1250302A (fr) 1961-01-06
CH225960A4 (de) 1962-12-29
NL249295A (de)
GB921058A (en) 1963-03-13

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