US2785947A - Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom - Google Patents

Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom Download PDF

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Publication number
US2785947A
US2785947A US411542A US41154254A US2785947A US 2785947 A US2785947 A US 2785947A US 411542 A US411542 A US 411542A US 41154254 A US41154254 A US 41154254A US 2785947 A US2785947 A US 2785947A
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US
United States
Prior art keywords
acetal
textile material
carbon atoms
cellulose
acetals
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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
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US411542A
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English (en)
Inventor
Bernard H Kress
Abrams Ellis
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QUAKER CHEMICAL PRODUCTS CORP
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QUAKER CHEMICAL PRODUCTS 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
Priority to BE534688D priority Critical patent/BE534688A/xx
Priority to US732419A priority patent/US2585948A/en
Priority to US411542A priority patent/US2785947A/en
Application filed by QUAKER CHEMICAL PRODUCTS CORP filed Critical QUAKER CHEMICAL PRODUCTS CORP
Priority to CH331749D priority patent/CH331749A/de
Priority to CH332705D priority patent/CH332705A/de
Priority to CH334151D priority patent/CH334151A/de
Priority to CH332481D priority patent/CH332481A/de
Priority to CH327279D priority patent/CH327279A/de
Priority to GB36456/54A priority patent/GB780043A/en
Priority to FR1133319D priority patent/FR1133319A/fr
Priority to ES0219407A priority patent/ES219407A1/es
Priority to DEA21872A priority patent/DE1084232B/de
Priority to CH330794D priority patent/CH330794A/fr
Application granted granted Critical
Publication of US2785947A publication Critical patent/US2785947A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26DRYING
    • F26BDRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B13/00Machines and apparatus for drying fabrics, fibres, yarns, or other materials in long lengths, with progressive movement
    • F26B13/001Drying and oxidising yarns, ribbons or the like
    • 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
    • D06M13/137Acetals, e.g. formals, or ketals

Definitions

  • This invention provides a new process for treating cellulosic textile materials in order to obtain such mechanical effects as can be obtained by various types of calendering. Glazed, embossed, Shreinered, chased, and moir fabrics are among the types which can be produced by this-new process.
  • the fabrics produced according to this invention are spot, soil, and crease resistant, stretch and shrink resistant, launderable by washing or dry cleaning, quick drying,:ironable, and long wearing It is well-known in the art to obtain durablemechanical effects on cellulosicfabrics by impregnating .-same i in aqueous solutions of thermosetting resins and acidic or potentially acidic catalysts.
  • the impregnated fabrics are then dried at a relatively low temperature to a moisture content of about 10% and subsequently subjected to.
  • some type of hot calendering operation such as a glazer where the top roll travels more rapidly than the bottom roll. This operation glazes and partially sets the resin.
  • the fabric is passed through a curing oven operated at 300-400- F. for a period of about one-half to minutes, the length of time varying inversely with the temperature of cure'.
  • urea-formaldehyde resins urea-formaldehyde resins, thio-urea formaldehyde resins, melamine formaldehyde resins and various modified urea-formaldehyde resins.
  • thermosetting resin-forming products are all thermosetting resin-forming products.
  • Anobject of this invention' is to obtain :durable mechanical efiects on cellulosic fabrics which will be free from the danger of chlorine retention due to bleaching. Incidental to these efiects,-we also aim to obtain fabrics which are resistant to spotting, soiling, and'fraying and which possess improved .creaseresistance and substantial retention of tear and tensile strength.
  • a further objectof this invention is to provide a treatment which will impart a minimum degree of discoloration-to the-treated fabric. Further, the treated material will b'efree of objectionable odors or the disposition:. to form disagreeable odors. Moreover, the padding, drying, andcuringoperations will be substantially free of odors.
  • non-volatile acetals of monoaldehydes and dialdehydes containing up to eight carbon atoms in the presence of an acidic catalyst
  • non-volatile refers to non-volatility at the curing temperature of at least 250'F.
  • Suitable aldehydes which may be converted to acetals in this process are formaldehyde, acetaldehyde, propanal, butanal, glyoxal, and other monoand dialdehydes containing not more than eight carbon atoms in the monomeric form, such as -malonaldehyde, succinaldehyde, glutaraldehyde, adipaldehyde, hydroxyadipaldehyde, benzaldehyde, terephthalaldehyde, and the like.
  • Suitable alcohols which may be reacted with the abovementioned aldehydes to form acetals are methanol, ethanol, propanol, isopropanol, butanol, methoxyethanol, ethoxyethanol, methoxyethoxyethanol, ethylene glycol, a propylene glycol, a butylene glycol, diethylene glycol, ,dipropylene.
  • Suitable monomeric acetals applicable in this process are di-(hydroxyethoxyethyl) formal, di-(methoxyethoxyethyl) formal, di-(methoxyethyl) formal, di-(hydroxyethyl) formal, malonaldehyde tetra-(methoxyethyl) acetal, glyoxal tetramethyl acetal, glyoxal tetraethyl acetal, glyoxal tetrabutylzacetal, Z-hydroxyadipaldehyd tetra-(methoxyethyl) acetal and mixed acetals such as methyl methoxyethyl formal, malonaldehyde methyl triethyl acetal, glyoxaldibutyl dimethoxyethyl acetal, dimethoxymethoxyethyl ether, or methyl hydroxyethoxyethyl formal
  • the acetals are "prepared by reacting the aldehydes and alcohols in the'presence of acidic catalysts bywell-known procedures.
  • Mixed acetals maybe prepared by reactingthe, aldehyde with a mixture of the alcohols or by carrying out an exchange reaction between a given acetal and the desired alcohol.
  • our preferred monomeric acetals have boiling points above 125 C. and are derived from aldehydes containing one to eight carbon atoms and hydroxyl-bearing compounds containing at least one alkyl or alkylene radical, i. e. at least one continuous carbon chain possessing from one to six carbon atoms.
  • the polymeric acetals which are applicable in this invention are reaction products between an aldehyde and an alkylene or polyalkylene glycol.
  • Typical polymeric acetals may be prepared from diethylene glycol and formaldehyde, ethylene glycol and formaldehyde, diethylene glycol, formaldehyde and glyoxal, diethylene glycol, sorbitol and formaldehyde, diethylene glycol and acetaldehyde, dipropylene glycol and hydroxyadipaldehyde and the like.
  • those polymeric acetals which have proved useful in this invention may be made starting with ethyl- Y ene glycol, a propylene glycol, a butylene glycol, dipropylene glycol, dibutylene glycols, and higher dialkylene glycols, polyalkylene glycols, mixtures thereof, or their mixtures with diethylene glycol which are reactive with formaldehyde or other aldehydes to form water soluble products or products which are dispersible in water, either alone or with the aid of appropriate adjuvants.
  • Polyalkylene glycols such as triethylene glycol, tetraethylene glycol, tripropylene glycol and the like may also be used, either alone or in admixture with the aforementioned glycols.
  • polyols such as glycerine, pentaerythritol and sorbitol, may be added to the alkylene glycols in amounts up to about 50 mole percent of the glycols for reaction with the aldehyde for forming water soluble or water dispersible products.
  • Various materials such as paraform-aldehyde, formalin, trioxane, or methylal may be used as sources of formaldehyde.
  • alkylene is understood to include a doubly unsatisfied aliphatic radical containing a substituted or unsubstituted straight chain possessing from two to four carbon atoms in the chain and having its unsatisfied valences on either adjacent or separated carbon atoms. If desired, the chains of the polymeric compounds may be terminated, either in whole or in part, by means of an alkyl radical possessing not more than eight carbon atoms.
  • the water insoluble acetals were applied either i of the acetal.
  • the padding bath must contain additionally some acidic-type catalyst, such as zinc chloride, maleic anhydride, oxalic acid, ammoniumlchloride, ammonium thiocyanate, citric acid, tartaric acid, phosphoric acid, ethyl acid phosphate, ammonium sulfate, sodium bisulfate, etc., in amount of about 5 to 200% by weight to some suitable type of'calendering at about 350 to 400 one plain roll.
  • a linen-like effect may, be produced by chasing and a moir efiect can be obtained with specially engraved rolls.
  • the calendering is carried out at elevated temperature and at pressures approximating 5 tons per square inch. Subsequent to the calendering operation, the fabric is cured at a temperature of at least 250 F. for about A. to 10 minutes. The time of the cure varies inversely with the temperature. The cured fabric may then be washed lightly with a detergent and a mild alkali, rinsed thoroughly and dried.
  • Example I illustrates the prepartion of a typical polyformal as described in copending application, Serial Number 403,056 filed January
  • Example I Diethylene glycol moles.. 1 Paraformaldehyde -do-.. 1 Sulfuric acid do 0.001 Toluene ml 25
  • the above components are mixed and heated under reflux in an apparatus equipped with a water trap. The solution is refluxed and water removed by azeotropic distillation. When 1 mole of water of reaction is removed the desired reaction is complete.
  • the reaction mixture is neutralized with dilute sodium hydroxide solution and toluene is removed by evaporation in vacuo at temperatures not exceeding C.
  • the product is a viscous liquid, setting to a crystalline mass below 16 C. It is completely water soluble and also soluble in toluene and esters.
  • the product has a molecular weight of 480 (Rast) and a hydroxyl equivalent of 220 which indicates it has It has a specific gravity of 1.155 at 94 F.
  • the refractive index is N :1.462.
  • the molecular weight and hydroxyl equivalent of the condensation product of this example indicate that this product possesses a polymeric structure, containing an average of four diethylene glycol units, as shown in the following formula:
  • Example 11 Parts Diethylene glycol v 101 Beta methoxyethanol 4 Paraformaldehyde (91%) 30 Toluene 20 Sulfuric acid (99%) 0.1
  • Example II The above materials were reacted as in Example I to yield a viscous liquid possessing a faint ethereal odor and soluble in water. -Its polymeric nature was shown by Rast molecular weight determination which had a value of 63 7.
  • polyols may modify the polymeric condensation product.
  • Example III 7 These reactants were treated as in Example I. The product was a crystalline mass at room temperature, soluble in toluene and in Water, and virtually no odor.
  • Example IV An aqueous solutionis prepared containing the following:
  • the solution was padded on 80x 80 cotton sheeting at 100'percent pickup.
  • the fabric was dried at 180 F. until it reached a moisture content of 11% and then calendered through heated rolls at 400 F. and under a pressure of aboutS tons per square inch.
  • the fabric was then curedat 300 F. for 5 minutes and finally washed and dried.
  • the fabric possessed a lustrous finish which was substantially retained even after soaping at the boil for minutes.
  • the crease resistance was substantially improved and the retention of tear and tensile strength was good.
  • Chlorine retention tests conducted according to American'Association of Textile Chemists and Colorists (AL A. T. C. C. 1952) tentative specification-69 52 showed no effects due to retained chlorine.
  • a test with warm 5% sodium carbonate solution showed no indication of residual odor in the fabric.
  • Example V A solution containing the following materials was prepared:
  • Cotton sheeting (80 x 80) was treated as described in Example IV. The results were substantially the same as in Example IV.
  • Example VI An aqueous solution was prepared by dissolving the following materials:
  • Cotton sheeting (80 x 80) was treated as in ExampleIV. The material possessed a soft hand and a deep lustrous appearance.
  • Example VII An aqueous solution containing the following materials was prepared:
  • Cotton sheeting 80 x 80 was treated as in Example IV.
  • the treated fabric possessed a deep lustrous appearance and increased crispness over that shown in Example V.
  • Example VIII An aqueous impregnation bath was prepared containing the following materials:
  • Example IX Pounds Condensation product of Example 1-". Polyvinyl alcohol 7.5 Ammonium chloridei 17.0
  • Example XII A solution was preparedcontainingthe following:
  • This solution was used-to impregnatecotton sheeting (80 x 96) as described in Example IV.
  • the fabric was dried on a tenter frame to a moisture content of 11.5 and passed through specially engraved calender rolls at 375 F. to produce a moir effect.
  • The'fabric was then cured at 400 F. for 30 seconds, washed and dried.
  • the pattern retention on repeated laundering was excellent. Noobjectionable odors were noticed during the operations and the fabric showed no effects due to chlorine retention.
  • Example XIII The following solution was applied 'to cotton sheeting 80 x 80 as described in Example XII and with similar results:
  • cellulose textile material is intended to include fabrics, whether knitted, woven or felted, consisting of natural cellulose, regenerated cellulose, such as viscose rayon, cuprammonium rayon, and hydrolized cellulose acetate and mixtures thereof. Also included are fabric blends containing a preponderance of cellulosic type components.
  • the process of modifying the surface appearance of a cellulose textile material which comprises applying to a cellulose textile material an aqueous bath containing an acidic catalyst and an acetal of an aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydcs having 1 to 8 carbon atoms in monomeric form and mixtures of the aforesaid aldehydes, and an aliphatic hydroxyl-bearing compound selected from the group consisting of aliphatic monohydric alcohols containing from 1 to 5 carbon atoms, monoalkylene and polyalkylene glycols in which the alkylene radical has from 2 to 4 carbon atoms in a straight chain, and aliphatic polyhydric alcohols containing from 3 to 6 hydroxyl groups and from 3 to 6 carbon atoms and mixtures of the aforesaid aliphatic hydroxyl-bearing compounds, said acetal having a boiling point above about 125 C., said catalyst being present in amount from about
  • the process of modifying the surface appearance of a cellulose textile material which comprises applying to a cellulose textile material an aqueous bath containing an acidic catalyst and an acetal of an aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydes having 1 to 8 carbon atoms in monomeric form and mixtures of the aforesaid aldehydes, and an aliphatic hydroxyl-bearing compound selected from the group consisting of aliphatic monohydric alcohols containing from 1 to 5 carbon atoms, monoalkylene and polyalkylene glycols in which the alkylene radical has from 2 to 4 carbon atoms in a straight chain, and aliphatic polyhydric alcohols containing from 3 to 6 hydroxyl groups and from 3 to 6 carbon atoms and mixtures of the aforesaid aliphatic hydroxyl-bearing compounds, said acetal having a boiling point above about 125 C., said catalyst being present in amount from about 5% to

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US411542A 1947-03-05 1954-01-08 Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom Expired - Lifetime US2785947A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BE534688D BE534688A (lv) 1954-01-08
US732419A US2585948A (en) 1947-03-05 1947-03-05 Reel
US411542A US2785947A (en) 1954-01-08 1954-01-08 Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom
CH332481D CH332481A (de) 1953-05-08 1954-05-03 Verfahren zur Herstellung organischer Verbindungen
CH332705D CH332705A (de) 1953-05-08 1954-05-03 Verfahren zur Herstellung organischer Verbindungen
CH334151D CH334151A (de) 1953-05-08 1954-05-03 Verfahren zur Herstellung organischer Verbindungen
CH331749D CH331749A (de) 1953-05-08 1954-05-03 Verfahren zur Herstellung organischer Verbindungen
CH327279D CH327279A (de) 1953-05-08 1954-05-03 Verfahren zur Herstellung organischer Verbindungen
GB36456/54A GB780043A (en) 1954-01-08 1954-12-16 Process for stabilizing textile materials against dimensional changes and producing durable mechanical effects
FR1133319D FR1133319A (fr) 1954-01-08 1955-01-06 Procédé de stabilisation des matières textiles contre le rétrécissement
DEA21872A DE1084232B (de) 1954-01-08 1955-01-07 Verfahren zum Schrumpffestmachen von Cellulose enthaltenden Textilien
ES0219407A ES219407A1 (es) 1954-01-08 1955-01-07 Un procedimiento para el control dimensional de materiales textiles
CH330794D CH330794A (fr) 1954-01-08 1955-01-08 Bain aqueux stable pour le traitement d'une matière textile au moins en partie cellulosique

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US330794XA 1954-01-08 1954-01-08
US411542A US2785947A (en) 1954-01-08 1954-01-08 Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom

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BE (1) BE534688A (lv)
CH (1) CH330794A (lv)
DE (1) DE1084232B (lv)
FR (1) FR1133319A (lv)
GB (1) GB780043A (lv)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2903328A (en) * 1956-12-19 1959-09-08 Quaker Chemical Products Corp Process for the dimensional control of cellulosic materials
US2945738A (en) * 1958-01-29 1960-07-19 Chicopee Mfg Corp Low cover factor woven cellulose textile material resistant to corrugation in washing and tumble drying
US2988417A (en) * 1958-12-29 1961-06-13 Rohm & Haas Process for crease-proofing cellulosic fabrics
US3038777A (en) * 1959-06-10 1962-06-12 Courtaulds North America Inc Process for improving the properties of regenerated cellulose fibrous material
US3089747A (en) * 1958-04-04 1963-05-14 American Viscose Corp Method of preparing rayon plisse
US3099896A (en) * 1961-05-09 1963-08-06 Robert E Burns Soil treating composition and method
US3145132A (en) * 1961-08-02 1964-08-18 Kendall & Co Woven stretchable fabrics
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3198647A (en) * 1961-04-19 1965-08-03 Quaker Chem Corp Treated pigments and process for modifying the surface of pigments
US3227511A (en) * 1961-08-02 1966-01-04 Kendall & Co Methods of forming woven stretchable fabrics
US3240797A (en) * 1959-12-31 1966-03-15 Deering Milliken Res Corp Bis (sulfatoethyl) sulfoxide salts
US3278470A (en) * 1961-12-27 1966-10-11 Ici Ltd Condensation products of formaldehyde resin precondensates with polyacetals
DE1233817B (de) * 1963-10-03 1967-02-09 Pfersee Chem Fab Verfahren zur Hochveredlung von Textilmaterialien, die natuerliche und/oder regenerierte Cellulosefasern enthalten
US3642508A (en) * 1970-06-01 1972-02-15 Texaco Inc Sand consolidation composition containing 2-hydroxyadipaldehyde, water and an organic solvent
US3872000A (en) * 1972-04-08 1975-03-18 E C Chemical Ind & Co Ltd Liquid flocculant comprising condensation product of aromatic aldehyde and polyol
US4656296A (en) * 1983-06-01 1987-04-07 Sun Chemical Corporation Novel compounds and their use as insolubilizers for binders for paper coating compositions
US4900324A (en) * 1987-05-18 1990-02-13 The United States Of America, As Represented By The Secretary Of Agriculture Agents for non-formaldehyde durable press finishing and textile products therefrom
US6544296B2 (en) 2000-02-07 2003-04-08 The Proctor & Gamble Company Enhanced fabric comprising substrates and process to provide same
US6953485B2 (en) 2000-02-07 2005-10-11 Strike Investments, Llc Enhanced fabric comprising substrates and process to provide same
US20080194453A1 (en) * 2005-03-15 2008-08-14 Frank-Peter Lang Washing and Cleaning Agents Containing Acetales as Organic Solvents
US20090030241A1 (en) * 2005-03-15 2009-01-29 Frank-Peter Lang Novel Amphiphile Acetals
US20090031504A1 (en) * 2005-03-15 2009-02-05 Frank-Peter Lang Method for Chemically Cleaning Textile Material

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69208311T2 (de) * 1991-09-30 1996-07-04 Osi Specialties Inc Verfahren zum Knitterfreimachen von Baumwolltextilien ohne Anwendung von Formaldehyd
DE102005021444A1 (de) * 2005-05-10 2006-11-16 Clariant Produkte (Deutschland) Gmbh Glyoxal-Alkylpolyglykolether-Acetale
DE102006042448A1 (de) * 2006-09-09 2008-03-27 Clariant International Limited Lederpflegemittel enthaltend Acetale als organische Lösemittel

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB291473A (en) * 1926-12-01 1928-06-01 Tootal Broadhurst Lee Co Ltd Improved cellulosic materials and the production thereof
US2207740A (en) * 1935-04-18 1940-07-16 Heberlein Patent Corp Process for producing water-repellent cellulose-containing materials and products therefrom
GB527888A (en) * 1939-04-22 1940-10-17 Calico Printers Ass Ltd An improved process for the treatment of regenerated cellulosic materials
GB547846A (en) * 1939-03-04 1942-09-15 Cilander Ag Improvements in or relating to the aldehyde treatment of cellulosic textile materials
US2350350A (en) * 1941-05-06 1944-06-06 Du Pont Glycol formals
US2360477A (en) * 1941-04-11 1944-10-17 Gustavus J Esselen Inc Polymeric acetals and process of forming same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE648792C (de) * 1933-01-15 1937-08-07 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von knitterfesten Textilgeweben
DE852390C (de) * 1948-10-02 1952-10-13 Glanzstoff Ag Verfahren zum Veredeln von Cellulosehydratgut
BE509882A (lv) * 1950-07-11
US2643236A (en) * 1950-12-29 1953-06-23 American Cyanamid Co Method of preparing condensation products of pentaerythritol and glyoxal

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB291473A (en) * 1926-12-01 1928-06-01 Tootal Broadhurst Lee Co Ltd Improved cellulosic materials and the production thereof
US2207740A (en) * 1935-04-18 1940-07-16 Heberlein Patent Corp Process for producing water-repellent cellulose-containing materials and products therefrom
GB547846A (en) * 1939-03-04 1942-09-15 Cilander Ag Improvements in or relating to the aldehyde treatment of cellulosic textile materials
GB527888A (en) * 1939-04-22 1940-10-17 Calico Printers Ass Ltd An improved process for the treatment of regenerated cellulosic materials
US2360477A (en) * 1941-04-11 1944-10-17 Gustavus J Esselen Inc Polymeric acetals and process of forming same
US2350350A (en) * 1941-05-06 1944-06-06 Du Pont Glycol formals

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2903328A (en) * 1956-12-19 1959-09-08 Quaker Chemical Products Corp Process for the dimensional control of cellulosic materials
US2945738A (en) * 1958-01-29 1960-07-19 Chicopee Mfg Corp Low cover factor woven cellulose textile material resistant to corrugation in washing and tumble drying
US3089747A (en) * 1958-04-04 1963-05-14 American Viscose Corp Method of preparing rayon plisse
US2988417A (en) * 1958-12-29 1961-06-13 Rohm & Haas Process for crease-proofing cellulosic fabrics
US3038777A (en) * 1959-06-10 1962-06-12 Courtaulds North America Inc Process for improving the properties of regenerated cellulose fibrous material
US3240797A (en) * 1959-12-31 1966-03-15 Deering Milliken Res Corp Bis (sulfatoethyl) sulfoxide salts
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3198647A (en) * 1961-04-19 1965-08-03 Quaker Chem Corp Treated pigments and process for modifying the surface of pigments
US3099896A (en) * 1961-05-09 1963-08-06 Robert E Burns Soil treating composition and method
US3145132A (en) * 1961-08-02 1964-08-18 Kendall & Co Woven stretchable fabrics
US3227511A (en) * 1961-08-02 1966-01-04 Kendall & Co Methods of forming woven stretchable fabrics
US3278470A (en) * 1961-12-27 1966-10-11 Ici Ltd Condensation products of formaldehyde resin precondensates with polyacetals
DE1233817B (de) * 1963-10-03 1967-02-09 Pfersee Chem Fab Verfahren zur Hochveredlung von Textilmaterialien, die natuerliche und/oder regenerierte Cellulosefasern enthalten
US3396050A (en) * 1963-10-03 1968-08-06 Pfersee Chem Fab Process of refining textile materials containing natural and/or regenerated cellulosic fibers
US3642508A (en) * 1970-06-01 1972-02-15 Texaco Inc Sand consolidation composition containing 2-hydroxyadipaldehyde, water and an organic solvent
US3872000A (en) * 1972-04-08 1975-03-18 E C Chemical Ind & Co Ltd Liquid flocculant comprising condensation product of aromatic aldehyde and polyol
US4656296A (en) * 1983-06-01 1987-04-07 Sun Chemical Corporation Novel compounds and their use as insolubilizers for binders for paper coating compositions
US4900324A (en) * 1987-05-18 1990-02-13 The United States Of America, As Represented By The Secretary Of Agriculture Agents for non-formaldehyde durable press finishing and textile products therefrom
US6544296B2 (en) 2000-02-07 2003-04-08 The Proctor & Gamble Company Enhanced fabric comprising substrates and process to provide same
US6953485B2 (en) 2000-02-07 2005-10-11 Strike Investments, Llc Enhanced fabric comprising substrates and process to provide same
US20080194453A1 (en) * 2005-03-15 2008-08-14 Frank-Peter Lang Washing and Cleaning Agents Containing Acetales as Organic Solvents
US20090030241A1 (en) * 2005-03-15 2009-01-29 Frank-Peter Lang Novel Amphiphile Acetals
US20090031504A1 (en) * 2005-03-15 2009-02-05 Frank-Peter Lang Method for Chemically Cleaning Textile Material
US7632793B2 (en) 2005-03-15 2009-12-15 Clariant Produkte (Deutschland) Gmbh Washing and cleaning agents containing acetals as organic solvents

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Publication number Publication date
GB780043A (en) 1957-07-31
DE1084232B (de) 1960-06-30
BE534688A (lv)
CH330794A (fr) 1958-06-30
FR1133319A (fr) 1957-03-26

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