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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- acetal
- textile material
- carbon atoms
- cellulose
- acetals
- 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
Links
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B13/00—Machines and apparatus for drying fabrics, fibres, yarns, or other materials in long lengths, with progressive movement
- F26B13/001—Drying and oxidising yarns, ribbons or the like
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating 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
- D06M13/137—Acetals, 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
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE534688D BE534688A (it) | 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 |
CH331749D CH331749A (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 |
CH332705D CH332705A (de) | 1953-05-08 | 1954-05-03 | Verfahren zur Herstellung organischer Verbindungen |
CH332481D CH332481A (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 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2785947A true US2785947A (en) | 1957-03-19 |
Family
ID=26709251
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US411542A Expired - Lifetime US2785947A (en) | 1947-03-05 | 1954-01-08 | Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom |
Country Status (6)
Country | Link |
---|---|
US (1) | US2785947A (it) |
BE (1) | BE534688A (it) |
CH (1) | CH330794A (it) |
DE (1) | DE1084232B (it) |
FR (1) | FR1133319A (it) |
GB (1) | GB780043A (it) |
Cited By (22)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2079360A1 (en) * | 1991-09-30 | 1993-03-31 | Anna Maria Czech | Method of imparting durable press properties to cotton textiles without using formaldehyde |
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)
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)
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 |
LU30813A1 (it) * | 1950-07-11 | |||
US2643236A (en) * | 1950-12-29 | 1953-06-23 | American Cyanamid Co | Method of preparing condensation products of pentaerythritol and glyoxal |
-
0
- BE BE534688D patent/BE534688A/xx unknown
-
1954
- 1954-01-08 US US411542A patent/US2785947A/en not_active Expired - Lifetime
- 1954-12-16 GB GB36456/54A patent/GB780043A/en not_active Expired
-
1955
- 1955-01-06 FR FR1133319D patent/FR1133319A/fr not_active Expired
- 1955-01-07 DE DEA21872A patent/DE1084232B/de active Pending
- 1955-01-08 CH CH330794D patent/CH330794A/fr unknown
Patent Citations (6)
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)
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 |
Also Published As
Publication number | Publication date |
---|---|
BE534688A (it) | |
GB780043A (en) | 1957-07-31 |
FR1133319A (fr) | 1957-03-26 |
CH330794A (fr) | 1958-06-30 |
DE1084232B (de) | 1960-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2785947A (en) | Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom | |
US2785949A (en) | Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom | |
US4396391A (en) | Treating cellulose textile fabrics with dimethylol dihydroxyethyleneurea-polyol | |
US3236676A (en) | Treatment of cellulose with tetrakis (hydroxymethyl) phosphonium resins | |
US3852829A (en) | Composition and method for producing wrinkle-free permanently pressed cellulosic textile materials | |
US3597147A (en) | Modification of cellulosic textile materials with pyrimidones | |
US2412832A (en) | Textile material and method of preparing it | |
US2846337A (en) | Magnesium chloride catalyst for modified urea resins | |
US3420696A (en) | Aldehyde fixation on polymeric material | |
US3052570A (en) | Textile finishing resin, wrinkle resistant cellulose textile, processes of making resin and treated textile | |
US3063869A (en) | Novel textile finishing compositions and process for using the same | |
US3914229A (en) | Novel N-hydroxymethyl compounds, compositions containing such compounds and cellulose-containing textile materials treated therewith | |
US2785948A (en) | Process for stabilizing cellulose textile materials against dimensional changes by applying simple acetals and products resulting therefrom | |
US2739908A (en) | Method of impregnating textile fabric with resin | |
US3983269A (en) | Durable press composition and process | |
US2889192A (en) | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor | |
US3502672A (en) | Hexahydropyrimidone derivatives | |
US2885443A (en) | Water-soluble acetals of glutaralde-hyde and method of making same | |
US3576591A (en) | Methylolated cyclic urea compositions containing sodium formate or sodium tetraborate | |
US2903328A (en) | Process for the dimensional control of cellulosic materials | |
US3984367A (en) | Durable press composition and process | |
US3215489A (en) | Process of treating cellulose textile material | |
US2945738A (en) | Low cover factor woven cellulose textile material resistant to corrugation in washing and tumble drying | |
GB846287A (en) | Methods for imparting to cellulosic fabric a drip-dry crease-resistant finish | |
DE2242689A1 (de) | Verfahren zur herstellung von phosphorhaltigen kondensationsprodukten, die produkte und ihre verwendung als flammschutzmittel |