US2785949A - Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom - Google Patents

Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom Download PDF

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Publication number
US2785949A
US2785949A US403057A US40305754A US2785949A US 2785949 A US2785949 A US 2785949A US 403057 A US403057 A US 403057A US 40305754 A US40305754 A US 40305754A US 2785949 A US2785949 A US 2785949A
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US
United States
Prior art keywords
condensation product
cellulose
polymeric
bath
textile material
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
US403057A
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English (en)
Inventor
Bernard H Kress
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.)
QUAKER CHEMICAL PRODUCTS Corp
Original Assignee
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 NL193521D priority Critical patent/NL193521A/xx
Priority to BE534687D priority patent/BE534687A/xx
Priority to US403057A priority patent/US2785949A/en
Application filed by QUAKER CHEMICAL PRODUCTS CORP filed Critical QUAKER CHEMICAL PRODUCTS CORP
Priority to US403056A priority patent/US2786081A/en
Priority to GB36455/54A priority patent/GB776468A/en
Priority to FR1131435D priority patent/FR1131435A/fr
Priority to ES0219406A priority patent/ES219406A1/es
Priority to ES0222108A priority patent/ES222108A1/es
Priority to US625632A priority patent/US2878294A/en
Application granted granted Critical
Publication of US2785949A publication Critical patent/US2785949A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/53—Polyethers; Polyesters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/10—Saturated ethers of polyhydroxy compounds
    • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C11/00—Surface finishing of leather
    • C14C11/003—Surface finishing of leather using macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
    • D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers

Definitions

  • This invention relates to the application of certain acetal condensation products to cellulosic fabrics, yarns or fibers, such as rayon and cotton, in order to obtain dimensional control or stabilization of the fabric, yarn or fiber against progressive, dimensional shrinkage under repeated washings.
  • the present invention overcomes the foregoing difiiculties by providing aprocess in which no Objection- EXAMPLE 1 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 withdilute 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's 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 a linear polymeric structure. It has a specific gravity of 1.155 at 94 F.
  • the refractive index'is Polymeric condensation products may also be made starting with ethylene 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, eithr alone or in admixture with the aforementioned "glycols.
  • polyols such as glycerine, pentaerythritol and sorbitol
  • polyols such as glycerine, pentaerythritol and sorbitol
  • polyols such as glycerine, pentaerythritol and sorbitol
  • polyoxane, methylal, aqueous formalin and similar formaldeyde-generating compounds may be used.
  • aldehyde instead of formaldehyde, otherreactive aldehydes, such as acetaldehyde, propanal, butanal, benzaldehyde, glyoxal, terephthalaldehyde and other dialdehydes, may be used, containing not more than 8 carbon atoms in the monomeric form, and mixtures thereof; in forming watersoluble or water-dispersible condensation products with the alkylene glycols.
  • 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.
  • condensation products of this invention are of polymeric nature, as illustrated by the molecular weight of the product of Example 1.
  • polymeric I mean that my condensation products contain two or more aldehyde units and two or more polyhydric alcohol units per molecule of condensation product.
  • toluene present as an azeotropic liquid medium which does not interfere with the reaction.
  • azeotropic vehicles which may be used are benzene, xylene, ethyl benzene, and the like.
  • the treated fabric may then be dried at an appropriate temperature and subsequently cured at a temperature of at least 250 F. for about /2 to minutes. The time of 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 in a relaxed state. Fabrics so treated with these acetals will not on dergo progressive shrinkage even when laundered in boiling soap solution as in American Association of Textile Chemists and Colorists (A. A. T. C. C.) 1952 Standard Test Method 14-52 for cotton and linen fabrics.
  • EXAMPLE 3 In all cases treatment was similar to that described in The product has been found applicable to various weaves and combinations of rayon, as well as cotton. The following examples will serve to indicate the utility of the process.
  • Example 4 to 8 show results obtained by treating the specified textile materials as in Example 2 except where concentrations of the condensation product and catalyst are otherwise shown.
  • Example 1 These compounds were reacted as in Example 1.
  • the product was a somewhat viscous yellow liquid with a EXAMPLE 7 faint ethereal odor.
  • the product was soluble in water
  • the fabric was a,50% rayon and 50% acetate blend. and in toluelm
  • the following 'results were obtained on lightweight fiifi gg 40 shirting gabardine with equal weights of the various Sample acetalcondensation product described above (4.5%) and lwash Washes sodium sulfate-bisulfate (1 to 4) catalyst (3.0%).
  • the polymeric chains of the compounds of Untreated 4L5 my invention may be terminated, either in whole or in part, by means of an alkyl radical possessing not more efiects due to chlorme by the afore' than 8 carbon atoms.
  • the alkyl radical may be intromentioned standard test were observed in these samples.
  • EXAMPLE 14 P t s 11 r Parts in a e Product Used Pgdii ct Catalyst,percent r g Dlethylene glycol- 101 W h 5w h Beta methoxyethanoi 4 1 as as es Paraformaldehyde (91%) 30 d l a 0 0 N 9 2 11 e Toluene 20 giggfiti 1 III Sulfuric acid (90%) 0.1 D8: 810 9:6 114 The above materials were reacted as in Example 1 to 38"- g gflffff z 5:? yield a viscous liquid possessing a faint ethereal odor vDou'.
  • cellulose textile material is intended to include cellulose filaments and fibers, staple or yarns, Whether in finished stages or at some intermediate stage in the production thereof, of the group consisting of natural cellulose, regenerated cellulose, such as viscose rayon, cuprammonium rayon and hydrolyzed cellulose acetate, and mixtures thereof with other natural and synthetic fibers, such as cellulose acetate, nylon, wool, etc.
  • the term also includes fabrics, Whether knitted, woven or felted, as well as garments or other articles made from such fabrics.
  • the process of treating a cellulose textile material which comprises applying to a cellulose textile material an aqueousjbath containing an acidic catalyst and a polymeric acetal condensation product of a glycol selected from the group consisting of monoalkylene and polalkylene glycols in which the alkylene radical has 2 to 4 carbon atoms in a straight chain and mixtures of the aforesaid glycols, and a reactive aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydes containing not more than 8 carbon atoms in monomeric form and mixtures of the aforesaid aldehydes, said condensation product containing at least 2 aldehyde units and at least 2 polyhydric alcohol units per molecule of condensation product, said catalyst being present in amount from about 5% to about 200% by Weight of the said polymeric condensation product, said polymeric condensation product being present in said bath in amount from about 0.5% to about 25% by weight of the bath and heating the treated textile material at an elevated temperature until
  • the process of treating a cellulose textile material which comprises applying to a cellulose textile material an aqueous bath containing'an acidic catalyst and a polymeric acetal condensation product of a glycol select ed from the group consisting of monoalkylene and polyalkylene glycols in which the alkylene radical has 2 to 4 carbon atoms in a straight chain and mixtures of the aforesaid glycols, and a reactive aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydes containing not more than 8 carbon atoms in monomeric form and mixtures of the aforesaid aldehydes, said condensation product containing at least 2 aldehyde units and at least 2 polyhydric alcohol units per molecule of condensation product,- said catalyst being present in amount from about 5% to about 200% by weight of the said polymeric condensation product, said polymeric con densation product being present in said bath'in amount from about 0.5% to about 25 by Weight of the bath and heating the treated textile
  • the polymeric acetal condensation product in the bath is a polymeric condensation product of a glycol selected from the group consisting of monoalkylene and dialkylene glycols in which the alkylene radical has 2 to 4 carbon atoms, an aliphatic polyhydric alcohol containing from 3 to 6 hydroxyl groups and from 3 to 6 carbon atoms, and a reactive aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydes containing not mor than 8 carbon atoms in monomeric form.
  • a glycol selected from the group consisting of monoalkylene and dialkylene glycols in which the alkylene radical has 2 to 4 carbon atoms
  • an aliphatic polyhydric alcohol containing from 3 to 6 hydroxyl groups and from 3 to 6 carbon atoms
  • a reactive aldehyde selected from the group consisting of aliphatic and carbocyclic aldehydes containing not mor than 8 carbon atoms in monomeric form.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US403057A 1954-01-08 1954-01-08 Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom Expired - Lifetime US2785949A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
NL193521D NL193521A (xx) 1954-01-08
BE534687D BE534687A (xx) 1954-01-08
US403056A US2786081A (en) 1954-01-08 1954-01-08 Acetal condensation products
US403057A US2785949A (en) 1954-01-08 1954-01-08 Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom
GB36455/54A GB776468A (en) 1954-01-08 1954-12-16 Acetal condensation products and process for dimensional control of textile and paper materials
FR1131435D FR1131435A (fr) 1954-01-08 1955-01-06 Produits de condensation polymères et leurs applications
ES0219406A ES219406A1 (es) 1954-01-08 1955-01-07 UN PROCEDIMIENTO PARA LA PRODUCCIoN DE PRODUCTOS POLIMEROS
ES0222108A ES222108A1 (es) 1954-01-08 1955-05-30 Un procedimiento para estabilizar las dimensiones de productos textiles y de papel
US625632A US2878294A (en) 1954-01-08 1956-12-03 Polymeric acetals

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US403057A US2785949A (en) 1954-01-08 1954-01-08 Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom

Publications (1)

Publication Number Publication Date
US2785949A true US2785949A (en) 1957-03-19

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US403057A Expired - Lifetime US2785949A (en) 1954-01-08 1954-01-08 Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom

Country Status (6)

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US (1) US2785949A (xx)
BE (1) BE534687A (xx)
ES (1) ES222108A1 (xx)
FR (1) FR1131435A (xx)
GB (1) GB776468A (xx)
NL (1) NL193521A (xx)

Cited By (21)

* 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
US3015584A (en) * 1959-03-23 1962-01-02 Robert M Reinhardt Wrinkle resistance treatment for cellulosic textile fabrics
US3106439A (en) * 1959-01-17 1963-10-08 Tootal Broadhurst Lee Co Ltd Process of dry creaseproofing cellulosic fabrics with divinyl shlphone
DE1175197B (de) * 1961-06-28 1964-08-06 Algemene Kunstzijde Unie Nv Verfahren zur Verbesserung der Eigenschaften von Geweben oder Gewirken, die ganz oder teil-weise aus regenerierter Cellulose bestehen
US3145132A (en) * 1961-08-02 1964-08-18 Kendall & Co Woven stretchable fabrics
US3183054A (en) * 1959-07-24 1965-05-11 Shell Oil Co Aldehyde condensation products and their use in treating fibrous materials
US3227511A (en) * 1961-08-02 1966-01-04 Kendall & Co Methods of forming woven stretchable fabrics
US3312521A (en) * 1962-03-30 1967-04-04 Courtaulds Ltd Process of creaseproofing cellulose fibers with both glyoxal and formaldehyde
US3660009A (en) * 1969-02-02 1972-05-02 Millmaster Onyx Corp Method of manufacturing ready-to-wear crease-resistive garments
US4093666A (en) * 1974-02-06 1978-06-06 Hoechst Aktiengesellschaft Process for the manufacture of glycol ether formals
US4125652A (en) * 1976-05-20 1978-11-14 Sandoz Ltd. Treatment process for textile substrates comprising regenerated cellulose
US4172173A (en) * 1976-06-30 1979-10-23 Celanese Corporation Ethylene-vinyl acetate polymer binders for non-woven fabrics
US4189609A (en) * 1974-08-19 1980-02-19 Basf Wyandotte Corporation Multi-block coupled polyoxyalkylene copolymer surfactants
US4200564A (en) * 1976-05-20 1980-04-29 Sandoz Ltd. Aqueous preparations for treating textile substrates comprising regenerated cellulose
US4221562A (en) * 1978-05-04 1980-09-09 Scott Paper Company Bleed-fast cationic dyestuffs
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
WO2001057304A2 (en) * 2000-02-07 2001-08-09 The Procter & Gamble Company Enhanced fabric comprising substrates and process to provide same
WO2001057305A2 (en) * 2000-02-07 2001-08-09 The Procter & Gamble Company Enhanced fabric comprising substrates and process to provide same
CN113372519A (zh) * 2020-02-25 2021-09-10 中国石油大学(华东) 聚甲醛醇醚聚合物，其制备方法和用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4851291A (en) * 1986-06-19 1989-07-25 The United States Of America As Represented By The Secretary Of Agriculture Temperature adaptable textile fibers and method of preparing same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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 (26)

* 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
US3106439A (en) * 1959-01-17 1963-10-08 Tootal Broadhurst Lee Co Ltd Process of dry creaseproofing cellulosic fabrics with divinyl shlphone
US3015584A (en) * 1959-03-23 1962-01-02 Robert M Reinhardt Wrinkle resistance treatment for cellulosic textile fabrics
US3183054A (en) * 1959-07-24 1965-05-11 Shell Oil Co Aldehyde condensation products and their use in treating fibrous materials
DE1175197B (de) * 1961-06-28 1964-08-06 Algemene Kunstzijde Unie Nv Verfahren zur Verbesserung der Eigenschaften von Geweben oder Gewirken, die ganz oder teil-weise aus regenerierter Cellulose bestehen
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
US3312521A (en) * 1962-03-30 1967-04-04 Courtaulds Ltd Process of creaseproofing cellulose fibers with both glyoxal and formaldehyde
US3660009A (en) * 1969-02-02 1972-05-02 Millmaster Onyx Corp Method of manufacturing ready-to-wear crease-resistive garments
US4093666A (en) * 1974-02-06 1978-06-06 Hoechst Aktiengesellschaft Process for the manufacture of glycol ether formals
US4189609A (en) * 1974-08-19 1980-02-19 Basf Wyandotte Corporation Multi-block coupled polyoxyalkylene copolymer surfactants
US4125652A (en) * 1976-05-20 1978-11-14 Sandoz Ltd. Treatment process for textile substrates comprising regenerated cellulose
US4200564A (en) * 1976-05-20 1980-04-29 Sandoz Ltd. Aqueous preparations for treating textile substrates comprising regenerated cellulose
US4172173A (en) * 1976-06-30 1979-10-23 Celanese Corporation Ethylene-vinyl acetate polymer binders for non-woven fabrics
US4221562A (en) * 1978-05-04 1980-09-09 Scott Paper Company Bleed-fast cationic dyestuffs
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
WO2001057304A2 (en) * 2000-02-07 2001-08-09 The Procter & Gamble Company Enhanced fabric comprising substrates and process to provide same
WO2001057305A2 (en) * 2000-02-07 2001-08-09 The Procter & Gamble Company Enhanced fabric comprising substrates and process to provide same
WO2001057305A3 (en) * 2000-02-07 2001-12-06 Procter & Gamble Enhanced fabric comprising substrates and process to provide same
US20010049244A1 (en) * 2000-02-07 2001-12-06 Gardner Robb Richard Enhanced fabric comprising substrates and process to provide same
WO2001057304A3 (en) * 2000-02-07 2001-12-20 Procter & Gamble Enhanced fabric comprising substrates and process to provide same
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
CN113372519A (zh) * 2020-02-25 2021-09-10 中国石油大学(华东) 聚甲醛醇醚聚合物，其制备方法和用途

Also Published As

Publication number Publication date
NL193521A (xx)
GB776468A (en) 1957-06-05
ES222108A1 (es) 1956-01-01
FR1131435A (fr) 1957-02-21
BE534687A (xx)

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