US2730427A - Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds - Google Patents

Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds Download PDF

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Publication number
US2730427A
US2730427A US304229A US30422952A US2730427A US 2730427 A US2730427 A US 2730427A US 304229 A US304229 A US 304229A US 30422952 A US30422952 A US 30422952A US 2730427 A US2730427 A US 2730427A
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Prior art keywords
diglycidyl ether
cellulosic
compound
cloth
ether
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US304229A
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Suen Tzeng Jiueq
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Wyeth Holdings LLC
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American Cyanamid Co
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    • 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
    • D06M13/11—Compounds containing epoxy groups or precursors thereof
    • 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
    • D06M15/55—Epoxy resins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/08—Oxirane

Definitions

  • This invention relates to a process of rendering textile materials substantially resistant to shrinkage and creasing. It is an object of the invention to provide a process for rendering cotton, wool, rayon and other fibrous textile materialscontaining functional groups substantially rewherein R is an alkylene group of from 2 to 6 carbon atoms, inclusive, drying the impregnated textile material and curing the compound in situ. Preferably one should use about -15% by weight based on the dry weight of the textile material.
  • the impregnation step may be conveniently accomplished by means well-known in the art, for example, the textile material may be passed through or dipped in a solution of the compound in water or any other solvent in which the compound is soluble.
  • the step of drying the material can be performed by any conventional means, such as by heating in a forced air dryer.
  • heating is not essential for the purpose of drying and the drying may be readily accomplished by merely allowing the material to remain in contact with the atmospheric air for a short period of time.
  • the curing step is preferably accomplished by heating, and if desired, the drying and curing steps may be consolidated.
  • the curing step effects the opening of the epoxy ring in the compound thereby causing the compound to react with the functional groups of the fibrous material being treated. In this matter the compound is firmly united with the fabric and becomes insolubilized.
  • the preferred temperature is from 50 C. to 200 C.
  • the rapidity of curing can be accelerated, if desired, by incorporating a substance having a catalytic effect in the impregnating solution, a1- though this is not at all necessary.
  • catalysts such as oxalic acid, sodium carbonate, aluminum chloride, ammonium chloride, diammonium phosphate or hexamethylenetetramine and the like.
  • Example 1 A piece of 80 x 80 cotton percale is dipped in a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 1% of a mixture containing 30 parts of diammonium phosphate and 4 parts of hexamethylenetetramine. The wet cloth is then dried by hanging it in contact with atmospheric air. By weighing the dried cloth, it is determined that 6.2% of bis-glycidyl ether based on the weight of the cloth has been picked up. Curing is efiected by heating the cloth at 350 F. for 10 minutes. The warp shrinkage of this treated cloth after washing for one hour is 3.1%. The corresponding Warp shrinkage figures for a piece of untreated cloth from the same roll after 1 hour and 3 hour washes are 6.7% and 7.9%, respectively. The crease resistance of the treated cloth is also improved.
  • Example 2 A piece of wool serge cloth is treated with a 10% solution of hexamethyleneglycol bis-glycidyl ether in water. The wet cloth is dried in a forced air current at 40 C. for 20 minutes. The dried cloth shows a dry pick-up of 7.5% of the hexamethyleneglycol bis-glycidyl ether. The dried cloth is heated at 300 F. for 30 minutes to effect the curing of the compound. Shrinkage tests show that the treated cloth as approximately 6 the shrinkage value of a piece of untreated cloth from the same roll.
  • Example 3 A piece of x 80 cotton percale is treated with a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 0.5% of oxalic acid. The treated cloth, with about Wet pick-up, is dried and cured at 290 F. for 6 minutes. The warp shrinkage of this treated cloth after Washing for 1 hour is 2.5% and that after 3 hour washing is 2.8%. The correspond ing figures for the untreated cloth are 5.3% and 5.6%, respectively.
  • the bis-glycidyl ethers employed in this invention may be conveniently prepared by the reaction of the corresponding glycol and epichlorohydrin.
  • ethylene glycol bis-glycidyl ether ethylene glycol may be condensed with an excess of epichlorohydrin in the presence of concentrated sulfuric acid as a catalyst to form the addition compound having the formula
  • the acid catalyst may be neutralized with barium carbonate or other alkali and removed by filtration.
  • the excess of epichlorohydrin may be removed by distillation.
  • the addition compound can then be treated with caustic solution in Water at room temperature, whereby it is converted into the epoxy compound.
  • the compounds which can be used to treat the textile materials in accordance with the present invention are ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, trimethylene glycol diglycidyl ether, 1,4- butanediol diglycidyl ether, 1,3-butanediol diglycidyl ether, 2,3-butanediol diglycidyl ether, 1,5-pentanediol diglycidyl ether, 2,4-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 2,5-hexanediol diglycidyl ether, 2-methyl-2,4-pentanediol diglycidyl ether and the like.
  • a process of impregnating a textile material selected from the group consisting of cellulosic and wool materials comprising impregnating said textile material with an aqueous solution of a compound having the formula where R is. an alkylene radical of from 2 to 6 carbon atoms in sufficient amount to deposit on said textile material between about 2 and about 30 per cent of said compound based on the dry weight of said textile material, drying said impregnated material and curing said compound to a Water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrink-resistant textile material.
  • a process which comprises impregnating a cotton fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said cotton fabric, drying said impregnated cotton fabric and curing said ether to a Water-insoluble state by heating at a temperature between about and about 200 degrees Centigrade to produce a flexible shrinkresistant cotton fabric.
  • a process which comprises impregnating a wool fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said woolen fabric, drying said impregnated wool fabric and curing said ether to a water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrinkresistant wool fabric.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

SAGE CONTROL OF CELLULOSIC AND WQOL TEXTILES WITH DIGLYCIDYL ETHER COOUNDS Tzeng .iiueq Suen, Stamford, Conn., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application August 13, 1952, Serial No. 304,229
7 Claims. (Cl. 8-116) This invention relates to a process of rendering textile materials substantially resistant to shrinkage and creasing. It is an object of the invention to provide a process for rendering cotton, wool, rayon and other fibrous textile materialscontaining functional groups substantially rewherein R is an alkylene group of from 2 to 6 carbon atoms, inclusive, drying the impregnated textile material and curing the compound in situ. Preferably one should use about -15% by weight based on the dry weight of the textile material.
The impregnation step may be conveniently accomplished by means well-known in the art, for example, the textile material may be passed through or dipped in a solution of the compound in water or any other solvent in which the compound is soluble.
The step of drying the material can be performed by any conventional means, such as by heating in a forced air dryer. However, heating is not essential for the purpose of drying and the drying may be readily accomplished by merely allowing the material to remain in contact with the atmospheric air for a short period of time.
The curing step is preferably accomplished by heating, and if desired, the drying and curing steps may be consolidated. The curing step, in theory, effects the opening of the epoxy ring in the compound thereby causing the compound to react with the functional groups of the fibrous material being treated. In this matter the compound is firmly united with the fabric and becomes insolubilized. There are no particularly critical conditions required for the curing step. The preferred temperature is from 50 C. to 200 C. The rapidity of curing can be accelerated, if desired, by incorporating a substance having a catalytic effect in the impregnating solution, a1- though this is not at all necessary. However, if it is desired to employ a catalyst, an acid or an alkali, or any substance having a latent acid or alkaline effect, will accelerate 'the cure. Thus, there may be used as catalysts compounds such as oxalic acid, sodium carbonate, aluminum chloride, ammonium chloride, diammonium phosphate or hexamethylenetetramine and the like.
In order to more fully illustrate this invention the following examples are given. Parts are by weight unless otherwise specified.
Example 1 A piece of 80 x 80 cotton percale is dipped in a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 1% of a mixture containing 30 parts of diammonium phosphate and 4 parts of hexamethylenetetramine. The wet cloth is then dried by hanging it in contact with atmospheric air. By weighing the dried cloth, it is determined that 6.2% of bis-glycidyl ether based on the weight of the cloth has been picked up. Curing is efiected by heating the cloth at 350 F. for 10 minutes. The warp shrinkage of this treated cloth after washing for one hour is 3.1%. The corresponding Warp shrinkage figures for a piece of untreated cloth from the same roll after 1 hour and 3 hour washes are 6.7% and 7.9%, respectively. The crease resistance of the treated cloth is also improved.
Example 2 A piece of wool serge cloth is treated with a 10% solution of hexamethyleneglycol bis-glycidyl ether in water. The wet cloth is dried in a forced air current at 40 C. for 20 minutes. The dried cloth shows a dry pick-up of 7.5% of the hexamethyleneglycol bis-glycidyl ether. The dried cloth is heated at 300 F. for 30 minutes to effect the curing of the compound. Shrinkage tests show that the treated cloth as approximately 6 the shrinkage value of a piece of untreated cloth from the same roll.
Example 3 A piece of x 80 cotton percale is treated with a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 0.5% of oxalic acid. The treated cloth, with about Wet pick-up, is dried and cured at 290 F. for 6 minutes. The warp shrinkage of this treated cloth after Washing for 1 hour is 2.5% and that after 3 hour washing is 2.8%. The correspond ing figures for the untreated cloth are 5.3% and 5.6%, respectively.
The bis-glycidyl ethers employed in this invention may be conveniently prepared by the reaction of the corresponding glycol and epichlorohydrin. For example, in the preparation of ethylene glycol bis-glycidyl ether, ethylene glycol may be condensed with an excess of epichlorohydrin in the presence of concentrated sulfuric acid as a catalyst to form the addition compound having the formula The acid catalyst may be neutralized with barium carbonate or other alkali and removed by filtration. The excess of epichlorohydrin may be removed by distillation. The addition compound can then be treated with caustic solution in Water at room temperature, whereby it is converted into the epoxy compound.
Many modifications may be made in the process without departing from the spirit and scope of the invention. For instance, other substances may be incorporated in the impregnating bath for the purpose of modifying the hand of the textile material or far the purpose of ren dering the material water-repellent. Other modifications will be apparent to those skilled in the art.
Amongst the compounds which can be used to treat the textile materials in accordance with the present invention are ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, trimethylene glycol diglycidyl ether, 1,4- butanediol diglycidyl ether, 1,3-butanediol diglycidyl ether, 2,3-butanediol diglycidyl ether, 1,5-pentanediol diglycidyl ether, 2,4-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 2,5-hexanediol diglycidyl ether, 2-methyl-2,4-pentanediol diglycidyl ether and the like.
I claim:
1. A process of impregnating a textile material selected from the group consisting of cellulosic and wool materials, said process comprising impregnating said textile material with an aqueous solution of a compound having the formula where R is. an alkylene radical of from 2 to 6 carbon atoms in sufficient amount to deposit on said textile material between about 2 and about 30 per cent of said compound based on the dry weight of said textile material, drying said impregnated material and curing said compound to a Water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrink-resistant textile material.
2. The process of claim 1 in which said compound is ethylene glycol bis-glycidyl ether.
3. The process of claim 1 in which said textile material comprises cotton.
4. The process of claim 1 in which said deposit amounts to between about and about per cent of the dry weight of said textile material.
5. The process of claim 1 in which said aqueous solution contains a curing catalyst for said ether compound.
6. A process which comprises impregnating a cotton fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said cotton fabric, drying said impregnated cotton fabric and curing said ether to a Water-insoluble state by heating at a temperature between about and about 200 degrees Centigrade to produce a flexible shrinkresistant cotton fabric.
7. A process which comprises impregnating a wool fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said woolen fabric, drying said impregnated wool fabric and curing said ether to a water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrinkresistant wool fabric.
References Cited in the file of this patent UNITED STATES PATENTS 2,131,120 Schlack Sept. 27, 1938 2,252,039 Schirm Aug. 12, 1941 2,500,449 Bradley Mar. 14, 1950 2,500,600 Bradley Mar. 14, 1950 2,606,810 Erickson et al. Aug. 12, 1952

Claims (1)

1. A PROCESS OF IMPREGNATING A TEXTILE MATERIAL SELECTED FROM THE GROUP CONSISTING OF CELLULOSIC AND WOOL MATERIALS, SAID PROCESS COMPRISING IMPREGNATING SAID TEXTILE MATERIAL WITH AN AQUEOUS SOLUTION OF A COMPOUND HAVING THE FORMULA
US304229A 1952-08-13 1952-08-13 Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds Expired - Lifetime US2730427A (en)

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2869970A (en) * 1957-04-11 1959-01-20 Edward M Filachione Tanning with epoxy resins
US2886402A (en) * 1958-05-12 1959-05-12 Thompson J Coe Shrinkproofing textiles with polyepoxides and ammonia
US2933409A (en) * 1958-08-14 1960-04-19 Charles H Binkley Method for imparting permanent deformation to textiles
US2933366A (en) * 1958-05-12 1960-04-19 Thompson J Coe Shrinkproofing textiles with polyepoxides, polyamides, and ammonia
US2951854A (en) * 1957-06-12 1960-09-06 Gen Aniline & Film Corp Bis-epoxides obtained from 2, 2, 3, 3-tetrahalo-1, 4-butanediol and methods of manufacture of the same
DE1094225B (en) * 1955-02-22 1960-12-08 Courtaulds Inc Process for crease and shrink-proof finishing of cellulose textiles
US2971815A (en) * 1957-10-31 1961-02-14 Austin L Bullock Chemically modified textiles
US2993915A (en) * 1959-02-06 1961-07-25 Rohm & Haas Tetrahydrofuryl and tetrahydrofurfuryl glycidyl ethers
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
DE1138732B (en) * 1956-08-08 1962-10-31 Boehme Fettchemie Gmbh Process for improving the hydrophilicity and antistatic properties of molded articles made of synthetic polyamides
US3073662A (en) * 1963-01-15 Process for the production of fast dye-
US3102774A (en) * 1961-10-05 1963-09-03 Nathan H Koenig Treatment of wool with epoxides in the presence of dimethylformamide
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3173750A (en) * 1960-10-19 1965-03-16 Deering Milliken Res Corp Method of imparting wet and dry crease recovery to cellulose textile fabric
US3175874A (en) * 1959-01-29 1965-03-30 Deering Milliken Res Corp Method of creaseproofing cellulosic fabrics by wet creaseproofing followed by dry creaseproofing and the resulting product
US3175875A (en) * 1960-04-25 1965-03-30 Deering Milliken Res Corp Cellulosic fabrics and methods for making the same
US3203912A (en) * 1959-10-01 1965-08-31 Grace W R & Co Process for waterproofing of cellulosic materials
US3206328A (en) * 1960-03-01 1965-09-14 American Cyanamid Co Process for imparting anti-static properties to hydrophobic textile materials and product thereof
US3219407A (en) * 1960-06-01 1965-11-23 Hoechst Ag Vinyl phosphonic acid polymers and derivatives thereof as acidic catalysts in a process of creaseproofing cellulose textiles
DE1221188B (en) * 1956-04-03 1966-07-21 Deering Milliken Research Corporation, Spartanburg, S. C. (V. St. A.) Process for improving the smooth drying capacity of cellulosic yarns or fabrics
US3279882A (en) * 1964-07-07 1966-10-18 Stevens & Co Inc J P Process of stabilizing proteinaceous materials through treatment with a polyethyleneimine and a polyaziridine
US3281203A (en) * 1961-06-15 1966-10-25 Montedison Spa Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst
US4087246A (en) * 1976-03-04 1978-05-02 Allied Chemical Corporation Fiber modification compositions and process
US4137399A (en) * 1976-10-02 1979-01-30 Dynamit Nobel Aktiengesellschaft Method of preparing functionalized celluloses
US5665123A (en) * 1993-04-15 1997-09-09 Nippon Sanmo Sensyoku Co., Ltd. Modified wool and process of imparting shrink-proofing property to wool
US20130115259A1 (en) * 2010-01-21 2013-05-09 The University Of South Dakota Polymeric systems for delivering hypohalide salts
CN106496162A (en) * 2016-09-05 2017-03-15 南京工业大学 2,3 butanediol diglycidyl ethers and preparation method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2131120A (en) * 1934-11-01 1938-09-27 Ig Farbenindustrie Ag Manufacture of organic compounds containing basic substituents
US2252039A (en) * 1936-06-30 1941-08-12 Heberlein Patent Corp Process of rendering textiles water repellent
US2500600A (en) * 1948-02-28 1950-03-14 Shell Dev Compositions of matter containing epoxy ethers and diamines
US2606810A (en) * 1949-09-28 1952-08-12 American Cyanamid Co Treatment of wool-containing textile materials and products thereof
US7500449B2 (en) * 2004-07-29 2009-03-10 Woodstream Corporation Bird house assembly

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2131120A (en) * 1934-11-01 1938-09-27 Ig Farbenindustrie Ag Manufacture of organic compounds containing basic substituents
US2252039A (en) * 1936-06-30 1941-08-12 Heberlein Patent Corp Process of rendering textiles water repellent
US2500600A (en) * 1948-02-28 1950-03-14 Shell Dev Compositions of matter containing epoxy ethers and diamines
US2606810A (en) * 1949-09-28 1952-08-12 American Cyanamid Co Treatment of wool-containing textile materials and products thereof
US7500449B2 (en) * 2004-07-29 2009-03-10 Woodstream Corporation Bird house assembly

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3073662A (en) * 1963-01-15 Process for the production of fast dye-
DE1094225B (en) * 1955-02-22 1960-12-08 Courtaulds Inc Process for crease and shrink-proof finishing of cellulose textiles
DE1221188B (en) * 1956-04-03 1966-07-21 Deering Milliken Research Corporation, Spartanburg, S. C. (V. St. A.) Process for improving the smooth drying capacity of cellulosic yarns or fabrics
DE1138732B (en) * 1956-08-08 1962-10-31 Boehme Fettchemie Gmbh Process for improving the hydrophilicity and antistatic properties of molded articles made of synthetic polyamides
US2869970A (en) * 1957-04-11 1959-01-20 Edward M Filachione Tanning with epoxy resins
US2951854A (en) * 1957-06-12 1960-09-06 Gen Aniline & Film Corp Bis-epoxides obtained from 2, 2, 3, 3-tetrahalo-1, 4-butanediol and methods of manufacture of the same
US2971815A (en) * 1957-10-31 1961-02-14 Austin L Bullock Chemically modified textiles
US2886402A (en) * 1958-05-12 1959-05-12 Thompson J Coe Shrinkproofing textiles with polyepoxides and ammonia
US2933366A (en) * 1958-05-12 1960-04-19 Thompson J Coe Shrinkproofing textiles with polyepoxides, polyamides, and ammonia
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
US2933409A (en) * 1958-08-14 1960-04-19 Charles H Binkley Method for imparting permanent deformation to textiles
US3175874A (en) * 1959-01-29 1965-03-30 Deering Milliken Res Corp Method of creaseproofing cellulosic fabrics by wet creaseproofing followed by dry creaseproofing and the resulting product
US2993915A (en) * 1959-02-06 1961-07-25 Rohm & Haas Tetrahydrofuryl and tetrahydrofurfuryl glycidyl ethers
US3203912A (en) * 1959-10-01 1965-08-31 Grace W R & Co Process for waterproofing of cellulosic materials
US3206328A (en) * 1960-03-01 1965-09-14 American Cyanamid Co Process for imparting anti-static properties to hydrophobic textile materials and product thereof
US3175875A (en) * 1960-04-25 1965-03-30 Deering Milliken Res Corp Cellulosic fabrics and methods for making the same
US3219407A (en) * 1960-06-01 1965-11-23 Hoechst Ag Vinyl phosphonic acid polymers and derivatives thereof as acidic catalysts in a process of creaseproofing cellulose textiles
US3173750A (en) * 1960-10-19 1965-03-16 Deering Milliken Res Corp Method of imparting wet and dry crease recovery to cellulose textile fabric
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3281203A (en) * 1961-06-15 1966-10-25 Montedison Spa Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst
US3102774A (en) * 1961-10-05 1963-09-03 Nathan H Koenig Treatment of wool with epoxides in the presence of dimethylformamide
US3279882A (en) * 1964-07-07 1966-10-18 Stevens & Co Inc J P Process of stabilizing proteinaceous materials through treatment with a polyethyleneimine and a polyaziridine
US4087246A (en) * 1976-03-04 1978-05-02 Allied Chemical Corporation Fiber modification compositions and process
US4137399A (en) * 1976-10-02 1979-01-30 Dynamit Nobel Aktiengesellschaft Method of preparing functionalized celluloses
US5665123A (en) * 1993-04-15 1997-09-09 Nippon Sanmo Sensyoku Co., Ltd. Modified wool and process of imparting shrink-proofing property to wool
US20130115259A1 (en) * 2010-01-21 2013-05-09 The University Of South Dakota Polymeric systems for delivering hypohalide salts
US9700040B2 (en) * 2010-01-21 2017-07-11 The University Of South Dakota Polymeric systems for delivering hypohalide salts
CN106496162A (en) * 2016-09-05 2017-03-15 南京工业大学 2,3 butanediol diglycidyl ethers and preparation method thereof

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