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GB897757A - 1, 3-di-methylol-4, 5-bis(alkoxy)-2-imidazolidinones and use of the same - Google Patents

1, 3-di-methylol-4, 5-bis(alkoxy)-2-imidazolidinones and use of the same

Info

Publication number
GB897757A
GB897757A GB602060A GB602060A GB897757A GB 897757 A GB897757 A GB 897757A GB 602060 A GB602060 A GB 602060A GB 602060 A GB602060 A GB 602060A GB 897757 A GB897757 A GB 897757A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
imidazolidinone
fabric
methylol
crease
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
Application number
GB602060A
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB897757A publication Critical patent/GB897757A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
    • Y10T442/277—Coated or impregnated cellulosic fiber fabric

Landscapes

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

Abstract

Aqueous solutions containing 1,3-dimethylol-4,5-di(alkoxy)-2-imidazolidinone of general formula <FORM:0897757/IV (a)/1> wherein the R groups are alkyl radicals with from 1 to 5 carbon atoms, and an acidic catalyst when impregnated on a textile fabric and heated form a thermoset product which produces crease resistance in the fabric. Catalysts such as zinc nitrate, magnesium chloride, ammonium phosphate, and sulphate and the mineral acid salts of 2-amino-2-methylpropanol-1 and ethanolamine are mentioned and in an example cotton cloth was impregnated with the aid of a zinc nitrate catalyst. Specification 720,386 is referred to.ALSO:The invention comprises 1,3-dimethylol-4,5-di(alkoxy)-2-imidazolidinones of formula <FORM:0897757/IV (b)/1> where R represents alkyl groups containing from 1 to 5 carbon atoms. They are prepared by reacting a 4,5-di(alkoxy)-2-imidazolidinone <FORM:0897757/IV (b)/2> with formaldehyde or a substance generating formaldehyde, in alkaline or neutral medium, for example at between 0 DEG C. and 100 DEG C. and a pH above 8. The reaction may be in aqueous or organic solvent medium and formalin is preferred, and sodium, potassium, calcium or barium hydroxides or a lower alkylamine or alkylamineol may be the alkalizing agent. Examples describe the preparation of 1,3-di(methylol)-4,5-di(methoxy), (ethoxy) and (butoxy), and the treatment of cellulose fabrics with aqueous solutions of 1,3-di (methylol) - 4,5 - di (methoxy) - 2 - imidazolidione by impregnating therewith and heating. Fabrics treated with the products show increased chlorine resistance and superior crease-resistant properties and fastness to light. The preparation of 4,5-di(alkoxy)-2-imidazolidinones by the alkyletherification of 4.5.-dihydroxy-2-imidazolidinone with an aliphatic lower alcohol in an acidic medium by a batch or continuous process is also described. Specification 720,386 is referred to.ALSO:Crease-resistant textile fabrics are obtained by impregnating the fabric, e.g. cotton, with an aqueous solution of a 1,3-dimethylol-4,5-di-(alkoxy)-2-imidazolidinone of the formula <FORM:0897757/IV (c)/1> where each R represents an alkyl group containing from 1 to 5 carbon atoms, (see Group IV (a)) and an acidic catalyst, drying and heating to thermoset the compound. Curing catalysts may be inorganic salts such as zinc nitrate, magnesium chloride, ammonium phosphosphate or sulphate or salts of 2-amino-2-methylpropanol-1 or ethanolamine. The properties of the treated fabric may be varied by selecting the chain length of the two alkoxy groups in the 4 and 5 positions. Softening agents and water repellents may be included in the impregnation baths. An example describes the treatment of cotton fabric with a 50% aqueous solution of 1,3 - di(methylol)-4,5-di(methoxy)-2 - imidazolidinone containing zinc nitrate. The fabrics are pre-dried at 105 DEG C. and heated to 140 DEG C. The products show increased chlorine resistance as well as crease-resistant properties. Specification 720,386 is referred to.
GB602060A 1959-03-12 1960-02-19 1, 3-di-methylol-4, 5-bis(alkoxy)-2-imidazolidinones and use of the same Expired GB897757A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP792359 1959-03-12
JP874059 1959-03-18
JP910859 1959-03-20
JP2448059 1959-07-29

Publications (1)

Publication Number Publication Date
GB897757A true GB897757A (en) 1962-05-30

Family

ID=27454825

Family Applications (1)

Application Number Title Priority Date Filing Date
GB602060A Expired GB897757A (en) 1959-03-12 1960-02-19 1, 3-di-methylol-4, 5-bis(alkoxy)-2-imidazolidinones and use of the same

Country Status (4)

Country Link
US (1) US3029164A (en)
CH (1) CH402875A (en)
DE (1) DE1190425B (en)
GB (1) GB897757A (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260565A (en) * 1961-02-03 1966-07-12 American Cyanamid Co Novel imidazolidinones and their use as textile finishing agents
US3091617A (en) * 1961-02-03 1963-05-28 American Cyanamid Co Process for preparing 4, 5-dialkoxy-1, 3-dialkyl-2-imidazolidinones
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins
US3376101A (en) * 1963-10-22 1968-04-02 Agriculture Usa Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products
US3383390A (en) * 1965-02-11 1968-05-14 Agriculture Usa Reaction of dimethyloldihydroxyethyleneurea with p-dioxane and reaction product
GB1103285A (en) * 1966-02-20 1968-02-14 Ici Ltd Imidazolidine derivatives
CH1258167D (en) * 1966-09-08
US3890095A (en) * 1967-04-05 1975-06-17 American Cyanamid Co Cellulosic textile finish with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent
US20050215145A1 (en) * 2004-03-25 2005-09-29 Guerrero Cesar H Liquid resistant articles and method of producing the same
CN115559114A (en) * 2022-10-13 2023-01-03 浙江宏都寝具有限公司 High-modulus low-shrinkage garment fabric and preparation process thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2373136A (en) * 1943-11-23 1945-04-10 Du Pont Ethylene urea derivatives
BE485410A (en) * 1948-04-26
FR1010099A (en) * 1948-04-26 1952-06-13 Bozel Maletra Water-soluble condensation products for textile finishing
US2661312A (en) * 1951-06-14 1953-12-01 Du Pont Textile finishing composition and method of treating textile materials therewith
DE910475C (en) * 1951-08-17 1954-05-03 Basf Ag Process for the production of nitrogen-containing condensation products
BE513352A (en) * 1951-08-18
US2898238A (en) * 1956-08-20 1959-08-04 American Cyanamid Co Process for treating textiles with ethylene urea-formaldehyde reaction products
US2911326A (en) * 1956-11-08 1959-11-03 Du Pont Treatment of cellulosic fiber and composition therefor

Also Published As

Publication number Publication date
DE1190425B (en) 1965-04-08
US3029164A (en) 1962-04-10
CH402875A (en) 1965-11-30

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