US3503793A - Cellulosic fibrous materials - Google Patents

Cellulosic fibrous materials Download PDF

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Publication number
US3503793A
US3503793A US3503793DA US3503793A US 3503793 A US3503793 A US 3503793A US 3503793D A US3503793D A US 3503793DA US 3503793 A US3503793 A US 3503793A
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US
United States
Prior art keywords
compounds
fireproofing
compound
cellulosic fibrous
fibrous 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
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English (en)
Inventor
Hans Brandeis
Klaus Pfleger
Heinz Bille
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BASF SE
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BASF SE
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Publication date
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Publication of US3503793A publication Critical patent/US3503793A/en
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Classifications

    • 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
    • D06M13/322—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 nitrogen
    • D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/564—Three-membered rings
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/92—Fire or heat protection feature
    • Y10S428/921—Fire or flameproofing
    • 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
    • Y10T442/2631—Coating or impregnation provides heat or fire protection
    • Y10T442/2672—Phosphorus containing
    • Y10T442/268—Phosphorus and nitrogen containing compound

Definitions

  • the present invention relates to a process for the fireproofing of cellulosic fibrous material using certain phosphorus amides and chloromethyl phosphonarnides and to the cellulosic material finished in this way.
  • the amides particularly the dialkylamides and the 1,2- alkylenamides of phosphoric acid and of alkylphosphonic acids and haloalkylphosphonic acids, are generally known as fireproofing agents for cellulosic fibrous material.
  • CHzCl which moreover are very toxic in the unchanged, i.e. unfixed, condition.
  • phosphoric amides and phosphonic amides including the nontoxic compounds phosphoric-tris-methylarnide and chloromethylphosphonic-bis-methylamide
  • the object of the present invention is to provide new fireproofing agents for cellulosic fibrous materials which give optimum and wash-resistant fireproofing effects with a minimum of deleterious secondary effects.
  • cellulosic fibrous materials can be given a wash-resistant fireproof finish by means of phosphoric amides of chloromethylphosphonic amides with excellent success by applying to the fibrous material a composition containing or consisting of a mixture of compounds (I) and (II) defined by the following general formulae:
  • the mixtures of compounds (I) and (II), which are referred to hereinafter as compounds for simplicity, are obtainable by conventional methods, preferably by reaction of 1 mole each of phosphorus oxychloride or chloromethyl-phosphonyl dichloride with m or n moles of methylamine and 3-m or 2-n moles of ethylenimine in an inert organic solution at temperatures of from about -40 C. to +40 C. It is recommended that the solvent (for example methylene chloride, benzene, dioxane, tetrahydrofuran of ether) be placed in a reactor and the reactants be passed into the same simultaneously at the same rate in proportion to the molar composition of the product.
  • solvent for example methylene chloride, benzene, dioxane, tetrahydrofuran of ether
  • the new agents are advantageously used in 5 to 50% aqueous solution (percentages here and hereinafter being by weight) for finishing cellulosic fibrous materials, the amount being such that the fibrous material absorbs from about 5 to 50%, preferably from 10 to 30%, of the dry weight of (I) or (II) depending on the desired intensity of the fireproofing effect.
  • the said percentages relate to the total weight of (I) and (II).
  • Application may be for example by dipping, spraying or padding.
  • the agent is fixed thereon by heating for from about two to twenty minutes at about to 200 (1., preferably from to C. Following this, the fibrous material thus finished is given a conventional after-treatment for removal of unfixed agent; for example it may be washed with hot dilute aqueous alkali metal hydroxide solution or alkali metal carbonate solution.
  • agents (I) and (II) which, as already stated, may be used together, are compatible with all other agents for textile finishing, particularly with a great variety of aminoplast-forming monomeric, oligomeric and polymeric compounds and may be used together with them.
  • the method according to this invention may be carried out by all procedures and in all apparatus which would otherwise be used for finishing fibrous materials.
  • Cellulosic fibrous materials may include cotton, linen, sisal, hemp, regenerated cellulose and wood-wool in the form of filaments, threads, fibers, wadding, nonwoven fabrics or sheet materials, such as textiles and papers of all types. These materials may be mixed with others, fo example wool, silk, polyester, polyamide or polyacrylonitrile, the total fireproofing eifect then corresponding to that of the cellulose fraction.
  • Values for the fireproofing and resistance to washing of the finish are given in Table 1.
  • DIN is the abbreviation for Deutsche Industrie Norm, a German industrial standard.
  • DIN 53906 is equivalent to ASTM-D-1230.
  • DIN 54011 is equivalent to ISO-R105. The following abbreviations are used in the table:
  • the compound (1 is prepared like the compound (I according to Example 1.
  • T tear length in cm without washing 7
  • T tear length in cm after washing with water at 60 C.
  • the compound (IP) is prepared like the compound (1 as described in Example 1, substituting chloromethylphosphonyldichloride for phosphorus oxychloride.
  • the compound (I1 is prepared like the compound (I as described in Example 1, substituting chloromethylphosphonyldichloride for phosphorus oxychloride.
  • Fireproofed fibrous material consisting of or containing cellulose which has been finished with 10-30% by weight, with reference to the cellulose, of a mixture of compounds having one or both of the Formulae I and II:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Fireproofing Substances (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Paper (AREA)
US3503793D 1966-10-08 1967-10-05 Cellulosic fibrous materials Expired - Lifetime US3503793A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEB0089266 1966-10-08
DE19661594915 DE1594915A1 (de) 1966-10-08 1966-10-08 Verfahren zur Flammfestausruestung von Fasermaterial aus Cellulose

Publications (1)

Publication Number Publication Date
US3503793A true US3503793A (en) 1970-03-31

Family

ID=25753399

Family Applications (1)

Application Number Title Priority Date Filing Date
US3503793D Expired - Lifetime US3503793A (en) 1966-10-08 1967-10-05 Cellulosic fibrous materials

Country Status (9)

Country Link
US (1) US3503793A (de)
AT (1) AT268193B (de)
BE (1) BE704847A (de)
CH (1) CH481257A (de)
DE (1) DE1594915A1 (de)
FR (1) FR1540157A (de)
GB (1) GB1191877A (de)
NL (1) NL6713640A (de)
SE (1) SE323053B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932123A (en) * 1973-03-16 1976-01-13 The United States Of America As Represented By The Secretary Of Agriculture Flameproofing of cotton cellulose with hexamethyl phosphorous triamide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969440A (en) * 1974-09-23 1976-07-13 Scott Paper Company Phosphorus containing acrylic esters and amides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891877A (en) * 1956-06-05 1959-06-23 Leon H Chance Flame resistant organic textiles and method of production
GB892131A (en) * 1957-07-05 1962-03-21 Bayer Ag Flame-proofing process
US3205034A (en) * 1962-03-15 1965-09-07 Leon H Chance Process for treating cotton textiles with nu, nu'-ethylene bis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891877A (en) * 1956-06-05 1959-06-23 Leon H Chance Flame resistant organic textiles and method of production
GB892131A (en) * 1957-07-05 1962-03-21 Bayer Ag Flame-proofing process
US3205034A (en) * 1962-03-15 1965-09-07 Leon H Chance Process for treating cotton textiles with nu, nu'-ethylene bis

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932123A (en) * 1973-03-16 1976-01-13 The United States Of America As Represented By The Secretary Of Agriculture Flameproofing of cotton cellulose with hexamethyl phosphorous triamide

Also Published As

Publication number Publication date
AT268193B (de) 1969-02-10
GB1191877A (en) 1970-05-13
CH481257A (de) 1969-12-31
FR1540157A (fr) 1968-09-20
NL6713640A (de) 1968-04-09
BE704847A (de) 1968-04-09
SE323053B (de) 1970-04-27
CH1396867A4 (de) 1969-07-31
DE1594915A1 (de) 1969-08-28

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