US3503793A - Cellulosic fibrous materials - Google Patents
Cellulosic fibrous materials Download PDFInfo
- 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
- Authority
- 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
Links
- 239000002657 fibrous material Substances 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 description 29
- 239000004744 fabric Substances 0.000 description 12
- 238000004079 fireproofing Methods 0.000 description 12
- 238000005406 washing Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- FZXSSJIKXCFPDP-UHFFFAOYSA-N chloro(dichlorophosphoryl)methane Chemical compound ClCP(Cl)(Cl)=O FZXSSJIKXCFPDP-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- -1 phosphorus amides Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000198134 Agave sisalana Species 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical class NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- RSJXMPXQBLWCFT-UHFFFAOYSA-N chloromethyl-N,N-dimethylphosphonamidic acid Chemical compound CN(P(O)(=O)CCl)C RSJXMPXQBLWCFT-UHFFFAOYSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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)
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)
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)
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)
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 |
-
1966
- 1966-10-08 DE DE19661594915 patent/DE1594915A1/de active Pending
-
1967
- 1967-10-05 US US3503793D patent/US3503793A/en not_active Expired - Lifetime
- 1967-10-05 GB GB4545267A patent/GB1191877A/en not_active Expired
- 1967-10-05 SE SE1367667A patent/SE323053B/xx unknown
- 1967-10-06 CH CH1396867A patent/CH481257A/de not_active IP Right Cessation
- 1967-10-06 NL NL6713640A patent/NL6713640A/xx unknown
- 1967-10-06 AT AT909467A patent/AT268193B/de active
- 1967-10-09 FR FR123756A patent/FR1540157A/fr not_active Expired
- 1967-10-09 BE BE704847D patent/BE704847A/xx unknown
Patent Citations (3)
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)
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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