US3817779A - Process for imparting flame retardancy to a textile - Google Patents
Process for imparting flame retardancy to a textile Download PDFInfo
- Publication number
- US3817779A US3817779A US00230951A US23095172A US3817779A US 3817779 A US3817779 A US 3817779A US 00230951 A US00230951 A US 00230951A US 23095172 A US23095172 A US 23095172A US 3817779 A US3817779 A US 3817779A
- Authority
- US
- United States
- Prior art keywords
- textile
- sample
- grams
- minutes
- flame
- 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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- 238000000034 method Methods 0.000 title description 34
- 239000004753 textile Substances 0.000 title description 29
- 239000003063 flame retardant Substances 0.000 abstract description 20
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 10
- 230000000979 retarding effect Effects 0.000 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- -1 normally flammable Substances 0.000 description 18
- 239000004744 fabric Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XXXPHVYZYDJIEO-UHFFFAOYSA-N di(propan-2-yloxy)phosphorylmethyl prop-2-enoate Chemical class CC(C)OP(=O)(OC(C)C)COC(=O)C=C XXXPHVYZYDJIEO-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000297 Rayon Polymers 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 239000002964 rayon Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910000410 antimony oxide Inorganic materials 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical group O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 239000012757 flame retardant agent Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- PEHQDSOLLVMPLB-UHFFFAOYSA-N OOP(O)=O Chemical compound OOP(O)=O PEHQDSOLLVMPLB-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- LIYKJALVRPGQTR-UHFFFAOYSA-M oxostibanylium;chloride Chemical compound [Cl-].[Sb+]=O LIYKJALVRPGQTR-UHFFFAOYSA-M 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 239000002759 woven fabric Substances 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
- D06M14/24—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of animal origin, e.g. wool or silk
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
- D06M14/04—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
- D06M14/06—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of animal origin, e.g. wool or silk
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
- D06M14/22—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
-
- 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
Definitions
- flame retarding agents and methods of application have been developed in attempts to obtain flame retardant textile materials.
- mixtures of ammonium dihydrogen orthophosphate or boric acid with borax have been used to retard flame in cellulosic materials.
- Flame retardant textiles have been produced by depositing metal oxides, within or on the fibers of cellulose, by the successive precipitation of ferric oxide and a mixture of tungstic acid and stannic oxide or by successive deposition of antimony trioxide and titanium dioxide.
- Such processes require plural treatment baths in which strongly acidic solutions are employed. These strongly acidic solutions are both inconvenient to use and pose the problem of possible degradation of the cellulose.
- a metal oxide coating on cellulosic textile materials, creates difiiculties in some subsequent dyeing processes as well as deleteriously affecting the hand of the finished product.
- One process which involves the use of a single processing bath consists of padding a dispersion of a chlorinated hydrocarbon and finely divided antimony oxide on a cellulosic fabric. The fabric is thereafter heated to render the finish wash proof. Near the combustion temperature, antimony oxide will react with hydrogen chloride, generated by degradation of the chlorinated hydrocarbon, to form antimony oxychloride which suppresses flame.
- the combination of a chlorinated hydrocarbon and finely divided antimony oxide are not acceptable finishes for closely woven fabrics because they deleteriously affect the hand of the finished product.
- Flame resistance has been imparted to cellulosic materials by esterification of the cellulose with diammonium hydrogen orthophosphate. Products so treated are subjected to metathesis reactions with cations in aqueous solutions during washing, the ammonia cation being displaced by calcium, sodium or magnesim.
- the flame resistant properties of the diammonium orthophosphate ester of the cellulosic materials are regenerated by reacting the wash product with an ammonium chloride solution.
- Another object is to provide a process for treating normally flammable cellulosic, proteinaceous or analogous man-made materials to render them flame retardant.
- a particular object is to devise a composition
- a composition comprising normally flammable cellulosic, proteinaceous or analogous man-made material and an effective flame retarding amount of the compound represented by the formula wherein R R and R are as above described.
- a process for imparting flame retardancy to textile materials by incorporating into or on the textile material a flame retardant amount of one or more novel dialkylphosphonoalkyl acrylates and methacrylates of the formula wherein R is lower alkyl of 1 to 4 carbon atoms, R is hydrogen and lower alkyl of 1 to 4 carbon atoms and R is hydrogen and lower alkyl of 1 to 4 carbon atoms.
- the compounds useful in this invention are prepared by conventional methods for producing dialkylphosphonoalkyl acrylates or methacrylates which generally comprise the steps of (1) adding a dialkylhydrogen phosphite to an aldehyde to form a crude dialkyl-l-hydroxyalkylphosphonate, followed by (2) reacting the latter intermediate with acrylyl or methacryl chloride in the presence of a hydrogen chloride acceptor such as pyridine or sodium carbonate.
- a hydrogen chloride acceptor such as pyridine or sodium carbonate.
- 3,030,347 describes a process, wherein paraformaldehyde, acetaldehyde or propionaldehyde are utilized to form a crude dialkyl (1) hydroxy phosphonate, followed by (2) reacting the latter intermediate with acrylyl or methacryl chloride.
- Ser. No. 215,192 of which the present application is a continuation-in-part describes a process for the preparation of diisopropylphosphonomethyl acrylates or methacrylates by reacting the diisopropyl phosphite with aqueous formaldehyde in the presence of a base and thereafter reacting the product of this step with an alkyl acrylate to prepare the diisopropylphosphonomethyl acrylate or methacrylate.
- the compounds of this invention may be applied to textile materials by conventional finishing techniques such as by thermal or radiation induced pad curing so as to incorporate into the textile a flame retardant amount thereof.
- the compounds of this invention have advantages over the flame retardant agents of the prior art in that they may be used on a variety of textile materials of different chemical compositions, and they may be applied by a variety of methods. They may be applied to materials in either the fiber or fabric form to give flame retarding materials with minimum detectable physical changes in the quality or hand of the textile material.
- Cellulosic textile materials may be made flame retardant by way of a variety of methods.
- the cellulose may be treated with aqueous NaOH solutions to produce an anionic cellulosic form which will add to the acrylate of this invention.
- the reaction is by the addition of the cellulose alkoxide to the unsaturated carbonyl compound of this invention by the following manner.
- samples of the material are immersed in a to about 30% by weight NaOH solution for about 1 to about 20 minutes and squeezed to a wet pick up of about 60 to about 80%, based upon the weight of cellulosic material, using a two role laboratory padder at about 60 lbs. per square in gauge pressure.
- the samples are then dried to about 200 to about 275 Fahrenheit, for about 1 to about 5 minutes in a circulating air oven.
- the samples are then immersed in an aqueous solution of the flame retardant compound of this invention (20 to 70% by weight) for about 1 to about 20 minutes and squeezed to about 60 to about wet weight pick-up, based upon the weight of textile.
- the materials are then cured in a circulating air oven at about to about 450 Fahrenheit or preferably from about 275 to about 375 Fahrenheit for about 1 to about 10 minutes to promote reaction. Thereafter the samples are washed in hot water to remove residual unreacted material and dried.
- the products may also be grafted to cellulose by way of a free radical source generated on the cellulose back bone by way of electron beam irradiation.
- a free radical source generated on the cellulose back bone by way of electron beam irradiation.
- Cellulose is known to form stable free radicals under the influence of this type of irradiation.
- the materials to be grafted are immersed in a solution of the dialkyl phosphonoalkyl acrylated methylacrylate and squeezed in a two role laboratory padder at about 60 pounds per square inch gauge pressure to a wet weight pickup of about 70 to about 120%. The materials are then passed under an electron beam to give an average dose of 1.66 megarads to induce grafting. The samples are thereafter boiled in water to remove any homopolymer of the acrylate or methacrylate which may have formed and dried.
- the finished textile product whether subjected to additional finishing treatments or not, exhibits good flame resistant properties with minimum detectable physical changes in the quality or hand of the textile material.
- the flame retardant agents of this invention may be applied to various textiles such as cellulosic materials, proteinaceous materials and blends of cellulosic or proteinaceous materials with polyethylene terephthalate and analogous man made fibers.
- cellulosic materials applicant intends to embrace cotton, rayon, paper, regenerated cellulose and cellulose derivatives which retain a cellulose backbone of at least one hydroxy substituent per repeat ing glucose unit.
- proteinaceous material applicant intends to embrace those textile materials comprising the functional groups of proteins such as the various animal wools, hairs and furs.
- fire retardant agents of the instant invention to analogous man made fibers such as blends of cotton and polyethylene terephthalate, in textile fabrics and fibers to provide a uniform, flame retardant finish.
- the finished samples for testing have a flame retardant add on of about 5 to about 40% by weight preferably from about 10 to about 25% by weight of substrate.
- EXAMPLE I A sample of 5 oz. per square yard, cotton sheeting, was lmmersed m a solution containing 25 grams of l-diethylphosphonoethylacrylate and 75 grams of methanol. The sample was padded to about 100% wet pick up, air dried for about 24 hours and thereafter tested by AATCC Method 34-1969 for charring. The treated fabric had a calculated char length of 5.5 inches.
- EXAMPLE II A sample of 5.0 ounces per square yard, cotton sheeting was immersed in a 15% aqueous sodium hydroxide solution for about minutes, padded to about 60% wet pick up then circulating air oven dried at about 250 Fahrenheit. The sample was then immersed for about 10 minutes in an aqueous solution of l-diethylphosphonoethyl acrylate containing about 40% by weight acrylate, padded to about 75% wet pick up and then cured in a circulating air oven, at about 320 Fahrenheit, for about five minutes. Thereafter, the sample was washed with hot water in a home type automatic washer and tumble dried. The treated sample, when tested by AATCC Method 34-1969 for charring was found to have a char length of 6.5 inches.
- EXAMPLE III A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a aqueous solution of sodium hydroxide for ten minutes, padded to about 60% wet pick up and thereafter dried in a circulating air oven at about 250 Fahrenheit. The sample was then immersed for ten minutes in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol, cured in a circulating air oven at about 325 Fahrenheit for about 3 minutes, washed with hot water and tumble dried. The sample was then tested by AATCC Method 34-1969 for charring and was found to have a char length of 4.8 inches.
- EXAMPLE IV A sample, of 3.5 ounces per square yard, of a 75/25 blend of cotton to polyethylene terephthalate fabric was immersed in a 15% aqueous sodium hydroxide solution for about 10 minutes, padded to about 60% wet pick up, then dried in a circulating air oven at about 250 Fahrenheit. The sample was then immersed in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol for about 10 minutes, and padded to about 75 wet pick up. The fabric was thereafter cured in a circulating air oven at about 325 Fahrenheit for about 3 minutes, washed with hot water and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 8.0 inches.
- EXAMPLE V A sample of wool bedford cord of approximately 8.0 ounces per square yard was immersed for ten minutes in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol. The fabric was then padded to about 100% wet pick up and thereafter cured in a circulating air oven at about 325 Fahrenheit for 3 minutes. The so-cured product was then hot water washed and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 0.7 inch. The fabric sample was then subjected to 5 hot Water Wash cycles in an automatic home type Washer and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 1.5 inches.
- EXAMPLE VI A sample of wool bedford cord of approximately 8.0 ounces per square yard was immersed for ten minutes in a solution containing 200 grams of l-di-isopropylphosphonoethyl acrylate and 200 grams of methanol, and thereafter treated in accordance with Example V. Testing under 6 AATCC Method 34-1969, after the first hot water wash and tumble dry indicated char length of 1.0 inches. AATCC Method 34-1969 testing after five automatic home type washing cycles and tumble drying indicated a char length of 2.6 inches.
- EXAMPLE VII A sample of rayon staple fiber was immersed in an aqueous solution containing 15 grams of sodium hydroxide per grams of solution for ten minutes and padded to about 60% wet weight pick up. The sample was then dried in a circulating air oven at 250 Fahrenheit for 3 minutes, and thereafter immersed in a methanolic solution containing 200 grams of di-isopropylphosphonomethyl acrylate per 400 grams of solution for about ten minutes. The treated fiber was then padded to remove excess solution and cured in a circulating air oven at about 325" Fahrenheit for three minutes, rinsed in hot water and tumble dried. The fiber was then twisted tightly and held in a bunsen burner flame. Upon removal, the material was self extinguishing. An untreated sample of the rayon staple fiber, twisted tightly and held in the same bunsen burner flame, was completely consumed thereby.
- EXAMPLE VIII A sample of rayon staple fiber was immersed in an aqueous solution containing 15 grams of sodium hydroxide per 100 grams of solution for ten minutes, thereafter padded to about 60% wet weight pick up and dried in a circulating air oven at about 250 Fahrenheit for about 3 minutes. The sample was then immersed in a methanolic solution containing 50 grams of l-di-isopropylphosphonoethyl acrylate per 100 grams of solution for about 10 minutes and thereafter treated in accordance with Example VII. After curing washing and drying the fiber was twisted tightly and held in a bunsen burner flame. Upon removal from the flame, the material was self extinguishing. A sample of untreated rayon staple fiber was twisted tightly and held in the bunsen burner flame, was completely consumed by the flame.
- EXAMPLE IX 1 A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a solution containing 60 grams of diisopropylphosphonomethyl acrylate per 100 grams of methanol for 10 minutes, then padded to about 70% wet pick up. The thus treated sheeting was then exposed to ionizingradiation to an irradiation level of 1.66 megarads. The sample was thereafter boiled for about 0.5 hours in water, then about 0.5 hours in hexane and thereafter tumble dried to about 22.5% weight add on. The sample was then tested by AATCC Method 34-1969 and found to have a char length of 6.5 inches.
- EXAMPLE X A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a solution containing 40 grams of di-isopropylphosphonomethyl acrylate, 60 grams of N- methylolacrylamide and 100 grams of methanol. The sample was padded to about 70% wet weight pick up and irradiated as in Example IX to a level of 1.66 megarads. The sample was then boiled for about 0.5 hours in water, about 0.5 hours in hexane and thereafter tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 5.5 hours.
- a process for imparting flame retardancy to a textile selected from the group consisting of cellulosic material, proteinaceous material and blends thereof with polyethylene terephthalate which comprises treating said textile with an aqueous alkali metal hydroxide solution, contacting the thus treated textile with a compound of the formula:
- the flame retardant compound is of the formula 9.
- the flame retardant compound is of the formula References Cited UNITED STATES PATENTS 2,867,597 1/1959 Costello et a] 117-136 X 2,934,554 4/1960 Lane 117-136 X 4/ 1960 OBrien et al 117-136 X MICHAEL SOFOCLEOUS, Primary Examiner T. G. DAVIS, Assistant Examiner US. Cl. X.R.
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Abstract
NORMALLU FLAMMABLE EXTILES ARE RENDERED FLAME RETARDANT BY THE INTIMATE ASSOCIATION THEREWITH OF A FLAME RETARDING AMOUNT OF A COMPOUND OF THE FORMULA
CH2=C(-R3)-COO-CH(-R2)-P(=O)(-O-R1)2
WHEREIN R1 IS LOWER ALKYL OF 1 TO 4 CARBON ATOMS, R2 IS HYDROGEN AND LOWER ALKYL OF 1 YO 4 CARBONS AND R3 IS HYDROGEN AND LOWER ALKYL OF 1 TO 4 CARRBON ATOMS.
CH2=C(-R3)-COO-CH(-R2)-P(=O)(-O-R1)2
WHEREIN R1 IS LOWER ALKYL OF 1 TO 4 CARBON ATOMS, R2 IS HYDROGEN AND LOWER ALKYL OF 1 YO 4 CARBONS AND R3 IS HYDROGEN AND LOWER ALKYL OF 1 TO 4 CARRBON ATOMS.
Description
United States Patent Ofice 3,817,779 Patented June 18, 1974 U.S. Cl. 1l7136 9 Claims ABSTRACT OF THE DISCLOSURE Normally flammable textiles are rendered flame retardant by the intimate association therewith of a flame retarding amount of a compound of the formula ll (R O)zi (l3HOCC=CH2 Ra Ra wherein R is lower alkyl of 1 to 4 carbon atoms, R is hydrogen and lower alkyl of 1 to 4 carbon atoms and R is hydrogen and lower alkyl of 1 to 4 carbon atoms.
This is a continuation-in-part of pending application Ser. No. 215,192, filed Jan. 3, 1972.
FIELD OF INVENTION This invention relates to improvements in rendering flame retardant, normally flammable, fabrics such as cellulosic materials, proteinaceous materials and analogous man-made materials by applying thereto a flame retarding amount of a compound of the formula H II (RrOhP 9H0 C ?=CH7 Ra Ra wherein R is lower alkyl of 1 to 4 carbon atoms, R is hydrogen and lower alkyl of 1 to 4 carbon atoms and R is hydrogen and lower alkyl of 1 to 4 carbon atoms.
BACKGROUND OF THE INVENTION Many flame retarding agents and methods of application have been developed in attempts to obtain flame retardant textile materials. For example, mixtures of ammonium dihydrogen orthophosphate or boric acid with borax have been used to retard flame in cellulosic materials. Flame retardant textiles have been produced by depositing metal oxides, within or on the fibers of cellulose, by the successive precipitation of ferric oxide and a mixture of tungstic acid and stannic oxide or by successive deposition of antimony trioxide and titanium dioxide. Such processes require plural treatment baths in which strongly acidic solutions are employed. These strongly acidic solutions are both inconvenient to use and pose the problem of possible degradation of the cellulose. Furthermore, the presence of a metal oxide coating, on cellulosic textile materials, creates difiiculties in some subsequent dyeing processes as well as deleteriously affecting the hand of the finished product. One process which involves the use of a single processing bath, consists of padding a dispersion of a chlorinated hydrocarbon and finely divided antimony oxide on a cellulosic fabric. The fabric is thereafter heated to render the finish wash proof. Near the combustion temperature, antimony oxide will react with hydrogen chloride, generated by degradation of the chlorinated hydrocarbon, to form antimony oxychloride which suppresses flame. The combination of a chlorinated hydrocarbon and finely divided antimony oxide are not acceptable finishes for closely woven fabrics because they deleteriously affect the hand of the finished product.
Flame resistance has been imparted to cellulosic materials by esterification of the cellulose with diammonium hydrogen orthophosphate. Products so treated are subjected to metathesis reactions with cations in aqueous solutions during washing, the ammonia cation being displaced by calcium, sodium or magnesim. The flame resistant properties of the diammonium orthophosphate ester of the cellulosic materials are regenerated by reacting the wash product with an ammonium chloride solution.
OBJECTS OF THE INVENTION It is, therefore, a principal object of this invention to provide flame retarding textile fabrics comprising normally flammable cellulosic, proteinaceous or analogous manmade materials.
Another object is to provide a process for treating normally flammable cellulosic, proteinaceous or analogous man-made materials to render them flame retardant.
A particular object is to devise a composition comprising normally flammable cellulosic, proteinaceous or analogous man-made material and an effective flame retarding amount of the compound represented by the formula wherein R R and R are as above described.
These and other objects of the present invention will be obvious from the following description.
DESCRIPTION OF THE INVENTION In accordance with this invention, a process is provided for imparting flame retardancy to textile materials by incorporating into or on the textile material a flame retardant amount of one or more novel dialkylphosphonoalkyl acrylates and methacrylates of the formula wherein R is lower alkyl of 1 to 4 carbon atoms, R is hydrogen and lower alkyl of 1 to 4 carbon atoms and R is hydrogen and lower alkyl of 1 to 4 carbon atoms. The compounds useful in this invention are prepared by conventional methods for producing dialkylphosphonoalkyl acrylates or methacrylates which generally comprise the steps of (1) adding a dialkylhydrogen phosphite to an aldehyde to form a crude dialkyl-l-hydroxyalkylphosphonate, followed by (2) reacting the latter intermediate with acrylyl or methacryl chloride in the presence of a hydrogen chloride acceptor such as pyridine or sodium carbonate. U.S. Pat. 3,030,347 describes a process, wherein paraformaldehyde, acetaldehyde or propionaldehyde are utilized to form a crude dialkyl (1) hydroxy phosphonate, followed by (2) reacting the latter intermediate with acrylyl or methacryl chloride. Ser. No. 215,192 of which the present application is a continuation-in-part, describes a process for the preparation of diisopropylphosphonomethyl acrylates or methacrylates by reacting the diisopropyl phosphite with aqueous formaldehyde in the presence of a base and thereafter reacting the product of this step with an alkyl acrylate to prepare the diisopropylphosphonomethyl acrylate or methacrylate.
3 Illustrative examples of compounds useful in the present invention include, but are not limited to, compounds such as:
Diethylphosphonomethyl acrylate CH3 2 O Dl-lsopropylphosphonomethyl acrylate CH CH;
Di-lsopropylphosphonomethyl methacrylate ll (CAHnO) :1I ?HO C-CH=CH3 l-dibutylphosphonoethyl acrylate (C4HnO)zP-CHO%)C=CH2 I hHs CHa l-dlbutylphosphonopropyl methacrylate (C:H50):P OHOCCH=CH:
I cz s l-dlethylphosphonopropyl acrylate The compounds of this invention may be applied to textile materials by conventional finishing techniques such as by thermal or radiation induced pad curing so as to incorporate into the textile a flame retardant amount thereof. The compounds of this invention have advantages over the flame retardant agents of the prior art in that they may be used on a variety of textile materials of different chemical compositions, and they may be applied by a variety of methods. They may be applied to materials in either the fiber or fabric form to give flame retarding materials with minimum detectable physical changes in the quality or hand of the textile material.
Cellulosic textile materials may be made flame retardant by way of a variety of methods. Typically, the cellulose may be treated with aqueous NaOH solutions to produce an anionic cellulosic form which will add to the acrylate of this invention. Theoretically, the reaction is by the addition of the cellulose alkoxide to the unsaturated carbonyl compound of this invention by the following manner.
Cell-OH NaOH cell-0 m H1O II II cal-0 m ongooonomoan H10 II if ceu-ocmnooonomoan Ra Ra Applicant however, does not wish to be bound by this theory, intending to protect the claimed invention in whatever form or by whatever mechanism it takes place.
Generally, when treating cellulosic materials with aqueous NaOH, samples of the material are immersed in a to about 30% by weight NaOH solution for about 1 to about 20 minutes and squeezed to a wet pick up of about 60 to about 80%, based upon the weight of cellulosic material, using a two role laboratory padder at about 60 lbs. per square in gauge pressure. The samples are then dried to about 200 to about 275 Fahrenheit, for about 1 to about 5 minutes in a circulating air oven. The samples are then immersed in an aqueous solution of the flame retardant compound of this invention (20 to 70% by weight) for about 1 to about 20 minutes and squeezed to about 60 to about wet weight pick-up, based upon the weight of textile. The materials are then cured in a circulating air oven at about to about 450 Fahrenheit or preferably from about 275 to about 375 Fahrenheit for about 1 to about 10 minutes to promote reaction. Thereafter the samples are washed in hot water to remove residual unreacted material and dried.
The products may also be grafted to cellulose by way of a free radical source generated on the cellulose back bone by way of electron beam irradiation. Cellulose is known to form stable free radicals under the influence of this type of irradiation.
The materials to be grafted are immersed in a solution of the dialkyl phosphonoalkyl acrylated methylacrylate and squeezed in a two role laboratory padder at about 60 pounds per square inch gauge pressure to a wet weight pickup of about 70 to about 120%. The materials are then passed under an electron beam to give an average dose of 1.66 megarads to induce grafting. The samples are thereafter boiled in water to remove any homopolymer of the acrylate or methacrylate which may have formed and dried. The finished textile product, whether subjected to additional finishing treatments or not, exhibits good flame resistant properties with minimum detectable physical changes in the quality or hand of the textile material.
The flame retardant agents of this invention may be applied to various textiles such as cellulosic materials, proteinaceous materials and blends of cellulosic or proteinaceous materials with polyethylene terephthalate and analogous man made fibers. By cellulosic materials, applicant intends to embrace cotton, rayon, paper, regenerated cellulose and cellulose derivatives which retain a cellulose backbone of at least one hydroxy substituent per repeat ing glucose unit. By proteinaceous material applicant intends to embrace those textile materials comprising the functional groups of proteins such as the various animal wools, hairs and furs. Of special interest is the applicability of fire retardant agents of the instant invention to analogous man made fibers such as blends of cotton and polyethylene terephthalate, in textile fabrics and fibers to provide a uniform, flame retardant finish.
The following examples are presented for purposes of illustration rather than a limitation of the scope of the invention. In each of the examples the process steps were preformed as follows, except where a specific method is otherwise indicated. Padding .was done on a standard two role laboratory padder at a gauge pressure sufiicient to obtain about 100% wet weight pick-up. Drying was done in a standard home type automatic circulating air tumble dryer. Flammability testing was done in accordance with (American Association of Textile Chemists and Colorists) Test Method 34-1969, the standard vertical char method. Therein 2% in. x 10 in. fabric test specimens are exposed to a controlled burner flame under controlled conditions for a period of 12.0 seconds and 3.0 seconds. The charred specimens are thereafter subjected to controlled tearing tests, using tabulated weights, and the average tear length is measured as representaing the char length of the flame retardant treated fabric.
The finished samples for testing have a flame retardant add on of about 5 to about 40% by weight preferably from about 10 to about 25% by weight of substrate.
In each of the examples the indication of a char distance for the textile indicates self-extinguishment at that point. For comparison purposes the corresponding nontreated textile would be completely consumed.
EXAMPLE I A sample of 5 oz. per square yard, cotton sheeting, was lmmersed m a solution containing 25 grams of l-diethylphosphonoethylacrylate and 75 grams of methanol. The sample was padded to about 100% wet pick up, air dried for about 24 hours and thereafter tested by AATCC Method 34-1969 for charring. The treated fabric had a calculated char length of 5.5 inches.
EXAMPLE II A sample of 5.0 ounces per square yard, cotton sheeting was immersed in a 15% aqueous sodium hydroxide solution for about minutes, padded to about 60% wet pick up then circulating air oven dried at about 250 Fahrenheit. The sample was then immersed for about 10 minutes in an aqueous solution of l-diethylphosphonoethyl acrylate containing about 40% by weight acrylate, padded to about 75% wet pick up and then cured in a circulating air oven, at about 320 Fahrenheit, for about five minutes. Thereafter, the sample was washed with hot water in a home type automatic washer and tumble dried. The treated sample, when tested by AATCC Method 34-1969 for charring was found to have a char length of 6.5 inches.
EXAMPLE III A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a aqueous solution of sodium hydroxide for ten minutes, padded to about 60% wet pick up and thereafter dried in a circulating air oven at about 250 Fahrenheit. The sample was then immersed for ten minutes in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol, cured in a circulating air oven at about 325 Fahrenheit for about 3 minutes, washed with hot water and tumble dried. The sample was then tested by AATCC Method 34-1969 for charring and was found to have a char length of 4.8 inches.
In a similar manner a sample of 5.0 ounces per square yard of cotton sheeting was treated with di-isopropylphosphonomethyl methacrylate. After curing, washing and drying, testing by AATCC Method 34-1969 indicated a char length of 6.7 inches.
EXAMPLE IV A sample, of 3.5 ounces per square yard, of a 75/25 blend of cotton to polyethylene terephthalate fabric was immersed in a 15% aqueous sodium hydroxide solution for about 10 minutes, padded to about 60% wet pick up, then dried in a circulating air oven at about 250 Fahrenheit. The sample was then immersed in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol for about 10 minutes, and padded to about 75 wet pick up. The fabric was thereafter cured in a circulating air oven at about 325 Fahrenheit for about 3 minutes, washed with hot water and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 8.0 inches.
EXAMPLE V A sample of wool bedford cord of approximately 8.0 ounces per square yard was immersed for ten minutes in a solution containing 200 grams of di-isopropylphosphonomethyl acrylate and 200 grams of methanol. The fabric was then padded to about 100% wet pick up and thereafter cured in a circulating air oven at about 325 Fahrenheit for 3 minutes. The so-cured product was then hot water washed and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 0.7 inch. The fabric sample was then subjected to 5 hot Water Wash cycles in an automatic home type Washer and tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 1.5 inches.
EXAMPLE VI A sample of wool bedford cord of approximately 8.0 ounces per square yard was immersed for ten minutes in a solution containing 200 grams of l-di-isopropylphosphonoethyl acrylate and 200 grams of methanol, and thereafter treated in accordance with Example V. Testing under 6 AATCC Method 34-1969, after the first hot water wash and tumble dry indicated char length of 1.0 inches. AATCC Method 34-1969 testing after five automatic home type washing cycles and tumble drying indicated a char length of 2.6 inches.
EXAMPLE VII A sample of rayon staple fiber was immersed in an aqueous solution containing 15 grams of sodium hydroxide per grams of solution for ten minutes and padded to about 60% wet weight pick up. The sample was then dried in a circulating air oven at 250 Fahrenheit for 3 minutes, and thereafter immersed in a methanolic solution containing 200 grams of di-isopropylphosphonomethyl acrylate per 400 grams of solution for about ten minutes. The treated fiber was then padded to remove excess solution and cured in a circulating air oven at about 325" Fahrenheit for three minutes, rinsed in hot water and tumble dried. The fiber was then twisted tightly and held in a bunsen burner flame. Upon removal, the material was self extinguishing. An untreated sample of the rayon staple fiber, twisted tightly and held in the same bunsen burner flame, was completely consumed thereby.
EXAMPLE VIII A sample of rayon staple fiber was immersed in an aqueous solution containing 15 grams of sodium hydroxide per 100 grams of solution for ten minutes, thereafter padded to about 60% wet weight pick up and dried in a circulating air oven at about 250 Fahrenheit for about 3 minutes. The sample was then immersed in a methanolic solution containing 50 grams of l-di-isopropylphosphonoethyl acrylate per 100 grams of solution for about 10 minutes and thereafter treated in accordance with Example VII. After curing washing and drying the fiber was twisted tightly and held in a bunsen burner flame. Upon removal from the flame, the material was self extinguishing. A sample of untreated rayon staple fiber was twisted tightly and held in the bunsen burner flame, was completely consumed by the flame.
EXAMPLE IX 1 A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a solution containing 60 grams of diisopropylphosphonomethyl acrylate per 100 grams of methanol for 10 minutes, then padded to about 70% wet pick up. The thus treated sheeting was then exposed to ionizingradiation to an irradiation level of 1.66 megarads. The sample was thereafter boiled for about 0.5 hours in water, then about 0.5 hours in hexane and thereafter tumble dried to about 22.5% weight add on. The sample was then tested by AATCC Method 34-1969 and found to have a char length of 6.5 inches.
EXAMPLE X A sample of 5.0 ounces per square yard of cotton sheeting was immersed in a solution containing 40 grams of di-isopropylphosphonomethyl acrylate, 60 grams of N- methylolacrylamide and 100 grams of methanol. The sample was padded to about 70% wet weight pick up and irradiated as in Example IX to a level of 1.66 megarads. The sample was then boiled for about 0.5 hours in water, about 0.5 hours in hexane and thereafter tumble dried. Testing by AATCC Method 34-1969 indicated a char length of 5.5 hours.
I claim:
1. A process for imparting flame retardancy to a textile selected from the group consisting of cellulosic material, proteinaceous material and blends thereof with polyethylene terephthalate which comprises treating said textile with an aqueous alkali metal hydroxide solution, contacting the thus treated textile with a compound of the formula:
u (R1O)2P?HOC(IJ=CH2 7 wherein R is lower alkyl of 1 to 4 carbon atoms, R is hydrogen and lower alkyl of 1 to 4 carbon atoms and R is hydrogen and lower alkyl of 1 to 4 carbon atoms, and thereafter drying and curing the thus treated textile.
2. The process of claim 1 in which the amount of flame retardant compound add on is from about 5 to about 40% by weight of textile material.
3. The process of claim 1 in which the amount of flame retardant compound is from about 10 to about 25 percent by weight of textile material.
4. The process of claim 1 in which said textile material is a blend of cotton and polyethylene terephthalate.
5. The process of claim 2 wherein the flame retardant compound is of the formula 7. The process of claim 2 wherein the flame retardant compound is of the formula (isoC H O)z1T?HOfiGH=CH;
OCH; 0
8. The process of claim 2 wherein the flame retardant compound is of the formula 9. The process of claim 2 wherein the flame retardant compound is of the formula References Cited UNITED STATES PATENTS 2,867,597 1/1959 Costello et a] 117-136 X 2,934,554 4/1960 Lane 117-136 X 4/ 1960 OBrien et al 117-136 X MICHAEL SOFOCLEOUS, Primary Examiner T. G. DAVIS, Assistant Examiner US. Cl. X.R.
?} j UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 ,s17,779 Dated June 18, 1974 Inv n 0 Peter Golborn It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
' Column 1, line 27, after filed Jan. 3, 1972 insert -now U. S.
. Patent 3,780,146. Column 3, line 19, that portion of the formula reading CH 3 H3 cuo should read cuo 2 cu CH3 Column 3, line .7 4, "two role" should read --two ro1l--. Column 4,
line 6, "120/" should read "120%"; line 20,- "role" should read --roll--; line 51, "preformed" should read --performed--; line 52, "role" should read --roll--; line 63, "representaing" should read representing- Signed and sealed this 8th day of October 1974.
(SEAL) Attest:
MCCOY M. GIBSON JR. C. MARSHALL DANN Attestlng Officer Commissioner of Patents
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00215192A US3780146A (en) | 1972-01-03 | 1972-01-03 | Process for preparing di-isopropyl-phosphonomethyl acrylates or methacrylates |
US00230951A US3817779A (en) | 1972-01-03 | 1972-03-01 | Process for imparting flame retardancy to a textile |
CA160,436A CA992977A (en) | 1972-01-03 | 1973-01-03 | Process for preparing di-isopropylphosphonomethyl acrylates or methacrylates |
CA164,623A CA1005953A (en) | 1972-01-03 | 1973-02-15 | Dialkylphosphonoalkyl acrylates and methacrylate flame retardant textile finishes |
BE128117A BE795978A (en) | 1972-01-03 | 1973-02-26 | DIALCOYL-PHOSPHONDALCOYL ACRYLATES AND METHACRYLATES AS IGNIG-REPELLENT FINISHING AGENTS FOR TEXTILES |
NL7302660A NL7302660A (en) | 1972-01-03 | 1973-02-26 | |
DE19732309734 DE2309734A1 (en) | 1972-01-03 | 1973-02-27 | DIALKYLPHOSPHONOALKYL ACRYLATES AND THEIR USE FOR THE FLAME RETAINING EQUIPMENT OF TEXTILES |
JP48024212A JPS4898197A (en) | 1972-01-03 | 1973-02-28 | |
IT2099373A IT979583B (en) | 1972-03-01 | 1973-02-28 | FINISHES OF FIRE-PROOF TEXTILES BASED ON DIALKYL PHOSPHONALKYL ACRYLATES AND METHACRYLATES |
FR7307262A FR2174209B1 (en) | 1972-01-03 | 1973-03-01 | |
CH300973A CH571099B5 (en) | 1972-01-03 | 1973-03-01 | |
CH300973D CH300973A4 (en) | 1972-01-03 | 1973-03-01 | |
GB993973A GB1423610A (en) | 1972-01-03 | 1973-03-01 | Process for rendering textiles and textile materials flame retardant |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21519272A | 1972-01-03 | 1972-01-03 | |
US00230951A US3817779A (en) | 1972-01-03 | 1972-03-01 | Process for imparting flame retardancy to a textile |
Publications (1)
Publication Number | Publication Date |
---|---|
US3817779A true US3817779A (en) | 1974-06-18 |
Family
ID=26909800
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00215192A Expired - Lifetime US3780146A (en) | 1972-01-03 | 1972-01-03 | Process for preparing di-isopropyl-phosphonomethyl acrylates or methacrylates |
US00230951A Expired - Lifetime US3817779A (en) | 1972-01-03 | 1972-03-01 | Process for imparting flame retardancy to a textile |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00215192A Expired - Lifetime US3780146A (en) | 1972-01-03 | 1972-01-03 | Process for preparing di-isopropyl-phosphonomethyl acrylates or methacrylates |
Country Status (9)
Country | Link |
---|---|
US (2) | US3780146A (en) |
JP (1) | JPS4898197A (en) |
BE (1) | BE795978A (en) |
CA (2) | CA992977A (en) |
CH (2) | CH571099B5 (en) |
DE (1) | DE2309734A1 (en) |
FR (1) | FR2174209B1 (en) |
GB (1) | GB1423610A (en) |
NL (1) | NL7302660A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3906136A (en) * | 1971-04-30 | 1975-09-16 | Stauffer Chemical Co | Process of flame retarding substrates by applying hexahydratriazine phosphonate derivatives |
US4072776A (en) * | 1974-10-19 | 1978-02-07 | Hoechst Aktiengesellschaft | Process for the flameproofing of textile materials |
US4127698A (en) * | 1976-07-07 | 1978-11-28 | Kohjin Co., Ltd. | Composite fiber |
EP0527078A1 (en) * | 1991-08-05 | 1993-02-10 | Centre Technique Industriel dit: INSTITUT TEXTILE DE FRANCE | Process for fireproofing of textile materials |
CN107858832A (en) * | 2017-12-08 | 2018-03-30 | 天津工业大学 | A kind of method of the flame-retardant modified fabric of LBL self-assembly |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2815633B1 (en) * | 2000-10-24 | 2004-01-09 | Atofina | PROCESS FOR THE PREPARATION OF (DIALKYLPHOSPHONO) ALKYL (METH) ACRYLATE |
CA2887169C (en) | 2012-10-17 | 2022-01-04 | Icl-Ip America Inc. | Method of making hydroxymethylphosphonate, polyurethane foam-forming compositions, polyurethane foam and articles made therefrom |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2934555A (en) * | 1957-12-12 | 1960-04-26 | Rohm & Haas | Dialkylphosphonoalkyl acrylates and methacrylates and process for preparing same |
-
1972
- 1972-01-03 US US00215192A patent/US3780146A/en not_active Expired - Lifetime
- 1972-03-01 US US00230951A patent/US3817779A/en not_active Expired - Lifetime
-
1973
- 1973-01-03 CA CA160,436A patent/CA992977A/en not_active Expired
- 1973-02-15 CA CA164,623A patent/CA1005953A/en not_active Expired
- 1973-02-26 NL NL7302660A patent/NL7302660A/xx unknown
- 1973-02-26 BE BE128117A patent/BE795978A/en unknown
- 1973-02-27 DE DE19732309734 patent/DE2309734A1/en active Pending
- 1973-02-28 JP JP48024212A patent/JPS4898197A/ja active Pending
- 1973-03-01 FR FR7307262A patent/FR2174209B1/fr not_active Expired
- 1973-03-01 GB GB993973A patent/GB1423610A/en not_active Expired
- 1973-03-01 CH CH300973A patent/CH571099B5/xx not_active IP Right Cessation
- 1973-03-01 CH CH300973D patent/CH300973A4/xx unknown
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3906136A (en) * | 1971-04-30 | 1975-09-16 | Stauffer Chemical Co | Process of flame retarding substrates by applying hexahydratriazine phosphonate derivatives |
US4072776A (en) * | 1974-10-19 | 1978-02-07 | Hoechst Aktiengesellschaft | Process for the flameproofing of textile materials |
US4127698A (en) * | 1976-07-07 | 1978-11-28 | Kohjin Co., Ltd. | Composite fiber |
EP0527078A1 (en) * | 1991-08-05 | 1993-02-10 | Centre Technique Industriel dit: INSTITUT TEXTILE DE FRANCE | Process for fireproofing of textile materials |
FR2680184A1 (en) * | 1991-08-05 | 1993-02-12 | Inst Textile De France | METHOD FOR IGNIFUGATING TEXTILE MATERIALS |
US5281239A (en) * | 1991-08-05 | 1994-01-25 | Centre Technique Industriel Dit: Institut Textile De France | Process for imparting flame retardancy to textile materials |
CN107858832A (en) * | 2017-12-08 | 2018-03-30 | 天津工业大学 | A kind of method of the flame-retardant modified fabric of LBL self-assembly |
Also Published As
Publication number | Publication date |
---|---|
NL7302660A (en) | 1973-09-04 |
DE2309734A1 (en) | 1973-09-06 |
CA992977A (en) | 1976-07-13 |
GB1423610A (en) | 1976-02-04 |
CH571099B5 (en) | 1975-12-31 |
JPS4898197A (en) | 1973-12-13 |
CH300973A4 (en) | 1975-05-15 |
BE795978A (en) | 1973-08-27 |
FR2174209A1 (en) | 1973-10-12 |
FR2174209B1 (en) | 1976-11-05 |
CA1005953A (en) | 1977-03-01 |
US3780146A (en) | 1973-12-18 |
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Owner name: OCCIDENTAL CHEMICAL CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:HOOKER CHEMICALS & PLASTICS CORP.;REEL/FRAME:004109/0487 Effective date: 19820330 |