CA1091858A - Durable flame retardant finishes for textile materials - Google Patents
Durable flame retardant finishes for textile materialsInfo
- Publication number
- CA1091858A CA1091858A CA271,144A CA271144A CA1091858A CA 1091858 A CA1091858 A CA 1091858A CA 271144 A CA271144 A CA 271144A CA 1091858 A CA1091858 A CA 1091858A
- Authority
- CA
- Canada
- Prior art keywords
- percent
- flame retardant
- group
- finish
- hydroxymethyl
- 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
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 167
- 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 title claims abstract description 128
- 239000004753 textile Substances 0.000 title claims abstract description 47
- 239000000463 material Substances 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000004744 fabric Substances 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 61
- -1 phosphate ester Chemical class 0.000 claims abstract description 49
- 238000012360 testing method Methods 0.000 claims abstract description 42
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000001477 organic nitrogen group Chemical group 0.000 claims abstract description 22
- 238000009472 formulation Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 239000000080 wetting agent Substances 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical class OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- ZYNUSOWWGMTZHH-UHFFFAOYSA-L oxalate;tetrakis(hydroxymethyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO ZYNUSOWWGMTZHH-UHFFFAOYSA-L 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical class [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- WPWUKAWNHCZFGG-UHFFFAOYSA-J tetrakis(hydroxymethyl)phosphanium;acetate;phosphate Chemical compound CC([O-])=O.[O-]P([O-])([O-])=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO WPWUKAWNHCZFGG-UHFFFAOYSA-J 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 3
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 claims description 3
- XBWLQTCLJURGNV-UHFFFAOYSA-N CCOC(CCO)C(O)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O Chemical compound CCOC(CCO)C(O)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XBWLQTCLJURGNV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- BUMDTXZEIVUMMS-UHFFFAOYSA-N bis(2-hydroxyethyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate Chemical compound OCCOC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCCO BUMDTXZEIVUMMS-UHFFFAOYSA-N 0.000 claims description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- YBJYHROQFQYDGN-UHFFFAOYSA-N tetrakis(1-hydroxyethyl)phosphanium Chemical class CC(O)[P+](C(C)O)(C(C)O)C(C)O YBJYHROQFQYDGN-UHFFFAOYSA-N 0.000 claims description 2
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- ZRLLAMDEJSHNEB-UHFFFAOYSA-N 2,4-dihydroxybutyl 2,3,4,5-tetrabromo-6-ethylperoxycarbonylbenzoate Chemical compound CCOOC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCC(O)CCO ZRLLAMDEJSHNEB-UHFFFAOYSA-N 0.000 claims 1
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 claims 1
- AYFKRVFTDMUQDB-UHFFFAOYSA-N OCCCC(O)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O Chemical compound OCCCC(O)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O AYFKRVFTDMUQDB-UHFFFAOYSA-N 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 39
- 229920000742 Cotton Polymers 0.000 abstract description 36
- 150000002009 diols Chemical class 0.000 abstract description 5
- 229910019142 PO4 Inorganic materials 0.000 abstract description 4
- 239000010452 phosphate Substances 0.000 abstract description 4
- 230000000979 retarding effect Effects 0.000 abstract description 2
- 239000000839 emulsion Substances 0.000 description 25
- 239000000543 intermediate Substances 0.000 description 18
- 239000000470 constituent Substances 0.000 description 15
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
- 239000000835 fiber Substances 0.000 description 11
- 239000012141 concentrate Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229940060038 chlorine Drugs 0.000 description 6
- 235000017168 chlorine Nutrition 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000220010 Rhode Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013036 cure process Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229940091868 melamine Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- ZTBDCHNXDHUMCJ-UHFFFAOYSA-K tetrakis(hydroxymethyl)phosphanium;phosphate Chemical compound [O-]P([O-])([O-])=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO ZTBDCHNXDHUMCJ-UHFFFAOYSA-K 0.000 description 2
- MUIAJVMZXDIDQX-UHFFFAOYSA-N 2,3,4,5-tetrabromo-6-(3-hydroxypropoxycarbonyl)benzoic acid Chemical compound C(CO)COC(=O)C1=C(C(=C(C(=C1Br)Br)Br)Br)C(=O)O MUIAJVMZXDIDQX-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- GVRRBIORNFRJPX-UHFFFAOYSA-N 3,3-dibromopropyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCC(Br)Br GVRRBIORNFRJPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920002821 Modacrylic Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- NMDGMYNXRRCPGM-UHFFFAOYSA-N dibromo propyl phosphate Chemical compound P(=O)(OBr)(OBr)OCCC NMDGMYNXRRCPGM-UHFFFAOYSA-N 0.000 description 1
- HRUKYLHTIMFQKY-UHFFFAOYSA-N diphosphanium;oxalate Chemical compound [PH4+].[PH4+].[O-]C(=O)C([O-])=O HRUKYLHTIMFQKY-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- KLCLDJDZIDYFMQ-UHFFFAOYSA-N hydroxymethylphosphanium;oxalate Chemical compound OC[PH3+].OC[PH3+].[O-]C(=O)C([O-])=O KLCLDJDZIDYFMQ-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 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
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/236—Esters of carboxylic acids; Esters of carbonic acid containing halogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
- D06M13/21—Halogenated carboxylic acids; Anhydrides, halides or salts 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
- 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
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US660,502 | 1976-02-23 | ||
| US05/660,502 US4046701A (en) | 1976-02-23 | 1976-02-23 | Durable flame retardant finishes for textile materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1091858A true CA1091858A (en) | 1980-12-23 |
Family
ID=24649800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA271,144A Expired CA1091858A (en) | 1976-02-23 | 1977-02-07 | Durable flame retardant finishes for textile materials |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4046701A (enExample) |
| JP (1) | JPS52103599A (enExample) |
| CA (1) | CA1091858A (enExample) |
| DE (1) | DE2707497C3 (enExample) |
| FR (1) | FR2341689A1 (enExample) |
| GB (1) | GB1570316A (enExample) |
| IT (1) | IT1075656B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4015037A (en) * | 1976-03-22 | 1977-03-29 | Michigan Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4219605A (en) * | 1976-09-29 | 1980-08-26 | Ciba-Geigy Corporation | Process for flameproofing synthetic fibre material and product |
| US4444914A (en) * | 1981-09-11 | 1984-04-24 | Smith Derek A | Smoke and toxic gas suppressant system |
| JPS61266668A (ja) * | 1985-05-15 | 1986-11-26 | 日東紡績株式会社 | 防炎加工方法 |
| JPS61275477A (ja) * | 1985-05-27 | 1986-12-05 | 株式会社クラレ | 防炎加工法 |
| DE3674308D1 (de) * | 1985-08-06 | 1990-10-25 | Albright & Wilson | Biozide zusammensetzungund verfahren zur behandlung von wasser. |
| US5084542A (en) * | 1990-05-31 | 1992-01-28 | E. I. Du Pont De Nemours And Company | Epoxy/isocyanate crosslinked coatings containing 1,3-disubstituted imidazole-2-thione catalysts |
| US8557347B1 (en) | 2009-05-04 | 2013-10-15 | Matchmaster Dyeing & Finishing, Inc. | Flame retardant fabrics and methods for manufacturing the same |
| US9982096B2 (en) * | 2013-10-25 | 2018-05-29 | Milliken & Company | Flame retardant precursors, polymers prepared from such precursors, and flame resistant fabrics treated with such polymers |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE596967A (enExample) * | 1959-11-12 | |||
| US3310419A (en) * | 1963-04-16 | 1967-03-21 | Hooker Chemical Corp | Process for treating cellulosic material with flameproofing composition |
| CH485869A (de) * | 1968-01-22 | 1970-02-15 | Stoeckli Geb | Verfahren zur Rostverhütung in blechumschlossenen Hohlräumen von Karosserien |
| US3660582A (en) * | 1969-03-27 | 1972-05-02 | Michigan Chem Corp | Production of flame-retardant spun-formed material |
| US3729434A (en) * | 1971-06-28 | 1973-04-24 | Michigan Chem Corp | Method of producing fire retardant emulsions |
| BE791245A (fr) * | 1971-11-10 | 1973-05-10 | Hooker Chemical Corp | Procede pour ignifugation de matieres cellulosiques |
| BE788592A (fr) * | 1972-01-14 | 1973-03-08 | Ciba Geigy | Procede de preparation de produits de condensation phosphoriques, produits obtenus et emploi comme ignifuges |
| US3877974A (en) * | 1972-10-25 | 1975-04-15 | White Chemical Corp | Flame retardants for blends of natural and synthetic fibers |
| US3888779A (en) * | 1972-12-26 | 1975-06-10 | American Cyanamid Co | Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate |
| US3936585A (en) * | 1973-12-05 | 1976-02-03 | Robert Bruce Leblanc | Fire retarding textile materials |
| US3856535A (en) * | 1973-12-06 | 1974-12-24 | Ici America Inc | Emulsifiable haloalkyl phosphate blend for aqueous textile flame-retardant treatments |
-
1976
- 1976-02-23 US US05/660,502 patent/US4046701A/en not_active Expired - Lifetime
-
1977
- 1977-02-07 CA CA271,144A patent/CA1091858A/en not_active Expired
- 1977-02-21 IT IT20512/77A patent/IT1075656B/it active
- 1977-02-22 DE DE2707497A patent/DE2707497C3/de not_active Expired
- 1977-02-23 FR FR7705322A patent/FR2341689A1/fr active Granted
- 1977-02-23 JP JP1976877A patent/JPS52103599A/ja active Granted
- 1977-02-23 GB GB7606/77A patent/GB1570316A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1570316A (en) | 1980-06-25 |
| DE2707497C3 (de) | 1981-08-13 |
| IT1075656B (it) | 1985-04-22 |
| DE2707497A1 (de) | 1977-08-25 |
| JPS5719231B2 (enExample) | 1982-04-21 |
| US4046701A (en) | 1977-09-06 |
| FR2341689B1 (enExample) | 1978-11-03 |
| DE2707497B2 (de) | 1980-09-11 |
| FR2341689A1 (fr) | 1977-09-16 |
| JPS52103599A (en) | 1977-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |