WO2007032277A1 - リン化合物およびその用途ならびに難燃性ポリエステル繊維 - Google Patents
リン化合物およびその用途ならびに難燃性ポリエステル繊維 Download PDFInfo
- Publication number
- WO2007032277A1 WO2007032277A1 PCT/JP2006/317873 JP2006317873W WO2007032277A1 WO 2007032277 A1 WO2007032277 A1 WO 2007032277A1 JP 2006317873 W JP2006317873 W JP 2006317873W WO 2007032277 A1 WO2007032277 A1 WO 2007032277A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- flame retardant
- phosphorus compound
- polyester fiber
- phosphorus
- flame
- Prior art date
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- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 162
- 239000011574 phosphorus Substances 0.000 title claims abstract description 159
- -1 Phosphorus compound Chemical class 0.000 title claims abstract description 139
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- 239000003063 flame retardant Substances 0.000 title claims description 194
- 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 description 189
- 229920000728 polyester Polymers 0.000 title claims description 146
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 59
- 239000003795 chemical substances by application Substances 0.000 claims description 40
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- 239000002131 composite material Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 238000003786 synthesis reaction Methods 0.000 description 29
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- IKQGVIGWBCHXDI-UHFFFAOYSA-N 6-benzylbenzo[c][2,1]benzoxaphosphinine Chemical compound O1C2=CC=CC=C2C2=CC=CC=C2P1CC1=CC=CC=C1 IKQGVIGWBCHXDI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- APOXBWCRUPJDAC-UHFFFAOYSA-N bis(2,6-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(C)=C1OP(O)(=O)OC1=C(C)C=CC=C1C APOXBWCRUPJDAC-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical class OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000009974 package dyeing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- SITVSCPRJNYAGV-UHFFFAOYSA-L tellurite Chemical compound [O-][Te]([O-])=O SITVSCPRJNYAGV-UHFFFAOYSA-L 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000009976 warp beam dyeing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- 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
-
- 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
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/30—Flame or heat resistance, fire retardancy properties
Definitions
- the present invention relates to a phosphorus compound having both an aromatic substituent and a phosphorinane skeleton, its use, and a flame retardant polyester fiber. More specifically, the present invention relates to the above-mentioned phosphorus compound, a flame retardant that also has the phosphorus compound strength, a flame retardant processing agent including the flame retardant, a flame retardant processing method using the flame retardant calorific agent, And flame retardant polyester fiber obtained thereby.
- polyester fibers are used in various fields such as excellent mechanical properties, easy processability, clothing, interiors, cotton padding, non-woven fabrics, and industrial materials. More specifically, polyester fibers are used as interior materials in, for example, hotels, hospitals, movie theaters, and the like. However, polyester fibers are flammable, and in these applications, strict regulations are set by the Fire Services Act to minimize the damage caused by fires such as matches and tobacco. Yes. In recent years, with the growing awareness of disaster prevention, the development of flame retardant polyester fiber is desired in order to create a safe and comfortable living environment.
- halogen compounds typified by hexose mouth mocyclododecane (HBCD) are mainly used. Recently, however, these compounds are being regulated as non-degradable and highly accumulative substances, and toxic halogenated hydrogen is generated when the flame-retardant processed product burns. Development of highly functional flame retardants is desired. In addition, the halogen compounds described above may develop into environmental problems with an extremely high risk of being mixed and leaked into the waste liquid of flame retardant processing. Therefore, as a flame retardant for polyester fibers, phosphorus compounds containing no halogen element have been actively researched. [0004] Linyi compounds are generally used in various fields as multifunctional compounds, and many varieties have been developed.
- the flame retardants are subject to a wide variety of resins, for example, polycarbonate resins, ABS resins, PPE®, polyester resins such as polyethylene terephthalate and polybutylene terephthalate, or thermoplastics such as polyester fibers.
- resins for example, polycarbonate resins, ABS resins, PPE®, polyester resins such as polyethylene terephthalate and polybutylene terephthalate, or thermoplastics such as polyester fibers.
- thermosetting resins such as resin and mixed resins, polyurethane resin, epoxy resin and phenol resin.
- the flame retardancy of coconut resin depends on the phosphorus content in the phosphorus compound blended as a flame retardant, and generally the higher the phosphorus content, the better the flame retardancy.
- this general theory does not necessarily apply when flame retardant polyester fibers.
- the polyester fiber has a high phosphorus content and a high polyester content from the viewpoint of imparting sufficient flame retardancy to the fiber and reducing the amount of flame retardant used.
- Phosphorus compounds are desired because they have a high amount of adsorption on the fiber and do not easily fall off.
- Patent Document 1 JP-A-2002-275473 discloses a phosphorus compound having a dibenzoxaphospholine oxide skeleton. This phosphorus compound has a relatively high flame retardancy as a V-phosphorus compound containing no halogen, and has high adhesion to polyester fibers.
- this Linyi compound is a persistent substance that is becoming the subject of regulation.
- the dye tends to be prevented from fixing to the fiber, and the fiber after the flame retardant dyeing treatment is inferior in light resistance.
- JP-A-2000-328445 Patent Document 2
- JP-A-2003-27373 Patent Document 3
- RD P resorcinol bis (diphenyl phosphate)
- this RDP is a liquid, it has low friction fastness and is inferior in hydrolysis resistance as a characteristic of the compound itself. Therefore, a dispersion containing RDP as a flame retardant is storage stable. However, the fiber after the flame-retardant dyeing treatment is inferior in durability and inferior in dyeability.
- JP-A-8-41781 Patent Document 4
- JP-A-2001-254268 Patent Document 5
- resorcinol bis (di-2,6-xylylphosphate) product name: PX-200, manufactured by Daihachi Chemical Industry Co., Ltd.
- This phosphorus compound exhibits excellent flame retardant performance against resin.
- Patent Document 1 Japanese Patent Application Laid-Open No. 2002-275473
- Patent Document 2 Japanese Patent Laid-Open No. 2000-328445
- Patent Document 3 JP 2003-27373 A
- Patent Document 4 JP-A-8-41781
- Patent Document 5 Japanese Patent Laid-Open No. 2001-254268
- the present invention does not contain halogen such as chlorine and bromine, has stable decomposition resistance to water and heat (hydrolysis resistance and heat resistance), and is used as a flame retardant processing agent. Excellent storage stability In addition, high flame retardancy can be imparted without degrading the physical properties of the fiber, and it has high sticking and exhausting properties to fibers, especially polyester fibers, and the dyes stick to the fibers. It is an object of the present invention to provide a phosphor composite having excellent light resistance, durability and high frictional fastness of the fiber after flame retardant dyeing treatment without impeding it.
- the present invention also relates to a flame retardant comprising the above-mentioned phosphorus compound, a flame retardant processing agent containing the flame retardant, a flame retardant processing method using the flame retardant, and a flame retardant polyester fiber obtained thereby. It is an issue to provide.
- the functional group having high adhesion to fibers is generally a molecular skeleton similar to a dye, and an aromatic ring is particularly preferable.
- a phosphorus compound having a general aromatic ring such as a phenyl group has insufficient adhesion to polyester fibers, and
- a phosphorus compound having both a specific aromatic substituent and a phosphorinane skeleton has a dramatic improvement in the fixing property to a polyester fiber.
- R 1 and R 2 are the same or different from each other, and a C atom optionally substituted with a hydrogen atom, a linear or branched C alkyl group, or a C alkyl group.
- R 5 , R 6 and R 7 are the same or different from each other and are a hydrogen atom or a C aryl group optionally substituted with an alkyl group, or R 3 and R 4 , R
- R 4 and R 5 , R 5 and R 6 or R 6 and R 7 may form a 6-membered ring together with the carbon atom of the benzene ring to which they are bonded, provided that R 4 , R 5 , R 6 and R 7 are not hydrogen atoms at the same time).
- a flame retardant for a polyester fiber comprising a flame retardant characterized by having the above-mentioned phosphorus compound strength and a flame retardant composed of the above-mentioned phosphorus compound.
- An agent is provided.
- the polyester fiber is treated with a flame retardant caloric agent for polyester fiber containing a flame retardant composed of the above-described phosphorus compound, thereby imparting flame retardancy to the polyester fiber.
- a flame-retardant processing method characterized by the above, and a flame-retardant polyester fiber obtained by fixing the above-mentioned phosphorus composite to a polyester fiber.
- the "phosphorus compound having both an aromatic substituent and a phosphorinan skeleton" refers to a six-membered ring force oxygen atom called a phosphorinan skeleton containing one phosphorus atom and two oxygen atoms.
- a phosphate compound bonded to an aromatic substituent refers to a six-membered ring force oxygen atom called a phosphorinan skeleton containing one phosphorus atom and two oxygen atoms.
- the flame retardant when containing a halogen such as chlorine or bromine, having stable flame resistance (hydrolysis resistance and heat resistance) against water and heat, the flame retardant is used. It has excellent storage stability, can impart high flame retardancy without lowering the physical properties of the fiber, and has high adhesion and exhaustibility to fibers, particularly polyester fibers. Does not prevent the dye from adhering to the fiber, and the fiber after flame retardant dyeing has excellent light resistance, durability and high V, Linyi compound having friction fastness can be provided.
- a halogen such as chlorine or bromine
- a flame retardant comprising the above-mentioned phosphorus compound, a flame retardant caloric agent containing the flame retardant, a flame retardant processing method using the flame retardant, and a difficulty obtained thereby.
- a flammable polyester fiber can be provided.
- the phosphorus composite of the present invention can impart excellent flame retardancy not only to polyester fibers but also to general rosin.
- the phosphorus compound of the present invention is represented by the formula (I).
- R 1 and R 2 in the formula (I) are the same or different from each other and may be substituted with a hydrogen atom, a linear or branched C alkyl group, or a C alkyl group.
- the "linear or branched C alkyl group" for R 1 and R 2 includes methyl, ethyl,
- linear alkyl groups such as n-hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neo-pentyl, isohexyl
- Examples include branched alkyl groups such as xylyl.
- Examples of the “group” include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
- the 1-4 alkyl group includes straight-chain alkyl groups such as methyl, ethyl, n-propyl, and n-butyl, and branched-chain alkyl groups such as isopropyl, isobutyl, sec-butyl, and tert-butyl.
- a kill group is mentioned.
- R 1 and R 2 are easily obtained as raw materials, and are easy to synthesize as described later. Therefore, linear or branched C alkyl groups are preferred methyl groups.
- R 3 , R 4 , R 5 , R 6 and R 7 in formula (I) are the same or different from each other;
- R 3 and R 4 , R 4 and R 5 , R 5 and R 6 or R 6 and R 7 may form a 6-membered ring together with the carbon atom of the benzene ring to which they are bonded, provided that R 5 , R 6 and R 7 are hydrogen sources at the same time Not a child.
- R 4 , R 5 , R 6 and R 7 are easily available as raw materials, and when using a phosphorus compound as a flame retardant for fibers, the exhaust properties to fibers are improved.
- the phosphorus compound of the present invention is particularly preferably a compound represented by the formula (II) or the formula (III) among the forces represented by the formula (I).
- R 1 and R 2 have the same meaning as above, R 5 , R 6 and R 7 are the same or different from each other and may be substituted with a hydrogen atom or a C alkyl group.
- Linyi compounds represented by the formula (II) include the following Linyi compounds 1-6.
- Examples of the phosphorus compound represented by the formula (III) include the following phosphorus compounds 7 to LO.
- the Linyi compound of the present invention can be produced by appropriately combining known Linyi compound synthesis processes. For example, a process of obtaining a di-substituted phosphorohalidate by reacting phosphorus trihalide with a diol (step (I)), and the resulting di-substituted phosphorono, the substituted may be substituted.
- the phosphorus compound of the present invention can be produced by reacting phenols or naphthols in the presence of a hydrogen halide scavenger and, if necessary, a catalyst (step (II)).
- phosphorus trihalogenated phosphorus and optionally substituted phenols or naphthols are reacted in the presence of a catalyst, if necessary, followed by diols and dehalogenation.
- a catalyst if necessary, followed by diols and dehalogenation.
- Examples of phosphorus trihalides in the step (I) include phosphorus oxychloride and phosphorus oxybromide. In view of availability and cost, phosphorus oxychloride is particularly preferable.
- Examples of the diols in the step (I) include 1,3 propanediol, 2,2 dimethyl-1,3 propanediol (neopentyl glycol), 2,2 jetyl-1,3 propandiol, 2-methyl-2-propyl 1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-phenyl-1,3-propanediol, and the like.
- 1,3 propanediol, neopentyl glycol, 2 butyl-2-ethyl-1,3 propanediol are preferred because of their easy availability and cost.
- Cyldaricol, 2-butyl-2-ethyl 1,3 propanediol is particularly preferred!
- a solvent that does not participate in the reaction may be used.
- a compound that is solid at room temperature such as neopentyl alcohol, can proceed smoothly by dissolving or dispersing in a solvent.
- solvents examples include benzene, toluene, xylene, black benzene, dichloromethane benzene, 1,4 dioxane, tetrahydrofuran, 1,2 dichloroethane, and the like.
- step (I) In the reaction of step (I), if necessary, 1 mol of oxytrihalogenous phosphorus is added to 1 mol of a diol containing a solvent and reacted, and then generated using a hydrogen halide absorber or the like.
- a general method is to remove halogenated hydrogen from the system. The method is described in, for example, JP-A-2-273688.
- the reaction temperature in step (I) is 40 to 80 ° C, preferably 45 to 75 ° C.
- the reaction time is preferably as short as possible as long as it is appropriately determined according to conditions such as the reaction volume and the capacity of the hydrogen halide absorber to be used.
- step (I) for example, as shown in the following formula, phosphorus oxytrichloride and 1 mol of glycols (HO CH CR'R'CH —OH with respect to 1 mol of oxytrichloride) )
- step (V) phenols or naphthols may be substituted with the disubstituted phosphorono and redate obtained in step (I) in the presence of a halogenated hydrogen scavenger and, if necessary, a catalyst. Reaction is carried out to obtain the phosphorus compound of the present invention.
- Examples of the optionally substituted phenols in the step (II) include 2-phenol phenol, 3-phenyl phenol, 4-phenyl phenol, 2,6-diphenyl phenol, and the like. But there are 1 naphthols as naphthols! /, 2 naphthols. Among these, in terms of availability and cost, and when a phosphorus compound is used as a flame retardant for fibers, the exhaust properties to polyester fibers are improved. In terms of further enhancing the 2-phenol-phenol,
- Examples of the halogen-hydrogen scavenger in the step (II) include triethylamine, tributylamine, pyridine and the like.
- the amount of hydrogen halide scavenger used is preferably 1 to 1.5 monoreca per 1 mole of phenols or naphthols, and more preferably from 1.02 to L2 monoreca! / ⁇ .
- Examples of the catalyst in the step (II) include Lewis acid catalysts such as magnesium chloride and aluminum chloride salt and amine catalysts such as 4 (dimethylamino) pyridine.
- the amount of catalyst used is preferably 0.001 to 0.1 mole per mole of di-substituted phosphorohalidate, more preferably 0.002 to 0.05 monoreca! / ⁇ .
- a solvent that does not participate in the reaction may be used.
- a compound that is solid at room temperature such as neopentylene phosphorochloridate, can be smoothly reacted by dissolving or dispersing in a solvent.
- solvents examples include benzene, toluene, xylene, black benzene, dichloro benzene, 1,4 dioxane, tetrahydrofuran, 1,2 dichloroethane, and the like.
- the reaction temperature in step (II) is -10 to 100 ° C, preferably 60 to 90 ° C.
- the interval is 0.1 to 10 hours, preferably 0.5 to 5 hours.
- step (II) for example, as shown in the following formula, 1 mol of phenols or 1 mol of phenol substituted with 1 mol of the disubstituted phosphorono or lydate obtained in step (I) may be substituted.
- naphthols for example, as shown in the following formula, 1 mol of phenols or 1 mol of phenol substituted with 1 mol of the disubstituted phosphorono or lydate obtained in step (I) may be substituted.
- the phosphorus compound of the present invention is obtained by reacting in the presence of a hydrogen halide scavenger (represented by B in the formula) and, if necessary, a catalyst.
- a hydrogen halide scavenger represented by B in the formula
- R 1 and R 2 have the same meaning as described above, and R 8 represents a phenyl group having a substituent to R 7 in formula (I)).
- phosphorus compound 1 can be produced by the above steps (I) and (II) as shown in the following formula.
- the flame retardant of the present invention is characterized in that it is a phosphor compound of the present invention.
- the phosphorus compound of the present invention can impart excellent flame retardancy to the target material without affecting the physical properties of the target material having a high phosphorus content. Because it does not contain any rogen, it is also easy to recycle because there is no environmental pollution during combustion or disposal. Are better.
- the flame retardant of the present invention is useful as a flame retardant for various materials, particularly for resins.
- the flame retardant of the present invention is useful for both synthetic resins and natural resins, but is particularly useful for synthetic resins.
- polyester resins such as polyethylene terephthalate and polybutylene terephthalate, polycarbonate resins, ABS resins, PPE resins and thermoplastic resins such as mixed resins thereof, and unsaturated polyester resins.
- thermosetting resins such as polyurethane resins, epoxy resins, and phenol resins.
- the flame retardant of the present invention is particularly useful for polyester resins such as polyethylene terephthalate and polybutylene terephthalate.
- the form of rosin is not particularly limited,
- the amount of the flame retardant used in the present invention may be appropriately set depending on the type and form of the material to be flame retardant, the required degree of flame retardancy, and the like.
- the amount of the flame retardant of the present invention used is 0.1% by weight or more, preferably 0.5% by weight or more, more preferably 1% by weight or more, and 30% by weight or less, preferably with respect to the resin. Is less than 20% by weight.
- the amount of the phosphorus compound used is less than 0.1% by weight, it may not be possible to impart sufficient flame retardancy to the resin, which is not preferable.
- the amount of the phosphorus compound used exceeds 30% by weight, it is not preferable because it may adversely affect various physical properties of the resin, particularly mechanical properties.
- the flame retardant processing agent for polyester fiber of the present invention is characterized by containing the flame retardant which also has the combined strength of the present invention.
- the flame retardant processing agent for polyester fibers will be described.
- the present invention is not limited to this, and the phosphorus compound of the present invention is also useful for general resin.
- the phosphorus composite of the present invention has a specific aromatic substituent as a functional group having a specific fixing performance to polyester fibers, among polyester fibers, polyester is particularly preferred. Useful for tellurite.
- polyester fibers include known fibers such as polyethylene terephthalate, polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polytrimethylene naphthalate, polybutylene naphthalate, isophthalic acid-modified polyethylene terephthalate, isophthalic acid.
- known fibers such as polyethylene terephthalate, polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polytrimethylene naphthalate, polybutylene naphthalate, isophthalic acid-modified polyethylene terephthalate, isophthalic acid.
- modified polybutylene terephthalate and among these, polyethylene terephthalate is particularly preferable.
- polyester fiber In the form of polyester fiber, it can be applied to misalignment such as regular polyester fiber and cationic dyeable polyester fiber.
- the flame retardant of the present invention is also useful for composite fibers (blends and unwoven fabrics) of polyester fibers and other fibers.
- polyester fibers examples include synthetic fibers such as nylon, acrylic and polyurethane, semi-synthetic fibers such as acetate, regenerated fibers such as rayon, and natural fibers such as cotton, hemp, silk and wool.
- the flame retardant of the present invention is also useful for fibers made of a single material other than polyester fibers.
- the form of the fiber is not particularly limited, and examples thereof include woven fabrics, knitted fabrics, non-woven fabrics, strings, ropes, yarns, tows, tops, caskets, and knitted fabrics.
- the cross-sectional shape of the fiber is not particularly limited, and may be either round or other irregular shape.
- the thickness of the fiber is not particularly limited, but in the case of polyester fiber, for example, 0.001-3 OOOD (denier: grams per 9000 m in length) is preferable. 0.01 to 200 D force S is particularly preferable.
- the use of the fiber is not particularly limited, and examples thereof include interior use, automobile use, clothing use, industrial use, and fishing net use.
- the amount of the flame retardant of the present invention may be appropriately set depending on the type and form of the material to be flame retardant, the required degree of flame retardancy, and the like.
- the amount of the flame retardant used is 0. It is 1% by weight or more, preferably 0.5% by weight or more, more preferably 1% by weight or more, and 30% by weight or less, preferably 20% by weight or less.
- the amount of the phosphorus compound used is less than 0.1% by weight, it is not preferable because sufficient flame retardancy may not be imparted to the polyester fiber.
- the amount of phosphorus compound used exceeds 30% by weight, the fiber surface tends to bleed out, the texture tends to deteriorate, and the dyeability decreases when dyeing simultaneously with flame-retardant processing.
- Examples of the flame retardant processing agent of the present invention include an aqueous solution obtained by emulsifying the phosphorus compound of the present invention with an emulsifier, and an aqueous solution obtained by dispersing the phosphorus compound of the present invention with a dispersant (dispersion stabilizer). And a solution prepared by dissolving the phosphoric compound of the present invention in an organic solvent.
- the flame retardant processing agent of the present invention may contain a dye or an additive known in the art as long as it does not inhibit the effects of the present invention.
- the phosphorus compound of the present invention is 5 to 80% by weight, preferably 10 to 70% by weight, in the flame retardant coating material of the present invention.
- milky agent known ones can be used, for example, a product with a higher alcohol alkylene oxide, a product with an alkylphenol alkylene oxide, a product with a styrenated alkylphenol alkylene oxide.
- Polyalkylene glycol type such as products with polypropylene glycol ethylene oxide; fatty acid ester of glycerol, fatty acid ester of pentaerythritol, fatty acid ester of sorbitol and sorbitan Le, fatty acid esters of sucrose, alkyl ethers of polyhydric alcohols, polyhydric alcohol type of which nonionic surfactants such as fatty acid amides of alkanol ⁇ Min acids;
- Carboxylate such as fatty acid soap, higher alcohol sulfate, higher alkyl polyalkylene glycol ether sulfate, sulfated oil, sulfated fatty acid ester Sulfates such as tellurium, sulfated fatty acids and sulfated olefins; formalin condensates such as alkylbenzene sulfonates, alkylnaphthalene sulfonates and naphthalene sulfonates, a-olefin sulfonates and paraffin sulfonates Sulfonates such as Igepon T-type (a compound obtained by the reaction of oleic acid chloride and N-methyltaurine), sulfosuccinic acid diester salt;
- surfactants include phosphoric acid ester salts such as higher alcohol phosphoric acid ester salts.
- the amount of the emulsifier is 0.05 to 15 parts by weight, preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the flame retardant.
- the blending amount of the emulsifier is less than 0.05 parts by weight, it is not preferable because aggregation and sedimentation of the phosphorus compound cannot be sufficiently suppressed.
- the blending amount of the emulsifier exceeds 15 parts by weight, the viscosity of the dispersion increases, and the applicability of the flame retardant finish to the fiber tends to decrease, such being undesirable.
- dispersing agent known ones can be used, and examples thereof include polybutyl alcohol, methyl cellulose, hydroxymethyl cellulose, xanthan gum, starch paste and the like.
- the blending amount of the dispersant is 0.05 to 15 parts by weight, preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the flame retardant.
- the amount of the dispersant is less than 0.05 parts by weight, it is not preferable because aggregation and sedimentation of the phosphorus compound cannot be sufficiently suppressed.
- the blending amount of the dispersant exceeds 15 parts by weight, the viscosity of the dispersion increases, and the impartability of the flame retardant finish to the fiber tends to decrease.
- organic solvent examples include aromatic hydrocarbons such as toluene, xylene, and alkylnaphthalene; alcohols such as methanol, ethanol, isopropanol, and ethylene glycol; ketones such as acetone and methyl ethyl ketone; And ethers such as ethylcellosolve; amides such as dimethylformamide; sulfoxides such as dimethyl sulfoxide; halogenated hydrocarbons such as methylene chloride and black mouth form. These can be used alone or as a mixture of two or more.
- aromatic hydrocarbons such as toluene, xylene, and alkylnaphthalene
- alcohols such as methanol, ethanol, isopropanol, and ethylene glycol
- ketones such as acetone and methyl ethyl ketone
- ethers such as ethylcellosolve
- amides such as dimethylformamide
- the flame retardant processing agent is an aqueous emulsion or dispersion
- a known apparatus used for the production of an emulsion type or dispersion type flame retardant for example, a homogenizer, a colloid mill, etc.
- a flame retardant finish can be prepared using an emulsifier or a disperser such as a ball mill or a sand grinder.
- Known additives include, for example, UV absorbers, antistatic agents, water and oil repellents, antifouling agents, hard finishes, texture adjusting agents, softeners, antibacterial agents, water absorbing agents, and antislip agents. , Carrier and so on.
- ultraviolet absorber examples include benzotriazole series and benzophenone series.
- the carrier will be explained in Method 3 of the flame retardant processing method.
- the flame retardant processing method of the present invention is to treat a polyester fiber with a flame retardant caloric agent for polyester fiber containing a flame retardant that also has the above-mentioned phosphorus compound strength to impart flame retardancy to the polyester fiber.
- a specific flame-retardant processing method will be described below. In the following, the ability to explain the flame retardant method of polyester fiber is not limited to this.
- Linyi compound of the present invention is also useful for general fats and oils.
- the flame retardant processing method of the present invention is a method for obtaining a flame retardant processed fiber (a flame retardant processed product), and the polyester fiber is contacted with the flame retardant processing agent including the flame retardant of the present invention that also has a phosphorus compound power.
- the phosphorus composite is fixed to the polyester fiber (fixing step), and the polyester fiber is heated to perform post-processing (heat treatment step).
- the force or part of the phosphorus composite of the present invention attached to the surface of the polyester fiber is taken into the molecular skeleton of the polyester fiber and fixed.
- the molecular skeleton of the polyester fiber relaxes or swells, and the phosphorus compound incorporated therein diffuses and settles in the molecular skeleton.
- the phosphorus compound of the present invention has a structure having a specific aromatic substituent, the amount of fixing easily in the molecular skeleton of the polyester fiber is large, and the fixing is strong.
- a low molecular weight substance derived from a flame retardant may scatter and emit smoke during heat treatment at ° C.
- fuming does not adversely affect the working environment.
- the following methods 1 to 3 are particularly preferable.
- Method 1 is a method in which the polyester fiber that has been brought into contact with the flame retardant curing agent is heated to a temperature of 100 to 220 ° C.
- a dry heat or wet heat method such as can be applied.
- the polyester fiber is spray-treated or pad-treated (fixing step) with a flame retardant coating agent or a diluted solution thereof, and dried. Thereafter, heat treatment is performed at normal temperature at a temperature of 100 to 220 ° C, preferably 160 to 200 ° C, more preferably 180 to 200 ° C for several tens of seconds to several minutes (heat treatment step).
- the treatment temperature at this time is too low, the molecular skeleton of the polyester fiber becomes difficult to relax or expand to the extent that it can accept the molecules of the phosphorus compound present in the flame retardant construction agent. This is not preferable because it is difficult to impart sufficient flame retardancy to the polyester fiber.
- the treatment temperature is too high, the phosphoric compound can be more firmly fixed to the polyester fiber, but the fiber strength of the polyester fiber itself is decreased or the heat is reduced although there are differences depending on the heating conditions. This is not preferred because there is a risk of denaturation.
- the phosphorous compound force present in the flame retardant finish is stably and more firmly fixed to the amorphous region in the polyester fiber molecule even at normal pressure. Therefore, according to Method 1, sufficient flame retardancy and washing durability can be imparted to the polyester fiber.
- Method 2 is a method in which the polyester fiber is immersed in a flame retardant processing agent or a diluted solution thereof and heat-treated at high temperature and normal pressure or high pressure (for example, 90 to 150 ° C, normal pressure to 0.4 MPa). is there. That is, this is a method in which the fixing process and the heat treatment process are performed simultaneously.
- the polyester fiber is immersed in a flame retardant and the temperature is 90 to 150 ° C, normal pressure. Immersion heat treatment is performed for several minutes to several tens of minutes under high temperature normal pressure or high temperature pressurization of ⁇ 0.4 MPa, preferably at a temperature of 110 to 140 ° C. and high pressure of 0.05 to 0.3 MPa.
- the treatment temperature at this time is too low, it becomes difficult for the molecular skeleton of the polyester fiber to relax or expand to the extent that it can accept the molecules of the phosphorus compound present in the flame retardant construction agent. This is not preferable because it is difficult to impart sufficient flame retardancy to the polyester fiber.
- the treatment temperature is too high, the phosphoric compound can be more firmly fixed to the polyester fiber, but the fiber strength of the polyester fiber itself is decreased or the heat is reduced although there are differences depending on the heating conditions. This is not preferred because there is a risk of denaturation.
- the phosphorous compound present in the flame retardant finish is stably and non-crystallized in the non-crystalline region in the polyester fiber molecule, as in Method 1. Many stick. Therefore, according to the method 2, sufficient flame retardancy and washing durability can be imparted to the polyester fiber.
- the flame retardant processing agent or a diluted solution thereof may be preheated to the above suitable temperature range.
- Method 3 involves immersing the polyester fiber in a flame retardant finishing agent further comprising a carrier in the flame retardant treatment agent of Method 2 or a diluted solution thereof, and then, for example, at a temperature of 80 to 130 ° C., normal pressure to 0.2 MPa.
- the carrier means a substance that swells the polyester fiber and promotes good fixation of the phosphorus compound in the molecular arrangement of the polyester fiber.
- carrier a known carrier used in carrier dyeing can be used. Examples thereof include chlorobenzene-based, aromatic ester-based, methylnaphthalene-based, difurle-based, benzoic acid-based, and ortho-furfurol-based compounds. These compounds can be used alone or as a mixture of two or more.
- the compounding amount of the carrier is 0.1 to 10% o.w.f. (on the weight of fiber), preferably 1.0 to 5.0% o.w.f. based on the weight of the polyester fiber to be processed.
- the polyester fiber is flame retardant. This is not preferable because it is difficult to impart.
- the carrier is not preferable because it is difficult to emulsify or disperse the carrier in the flame retardant processing agent or its diluted solution.
- the carrier emulsified or dispersed in the flame retardant finish is adsorbed to the polyester fiber, thereby promoting the fixation of the phosphorus compound in the molecular arrangement of the polyester fiber.
- phosphorus compound (I) there is a sufficient amount of phosphorus compound (I) to exhibit flame retardancy even when heat treatment is performed under milder conditions, for example, at a temperature of 80 to 130 ° C. and normal pressure to 0.2 MPa. ! ⁇ can stably fix the phosphorus compound (II) inside the polyester fiber.
- the contact step and the heat treatment step may be performed simultaneously, and before the polyester fiber is dipped in the flame retardant agent containing the carrier or its diluted solution, The flame retardant finishing agent or a diluted solution thereof may be heated in advance to the above suitable temperature range.
- the timing of fixing the phosphorus compound existing in the flame retardant coating agent to the polyester fiber is before dyeing the polyester fiber, simultaneously with the dyeing or after dyeing.
- the viewpoint power to increase the work efficiency by reducing the number of steps and the number of working steps is particularly preferable at the same time as the dyeing.
- the polyester fiber is subjected to a sorbing treatment by a known method to remove the phosphorus compound that does not firmly adhere to the polyester fiber but adheres gently to the surface. I like it!
- the polyester fiber does not require a high degree of washing durability, it is not necessary that the phosphorus compound present in the flame retardant calorie is firmly fixed to the surface of the polyester fiber.
- the phosphorus compound may only adhere loosely to the fiber surface. In this case, the heat treatment step can be substantially omitted.
- flame retardancy can be imparted to the polyester fiber even when the phosphorus compound adheres loosely to the surface of the polyester fiber!
- each performance may be imparted by individual treatment, but a known additive may be added to the extent that the effects of the present invention are not impaired.
- a polyester fiber may be treated by the above-described methods 1 to 3 using a flame retardant containing flame retardant, and a plurality of performances may be simultaneously imparted to the polyester fiber.
- a back coating method using acrylic resin or polymer latex is a method of imparting flame retardancy to polyester fibers by applying a back coating agent of an acrylic resin-containing polymer latex containing the phosphorus compound of the present invention to the polyester fiber surface.
- the flame retardant processing method described above is a post-treatment for fixing the phosphorus composite of the present invention to the fiber.
- the fiber is a synthetic fiber! It is also possible to obtain a flame retardant fiber by spinning a molten polymer containing a compound.
- the temperature and speed in spinning are not particularly limited, and may be set as appropriate by applying to conventional spinning conditions.
- the fiber when the fiber is a polyester fiber, 0.05 weight 0/0 even without the low content of phosphorus atoms in the fiber (P), preferably 0.1 to 3.0 mass 0/0, More preferably, the phosphorus compound is blended so as to be 0.2 to 2.0% by mass.
- the flame retardancy tends to be insufficient, which is not preferable.
- the phosphorus atom content exceeds 3.0% by mass, the flame retardancy is saturated, and various properties inherent to the polyester fiber are likely to deteriorate.
- the flame-retardant polyester fiber of the present invention is formed by fixing the phosphorus compound represented by the formula (I) of the present invention to a polyester fiber.
- the flame-retardant polyester fiber of the present invention contains a flame retardant comprising the phosphorus compound of the present invention. It is obtained by treating polyester fiber with a flame retardant cachet for polyester fiber. Flame retardant polyester fiber of the present invention, the amount fixation of phosphorus compounds of formula (I), is preferably in the range of 0.1 to 30 weight 0/0 flame retardant poly ester fiber! /,.
- a 1 liter four-necked flask equipped with a stirrer, thermometer, dropping device, hydrochloric acid recovery device and reflux tube was charged with 104. Og (l mol) of neopentyl glycol and 114.4 g of black-ended benzene.
- the obtained mixed solution was heated to 45 to 55 ° C. with stirring, and 153.5 g (l mol) of phosphorus oxychloride was added dropwise to the mixed solution over 1 hour. After completion of the addition, the mixed solution was heated to 75 ° C. over 1 hour and reacted at the same temperature (75 ° C.) for 1 hour to recover 65.7 g of hydrogen chloride generated.
- the resulting reaction mixture was cooled to room temperature and to this was added 16-5.5 g (0.95 mol) of 2-phenol-phenol (ortho-phenol), 0.9 g of magnesium chloride and 145.6 g of black mouth benzene. .
- the mixed solution was heated to 65 to 75 ° C. with stirring, and 106.lg (l. 05 mol) of triethylamine was added dropwise to the mixed solution over 1 hour. Then, the mixture was reacted at the same temperature (75 ° C) for 1 hour to obtain a mixed solution of 5,5 dimethyl-2- (2'-phenolphenoxy) 1,3,2 dioxaphosphorinane 2-oxide. .
- an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added, neutralized at 85 ° C., and allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C. and dehydrated.
- the obtained oil phase was gradually cooled to crystallize 259.8 g of white needle crystals.
- the purity of the obtained crystal by GPC was 99.0 area%. Crystal The crude yield was 86.0% when all of these were assumed to be the target compounds.
- the structure of the obtained crystal was determined from the results of quantitative analysis of phosphorus by elemental analysis and absorption spectroscopy using a UV spectrometer, NMR, 13 C-NMR, and FT-IR. It was confirmed that it was 5,5 dimethyl-2- (2, -phenol-phenoxy) -1,3,2 dioxafosolinan 2-oxide (Linley compound 1).
- the melting point of the crystal was measured with a trace melting point measuring device (manufactured by YANAKO INSTITUTE DEVELOPMENT LABORATORY, model: MP-J3).
- Neopentyl glycol 104 Use 2 butyl 2 ethyl 1,3 propanediol 160. Og (l mol) instead of Og (1 mol) and do not use the black benzene added to the reaction mixture! In the same manner as in Synthesis Example 1, a mixed solution was obtained.
- an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added, neutralized at 85 ° C., and allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C and dehydrated, and then the solvent was removed at 100 ° C and 2.7 kPa.
- the resulting liquid was 312.6 g of a pale yellow liquid.
- the purity of the obtained liquid by GPC was 96.6 area%.
- the crude yield was 88.0% when all the crystals were assumed to be the target compound.
- the structure of the obtained liquid was determined from the results of quantitative analysis of phosphorus by elemental analysis and absorption spectroscopy using a UV spectrometer, NMR, 13 C-NMR, and FT-IR. It was confirmed that it was 5-butyl-5-ethyl-2- (2, -phenol-phenoxy) 1, 3, 2 dioxaphosphorinane-2-oxide (phosphorus compound 4).
- the obtained mixed solution was cooled to room temperature, and an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added thereto for neutralization treatment, and then allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C. and drained with a centrifugal filter.
- the obtained solid was dried with a vacuum dryer at 100 ° C. to obtain 253.7 g of a white solid.
- the purity of the obtained solid by GPC was 98.7 area%. Also, assuming that all of the solid is the target compound
- the crude yield was 84.0%.
- an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added, neutralized at 85 ° C., and allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C. and drained with a centrifugal filter.
- the obtained solid was dried with a vacuum dryer at 90 ° C. to obtain 248.7 g of a white solid.
- the purity of the obtained solid by GPC was 98.5 area%.
- the crude yield was 70.0% when all the solids were assumed to be the target compound.
- the structure of the obtained solid was determined from the results of quantitative analysis of phosphorus by elemental analysis and absorption spectrometry using a UV spectrometer, NMR, 13 C-NMR, and FT-IR. It was confirmed that it was 5-butyl-5-ethyl-2- (4, -phenol-phenoxy) 1, 3, 2 dioxaphosphorinane-2-oxide (phosphorus compound 6).
- an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added, neutralized at 85 ° C., and allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C. and drained with a centrifugal filter.
- the obtained solid was dried with a vacuum dryer at 100 ° C. to obtain 227.5 g of a white solid.
- the purity of the obtained solid by GPC was 99.0 area%.
- the crude yield was 82.0% when all of the solid was assumed to be the target compound.
- the structure of the obtained solid was determined from the results of quantitative analysis of phosphorus by elemental analysis and absorption spectroscopy using a UV spectrometer, NMR, 13 C-NMR, and FT-IR. It was confirmed that it was 5,5-dimethyl-2- (2′-naphthyloxy) 1,3,2 dioxaphosphorinane-2-oxide (phosphorus compound 7) of the formula.
- an aqueous hydrochloric acid solution corresponding to an excess amount of triethylamine was added, neutralized at 85 ° C., and allowed to stand to extract an oil phase.
- the obtained oil phase was washed with water at about 85 ° C. and drained with a centrifugal filter.
- the resulting solid is vacuum dried at 100 ° C. Drying in a kettle gave a white solid 210. Og.
- the purity of the obtained solid by GPC was 99.2 area%.
- the crude yield was 86.8% assuming that all of the solid was the target compound.
- Phosphorus compound 3 (See Synthesis Example 3)
- Phosphorus compound 6 (See Synthesis Example 4)
- Phosphorus compound 7 (See Synthesis Example 5)
- Comparative phosphorus compound 2 10-benzyl-9, 10-dihydro-9-oxa 10-phosphaphenanthrene 1 10-oxide
- Polyethylene terephthalate 100% polyester fiber fabric (weight per unit 250gZm 2 )
- a flame retardant finish for flame retardant processing of a polyester fiber fabric was prepared.
- Linyi compound 4 10 g was mixed with 1.5 g of product name: Disper N-700 manufactured by Meisei Chemical Co., Ltd. as a dispersion stabilizer. Next, about 20 g of water was added to the obtained mixture in several drops, and the process was repeated until a paste was obtained. While stirring the paste with a high-speed stirrer, about 80 g of water was added little by little to obtain a flame retardant 2 in the form of a white dispersion.
- a white-dispersed liquid flame retardant 3 was obtained in the same manner as the preparation of flame retardant 1 except that the phosphorus compound 3 was used instead of the phosphorus compound 1.
- a white dispersion liquid flame retardant 4 was obtained in the same manner as the preparation of flame retardant 1 except that the phosphorus compound 6 was used instead of the phosphorus compound 1.
- a white dispersion liquid flame retardant 6 was obtained in the same manner as the preparation of flame retardant 1 except that comparative phosphorus 1 was used in place of the phosphorus composite 1.
- a white dispersed liquid flame retardant 7 was obtained in the same manner as the preparation of flame retardant 1 except that the comparative phosphorus 2 was used instead of the phosphorus 1.
- a white dispersion liquid flame retardant 8 was obtained in the same manner as the preparation of flame retardant 1 except that the comparative phosphorus 3 was used instead of the phosphorus compound 1.
- a white dispersion liquid flame retardant 9 was obtained in the same manner as in the preparation of flame retardant 2 except that the comparative phosphorus 4 was used instead of the phosphorus 2.
- Polyester fiber fabrics were flame retardant processed using the prepared flame retardant finishing agents 1-5 (Examples 1-5) and flame retardant finishing agents 6-9 (Comparative Examples 1-4).
- Disperse dye (Mitsubishi Kasei Kogyo Co., Ltd., trade name: Dianix Blue AC-E)
- a flame retardant was added so that the concentration of the phosphorus compound was 8% o.w.f.
- a dye bath containing a flame retardant and a polyester fiber fabric with a bath ratio of 1:30 were set in a mini-color tester (manufactured by Tecsum Giken), and the polyester fiber fabric was treated at 130 ° C for 60 minutes. The treated polyester fiber fabric was reduced and washed at 70 ° C for 20 minutes, washed with hot water, and dried. The polyester fiber fabric was then heat treated at 150 ° C for 3 minutes.
- the flame retardant polyester fiber fabric was evaluated by the following method. However, flame retardant 6
- Each test piece after processing of polyester fiber fabric is decomposed by heating with sulfuric acid, nitric acid and perchloric acid, diluted with distilled water, and then a certain amount of nitric acid, ammonium vanadate solution and ammonium molybdate solution are added. Add color and then use a spectrophotometer Absorbance was measured.
- a polyester fiber woven fabric that has been processed with flame retardancy was visually evaluated. Judgment was made based on good, slightly good, slightly poor, and poor according to the dyeability. Table 1 shows the results obtained.
- “Dyeability” evaluates whether a dye (dye) is applied to a fabric (fiber) with the expected color.
- the finished polyester fiber fabric that was flame-retardant was evaluated according to the dyeing fastness test method using an ultraviolet carbon arc lamp stipulated in JIS L 0842.
- the exposure time was 20 hours, and a standard 4th grade judgment was made. Result obtained Are shown in Table 1.
- the polyester fiber woven fabric processed with flame retardancy was evaluated according to the dyeing fastness test method for friction specified in JIS L 0849. Both dry and wet tests were performed with a friction tester type II. The test results show that the fastness to friction is the highest in grade 5, and the lowest in grade 1. The results obtained are shown in Table 1.
- the polyester fiber fabric of Example 1 5 has far superior flame retardancy in comparison with the polyester fiber fabric of Comparative Example 1 4 in any state before washing, after washing and after dry cleaning. It shows that the physical properties of the fiber such as dyeability and texture are also good.
- Comparative Example 1 The polyester fiber fabric of 4 has low flame retardancy (Comparative Examples 1 and 4), has poor dyeability, has poor light fastness, and discolors the fiber. It may not be able to demonstrate its specific performance (Comparative Example 2) or contain low molecular weight phosphorus compounds. It can be seen that smoke is emitted during treatment (Comparative Examples 3 and 4).
- the phosphorus composite of the present invention can impart flame retardancy to polyester fibers without deteriorating various physical properties such as dyeability and texture.
- the flame retardant processing method for polyester fibers which uses a flame retardant processing agent for polyester fibers containing the phosphorus compound of the present invention as a flame retardant, to fix the phosphorus compound to the fibers, imparts flame retardancy simultaneously with dyeing. It can be seen that the processing can be performed. It can be seen that all the performances are excellent because the strength and the fastness are also good without reducing the physical properties of the fibers such as dyeability and texture.
- the phosphorus compound of the present invention is a non-halogen compound and can eliminate the harmful effects of halogen compounds.
- the power of the polyester fiber according to the present invention is useful for general resin.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Claims
Priority Applications (5)
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JP2007535447A JP4909901B2 (ja) | 2005-09-14 | 2006-09-08 | リン化合物およびその用途ならびに難燃性ポリエステル繊維 |
EP06783233.7A EP1925622B1 (en) | 2005-09-14 | 2006-09-08 | Phosphorus compound, use thereof and flame-retardant polyester fiber |
KR1020087003394A KR101286484B1 (ko) | 2005-09-14 | 2006-09-08 | 인 화합물, 그의 용도 및 난연성 폴리에스테르 섬유 |
CN2006800314248A CN101253184B (zh) | 2005-09-14 | 2006-09-08 | 磷化合物及其用途和阻燃聚酯纤维 |
US11/994,597 US8835541B2 (en) | 2005-09-14 | 2006-09-08 | Phosphorus compounds, use thereof and flame retarding polyester fibers |
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JP2005266765 | 2005-09-14 | ||
JP2005-266765 | 2005-09-14 |
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WO2007032277A1 true WO2007032277A1 (ja) | 2007-03-22 |
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PCT/JP2006/317873 WO2007032277A1 (ja) | 2005-09-14 | 2006-09-08 | リン化合物およびその用途ならびに難燃性ポリエステル繊維 |
Country Status (7)
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US (1) | US8835541B2 (ja) |
EP (1) | EP1925622B1 (ja) |
JP (1) | JP4909901B2 (ja) |
KR (1) | KR101286484B1 (ja) |
CN (1) | CN101253184B (ja) |
TW (1) | TWI385176B (ja) |
WO (1) | WO2007032277A1 (ja) |
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JP2010121067A (ja) * | 2008-11-20 | 2010-06-03 | Matsumoto Yushi Seiyaku Co Ltd | 非水系難燃性付与剤組成物および非水系難燃性樹脂組成物 |
WO2011142136A1 (ja) | 2010-05-14 | 2011-11-17 | 大八化学工業株式会社 | リン酸エステルの製造方法 |
JP2012517502A (ja) * | 2009-02-09 | 2012-08-02 | アイシーエル−アイピー アメリカ インコーポレイテッド | 難燃剤を含有するポリウレタンフォーム組成物、およびこの難燃剤を含有するポリウレタンフォーム組成物を製造するためのプロセス、難燃剤組成物およびこれらから製造されるポリウレタンフォーム |
JP2012167411A (ja) * | 2011-02-16 | 2012-09-06 | Daikyo Kagaku Kk | ポリエステル系繊維品の難燃加工剤と難燃加工方法 |
JP2013011049A (ja) * | 2011-05-30 | 2013-01-17 | Toray Ind Inc | 複合強化繊維束、その製造方法、および成形材料 |
JP2013011050A (ja) * | 2011-05-30 | 2013-01-17 | Toray Ind Inc | 複合強化繊維束、その製造方法、および成形材料 |
WO2013147294A1 (ja) * | 2012-03-29 | 2013-10-03 | 帝人株式会社 | 繊維用防炎加工剤 |
JP5762297B2 (ja) * | 2009-10-01 | 2015-08-12 | 大八化学工業株式会社 | 環状アルキレンホスホロハリダイトおよび環状リン酸エステルの製造方法 |
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EP2334691A1 (en) * | 2008-08-28 | 2011-06-22 | Dow Global Technologies LLC | Phosphorus-containing compounds and polymeric compositions comprising same |
WO2011052864A1 (ko) * | 2009-10-28 | 2011-05-05 | 코오롱글로텍주식회사 | 합성섬유 원단용 난연조성물 및 이를 이용한 후가공 난연 처리방법 |
WO2012161926A2 (en) * | 2011-05-25 | 2012-11-29 | Dow Global Technologies Llc | Phosphorus-containing compounds useful for making halogen-free, ignition-resistant polymers |
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CN112707935A (zh) * | 2020-12-26 | 2021-04-27 | 山西省化工研究所(有限公司) | 环保型芳香族磷酸酯盐成核剂的制备方法 |
CN114644656B (zh) * | 2022-02-25 | 2023-11-24 | 江苏恒力化纤股份有限公司 | 一种环状磷硼阻燃剂及阻燃抑烟聚酯薄膜的制备方法 |
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JP2010121067A (ja) * | 2008-11-20 | 2010-06-03 | Matsumoto Yushi Seiyaku Co Ltd | 非水系難燃性付与剤組成物および非水系難燃性樹脂組成物 |
JP2012517502A (ja) * | 2009-02-09 | 2012-08-02 | アイシーエル−アイピー アメリカ インコーポレイテッド | 難燃剤を含有するポリウレタンフォーム組成物、およびこの難燃剤を含有するポリウレタンフォーム組成物を製造するためのプロセス、難燃剤組成物およびこれらから製造されるポリウレタンフォーム |
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US8410298B1 (en) | 2010-05-14 | 2013-04-02 | Daihachi Chemical Industry Co., Ltd. | Phosphoric acid ester production method |
KR20130095639A (ko) * | 2010-05-14 | 2013-08-28 | 다이하치 카가쿠 고교 가부시키가이샤 | 인산 에스터 제조 방법 |
WO2011142136A1 (ja) | 2010-05-14 | 2011-11-17 | 大八化学工業株式会社 | リン酸エステルの製造方法 |
JP5773995B2 (ja) * | 2010-05-14 | 2015-09-02 | 大八化学工業株式会社 | リン酸エステルの製造方法 |
KR101864260B1 (ko) * | 2010-05-14 | 2018-06-04 | 다이하치 카가쿠 고교 가부시키가이샤 | 인산 에스터 제조 방법 |
JP2012167411A (ja) * | 2011-02-16 | 2012-09-06 | Daikyo Kagaku Kk | ポリエステル系繊維品の難燃加工剤と難燃加工方法 |
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JP2013011050A (ja) * | 2011-05-30 | 2013-01-17 | Toray Ind Inc | 複合強化繊維束、その製造方法、および成形材料 |
WO2013147294A1 (ja) * | 2012-03-29 | 2013-10-03 | 帝人株式会社 | 繊維用防炎加工剤 |
JPWO2013147294A1 (ja) * | 2012-03-29 | 2015-12-14 | 帝人株式会社 | 繊維用防炎加工剤 |
US10294351B2 (en) | 2012-03-29 | 2019-05-21 | Teijin Limited | Flameproofing agent for fibers |
Also Published As
Publication number | Publication date |
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CN101253184B (zh) | 2011-06-15 |
JPWO2007032277A1 (ja) | 2009-03-19 |
EP1925622A1 (en) | 2008-05-28 |
US8835541B2 (en) | 2014-09-16 |
TWI385176B (zh) | 2013-02-11 |
KR20080043776A (ko) | 2008-05-19 |
EP1925622A4 (en) | 2009-02-25 |
US20090227713A1 (en) | 2009-09-10 |
EP1925622B1 (en) | 2013-10-16 |
CN101253184A (zh) | 2008-08-27 |
KR101286484B1 (ko) | 2013-07-16 |
TW200722433A (en) | 2007-06-16 |
JP4909901B2 (ja) | 2012-04-04 |
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