JP4975248B2 - テトラハロフタレートエステルと燐含有難燃剤とのポリウレタン組成物用ブレンド - Google Patents
テトラハロフタレートエステルと燐含有難燃剤とのポリウレタン組成物用ブレンド Download PDFInfo
- Publication number
- JP4975248B2 JP4975248B2 JP2004503550A JP2004503550A JP4975248B2 JP 4975248 B2 JP4975248 B2 JP 4975248B2 JP 2004503550 A JP2004503550 A JP 2004503550A JP 2004503550 A JP2004503550 A JP 2004503550A JP 4975248 B2 JP4975248 B2 JP 4975248B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphorus
- reaction mixture
- phosphate
- flame retardant
- producing
- 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 - Fee Related
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 84
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 52
- 239000011574 phosphorus Substances 0.000 title claims abstract description 52
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 150000002148 esters Chemical class 0.000 title claims abstract description 31
- 229920002635 polyurethane Polymers 0.000 title description 8
- 239000004814 polyurethane Substances 0.000 title description 8
- 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 claims abstract description 71
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 43
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 43
- 239000011541 reaction mixture Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- 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 claims description 14
- 229920005862 polyol Polymers 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 13
- 239000006260 foam Substances 0.000 claims description 9
- UUEDINPOVKWVAZ-UHFFFAOYSA-N bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate Chemical group CCCCC(CC)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCC(CC)CCCC UUEDINPOVKWVAZ-UHFFFAOYSA-N 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- YWDFOLFVOVCBIU-UHFFFAOYSA-N 1-dimethoxyphosphorylpropane Chemical compound CCCP(=O)(OC)OC YWDFOLFVOVCBIU-UHFFFAOYSA-N 0.000 claims description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 3
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 claims description 3
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 claims description 3
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 2
- UZJUEEROTUVKNS-UHFFFAOYSA-N decyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCCCC)OC1=CC=CC=C1 UZJUEEROTUVKNS-UHFFFAOYSA-N 0.000 claims 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 16
- 230000000979 retarding effect Effects 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 description 14
- 239000000463 material Substances 0.000 description 11
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- -1 alkylaryl phosphates Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006261 foam material Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- YSDXOHIAKSQVEJ-UHFFFAOYSA-N 2-chloroethyl phosphono hydrogen phosphate Chemical class OP(O)(=O)OP(O)(=O)OCCCl YSDXOHIAKSQVEJ-UHFFFAOYSA-N 0.000 description 1
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- ASLWPAWFJZFCKF-UHFFFAOYSA-N tris(1,3-dichloropropan-2-yl) phosphate Chemical compound ClCC(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl ASLWPAWFJZFCKF-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37829902P | 2002-05-06 | 2002-05-06 | |
| US60/378,299 | 2002-05-06 | ||
| PCT/US2003/013804 WO2003095544A1 (en) | 2002-05-06 | 2003-05-05 | Blends of tetrahalophthalate esters and phosphoruscontaining flame retardants for polyurethane compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005529201A JP2005529201A (ja) | 2005-09-29 |
| JP2005529201A5 JP2005529201A5 (enExample) | 2012-04-05 |
| JP4975248B2 true JP4975248B2 (ja) | 2012-07-11 |
Family
ID=29420376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004503550A Expired - Fee Related JP4975248B2 (ja) | 2002-05-06 | 2003-05-05 | テトラハロフタレートエステルと燐含有難燃剤とのポリウレタン組成物用ブレンド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7423069B2 (enExample) |
| EP (1) | EP1501891B1 (enExample) |
| JP (1) | JP4975248B2 (enExample) |
| KR (1) | KR100777059B1 (enExample) |
| CN (1) | CN1649950A (enExample) |
| AT (1) | ATE377626T1 (enExample) |
| AU (1) | AU2003231270A1 (enExample) |
| BR (1) | BR0311836A (enExample) |
| DE (1) | DE60317320T2 (enExample) |
| IL (1) | IL164961A (enExample) |
| RU (1) | RU2004135863A (enExample) |
| WO (1) | WO2003095544A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003277675A1 (en) * | 2002-11-11 | 2004-06-03 | Central Glass Company, Limited | Vapor pressure depressant and use thereof |
| KR100901791B1 (ko) * | 2005-03-21 | 2009-06-11 | 그레이트 레이크스 케미칼 코퍼레이션 | 난연제 및 난연화된 중합체 |
| US8129457B2 (en) * | 2006-03-22 | 2012-03-06 | Chemtura Corporation | Flame retardant blends for flexible polyurethane foam |
| BRPI0710718A2 (pt) * | 2006-04-06 | 2012-01-31 | Albemarle Corp | composição de aditivo retardante de chama, composição retardante de chama e método de produção de uma composição de poliuretano flexìvel de componentes |
| WO2008118699A1 (en) * | 2007-03-27 | 2008-10-02 | Albemarle Corporation | Use of low triphenylphosphate, high phosphorous content isopropyl phenyl phosphates as flame retardants in polyurethane or polyisocyanurate foams |
| DE102008038054A1 (de) * | 2008-08-16 | 2010-02-18 | Lanxess Deutschland Gmbh | Halogenfreie, flammgeschützte Polyurethanschaumstoffe mit geringem Scorch |
| US9376766B2 (en) * | 2008-09-02 | 2016-06-28 | Interface, Inc. | Low weight-hardback carpet tile |
| US8083875B2 (en) | 2008-09-02 | 2011-12-27 | Interface, Inc. | Low weight carpet and carpet tile and methods of manufacture |
| DE102010028695A1 (de) | 2010-05-06 | 2011-11-10 | Evonik Röhm Gmbh | Polymethacrylimid-Schaumstoffe mit verminderter Entflammbarkeit sowie Verfahren zur Herstellung dieser |
| TW201231324A (en) | 2010-10-21 | 2012-08-01 | Interface Inc | Methods of cutting and installing carpet tiles |
| CN102167791B (zh) * | 2011-02-25 | 2012-08-29 | 北京万博汇佳科贸有限公司 | 一种用于软质聚氨酯泡沫的反应型阻燃剂及应用 |
| US20120235070A1 (en) * | 2011-03-18 | 2012-09-20 | Basf Se | Process for producing flame-retardant porous materials based on polyurea |
| US20120264839A1 (en) | 2011-04-14 | 2012-10-18 | Chemtura Corporation | Flame retardant blends for flexible polyurethane foams |
| CN106832881A (zh) * | 2017-01-16 | 2017-06-13 | 浙江省计量科学研究院 | 聚氨酯中邻苯二甲酸酯类增塑剂及磷系阻燃剂标准样品及样品制备方法 |
| PL3606971T3 (pl) * | 2017-09-21 | 2022-05-23 | Icl-Ip America Inc. | Reaktywne mieszanki opóźniające palenie do elastycznej pianki poliuretanowej |
| WO2020030549A1 (de) * | 2018-08-08 | 2020-02-13 | Covestro Deutschland Ag | Phosphinat als flammschutzadditiv für pur-/pir-hartschaumstoffe |
| CN110804256B (zh) * | 2019-10-24 | 2022-09-13 | 瑞鑫集团有限公司 | 一种防火电缆 |
| US12102247B2 (en) | 2021-05-03 | 2024-10-01 | Interface, Inc. | Non-square rectangular flooring tiles and methods for cutting same |
| US20240182629A1 (en) * | 2022-11-29 | 2024-06-06 | Lear Corporation | Polyurethane foam emissions reduction additive |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4246360A (en) * | 1977-07-22 | 1981-01-20 | Monsanto Company | Fire retardant, non-dripping flexible polyurethane foam |
| EP0005903B1 (en) | 1978-05-30 | 1983-06-01 | Imperial Chemical Industries Plc | Process for the manufacture of polyurea foams |
| US4407981A (en) * | 1980-12-19 | 1983-10-04 | Stauffer Chemical Company | Flame retardant mixture for polyurethanes |
| US4407891A (en) * | 1981-11-20 | 1983-10-04 | Ppg Industries, Inc. | Low temperature reduction process for large photomasks |
| US4954542A (en) * | 1988-03-25 | 1990-09-04 | Pennwalt Corporation | Tetrahalophthalate esters as flame retardants for polybutylene terephthalate resins (PBT) |
| EP0339074A4 (en) | 1987-10-30 | 1991-07-03 | Pennwalt Corporation | Tetrahalophthalate esters as flame retardants for certain resins |
| US4892683A (en) * | 1988-05-20 | 1990-01-09 | Gary Chemical Corporation | Flame retardant low smoke poly(vinyl chloride) thermoplastic compositions |
| US4880844A (en) * | 1988-05-27 | 1989-11-14 | Akzo America Inc. | Flame laminatable polyether urethane foam |
| US5036121A (en) * | 1988-09-06 | 1991-07-30 | The B. F. Goodrich Company | Flame and smoke retardant cable insulation and jacketing compositions |
| US5328627A (en) * | 1988-10-14 | 1994-07-12 | Elf Atochem North America, Inc. | Fire resistant hydraulic fluids |
| US5728760A (en) * | 1995-04-11 | 1998-03-17 | Great Lakes Chemical Corporation | Use of ring-brominated benzoate compounds as flame retardants and/or plasticizers |
| KR20010013947A (ko) * | 1997-06-18 | 2001-02-26 | 데이비드 디. 샌더스 | 신규한 난연성 가소제 |
| EP1037942A1 (en) * | 1997-12-13 | 2000-09-27 | Huntsman Ici Chemicals Llc | Process for making rigid and flexible polyurethane foams |
-
2003
- 2003-05-05 RU RU2004135863/04A patent/RU2004135863A/ru not_active Application Discontinuation
- 2003-05-05 JP JP2004503550A patent/JP4975248B2/ja not_active Expired - Fee Related
- 2003-05-05 WO PCT/US2003/013804 patent/WO2003095544A1/en not_active Ceased
- 2003-05-05 CN CNA038101890A patent/CN1649950A/zh active Pending
- 2003-05-05 EP EP03724407A patent/EP1501891B1/en not_active Expired - Lifetime
- 2003-05-05 AU AU2003231270A patent/AU2003231270A1/en not_active Abandoned
- 2003-05-05 DE DE60317320T patent/DE60317320T2/de not_active Expired - Lifetime
- 2003-05-05 US US10/429,429 patent/US7423069B2/en not_active Expired - Fee Related
- 2003-05-05 KR KR1020047017568A patent/KR100777059B1/ko not_active Expired - Fee Related
- 2003-05-05 AT AT03724407T patent/ATE377626T1/de not_active IP Right Cessation
- 2003-05-05 BR BR0311836-3A patent/BR0311836A/pt active Search and Examination
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Also Published As
| Publication number | Publication date |
|---|---|
| BR0311836A (pt) | 2005-04-12 |
| JP2005529201A (ja) | 2005-09-29 |
| EP1501891A1 (en) | 2005-02-02 |
| US20040030011A1 (en) | 2004-02-12 |
| KR20050007363A (ko) | 2005-01-17 |
| WO2003095544A1 (en) | 2003-11-20 |
| EP1501891B1 (en) | 2007-11-07 |
| DE60317320D1 (de) | 2007-12-20 |
| IL164961A (en) | 2009-12-24 |
| IL164961A0 (en) | 2005-12-18 |
| KR100777059B1 (ko) | 2007-11-28 |
| US7423069B2 (en) | 2008-09-09 |
| RU2004135863A (ru) | 2005-06-27 |
| CN1649950A (zh) | 2005-08-03 |
| ATE377626T1 (de) | 2007-11-15 |
| AU2003231270A1 (en) | 2003-11-11 |
| DE60317320T2 (de) | 2008-08-28 |
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