JP5066178B2 - 難燃剤としてのピリミジン誘導体 - Google Patents
難燃剤としてのピリミジン誘導体 Download PDFInfo
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- JP5066178B2 JP5066178B2 JP2009508309A JP2009508309A JP5066178B2 JP 5066178 B2 JP5066178 B2 JP 5066178B2 JP 2009508309 A JP2009508309 A JP 2009508309A JP 2009508309 A JP2009508309 A JP 2009508309A JP 5066178 B2 JP5066178 B2 JP 5066178B2
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 78
- 150000003230 pyrimidines Chemical class 0.000 title description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
- 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 46
- 239000000203 mixture Substances 0.000 claims abstract description 43
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- 238000000034 method Methods 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 202
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- 125000003118 aryl group Chemical group 0.000 claims description 41
- 229920000642 polymer Polymers 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 29
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
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- 239000000654 additive Substances 0.000 claims description 19
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
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- 230000000996 additive effect Effects 0.000 claims description 7
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 125000005156 substituted alkylene group Chemical group 0.000 claims description 5
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- 150000002443 hydroxylamines Chemical class 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
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- VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-UHFFFAOYSA-N 0.000 claims description 3
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims description 3
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- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 2
- 230000000979 retarding effect Effects 0.000 abstract 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000000178 monomer Substances 0.000 description 11
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- 239000000460 chlorine Substances 0.000 description 10
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- 150000001412 amines Chemical class 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
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- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
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- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
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- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
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- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 125000005065 undecenyl group Chemical class C(=CCCCCCCCCC)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
-
- 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
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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)
- Fireproofing Substances (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06113371 | 2006-05-02 | ||
| EP06113371.6 | 2006-05-02 | ||
| EP06125786.1 | 2006-12-11 | ||
| EP06125786 | 2006-12-11 | ||
| PCT/EP2007/053948 WO2007128678A1 (en) | 2006-05-02 | 2007-04-23 | Derivatives of pyrimidines as flame retardants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009536975A JP2009536975A (ja) | 2009-10-22 |
| JP2009536975A5 JP2009536975A5 (enExample) | 2010-06-24 |
| JP5066178B2 true JP5066178B2 (ja) | 2012-11-07 |
Family
ID=38473967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009508309A Expired - Fee Related JP5066178B2 (ja) | 2006-05-02 | 2007-04-23 | 難燃剤としてのピリミジン誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8022122B2 (enExample) |
| EP (1) | EP2013279B1 (enExample) |
| JP (1) | JP5066178B2 (enExample) |
| KR (1) | KR20090009799A (enExample) |
| AT (1) | ATE462755T1 (enExample) |
| DE (1) | DE602007005628D1 (enExample) |
| ES (1) | ES2343147T3 (enExample) |
| PL (1) | PL2013279T3 (enExample) |
| TW (1) | TW200808886A (enExample) |
| WO (1) | WO2007128678A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101486839B1 (ko) | 2007-12-21 | 2015-01-30 | 바스프 에스이 | 입체 장애 아민을 포함하는 난연제 조성물 |
| JP5417770B2 (ja) * | 2008-08-27 | 2014-02-19 | 東洋インキＳｃホールディングス株式会社 | 難燃剤および難燃性樹脂組成物 |
| JP5347407B2 (ja) * | 2008-09-26 | 2013-11-20 | 東洋インキＳｃホールディングス株式会社 | 難燃剤および難燃性樹脂組成物 |
| WO2011007687A1 (ja) * | 2009-07-17 | 2011-01-20 | 東レ株式会社 | 難燃性熱可塑性樹脂組成物および成形品 |
| CN104204055B (zh) * | 2011-12-30 | 2016-05-25 | 提克纳有限责任公司 | 用于发光装置的反射器 |
| JP6156018B2 (ja) * | 2013-09-26 | 2017-07-05 | Dic株式会社 | 難燃性マスターバッチ、難燃性樹脂組成物およびその製造方法 |
| US20170313855A1 (en) | 2014-11-24 | 2017-11-02 | Lubrizol Advanced Materials, Inc. | Novel coupled uracil compound for vinyl chloride polymer resins |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0065934B1 (de) * | 1981-05-26 | 1985-08-07 | Ciba-Geigy Ag | Mit Aminouracilen stabilisierte chlorhaltige Thermoplaste |
| US4656209A (en) * | 1982-05-26 | 1987-04-07 | Ciba-Geigy Corporation | Chlorinated thermoplastics stabilized with aminouracils |
| ATA86392A (de) * | 1992-04-27 | 1997-04-15 | Chemie Linz Gmbh | Verwendung von guanidinbarbituraten und guanidinthiobarbituraten als flammhemmer für kunststoffe sowie flammfeste kunststoffe mit einem gehalt an guanidinbarbituraten oder guanidinthiobarbituraten |
| EP0661342B1 (en) | 1993-12-28 | 2003-04-02 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Additive for thermoplastic resins and flame retardant resin composition |
| DK1327661T3 (da) * | 1995-10-13 | 2006-01-02 | Crompton Vinyl Additives Gmbh | Stabilisatorkombinationer til chlorholdige polymerer |
| MY114466A (en) * | 1996-09-25 | 2002-10-31 | Crompton Vinyl Additives Gmbh | Rigid pvc stabilised with n, n-dimethyl-6-aminouracils |
| ES2196467T3 (es) * | 1998-01-16 | 2003-12-16 | Crompton Vinyl Additives Gmbh | Sistema de estabilizadores para polimeros con un contenido en cloro. |
| DE59902320D1 (de) * | 1998-06-26 | 2002-09-19 | Crompton Vinyl Additives Gmbh | In 5-Stellung substituierte 6-Aminouracile als Stabilisatoren für halogen-haltige Polymere |
| WO2000012608A1 (en) | 1998-08-31 | 2000-03-09 | General Electric Company | Flame resistant polyketone resin compositions |
| DE19933901A1 (de) * | 1999-07-22 | 2001-02-01 | Clariant Gmbh | Flammschutzmittel-Kombination |
| US6987139B2 (en) | 2001-10-19 | 2006-01-17 | Matsushita Electric Industrial Co., Ltd. | Polymer composition |
| EP1492842B1 (en) | 2002-03-28 | 2006-04-12 | Equipolymers GmbH | Compounds useful for reducing acetaldehyde content of polyethylene terephthalate, their use and products resulting therefrom |
| US7498368B2 (en) | 2003-05-26 | 2009-03-03 | Polyplastics Co., Ltd. | Flame-retardant resin composition |
| CN1757665A (zh) * | 2004-10-07 | 2006-04-12 | 罗门哈斯公司 | 用于含卤素的乙烯基聚合物的热稳定剂组合物 |
-
2007
- 2007-04-23 EP EP07728405A patent/EP2013279B1/en not_active Not-in-force
- 2007-04-23 KR KR1020087024687A patent/KR20090009799A/ko not_active Ceased
- 2007-04-23 US US12/226,840 patent/US8022122B2/en not_active Expired - Fee Related
- 2007-04-23 JP JP2009508309A patent/JP5066178B2/ja not_active Expired - Fee Related
- 2007-04-23 ES ES07728405T patent/ES2343147T3/es active Active
- 2007-04-23 PL PL07728405T patent/PL2013279T3/pl unknown
- 2007-04-23 DE DE602007005628T patent/DE602007005628D1/de active Active
- 2007-04-23 AT AT07728405T patent/ATE462755T1/de not_active IP Right Cessation
- 2007-04-23 WO PCT/EP2007/053948 patent/WO2007128678A1/en not_active Ceased
- 2007-04-30 TW TW096115294A patent/TW200808886A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2013279A1 (en) | 2009-01-14 |
| US8022122B2 (en) | 2011-09-20 |
| US20090131565A1 (en) | 2009-05-21 |
| EP2013279B1 (en) | 2010-03-31 |
| JP2009536975A (ja) | 2009-10-22 |
| DE602007005628D1 (de) | 2010-05-12 |
| TW200808886A (en) | 2008-02-16 |
| KR20090009799A (ko) | 2009-01-23 |
| ATE462755T1 (de) | 2010-04-15 |
| ES2343147T3 (es) | 2010-07-23 |
| PL2013279T3 (pl) | 2010-09-30 |
| WO2007128678A1 (en) | 2007-11-15 |
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