CN102712668A - 经磷取代的烷氧胺化合物 - Google Patents
经磷取代的烷氧胺化合物 Download PDFInfo
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- CN102712668A CN102712668A CN2011800060543A CN201180006054A CN102712668A CN 102712668 A CN102712668 A CN 102712668A CN 2011800060543 A CN2011800060543 A CN 2011800060543A CN 201180006054 A CN201180006054 A CN 201180006054A CN 102712668 A CN102712668 A CN 102712668A
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- CN
- China
- Prior art keywords
- alkyl
- phenyl
- group
- methyl
- hydrogen
- 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.)
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- 125000005262 alkoxyamine group Chemical class 0.000 title 1
- -1 phospho groups Chemical group 0.000 claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 239000003063 flame retardant Substances 0.000 claims abstract description 35
- 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 21
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 20
- 239000011159 matrix material Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 abstract description 38
- 150000001412 amines Chemical class 0.000 abstract description 9
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- 239000000126 substance Substances 0.000 description 40
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 8
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
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- 239000002904 solvent Substances 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 125000005499 phosphonyl group Chemical group 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
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- 239000012044 organic layer Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- 230000000630 rising effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AVIZTSRRMBGYCJ-UHFFFAOYSA-N tetraazanium phosphonato phosphate 1,3,5-triazine-2,4,6-triamine Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].NC1=NC(N)=NC(N)=N1.[O-]P([O-])(=O)OP([O-])([O-])=O AVIZTSRRMBGYCJ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
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- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- 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
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- 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
- C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
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- 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
- C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—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 the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
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- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
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Abstract
本发明涉及所谓空间位阻胺(HALS)类化合物,其被磷基取代。本发明还涉及阻燃剂组合物,其中将这些化合物加入聚合物基质中。
Description
本发明涉及新型经磷取代的烷氧胺化合物和含该新型经磷(phospho)取代的烷氧胺化合物的阻燃剂组合物。
向聚合材料(合成或天然材料)中加入阻燃剂以提高该聚合物的阻燃性。取决于它们的组成,阻燃剂可呈固相、液相或气相以化学方式如通过释放氮气作为泡沫状物质和/或物理方式如通过产生泡沫覆盖物起作用。阻燃剂在燃烧过程的特定阶段如在加热、分解、点火或火焰蔓延期间起干扰作用。
仍然存在对可用于不同聚合物基质的具有改进效力的阻燃剂的需求。对于安全性和环境要求的提高标准导致更严格的控制。尤其已知的含卤素阻燃剂不再符合所有必需要求。因此,优选无卤素阻燃剂,尤其就其在与燃烧相关的烟密度方面的较佳性能而言。改进的热稳定性、较小的腐蚀性、与聚合物基质的相互作用降低和环境友好性为无卤素阻燃剂组合物的其他优点。
美国专利说明书5,393,812公开了聚烯烃组合物,其通过加入卤化烃基磷酸酯或膦酸酯阻燃剂而用作阻燃剂,且可通过HALS对UV光降解稳定。
EP-A 792 911公开了烷氧胺-HALS在改进聚烯烃阻燃性中的用途。WO 99/00450公开了烷氧胺-HALS在改进阻燃性中的用途。
WO 01/90113公开了经磷取代的羟胺酯作为聚合引发剂。WO 2003/082711公开了含有与其他阻燃剂组合的羟胺酯的阻燃剂组合物。
惊人地发现,在将经磷基取代的所谓空间位阻胺(HALS)的烷氧胺衍生物类化合物加入聚合物基质中的情况下,获得具有优异阻燃性的聚合物。
本发明涉及下式化合物:
其中:
R为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1-R4为甲基;或
R1与R2中一个以及R3与R4中一个为甲基;且R1与R2中的另一个以及
R3与R4中的另一个为乙基;
R5和R6相互独立地为氢或甲基;和
Z为以下部分式的基团:
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷基、C1-C4烷氧基、苯基或苯氧基;
Rc为氢或C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基、苯基或苯氧基,或一起为C2-C8亚烷二氧基;或
Z为以下部分式的基团:
其中:
Rc为氢或C1-C12烷基;或
Z为以下部分式的基团:
其中:
Rc'为C2-C8亚烷基;
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、
苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1′与R2′中一个以及R3′与R4′中一个为甲基;且R1′与R2′中的另一个以及
R3′与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
Rd'和Re'相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为以下部分式的基团:
其中:
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1'与R2′中一个以及R3'与R4′中一个为甲基;且R1′与R2′中的另一个以及R3'与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
R7为苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基或(C1-C4烷基)1-3苯基-C1-C4烷基。
本发明还涉及包含以下组分的组合物:
a)化合物(I),其中R、R1-R6和Z如上所定义;和
b)聚合物基质;
和一种赋予该聚合物基质以阻燃性的方法。包含本发明化合物(I)的组合物显示出优异的阻燃性能。取决于该聚合物基质中的组分a)和b)的浓度,达到根据UL-94(Underwriter's Laboratories Subject 94)的V-0或V-2等级和相关测试方法如根据DIN 4102B2中的其他优异等级。
本发明的优选实施方案涉及如下化合物(I),其中:
R为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1-R4为甲基;或
R1与R2中一个以及R3与R4中一个为甲基;且R1与R2中的另一个以及R3与R4中的另一个为乙基;
R5和R6相互独立地为氢或甲基;和
Z为以下部分式的基团:
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷基、C1-C4烷氧基、苯基或苯氧基;
Rc为氢或C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基、苯基或苯氧基,或一起为C2-C8亚烷二氧基;或
Z为以下部分式的基团:
其中:
Rc为氢或C1-C12烷基;或
Z为以下部分式的基团:
其中:
Rc'为C2-C8亚烷基;
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1'与R2′中一个以及R3'与R4′中一个为甲基;且R1'与R2′中的另一个以及R3'与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
Rd'和Re'相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Rd'和Re'一起为C2-C8亚烷二氧基。
本发明特别优选的实施方案涉及如下化合物(I),其中:
R为氢或C1-C12烷基;
R1-R4为甲基;
R5和R6为氢;和
Z如上所定义。
本发明高度优选的实施方案涉及如下化合物(I),其中:
R为氢或C1-C12烷基;
R1-R4为甲基;
R5和R6为氢;和
Z为部分式(A)、(B)或(C)的基团,
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷氧基或苯基;
Rc为C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基或苯基,或一起为C2-C8亚烷二氧基;
或
Z为部分式(D)的基团,
其中:
Rc为C1-C12烷基;或
Z为部分式(E)的基团,
其中:
Rc'为C2-C8亚烷基;
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为氢;和
Rd'和Re'相互独立地为C1-C4烷氧基或苯基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为部分式(F)的基团,
其中:
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为甲基;和
R7为苯基。
本发明的首选实施方案涉及如下化合物(I),其中:
R为C1-C8烷基;
R1-R4为甲基;
R5和R6为氢;和
Z为部分式(A)、(B)或(C)的基团,
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷氧基或苯基;
Rc为C1-C6烷基;和
Rd和Re相互独立地为C1-C4烷氧基或苯基,或一起为C2-C8亚烷二氧基;
或
Z为部分式(D)的基团,
其中:
Rc为C1-C8烷基;或
Z为部分式(E)的基团,
其中:
Rc'为C2-C8亚烷基;
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为氢;和
Rd'和Re'相互独立地为C1-C4烷氧基或苯基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为部分式(F)的基团,
其中:
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为甲基;和
R7为苯基。
高度优选选自以下的化合物(I):
或者,选自以下的化合物(I):
或者,选自以下的根据权利要求1的化合物(I):
或者,下式化合物(I):
或者,选自以下的化合物(I):
或者,选自以下的化合物(I):
本发明的另一实施方案涉及通过本身已知的常规方法制备化合物(I)的方法,尤其是制备上述优选实施方案的化合物(I)的方法,特别是制备上述特定化合物的方法。
用于本发明描述中的术语和表述优选具有以下含义:
定义为C1-C12烷基的R为甲基、乙基、1-或2-丙基或直链或支化C4-C12烷基,例如正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基或正十二烷基;
羟基-C2-C12烷基为2-羟乙基或2-或3-羟丙基或在2-位或如果可能任意较高位置上被羟基取代的任何上述C4-C12烷基;
二羟基-C3-C12烷基为例如2,3-二羟丙基或在2-和3-位被两个羟基取代的任何上述C4-C12烷基或如果可能在更高位置上被两个羟基取代的C4-C12烷基。
苯基-C1-C4烷基为例如苄基或1-或2-苯乙基。
(C1-C4烷基)1-3苯基为例如邻-、间-和对-甲苯基、二甲苯基或三甲苯基。
(C1-C4烷基)1-3苯基-C1-C4烷基为例如2-或6-甲基苄基。
(C1-C4烷氧基)1-3苯基为例如邻-、间-或对-甲氧基或乙氧基苯基。
(C1-C4烷氧基)1-3苯基-C1-C4烷基为例如邻-、间-或对-甲氧基或乙氧基苄基。
C3-C8环烷基优选为环戊基或环己基。
C3-C8环烷基-C1-C4烷基为例如环戊基甲基或环己基乙基或1-或2-环戊基乙基或1-或2-环己基乙基。
-C(=O)-C1-C19烷基为C1-C20烷酸的酰基,例如乙酰基、新戊酰基、月桂酰基(C12)、肉豆蔻酰基(C14)、棕榈酰基(C16)或硬脂酰基(C18)。
代表性化合物(I)为:
代表性化合物(I)为:
在其中Z为部分式的化合物(I)的实施方案中,Rc为氢或C1-C12烷基,尤其是C1-C8烷基;和
Rd和Re相互独立地为C1-C4烷氧基,尤其是甲氧基或乙氧基,苯基或苯氧基;或一起为C2-C8亚烷二氧基,例如亚乙二氧基、1,3-三亚甲基二氧基或2,2-二甲基-1,3-亚丙二氧基。
代表性化合物(I)为:
代表性化合物(I)为:
代表性化合物(I)为:
在其中Z为部分式的基团的化合物(I)的实施方案中,R'、R1'-R4'和R5'与R6'如R、R1-R4和R5与R6所定义。R7为苯基;具有上述含义的苯基-C1-C4烷基、(C1-C4烷基)1-3苯基或(C1-C4烷基)1-3苯基-C1-C4烷基。
代表性化合物(I)为:
该化合物(I)通过实施例中所阐述的已知方法制备。
术语聚合物基质在其范围内包括热塑性聚合物或热固性聚合物。
合适热塑性聚合物的非穷举性列举如下所示:
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁-1-烯、聚-4-
甲基戊-1-烯、聚乙烯基环己烷、聚异戊二烯或聚丁二烯,以及环烯烃如环戊烯或降冰片烯的聚合物,聚乙烯(其任选可交联),例如高密度聚亚甲基(HDPE)、高密度和高分子量聚乙烯(HDPE-HMW)、高密度和超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
聚烯烃,即前面段落中例举的单烯烃聚合物,优选聚乙烯和聚丙烯,可以通过不同方法制备,尤其通过下列方法制备:
a)自由基聚合(通常在高压和升高的温度下)。
b)使用通常含有一种或一种以上周期表第IVb、Vb、VIb或VIII族金属的催化剂的催化聚合。这些金属通常具有一个或一个以上配体,通常是可为π-或σ-配位的氧化物、卤化物、醇盐、酯、醚、胺、烷基化物、链烯基化物和/或芳基化物。这些金属配合物可为游离形式或固定在基材上,通常在活化氯化镁、氯化钛(III)、氧化铝或氧化硅上。这些催化剂可溶于或不溶于聚合介质中。所述催化剂本身可用于聚合或者可使用其它活化剂,通常为烷基金属、金属氢化物、金属烷基卤化物、金属烷基氧化物或金属烷基氧烷(alkyloxane),其中所述金属为周期表第Ia、IIa和/或IIIa族的元素。所述活化剂可方便地用其它酯、醚和胺或甲硅烷基醚基团改性。这些催化剂体系通常称为Philips、Standard Oil Indiana、齐格勒(-纳塔)、TNZ(杜邦)、茂金属或单中心催化剂(SSC)。
2.1)下提及的聚合物的混合物,例如聚丙烯与聚异丁烯、聚丙烯与聚乙烯的混合物(例如PP/HDPE、PP/LDPE)和不同种类聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和二烯烃相互之间或与其它乙烯基单体的共聚物,例如乙烯/丙烯共聚物,线性低密度聚乙烯(LLDPE)及其与低密度聚乙烯(LDPE)的混合物,丙烯/丁-1-烯共聚物,丙烯/异丁烯共聚物,乙烯/丁-1-烯共聚物,乙烯/己烯共聚物,乙烯/甲基戊烯共聚物,乙烯/庚烯共聚物,乙烯/辛烯共聚物,乙烯/乙烯基环己烷共聚物,乙烯/环烯烃共聚物(例如乙烯/降冰片烯,例如COC),乙烯/1-烯烃共聚物,其中1-烯烃原位产生;丙烯/丁二烯共聚物,异丁烯/异戊二烯共聚物,乙烯/乙烯基环己烯共聚物,乙烯/丙烯酸烷基酯共聚物,乙烯/甲基丙烯酸烷基酯共聚物,乙烯/乙酸乙烯酯共聚物或乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和二烯如己二烯、二聚环戊二烯或亚乙基降冰片烯的三元共聚物;以及这些共聚物相互之间及与上述1)下提及聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-乙酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA和交替或无规聚烯烃/一氧化碳共聚物及其与其它聚合物如聚酰胺的混合物。
4.烃树脂(例如C5-C9),包括其氢化改性物(例如增粘剂)以及聚烯烃和淀粉的混合物。
上述均聚物和共聚物可以具有立体结构,包括间规、等规、半等规或无规立构;其中优选无规立构聚合物。还包括立构嵌段聚合物。
5.聚苯乙烯、聚(对甲基苯乙烯)、聚(α-甲基苯乙烯)。
6.衍生于乙烯基芳族单体的芳族均聚物和共聚物,所述单体包括苯乙烯,α-甲基苯乙烯,乙烯基甲苯的所有异构体,尤其是对乙烯基甲苯,乙基苯乙烯、丙基苯乙烯、乙烯基联苯、乙烯基萘和乙烯基蒽的所有异构体及其混合物。均聚物和共聚物可具有立体结构,包括间规、等规、半等规或无规立构排列;其中优选无规立构聚合物。还包括立构嵌段聚合物。
a)包括上述乙烯基芳族单体和选自乙烯、丙烯、二烯、腈、酸、马来酸酐、马来酰亚胺、乙酸乙烯酯和氯乙烯或丙烯酸衍生物及其混合物的共聚单体的共聚物,例如苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/乙烯(共聚物)、苯乙烯/甲基丙烯酸烷基酯、苯乙烯/丁二烯/丙烯酸烷基酯、苯乙烯/丁二烯/甲基丙烯酸烷基酯、苯乙烯/马来酸酐、苯乙烯/丙烯腈/丙烯酸甲酯;高冲击强度的苯乙烯共聚物和其它聚合物如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物的混合物;以及苯乙烯的嵌段共聚物,例如苯乙烯/丁二烯/苯乙烯、苯乙烯/异戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
b)衍生于6.)下所提到的聚合物的氢化的氢化芳族聚合物,尤其包括通过氢化无规立构聚苯乙烯得到的聚环己基乙烯(PCHE),也常称为聚乙烯基环己烷(PVCH)。
c)衍生于6a)下所提到的聚合物的氢化的氢化芳族聚合物。均聚物和共聚物可以具有立体结构,包括间规、等规、半等规或无规立构排列;其中优选无规立构聚合物。还包括立构嵌段聚合物。
7.乙烯基芳族单体如苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯接枝聚丁二烯,苯乙烯接枝聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物;苯乙烯和丙烯腈(或甲基丙烯腈)接枝聚丁二烯;苯乙烯、丙烯腈和甲基丙烯酸甲酯接枝聚丁二烯;苯乙烯和马来酸酐接枝聚丁二烯;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺接枝聚丁二烯;苯乙烯和马来酰亚胺接枝聚丁二烯;苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯接枝聚丁二烯;苯乙烯和丙烯腈接枝乙烯/丙烯/二烯三元共聚物;苯乙烯和丙烯腈接枝聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯;苯乙烯和丙烯腈接枝丙烯酸酯/丁二烯共聚物,及其与6)下所列共聚物的混合物,例如称作ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤素的聚合物,例如聚氯丁二烯、氯化橡胶、异丁烯/异戊二烯的氯化和溴化共聚物(卤丁基橡胶)、氯化或磺基氯化聚乙烯、乙烯和氯代乙烯的共聚物、表氯醇均聚物和共聚物,尤其是含卤素乙烯基化合物的聚合物,例如聚氯乙烯、聚偏氯乙烯、聚氟乙烯、聚偏氟乙烯,及其共聚物如氯乙烯/偏氯乙烯、氯乙烯/乙酸乙烯酯或偏氯乙烯/乙酸乙烯酯共聚物。
9.衍生于α,β-不饱和酸及其衍生物的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯;用丙烯酸丁酯冲击改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
10.9)下所提到的单体相互之间或与其他不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷基酯共聚物、丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/卤乙烯共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11.衍生于不饱和醇和胺或其酰基衍生物或缩醛的聚合物,例如聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙基酯或聚烯丙基蜜胺;以及它们与上面1中所提到的烯烃的共聚物。
12.环醚的均聚物和共聚物,如聚亚烷基二醇、聚氧乙烯、聚氧丙烯或其与二缩水甘油基醚的共聚物。
13.聚缩醛如聚甲醛和含有氧化乙烯作为共聚单体的那些聚甲醛;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯醚和聚苯硫醚,以及聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.一方面衍生于羟基封端的聚醚、聚酯或聚丁二烯且另一方面衍生于脂族或芳族多异氰酸酯的聚氨酯,以及其前体。
16.衍生于二胺和二羧酸和/或衍生于氨基羧酸或相应内酰胺的聚酰胺和共聚酰胺,例如聚酰胺4,聚酰胺6,聚酰胺4/10、5/10、6/6、6/10、6/9、6/12、4/6、12/12,聚酰胺11,聚酰胺12,来源于间苯二甲胺和己二酸的芳族聚酰胺;由六亚甲基二胺和间苯二甲酸或/和对苯二甲酸制备的聚酰胺(含或不含作为改性剂的弹性体),例如聚对苯二甲酰2,4,4-三甲基六亚甲基二胺或聚间苯二甲酰间苯二胺;还有上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合或接枝弹性体的嵌段共聚物;或与聚醚如聚乙二醇、聚丙二醇或聚四亚甲基二醇的嵌段共聚物;以及用EPDM或ABS改性的聚酰胺或共聚酰胺;以及在加工过程中缩合的聚酰胺(RIM聚酰胺体系)。
17.聚脲、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲类和聚苯并咪唑类。
18.衍生自二羧酸和二醇和/或衍生于羟基羧酸或相应内酯的聚酯,例如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚-1,4-二羟甲基环己烷对苯二甲酸酯、聚萘二甲酸亚烷基二醇酯(PAN)和聚羟基苯甲酸酯以及衍生于羟基封端的聚醚的嵌段共聚醚酯,还有用聚碳酸酯或MBS改性的聚酯。
19.聚酮。
20.聚砜、聚醚砜和聚醚酮。21.上述聚合物的共混物(高分子共混物),例如PP/EPDM,聚酰胺/EPDM或ABS,PVC/EVA,PVC/ABS,PVC/MBS,PC/ABS,PBTP/ABS,PC/ASA,PC/PBT,PVC/CPE,PVC/丙烯酸酯,POM/热塑性PUR,PC/热塑性PUR,POM/丙烯酸酯,POM/MBS,PPO/HIPS,PPO/PA 6.6和共聚物,PA/HDPE,PA/PP,PA/PPO,PBT/PC/ABS或PBT/PET/PC。
22.对应于以下通式的聚碳酸酯:
该类聚碳酸酯可通过界面方法或熔体方法(催化转酯化)获得。该聚碳酸酯可为支化或线性结构且可包括任何官能性取代基。聚碳酸酯共聚物和聚碳酸酯共混物也在本发明范围内。应将术语聚碳酸酯解释为包括与其他热塑性材料的共聚物和共混物。制造聚碳酸酯的方法在例如美国专利说明书3,030,331、3,169,121、4,130,458、4,263,201、4,286,083、4,552,704、5,210,268和5,606,007中已知。还可使用两种或更多种不同分子量的聚碳酸酯的组合。
优选可由二酚如双酚A与碳酸酯源的反应获得的聚碳酸酯。合适二酚的实例为:
该碳酸酯源可为羰基卤、碳酸酯或卤甲酸酯。合适的碳酸酯卤化物为光气或羰基溴。合适的碳酸酯为碳酸二烷酯如碳酸二甲酯或碳酸二乙酯,碳酸二苯酯,碳酸苯基·烷基苯酯如碳酸苯基甲苯酯,碳酸二烷酯如碳酸二甲酯或碳酸二乙酯,碳酸二(卤苯基)酯如碳酸二(氯苯基)酯、碳酸二(溴苯基)酯、碳酸二(三氯苯基)酯或碳酸二(三氯苯基)酯,碳酸二(烷基苯基)酯碳酸二-甲苯基酯,碳酸萘酯,碳酸二氯萘酯及其他。
包括聚碳酸酯或聚碳酸酯共混物的上述聚合物基质为其中存在间苯二甲酸酯/对苯二甲酸酯-间苯二酚链段的聚碳酸酯共聚物。该类聚碳酸酯可购自例如SLX(General Electrics Co.USA)。组分b)的其他聚合物基质可以混合物或共聚物形式额外含有宽范围的合成聚合物,包括聚烯烃、聚苯乙烯、聚酯、聚醚、聚酰胺、聚(甲基)丙烯酸酯、热塑性聚氨酯、聚砜、聚缩醛和PVC,其包含合适的增容剂。例如,该聚合物基质可额外含有选自以下的热塑性聚合物:由聚烯烃构成的树脂、热塑性聚氨酯、苯乙烯聚合物及其共聚物。特定实施方案包括聚丙烯(PP)、聚乙烯(PE)、聚酰胺(PA)、聚对苯二甲酸丁二醇酯(PBT)、聚对苯二甲酸乙二醇酯(PET)、经二醇改性的聚亚环己基亚甲基对苯二甲酸酯(PCTG)、聚砜(PSU)、聚甲基丙烯酸甲酯(PMMA)、热塑性聚氨酯(TPU)、丙烯腈-丁二烯-苯乙烯(ABS)、丙烯腈-苯乙烯-丙烯酸酯(ASA)、丙烯腈-乙烯-丙烯-苯乙烯(AES)、苯乙烯-马来酸酐(SMA)或高耐冲击性聚苯乙烯(HIPS)。
23.由双-或多官能环氧化合物构成的环氧树脂,其中存在直接连接至碳、氧、氮或硫原子的至少两个以下部分式的环氧基:
其中q为0,R1和R3均为氢且R2为氢或甲基;或其中q为0或1,R1和R3一起形成基团-CH2-CH2-或-CH2-CH2-CH2-且R2为氢。
合适的硬化剂组分为例如胺和酐硬化剂,例如多胺,如乙二胺、二亚乙基三胺、三亚乙基三胺、六亚甲基二胺、甲烷二胺、N-氨基乙基哌嗪、二氨基二苯基甲烷[DDM]、DDM的经烷基取代的衍生物、异佛尔酮二胺[IPD]、二氨基二苯基砜[DDS]、4,4'-亚甲基二苯胺[MDA]或间苯二胺[MPDA]),聚酰胺,烷基/烯基咪唑,双氰胺[DICY],1,6-六亚甲基双氰基胍,或酸酐,如十二碳烯基琥珀酸酐、六氢邻苯二甲酸酐、四氢邻苯二甲酸酸酐、邻苯二甲酸酐、均苯四甲酸酐及其衍生物。
本发明的优选实施方案涉及包括热塑性聚合物作为组分c)的组合物。优选的热塑性聚合物包括聚烯烃均聚物和共聚物,尤其是聚丙烯、烯烃乙烯基单体的共聚物、苯乙烯系均聚物及其共聚物。
在本发明烷氧胺为固体或在高于该聚合物加工温度的温度下熔体的情况下,在施用于聚合物基质之前,将这些研磨成平均粒度在100μm以下的细粉可能是有利的,因为观察到小粒度改进本发明组合物的阻燃性。
本发明还涉及如下组合物,其除如上所定义的组分a)和b)以外包括额外阻燃剂及其他选自所谓抗滴剂和聚合物稳定剂的添加剂作为任选的组分。
代表性含磷阻燃剂为例如:
四苯基间苯二酚二磷酸酯(RDP,Akzo Nobel),间苯二酚二磷酸酯低聚物(RDP)、磷酸三苯酯、磷酸三(2,4-二叔丁基苯基)酯、乙二胺二磷酸酯(EDAP)、多磷酸铵、N,N-二(2-羟乙基)胺甲基膦酸二乙基酯、磷酸羟烷基酯、二C1-C4烷基亚膦酸和连二磷酸(H3PO2)的盐(尤其是Ca2+、Zn2+或Al3+盐)、硫化四(羟甲基)三苯基膦、9,10-二氢-9-氧杂-10-磷酰基菲-10-氧化物(DOPO)的衍生物、磷腈阻燃剂和基于甲烷膦酸的聚碳酸酯。
含氮阻燃剂为例如异氰脲酸酯阻燃剂,例如聚异氰脲酸酯、异氰脲酸的酯或异氰脲酸盐。代表性实例为异氰脲酸羟烷基酯,如异氰脲酸三(2-羟乙基)酯、异氰脲酸三(羟甲基)酯、异氰脲酸三(3-羟基正丙基)酯或异氰脲酸三缩水甘油基酯。
含氮阻燃剂包括其他基于三聚氰胺的阻燃剂。代表性实例为三聚氰胺氰脲酸盐、三聚氰胺硼酸盐、三聚氰胺磷酸盐、三聚氰胺焦磷酸盐、三聚氰胺多磷酸盐、三聚氰胺多磷酸铵、三聚氰胺焦磷酸盐铵、二-三聚氰胺磷酸盐和二-三聚氰胺焦磷酸盐。
其他实例为:苯代胍胺、嘧啶如6-氨基尿嘧啶、异氰脲酸三(羟乙基)酯、尿囊素、甘脲、脲氰脲酸酯、多磷酸铵,选自蜜勒胺、蜜白胺、氰尿酰胺系列的三聚氰胺的缩合产物和/或高级缩合化合物或三聚氰胺与磷酸的反应产物或其混合物。
代表性有机卤素阻燃剂例如为多溴二苯醚(DE-60F,Great LakesCorp.)、十溴二苯醚(DBDPO,102E)、磷酸三[3-溴-2,2-二(溴甲基)丙基]酯(PBFMC Corp.)、磷酸三(2,3-二溴丙基)酯、磷酸三(2,3-二氯丙基)酯、氯菌酸、四氯邻苯二甲酸、四溴邻苯二甲酸、聚-β-氯乙基三膦酸酯混合物、四溴双酚A二(2,3-二溴丙醚)(PE68)、溴化环氧树脂、亚乙基-二(四溴邻苯二甲酰亚胺)(BT-93)、二(六氯环戊二烯并)环辛烷(Declorane)、氯化链烷烃、八溴二苯醚、六氯环戊二烯衍生物、1,2-二(三溴苯氧基)乙烷(FF680)、四溴双酚A(RB100)、亚乙基二(二溴降冰片烷二甲酰亚胺)(BN-451)、二(六氯环戊二烯并)环辛烷(bis-(hexachlorocycloentadeno)cyclooctane)、PTFE、三(2,3-二溴丙基)异氰脲酸酯和亚乙基-二-四溴邻苯二甲酰亚胺。
通常使上述有机卤素阻燃剂与无机氧化物增效剂组合。该用途的最常见的是锌或锑氧化物,如Sb2O3或Sb2O5。硼化合物也是合适的。
代表性无机阻燃剂包括例如氢氧化铝(ATH)、勃姆石(AlOOH)、氢氧化镁(MDH)、硼酸锌、CaCO3、(经有机改性的)层状硅酸盐(优选呈纳米尺寸形式)、(经有机改性的)层状双氢氧化物及其混合物。无机阻燃剂如ATH或MDH可经表面处理以改善其在聚合物基质中的分散。
上述额外阻燃剂类有利地以该有机聚合物基质的约0.5重量%至约60.0重量%;例如约1.0%至约40.0%;例如为该聚合物或基于组合物总重量为约5.0重量%至约35.0重量%的量含于本发明组合物中。
根据另一实施方案,本发明涉及额外包含所谓抗滴剂作为额外组分的组合物。
这些抗滴剂减小该热塑性聚合物的熔体流动性并在高温下抑制液滴形成。多个参考文献如美国专利说明书4,263,201描述将抗滴剂加入阻燃剂组合物。
在高温下抑制液滴形成的合适添加剂包括玻璃纤维、聚四氟乙烯(PTEE)、高温弹性体、碳纤维、玻璃球等。
加入不同结构的聚硅氧烷已于多个参考文献中提出:参照美国专利说明书6,660,787、6,727,302或6,730,720。
稳定剂优选不含卤素且选自硝酰基稳定剂、硝酮稳定剂、氧化胺稳定剂、苯并呋喃酮稳定剂、亚磷酸盐和亚膦酸盐稳定剂、醌甲基化物稳定剂和2,2'-亚烷基双酚的单丙烯酸酯稳定剂。
如上所述,本发明组合物可额外含有一种或多种常规添加剂,例如选自颜料、染料、增塑剂、抗氧化剂、触变剂、分散剂、流平助剂、基础共稳定剂、金属钝化剂、金属氧化物、有机磷化合物、其他光稳定剂及其混合物,尤其是颜料、酚类抗氧化剂、硬脂酸钙、硬脂酸锌、分散剂,2-羟基-二苯甲酮、2-(2'-羟苯基)苯并三唑和/或2-(2-羟苯基)-1,3,5-三嗪类UV吸收剂。
如上所定义的该组合物的优选额外添加剂为加工稳定剂如上述亚磷酸酯和酚类抗氧化剂,和光稳定剂如苯并三唑。优选的特定抗氧化剂包括3-(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯(IRGANOX 1076)、四[3-(3,5-二叔丁基-4-羟苯基)丙酸异戊四醇酯](IRGANOX 1010)、异氰脲酸三(3,5-二叔丁基-4-羟苯基)酯(IRGANOX 3114)、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟苯基)苯(IRGANOX 1330)、三乙二醇二[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯](IRGANOX 245)和N,N'-己烷-1,6-二基-二[3-(3,5-二叔丁基-4-羟苯基)丙酰胺](IRGANOX 1098)。特定的加工稳定剂包括三(2,4-二叔丁基苯基)亚磷酸酯(IRGAFOS 168)、3,9-二(2,4-二叔丁基苯氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷(IRGAFOS 126)、2,2',2″-次氮基[三乙基三(3,3',5,5'-四叔丁基-1,1'-联苯-2,2'-二基)]亚磷酸酯(IRGAFOS 12)和四(2,4-二叔丁基苯基)[1,1-联苯]-4,4'-二基二亚膦酸酯(IRGAFOS P-EPQ)。特定的光稳定剂包括2-(2H-苯并三唑-2-基)-4,6-二(1-甲基-1-苯基乙基)酚(TINUVIN 234)、2-(5-氯(2H)-苯并三唑-2-基)-4-(甲基)-6-(叔丁基)酚(TINUVIN 326)、2-(2H-苯并三唑-2-基)-4-(1,1,3,3-四甲基丁基)酚(TINUVIN 329)、2-(2H-苯并三唑-2-基)-4-(叔丁基)-6-(仲丁基)酚(TINUVIN350)、2,2'-亚甲基二(6-(2H-苯并三唑-2-基)-4-(1,1,3,3-四甲基丁基)酚)(TINUVIN 360)和2-(4,6-二苯基-1,3,5-三嗪-2-基)-5-[(己基)氧基]酚(TINUVIN 1577)、2-(2'-羟基-5'-甲基苯基)苯并三唑(TINUVIN P)、2-羟基-4-(辛氧基)二苯甲酮(CHIMASSORB 81)、1,3-二[(2'-氰基-3',3'-二苯基丙烯酰基)氧基]-2,2-二{[(2'-氰基-3',3'-二苯基丙烯酰基)氧基]甲基}丙烷(UVINUL 3030,BASF)、2-氰基-3,3-二苯基丙烯酸乙基酯(UVINUL 3035,BASF)和2-氰基-3,3-二苯基丙烯酸(2-乙基己基)酯(UVINUL 3039,BASF)。
其他优选的添加剂选自分散剂类。合适的聚合物分散剂由聚合物链和至少一个所谓的锚固基团构成。该聚合物链提供聚合物基质内的溶解性能和空间稳定性,并决定与该聚合物体系的相容性,而该锚固基团与阻燃剂分子本身连接。
合适的聚合物分散剂的特征为其湿润固体阻燃剂分子的效果,通过分散的阻燃剂颗粒防止粘度增加和防止该类颗粒再絮凝。
合适的聚合物分散剂基于例如苯乙烯-马来酸酐共聚物或经酸性基团取代的聚醚。
优选为以相对于组分b)的聚合物基质的重量为0.01-10.0%、尤其是0.05-5.0%的量包含上述添加剂。
通过已知方法如以粉末形式干混或以例如惰性溶剂、水或油中的溶液、分散体或悬浮液形式湿混,将上述组分掺入聚合物组分中。可在模塑之前或之后,或还可通过将溶解或分散的添加剂或添加剂混合物施用于该聚合物材料中(随后蒸发或不蒸发该溶剂或悬浮/分散剂),掺入添加剂组分a)和b)和任选的其他添加剂。可以干燥混合物或粉末或以溶液或分散体或悬浮液或熔体形式将它们直接加入加工装置(例如挤出机、内部混合机等)中。
可在常规混合机器中将添加剂组分加入该聚合物基质中,其中熔化该聚合物并使其与该添加剂混合。合适的机器对本领域熟练技术人员是已知的。它们主要为混合机、捏合机和挤出机。
该方法优选在挤出机中,通过在加工过程中引入添加剂来进行。
特别优选的加工机器为单螺杆挤出机、逆转和共转双螺杆挤出机、行星式齿轮挤出机、环状挤出机或共捏合机。具有至少一个气体除去室的加工机器可用于可施用真空。
合适的挤出机和捏合机描述于例如Handbuch der Kunststoffex-trusion,第1卷Grundlagen,编辑F.Hensen,W.Knappe,H.Potente,1989,3-7页,ISBN:3-446-14339-4(第2卷Extrusionsanlagen 1986,ISBN3-446-14329-7)中。
例如,该螺杆长度为螺杆直径的1-60倍,优选为螺杆直径的35-48倍。该螺杆的转动速度优选为10-600转/分钟(rpm),优选25-300rpm。
最大产量取决于螺杆直径、转动速度和驱动力。还可通过改变上述参数或使用称重器递送剂量,在低于最大处理量的水平下进行本发明方法。
若加入多种组分,则可预混或单独加入这些组分。
还可将该添加剂组分a)和任选的其他添加剂喷雾至该聚合物基质b)上。该添加剂混合物稀释其他添加剂如上述常规添加剂或其熔体,以使得它们可与这些添加剂一起喷雾至该聚合物基质上。
还可以母料(“浓缩物”)形式将添加剂组分a)和b)、任选的其他添加剂加入该聚合物,其含有掺于聚合物中的浓度为例如约1.0重量%至约60.0重量%,优选2.0重量%至约30.0重量%的组分。该聚合物的结构并不需要与最终加入添加剂的聚合物相同。在该类操作中,可使用呈粉末、颗粒、溶液和悬浮液的形式或呈乳胶形式的聚合物。
可在成型操作之前或期间进行掺混。含文中所述的本发明添加剂的材料优选用于生产模塑制品,例如滚塑成型制品、注塑制品、型材等,尤其是纤维、熔纺非织造物、薄膜或泡沫。
本发明的另一实施方案涉及如下化合物(I),其中磷原子为较低氧化态。在该类化合物(I)的定义中:
R为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1-R4为甲基;或
R1与R2中一个以及R3与R4中一个为甲基;且R1与R2中的另一个以及R3与R4中的另一个为乙基;
R5和R6相互独立地为氢或甲基;和
Z为以下部分式的基团:
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷基、C1-C4烷氧基、苯基或苯氧基;
Rc为氢或C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基、苯基或苯氧基,或一起为C2-C8亚烷二氧基;或
Z为以下部分式的基团:
其中Rc为氢或C1-C12烷基;或
Z为以下部分式的基团:
其中:
Rc'为C2-C8亚烷基;
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1′与R2′中一个以及R3′与R4′中一个为甲基;和R1′与R2′中的另一个以及R3′与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
Rd'和Re'相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Rd'和Re'一起为C2-C8亚烷二氧基。
这些化合物可用作制备其中Z为部分式(A)、(B)、(C)、(D)和(E)的基团的化合物(I)的中间体。通过本身已知的类似方法例如通过与氧化剂如H2O2反应进行这些中间体的转换。该方法阐述于以下实施例中。
以下实施例阐述本发明:
A)代表性化合物的合成
实施例1
1.1
在250ml磺化烧瓶中,在氮气氛围下,将8.67g(1)、4.22g三乙胺和0.10g4-二甲基氨基吡啶(DMAP)催化剂溶于50ml甲苯中。使该反应混合物冷却至0℃。加入25ml甲苯中的5.91g 2-氯-5,5-二甲基-1,3,2-二氧磷杂环己烷(可自Aldrich商业市购)的溶液,并将该反应温度在0-5℃下保持45分钟。在完成该加料后,在室温下搅拌该反应混合物16小时并过滤。用100ml水和100ml NaHCO3水溶液洗涤滤液。用100ml水洗涤该有机层两次。在硫酸钠上干燥该有机层,并真空除去溶剂,获得11.91g粘性黄色液体(2),在氮气氛围下,将其溶于30ml二氯甲烷并冷却至0℃。缓慢加入2.50g过氧化氢(50%)。搅拌该反应混合物过夜。通过加入20%焦亚硫酸钠水溶液分解任何过量的过氧化氢。用100ml水洗涤该有机层并在硫酸钠上干燥。真空除去溶剂后,获得9.41g橙色固体(3)(m.p.:120-123℃)。
1H-NMR(300MHz,CDCl3):δ4.3(2H),3.6-3.8(4H),2.7-2.9(3H),1.79(2H),1.5-1.3(4H),1.25(6H),1.2(12H),0.6-0.9(6H);
IR(纯物质):vmax2968,2940,1467,1360,1210,1051,1035,1005,960,821[cm-1];
MS(m/z):405.2[M+H]+。
1.2
以类似于实施例2.2的方式,由150.0g 1-乙氧基-4-氧代-2,2,6,6-四甲基哌啶(可根据WO 2008/003602获得)制备171.19g原料(1)。
实施例2
2.1
以类似于实施例1的方式,由8.09g(1)制备10.06g(2)。
1H-NMR(300MHz,CDCl3):δ3.9-3.6(4H),3.6(3H),2.9-3.1(3H),1.79(2H),1.6-1.3(4H),1.25(8H),1.2(9H),0.9(3H),0.7(3H);
IR(纯物质):vmax2954,2870,1468,1360,1209,1173,1050,999,742[cm-1];MS(m/z):391[M+H]+。
2.2
如下制备原料(1):
在氮气氛围下,将150.0g 1-甲氧基-4-氧代-2,2,6,6-四甲基哌啶(可根据WO 2008/003602获得)与100ml甲醇一起加入2000ml钢制高压釜中。将65.1g正丁胺与0.5g10%碳载Pd一起加入相同反应器中。通过施加8-10kg的氢气压力,在100℃下搅拌该反应混合物20-24小时。用13C-NMR-光谱法监测该反应。在>C=O基团在该13C-NMR光谱中消失后,使该反应混合物冷却至室温。通过将该反应混合物滤过床除去该催化剂。真空除去溶剂后,以橙棕色液体获得178.08g(产率95%)产物。该产物可无需进一步纯化而用于下一步骤(2.1)中(MS(m/z):243[M+H])。
实施例3
3.1
以类似于实施例1的方式,由8.6g(1)制备且以黄色固体得到5.4g(2)。
1H-NMR(300MHz,CDCl3):δ4.3(4H),3.6-3.8(8H),2.9-3.1(6H),2.6(H),1.79(4H),1.5-1.3(14H),1.25(15H),1.24(15H),0.7-0.9(6H);
IR(纯物质):vmax3415,2973,1472,1362,1210,1056,1041,1006,948,814[cm-1];
MS(m/z):779.86[M+H]+。
3.2
原料的制备如下:
以类似于实施例2.2的方式,由165.1g 1-乙氧基-4-氧代-2,2,6,6-四甲基哌啶和40.82g 1,6-二氨基己烷制备165.1g原料(1)。
MS(m/z):483[M+H]+。
实施例4
4.1
以类似于实施例1的方式,由7.5g(1)制备且以白色固体得到5.6g(2)。
1H-NMR(300MHz,CDCl3):δ4.3(4H),3.7-3.9(4H),3.5(6H),3.0(6H),1.79(4H),1.5-1.3(14H),1.25(15H),1.24(15H),0.7-0.9(6H);
IR(纯物质):vmax3429,2967,1469,1361,1212,1052,1034,1003,813[cm-1];MS(m/z):751[M+H]+。
4.2
原料的制备如下:
以类似于实施例2.2的方式,由150.0g 1-甲氧基-4-氧代-2,2,6,6-四甲基哌啶制备172.84g原料(1)。MS(m/z):455[M+H]+。
实施例5
5.1
在100ml磺化烧瓶中,在氮气氛围下,将106.0g(1)溶于50ml二氯甲烷中并冷却至0℃。加入10ml二氯甲烷中的3.0g二氯磷酸苯酯的溶液,并将温度在0℃-5℃下保持60分钟。在完成该加料后,在0℃-5℃下搅拌该反应混合物1小时并在室温下搅拌12小时。用TCL监测该反应进程。将50ml水加入该反应混合物中并分离各层。用水彻底洗涤该有机层并在硫酸钠上干燥。真空除去溶剂后,获得4.76g橙色树脂状产物。用以乙酸乙酯/甲醇(9.5:0.5)作为流动相的柱层析纯化该产物。获得2.57g流光色固体化合物。
1H-NMR(300MHz,CDCl3):δ7.2-7.4(5H),3.61(6H),2.6(2H),1.8-1.0(32H);
IR(纯物质):vmax3202,2974,2930,1593,1491,1452,1360,1198,1036,918,761[cm-1];
MS(m/z):511[M+H]+。
5.2
以类似于实施例7.2的方式,由1-甲氧基-4-氧代-2,2,6,6-四甲基哌啶制备并以褐色液体得到原料(1)。MS(Cl):187(MH+)。
实施例6
6.1
以类似于实施例5的方式,由7.5g(1)制备并以白色固体得到5.6g(2)。
1H-NMR(300MHz,CDCl3):δ7.2-7.4(5H),3.7(4H),2.6(2H),1.8-1.0(38H);IR(纯物质):νmax3155,2973,2930,1492,1454,1199,1039,920,762[cm-1];MS(m/z):539.3[M+H]+。
6.2
以类似于实施例7.2的方式,由1-乙氧基-4-氧代-2,2,6,6-四甲基哌啶制备,并以褐色液体获得该原料(1)。
MS(Cl):201(MH+)。
实施例7
7.1
以类似于实施例5的方式,由12.19g(1)和二氯磷酸苯酯制备并以白色固体获得6.2g(2)。
1H-NMR(300MHz,CDCl3):δ7.2-7.4(5H),3.7(2H),3.3(H),2.6(2H),1.79(2H),1.5-1.3(2H),1.25(6H),1.2(6H),0.9(3H);
IR(纯物质):vmax3268,3151,2971,2935,1488,1457,1199,1095,920,760[cm-1];
MS(m/z):567.4[M+H]+。
7.2
原料(1)的制备如下:
在250ml甲醇氨溶液(0.2g/ml)的存在下,在100℃/10.0巴下,用500ml甲醇中的5.0g阮内钴催化剂使50.0g(0.234mol)1-丙氧基-2,2,6,6-四甲基哌啶-4-酮氢化2小时。过滤后,在50℃/50毫巴下蒸发溶液并在50℃/0.2毫巴下干燥。在无进一步纯化下,以产量为41.0g(81.8%,纯度>90.5%)获得澄清黄色液体。
MS(CI):215(MH+)。
实施例8
以类似于实施例5的方式,由4.88g(1)和5.5g二苯基膦酰氯制备并以白色固体获得4.68g(2)。该反应在甲苯中进行并使用三乙胺作为酸清除剂。
1H-NMR(300MHz,CDCl3):δ7.2-7.4(10H),3.7(2H),3.3(1H),2.6(2H),1.79(2H),1.5-1.3(2H),1.25(6H),1.2(6H),0.9(3H);
IR(纯物质):vmax3147,2972,1438,1359,1194,1184,1046,961,834,725[cm-1];
MS(m/z):415.2[M+H]+。
实施例9
以类似于实施例5的方式,由3.86g(1)和5.5g二苯基膦酰氯制备并以白色固体得到3.73g(2)。
1H-NMR(300MHz,CDCl3):δ7.2-7.4(10H),3.6(3H),3.4(1H),2.6(2H),1.9(2H),1.2(6H),0.8(6H);
IR(纯物质):vmax3170,2970,1436,1359,1195,1183,1035,964,832,723[cm-1];
MS(m/z):387.4[M+H]+。
实施例10
以类似于实施例5的方式,由5.31g(1)和5.5g二苯基膦酰氯制备且以橙色固体得到6.15g(2)。
1H-NMR(300MHz,CDCl3):δ7.4-7.9(10H),3.7(2H),3.4(H),2.8-3.0(2H),2.6(2H),1.79(2H),1.5-1.3(4H),1.25(6H),1.2(6H),0.7-0.9(6H);
IR(纯物质):vmax2974,2887,1467,1438,1373,1209,1193,1117,924,722[cm-1];
MS(m/z):457[M+H]+。
实施例11
以类似于实施例5的方式,由5.02g(1)和5.5g二苯基膦酰氯制备并以白色固体得到6.85g(2)。
1H-NMR(300MHz,CDCl3):δ7.4-7.9(10H),3.6(3H),3.4(H),2.8-3.0(2H),1.79(2H),1.5-1.3(6H),1.25(6H),1.2(6H),0.7-0.9(3H);
IR(纯物质):vmax2974,2887,1467,1438,1373,1209,1193,1117,924,722[cm-1];
MS(m/z):443.41[M+H]+。
实施例12
以类似于实施例5的方式,由7.35g(1)和9.0g二苯基膦酰氯制备并以粘性液体获得8.93g(2)。(1)的制备描述于WO 2008/003602的实施例17中。
1H-NMR(300MHz,CDCl3):δ7.4-7.9(10H),4.6(1H),3.7(2H),1.6-1.9(4H),1.1-1.3(6H),0.9-1.1(9H);
IR(纯物质):vmax3147,2972,1438,1359,1194,1184,1046,961,834,725[cm-1];
MS(m/z):402[M+H]+。
实施例13
以类似于实施例5的方式,由1.94g(1)和9.0g二苯基膦酰氯制备并以粘性液体获得3.50g(2)。(1)的制备描述于WO 2008/003602的实施例15中。
1H-NMR(300MHz,CDCl3):δ7.4-7.9(10H),4.6(1H),3.6(3H),1.6-1.9(4H),1.2-1.3(6H),0.9-1.1(6H);
IR(纯物质):vmax3255,2988,1441,1361,1258,1114,1046,1013,963,817,730[cm-1];
MS(m/z):388[M+H]+。
实施例14
在氩气氛围下,将3.58g(1)、4.96g磷酸二乙酯和1.31g叔丁胺加入三颈圆底烧瓶中。在室温下搅拌该反应混合物24小时。通过过滤分离出白色固体(2)。用己烷洗涤该产物并在50℃的烘箱中干燥8小时。(1)的制备描述于WO 2008/003602的实施例28中。
1H-NMR(300MHz,CDCl3):δ4.1-4.3(4H),3.7-3.9(2H),1.8-2.0(4H),1.25(12H),1.2(9H);
IR(纯物质):vmax3274,2975,2924,1357,1232,1175,1038,1022,964[cm-1];MS(m/z):338[M+H]+。
实施例15
以类似于实施例14的方式,由3.83g(1)和9.0g亚磷酸二乙酯制备3.75g(2)。(1)的制备描述于WO 2008/003602的实施例29中。
1H NMR(300MHz,CDCl3):δ4.1-4.3(4H),3.7-3.9(2H),1.8-2.0(6H),1.3-1.5(12H),1.25(6H),0.8(3H);
IR(纯物质):vmax3276,2971,2879,1466,1370,1228,1056,1028,949,799[cm-1];
MS(m/z):352[M+H]+。
实施例16
以类似于实施例15的方式,由5.0g(1)和6.6g亚磷酸二乙酯制备并以白色固体获得3.44g(2)。(1)的制备描述于WO 2008/003602的实施例30中。
1H NMR(300MHz,CDCl3):δ4.1-4.3(4H),3.6(3H),1.8-2.0(4H),1.3-1.5(12H),1.25(6H);
IR(纯物质):vmax3276,2971,2879,1466,1370,1228,1056,1028,949,799[cm-1];
MS(m/z):324.31[M+H]+。
实施例17
以类似于实施例15的方式,由4.96g(1)和6.6g亚磷酸二乙酯制备并以白色固体获得1.92g(2)。(1)的制备描述于WO 2008/003602的实施例60中。
1H NMR(300MHz,CDCl3):δ4.1-4.3(4H),3.7-3.9(2H),1.8-2.0(4H),1.5-1.7(12H),1.2-1.4(18H),0.8(3H);
IR(纯物质):vmax3290,2977,2931,1470,1358,1230,1175,1053,1025,953,725[cm-1];
MS(m/z):352[M+H]+。
实施例18
18.1
将5.56g 4-N-(正丁基)氨基-1-丙氧基-2,2,6,6-四甲基哌啶(1)溶于70ml甲苯中。加入1.85g低聚甲醛和4.44g 9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(CAS登记号35948-25-5;可由TCI Europe或ABCR市购)。使该反应混合物在80℃下加热24小时。用100ml MTBE稀释该混合物,用水洗涤3次并在硫酸钠上干燥。真空除去溶剂。在硅胶(己烷/乙酸乙酯2:1)上过滤该粗产物并获得8.16g浅黄色泡沫。
1H-NMR(300MHz):7.87(3H),7.60(1H),7.41(1H),7.35(1H),7.12(2H),3.61(1H)3.53(2H),2.62(2H),2.30(2H),1.41(4H),1.20-0.8(24H);MS(M+H)+:499。
18.2
以类似于实施例2.2的方式由1-丙氧基-4-氧代-四甲基哌啶制备原料(1)。
实施例19
在氩气氛围下,将5.17g(2)、11.45g(1)、3.20g过氧化二苯甲酰和20ml二烷加入250ml磺化烧瓶中。使该反应混合物在85℃下加热48小时。通过TCL监测该反应过程。将该反应混合物冷却至室温并用20%亚硫酸钠水溶液洗涤。将所形成的聚集物溶于100ml乙酸乙酯中。用水彻底洗涤该有机层并最终在硫酸钠上干燥。真空除去溶剂后,获得6.09g白色固体(MP198℃dec.)。
1H NMR(300MHz,CDCl3):δ3.61(3H),2.3(2H),1.4-1.9(8H),0.8-1.3(24H),0.75(3H);
IR(纯物质):vmax 2975,2926,1729,1468,1451,1361,1242,1160,1037,955,714[cm-1];
MS(m/z):421[M+H]+。
B)应用实施例
材料与方法
在Tmax:230℃下,在共转双螺杆挤出机(ZSK25,Coperion Werner &Pfleiderer)中挤出市售聚丙烯(HF500N,Basell)(加热区域1-6,产率4kg/h和100rpm),并加入基础浓度的稳定剂[0.3%IRGANOXB225(IRGAFOS 168与IRGANOX 1010的1:1混合物)]、0.05%硬脂酸钙和列于表1中的阻燃添加剂。在水中冷却后,使该聚合物线材造粒。
通过在热压机中压缩模塑(薄膜厚度200μm,250×110mm,FontineTP200,pmax 50kN,230℃)或通过注塑(100×100mm平板,厚度:1mm,Arburg 370S,225℃)制备试样。
根据DIN 4102-B2中所述的方法(40mm燃烧长度,由挤出(ZSK 18,190℃)颗粒和随后压缩模塑(230℃)获得的200μm PP薄膜),测试该试样的阻燃性。
表示燃烧长度和时间的低值为增加的阻燃性效力。
结果
表
表(续)
Claims (12)
1.一种下式化合物:
其中:
R为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1-R4为甲基;或
R1与R2中一个以及R3与R4中一个为甲基;且R1与R2中的另一个以及
R3与R4中的另一个为乙基;
R5和R6相互独立地为氢或甲基;和
Z为如下部分式的基团:
其中:
Ra与Rb相互独立地为C1-C4烷基或C1-C4烷氧基;
Rc为氢或C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基、苯基或苯氧基,或一起为C2-C8亚烷二氧基;或
Z为如下部分式的基团:
其中:
Rc为氢或C1-C12烷基;或
Z为如下部分式的基团:
其中:
Rc'为C2-C8亚烷基;
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1'与R2'中一个以及R3'与R4'中一个为甲基;且R1'与R2'中的另一个以及R3'与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
Rd'和Re'相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为如下部分式的基团:
其中:
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1'与R2′中一个以及R3'与R4′中一个为甲基;且R1'与R2′中的另一个以及
R3'与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
R7为苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基或(C1-C4烷基)1-3苯基-C1-C4烷基。
2.一种式(I)化合物,其中:
R为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1-R4为甲基;或
R1与R2中一个以及R3与R4中一个为甲基;且R1与R2中的另一个以及
R3与R4中的另一个为乙基;
R5和R6相互独立地为氢或甲基;和
Z为如下部分式的基团:
其中:
Ra与Ra'和Rb与Rb'相互独立地为C1-C4烷基、C1-C4烷氧基、苯基或苯氧基;
Rc为氢或C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Z为如下部分式的基团:
其中Rc为氢或C1-C12烷基;或
Z为如下部分式的基团:
其中:
Rc'为C2-C8亚烷基;
R'为氢或选自C1-C12烷基、羟基-C2-C12烷基、二羟基-C3-C12烷基、苯基、苯基-C1-C4烷基、(C1-C4烷基)1-3苯基、(C1-C4烷基)1-3苯基-C1-C4烷基、(C1-C4烷氧基)1-3苯基、(C1-C4烷氧基)1-3苯基-C1-C4烷基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、-C(=O)-H、-C(=O)-C1-C19烷基和苯甲酰基的取代基;
R1'-R4'为甲基;或
R1′与R2′中一个以及R3'与R4′中一个为甲基;且R1'与R2′中的另一个以及
R3'与R4′中的另一个为乙基;
R5'和R6'相互独立地为氢或甲基;和
Rd'和Re'相互独立地为C1-C4烷氧基、苯基或苯氧基;或
Rd'和Re'一起为C2-C8亚烷二氧基。
3.根据权利要求1的化合物(I),其中:
R为氢或C1-C12烷基;
R1-R4为甲基;
R5和R6为氢;和
Z如权利要求1所定义。
4.根据权利要求1的化合物(I),其中:
R为氢或C1-C12烷基;
R1-R4为甲基;
R5和R6为氢;和
Z为部分式(A)或(C)的基团,
其中:
Ra与Rb相互独立地为C1-C4烷氧基;
Rc为C1-C12烷基;和
Rd和Re相互独立地为C1-C4烷氧基或苯基;或
Z为部分式(D)的基团,
其中:
Rc为C1-C12烷基;或
Z为部分式(E)的基团,
其中:
Rc'为C2-C8亚烷基;
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为氢;和
Rd'和Re'相互独立地为C1-C4烷氧基或苯基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为部分式(F)的基团,
其中:
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为甲基;和
R7为苯基。
5.根据权利要求1的化合物(I),其中:
R为C1-C8烷基;
R1-R4为甲基;
R5和R6为氢;和
Z为部分式(A)或(C)的基团,
其中:
Ra与Rb为C1-C4烷氧基;
Rc为C1-C6烷基;和
Rd和Re相互独立地为C1-C4烷氧基或苯基;或一起为C2-C8亚烷二氧基;
或
Z为部分式(D)的基团,
其中:
Rc为C1-C8烷基;或
Z为部分式(E)的基团,
其中:
Rc'为C2-C8亚烷基;
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为氢;和
Rd'和Re'相互独立地为C1-C4烷氧基或苯基;或
Rd'和Re'一起为C2-C8亚烷二氧基;或
Z为部分式(F)的基团,
其中:
R'为C1-C12烷基;
R1'-R4'为甲基;
R5'和R6'为甲基;和
R7为苯基。
10.一种组合物,包括:
a)化合物(I),其中R、R1-R6和Z如权利要求1所定义;和
b)聚合物基质。
11.根据权利要求10的组合物,其额外包括选自聚合物稳定剂、分散剂或额外阻燃剂的其他添加剂。
12.一种赋予聚合物基质以阻燃性的方法,所述方法包括将其中R、R1-R6和Z如权利要求1所定义的化合物(I)加入聚合物基质中。
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PCT/EP2011/050368 WO2011086114A1 (en) | 2010-01-15 | 2011-01-13 | Phospho-substituted alkoxyamine compounds |
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EP (1) | EP2523964A1 (zh) |
JP (1) | JP5631414B2 (zh) |
KR (1) | KR101434074B1 (zh) |
CN (1) | CN102712668A (zh) |
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WO (1) | WO2011086114A1 (zh) |
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CN110922637A (zh) * | 2019-11-13 | 2020-03-27 | 上海力道新材料科技股份有限公司 | 一种dopo衍生物阻燃光热稳定剂及其制备方法和应用 |
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CN106916183A (zh) * | 2017-03-07 | 2017-07-04 | 青岛科技大学 | 亚磷酸三(1‑烷氧基‑4‑羟基‑2,2,6,6‑四甲基哌啶醇)酯及其制备方法 |
CN106977547A (zh) * | 2017-04-27 | 2017-07-25 | 青岛科技大学 | 亚磷酸三(1‑环己氧基‑4‑羟基‑2,2,6,6‑四甲基哌啶醇)酯的提纯方法 |
CN106977547B (zh) * | 2017-04-27 | 2019-06-21 | 青岛科技大学 | 亚磷酸三(1-环己氧基-4-羟基-2,2,6,6-四甲基哌啶醇)酯的提纯方法 |
CN110922637A (zh) * | 2019-11-13 | 2020-03-27 | 上海力道新材料科技股份有限公司 | 一种dopo衍生物阻燃光热稳定剂及其制备方法和应用 |
CN110922637B (zh) * | 2019-11-13 | 2021-10-26 | 上海力道新材料科技股份有限公司 | 一种dopo衍生物阻燃光热稳定剂及其制备方法和应用 |
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US20130059952A1 (en) | 2013-03-07 |
TW201139630A (en) | 2011-11-16 |
JP5631414B2 (ja) | 2014-11-26 |
KR20120123091A (ko) | 2012-11-07 |
EP2523964A1 (en) | 2012-11-21 |
WO2011086114A1 (en) | 2011-07-21 |
KR101434074B1 (ko) | 2014-08-25 |
JP2013517248A (ja) | 2013-05-16 |
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