CN1950436B - 阻燃剂 - Google Patents
阻燃剂 Download PDFInfo
- Publication number
- CN1950436B CN1950436B CN2005800148347A CN200580014834A CN1950436B CN 1950436 B CN1950436 B CN 1950436B CN 2005800148347 A CN2005800148347 A CN 2005800148347A CN 200580014834 A CN200580014834 A CN 200580014834A CN 1950436 B CN1950436 B CN 1950436B
- Authority
- CN
- China
- Prior art keywords
- trimeric cyanamide
- alkyl
- fire retardant
- acid
- phenyl
- 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 69
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 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 24
- 229920001059 synthetic polymer Polymers 0.000 claims abstract description 17
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical class 0.000 claims abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- -1 isobutyl- Chemical group 0.000 claims description 154
- 239000000203 mixture Substances 0.000 claims description 61
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 34
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 30
- 239000007859 condensation product Substances 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 150000001408 amides Chemical class 0.000 claims description 23
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 16
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 16
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229920000388 Polyphosphate Polymers 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000001205 polyphosphate Substances 0.000 claims description 12
- 235000011176 polyphosphates Nutrition 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 229920005669 high impact polystyrene Polymers 0.000 claims description 10
- 239000004797 high-impact polystyrene Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 9
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 9
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 7
- DORQGZNYICOAAZ-UHFFFAOYSA-N azane cyanamide Chemical compound N.NC#N DORQGZNYICOAAZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- 239000012745 toughening agent Substances 0.000 claims description 6
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 5
- 150000001463 antimony compounds Chemical class 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052725 zinc Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- 229920007019 PC/ABS Polymers 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000004411 aluminium Chemical group 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 230000003068 static effect Effects 0.000 claims description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical group NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- IUTYMBRQELGIRS-UHFFFAOYSA-N boric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.NC1=NC(N)=NC(N)=N1 IUTYMBRQELGIRS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000002114 nanocomposite Substances 0.000 claims description 3
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical class N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 229910021331 inorganic silicon compound Inorganic materials 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- 229920005668 polycarbonate resin Polymers 0.000 claims 1
- 239000004431 polycarbonate resin Substances 0.000 claims 1
- 229920001225 polyester resin Polymers 0.000 claims 1
- 239000004645 polyester resin Substances 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract description 4
- 150000002830 nitrogen compounds Chemical class 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000000126 substance Substances 0.000 description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
- 239000005977 Ethylene Substances 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 11
- 229920002292 Nylon 6 Polymers 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000012964 benzotriazole Substances 0.000 description 9
- 229920001903 high density polyethylene Polymers 0.000 description 9
- 239000004700 high-density polyethylene Substances 0.000 description 9
- 229920001707 polybutylene terephthalate Polymers 0.000 description 9
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229920002302 Nylon 6,6 Polymers 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 7
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical compound C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 4
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 4
- DKHJONPHCWFBAX-UHFFFAOYSA-N 3-butyl-3h-1-benzofuran-2-one Chemical group C1=CC=C2C(CCCC)C(=O)OC2=C1 DKHJONPHCWFBAX-UHFFFAOYSA-N 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- 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 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 150000003016 phosphoric acids Chemical class 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
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- 229960000969 phenyl salicylate Drugs 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- WOFYQUJNULCFLN-UHFFFAOYSA-N saytex bn 451 Chemical compound BrC1C(Br)C2CC1C(C1=O)C2C(=O)N1CCN(C1=O)C(=O)C2C1C1CC2C(Br)C1Br WOFYQUJNULCFLN-UHFFFAOYSA-N 0.000 description 1
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- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical class 0.000 description 1
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- 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
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- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 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
- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-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
- 229960004418 trolamine Drugs 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
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- 150000003672 ureas Chemical class 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
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- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 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
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- 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
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
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- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
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- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
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Abstract
本发明描述了一种阻燃剂,其包含A.至少一种式(I)的有机膦酸盐,其中R是氢、C1-C20烷基、未取代的或被C1-C4烷基取代的苯基或萘基,R’是氢、C1-C20烷基、未取代的或被C1-C4烷基取代的苯基或萘基或M1 r+/r,n是0-6的整数,M1 r+是r价金属离子或铵离子,r是1-4的整数,R13是异丙基、异丁基、叔丁基、环己基或者是被1-3个C1-C4烷基取代的环烷基,R14是氢、C1-C4烷基、环烷基或者是被1-3个C1-C4烷基取代的环己基,及R15是氢、C1-C18烷基、三甲基甲硅烷基、苄基、苯基或磺酰基;和B.至少一种基于氮化合物的阻燃剂组分,并且还涉及其在合成聚合物中的用途。
Description
本发明涉及一种新型的阻燃剂组合物及其在合成聚合物,特别是热塑性聚合物中的用途。
膦酸金属盐单独或与其它组分一起已知作为许多热塑性聚合物的阻燃剂,例如GB-A-2211850、EP-A-245207、EP-A-343109和DE-A-3833977中的聚合物,其中特别重要的是甲基膦酸甲酯的盐。
含氮的阻燃剂,特别是基于三聚氰胺的那些,很早就是已知的了,并且某些情况下它们可以商购得到。一些三聚氰胺衍生物还含有磷。涉及这些阻燃剂的公开实例有EP-A-782599、EP-A-1095030、US-A-4010137和US-A-3915777。
含氮的阻燃剂与基于磷化合物的阻燃剂的结合同样是已知的。在这方面,参见例如DE-A-19734437、DE-A-19737727、WO-A-97/39053、EP-A-1070754、EP-A-6568和DE-A-19614424。特殊的磷酸盐或膦酸盐与含氮化合物的结合同样已知作为阻燃剂,例如可见于EP-A-484832、EP-A-545496、EP-A-707036、WO-A-01/98401、GB-A-1468188和EP-A-617079。
仍旧需要具有改善的性能并且可以用于各种塑料的阻燃剂。特别地,随着对安全和环境的要求的不断提高,目前已知的阻燃剂已不能满足所有的要求。
现已发现,含氮的阻燃剂特别是基于三聚氰胺的那些与非常特别的有机膦酸盐的结合使用在许多聚合物中产生了显著的作用。
因此,本发明涉及一种阻燃剂,其包含
A.至少一种式I的有机膦酸盐
其中R是氢、C1-C20烷基、未取代的或被C1-C4烷基取代的苯基或萘基,R’是氢、C1-C20烷基、未取代的或被C1-C4烷基取代的苯基或萘基或M1 r+/r,n是0-6的整数,M1 r+是r价金属离子或铵离子,r是1-4的整数,
R13是异丙基、异丁基、叔丁基、环己基或者是被1-3个C1-C4烷基取代的环烷基,
R14是氢、C1-C4烷基、环烷基或者是被1-3个C1-C4烷基取代的环己基,及
R15是氢、C1-C18烷基、三甲基甲硅烷基、苄基、苯基或磺酰基;和
B.至少一种基于氮化合物的阻燃剂组分。
组分B是,例如式III-VIIIa的氮化合物或由这些式表示的化合物的混合物,
其中R4-R6各自彼此独立地是氢、C1-C8烷基、C5-C6环烷基或C1-C4烷基-C5-C6环烷基,它们各自是未取代的或被羟基或C1-C4-羟基烷基取代、C2-C8链烯基;C1-C8烷氧基、-酰基、-酰氧基、C6-C12芳基、-O-R2或-N(R2)R3,以及R2和R3是氢、C1-C4烷基、C5-C6环烷基、C2-C8链烯基、C1-C4羟基烷基或C6-C12芳基,条件是R4-R6不同时是氢,以及在式III中不同时是-NH2,以及在式VII中至少存在一个能够加上一个质子的基团,
R7-R11各自彼此独立地具有与R4-R6相同的可能含义,但是-N(R2)R3除外,X是质子酸的阴离子,x是从后者转移到三嗪化合物上的质子的数目,y是从质子酸中夺取的质子的数目;
或多磷酸铵、三聚氰胺磷酸铵、三聚氰胺多磷酸铵、三聚氰胺焦磷酸铵、三聚氰胺的缩合产物或/和三聚氰胺与磷酸的反应产物或/和三聚氰胺的缩合产物与磷酸的反应产物或它们的混合物。
在式I中,烷基R和R’含有例如1-18个,特别是1-12个,优选是1-8或2-8个,更特别优选是2-4个碳原子。它们的个例是甲基、乙基、丙基、丁基、戊基、己基、辛基、十二烷基和硬脂基,其包括直链和支化的异构体。
当苯基或萘基被取代时,它们含有优选1-3,特别是1或2个C1-C4烷基。这种被取代的芳基的例子是邻-、间-或对-甲基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2-甲基-6-乙基苯基、4-叔丁基苯基、2-乙基苯基、2,6-二乙基苯基、1-甲基萘基、2-甲基萘基、4-甲基萘基和4-叔丁基萘基。
被1-3个C1-C4烷基取代的环烷基具有优选1或2个这样的烷基,其可以是直链或支化的。它们的例子是甲基环己基、二甲基环己基、三甲基环己基和叔丁基环己基。
在式I中,n是,例如1-6,优选1-4,特别是1或2,更特别是1。
r优选是1-3,特别是1或2。
取代基R和R’优选是氢以外的取代基。
在式I的化合物中,R优选是C1-C8烷基,例如C2-至C8-烷基,特别是C2-C4烷基。特别优选乙基。
有利的式I的化合物含有C1-C8烷基(特别是C2-C8烷基,更特别是C2-C4烷基,优选乙基)或选自于Na+、K+、Mg++/2、Ca++/2、Ba++/2、Zn++/2、B+++/3、Al+++/3、Cu++/2、Fe+++/3、Sn4+/4或Sb4+/4的阳离子,例如Na+、K+、Mg++/2、Ca++/2、Ba++/2、Zn++/2或Al+++/3,特别优选Ca++/2,作为取代基R’。
R’特别是C2-C4烷基或Na+、K+、Mg++/2、Ca++/2、Ba++/2、Zn++/2或Al+++/3,更特别是乙基或Ca++/2。
R13特别是叔丁基,R14是氢或C1-C4烷基并且R15是氢。R14还优选为叔丁基。
式I的化合物也是已知的,其在某些情况下可商购得到,或/和可以通过本身已知的方法制备。在这些方面,参见例如US-A-3,367,870、US-A-3,281,505、US-A-3,280,070、US-A-4,778,840。
式VII中的符号X例如表示磷酸、多磷酸(线性或分枝的)、焦磷酸、次膦酸、膦酸或硼酸的阴离子。
R4-R6例如各自彼此独立地是氢、C1-C4烷基、环戊基、环己基、甲基环己基、C1-C4羟基烷基、C2-C6链烯基、C1-C4烷氧基、未取代的或被1-3个甲基或甲氧基或/和卤原子、-OR2或-NR2R3取代的苯基,其中R2和R3各自彼此独立地是氢、C1-C4烷基、C1-C4羟基烷基、环烷基、甲基环己基或未取代的或被1-3个甲基或甲氧基或/和卤原子取代的苯基。在式III中,优选R2和R3中的至少一个不是氢。
R4-R6的优选范围,同样适用于R7-R11。
作为组分B,有利地使用的是式IV、V、VI、VII、VIII和VIIIa的化合物以及具体提及的三聚氰胺化合物,特别是式VII、VIIIa的化合物以及具体提及的三聚氰胺化合物。
优选的氮化合物(组分B)例如是苯代三聚氰二胺(式III,R4=苯基,R5=R6=-NH2)、三(羟乙基)异氰脲酸酯(式IV,R7=R8=R9=-CH2-CH2-OH)、尿囊素(式V,R7=R8=R9=R10=R11=H)、甘脲(式VI,R7=R8=R9=R10=H)以及三聚氰胺磷酸盐、二-三聚氰胺磷酸盐和三聚氰胺焦磷酸盐、三聚氰胺多磷酸盐、三聚氰胺硼酸盐(都是式VII型)、脲氰尿酸酯(式VIII型)、三聚氰胺氰尿酸酯(式VIIIa型)以及蜜白胺或蜜勒胺磷酸盐、蜜白胺或蜜勒胺多磷酸盐、多磷酸铵、三聚氰胺磷酸铵、三聚氰胺焦磷酸铵或三聚氰胺多磷酸铵。
用作组分B的化合物是已知的或者可以通过已知的常规方法得到。它们中的一些可以商购得到。
对于本发明的阻燃剂,应强调的是其中,组分B是至少一种式VII或/和VIIIa的化合物或/和多磷酸铵、三聚氰胺多磷酸铵、三聚氰胺焦磷酸铵、三聚氰胺的缩合产物或/和三聚氰胺与磷酸的反应产物或/和三聚氰胺的缩合产物与磷酸的反应产物或/和它们的混合物。
有利地,阻燃剂中的组分B是苯代三聚氰二胺、三(羟乙基)异氰脲酸酯、尿囊素、甘脲、三聚氰胺氰尿酸酯、三聚氰胺磷酸盐、二-三聚氰胺磷酸盐、三聚氰胺焦磷酸盐、脲氰尿酸酯、多磷酸铵、三聚氰胺多磷酸盐、三聚氰胺硼酸盐、三聚氰胺多磷酸铵或三聚氰胺焦磷酸铵,优选是来自蜜勒胺、蜜白胺、氰尿酰胺和/或更高级的缩合化合物系列的三聚氰胺的缩合产物,或三聚氰胺与磷酸的反应产物,和/或三聚氰胺的缩合产物与磷酸的反应产物或它们的混合物。
特别强调的是:二-三聚氰胺焦磷酸盐、三聚氰胺多磷酸盐、蜜勒胺多磷酸盐、蜜白胺多磷酸盐、和/或该类型的混合聚合盐,更特别是三聚氰胺多磷酸盐。
组分A和B的比例可以在很宽的范围内变化,并且取决于指定的用途。A∶B的比例(重量比)例如是5∶95-95∶5,例如是10∶90-90∶10,优选是20∶80-80∶20,特别是30∶70-70∶30以及40∶60-60∶40。
组分A和组分B都可以包含一种或多种式I或式III-VIIIa的化合物或上述具体提及的三聚氰胺化合物,并且不同式的化合物的混合物也是可以的。
本发明的阻燃剂非常适合将阻燃性能赋予合成聚合物特别是热塑性塑料。
这样的合成聚合物的例子是:
1.单-和二-烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁烯-1、聚-4-甲基戊烯-1、聚乙烯基环己烷、聚异戊二烯或聚丁二烯以及环烯的聚合产物,例如环戊烯或降冰片烯的聚合产物;以及聚乙烯(其可以任选是交联的),例如高密度聚乙烯(HDPE)、高分子量的高密度聚乙烯(HDPE-HMW)、超高分子量的高密度聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)以及线性低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
在前面段落中作为例子提及的聚烯烃,也就是单-烯烃的聚合物,特别是聚乙烯和聚丙烯,可以通过各种方法制备,特别是通过以下方法制备:
a)自由基聚合(通常在高压和高温下);
b)使用一种催化剂,该催化剂通常含有一种或多种第IVb、Vb、VIb或VIII族的金属。这些金属通常具有一个或多个配体,例如氧化物、卤化物、醇化物、酯、醚、胺、烷基、链烯基和/或芳基,其可以是π-或σ-配位的。这些金属配合物可以是游离的或被固定到载体上,例如固定到活化的氯化镁、氯化钛(III)、氧化铝或二氧化硅上。这些催化剂可以溶于或不溶于聚合介质中。所述的催化剂本身在聚合反应中可以是活性的或者可以使用另外的活化剂,例如金属烷基化物、金属氢化物、烷基金属卤化物、烷基金属氧化物或烷基金属环氧化物,该金属是第Ia、IIa和/或IIIa族的元素。活化剂可以用例如另外的酯、醚、胺或甲硅烷基醚基团进行改性。这些催化剂体系通常被称为Philips、Standard Oil Indiana、齐格勒(-纳塔)、TNZ(杜邦)、金属茂或单位点催化剂(SSC)。
2.1)中提及的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物,聚丙烯与聚乙烯的混合物(例如PP/HDPE、PP/LDPE)以及不同类型的聚乙烯的混合物(例如LDPE/HDPE)。
3.单-和二-烯烃彼此的共聚物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/丁烯-1共聚物、丙烯/异丁烯共聚物、乙烯/丁烯-1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/环烯共聚物例如乙烯/降冰片烯(COC)共聚物、其中1-烯烃是原位制备的乙烯/1-烯烃共聚物、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/乙酸乙烯基酯共聚物、乙烯/丙烯酸共聚物及其盐(离聚物)、以及乙烯与丙烯和二烯例如己二烯、二环戊二烯或亚乙基降冰片烯的三聚物;以及这些共聚物彼此的混合物或与1)中提及的聚合物的混合物,例如聚丙烯-乙烯/丙烯共聚物,LDPE-乙烯/乙酸乙烯基酯共聚物、LDPE-乙烯/丙烯酸共聚物,LLDPE-乙烯/乙酸乙烯基酯共聚物、LLDPE-乙烯/丙烯酸共聚物以及交替或无规结构的聚亚烷基-一氧化碳共聚物及其与其它聚合物例如聚酰胺的混合物。
4.聚苯乙烯、聚(对-甲基苯乙烯)、聚(α-甲基苯乙烯)。
5.来自乙烯基-芳香族单体的芳香族均聚物和共聚物,这些单体例如是苯乙烯、α-甲基苯乙烯、乙烯基甲苯的所有异构体,例如对-乙烯基甲苯、乙基苯乙烯的所有异构体、丙基苯乙烯、乙烯基联苯、乙烯基萘、乙烯基蒽及其混合物;均聚物和共聚物可以具有一个间规、全同、半全同或无规的立体结构;优选无规聚合物。还包括立构规正嵌段聚合物。
6a.共聚物,包括已经提及的乙烯基-芳香族单体和选自乙烯、丙烯、二烯、腈、酸、马来酸酐、马来酰胺、乙酸乙烯酯、氯乙烯和丙烯酸衍生物及其混合物的共单体,例如苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/乙烯(互聚物)、苯乙烯/甲基丙烯酸烷基酯、苯乙烯/丁二烯/丙烯酸和甲基丙烯酸的烷基酯、苯乙烯/马来酸酐、苯乙烯/丙烯腈/丙烯酸甲酯;由苯乙烯共聚物和另一种聚合物例如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物组成的高冲击强度混合物;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。
6b.通过氢化6)中提及的聚合物而制得的氢化的芳香族聚合物,特别是聚环己基乙烯(PCHE),通常也称为聚乙烯基环己烷(PVCH),其是通过氢化无规聚苯乙烯而制备的。
6c.通过氢化6a)中提及的聚合物而制得的氢化的芳香族聚合物。
均聚物和共聚物可以具有一种间同立构、全同立构、半全同立构或无规立构结构;优选是无规聚合物。同样包括立体嵌段聚合物。
7.乙烯基-芳香族单体的接枝共聚物,例如聚丁二烯上接枝苯乙烯,聚丁二烯/苯乙烯或聚丁二烯/丙烯腈共聚物上接枝苯乙烯,聚丁二烯上接枝苯乙烯和丙烯腈(或甲基丙烯腈);聚丁二烯上接枝苯乙烯、丙烯腈和甲基丙烯酸甲酯;聚丁二烯上接枝苯乙烯和马来酐;聚丁二烯上接枝苯乙烯、丙烯腈和马来酐或马来酰亚胺;聚丁二烯上接枝苯乙烯和马来酰亚胺;聚丁二烯上接枝苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯;乙烯/丙烯/二烯烃三元共聚物上接枝苯乙烯和丙烯腈;聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上接枝苯乙烯和丙烯腈;丙烯酸酯/丁二烯共聚物上接枝苯乙烯和丙烯腈;以及它们与6)中提及的共聚物的混合物,例如已知被称为ABS、MBS、ASA或AES聚合物的那些。
8.含卤素的聚合物,例如氯丁橡胶、氯化橡胶、异丁烯/异戊二烯的氯化和溴化共聚物(卤化丁基橡胶)、氯化或氯磺化聚乙烯、乙烯和氯化乙烯的共聚物、表氯醇的均聚物和共聚物,特别是含卤素的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;以及它们的共聚物,例如氯乙烯/偏二氯乙烯、氯乙烯/乙酸乙烯基酯或偏二氯乙烯/乙酸乙烯基酯共聚物。
9.来源于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,或用丙烯酸丁酯进行抗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)中提及的单体之间的共聚物或与其它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共聚物、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.来源于不饱和醇和胺或它们的酰基衍生物或缩醛的聚合物,例如聚乙烯醇、聚乙酸乙烯基酯、硬脂酸酯、苯甲酸酯或马来酸酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙基酯、聚烯丙基三聚氰胺;以及与在第1点中提及的烯烃形成的共聚物。
12.环醚的均聚物和共聚物,例如聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或它们与二缩水甘油醚的共聚物。
13.聚缩醛,例如聚甲醛,以及含共聚单体例如环氧乙烷的聚甲醛;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯氧和聚苯硫以及它们与聚苯乙烯或聚酰胺的混合物。
15.聚酰胺和来源于二胺和二羧酸和/或氨基羧酸或相应的内酰胺的共聚酰胺,例如聚酰胺4、聚酰胺6、聚酰胺6/6、6/10、6/9、6/12、4/6、12/12、聚酰胺11、聚酰胺12,来源于间二甲苯、二胺和己二酸的芳香族聚酰胺;聚酰胺6/1(聚六亚甲基间苯二甲酰胺,MXD(间二甲苯二胺);由己二胺和间-和/或对-苯二甲酸以及任选一种弹性体作为改性剂制得的聚酰胺,例如聚-2,4,4-三甲基六亚甲基对苯二甲酰胺或聚-间亚苯基间苯二甲酰胺。上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学连接的或接枝的弹性体的嵌段共聚物;或与聚醚例如与聚乙二醇、聚丙二醇或聚丁二醇的嵌段共聚物。以及用EPDM或ABS改性的聚酰胺或共聚酰胺;和在加工期间缩合的聚酰胺(“RIM聚酰胺体系”)。
可以使用的聚酰胺和共聚酰胺的例子特别是来源于ε-己内酰胺、己二酸、癸二酸、十二烷酸、间苯二甲酸、对苯二甲酸、己二胺、四亚甲基二胺、2-甲基-戊二胺、2,2,4-三甲基己二胺、2,4,4-三甲基己二胺、间二甲苯二胺或二(3-甲基-4-氨基环己基)甲烷;以及半芳香族聚酰胺例如聚酰胺66/61,例如由70-95%的聚酰胺6/6和5-30%的聚酰胺6/1组成;以及其中一些聚酰胺6/6被置换的三元共聚物,例如由60-89%的聚酰胺6/6、5-30%的聚酰胺6/1和1-10%的另一种脂肪族聚酰胺组成;后者可以由例如聚酰胺6、聚酰胺11、聚酰胺12或聚酰胺6/12单元组成。因此,这些三元共聚物被称为聚酰胺66/61/6、聚酰胺66/61/11、聚酰胺66/61/12、聚酰胺66/61/610或聚酰胺66/61/612。
16.聚脲、聚酰亚胺、聚酰胺酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲和聚苯并咪唑。
17.来源于二羧酸和二醇和/或来源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、聚对苯二甲酸丙二醇酯、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、聚亚烷基萘甲酸酯(PAN)和聚羟基苯甲酸酯,以及来源于有羟端基的聚醚的嵌段聚醚酯;以及用聚碳酸酯或MBS改性的聚酯。
18.聚碳酸酯和聚酯碳酸酯
19.聚酮
20.聚砜、聚醚砜和聚醚酮。
21.前述聚合物的混合物(聚合混合物),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/PA6.6及共聚物、PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
因此,本发明还涉及本发明的阻燃剂在将耐火性能赋予合成聚合物特别是热塑性塑料中的用途,以及涉及将耐火性能赋予合成聚合物的方法,其中将至少一种本发明的阻燃剂结合进合成聚合物中或涂敷于合成聚合物的表面。
本发明还涉及一种组合物,其包含
a)一种合成聚合物,以及
b)一种本发明的阻燃剂,所述的合成聚合物优选是一种热塑性聚合物。
优选这样的组合物,其中合成聚合物是高抗冲聚苯乙烯(HIPS)、可膨胀的聚苯乙烯(EPS)、膨胀的聚苯乙烯(XPS)、聚苯醚(PPE)、聚烯烃、聚酰胺、聚酯、聚碳酸酯(PC)或ABS(丙烯腈-丁二烯-苯乙烯树脂)或PC/ABS(聚碳酸酯/丙烯腈-丁二烯-苯乙烯树脂)或PPE/HIPS(聚苯醚/高抗冲聚苯乙烯)类型的聚合物混合物,特别是聚酰胺、聚酯、PPE/HIPS混合物或聚乙烯或聚丙烯均聚物或共聚物,后者的例子是乙烯/丙烯共聚物(EPR)、包含少量二烯的乙烯/丙烯/二烯三元共聚物(EPDM)和聚丙烯和聚乙烯(LD、MD、LLD、MD)的混合物。
特别优选包含填料或增强剂的本发明聚合物组合物,特别是玻璃纤维增强的聚合物,例如玻璃纤维增强的聚酰胺。
本发明的组合物可以通过加入或涂敷本发明由组分A和B组成的阻燃剂,或者通过分别加入或涂敷单独组分A和B而进行制备。
优选使用组分A和B的浓度各自彼此独立地为0.1-30wt%,例如0.2-20wt%,优选0.2-15wt%,其基于塑料模塑材料。
本发明的组合物含有例如0.1-50wt%,优选0.3-40wt%,特别是0.3-30wt%或0.8-30wt%的由组分A和B组成的阻燃剂,其基于该组合物。阻燃剂的总量特别取决于所用的聚合物、所用的阻燃剂组合和要获得的阻燃等级。
阻燃组分A和B可以通过例如在混合器中对粉末和/或颗粒形式的所有组分进行预混合,然后在混合装置(特别是双螺杆挤出机)中均化成聚合物熔体而结合进聚合物中。该熔体通常以挤出束的形式抽出,冷却并造粒。组分A和B也可以通过加料装置分别直接引入到混合装置中。
同样可以将阻燃组分A和B与成品聚合物颗粒或粉末混合,并使用注模机直接将混合物加工成模制品。在聚酯的情况中,例如,也可以在缩聚反应期间将阻燃添加剂A和B加入到聚酯材料中。
本发明的聚合物组合物可以是模制材料、薄膜、纤维以及其它模制品的形式,或者可以是表面涂布组合物的形式或可以进一步被加工成这些形式。
在加入至所述聚合物以制备本发明的聚合物组合物之前,可以有利地将本发明的阻燃剂加工成稳定的产品形式。这样一方面可以获得更好的可测量性和更好的劳动卫生(例如没有灰尘),另一方面可以获得用于销售的稳定形式。优选的后一种类产品形状是例如颗粒和凝聚物。前者可以通过例如从挤出机中挤出混合物,并将挤出束造粒而获得。或者,可以将混合物加热至熔点以上,然后用常规方法(例如滴到冷却运输带上或者滴到液体例如水中或者喷雾到空气中)将熔体固化。在这些方法中,本发明的阻燃剂混合物可以如此进行加工,或者在加入一种载体或另一种助剂例如蜡、增塑剂等之后进行加工。所述方法的例子可以见于例如EP-A-392392和EP-A-565184。
为了制备凝聚物,例如可以将一种有机助剂,例如聚乙烯醇、聚乙烯吡咯烷酮或聚乙烯己内酰胺加入到本发明的阻燃剂混合物中,然后进行喷雾干燥。通过这些方法,可以获得一种自由流动的、无尘凝聚物。其也可以根据例如WO-A-03/035736中所述类似的方法得到。
耐火聚合物组合物特别适合于通过例如注模、挤出或压模来制备模制品、薄膜、线和纤维。
除本发明的A和B阻燃组合外,可以向该聚合物组合物中加入其它的常规组分,例如填料和增强剂例如玻璃纤维、玻璃珠或矿物质例如白垩。此外,可以包括其它的添加剂例如抗氧化剂、光稳定剂、润滑剂、着色剂、成核剂或抗静电剂。
任选地存在于本发明组合物中的其它添加剂的例子是:
1.抗氧化剂
1.1.烷基化的单酚,例如2,6-二-叔丁基-4-甲基苯酚、2-丁基-4,6-二甲基苯酚、2,6-二-叔丁基-4-乙基苯酚、2,6-二-叔丁基-4-正丁基苯酚、2,6-二-叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二-叔丁基-4-甲氧基甲基苯酚、线性壬基苯酚或在侧链分枝的壬基苯酚、例如2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一烷-1’-基)-苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)-苯酚、2,4-二甲基-6-(1’-甲基十三烷-1’-基)-苯酚及其混合物。
1.2.烷硫基甲基苯酚,例如2,4-二辛硫基甲基-6-叔丁基苯酚、2,4-二辛硫基甲基-6-甲基苯酚、2,4-二辛硫基甲基-6-乙基苯酚、2,6-二-十二烷硫基甲基-4-壬基苯基。
1.3.氢醌和烷基化的氢醌,例如2,6-二-叔丁基-4-甲氧基-苯酚、2,5-二-叔丁基氢醌、2,5-二-叔戊基氢醌、2,6-二苯基-4-十八碳烷氧基苯酚、2,6-二-叔丁基氢醌、2,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯基硬脂酸酯、二(3,5-二-叔丁基-4-羟基苯基)己二酸酯。
1.4.生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.5.羟基化的硫代二苯基醚,例如2,2’-硫代二(6-叔丁基-4-甲基苯酚)、2,2’-硫代二(4-辛基苯酚)、4,4’-硫代二(6-叔丁基-3-甲基苯酚)、4,4’-硫代二(6-叔丁基-2-甲基苯酚)、4,4’-硫代二(3,6-二-仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟苯基)二硫化物。
1.6.亚烷基双酚,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基二[4-甲基-6-(α-甲基环己基)-苯酚]、2,2’-亚甲基二(4-甲基-6-环己基苯酚)、2,2’-亚甲基二(6-壬基-4-甲基苯酚)、2,2’-亚甲基二(4,6-二-叔丁基苯酚)、2,2’-亚乙基二(4,6-二-叔丁基苯酚)、2,2’-亚乙基二(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基二[6-(α-甲基-苄基)-4-壬基苯酚]、2,2’-亚甲基二[6-(α,α-二甲苄基)-4-壬基苯酚]、4,4’-亚甲基二(2,6-二-叔丁基苯酚)、4,4’-亚甲基二(6-叔丁基-2-甲基苯酚)、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-二(3-叔丁基-5-甲基-2-羟基-苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇二[3,3-二(3’-叔丁基-4’-羟基苯基)丁酸酯]、二(3-叔丁基-4-羟基-5-甲基苯基)-二环戊二烯、二[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二酸酯、1,1-二(3,5-二甲基-2-羟基苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷、2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基-巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7.O-、N-和S-苄基化合物,例如,3,5,3’,5’-四-叔丁基-4,4’-二羟基-二苄基醚、十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯、十三烷基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯、三(3,5-二叔丁基-4-羟基苄基)胺、二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、二(3,5-二-叔丁基-4-羟基苄基)硫醚、异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯。
1.8.羟基苄基化的丙二酸酯,例如2,2-二(3,5-二-叔丁基-2-羟基苄基)丙二酸二-十八烷基酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二十八烷基酯、2,2-二(3,5-二-叔丁基-4-羟基苄基)丙二酸二-十二烷基巯基乙基酯、2,2-二(3,5-二-叔丁基-4-羟基苄基)丙二酸二-[4-(1,1,3,3-四甲基丁基)苯基]酯。
1.9.羟基苄基芳香族化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟基-苄基)-2,4,6-三甲苯、1,4-二(3,5-二-叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯酚。
1.10.三嗪化合物,例如2,4-二辛硫基-6-(3,5-二-叔丁基-4-羟基-苯胺基)-1,3,5-三嗪、2-辛硫基-4,6-二(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛硫基-4,6-二(3,5-二-叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二-叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基-苄基)异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲苄基)异氰脲酸酯、2,4,6-三(3,5-二-叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苯基丙酰基)六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基-苄基)异氰脲酸酯。
1.11.苄基膦酸酯,例如2,5-二-叔丁基-4-羟基苄基-膦酸二甲基酯、3,5-二-叔丁基-4-羟基苄基膦酸二乙基酯、3,5-二-叔丁基-4-羟基苄基膦酸二-十八烷基酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二-十八烷基酯、3,5-二-叔丁基-4-羟基苄基-膦酸单乙基酯的钙盐。
1.12.酰基氨基苯酚,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、N-(3,5-二-叔丁基-4-羟苯基)氨基甲酸辛酯。
1.13.β-(3,5-二-叔丁基-4-羟基苯基)丙酸与单-或多-羟基醇的酯,例如与甲醇、乙醇、正辛醇、异辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酸二酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷形成的酯。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单-或多-羟基醇形成 的酯,例如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酸二酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷;3,9-二[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]十一烷形成的酯。
1.15.β-(3,5-二环己基-4-羟苯基)丙酸与单-或多-羟基醇形成的酯,例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酸二酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷形成的酯。
1.16.3,5-二-叔丁基-4-羟基苯基乙酸与单-或多-羟基醇形成的酯,例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酸二酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷形成的酯。
1.17.β-(3,5-二-叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺、N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)三亚甲基二酰胺、N,N’-二(3,5-二-叔丁基-4-羟基苯基-丙酰基)酰肼)、N,N’-二[2-(3-[3,5-二-叔丁基-4-羟基苯基]-丙酰氧基)乙基]草酰胺(NaugardXL-1,来自Uniroya1)。
1.18.抗坏血酸(维生素C)。
1.19.胺-型抗氧化剂,例如N,N’-二-异丙基-对苯二胺、N,N’-二仲丁基-对苯二胺、N,N’-二(1,4-二甲戊基)-对苯二胺、N,N’-二(1-乙基-3-甲基戊基)-对苯二胺、N,N’-二(1-甲基庚基)-对苯二胺、N,N’-二环己基-对苯二胺、N,N’-二苯基-对苯二胺、N,N’-二(2-萘基)-对苯二胺、N-异丙基-N’-苯基-对苯二胺、N-(1,3-二甲基-丁基)-N’-苯基-对苯二胺、N-(1-甲基庚基)-N’-苯基-对苯二胺、N-环己基-N’-苯基-对苯二胺、4-(对甲苯磺酰胺基)-二苯胺、N,N’二甲基-N,N’-二-仲丁基-对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化的二苯胺,例如p,p’-二-叔辛基-二苯胺、4-正丁基氨基苯酚、4-丁酰氨基苯酚、4-壬酰氨基苯酚、4-十二烷酰氨基苯酚、4-十八烷酰氨基苯酚、二(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲氨基甲基苯酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-二[(2-甲基-苯基)氨基]乙烷、1,2-二(苯基氨基)丙烷、(邻甲苯基)-双胍、二[4-(1’,3’-二甲基-丁基)苯基]胺、叔辛基化的N-苯基-1-萘胺、单-和二-烷基化的叔丁基-/叔辛基-二苯胺的混合物、单-和二-烷基化的壬基-二苯胺的混合物、单-和二-烷基化的十二烷基二苯胺的混合物、单-和二-烷基化的异丙基-/异己基-二苯胺的混合物、单-和二-烷基化的叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单-和二-烷基化的叔丁基-/叔辛基-吩噻嗪的混合物、单-和二-烷基化的叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N’,N’-四苯基-1,4-二氨基丁-2-烯、N,N-二(2,2,6,6-四甲基哌啶-4-基)-六亚甲基二胺、二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、2,2,6,6-四甲基哌啶-4-酮、2,2,6,6-四甲基哌啶-4-醇。
2.UV吸收剂和光稳定剂
2.1.2-(2’-羟基苯基)-苯并***,例如2-(2’-羟基-5’-甲基苯基)-苯并***、2-(3’,5’-二-叔丁基-2’-羟基苯基)苯并***、2-(5’-叔丁基-2’-羟基苯基)苯并***、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)-苯基)-苯并***、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并***、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)-苯并***、2-(2’-羟基-4’-辛氧基苯基)-苯并***、2-(3’,5’-二-叔戊基-2’-羟基苯基)-苯并***、2-(3’,5’-二(α,α-二甲苄基)-2’-羟基苯基)-苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-苯并***、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)-苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基)-苯并***、2,2’-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基-苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-苯并***与聚乙二醇300的酯交换产物;[R-CH2CH2-COO-CH2CH2 2,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并***-2-基-苯基;2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)-苯基]-苯并***;2-[2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)-苯基]-苯并***。
2.2.2-羟基二苯酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2’,4’-三羟基或2’-羟基-4,4’-二甲氧基衍生物。
2.3.未取代的或取代的苯甲酸酯,例如4-叔丁基-苯基水杨酸酯、水杨酸苯酯、辛基苯基水杨酸酯、二苯甲酰基间苯二酚、二(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二-叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二叔丁基-4-羟基苯甲酸十八烷基酯、3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯基酯。
2.4.丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯或异辛酯、α-甲氧基羰基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯或丁酯、α-甲氧基羰基-对甲氧基肉桂酸甲酯、N-(β-甲氧基羰基-β-氰基乙烯基)-2-甲基-二氢吲哚。
2.5.镍化合物,例如2,2’-硫代-二[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,例如1∶1或1∶2配合物,任选与其它配体的配合物例如与正丁胺、三乙醇胺或N-环己基二乙醇胺的配合物、二丁基二硫代氨基甲酸镍、4-羟基-3,5-二-叔丁基苄基膦酸单烷基酯的镍盐,例如甲酯或乙酯的镍盐,酮肟的镍配合物,例如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物,1-苯基-4-月桂酰-5-羟基吡唑的镍配合物,任选与另外的配体的配合物。
2.6.位阻胺,例如二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二(2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、二(1,2,2,6,6-五甲基哌啶-4-基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、正丁基-3,5-二-叔丁基-4-羟基苄基丙二酸二(1,2,2,6,6-五甲基哌啶基)酯、1-羟基乙基-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合产物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)己二胺与4-叔辛基氨基-2,6-二氯-1,3,5-s-三嗪的线性或环状缩合产物、三(2,2,6,6-四甲基-4-哌啶基)次氮基-三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四甲酸酯、1,1’-(1,2-乙烷二基)二(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂酰-氧基-2,2,6,6-四甲基哌啶、二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺环[4.5]癸烷-2,4-二酮、二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N’-二(2,2,6,6-四甲基-4-哌啶基)己二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的线性或环状缩合产物、2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合产物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合产物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺环[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,1,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、4-十六烷氧基-和4-硬脂酰氧基-2,2,6,6-四甲基哌啶的混合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)己二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合产物、1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合产物以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);1,6-二氨基己烷和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁胺和4-丁基氨基-2,2,6,6-四甲基哌啶的缩合产物(CAS登记号[192268-64-7]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代-螺环[4.5]癸烷、7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺环[4.5]癸烷和表氯醇的反应产物、1,1-二(1,2,2,6,6-五甲基-4-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烯、N,N’-二-甲酰基-N,N’-二(2,2,6,6-四甲基-4-哌啶基)己二胺、4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷、马来酐α-烯烃共聚物和2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
2.7.草酸二酰胺,例如4,4’-二辛氧基草酰苯胺、2,2’-二乙氧基草酰苯胺、2,2’-二辛氧基-5,5’-二-叔丁基草酰苯胺、2,2’-二十二烷氧基-5,5’-二-叔丁基草酰苯胺、2-乙氧基-2’-乙基草酰苯胺、N,N’-二(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙基草酰苯胺及其与2-乙氧基-2’-乙基-5,4’-二-叔丁基草酰苯胺的混合物、邻-和对-甲氧基-以及邻-和对-乙氧基-二-取代的草酰苯胺的混合物。
2.8.2-(2-羟基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟苯基)--4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(2-羟基-4-丙-基氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪、2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙氧基]苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属钝化剂,例如N,N’-二苯基草酸二酰胺、N-水杨醛-N’-水杨酰-肼、N,N’-二(水杨酰)肼、N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰氨基-1,2,4-***、二(亚苄基)草酸二酰肼、草酰苯胺、间苯二酸二酰肼、癸二酸二-苯酰肼、N,N’-二乙酰基己二酸二酰肼、N,N’-二-水杨酰草酸二酰肼、N,N’-二-水杨酰硫代丙酸二酰肼。
4.亚磷酸酯和亚膦酸酯,例如亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、亚磷酸三(壬基苯基)酯、亚磷酸三月桂基酯、亚磷酸三-十八烷基酯、二硬脂基-季戊四醇二亚磷酸酯、亚磷酸三(2,4-二-叔丁基苯基)酯、二异癸基季戊四醇二亚磷酸酯、二(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯、二(2,4-二枯基苯基)-季戊四醇二亚磷酸酯、二(2,6-二-叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、二-异癸氧基-季戊四醇二亚磷酸酯、二(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、二(2,4,6-三-叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂基山梨糖醇三亚磷酸酯、四(2,4-二-叔丁基苯基)-4,4’-亚联苯基二亚膦酸酯、6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯、二(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯、二(2,4-二叔丁基-6-甲基-苯基)乙基亚磷酸酯、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂辛环、2,2’,2”-次氮基[三乙基-三(3,3’,5,5’-四丁基-1,1’-联苯-2,2’-二基)-亚磷酸酯]、2-乙基己基-(3,3’,5,5’-四叔丁基-1,1’-联苯-2,2’-二基)-亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧杂磷杂环丙烷。
5.羟胺,例如N,N-二苄基羟胺、N,N-二乙基羟胺、N,N-二辛基羟胺、N,N-二月桂基羟胺、N,N-二-十四烷基羟胺、N,N-二-十六烷基羟胺、N,N-二-十八烷基羟胺、N-十六烷基-N-十八烷基-羟胺、N-十七烷基-N-十八烷基羟胺、来自氢化的牛脂肪胺的N,N-二烷基羟胺。
6.硝酮,例如N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、N-辛基-α-庚基硝酮、N-月桂基-α-十一烷基硝酮、N-十四烷基-α-十三烷基硝酮、N-十六烷基-α-十五烷基硝酮、N-十八烷基-α-十七烷基硝酮、N-十六烷基-α-十七烷基硝酮、N-十八烷基-α-十五烷基硝酮、N-十七烷基-α-十七烷基硝酮、N-十八烷基-α-十六烷基硝酮、衍生于由氢化的牛脂肪胺制得的N,N-二烷基羟胺的硝酮。
7.硫代协同化合物,例如硫代二丙酸二月桂酯或硫代二丙酸二硬脂基酯。
8.破坏过氧化物的化合物,例如β-硫代-二丙酸的酯,例如月桂基、硬脂基酯、肉豆蔻基或十三烷基酯、巯基苯并咪唑、2-巯基苯并咪唑的锌盐、二丁基二硫代氨基甲酸锌、二-十八烷基二硫化物、季戊四醇四(β-十二烷基巯基)丙酸酯。
9.聚酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐以及二价锰盐。
10.碱性共稳定剂,例如三聚氰胺、聚乙烯吡咯烷酮、双氰二酰胺、氰脲酸三烯丙基酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属和碱土金属盐,例如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻醇酸钠、棕榈酸钾、焦儿茶酸锑或焦儿茶酸锌。
11.成核剂,例如无机物质,例如滑石粉、金属氧化物,例如二氧化钛或氧化镁,磷酸盐、优选碱土金属的碳酸盐或硫酸盐;有机化合物,例如单-或多-羧酸及它们的盐,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;聚合物,例如离子共聚合物(“离聚物”)。特别优选的是1,3:2,4-二(3’,4’-二甲基亚苄基)山梨糖醇、1,3:2,4-二(对甲基二亚苄基)山梨糖醇和1,3:2,4-二(亚苄基)山梨糖醇。
12.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃珠、滑石粉、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木屑、以及其它天然产物的粉末和纤维、合成纤维。
13.其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、流变学添加剂、催化剂、流动性改进剂、荧光增白剂、抗静电剂、发泡剂。
14.苯并呋喃酮和吲哚满酮,例如如U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591102中所述,或者是3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二-叔丁基-苯并呋喃-2-酮、5,7-二-叔丁基-3-[4-(2-硬脂酰基-氧基乙氧基)苯基]苯并呋喃-2-酮、3,3’-二[5,7-二-叔丁基-3-(4-[2-羟基乙氧基]苯基)-苯并呋喃-2-酮]、5,7-二-叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧基-苯基)-5,7-二叔丁基-苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮。
本发明的聚合物组合物例如还包含其它的添加剂如抗氧化剂、加工稳定剂、光稳定剂、金属钝化剂、羟胺、硫代协同化合物、铜盐、成核剂、填料、增强剂、颜料和/或抗静电剂,特别是酚类或胺类抗氧化剂、羟胺、亚磷酸酯、亚膦酸酯或/和苯并呋喃酮,更特别是来自UV吸收剂或/和位阻胺种类的光稳定剂。
本发明的阻燃剂和包含它们的聚合物组合物还可以包含其它的阻燃剂(组分C),对于组分C,原则上目前已知的任何阻燃活性成分都是合适的。实例是锑化合物,例如三氧化锑、五氧化锑或锑酸钠,特别是与卤素化合物一起使用;碱土金属氧化物,例如氧化镁或其它金属氧化物例如氧化锌、氧化铝、粘土、硅石、氧化铁或氧化锰;金属氢氧化物,例如氢氧化镁或氢氧化铝;纳米复合材料;矿物土例如蒙脱石或高岭土;改性矿物土,例如包含伯或季铵化合物、三聚氰胺或含磷化合物;含硅化合物,例如硅酸盐如硅酸钙,有机硅化合物(脂肪族或芳香族)如聚硅氧烷;钛酸盐或锆酸盐;金属硼酸盐,例如硼酸锌(水合或非水合的);其它金属化合物例如硫酸钙、碳酸镁、三氧化钼;其它磷化合物,例如磷酸盐、磷酸酯、膦酸盐、亚膦酸盐、磷化氢、磷腈、氧化膦或亚磷酸盐;在这些当中,优选磷酸盐、亚膦酸盐和膦酸盐;位阻烷氧基胺化合物;以及有机卤化物。
例如,位阻烷氧基胺化合物相应于下式(IX),
其中G1和G2各自彼此独立地是C1-C8烷基,或者一起是五亚甲基或六亚甲基,各自优选是C1-C4烷基,特别是甲基,
Z1和Z2各自是甲基,或者Z1和Z2一起是一个桥连基团,特别是形成一个5-或6-元环,优选哌啶环,所得的N-杂环可以是未取代的或取代的,例如被酯、醚、酰胺、氨基、羧基或尿烷基团所取代,
E是烷氧基、链烯氧基、环烷氧基、芳烷氧基、芳氧基或O-T-(OH)b,并且T是C1-C18亚烷基、C5-C18亚环烷基、C5-C18亚环烯基,或者是被苯基或被1或2个C1-C4烷基取代的苯基所取代的C1-C4亚烷基,以及b是1、2或3,并且b不大于T中的碳原子数,并且当b为2或3时,每个羟基与不同的碳原子相连。
E优选是C1-C18烷氧基、C5-C6环烷氧基,或者被1-3个OH基团取代的C1-C18烷基。
式IX的位阻烷氧基胺的例子可以见于US-A-4,983,737、US-A-5,047,489和US-A-5,077,340以及GB-A-2373507(特别是第7页第1行至第31页第1行;第48页第10行至第52页倒数第3行)和WO-A-03/050175(特别是第11页倒数第2行至第37页最后1行;第54页第9行至倒数第3行;第61/62页的化合物NOR1-NOR12)。所提及的参考文献被看作是本申请的一部分。
任选存在于本发明阻燃剂中的有机卤化合物可以是各种类型的化合物。其例子是卤代芳香族化合物,例如卤代苯、卤代联苯类化合物;它们的酚、醚或酯;联苯酚类、二苯基氧化物类;芳香族羧酸类或多酸类,其酸酐、酰胺或酰亚胺;卤代环脂族或多环脂族化合物;以及卤代脂族化合物,例如卤代烷烃、寡聚物和聚合物、磷酸烷基酯和异氰脲酸烷基酯。所提及种类的化合物的例子可以从文献中获知。在这方面,参见例如US-A-4,579,906(例如第3栏第30-41行)、US-A-5,393,812以及“Plastics Additives Handbook”,Ed.By H.Zweifel,5thED.,HanserPubl.,Munich 2001,pages 681-698)。
这些卤代有机阻燃剂组分的个例是:磷酸氯代烷基酯(AntiblazeAB-100,FyrolFR-2)、磷酸三(2-氯乙基)酯、多溴二苯基氧化物(DE-60F,Great Lakes Corp.)、十溴二苯基氧化物(DBDPO,Saytex120E)、三[3-溴-2,2-二(溴甲基)丙基]磷酸酯(PB370,FMCCorp.)、三(2,3-二溴丙基)磷酸酯、三(2,3-二氯丙基)磷酸酯、氯菌酸、四氯酞酸、四溴酞酸、二(N,N’-羟基乙基)-四氯-苯二胺、多-β-氯乙基三磷酸酯混合物、双酚A的二(2,3-二溴丙基醚)(PE68)、溴代环氧树脂、亚乙基二(四溴邻苯二甲酰亚胺)(SaytexBT-93)、二(六氯环戊二烯)环辛烷(Dechlorane Plus)、氯化石蜡、八溴二苯醚、六氯环戊二烯衍生物、1,2-二(三溴苯氧基)乙烷(FF68O)、四溴-双酚A(SaytexRB100)、亚乙基二(二溴降莰烷-二羧酰亚胺)(SaytexBN-451)、二(六氯环戊二烯)-环辛烷、聚四氟乙烯(TeflonGC)、三(2,3-二溴丙基)异氰脲酸酯、亚乙基二(四溴邻苯二甲酰亚胺)。
在这些当中,优选有机溴阻燃剂。
可以提及的含磷阻燃剂的例子是:
四苯基间苯二酚二亚磷酸酯(FyroflexRDP)、磷酸三苯基酯、磷酸三辛基酯、磷酸三甲苯基酯、四(羟基甲基)硫化磷、二乙基-N,N-二(2-羟基乙基)氨基甲基膦酸酯、磷酸的羟烷基酯、多磷酸铵(APP)或(HostaflamAP750)、间苯二酚二磷酸酯寡聚物(RDP)、磷腈阻燃剂和乙二胺二磷酸酯(EDAP)。
来自含磷阻燃剂类型的阻燃剂组分C有利地是一种三聚氰胺的盐,或三聚氰胺与含磷的酸的缩合产物,即含磷的一元酸,例如磷酸、膦酸或优选在每种情况中仅仅具有一个酸当量的次膦酸;更特别是,膦酸烷基酯,优选可以考虑的是次膦酸烷基酯。阳离子组分例如是三聚氰胺、蜜白胺、蜜勒胺或三聚氰胺的更高级的缩合产物,并优选是三聚氰胺或蜜白胺。这些盐及它们的制备描述于例如EP-A-363321和WO-A-01/57051中。
特别合适作为本发明阻燃剂或阻燃聚合物组合物的组分C的是有机次膦酸或二次膦酸的盐,特别是式X和XI的盐
其中
R1和R2,相同的或不同,是C1-C6烷基,特别是C1-C4烷基,或是C6-C10芳基;
R3是C1-C10亚烷基、C6-C10亚芳基、-烷基亚芳基或-芳基亚烷基;
M是镁、钙、铝、锌、三聚氰胺或三聚氰胺的缩合产物,
m1是1、2或3;
n1是1或3,并且
x是1或2。
M优选是锌、铝、三聚氰胺、蜜白胺或蜜勒胺,特别是锌或铝。芳基和亚芳基、烷基亚芳基和芳基亚烷基包括,特别是,苯基、萘基、甲苯基、二甲苯基、乙基苯基、2,4,6-三甲苯基、丙基苯基或叔丁基苯基,以及亚苯基、亚萘基、甲基亚苯基、乙基亚苯基或叔丁基亚苯基、甲基亚萘基、乙基亚萘基、叔丁基亚萘基、苯基亚甲基、苯基亚丙基以及相应的甲苯基和二甲苯基类似物。
因此,特别应该强调的是本发明的阻燃剂和阻燃聚合物组合物,其中还包括其它的阻燃活性成分(组分C),至少一种这样的组分,其选自锑化合物、金属氧化物或氢氧化物、纳米复合材料、矿物土、改性的矿物土、有机或无机硅化合物、钛酸盐、锆酸盐、金属硼酸盐、磷化合物、位阻烷氧基胺化合物和/或有机卤化合物的类型,例如其中组分C是至少一种选自锑化合物、位阻烷氧基胺化合物、磷化合物或/和有机卤化合物类型的那些。特别合适的组分C是磷酸盐、磷酸酯、膦酸盐、亚膦酸盐、磷化氢、氧化膦、亚磷酸盐或/和磷腈,更特别是式X或/和XI的次磷酸的金属盐或三聚氰胺(包括其缩合产物)盐。
下面的实施例进一步说明本发明。
实施例:
聚合物:
来自Albis(BASF制造)的玻璃纤维填充的聚酰胺66(GF-PA66):UltramiduA3EG5。
添加剂:
Irgamod195(式I的化合物,其中R=C2H5,R’=Ca++/2,n=1,R13=R14=C(CH3)3,以及R15=H)。
Melapur200(=三聚氰胺多磷酸盐)
NOR1(=1,6-己二胺、N,N’-二(2,2,6,6-四甲基-4-哌啶基)-,和2,4,6-三氯-1,3,5-三嗪的聚合物,和3-溴-1-丙烯的反应产物,N-丁基-1-丁胺和N-丁基-2,2,6,6-四甲基-4-哌啶胺,氧化的,氢化的);
IrganoxHP136=3-羟基-5,7-二叔丁基-呋喃-2-酮和邻二甲苯的反应产物;
Irganox1098=N,N’-己-1,6-二基-二[3-(3,5-二叔丁基-4-羟基苯基丙酰胺)];
硬脂酸钙。
实施例1
干燥混合下表中所列的组分并在60℃下真空干燥至少12小时。在紧密啮合并正转的Haake TW100双螺杆挤出机中用锥形螺杆挤出所得的混合物。
温度程序:210-260℃;真空:3mbar;转速:60rev./min.;生产量:30g/min.;用线料挤塑并通过穿孔模进行挤出。挤出束的冷却在水浴中进行,接着进行造粒。在热台工具中将颗粒压缩至2mm厚的片。从用于阻燃测试的片上切下试样(20×120mm)。
比较例:
测试号 | 聚合物 | 添加剂* |
CE-1 | PBT | 15%Melapur2000.25%IrganoxHP2215 |
CE-2 | PBT | 10%Irgamod1950.25%IrganoxHP2215 |
CE-3 | GF-PA66 | 15%MelapurMC0.3%IrganoxB1171 |
CE-4 | GF-PA66 | 10%Irgamod1950.3%IrganoxB1171 |
*百分比表示重量百分比,其基于总的组合物。
本发明的实施例:
测试号 | 聚合物 | 添加剂* |
E-1 | PBT | 15%Melapur20010%Irgamod1950.25%IrganoxHP2215 |
E-2 | PBT | 15%MelapurMP10%Irgamod1950.25%IrganoxHP2215 |
E-3 | GF-PA66 | 15%MelapurMC10%Irgamod1950.3%IrganoxB1171 |
E-4 | GF-PA66 | 15%MelapurMP10%Irgamod1950.3%IrganoxB1171 |
*百分比表示重量百分比,其基于总的组合物。
点燃试样。结果发现包含本发明组合物(与比较例对比)的试样自动灭火。
实施例2
将聚丙烯(MoplenHF 500N)与下表中所示的添加剂干燥混合。聚丙烯包含0.1wt%硬脂酸钙和0.2wt%IrganoxB225作为基础稳定剂。在双螺杆挤出机(ZSK 25,Werner & Pfleiderer)中在230℃的最高温度(加热区1-6)和在每分钟100转的4kg/小时的生产量下挤出混合物,在水浴中冷却之后对挤出束进行造粒。
在热压机(Fontijne)中在230℃和50kN的压力下将颗粒压缩至200μm厚的薄膜。在25℃和50%的相对湿度下调节48小时后,根据DIN 4102,Part 1,Classification 32测定薄膜的阻燃作用。
DIN 4102测试的结果,边缘点燃(薄膜尺寸190×90mm)。
配方 | 平均烧毁长度(mm) | 总燃烧时间(秒) | 等级 |
空白 | 190 | 42 | B3 |
0.25%NOR1+0.25%Irgamod 195+0.5%Melapur MC | 57 | 13 | B2 |
由上述结果可看出,当以非常低的浓度使用时,本发明的配方为聚丙烯提供了阻燃性和自熄性能。
Claims (23)
1.一种阻燃剂,其包含
A.至少一种式I的有机膦酸盐或酯
其中R是氢、C1-C20烷基、未取代的或被C1-C4烷基取代的苯基或萘基,R’是氢、或M1 r+/r,n是0-6的整数,M1 r+是r价金属离子或铵离子,r是1-4的整数,
R13是异丙基、异丁基、叔丁基、环己基或者是被1-3个C1-C4烷基取代的环烷基,
R14是氢、C1-C4烷基、环烷基或者是被1-3个C1-C4烷基取代的环己基,及
R15是氢、C1-C18烷基、三甲基甲硅烷基、苄基、苯基或磺酰基;和
B.至少一种式III-VIIIa的含氮阻燃剂组分
其中R4-R6各自彼此独立地是氢、C1-C8烷基、C5-C6环烷基或C1-C4烷基-C5-C6环烷基,它们各自是未取代的或被羟基或C1-C4-羟基烷基取代;C2-C8链烯基,C1-C8烷氧基,-酰基,-酰氧基,C6-C12芳基,-O-R2或-N(R2)R3,R2和R3是氢、C1-C4烷基、C5-C6环烷基、C2-C8链烯基、C1-C4羟基烷基或C6-C12芳基,条件是R4-R6不同时是氢以及在式III中不同时是-NH2,以及在式VII中至少存在一个能够加上一个质子的基团,
R7-R11表示与R4-R6相同的基团,但是-N(R2)R3取代基除外,X是质子酸的阴离子,x是从后者转移到三嗪化合物上的质子的数目,y是从质子酸中夺取的质子的数目;
或多磷酸铵、三聚氰胺磷酸铵、三聚氰胺多磷酸铵、三聚氰胺焦磷酸铵、三聚氰胺的缩合产物或/和三聚氰胺与磷酸的反应产物或/和三聚氰胺的缩合产物与磷酸的反应产物或它们的混合物。
2.根据权利要求1的阻燃剂,其中R’是Na+、K+、Mg++/2、Ca++/2、Ba++/2、Zn++/2或Al+++/3。
3.根据权利要求1的阻燃剂,其中R13是叔丁基,R14是氢或C1-C4烷基,并且R15是氢。
4.根据权利要求1的阻燃剂,其中组分B是至少一种式VII或/和VIIIa的化合物或/和多磷酸铵、三聚氰胺多磷酸铵、三聚氰胺焦磷酸铵、三聚氰胺的缩合产物或/和三聚氰胺与磷酸的反应产物或/和三聚氰胺的缩合产物与磷酸的反应产物或它们的混合物。
5.根据权利要求1的阻燃剂,其中组分B是苯代三聚氰二胺、三(羟乙基)异氰脲酸酯、尿囊素、甘脲、三聚氰胺氰尿酸酯、三聚氰胺磷酸盐、二-三聚氰胺磷酸盐、三聚氰胺焦磷酸盐、脲氰尿酸盐、多磷酸铵、三聚氰胺多磷酸盐、三聚氰胺硼酸盐、三聚氰胺多磷酸铵或三聚氰胺焦磷酸铵。
6.根据权利要求1的阻燃剂,其中组分B是来自蜜勒胺、蜜白胺和/或氰尿酰胺系列的三聚氰胺的缩合产物,或三聚氰胺与磷酸的反应产物,和/或三聚氰胺的缩合产物与磷酸的反应产物或它们的混合物。
7.根据权利要求6的阻燃剂,其中组分B是二-三聚氰胺焦磷酸盐、三聚氰胺多磷酸盐、蜜勒胺多磷酸盐、蜜白胺多磷酸盐、和/或该类型的混合聚合盐。
8.根据权利要求1的阻燃剂,其还包含其它的阻燃组分C。
9.根据权利要求8的阻燃剂,其中组分C是至少一种选自锑化合物、金属氧化物或氢氧化物、纳米复合材料、矿物土、改性的矿物土、有机或无机硅化合物、钛酸盐、锆酸盐、金属硼酸盐、磷化合物、位阻烷氧基胺化合物和/或有机卤化合物的阻燃活性成分。
10.根据权利要求9的阻燃剂,其中组分C是至少一种选自锑化合物、位阻烷氧基胺化合物、磷化合物或/和有机卤化合物类型的阻燃活性成分。
11.根据权利要求10的阻燃剂,其中组分C是次膦酸烷基酯的金属盐或后者与三聚氰胺或与三聚氰胺缩合产物的盐。
13.根据权利要求12的阻燃剂,其中R1和R2,相同或不同,是C1-C4烷基。
14.一种组合物,其包含
a)一种合成聚合物,以及
b)至少一种权利要求1-13任一项的阻燃剂。
15.根据权利要求14所述的组合物,其中所述合成聚合物是热塑性聚合物。
16.根据权利要求14的组合物,其中合成聚合物是高抗冲聚苯乙烯(HIPS)、可膨胀的聚苯乙烯(EPS)、膨胀的聚苯乙烯(XPS)、聚苯醚(PPE)、聚烯烃、聚酰胺、聚酯、聚碳酸酯或ABS(丙烯腈-丁二烯-苯乙烯树脂)或PC/ABS(聚碳酸酯/丙烯腈-丁二烯-苯乙烯树脂)或PPE/HIPS(聚苯醚/高抗冲聚苯乙烯)类型的聚合物混合物。
17.根据权利要求14的组合物,其包含填料或增强剂。
18.根据权利要求17的组合物,其包含玻璃纤维。
19.根据权利要求14的组合物,其包含其它添加剂。
20.根据权利要求19的组合物,其包含作为其它添加剂的抗氧化剂、加工稳定剂、光稳定剂、金属钝化剂、羟胺、硫代协同化合物、铜盐、成核剂、填料、增强剂、颜料和/或抗静电剂。
21.根据权利要求20的组合物,其包含作为抗氧剂或加工稳定剂的酚类或胺类抗氧化剂、羟胺、亚磷酸酯、亚膦酸酯或/和苯并呋喃酮,或/和作为光稳定剂的UV吸收剂或/和来自位阻胺种类的光稳定剂。
22.权利要求1所定义的阻燃剂用于将耐火性能赋予合成聚合物的用途。
23.一种将耐火性能赋予合成聚合物的方法,其中将至少一种权利要求1所定义的阻燃剂结合进合成聚合物中或涂敷于其表面。
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EP04102078.5 | 2004-05-13 | ||
EP04102078 | 2004-05-13 | ||
PCT/EP2005/052126 WO2005113661A1 (en) | 2004-05-13 | 2005-05-11 | Flame retardants |
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CN1950436A CN1950436A (zh) | 2007-04-18 |
CN1950436B true CN1950436B (zh) | 2012-09-05 |
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US (1) | US20070228343A1 (zh) |
EP (1) | EP1751223B1 (zh) |
JP (1) | JP5118961B2 (zh) |
CN (1) | CN1950436B (zh) |
AT (1) | ATE439399T1 (zh) |
DE (1) | DE602005015956D1 (zh) |
WO (1) | WO2005113661A1 (zh) |
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Also Published As
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ATE439399T1 (de) | 2009-08-15 |
EP1751223B1 (en) | 2009-08-12 |
EP1751223A1 (en) | 2007-02-14 |
US20070228343A1 (en) | 2007-10-04 |
JP2007537321A (ja) | 2007-12-20 |
WO2005113661A1 (en) | 2005-12-01 |
JP5118961B2 (ja) | 2013-01-16 |
DE602005015956D1 (de) | 2009-09-24 |
CN1950436A (zh) | 2007-04-18 |
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