CN1823127A - 阻燃性聚乳酸 - Google Patents
阻燃性聚乳酸 Download PDFInfo
- Publication number
- CN1823127A CN1823127A CNA2004800206070A CN200480020607A CN1823127A CN 1823127 A CN1823127 A CN 1823127A CN A2004800206070 A CNA2004800206070 A CN A2004800206070A CN 200480020607 A CN200480020607 A CN 200480020607A CN 1823127 A CN1823127 A CN 1823127A
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl
- acid
- phenyl
- 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.)
- Granted
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 85
- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 46
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000004626 polylactic acid Substances 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 150000001412 amines Chemical class 0.000 claims abstract description 57
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003381 stabilizer Substances 0.000 claims abstract description 22
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 13
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000002195 synergetic effect Effects 0.000 claims abstract description 8
- -1 isocyanuric acid ester Chemical class 0.000 claims description 195
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 150000002148 esters Chemical class 0.000 claims description 47
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000001118 alkylidene group Chemical group 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000011159 matrix material Substances 0.000 claims description 18
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000002516 radical scavenger Substances 0.000 claims description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 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 claims description 10
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 9
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 description 6
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical group [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 6
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 6
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 6
- 229960001545 hydrotalcite Drugs 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004914 cyclooctane Substances 0.000 claims description 4
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- 229940032021 tetramune Drugs 0.000 claims description 4
- 125000006839 xylylene group Chemical group 0.000 claims description 4
- MRHCTSJVGDQROS-UHFFFAOYSA-N 1,2,3-tribromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C(Br)=C1Br MRHCTSJVGDQROS-UHFFFAOYSA-N 0.000 claims description 3
- OKELZJLBUAZSCL-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethyl-n-octadecylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCCCCCCCCCCCCCCCC)CC(C)(C)N1OC1CCCCC1 OKELZJLBUAZSCL-UHFFFAOYSA-N 0.000 claims description 3
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 claims description 3
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 3
- HENGFBWGINVKQQ-UHFFFAOYSA-N 4-chloro-n-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazin-2-amine Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC1=NC=NC(Cl)=N1 HENGFBWGINVKQQ-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004902 Softening Agent Substances 0.000 claims description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006309 butyl amino group Chemical group 0.000 claims description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 3
- 239000008116 calcium stearate Substances 0.000 claims description 3
- 235000013539 calcium stearate Nutrition 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 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 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 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
- 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 3
- 239000001205 polyphosphate Substances 0.000 claims description 3
- 235000011176 polyphosphates Nutrition 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004711 α-olefin Substances 0.000 claims description 3
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 claims description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 2
- BGGGMYCMZTXZBY-UHFFFAOYSA-N (3-hydroxyphenyl) phosphono hydrogen phosphate Chemical compound OC1=CC=CC(OP(O)(=O)OP(O)(O)=O)=C1 BGGGMYCMZTXZBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- NDRKXFLZSRHAJE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4-tribromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=CC=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br NDRKXFLZSRHAJE-UHFFFAOYSA-N 0.000 claims description 2
- KFSRWJOFHDWKBX-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetrachlorobenzene-1,2-diamine Chemical compound ClN(Cl)C1=CC=CC=C1N(Cl)Cl KFSRWJOFHDWKBX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 claims description 2
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 claims description 2
- OSFWMKHTCZJYOR-UHFFFAOYSA-N 4-chloro-n-[4-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazin-2-amine Chemical compound C1C(C)(C)N(O)C(C)(C)CC1CCCCNC1=NC=NC(Cl)=N1 OSFWMKHTCZJYOR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 229910001051 Magnalium Inorganic materials 0.000 claims description 2
- 229910003849 O-Si Inorganic materials 0.000 claims description 2
- YHDJLQXSHIIBAQ-UHFFFAOYSA-N OP(O)OP(O)O.C1(=CC=CC=C1)C1=C(C(=C(C(=C1O)C1=CC=CC=C1)O)C1=CC=CC=C1)C1=CC=CC=C1 Chemical class OP(O)OP(O)O.C1(=CC=CC=C1)C1=C(C(=C(C(=C1O)C1=CC=CC=C1)O)C1=CC=CC=C1)C1=CC=CC=C1 YHDJLQXSHIIBAQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910003872 O—Si Inorganic materials 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 claims description 2
- 159000000032 aromatic acids Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- COAPBYURHXLGMG-UHFFFAOYSA-N azane;1,3,5-triazine-2,4,6-triamine Chemical compound N.NC1=NC(N)=NC(N)=N1 COAPBYURHXLGMG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 229960005141 piperazine Drugs 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000011495 polyisocyanurate Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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- 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 claims description 2
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Classifications
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
聚乳酸通过引入下面组分的协同混合物赋予阻燃性:(i)至少一种位阻胺稳定剂和(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺型阻燃剂中的至少一种普通阻燃剂。本发明的组合物兼顾了良好阻燃剂性能与光稳定性和良好机械性能。
Description
本发明涉及通过在聚乳酸中添加至少一种位阻胺稳定剂和至少一种普通阻燃剂的协同混合物使聚乳酸阻燃的新型方法。本发明还涉及,通过在其中引入至少一种位阻胺稳定剂和至少一种普通阻燃剂,变成稳定化而可以耐光、热和氧并且变成阻燃性的聚乳酸纤维、膜、模制品和泡沫制品。
本发明的背景
US专利No.5,096,950公开了某些NOR(N-烷氧基)位阻胺与溴化含Sb2O3阻燃剂一起在聚丙烯中的共同使用。
US专利No.5,393,812公开了通过卤代烃基磷酸酯或膦酸酯阻燃剂与烷氧基胺官能化位阻胺相结合的结合物来变成阻燃性的聚烯烃组合物。
US专利No.5,844,026公开了包括某些NOR位阻胺和某些传统阻燃剂的聚烯烃组合物。
US专利No.6,117,995公开道,某些N-烷氧基位阻胺可以用作有机聚合物的阻燃剂。
US专利No.6,271,377公开了包括N-羟基烷氧基位阻胺和卤代阻燃剂的聚烯烃组合物。
US专利No.6,309,987和同族WO99/54530教导了包括N-烷氧基胺的聚烯烃阻燃性无纺织物。
US专利No.6,262,161公开了具有改进的抗引燃性的无规互聚物,例如乙烯和/或一种或多种α-烯烃单体与一种或多种乙烯基芳族单体的聚合物类,它包括填料和至少一种其它组分(可以是位阻胺稳定剂)。
A Revolutionary UV Stable Flame Retardant System forPolyolefins-R.Srinivasan,A.Gupta and D.Horsey,Int.Conf.Addit.Polyolefins 1998,69-83,教导了包括某些NOR位阻胺与含卤素和磷的普通阻燃剂的聚烯烃。
Advances in a Revolutionary Flame Retardant System forPolyolefins-R.Srinivasan,B.Rotzinger,Polyolefins 2000,Int Conf.Polyolefins 2000,571-581,教导了包括某些NOR位阻胺与含溴和磷的阻燃剂的聚烯烃。
EP 0792911 A2公开了包括烷氧基胺官能化位阻胺和三(三卤代戊基)磷酸酯阻燃剂的聚烯烃组合物。
US专利No.6,472,456和悬而未决的US申请No.09/714,717(2000年11月16日申请)公开了某些N-烷氧基位阻胺作为阻燃剂的用途。
EP 1038912公开了作为阻燃剂的特定的烃氧基位阻胺化合物。
Research Disclosure,Sept.2000,No.437087,June 2000,No.434095和Dec.2000,No.440128也公开了作为阻燃剂的某些烃氧基位阻胺化合物的功效。
今天的阻燃剂(FR)市场是由用于利用化学和/或物理手段干涉燃烧过程的一些产品组成的。根据机理,这些FR已经建议在制品在气相、冷凝相或两者中的燃烧过程中发挥作用。该有机卤素化合物被揭示产生卤素物质(例如HX),后者在气相中干涉来自聚合物基材中的自由基有机“燃料”。增效剂被建议与HX反应形成附加的化学物质,后者会干涉在气相中的燃烧,如氧化锑与HX反应形成锑卤化物和水蒸汽。锑化合物如三氧化锑也用作自由基清除剂,形成卤化锑。因此,它能够抑制火势的蔓延。
虽然锑化合物就成本性能而言是有效的,但是它最近遇到大量问题,归因于在卤代阻燃剂存在下燃烧过程中所形成的副产物的毒性。氧化锑常常含有痕量的砷化合物,它被怀疑是致癌物质。由于这些生态问题,现在掀起了在目前的商购阻燃剂应用中替换三氧化锑的运动。然而,非常难以发现既是环境友好的和又是有效(就性能价格比而言)的有效增效剂。
添加阻燃剂添加剂的另一个理由是在火焰的阻燃应用中防止滴淌。在燃烧过程中的滴淌是聚合物的各个部分以液滴形状从基体上分离的过程。最常常,该液滴是燃烧性的并引起了火焰传播的巨大危险。通常的措施是将填料如滑石大量地添加到聚合物中,对于机械性能有一些负面影响。有时使用的填料包括碳酸钙,碳酸镁,硼酸锌,硅酸盐,硅氧烷,玻璃纤维,玻璃泡,石棉,高岭土,云母,硫酸钡,硫酸钙,金属氧化物,水合物和氢氧化物如氧化锌,氢氧化镁,三水氧化铝,硅石,硅酸钙和硅酸镁。
已经发现,当将位阻胺稳定剂与普通的有机卤素阻燃剂、含磷阻燃剂、异氰脲酸酯阻燃剂或蜜胺型阻燃剂一起添加到聚乳酸聚合物中时,制备了具有良好阻燃性能的聚乳酸聚合物。由于这一结合使用,阻燃性填料或普通的填料可以大大地减少或被替代。由于这些位阻胺化合物具有稳定剂的活性,本发明的聚合物组合物有效地得到保护,消除了光、氧和/或热的有害影响。
详细公开
本发明涉及阻燃性聚乳酸聚合物组合物,它包括聚乳酸聚合物基质和下面组分的协同混合物:
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺型阻燃剂中的至少一种普通阻燃剂。
阻燃性填料不是为了改进阻燃性能和在例如UL-94燃烧试验(下文)中实现较高的评级所需要的。因此,本发明的组合物可以含有仅仅少量的阻燃性填料,例如低于聚乳酸聚合物组分重量的3wt%,例如低于1wt%,例如低于0.1wt%;例如,该组合物基本上不含阻燃性填料。
阻燃性填料在现有技术中是已知的并且选自氢氧化镁,三水氧化铝和硼酸锌。阻燃性填料是为了阻燃性能而使用的,并且以足够高的水平使用的无机化合物,因此被认为是“填料”。
如果普通的填料如滑石,碳酸钙等等正常地例如为了流动性质而使用,以便减少正在燃烧的液滴(本身不是不阻燃性的)的传播,此类普通填料也可以通过使用本发明组合物来减少。例如,本发明的组合物可以含有仅仅少量的普通填料,例如低于聚乳酸聚合物组分重量的3wt%,例如低于1wt%,例如低于0.1wt%;例如,该组合物基本上不含普通填料。
此外,本发明允许普通的填料替代更昂贵的阻燃性填料。
本发明组合物符合阻燃剂技术规格,尽管含有仅仅少量的锑化合物如Sb2O3,例如低于聚乳酸聚合物组分重量的1wt%,例如低于0.1wt%;例如,该组合物基本上不含锑。
聚乳酸
聚乳酸是公开在US专利No 5,447,962,5,484,881,6,114,495和6,214,967中的聚合物和共聚物,它们的相关公开内容被引入这里供参考。
用于本发明中的聚乳酸或乳酸和羟基羧酸的共聚物是通过使用乳酸或丙交酯即乳酸的环状二聚物和羟基羧酸作为原料来制备的。
举例性质的羟基羧酸包括乙醇酸,羟基丁酸,羟基戊酸,羟基戊酸,羟基己酸和羟基庚酸。
具体地说,优选使用乙醇酸,3-羟基乳酸,4-羟基乳酸,3-羟基戊酸或6-羟基己酸。在某些情况下,其它单体能够合适地作为混合物来使用。
该乳酸聚合物可以通过脱水缩聚来直接从乳酸制备或可以通过丙交酯的开环聚合来制备。
当低分子量聚合物允许时,通过乳酸的脱水缩合获得聚合物。当需要高分子聚合物时,优选通过交酯的开环聚合获得聚合物。
能够用于开环聚合的交酯类是L-丙交酯,D-丙交酯,meso-交酯和这些交酯的混合物。D-或L-交酯与具有相反的旋光度的交酯的混合物是优选的。混合比,D-或L-交酯/旋光对映体是在例如95/5到50/50之间。
通过聚合纯旋光异构体或不同的掺混物,可以获得聚合物,它们具有不同的立体化学结构,影响它们的回弹性和结晶度以及它们的机械和热性质。
乳酸基聚合物的聚合度是在例如150至20,000之间。
聚合能够在溶剂存在或不存在的情况下进行。考虑到溶剂回收问题,没有溶剂的本体聚合在工业上是优选的。
下面解释通过丙交酯和乙交酯的开环聚合反应制备乳酸型聚合物的方法。
开环聚合是在催化剂存在下进行的。能够使用的催化剂一般是锌或锡的氯化物或羧酸盐,并且包括,例如,辛酸亚锡,四氯化锡,氯化锌,四氯化钛,氯化铁,三氟化硼醚配合物,氯化铝,三氟化锑,氧化铅和其它含多价金属的化合物。对于多价金属没有特殊限制。锡化合物和锌化合物是优选使用的。然而,对于为生物相容性材料和食品使用泡沫体时,这些金属必须考虑到毒性来进行选择。
催化剂的用量例如是,对于丙交酯或对于丙交酯和乙交酯的总重量的0.001-0.1wt%。
已知的链增长剂能够用于该聚合。优选的链增长剂是高级醇,如月桂醇和醇酸如乳酸和乙醇酸。该聚合速率在链增长剂存在下会提高,能够在短时间内获得聚合物。聚合物的分子量也能够通过改变链增长剂的量来控制。然而,太多的链增长剂倾向于降低所形成的聚合物的分子量。因此,链增长剂的量优选是丙交酯或丙交酯和乙交酯总重量的0.1wt%或更低。
聚合或共聚合能够在溶剂存在或不存在的情况下进行。优选进行丙交酯或乙交酯的在熔化状态下的本体聚合以获得高分子量聚合物。
对于熔体聚合的情况,该聚合温度可以一般在单体,丙交酯或丙交酯和乙交酯的熔点(约90℃)以上。对于使用溶剂如氯仿的溶液聚合,该聚合能够在低于丙交酯或丙交酯和乙交酯的熔点的某温度下进行。在任何情况下,高于250℃的聚合温度是不适宜的,因为导致所形成聚合物的分解。
组分(i)的位阻胺稳定剂
该位阻胺例如是单体化合物或是低聚或高聚化合物。
组分(i)的位阻胺稳定剂是现有技术中已知的,并且例如具有下式:
其中
G1和G2独立地是具有1到8个碳原子的烷基或一起是五亚甲基,
Z1和Z2各自是甲基,或Z1和Z2一起形成连接用结构部分,它可以另外被酯,醚,酰胺,氨基,羧基或尿烷基团取代,和
E是氧基,羟基,烷氧基,环烷氧基,芳烷氧基,芳氧基,-O-CO-OZ3,-O-Si(Z4)3,-O-PO(OZ5)2或-O-CH2-OZ6,其中Z3,Z4,Z5和Z6选自氢,脂肪族,芳脂族和芳族结构部分;或E是-O-T-(OH)b,
T是具有1到18个碳原子的直链或支链亚烷基,具有5到18个碳原子的亚环烷基,具有5到18个碳原子的亚环链烯基,被苯基或被一个或两个1-4个碳原子的烷基取代的苯基所取代的具有1-4个碳原子的直链或支链亚烷基;
b是1,2或3,前提条件是b不能超过在T中的碳原子的数量,并且当b是2或3时,各羟基连接于T的不同碳原子上。
E例如是氧基,羟基,烷氧基,环烷氧基或芳烷氧基。例如,E是甲氧基,丙氧基,环己氧基或辛基氧基。
组分(i)的位阻胺稳定剂例如具有通式A-R
其中
E是氧基,羟基,具有1到18个碳原子的烷氧基,具有5到12个碳原子的环烷氧基或具有7到15个碳原子的芳烷氧基,或E是-O-T-(OH)b,
T是具有1到18个碳原子的直链或支链亚烷基,具有5到18个碳原子的亚环烷基,具有5到18个碳原子的亚环链烯基,被苯基或被一个或两个1-4个碳原子的烷基取代的苯基所取代的具有1-4个碳原子的直链或支链亚烷基;
b是1,2或3,前提条件是b不能超过在T中的碳原子的数量,并且当b是2或3时,各羟基连接于T的不同碳原子上;
R是氢或甲基,
m是1到4,
当m是1时,
R2是氢,C1-C18烷基或该烷基任选被一个或多个氧原子***,C2-C12链烯基,C6-C10芳基,C7-C18芳烷基,缩水甘油基,脂肪族、环脂族或芳族羧酸的或氨基甲酸的一价酰基,例如具有2-18个C原子的脂族羧酸,具有5-12个C原子的环脂族羧酸或具有7-15个C原子的芳族羧酸的酰基,或
其中x是0或1,
其中y是2-4;
当m是2时,
R2是C1-C12亚烷基,C4-C12亚链烯基,亚二甲苯基,脂肪族、环脂族、芳脂族或芳族二羧酸的或二氨基甲酸的二价酰基,例如具有2-18个C原子的脂族二羧酸,具有8-14个C原子的环脂族或芳族二羧酸,或具有8-14个C原子的脂肪族、环脂族或芳族二氨基甲酸的酰基;
其中D1和D2独立地是氢,含有至多8个碳原子的烷基,芳基或芳烷基基团(包括3,5-二叔丁基-4-羟基苄基),D3是氢,或含有至多18个碳原子的烷基或链烯基,和d是0-20;
当m是3时,R2是脂肪族、不饱和脂肪族、环脂族或芳族三羧酸的三价酰基;
当m是4时,R2是饱和或不饱和脂肪族或芳族四羧酸类,包括1,2,3,4-丁烷四羧酸,1,2,3,4-丁-2-烯四羧酸,以及1,2,3,5-和1,2,4,5-戊烷四羧酸,的四价酰基;
p是1,2或3,
R3是氢,C1-C12烷基,C5-C7环烷基,C7-C9芳烷基,C2-C18链烷酰基(alkanoyl),C3-C5链烯酰基或苯甲酰基(alkenoyl);
当p是1时,
R4是氢,未被取代的或被氰基、羰基或脲基取代的C1-C18烷基、C5-C7环烷基、C2-C8链烯基,芳基,芳烷基,或它是缩水甘油基,式-CH2-CH(OH)-Z或式-CO-Z或-CONH-Z的基团,其中Z是氢、甲基或苯基;或以下结构式的基团
或
其中h是0或1,
R3和R4一起,当p是1时,能够是4到6个碳原子的亚烷基或2-氧代多亚烷基,脂肪族或芳族1,2-或1,3-二羧酸的环状酰基,
当p是2时,
R4是直接的键或是C1-C12亚烷基,C6-C12亚芳基,亚二甲苯基,-CH2CH(OH)-CH2基团或基团-CH2-CH(OH)-CH2-O-X-O-CH2-CH(OH)-CH2-,其中X是C2-C10亚烷基,C6-C15亚芳基或C6-C12亚环烷基;或,假如R3不是链烷酰基、链烯酰基或苯甲酰基,则R4也可以是脂肪族、环脂族或芳族二羧酸或二氨基甲酸的二价酰基,或能够是基团-CO-;或
R4是
其中T8和T9独立地是氢,1到18个碳原子的烷基,或T8和T9一起是4到6个碳原子的亚烷基或3-氧杂五亚甲基,例如T8和T9一起是3-氧杂五亚甲基;
当p是3时,
R4是2,4,6-三嗪基,
n是1或2,
当n是1时,
R5和R’5独立地是C1-C12烷基,C2-C12链烯基,C7-C12芳烷基,或R5也是氢,或R5和R’5一起是C2-C8亚烷基或羟基亚烷基或C4-C22酰氧基亚烷基;
当n是2时,
R5和R’5一起是(-CH2)2C(CH2-)2;
R6是氢,C1-C12烷基,烯丙基,苄基,缩水甘油基或C2-C6烷氧基烷基;
当n是1时,
R7是氢,C1-C12烷基,C3-C5链烯基,C7-C9芳烷基,C5-C7环烷基,C2-C4羟烷基,C2-C6烷氧基烷基,C6-C10芳基,缩水甘油基,式-(CH2)t-COO-Q或式-(CH2)t-O-CO-Q的基团,其中t是1或2,和Q是C1-C4烷基或苯基;或
当n是2时,
R7是C2-C12亚烷基,C6-C12亚芳基,基团-CH2CH(OH)-CH2-O-X-O-CH2-CH(OH)CH2-,其中X是C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基,或基团-CH2CH(OZ’)CH2-(OCH2-CH(OZ’)CH2)2-,其中Z’是氢、C1-C18烷基、烯丙基、苄基、C2-C12链烷酰基或苯甲酰基;
Q1是-N(R8)-或-O-;E7是C1-C3亚烷基,基团-CH2-CH(R9)-O-,其中R9是氢、甲基或苯基,基团-(CH2)3-NH-或直接的键;
R10是氢或C1-C18烷基,R8是氢,C1-C18烷基,C5-C7环烷基,C7-C12芳烷基,氰基乙基,C6-C10芳基,基团-CH2-CH(R9)-OH,其中R9具有以上给出的意义;以下结构式的基团
或以下结构式的基团
其中G4是C2-C6亚烷基或C6-C12亚芳基;或R8是基团-E7-CO-NH-CH2-OR10;
通式F表示聚合物的重复结构单元,其中T3是亚乙基或1,2-亚丙基,是从α-烯烃与烷基丙烯酸酯或甲基丙烯酸酯的共聚物(例如乙烯和丙烯酸乙酯的共聚物)衍生的重复结构单元,和其中k是2到100;
当p是1或2时T4具有与R4相同的意义,
T5是甲基,
T6是甲基或乙基,或T5和T6一起是四亚甲基或五亚甲基,例如T5和T6各自是甲基,
M和Y独立地是亚甲基或羰基,和当n是2时T4是亚乙基;
T7与R7相同,和当n是2时T7例如是八亚甲基,
T10和T11独立地是2到12个碳原子的亚烷基,或T11是
T12是哌嗪基,
-NR11-(CH2)d-NR11-或
其中R11与R3相同或也可以是
a、b和c独立地是2或3,和f是0或1,例如a和c各自是3,b是2和f是1;和
e是2,3或4,例如4;
T13与R2相同,前提条件是当n是1时T13不能是氢;
E1和E2,是不同的,各自是-CO-或-N(E5)-,其中E5是氢,C1-C12烷基或C4-C22烷氧基羰基烷基,例如E1是-CO-和E2是-N(E5)-,
E3是氢,1到30个碳原子的烷基,苯基,萘基,该苯基或该萘基被氯或被1到4个碳原子的烷基取代,或7到12个碳原子的苯基烷基,或被1到4个碳原子的烷基取代的该苯基烷基,
E4是氢,1到30个碳原子的烷基,苯基,萘基或7到12个碳原子的苯基烷基,或
E3和E4一起是4到17个碳原子的多亚甲基,或被至多四个具有1到4个碳原子的烷基例如甲基取代的该多亚甲基,
E6是脂肪族或芳族四价基团,
当m是1时式(N)的R2是前面所定义的基团;
G1是直接的键,C1-C12亚烷基,亚苯基或-NH-G’-NH,其中G’是C1-C12亚烷基;或
其中该位阻胺化合物是式I,II,III,IV,V,VI,VII,VIII,IX,X或XI的化合物
其中
E1,E2,E3和E4独立地是1到4个碳原子的烷基,或E1和E2独立地是1到4个碳原子的烷基和E3和E4连在一起是五亚甲基,或E1和E2;和E3和E4各连在一起是五亚甲基,
R1是1到18个碳原子的烷基,5到12个碳原子的环烷基,7到12个碳原子的二环或三环烃基团,7到15个碳原子的苯基烷基,6到10个碳原子的芳基或被一个至三个1到8个碳原子的烷基取代的该芳基,
R2是氢或1到12个碳原子的线性或支链烷基,
R3是1到8个碳原子的亚烷基,或R3是-CO-,-CO-R4-,-CONR2-或-CO-NR2-R4-,
R4是1到8个碳原子的亚烷基,
R5是氢,1到12个碳原子的线性或支链烷基,或
或当R4是亚乙基时,两个R5甲基取代基能够被直接的键连接,这样三嗪桥连基团-N(R5)-R4-N(R5)-是哌嗪-1,4-二基结构部分,
R6是2到8个碳原子的亚烷基或R6是
前提条件是,当R6是上述结构时Y不是-OH,
A是-O-或-NR7-,其中R7是氢,1到12个碳原子的直链或支链烷基,或R7是
T是苯氧基,被一个或两个1到4个碳原子的烷基、1到8个碳原子的烷氧基或-N(R2)2取代的苯氧基,前提条件是R2不是氢,或T是
X是-NH2,-NCO,-OH,-O-缩水甘油基,或-NHNH2,和
Y是-OH,-NH2,-NHR2(其中R2不是氢);或Y是-NCO,-COOH,环氧乙烷基(oxiranyl),-O-缩水甘油基,或-Si(OR2)3;或组合结构R3-Y-是-CH2CH(OH)R2,其中R2是烷基或被一个至四个氧原子***的该烷基,或R3-Y-是-CH2OR2;
或
其中该位阻胺化合物是N,N’,N_-三{2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚胺基二丙基胺;N,N’,N”-三{2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚胺基二丙基胺,和由通式I、II、IIA和III表述的桥接衍生物的混合物
R1NH-CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4 (I)
T-E1-T1 (II)
T-E1 (IIA)
G-E1-G1-E1-G2 (III)
其中在通式I的四胺中
R1和R2是s-三嗪结构部分E;和R3和R4中的一个是s-三嗪结构部分E,R3或R4中的另一个是氢,
E是
R是甲基,丙基,环己基或辛基,例如环己基,
R5是1到12个碳原子的烷基,例如正丁基,
其中在R是丙基、环己基或辛基的通式II或IIA的化合物中,
T和T1各自是被与通式I中相同定义的R1-R4取代的四胺,其中
(1)在各四胺中s-三嗪结构部分E的一个被基团E替代,它在两个四胺T和T1之间形成桥基,
E1是
或
(2)基团E1能够在与通式IIA中相同的四胺T中具有两个末端,其中四胺的E结构部分的两个都被一个E1基团替代,或
(3)四胺T的全部三个s-三嗪取代基能够是E1,这样一个E1连接T和T1和第二个E1具有在四胺T中的两个末端,
L是丙烷二基,环己烷二基或辛烷二基;
其中在通式III的化合物中
G,G1和G2各自是由与通式I中相同的R1-R4取代的四胺,只是G和G2各具有被E1替代的一个s-三嗪结构部分E,和G1具有被E1替代的两个三嗪结构部分E,这样在G和G1之间有桥基和在G1和G2之间有第二个桥基;
该混合物是通过两个到四个当量的2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与一个当量的N,N’-双(3-氨基丙基)乙二胺反应制备的;或该位阻胺是通式IIIb的化合物
其中该指数n是1到15;
R12是C2-C12亚烷基,C4-C12亚链烯基,C5-C7亚环烷基,C5-C7亚环烷基二(C1-C4亚烷基),C1-C4亚烷基二(C5-C7亚环烷基),亚苯基二(C1-C4亚烷基)或被1,4-哌嗪二基、-O-或>N-X1***的C4-C12亚烷基,其中X1是C1-C12酰基或(C1-C12烷氧基)羰基或具有下面给出的R14的定义中除氢以外的一种;或R12是以下结构式(Ib’)或(Ic’)的基团;
其中m是2或3,
X2是C1-C18烷基,未被取代的或被1、2或3个C1-C4烷基取代的C5-C12环烷基;未被取代的或被1、2或3个C1-C4烷基或C1-C4烷氧基取代的苯基,未被取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;和
该基团X3彼此独立地是C2-C12亚烷基;
R13,R14和R15,它们可以相同或不同,是氢,C1-C18烷基,未取代或被1、2或3个C1-C4烷基取代的C5-C12环烷基;C3-C18链烯基,未取代或被1、2或3个C1-C4烷基或C1-C4烷氧基取代的苯基;未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;四氢糠基或在2、3或4位上被-OH,C1-C8烷氧基,二(C1-C4烷基)氨基或下式(Ie’)的基团取代的C2-C4烷基;
其中Y是-O-;-CH2-;-CH2CH2-或>N-CH3,
或-N(R14)(R15)另外是式(Ie’)的基团;
基团A各自独立地是-OR13,-N(R14)(R15)或式(IIId)的基团;
X是-O-或>N-R16;
R16是氢,C1-C18烷基,C3-C18链烯基,未被取代的或被1、2或3个C1-C4烷基取代的C5-C12环烷基;未被取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;四氢化糠基,以下结构式(IIIf)的基团,
或在2、3和4位上被-OH取代的C2-C4烷基,C1-C8烷氧基,二(C1-C4烷基)氨基或以下结构式(Ie’)的基团;
R11具有对于R16给出的定义中的一种;和
该基团B彼此独立地具有对于A给出的定义中的一种。
烷基是直链或支链的和例如是甲基,乙基,正丙基,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,正十一基,正十二烷基,正十三烷基,正十四烷基,正十六烷基或正十八基。
环烷基包括环戊基和环己基;典型的环烯基包括环己烯基;而典型的芳烷基包括苄基,α-甲基-苄基,α,α-二甲基苄基或苯乙基,而典型的芳基包括例如苯基或萘基。
如果R2是羧酸的一价酰基,则它例如是乙酸,硬脂酸,水杨酸,苯甲酸或β-(3,5-二-叔丁基-4-羟苯基)丙酸的酰基。
如果R2是二羧酸的二价酰基,它例如是草酸,己二酸,琥珀酸,辛二酸,癸二酸,邻苯二甲酸,二丁基丙二酸,二苄基丙二酸或丁基-(3,5-二-叔丁基-4-羟基苄基)-丙二酸,或双环庚烯二羧酸的酰基,其中琥珀酸酯,癸二酸酯,邻苯二甲酸酯和间苯二酸酯是特定的例子。
如果R2是二氨基甲酸的二价酰基,例如是六亚甲基二氨基甲酸或2,4-亚甲苯基二氨基甲酸的酰基。
组分(i)的位阻烷氧基胺稳定剂是现有技术中公知的,也已知为N-烷氧基位阻胺和NOR位阻胺或NOR受阻胺光稳定剂或NOR HALS。
它们例如公开US专利No
5,004,770,5,204,473,5,096,950,5,300,544,5,112,890,5,124,378,5,145,893,5,216,156,5,844,026,6,117,995,6,271,377,6,392,041,6,376,584和6,472,456
US申请序列号09/714,717(2000年11月16日申请)和60/312,517(2001年8月15申请)。这些专利和申请的相关公开内容被引入这里供参考。
以上引用的US专利No 6,271,377,6,392,041和6,376,584公开了位阻羟基烷氧基胺稳定剂。对于本发明的目的,位阻羟基烷氧基胺稳定剂被认为是位阻烷氧基胺稳定剂的一个小组并且是本发明组分(i)的一部分。位阻羟基烷氧基胺也已知为N-羟基烷氧基位阻胺,或NORolHALS。
组分(i)的合适位阻胺包括例如:
NOR1 1-环己氧基-2,2,6,6-四甲基-4-十八烷基氨基哌啶;
NOR2双(1-辛基氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
NOR3 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-(2-羟乙基氨基)-s-三嗪;
NOR3双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
NOR4 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪;
NOR5 1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶;
NOR6 1-(2-羟基-2-甲基丙氧基)-4-氧代-2,2,6,6-四甲基哌啶;
NOR7 1-(2-羟基-2-甲基丙氧基)-4-十八烷酰基氧基-2,2,6,6-四甲基哌啶;
NOR8双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
NOR9双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
NOR10 2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟乙基氨基)-s-三嗪;
NOR11 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-双(3-氨基丙基)乙二胺)[CAS Reg.No.191680-81-6]的反应产物;和
NOR12以下通式的化合物
其中n是1到15。
化合物NOR12公开在US专利No.6,117,995的实施例2中。
组分(i)的位阻胺稳定剂理想地以基于聚乳酸聚合物基质的0.05%到20%(重量)的量,例如以0.1%到10%(重量);例如以0.2%到8%(重量);例如以0.5%到3%(重量)的量,包含在本发明的组合物中。例如,组分(i)的稳定剂是以基于聚乳酸基质重量的0.05%到15%,0.05%到10%,0.05%到8%,0.05%到5%或0.05%到3%(重量)的量存在。例如,组分(i)的稳定剂是以基于聚乳酸基质重量的0.1%到20%,0.2到20%,0.5到20%或1%到20%(重量)的量存在。
组分(ii)的普通阻燃剂
有机卤素阻燃剂例如是:
多溴化二苯醚(DE-60F,Great Lakes Corp.),
十溴二苯醚(DBDPO;SAYTEX_102E),
磷酸三[3-溴-2,2-双(溴甲基)丙基]酯(PB 370_,FMC 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,
双-(N,N’-羟基乙基)四氯亚苯基二胺,
聚-β-氯乙基三磷酸酯混合物,
四溴双酚A双(2,3-二溴丙基醚)(PE68),
溴化环氧树脂,
亚乙基-双(四溴邻苯二甲酰亚胺)(SAYTEX_BT-93),
双(六氯环戊二烯基)环辛烷(DECLORANE PLUS_),
氯化石蜡,
八溴二苯基醚,
六氯环戊二烯衍生物,
1,2-双(三溴苯氧基)乙烷(FF680),
四溴-双酚A(SATEX_RB100),
亚乙基双-(二溴-降冰片烷二羧酰亚胺)(SAYTEX_BN-451),
双-(六氯环戊二烯基)环辛烷,
聚四氟乙烯(PTFE),
异氰脲酸三-(2,3-二溴丙基)酯,和
亚乙基双-四溴邻苯二甲酰亚胺。
含磷的阻燃剂例如是:
四苯基间苯二酚二亚磷酸酯(FYROLFLEX_RDP,Akzo Nobel),
四(羟基甲基)磷鎓硫化物,
N,N-双(2-羟基乙基)-氨基甲基膦酸二乙基酯,
磷酸的羟烷基酯,
聚磷酸铵(APP)或(HOSTAFLAM_AP750),
间苯二酚二磷酸酯低聚物(RDP),
膦腈(phosphazene)阻燃剂,
乙二胺二磷酸酯(EDAP),
膦酸酯和它们的金属盐,以及
亚磷酸酯和它们的金属盐。
异氰脲酸酯阻燃剂包括多异氰脲酸酯,异氰脲酸的酯类和异氰脲酸酯类。例如,羟烷基异氰脲酸酯,如三-(2-羟乙基)异氰脲酸酯,三(羟甲基)异氰脲酸酯,三(3-羟基-正丙基)异氰脲酸酯或三缩水甘油基异氰脲酸酯。
蜜胺型阻燃剂例如是:
蜜胺氰脲酸酯,
蜜胺硼酸酯,
蜜胺磷酸酯,
蜜胺多磷酸酯,
蜜胺焦磷酸酯,
蜜胺铵多磷酸盐和
蜜胺铵焦磷酸盐。
硼酸可以包括为阻燃剂。
用于本发明中的卤代阻燃剂可以选自有机芳族卤代化合物,如卤代苯类,联苯类,酚类,它们的醚类或酯类,双酚类,二苯基醚类,芳族羧酸或多酸,它们的酸酐、酰胺或酰亚胺;有机环脂族或多环脂族卤代化合物;和有机脂肪族卤代化合物如卤化烷烃,低聚或聚合物,烷基磷酸酯或烷基异氰脲酸酯。这些组分在现有技术中基本上是已知的,参见例如US专利No4,579,906(例如3栏,30-41行),5,393,812;还参见Plastics Additives Handbook,Ed.by H.Zweifel,5th Ed.,HanserPubl.,Munich 2001,pp.681-698。
磷腈类阻燃剂是现有技术中为大家所熟知的。它们公开在例如EP1104766,JP07292233,DE19828541,DE1988536,JP11263885,US专利No 4,107,108,4,108,805和4,079,035和6,265,599中。US专利的相关公开内容因此被引入这里供参考。
PTFE,聚四氟乙烯(例如Teflon_6C;E.I.Du Pont),可以有利地被添加到本发明组合物中,作为附加的阻燃剂,如在US申请60/312,517(2001年8月15日申请)中所公开。
组分(ii)有利地以基于聚乳酸聚合物基质的0.5%到45%(重量),例如3%到40%,例如基于聚乳酸组分的5%到35%(重量),的量包含在本发明的组合物中。例如,组分(ii)是以0.5%到10%(重量),1%到10%,3%到10%或5%到10%(重量)的量使用,以聚乳酸聚合物基质的重量为基础。例如,组分(ii)是以0.5%到8%,从0.5%到6%,从0.5%到5%,或从0.5%到3%(重量)的量使用,以聚乳酸聚合物基质的重量为基础。
组分(i)与组分(ii)的比率(重量份)是例如在1∶5到1∶200之间,例如在1∶50到1∶100之间,或在1∶10到1∶25之间。例如组分(i)与组分(ii)的比率是1∶10到1∶200,1∶25到1∶200,1∶50到1∶200或1∶100到1∶200。例如,组分(i)与组分(ii)的重量比是1∶5至1∶100,从1∶5到1∶50,从1∶5到1∶25,或从1∶5到1∶10。
组分(ii)的用量也取决于具体的化合物的有效性和具体的应用类型。
本发明的组合物可以此外包括除酸剂。
除酸剂例如是水滑石和无定形的碱性碳酸铝镁,如描述在US专利No 4,427,816,5,106,898和5,234,981中的那些,它们的公开内容被引入这里供参考。水滑石又已知为hycite或DHT4A。
水滑石是自然的或合成的。自然水滑石被确认具有结构Mg6Al2(OH)16CO3·4H2O。
合成水滑石的典型经验式是Al2Mg4.35OH11.36CO3(1.67)·xH2O。
合成产物的实例包括:Mg0.7Al0.3(OH)2(CO3)0.15·0.54H2O,Mg4.5Al2(OH)13CO3·3.5H2O和Mg4.2Al(OH)12.4CO3。
除酸剂是例如以基于聚乳酸组分重量的0.1%到1.0%(重量)的量存在于聚乳酸聚合物组合物中。例如,该除酸剂是以基于聚乳酸组分的重量的0.2%至0.8%或0.4%至0.6%(重量)的量存在。例如,除酸剂是以基于聚乳酸组分重量的0.1%至0.8%,从0.1%至0.6%,从0.1%至0.4%或从0.1%至0.2%(重量)的量存在。例如,除酸剂是以基于聚乳酸组分重量的0.2%至1.0%,从0.4%到1.0%,从0.6%到1.0%或从0.8%到1.0%(重量)的量存在。
该除酸剂在颜色、气味和稳定性上有助于本发明组合物。
本发明聚合物组合物能够含有其它添加剂。这些附加添加剂主要地属于热稳定剂和/或光稳定剂。热稳定化包含加工和使用(长时间稳定性)。此类添加剂对于本领域中的技术人员是已知的并且它们中的多数是可从市场上买到的。
合适的附加添加剂例如是:
1.抗氧化剂
1.1.烷基化一元酚类,例如,2,6-二叔丁基-4-甲基苯酚,2-叔丁基-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)-4,6-二甲基苯酚,2,6-双十八烷基-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;侧链呈线性或支化的壬基苯酚类,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;以及它们的混合物。
1.2.烷基硫代甲基酚类,例如2,4-二辛基硫代甲基-6-叔丁基苯酚,2,4-二辛基硫代甲基-6-甲基苯酚,2,4-二辛基硫代甲基-6-乙基苯酚,2,6-双十二烷基硫代甲基-4-壬基苯酚。
1.3.氢醌类和烷基化氢醌类,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,硬脂酸3,5-二叔丁基-4-羟基苯基酯,己二酸双(3,5-二叔丁基-4-羟基苯基)酯。
1.4.生育酚,例如α-生育酚,β-生育酚,γ-生育酚,δ-生育酚和它们的混合物(维生素E)。
1.5.羟基化硫代二苯基醚类,例如,2,2’-硫代双(6-叔丁基-4-甲基苯酚),2,2’-硫代双(4-辛基苯酚),4,4’-硫代双(6-叔丁基-3-甲基苯酚),4,4’-硫代双(6-叔丁基-2-甲基苯酚),4,4’-硫代双(3,6-二仲戊基苯酚),4,4’-双(2,6-二甲基-4-羟基苯基)二硫醚。
1.6.亚烷基双酚类,例如,2,2’-亚甲基双(6-叔丁基-4-甲基苯酚),2,2’-亚甲基双(6-叔丁基-4-乙基苯酚),2,2’-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚],2,2’-亚甲基双(4-甲基-6-环己基苯酚),2,2’-亚甲基双(6-壬基-4-甲基苯酚),2,2’-亚甲基双(4,6-二叔丁基苯酚),2,2’-亚乙基双(4,6-二叔丁基苯酚),2,2’-亚乙基双(6-叔丁基-4-异丁基苯酚),2,2’-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2’-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4’-亚甲基双(2,6-二叔丁基苯酚),4,4’-亚甲基双(6-叔丁基-2-甲基苯酚),1,1’-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷,2,6-双(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-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷,双[3,3-双(3’-叔丁基-4’-羟基苯基)丁酸]乙二醇酯,双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯,对苯二甲酸双[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]酯,1,1-双-(3,5-二甲基-2-羟基苯基)丁烷,2,2-双-(3,5-二叔丁基-4-羟基苯基)丙烷,2,2-双-(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-苄基化合物类,例如3,5,3’,5’-四叔丁基-4,4’-二羟基二苄基醚,4-羟基-3,5-二甲基苄基巯基乙酸十八烷基酯,4-羟基-3,5-二叔丁基苄基巯基乙酸十三烷基酯,三(3,5-二叔丁基-4-羟基苄基)胺,二硫代对苯二甲酸双(4-叔丁基-3-羟基-2,6-二甲基苄基)酯,双(3,5-二叔丁基-4-羟基-苄基)硫醚,3,5-二叔丁基-4-羟基苄基巯基乙酸异辛基酯。
1.8.羟苄基化丙二酸酯类,例如,2,2-双-(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-双(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-双(3,5-二叔丁基-4-羟基苄基)丙二酸双[4-(1,1,3,3-四甲基丁基)苯基]酯。
1.9.芳族羟苄基化合物类,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯,1,4-双(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。
1.10.三嗪化合物类,例如2,4-双(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(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-2,6-二甲基苄基)-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.苄基膦酸酯类,例如2,5-二叔丁基-4-羟基苄基膦酸二甲酯,3,5-二叔丁基-4-羟基苄基膦酸二乙酯,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-羟基苄基膦酸的单乙酯的钙盐。
1.12.酰基氨基酚类,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-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酯类,构成酯基的是单羟基或多羟基醇类,例如甲醇,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,异氰脲酸三(羟基乙基)酯,N,N’-双(羟乙基)草酰胺,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。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸的酯类,构成酯基的是单羟基或多羟基醇类,例如甲醇,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,异氰脲酸三(羟基乙基)酯,N,N’-双(羟乙基)草酰胺,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。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸的酯类,构成酯基的是单羟基或多羟基醇类,例如甲醇,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,异氰脲酸三(羟基乙基)酯,N,N’-双(羟乙基)草酰胺,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。
1.16.3,5-二叔丁基-4-羟基苯基乙酸的酯类,构成酯基的是单羟基或多羟基醇类,例如甲醇,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,异氰脲酸三(羟基乙基)酯,N,N’-双(羟乙基)草酰胺,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。
1.17.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺类,例如N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺,N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺,N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼,N,N’-双[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺(Naugard_XL-1,由Uniroyal提供)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧化剂,例如N,N’-二异丙基-对-亚苯基二胺,N,N’-二仲丁基-对-亚苯基二胺,N,N’-双(1,4-二甲基戊基)-对-亚苯基二胺,N,N’-双(1-乙基-3-甲基戊基)-对-亚苯基二胺,N,N’-双(1-甲基庚基)-对亚苯基二胺,N,N’-二环己基-对亚苯基二胺,N,N’-二苯基-对-亚苯基二胺,N,N’-双(2-萘基)-对-亚苯基二胺,N-异丙基-N’-苯基-对-亚苯基二胺,N-(1,3-二甲基丁基)-N’-苯基-对-亚苯基二胺,N-(1-甲基庚基)-N’-苯基-对-亚苯基二胺,N-环己基-N’-苯基-对-亚苯基二胺,4-(对甲苯氨磺酰基)二苯胺,N,N’-二甲基-N,N’-二仲丁基-对亚苯基二胺,二苯胺,N-烯丙基二苯胺,4-异丙氧基-二苯胺,N-苯基-1-萘基胺,N-(4-叔辛基苯基)-1-萘基胺,N-苯基-2-萘基胺,辛基化二苯胺(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,4-十二酰氨基苯酚,4-十八酰氨基苯酚,双(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-双[(2-甲基苯基)氨基]乙烷,1,2-双(苯基氨基)丙烷,(邻甲苯基)双胍,双[4-(1’,3’-二甲基丁基)苯基]胺,叔辛基化N-苯基-1-萘基胺,单和二烷基化叔丁基/叔辛基二苯基胺类的混合物,单和二烷基化壬基二苯基胺类的混合物,单和二烷基化十二烷基二苯基胺类的混合物,单和二烷基化异丙基/异己基二苯基胺类的混合物,单和二烷基化叔丁基二苯基胺类的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,单和二烷基化叔丁基/叔辛基吩噻嗪的混合物,单和二烷基化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-双(2,2,6,6-四甲基-哌啶-4-基)-六亚甲基二胺,双(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***类,例如公开在US专利No.
3,004,896;3,055,896;3,072,585;3,074,910;3,189,615;3,218,332;3,230,194;4,127,586;4,226,763;4,275,004;4,278,589;4,315,848;4,347,180;4,383,863;4,675,352;4,681,905,4,853,471;5,268,450;5,278,314;5,280,124;5,319,091;5,410,071;5,436,349;5,516,914;5,554,760;5,563,242;5,574,166;5,607,987,5,977,219和6,166,218中公开的已知商购羟苯基-2H-苯并***类和苯并***类,如2-(2-羟基-5-甲基苯基)-2H-苯并***,2-(3,5-二叔丁基-2-羟基苯基)-2H-苯并***,2-(2-羟基-5-叔丁基苯基)-2H-苯并***,2-(2-羟基-5-叔辛基苯基)-2H-苯并***,5-氯-2-(3,5-二叔丁基-2-羟基苯基)-2H-苯并***,5-氯-2-(3-叔丁基-2-羟基-5-甲基苯基)-2H-苯并***,2-(3-仲丁基-5-叔丁基-2-羟基苯基)-2H-苯并***,2-(2-羟基-4-辛氧基苯基)-2H-苯并***,2-(3,5-二叔戊基-2-羟基苯基)-2H-苯并***,2-(3,5-双-α-枯基-2-羟基苯基)-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-(ω-羟基)-八(亚乙基氧基)羰基-乙基)-,苯基)-2H-苯并***,2-(3-十二烷基-2-羟基-5-甲基苯基)-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-辛氧基羰基)乙基苯基)-2H-苯并***,十二烷基化2-(2-羟基-5-甲基苯基)-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-辛基氧基羰基乙基)苯基)-5-氯-2H-苯并***,2-(3-叔丁基-5-(2-(2-乙基己基氧基)-羰基乙基)-2-羟基苯基)-5-氯-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-5-氯-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-2H-苯并***,2-(3-叔丁基-5-(2-(2-乙基己基氧基)羰基乙基)-2-羟基苯基)-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-异辛基氧基羰基乙基)苯基)-2H-苯并***,2,2’-亚甲基-双[4-叔辛基-(6-2H-苯并***-2-基)苯酚),2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并***,2-(2-羟基-3-叔辛基-5-α-枯基苯基)-2H-苯并***,5-氟-2-(2-羟基-3,5-二-α-基-苯基)-2H-苯并***,5-氯-2-(2-羟基-3,5-二-α-枯基-基)-2H-苯并***,5-氯-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并***,2-(3-叔丁基-2-羟基-5-(2-异辛基氧基羰基乙基)苯基)-5-氯-2H-苯并***,5-三氟甲基-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并***,5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并***,5-三氟甲基-2-(2-羟基-3,5-二叔辛基苯基)-2H-苯并***,-(5-三氟甲基-2H-苯并***-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲基酯,5-丁基磺酰基-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并***,5-三氟基-2-(2-羟基-3-α-枯基-5-叔丁基苯基)-2H-苯并***,5-三氟甲基-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***,5-三氟甲基-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并***,5-丁基磺酰基-2-(2-基-3,5-二叔丁基苯基)-2H-苯并***,和5-苯基磺酰基-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***。
2.2.2-羟基二苯甲酮类,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’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。
2.3.取代的和未取代的苯甲酸的酯类,例如水杨酸4-叔丁基-苯基酯,水杨酸苯酯,水杨酸辛基苯酯,二苯甲酰基间二酚,双(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.丙烯酸酯类,例如α-氰基-β,β-二苯基丙烯酸乙酯,α-氰基-β,β-二苯基丙烯酸异辛酯,α-甲酯基肉桂酸甲酯,α-氰基-β-甲基-对甲氧基肉桂酸甲酯,α-氰基-β-甲基-对甲氧基肉桂酸丁酯,α-甲酯基-对甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物类,例如2,2’-硫代-双-[4-(1,1,3,3-四甲基-丁基)苯酚]的镍配合物,如1∶1或1∶2配合比,有或没有附加的配位体如正丁基胺,三乙醇胺或N-环己基二乙醇胺,二丁基二硫代氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯(例如甲酯或乙酯)类的镍盐,酮肟例如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物类,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,有或没有附加的配位体。
2.6.空间位阻胺;例如癸二酸双(2,2,6,6-四甲基-4-哌啶基)酯,琥珀酸双(2,2,6,6-四甲基-4-哌啶基)酯,癸二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯,癸二酸双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)酯,双(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基,6-二氯-1,3,5-三嗪的线性或环状缩合物,次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯,1,2,3,4-丁烷四羧酸四(2,2,6,6-四甲基-4-哌啶基)酯,1,1’-(1,2-亚乙基)双(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,2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸双(1,2,2,6,6-五甲基哌啶基)酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,癸二双(1-辛氧基-2,2,6,6-四甲基哌啶基)酯,丁二酸双(1-辛氧基-2,2,6,6-四甲基哌啶基)酯,N,N’-双-(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的线性或环状缩合物,2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物,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-双(3-氨基丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-啶基)吡咯烷-2,5-二酮,3-二基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮,4-十烷氧基-2,2,6,6-四甲基哌啶和4-硬脂氧基-2,2,6,6-四甲基哌啶的混合物,N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合产物,1,2-双(3-氨基-丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合物,以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);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,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[4.5]癸烷和表氯醇的反应产物,1,1-双(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)乙烯,N,N’-双甲酰基-N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺,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,马来酸酐-α-烯烃共聚物与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.草酰胺类,例如4,4’二辛氧基-N,N’-草酰二苯胺,2,2’-二乙氧基-N,N’-草酰二苯胺,2,2’-二辛氧基-5,5’-二叔丁基-N,N’-草酰二苯胺(2,2’-dioctyloxy-5,5’-di-tert-butoxanilide),2,2’-二(十二烷氧基)-5,5’-二叔丁基-N,N’-草酰二苯胺,2-乙氧基-2’-乙基-N,N’-草酰二苯胺,N,N’-双(3-二甲氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2’-乙氧基-N,N’-草酰二苯胺和它与2-乙氧基-2’-乙基-5,4’-二叔丁氧基N,N’-草酰二苯胺的混合物以及邻-和对-甲氧基双取代的N,N’-草酰二苯胺类的混合物和邻-和对-乙氧基-二取代的N,N’草酰二苯胺类的混合物。
2.8.2-(2-羟基苯基)-1,3,5-三嗪类,例如公开在WO 96/28431和美国专利No.
3,843,371;4,619,956;4,740,542;5,096,489;5,106,891;5,298,067;5,300,414;5,354,794;5,461,151;5,476,937;5,489,503;5,543,518;5,556,973;5,597,854;5,681,955;5,726,309;5,736,597;5,942,626;5,959,008;5,998,116;6,013,704;6,060,543;6,187,919;6,242,598和6,255,483中的已知商购三-芳基-邻-羟基苯基-s-三嗪和三嗪,4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-辛基氧基苯基)-s-三嗪,Cyasorb_1164,CytecCorp,4,6-双-(2,4-二甲基苯基)-2-(2,4-二羟基苯基)-s-三嗪,2,4-双-(2,4-二甲基苯基)-6-(4-氯苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(2,4-二甲基苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-溴苯基)-s-三嗪,2,4-双[2-羟基-4-(2-乙酰氧基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-双(2,4-二羟基苯基)-6-(2,4-二甲基苯基)-s-三嗪,2,4-双(4-联苯基)-6-(2-羟基-4-辛基氧基羰基乙叉基氧基苯基)-s-三嗪,2-苯基-4-[2-羟基-4-(3-仲丁氧基-2-羟基丙氧基)苯基]-6-[2-羟基-4-(3-仲戊基氧基-2-羟基丙氧基)-苯基]-s-三嗪,2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(3-苄基氧基-2-羟基-丙氧基)苯基]-s-三嗪,2,4-双(2-羟基-4-正丁氧基苯基)-6-(2,4-二正丁基氧基苯基)-s-三嗪,2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(3-壬基氧基*-2-羟基-丙氧基)-5-α-枯基苯基]-s-三嗪(*表示辛基氧基、壬基氧基和癸基氧基的混合物),亚甲基双-{2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(3-丁基氧基-2-羟基丙氧基)苯基]-s-三嗪},按5∶4∶1比率的在3∶5’、5∶5’和3∶3’位上桥接的亚甲基桥接二聚物混合物,2,4,6-三(2-羟基-4-异辛基氧基羰基异丙叉基-氧基苯基)-s-三嗪,2,4-双(2,4-二甲基苯基)-6-(2-羟基-4-己基氧基-5-α-枯基-苯基)-s-三嗪,2-(2,4,6-三甲基苯基)-4,6-双[2-羟基-4-(3-丁基氧基-2-羟基-丙基氧基)苯基]-s-三嗪,2,4,6-三[2-羟基-4-(3-仲丁基氧基-2-羟基丙基氧基)-苯基]-s-三嗪,4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十二烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪和4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十三烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪的混合物,Tinuvin_400,Ciba Specialty ChemicalsCorp.,4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-(2-乙基己基氧基)-2-羟基丙氧基)-苯基)-s-三嗪和4,6-二苯基-2-(4-己基氧基-2-羟基苯基)-s-三嗪。
3.金属减活剂类,例如N,N’-二苯基草酰胺,N-水杨醛-N’-水杨酰基肼,N,N’-双(水杨酰基)肼,N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰基氨基-1,2,4-***,双(苄叉基)草酰二肼,N,N’-草酰二苯胺,间苯二甲酰二肼,癸二酰双(苯基肼),N,N’-二乙酰基己二酰二肼,N,N’-双(水杨酰基)草酰二肼,N,N’-双(水杨酰基)硫代丙酰基二肼。
4.亚磷酸酯类和亚膦酸酯类,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,二亚磷酸二硬脂基季戊四醇酯,亚磷酸三(2,4-二叔丁基苯基)酯,二亚磷酸二异癸基季戊四醇酯,二亚磷酸双(2,4-二叔丁基苯基)季戊四醇酯,二亚磷酸双(2,6-二叔丁基-4-甲基苯基)-季戊四醇酯,二亚磷酸二异癸基氧基季戊四醇酯,二亚磷酸双(2,4-二叔丁基-6-甲基苯基)季戊四醇酯,二亚磷酸双(2,4,6-三叔丁基苯基)季戊四醇酯,三亚磷酸三硬脂基山梨糖醇酯,二亚膦酸四(2,4-二叔丁基苯基)4,4’-亚联苯基酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-dioxaphosphocin,6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-dioxaphosphocin,亚磷酸双(2,4-二叔丁基-6-甲基苯基)甲基酯,亚磷酸双(2,4-二叔丁基-6-甲基苯基)乙基酯,2,2’,2″-次氮基[三乙基三(3,3’,5,5’-四叔丁基-1,1’-二苯基-2,2’-二基)亚磷酸酯],亚磷酸2-乙基己基(3,3’,5,5’-四叔丁基-1,1’-联苯基-2,2’-二基)酯。
具体实例是以下亚磷酸酯:
亚磷酸三(2,4-二叔丁基苯基)酯(Irgafos_168,Ciba-Geigy),亚磷酸三(壬基苯基)酯,
5.羟基胺类,例如N,N-二苄基羟基胺,N,N-二乙基羟基胺,N,N-二辛基羟基胺,N,N-二月桂基羟基胺,N,N-二(十四烷基)羟基胺,N,N-二(十六烷基)羟基胺,N,N-二(十八烷基)羟基胺,N-十六烷基-N-十八烷基羟基胺,N-十七烷基-N-十八烷基羟基胺,由氢化牛油脂肪胺得到的N,N-二烷基羟基胺。
6.硝酮类,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,由氢化牛油脂肪胺衍生而来的N,N-二烷基羟基胺获得的硝酮。
7.硫代增效剂,例如硫代二丙酸二月桂基酯或硫代二丙酸二硬脂基酯。
8.过氧化物清除剂,例如β-硫代二丙酸的酯类,例如月桂基、硬脂基、十四烷基或十三烷基酯类,巯基苯并咪唑或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)二硫醚,四(β-十二烷基巯基)丙酸季戊四醇酯。
9.聚酰胺稳定剂,例如铜盐与碘化物和/或磷化合物的混合物,和二价锰的盐。
10.碱性助稳定剂,例如三聚氰胺,聚乙烯基吡咯烷酮,双氰胺,三烯丙基氰脲酸酯,脲衍生物,肼衍生物,胺类,聚酰胺类,聚氨酯类,高级脂肪酸的碱金属盐和碱土金属盐,例如硬脂酸钙,硬脂酸锌,二十二烷酸镁,硬脂酸镁,蓖麻酸钠和棕榈酸钾,邻苯二酚锑或邻苯二酚锌。
11.成核剂类,例如,无机物质,如滑石,金属氧化物类如二氧化钛或氧化镁,优选碱土金属的磷酸盐、碳酸盐或硫酸盐;有机化合物如单或多羧酸类和它们的盐类,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;聚合化合物如离子共聚物(“离聚物”)。
12.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,玻璃泡,石棉,滑石,高岭土,云母,硫酸钡,金属氧化物和氢氧化物,炭黑,石墨,木粉和其它天然产物的粉末或纤维,合成纤维。
13.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,流变添加剂,催化剂,流动控制剂,荧光增白剂,阻燃剂,抗静电剂和发泡剂。
14.苯并呋喃酮类(benzofuranones)和二氢吲哚酮类,例如在US-A-4,325,863,US-A-4,338,244,US-A-5,175,312,US-A-5,216,052,US-A-5,252,643,DE-A-4,316,611,DE-A-4,316,622,DE-A-4,316,876;EP-A-0589839或EP-A-0591102中公开的那些,或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-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮,3,3’-双[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。
合适润滑剂例如是:
褐煤蜡,脂肪酸酯,PE蜡,酰胺蜡,多元醇偏酯,部分地皂化PE蜡,所谓的复酯氯化石蜡,甘油酯,碱土金属皂或脂肪酮,如在DE4204887中所述。合适润滑剂也描述在“Taschenbuch derKunststoffadditive”,编辑者R.Gachter和H.Muller,Hanser Verlag,第三版,1990,第443-503页。其它润滑剂实例,尤其润滑剂的结合物,可以在EP 0062813和EP 0336289中找到。
本发明组合物能够另外含有选自s-三嗪,草酰替苯胺,羟基二苯甲酮,苯甲酸酯和α-氰基丙烯酸酯中的另一种UV吸收剂。特别地,本发明组合物可以另外含有有效稳定量的至少一种其它2-羟苯基-2H-苯并***;另一种三-芳基-s-三嗪;或位阻胺或它们的混合物。例如,附加组分选自颜料,染料,增塑剂,抗氧化剂,触变剂,流平助剂,碱性助稳定剂,其它光稳定剂像UV吸收剂和/或位阻胺,金属减活剂,金属氧化物,有机磷化合物,羟胺,和它们的混合物,尤其颜料,酚类抗氧剂,硬脂酸钙,硬脂酸锌,亚磷酸酯和亚膦酸酯稳定剂,苯并呋喃酮稳定剂,2-(2’-羟苯基)苯并***和2-(2-羟苯基)-1,3,5-三嗪类型的UV吸收剂,和位阻胺。
本发明的组合物可以通过已知的方法,例如通过使用诸如压延机、混合器、捏合机、挤出机等之类的设备将所列举的添加剂和任选的其它添加剂与聚合物混合,来制备。该添加剂能够单独添加或作为彼此的掺混物添加。还有可能使用母料。对于母料,该载体聚合物不一定是聚乳酸聚合物。在此类操作中,载体聚合物能够以粉末,粒料,溶液,悬浮液的形式或以乳胶的形式使用。
本发明的阻燃整理的聚合物可通过已知方法制成所需形式。此类方法是,例如,压延,挤出,喷涂,旋转,压缩熔化,旋转铸塑法,热成形或挤坯吹塑。阻燃整理的聚合物也可以加工成泡沫制品。
整理过的阻燃性聚乳酸聚合物制品用于例如纤维,膜,模制品和泡沫制品。
本发明的添加剂和任选的其它组分单独或彼此混合被添加到聚合物材料中。如果需要,各组分能够在被引入到聚合物中之前彼此混合,例如通过干混合,压缩或以熔体形式。
此外,本发明涉及为聚乳酸聚合物基质赋予光稳定性和阻燃性的方法,该方法包括向该聚合物基质中添加下面组分的协同混合物:
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺型阻燃剂中的至少一种普通阻燃剂。
通过在其中引入下面组分的协同混合物赋予阻燃性的模塑聚乳酸聚合物制品
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺型阻燃剂中的至少一种普通阻燃剂,
是本发明的另一个主题。
理想的是模塑的聚乳酸聚合物制品,其中该组分(i)选自如上所述的合适位阻胺。
也理想的是模塑的聚乳酸聚合物制品,其中该组分(ii)选自如上所述的普通阻燃剂。
还考虑到,PTFE,聚四氟乙烯(例如Teflon_6C;E.I.Du Pont),可以有利地被添加到本发明组合物中,作为附加的阻燃剂,如在US申请60/312,517(2001年8月15日申请)中所公开。
组分(i)和(ii)的有效阻燃量是显示由通过用于评价阻燃性的标准方法之一测定的阻燃效力所需的量。它们包括Fire Tests for Flame-Resistant Textiles and Films的NFPA 701标准方法,1989和1996版;the UL 94 Test for Flammability of Plastic Materials for Parts inDevices and Appliances,第5版,1996年10月29日;限氧指数(LOI),ASTM D-2863;和Cone Calorimetry,ASTM E-1354。根据the UL 94V试验的评级按照下表来进行:
评级 | 余焰时间 | 燃烧液滴 | 燃烧至夹具 |
V-0 | <10s | 无 | 无 |
V-1 | <30s | 无 | 无 |
V-2 | <30s | 有 | 无 |
失败 | <30s | 有 | |
失败 | >30s | 无 |
发现与组分(i)和(ii)的本发明结合物在阻燃剂组合物中一起使用特别有效的辅助添加剂如下所示:
UV吸收剂:
2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并***,(TINUVIN_234,CibaSpecialty Chemicals Corp.);
2-(2-羟基-5-甲基苯基)-2H-苯并***,(TINUVIN_P,CibaSpecialty Chemicals Corp.);
5-氯-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***,(TINUVIN_327,Ciba Specialty Chemicals Corp.);
2-(2-羟基-3,5-二-叔戊基苯基)-2H-苯并***,(TINUVIN_328,Ciba Specialty Chemicals Corp.);
2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并***,(TINUVIN_928,Ciba Specialty Chemicals Corp.);
3,5-二叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯基酯,(TINUVIN_120,Ciba Specialty Chemicals Corp.);
2-羟基-4-正辛氧基二苯甲酮,(CHIMASSORSB_81,CibaSpecialty Chemicals Corp.);
2,4-双(2,4-二甲基苯基)-6-(2-羟基-4-辛氧基苯基)-s-三嗪,(CYASORB_1164,Cytec)。
以下实施例仅用于举例说明的目的,决不构成对本发明的范围的限制。所给出的室温表示20-25℃的温度。百分率按聚合物基材的重量计,除非另有规定。
缩写:
v 体积份
w 重量份
1Hnmr 1H的核磁共振(NMR)
m/z 质谱(原子单位)
amu 分子量,g/mol(原子单位)
PLA 聚乳酸
试验方法
Fire Tests for Flame-Resistant Textiles and Films的NFPA 701标准方法,1989和1996版;
UL 94Test for Flammability of Plastic Materials for Parts inDevices and Appliances,第5版,1996年10月29日;
限氧指数(LOI),ASTM D-2863;
Cone Calorimetry,ASTM E-1或ASTM E-1354;
ASTM D2633-82,燃烧试验。
试验化合物
本发明组分(i)的位阻胺:
NOR1 1-环己氧基-2,2,6,6-四甲基-4-十八烷基氨基哌啶;
NOR2双(1-辛基氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
NOR3 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-(2-羟乙基氨基)-s-三嗪;
NOR3双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
NOR4 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪;
NOR5 1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶;
NOR6 1-(2-羟基-2-甲基丙氧基)-4-氧代-2,2,6,6-四甲基哌啶;
NOR7 1-(2-羟基-2-甲基丙氧基)-4-十八烷酰基氧基-2,2,6,6-四甲基哌啶;
NOR8双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
NOR9双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
NOR10 2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟乙基氨基)-s-三嗪;
NOR11 2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-双(3-氨基丙基)乙二胺)[CAS Reg.No.191680-81-6]的反应产物;
NOR11表示为化合物与下式的主要组分的混合物
R1NH-CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4
其中R1、R2、R3和R4中的3个是下式的残基
以及R1、R2、R3和R4中的一个是氢
(NOR11是公开在US专利No.5,844,026的实施例3中的高分子量化合物);和
NOR12是以下通式的化合物
其中n是1到15。
组分(ii)的普通阻燃剂:
DBDPO是十溴二苯基醚,
FR1三[3-溴-2,2-双(溴甲基)丙基]磷酸酯,(PB370?,FMC Corp.),
FR2聚磷酸铵(APP),
FR3四溴双酚A双(2,3-二溴丙基醚)(PE68),
FR4聚磷酸铵/增效剂共混物,HOSTAFLAM_AP750,
FR5十溴二苯基醚(DBDPO;从Dead Sea Bromine获得),
FR6亚乙基双-(四溴邻苯二甲酰亚胺),(SAYTEX_BT-93),
FR7蜜胺磷酸盐,MELAPUR_P46,
FR8聚磷酸铵,EXOLIT_AP752,
FR9三-(2,3-二溴丙基)-异氰脲酸酯,
FR10六溴环十二烷,
FR11蜜胺氰尿酸盐,MELAPUR_MC,
FR12蜜胺硼酸盐,
FR13蜜胺聚磷酸盐MELAPUR_200和
FR14蜜胺焦磷酸盐。
化合物NOR2,NOR7,NOR11,NOR12是从Ciba SpecialtyChemicals商购的稳定剂。MELAPUR产品是从Ciba SpecialtyChemicals商购的。
实施例1
聚乳酸聚合物树脂通过使用Turbula混合器与试验添加剂混合15-20分钟。总配制大小是1000g。混合物然后用27mm Leistritz双螺杆挤出机在160-190℃下挤出。所获得的树脂用切刀造粒。
化合物粒料然后注射塑模成5”×0.5”×0.125”条形。阻燃性由UL 94试验测量。结果在下面给出。添加剂是基于总配制剂的wt%。进行两组的试验。
NOR11 | FR1 | FR5 | 评级 |
----0.250.51.0----------------1.00.250.25 | ----------------510--------510---- | ------------------------510--------10 | 失败失败V2失败失败V2V2V2V0V0V0 |
NOR11 | FR1 | FR5 | 评级 |
----0.250.51.0----------------0.50.5 | ----------------5------------5---- | --------------------2.55.010----10 | 失败失败失败V2V2失败V2V2V0V0 |
本发明位阻胺和普通阻燃剂的阻燃性结合物在聚乳酸中具有协同作用。
NOR11可以用选自NOR1-NOR10和NOR12中的一种或多种位阻胺替换。FR1和FR5可以被选自FR2-FR4和FR6-FR14中的一种或多种阻燃剂替代。
Claims (14)
1.阻燃性聚乳酸聚合物组合物,它包括聚乳酸聚合物基质和下面组分的协同混合物:
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺基阻燃剂中的至少一种普通阻燃剂。
2.根据权利要求1的组合物,其中组分(i)的稳定剂具有下式
其中
G1和G2独立地是具有1到8个碳原子的烷基或一起是五亚甲基,
Z1和Z2各自是甲基,或Z1和Z2一起形成连接用结构部分,它可以另外被酯,醚,酰胺,氨基,羧基或尿烷基团取代,和
E是氧基,羟基,烷氧基,环烷氧基,芳烷氧基,芳氧基,-O-CO-OZ3,-O-Si(Z4)3,-O-PO(OZ5)2或-O-CH2-OZ6,其中Z3,Z4,Z5和Z6选自氢,脂肪族,芳脂族和芳族结构部分;或E是-O-T-(OH)b,
T是具有1到18个碳原子的直链或支链亚烷基,具有5到18个碳原子的亚环烷基,具有5到18个碳原子的亚环链烯基,被苯基或被一个或两个1-4个碳原子的烷基取代的苯基所取代的具有1-4个碳原子的直链或支链亚烷基;
b是1,2或3,前提条件是b不能超过在T中的碳原子的数量,并且当b是2或3时,各羟基连接于T的不同碳原子上。
3.根据权利要求1的组合物,其中组分(i)的稳定剂具有下式A-R
其中
E是氧基,羟基,具有1到18个碳原子的烷氧基,具有5到12个碳原子的环烷氧基或具有7到15个碳原子的芳烷氧基,或E是-O-T-(OH)b,
T是具有1到18个碳原子的直链或支链亚烷基,具有5到18个碳原子的亚环烷基,具有5到18个碳原子的亚环链烯基,被苯基或被一个或两个1-4个碳原子的烷基取代的苯基所取代的具有1-4个碳原子的直链或支链亚烷基;
b是1,2或3,前提条件是b不能超过在T中的碳原子的数量,并且当b是2或3时,各羟基连接于T的不同碳原子上;
R是氢或甲基,
m是1到4,
当m是1时,
R2是氢,C1-C18烷基或该烷基任选被一个或多个氧原子***,C2-C12链烯基,C6-C10芳基,C7-C18芳烷基,缩水甘油基,脂肪族、环脂族或芳族羧酸的或氨基甲酸的一价酰基,具有5-12个C原子的环脂族羧酸或具有7-15个C原子的芳族羧酸的酰基,或
其中x是0或1,
其中y是2-4;
当m是2时,
R2是C1-C12亚烷基,C4-C12亚链烯基,亚二甲苯基,脂肪族、环脂族、芳脂族或芳族二羧酸的或二氨基甲酸的二价酰基,具有2-18个C原子的脂族二羧酸,具有8-14个C原子的环脂族或芳族的二羧酸,或具有8-14个C原子的脂肪族、环脂族或芳族的二氨基甲酸的酰基;
其中D1和D2独立地是氢,含有至多8个碳原子的烷基,芳基或芳烷基基团(包括3,5-二叔丁基-4-羟基苄基),D3是氢,或含有至多18个碳原子的烷基或链烯基,和d是0-20;
当m是3时,R2是脂肪族、不饱和脂肪族、环脂族或芳族三羧酸的三价酰基;
当m是4时,R2是饱和或不饱和脂肪族或芳族四羧酸类的四价酰基,该四羧酸类包括1,2,3,4-丁烷四羧酸,1,2,3,4-丁-2-烯四羧酸,以及1,2,3,5-和1,2,4,5-戊烷四羧酸;
p是1,2或3,
R3是氢,C1-C12烷基,C5-C7环烷基,C7-C9芳烷基,C2-C18链烷酰基,C3-C5链烯酰基或苯甲酰基;
当p是1时,
R4是氢,未被取代的或被氰基、羰基或脲基取代的C1-C18烷基、C5-C7环烷基、C2-C8链烯基,芳基,芳烷基,或它是缩水甘油基,式-CH2-CH(OH)-Z或式-CO-Z或-CONH-Z的基团,其中Z是氢、甲基或苯基;或以下结构式的基团
或
其中h是0或1,
R3和R4一起,当p是1时,能够是4到6个碳原子的亚烷基或2-氧代多亚烷基,脂肪族或芳族1,2-或1,3-二羧酸的环状酰基,
当p是2时,
R4是直接的键或是C1-C12亚烷基,C6-C12亚芳基,亚二甲苯基,-CH2CH(OH)-CH2基团或基团-CH2-CH(OH)-CH2-O-X-O-CH2-CH(OH)-CH2-,其中X是C2-C10亚烷基,C6-C15亚芳基或C6-C12亚环烷基;或,假如R3不是链烷酰基、链烯酰基或苯甲酰基,则R4也可以是脂肪族、环脂族或芳族的二羧酸或二氨基甲酸的二价酰基,或能够是基团-CO-;或
R4是
其中T8和T9独立地是氢,1到18个碳原子的烷基,或T8和T9一起是4到6个碳原子的亚烷基或3-氧杂五亚甲基;
当p是3时,
R4是2,4,6-三嗪基,
n是1或2,
当n是1时,
R5和R’5独立地是C1-C12烷基,C2-C12链烯基,C7-C12芳烷基,或R5也是氢,或R5和R’5一起是C2-C8亚烷基或羟基亚烷基或C4-C22酰氧基亚烷基;
当n是2时,
R5和R’5一起是(-CH2)2C(CH2-)2;
R6是氢,C1-C12烷基,烯丙基,苄基,缩水甘油基或C2-C6烷氧基烷基;
当n是1时,
R7是氢,C1-C12烷基,C3-C5链烯基,C7-C9芳烷基,C5-C7环烷基,C2-C4羟烷基,C2-C6烷氧基烷基,C6-C10芳基,缩水甘油基,式-(CH2)t-COO-Q或式-(CH2)t-O-CO-Q的基团,其中t是1或2,和Q是C1-C4烷基或苯基;或
当n是2时,
R7是C2-C12亚烷基,C6-C12亚芳基,基团-CH2CH(OH)-CH2-O-X-O-CH2-CH(OH)CH2-,其中X是C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基,或基团-CH2CH(OZ’)CH2-(OCH2-CH(OZ’)CH2)2-,其中Z’是氢、C1-C18烷基、烯丙基、苄基、C2-C12链烷酰基或苯甲酰基;
Q1是-N(R8)-或-O-;E7是C1-C3亚烷基,基团-CH2-CH(R9)-O-,其中R9是氢、甲基或苯基,基团-(CH2)3-NH-或直接的键;
R10是氢或C1-C18烷基,R8是氢,C1-C18烷基,C5-C7环烷基,C7-C12芳烷基,氰基乙基,C6-C10芳基,基团-CH2-CH(R9)-OH,其中R9具有以上给出的意义;以下结构式的基团
或以下结构式的基团
其中G4是C2-C6亚烷基或C6-C12亚芳基;或R8是基团-E7-CO-NH-CH2-OR10;
通式F表示聚合物的重复结构单元,其中T3是亚乙基或1,2-亚丙基,是从α-烯烃与烷基丙烯酸酯或甲基丙烯酸酯的共聚物衍生的重复结构单元,和其中k是2到100;
当p是1或2时T4具有与R4相同的意义,
T5是甲基,
T6是甲基或乙基,或T5和T6一起是四亚甲基或五亚甲基,
M和Y独立地是亚甲基或羰基,和当n是2时T4是亚乙基;
T7与R7相同,
T10和T11独立地是2到12个碳原子的亚烷基,或T11是
T12是哌嗪基,
其中R11与R3相同或也可以是
a、b和c独立地是2或3,和f是0或1;和
e是2,3或4;
T13与R2相同,前提条件是当n是1时T13不能是氢;
E1和E2,是不同的,各自是-CO-或-N(E5)-,其中E5是氢,C1-C12烷基或C4-C22烷氧基羰基烷基,
E3是氢,1到30个碳原子的烷基,苯基,萘基,该苯基或该萘基被氯或被1到4个碳原子的烷基取代,或7到12个碳原子的苯基烷基,或被1到4个碳原子的烷基取代的该苯基烷基,
E4是氢,1到30个碳原子的烷基,苯基,萘基或7到12个碳原子的苯基烷基,或
E3和E4一起是4到17个碳原子的多亚甲基,或被至多四个具有1到4个碳原子的烷基取代的该多亚甲基,
E6是脂肪族或芳族四价基团,
当m是1时式(N)的R2是前面所定义的基团;
G1是直接的键,C1-C12亚烷基,亚苯基或-NH-G’-NH,其中G’是C1-C12亚烷基;或
其中该位阻胺化合物是式I,II,III,IV,V,VI,VII,VIII,IX,X或XI的化合物
其中
E1,E2,E3和E4独立地是1到4个碳原子的烷基,或E1和E2独立地是1到4个碳原子的烷基和E3和E4连在一起是五亚甲基,或E1和E2;和E3和E4各自连在一起是五亚甲基,
R1是1到18个碳原子的烷基,5到12个碳原子的环烷基,7到12个碳原子的二环或三环烃基团,7到15个碳原子的苯基烷基,6到10个碳原子的芳基或被一个至三个1到8个碳原子的烷基取代的该芳基,
R2是氢或1到12个碳原子的线性或支链烷基,
R3是1到8个碳原子的亚烷基,或R3是-CO-,-CO-R4-,-CONR2-或-CO-NR2-R4-,
R4是1到8个碳原子的亚烷基,
R5是氢,1到12个碳原子的线性或支链烷基,或
或当R4是亚乙基时,两个R5甲基取代基能够被直接的键连接,这样三嗪桥连基团-N(R5)-R4-N(R5)-是哌嗪-1,4-二基结构部分,
R6是2到8个碳原子的亚烷基或R6是
前提条件是,当R6是上述结构时Y不是-OH,
A是-O-或-NR7-,其中R7是氢,1到12个碳原子的直链或支链烷基,或R7是
T是苯氧基,被一个或两个1到4个碳原子的烷基、1到8个碳原子的烷氧基或-N(R2)2取代的苯氧基,前提条件是R2不是氢,或T是
X是-NH2,-NCO,-OH,-O-缩水甘油基,或-NHNH2,和
Y是-OH,-NH2,-NHR2(其中R2不是氢);或Y是-NCO,-COOH,环氧乙烷基,-O-缩水甘油基,或-Si(OR2)3;或组合结构R3-Y-是-CH2CH(OH)R2,其中R2是烷基或被一个至四个氧原子***的该烷基,或R3-Y-是-CH2OR2;
或
其中该位阻胺化合物是N,N’,N_-三{2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚胺基二丙基胺;N,N’,N”-三{2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚胺基二丙基胺,和由通式I、II、IIA和III表述的桥接衍生物的混合物
R1NH-CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4 (I)
T-E1-T1 (II)
T-E1 (IIA)
G-E1-G1-E1-G2 (III)
其中在通式I的四胺中
R1和R2是s-三嗪结构部分E;和R3和R4中的一个是s-三嗪结构部分E,R3或R4中的另一个是氢,
E是
R是甲基,丙基,环己基或辛基,
R5是1到12个碳原子的烷基,
其中在R是丙基、环己基或辛基的通式II或IIA的化合物中,
T和T1各自是被与通式I中相同定义的R1-R4取代的四胺,其中
(1)在各四胺中s-三嗪结构部分E的一个被基团E替代,它在两个四胺T和T1之间形成桥基,
E1是
或
(2)基团E1能够在与通式IIA中相同的四胺T中具有两个末端,其中四胺的E结构部分的两个都被一个E1基团替代,或
(3)四胺T的全部三个s-三嗪取代基能够是E1,这样一个E1连接T和T1和第二个E1具有在四胺T中的两个末端,
L是丙烷二基,环己烷二基或辛烷二基;
其中在通式III的化合物中
G,G1和G2各自是由与通式I中定义的R1-R4取代的四胺,只是G和G2各具有被E1替代的一个s-三嗪结构部分E,和G1具有被E1替代的两个三嗪结构部分E,这样在G和G1之间有桥基和在G1和G2之间有第二个桥基;
该混合物是通过两个到四个当量的2,4-双[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与一个当量的N,N’-双(3-氨基丙基)乙二胺反应制备的;或该位阻胺是通式IIIb的化合物
其中该指数n是1到15;
R12是C2-C12亚烷基,C4-C12亚链烯基,C5-C7亚环烷基,C5-C7亚环烷基二(C1-C4亚烷基),C1-C4亚烷基二(C5-C7亚环烷基),亚苯基二(C1-C4亚烷基)或被1,4-哌嗪二基、-O-或>N-X1***的C4-C12亚烷基,其中X1是C1-C12酰基或(C1-C12烷氧基)羰基或具有下面给出的R14的定义中除氢以外的一种;或R12是以下结构式(Ib’)或(Ic’)的基团;
其中m是2或3,
X2是C1-C18烷基,未被取代的或被1、2或3个C1-C4烷基取代的C5-C12环烷基;未被取代的或被1、2或3个C1-C4烷基或C1-C4烷氧基取代的苯基,未被取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;和
该基团X3彼此独立地是C2-C12亚烷基;
R13,R14和R15,它们可以相同或不同,是氢,C1-C18烷基,未取代或被1、2或3个C1-C4烷基取代的C5-C12环烷基;C3-C18链烯基,未取代或被1、2或3个C1-C4烷基或C1-C4烷氧基取代的苯基;未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;四氢糠基或在2、3或4位上被-OH,C1-C8烷氧基,二(C1-C4烷基)氨基或下式(Ie’)的基团取代的C2-C4烷基;
其中Y是-O-;-CH2-;-CH2CH2-或>N-CH3,
或-N(R14)(R15)另外是式(Ie’)的基团;
基团A各自独立地是-OR13,-N(R14)(R15)或式(IIId)的基团;
X是-O-或>N-R16;
R16是氢,C1-C18烷基,C3-C18链烯基,未被取代的或被1、2或3个C1-C4烷基取代的C5-C12环烷基;未被取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;四氢化糠基,以下结构式(IIIf)的基团,
或在2、3和4位上被-OH取代的C2-C4烷基,C1-C8烷氧基,二(C1-C4烷基)氨基或以下结构式(Ie’)的基团;
R11具有对于R16给出的定义中的一种;和
该基团B彼此独立地具有对于A给出的定义中的一种。
4.根据权利要求1的组合物,其中组分(i)的位阻胺稳定剂选自
1-环己氧基-2,2,6,6-四甲基-4-十八烷基氨基哌啶;
双(1-辛基氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-(2-羟乙基氨基)-s-三嗪;
双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)已二酸酯;
2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪;
1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶;
1-(2-羟基-2-甲基丙氧基)-4-氧代-2,2,6,6-四甲基哌啶;
1-(2-羟基-2-甲基丙氧基)-4-十八烷酰基氧基-2,2,6,6-四甲基哌啶;
双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;
双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)已二酸酯;
2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟乙基氨基)-s-三嗪;
2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-双(3-氨基丙基)乙二胺)的反应产物;和
以下通式的化合物
其中n是1到15。
5.根据权利要求1的组合物,其中组分(i)的位阻胺稳定剂是以基于聚乳酸聚合物基质的重量计0.05重量%到20重量%的量存在。
6.根据权利要求1的组合物,其中组分(ii)的普通阻燃剂选自
多溴化二苯醚,
十溴二苯醚,
磷酸三[3-溴-2,2-双(溴甲基)丙基]酯,
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,
双-(N,N’-羟基乙基)四氯亚苯基二胺,
聚-β-氯乙基三磷酸酯混合物,
四溴双酚A双(2,3-二溴丙基醚),
溴化环氧树脂,
亚乙基-双(四溴邻苯二甲酰亚胺),
双(六氯环戊二烯基)环辛烷,
氯化石蜡,
八溴二苯基醚,
六氯环戊二烯衍生物,
1,2-双(三溴苯氧基)乙烷,
四溴-双酚A,
亚乙基双-(二溴-降冰片烷二羧酰亚胺),
双-(六氯环戊二烯基)环辛烷,
聚四氟乙烯,
异氰脲酸三-(2,3-二溴丙基)酯,和
亚乙基双-四溴邻苯二甲酰亚胺,
四苯基间苯二酚二亚磷酸酯,
四(羟基甲基)磷鎓硫化物,
N,N-双(2-羟基乙基)-氨基甲基膦酸二乙基酯,
磷酸的羟烷基酯,
聚磷酸铵,
间苯二酚二磷酸酯低聚物,
膦腈阻燃剂,
乙二胺二磷酸酯,
聚异氰脲酸酯,
异氰脲酸的酯类,
异氰脲酸酯,
羟烷基异氰脲酸酯,
蜜胺氰脲酸盐,
蜜胺硼酸盐,
蜜胺磷酸盐,
蜜胺聚磷酸盐,
蜜胺焦磷酸盐,
蜜胺铵聚磷酸盐,
蜜胺铵焦磷酸盐,
膦酸酯和它们的金属盐,和
亚磷酸酯和它们的金属盐。
7.根据权利要求1的组合物,其中组分(ii)的普通阻燃剂是以基于聚乳酸聚合物基质的重量的0.5重量%到45重量%的量存在。
8.根据权利要求1的组合物,进一步包括选自水滑石和无定形的碱性碳酸镁铝中的除酸剂。
9.根据权利要求8的组合物,其中该除酸剂是以基于聚乳酸聚合物基质计0.1重量%到1.0重量%的量存在。
10.根据权利要求1的组合物,包括附加组分,其选自颜料,染料,增塑剂,抗氧化剂,触变剂,流平助剂,碱性助稳定剂,硝酮稳定剂,氧化胺稳定剂,苯并呋喃酮稳定剂,UV吸收剂,位阻胺,金属减活剂,金属氧化物,有机磷化合物,羟胺,和它们的混合物。
11.根据权利要求1的组合物,包括附加组分,该组分选自酚类抗氧化剂,硬脂酸钙,硬脂酸锌,亚磷酸酯和亚膦酸酯稳定剂,苯并呋喃酮稳定剂,2-(2’-羟苯基)苯并***和2-(2-羟苯基)-1,3,5-三嗪类型的UV吸收剂,和位阻胺。
12.下面组分的协同混合物在为聚乳酸聚合物基质赋予光稳定性和阻燃性中的用途:
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺基阻燃剂中的至少一种普通阻燃剂。
13.为聚乳酸聚合物基质赋予光稳定性和阻燃性的方法,该方法包括向该聚合物基质中添加:
(i)至少一种位阻胺稳定剂,
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺基阻燃剂中的至少一种普通阻燃剂。
14.模塑的聚乳酸聚合物制品,它包括聚乳酸聚合物基质和下面组分的协同混合物:
(i)至少一种位阻胺稳定剂和
(ii)选自有机卤素,含磷,异氰脲酸酯和蜜胺基阻燃剂中的至少一种普通阻燃剂。
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JP2003192921A (ja) * | 2001-10-19 | 2003-07-09 | Matsushita Electric Ind Co Ltd | 高分子組成物 |
KR101029863B1 (ko) * | 2001-12-21 | 2011-04-18 | 시바 홀딩 인코포레이티드 | 신규한 난연제 화합물 |
US6869985B2 (en) * | 2002-05-10 | 2005-03-22 | Awi Licensing Company | Environmentally friendly polylactide-based composite formulations |
-
2004
- 2004-07-09 WO PCT/EP2004/051436 patent/WO2005014706A1/en active IP Right Grant
- 2004-07-09 CA CA002532456A patent/CA2532456A1/en not_active Abandoned
- 2004-07-09 DE DE602004003500T patent/DE602004003500T2/de not_active Expired - Lifetime
- 2004-07-09 JP JP2006520825A patent/JP2006528254A/ja active Pending
- 2004-07-09 CN CNB2004800206070A patent/CN100500744C/zh not_active Expired - Fee Related
- 2004-07-09 ES ES04766175T patent/ES2276335T3/es not_active Expired - Lifetime
- 2004-07-09 EP EP04766175A patent/EP1646681B1/en not_active Expired - Lifetime
- 2004-07-09 AT AT04766175T patent/ATE346883T1/de not_active IP Right Cessation
- 2004-07-13 US US10/890,453 patent/US20050014871A1/en not_active Abandoned
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101977992B (zh) * | 2008-04-23 | 2013-09-04 | 尤尼吉可株式会社 | 阻燃性聚乳酸系树脂组合物和使用其的成型体 |
CN101747507B (zh) * | 2008-12-16 | 2012-04-25 | 财团法人工业技术研究院 | 含膦聚合物及包含此含膦聚合物的聚乳酸材料 |
CN103013148A (zh) * | 2011-09-20 | 2013-04-03 | 富士施乐株式会社 | 含有木粉的材料、其制造方法和成型体 |
CN103013148B (zh) * | 2011-09-20 | 2016-08-03 | 富士施乐株式会社 | 含有木粉的材料、其制造方法和成型体 |
CN102634181A (zh) * | 2012-04-25 | 2012-08-15 | 中国科学院宁波材料技术与工程研究所 | 一种催化阻燃聚乳酸复合材料 |
CN102634181B (zh) * | 2012-04-25 | 2013-09-04 | 中国科学院宁波材料技术与工程研究所 | 一种催化阻燃聚乳酸复合材料 |
CN106009558A (zh) * | 2015-03-31 | 2016-10-12 | 富士施乐株式会社 | 树脂组合物和树脂成型体 |
CN105671672A (zh) * | 2016-02-25 | 2016-06-15 | 东华大学 | 只含碳、氢、氧三元素的阻燃聚乳酸纤维及其制备方法 |
CN106349670A (zh) * | 2016-09-27 | 2017-01-25 | 北京服装学院 | 一种改性聚乳酸体系及其制备方法 |
CN106349670B (zh) * | 2016-09-27 | 2018-07-13 | 北京服装学院 | 一种改性聚乳酸体系及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
ES2276335T3 (es) | 2007-06-16 |
DE602004003500T2 (de) | 2007-10-04 |
US20050014871A1 (en) | 2005-01-20 |
ATE346883T1 (de) | 2006-12-15 |
CA2532456A1 (en) | 2005-02-17 |
EP1646681B1 (en) | 2006-11-29 |
WO2005014706A1 (en) | 2005-02-17 |
CN100500744C (zh) | 2009-06-17 |
JP2006528254A (ja) | 2006-12-14 |
DE602004003500D1 (de) | 2007-01-11 |
EP1646681A1 (en) | 2006-04-19 |
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