CH679862A5 - - Google Patents
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- Publication number
- CH679862A5 CH679862A5 CH207/90A CH20790A CH679862A5 CH 679862 A5 CH679862 A5 CH 679862A5 CH 207/90 A CH207/90 A CH 207/90A CH 20790 A CH20790 A CH 20790A CH 679862 A5 CH679862 A5 CH 679862A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- compound
- hydrogen
- group
- Prior art date
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- -1 Ci-s-alkylphenyl Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000003381 stabilizer Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GWWYBYNZFWRRSG-UHFFFAOYSA-N hydroxyphosphanyloxyphosphinous acid;1,2,3,4-tetrakis(2,4-ditert-butylphenyl)biphenylene Chemical compound OPOPO.CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C(C(=C1C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)=C(C=2C3=CC=CC=2)C3=C1C1=CC=C(C(C)(C)C)C=C1C(C)(C)C GWWYBYNZFWRRSG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 229960004279 formaldehyde Drugs 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FMUYQRFTLHAARI-UHFFFAOYSA-N 2,4-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 FMUYQRFTLHAARI-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- FDAJTLLBHNHECW-UHFFFAOYSA-N 2,4-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=C(O)C(CCCCCCCCC)=C1 FDAJTLLBHNHECW-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- JKFZLMPBXBMSPD-UHFFFAOYSA-N 2-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC=C1O JKFZLMPBXBMSPD-UHFFFAOYSA-N 0.000 description 1
- OUVMWIKEEGQNFZ-UHFFFAOYSA-N 2-hydroxybenzoic acid;[3-(2-hydroxybenzoyl)phenyl]-(2-hydroxyphenyl)methanone Chemical class OC(=O)C1=CC=CC=C1O.OC1=CC=CC=C1C(=O)C1=CC=CC(C(=O)C=2C(=CC=CC=2)O)=C1 OUVMWIKEEGQNFZ-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004801 Chlorinated PVC Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004813 Perfluoroalkoxy alkane Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229940118056 cresol / formaldehyde Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CGPRUXZTHGTMKW-UHFFFAOYSA-N ethene;ethyl prop-2-enoate Chemical compound C=C.CCOC(=O)C=C CGPRUXZTHGTMKW-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010096 film blowing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- HDNHWROHHSBKJG-UHFFFAOYSA-N formaldehyde;furan-2-ylmethanol Chemical compound O=C.OCC1=CC=CO1 HDNHWROHHSBKJG-UHFFFAOYSA-N 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229920011301 perfluoro alkoxyl alkane Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4841—Aromatic acids or derivatives (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/485—Polyphosphonous acids or derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
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CH679 862A5 CH679 862A5
Beschreibung description
Stabilisatoren für polvmere Materialien Stabilizers for polymer materials
Gegenstand der Erfindung sind Stabilisator-Kompositionen für polymere, organische Materialien. Die erfindungsgemässen Stabilisator-Kompositionen sind synergistisch wirkende Mischungen von a) 40 bis 99,9 Gewichtsprozent eines oder mehrerer Phosphonite der Formel I The invention relates to stabilizer compositions for polymeric, organic materials. The stabilizer compositions according to the invention are synergistic mixtures of a) 40 to 99.9 percent by weight of one or more phosphonites of the formula I.
r—0-p / p^°~~r! ) r — 0-p / p ^ ° ~~ r! )
*-o/ X°~R'm tu und b) 0,1 bis 60 Gewichtsprozent eines Phosphits der Formel II * -o / X ° ~ R'm tu and b) 0.1 to 60 percent by weight of a phosphite of the formula II
0-Ri 0-Ri
/ /
R3- 0-P (II) R3-0-P (II)
\ \
0-Ri worin m 0 oder 1, 0-Ri where m is 0 or 1,
n 0 oder 1, n 0 or 1,
Y eine Sauerstoff-, Schwefel- oder 1,4-PhenyIen-Brücke oder ein Brückenglied der Formel -CH(Rs) Y is an oxygen, sulfur or 1,4-phenylene bridge or a bridge member of the formula -CH (Rs)
alle R-O- und Ri-O-Gruppen unabhängig voneinander, den Rest eines aliphatischen, alicyclischen oder aromatischen Alkohols, der bis zu drei Hydroxylgruppen enthalten kann, wobei jedoch die Hydroxylgruppen nicht so angeordnet sind, dass sie Teile eines Phosphor-enthaltenden Ringes sein können (als monovalente R-O-Gruppen bezeichnet), all RO and Ri-O groups independently of one another, the remainder of an aliphatic, alicyclic or aromatic alcohol, which can contain up to three hydroxyl groups, but the hydroxyl groups are not arranged such that they can be part of a phosphorus-containing ring ( referred to as monovalent RO groups),
oder je zwei an ein Phosphoratom gebundene R-O-, bzw. Ri-O-Gruppen, jeweils unabhängig voneinander zusammen den Rest eines aliphatischen, alicyclischen oder aromatischen Alkohols mit insgesamt bis zu drei Hydroxylgruppen (als bivalente R-O-, bzw. Ri-O-Gruppen bezeichnet), or two RO or Ri-O groups bonded to a phosphorus atom, each independently of one another together the remainder of an aliphatic, alicyclic or aromatic alcohol with a total of up to three hydroxyl groups (as bivalent RO or Ri-O groups designated),
R3-O- den Rest eines aliphatischen, alicyclischen oder aromatischen Alkohols, der bis zu drei Hydroxylgruppen enthalten kann, wobei die Hydroxylgruppen jedoch nicht so angeordnet sind, dass sie Teile eines Phosphor-enthaltenden Ringes sein können, R3-O- the residue of an aliphatic, alicyclic or aromatic alcohol, which can contain up to three hydroxyl groups, but the hydroxyl groups are not arranged such that they can be part of a phosphorus-containing ring,
Rs Wasserstoff, Ci-s-Alkyl oder eine Gruppe der Formel COORs und Rß Ci-s-Alkyl bedeuten, Rs is hydrogen, Ci-s-alkyl or a group of the formula COORs and Rß Ci-s-alkyl,
wobei jedoch wegen des prioritätsälteren CH-Patentgesuches Nr. 00 474/89-3 Tetrakis-(2,4-di-tert.-butylphenyl)-biphenylen-diphosphonit als Verbindung der Formel I ausgeschlossen ist, und vorzugsweise mindestens eine R-O- und mindestens eine Ri-O-Gruppe ein Phenolrest ist, der in 2-Stellung eine ste-risch gehinderte Gruppe trägt. however, because of the prior priority CH patent application No. 00 474 / 89-3 tetrakis (2,4-di-tert-butylphenyl) biphenylene diphosphonite is excluded as a compound of the formula I, and preferably at least one RO and at least one a Ri-O group is a phenol residue which bears a sterically hindered group in the 2-position.
Wenn R-O- und R1-O- divalente Reste sind, leiten sie sich vorzugsweise von zwei- oder dreiwertigen Alkoholen ab. When R-O and R1-O are divalent residues, they are preferably derived from di- or trihydric alcohols.
Vorzugsweise bedeutet R R' und dieses ist Alkyl, Aralkyl (vzw. ggf. subst. Phenyl oder Phenylen), Aryl (vzw. ggf. subst. Phenyl) oder eine Gruppe der Formel a worin die Kerne A und B weitere Substituenten tragen können und Y' eine Sauerstoff- oder Schwefelbrücke oder ein Brückenglied der Formel -CH(Rs)-, Preferably RR 'means and this is alkyl, aralkyl (preferably substituted phenyl or phenylene), aryl (preferably substituted phenyl) or a group of the formula a in which the cores A and B can carry further substituents and Y 'an oxygen or sulfur bridge or a bridge member of the formula -CH (Rs) -,
Rs Wasserstoff, Ci-s-Alkyl oder eine Gruppe der Formel -COOR6, Rs is hydrogen, Ci-s-alkyl or a group of the formula -COOR6,
R6 Ci—s-Alkyl und n 0 oder 1 bedeuten (als divalentes R' bezeichnet). R6 is Ci-s-alkyl and n is 0 or 1 (referred to as divalent R ').
Besonders bevorzugte Reste R sind die Reste R", wobei diese Ci-22-Alkyl, Phenyl, das 1 bis 3 Substituenten aus der Reihe Cyan Ci_22-AIkyI, Ci-22-Alkoxy, Benzyl, Phenyl, 2,2,6,6-Tetramethyl-piperi-dyI-4-, Hydroxy, Ci-a-Alkyl-phenyl, Carboxyl, -C(CH3)2-C6Hs, -COO-Ci-22-Alkyl, -CH2CH2- Particularly preferred radicals R are the radicals R ", these Ci-22-alkyl, phenyl, the 1 to 3 substituents from the series Cyan Ci_22-AlkyI, Ci-22-alkoxy, benzyl, phenyl, 2,2,6,6 -Tetramethyl-piperidyl-4-, hydroxy, Ci-a-alkylphenyl, carboxyl, -C (CH3) 2-C6Hs, -COO-Ci-22-alkyl, -CH2CH2-
2 2nd
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CH 679 862 A5 CH 679 862 A5
COOH, -CH2CH2COO-Ci_22-Alkyl oder -CH2-S-Ci-22-Alkyi tragen kann; oder eine Gruppe der Formel i bis vii Can carry COOH, -CH2CH2COO-Ci_22-alkyl or -CH2-S-Ci-22-alkyl; or a group of the formula i to vii
24 24th
Cl Cl
(ili) (ili)
r©)—^24 r ©) - ^ 24
(v) î (v) î
h—c—c—nh h — c — c — nh
N M N M
0 0 0 0
(vi) ; oder (vi); or
24> 2 ' 24> 2 '
c(ch3^ c (ch3 ^
(ch3)3 (ch3) 3
oder zwei R" gemeinsam eine Gruppe der Formel viii or two R "together form a group of the formula viii
(vii) (vii)
3 3rd
CH 679 862 A5 CH 679 862 A5
15 15
m 5 m 5
15 15
(vii i ) (vii i)
bedeuten, wobei R15 Wasserstoff oder Ci_22-Alkyl, mean, where R15 is hydrogen or Ci_22-alkyl,
R16 Wasserstoff, Ci_*-Alkyl oder -CO-Ci_s-Alkyl, R16 is hydrogen, Ci _ * alkyl or -CO-Ci_s-alkyl,
R17 Wasserstoff oder Ci-22-Aikyl, R17 is hydrogen or Ci-22-aikyl,
Ris Wasserstoff, Ci-22-AIkyI, Ci-22-Alkoxy, Benzyl, Cyan, Phenyl, Hydroxyl, Ci-a-Alkylphenyl, C1-22-Alkoxycarbonyl, Ci-22-Alkoxycarbonyläthyl, Carboxyäthyl, 2,2,6,6-Tetramethylpiperidyl-4- oder eine Gruppe der Formel -CH2-S-Ci-22-Alkyl oder-C(CH3)2-C6H5 und R24 Wasserstoff, Ci-22-Alkyl, Hydroxy oder Alkoxy bedeuten und Y' und n die oben angegebenen Bedeutungen besitzen. Ris hydrogen, Ci-22-AlkyI, Ci-22-alkoxy, benzyl, cyano, phenyl, hydroxyl, Ci-a-alkylphenyl, C1-22-alkoxycarbonyl, Ci-22-alkoxycarbonylethyl, carboxyethyl, 2,2,6,6 -Tetramethylpiperidyl-4- or a group of the formula -CH2-S-Ci-22-alkyl or -C (CH3) 2-C6H5 and R24 are hydrogen, Ci-22-alkyl, hydroxy or alkoxy and Y 'and n are the above have the meanings given.
Insbesondere bevorzugt als Reste R sind die Reste R'", die einer der Formeln a bis g Particularly preferred as radicals R are the radicals R '', which are one of the formulas a to g
(b) (b)
R« R «
13 13
13 (c) 13 (c)
(f) (f)
(g) (G)
entsprechen, worin R10 Wasserstoff, Ci-s-Alkyl, C-i-s-Alkoxy, Phenyl, C-i-s-Alkylphenyl oder Phenyl-Ci-4-alkyl, correspond in which R10 is hydrogen, Ci-s-alkyl, C-i-s-alkoxy, phenyl, C-i-s-alkylphenyl or phenyl-Ci-4-alkyl,
R11 und R12, unabhängig voneinander, Wasserstoff, Ci-22-Alkyl, Phenyl oder Ci-s-Alkylphenyl, R11 and R12, independently of one another, are hydrogen, Ci-22-alkyl, phenyl or Ci-s-alkylphenyl,
R13 Wasserstoff oder Ci-s-Alkyl und R13 is hydrogen or Ci-s-alkyl and
R14 Cyan, Carboxyl oder Ci_s-Alkoxycarbonyl bedeuten. R14 is cyan, carboxyl or Ci_s-alkoxycarbonyl.
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CH 679 862 A5 CH 679 862 A5
Unter den Gruppen der Formel a sind 2-tert.-Butylphenyl, 2-Phenylphenyl, 2-(1',1'-Dimethyl-propyl)-phenyl, 2-Cyclohexylphenyl, 2-tert.-Butyl-4-methylphenyl, 2,4-Di-tert.-amylphenyl, 2,4-Di-tert.-butyl-phenyl, 2,4-Diphenylphenyi, 2,4-Di-tert.-octylphenyI, 2-tert.-Butyi-4-phenyl-phenyl, 2,4-Bis-(1',1'-di-methylprapyl)-phenyl, 2-(1 '-Phenyl-1 '-methyläthyl)-phenyl, 2,4-Bis-(1 '-PhenyI-1 '-methyläthyl)-phenyl und 2,4-Di-tert.-butyl-6-methylphenyl bevorzugt. Among the groups of formula a are 2-tert-butylphenyl, 2-phenylphenyl, 2- (1 ', 1'-dimethyl-propyl) -phenyl, 2-cyclohexylphenyl, 2-tert-butyl-4-methylphenyl, 2 , 4-di-tert-amylphenyl, 2,4-di-tert-butyl-phenyl, 2,4-diphenylphenyl, 2,4-di-tert-octylphenyl, 2-tert-butyl-4-phenyl -phenyl, 2,4-bis- (1 ', 1'-dimethylprapyl) -phenyl, 2- (1'-phenyl-1' -methylethyl) -phenyl, 2,4-bis- (1 '-phenyI -1'-methylethyl) phenyl and 2,4-di-tert-butyl-6-methylphenyl are preferred.
Ri ist vorzugsweise Ri', das unabhängig von R' eine der Bedeutungen von R' hat, dieses ist besonders als Ri" bevorzugt, wobei Rt" unabhängig von R" eine der Bedeutungen dieses Symbols hat und insbesondere ist Ri, Ri"', das, unabhängig von R"', eine der Bedeutungen von R'" hat. Ri is preferably Ri ', which has one of the meanings of R' independently of R ', this is particularly preferred as Ri ", where Rt" independently of R "has one of the meanings of this symbol and in particular Ri, Ri"' is that , regardless of R "', has one of the meanings of R'".
R3 ist vorzugsweise R3', das unabhängig von R' eine der monovalenten Reste von R' bedeutet, besonders bevorzugte Reste R3 sind die Reste R3", und diese besitzen (unabhängig davon) eine der monovalenten Bedeutungen von R", insbesondere ist R3 R3'", das (unabhängig von R'") wieder einen monovalenten Rest aus den Bedeutungen von R'" darstellt. R3 is preferably R3 ', which is one of the monovalent radicals of R', independently of R ', particularly preferred radicals R3 are the radicals R3 ", and these (independently of this) have one of the monovalent meanings of R", in particular R3 is R3' ", which (regardless of R '") again represents a monovalent radical from the meanings of R' ".
Vorzugsweise bedeutet m 1. M is preferably 1.
Vorzugsweise enthält eine erfindungsgemässe Stabilisator-Kombination a) ein Diphosphonit der Formel I (oben, als Komponente a bezeichnet), A stabilizer combination a) according to the invention preferably comprises a diphosphonite of the formula I (referred to above as component a),
b) ein Phosphit der obigen Formel II (als Komponente II bezeichnet) und c) ein Monophosphonit der obigen Formel I (als Komponente c bezeichnet). b) a phosphite of formula II above (referred to as component II) and c) a monophosphonite of formula I above (referred to as component c).
Zusätzlich kann eine erfindungsgemässe Stabilisator-Komposition noch ein Phenol der Formel IV oder V (im folgenden als Komponente d bezeichnet) In addition, a stabilizer composition according to the invention can also be a phenol of the formula IV or V (hereinafter referred to as component d)
worin R7 eine der monovalenten, unter R genannten Gruppen bedeutet und Ra eine der divalenten unter R genannten Gruppen bedeutet. wherein R7 is one of the monovalent groups mentioned under R and Ra is one of the divalent groups mentioned under R.
Vorzugsweise haben R und Ri in den erfindungsgemässen Stabilisator-Kompositionen dieselbe Bedeutung. R and Ri preferably have the same meaning in the stabilizer compositions according to the invention.
Bevorzugte Stabilisator-Kompositionen enthalten 50 bis 95%, insbesondere 70 bis 90% einer Komponente der Formel I und 5 bis 50%, insbesondere 10 bis 30% einer Komponente der Formel II. Preferred stabilizer compositions contain 50 to 95%, in particular 70 to 90% of a component of the formula I and 5 to 50%, in particular 10 to 30% of a component of the formula II.
Besonders bevorzugte erfindungsgemässe Stabilisator-Kompositionen enthalten a) 60-80% der oben angegebenen Komponente a, Particularly preferred stabilizer compositions according to the invention contain a) 60-80% of the above-mentioned component a,
b) 5-20% der oben angegebenen Komponente (Formel) II, b) 5-20% of the above-mentioned component (formula) II,
c) 10-20% der oben angegebenen Komponente c und d) 0-5% der oben angegebenen Komponente d. c) 10-20% of component c above and d) 0-5% of component d above.
Gleichermassen bevorzugt sind auch die Stabilisatorkombinationen mit a) 16-50% der Komponente a, Equally preferred are the stabilizer combinations with a) 16-50% of component a,
b) 20-60% der Komponente (der Formel) II, b) 20-60% of component (of the formula) II,
c) 3-20% der Komponente c und d) 0-5% der Komponente d, c) 3-20% of component c and d) 0-5% of component d,
wobei alle Prozentangaben als Gewichtsprozente zu verstehen sind. where all percentages are to be understood as percentages by weight.
Die Herstellung der Verbindungen der Fonnel I erfolgt durch Umsetzung von a) 2 Mol einer Verbindung der Formel X The compounds of formula I are prepared by reacting a) 2 moles of a compound of the formula X.
worin R30 ein monovalenter Rest der Bedeutung von R ist, und 2 Mol einer Verbindung der Formel XI wherein R30 is a monovalent radical of the meaning of R, and 2 moles of a compound of formula XI
worin R31 ein monovalenter Rest der Bedeutung von Ri ist, mit 1 Mol einer Verbindung der Formel XIV wherein R31 is a monovalent radical of the meaning of Ri, with 1 mol of a compound of formula XIV
R7 (OH) (IV) Rs (OH)2 (V) R7 (OH) (IV) Rs (OH) 2 (V)
Rso-OH (X) Rso-OH (X)
R31-OH (XI), R31-OH (XI),
(XIV) (XIV)
worin Y, m und n die obengenannten Bedeutungen besitzen, oder wherein Y, m and n have the meanings given above, or
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CH 679 862 A5 CH 679 862 A5
b) 1 Mol einer Verbindung der Formel XII R32(OH)2 (XII), b) 1 mole of a compound of the formula XII R32 (OH) 2 (XII),
worin R32 ein divalenter Rest der Bedeutung von Ri ist, und 2 Mol einer Verbindung der obigen Formel X, mit 1 Mol einer Verbindung der obigen Formel XIV, worin m = 1, oder c) 1 Mol einer Verbindung der obigen Formel XII und 1 Mol einer Verbindung der Formel XIII wherein R32 is a divalent radical of the meaning of Ri, and 2 moles of a compound of the above formula X, with 1 mole of a compound of the above formula XIV, wherein m = 1, or c) 1 mole of a compound of the above formula XII and 1 mole a compound of formula XIII
Rs3(OH)2 (XIII), Rs3 (OH) 2 (XIII),
worin R33 ein divalenter Rest der Bedeutung von R ist, mit 1 Mol einer Verbindung der obigen Formel XIV, bei erhöhten Temperaturen, vorzugsweise zwischen 40 und 140°C. wherein R33 is a divalent radical of the meaning of R, with 1 mol of a compound of formula XIV above, at elevated temperatures, preferably between 40 and 140 ° C.
Ein weiterer Gegenstand der Erfindung sind auch die neuen Verbindungen der Formel XV und XVI The invention also relates to the new compounds of the formulas XV and XVI
— R22—(Q^— - R22— (Q ^ -
21 21
worin n 0 oder 1, vorzugsweise 0, where n is 0 or 1, preferably 0,
beide d 1 oder 2, both d 1 or 2,
alle R2i und R22, unabhängig voneinander Wasserstoff, all R2i and R22, independently of one another hydrogen,
Ci-4-Alkyl (vorzugsweise tert. Butyl oder Methyl) oder eine Gruppe der Formel Ci-4-alkyl (preferably tert-butyl or methyl) or a group of the formula
-C(CH3)2-C6Hs bedeuten, Are -C (CH3) 2-C6Hs,
wobei jedoch mindestens ein R2i oder mindestens ein R22, jedoch nicht alle R2i eine Gruppe der Formel ■ C(CH3)2-C6H5, bedeuten, however, at least one R2i or at least one R22, but not all R2i, mean a group of the formula ■ C (CH3) 2-C6H5,
(H)2-d worin d 1 oder 2, vorzugsweise 2 bedeutet. (H) 2-d where d is 1 or 2, preferably 2.
Auch diese Verbindungen der Formeln XV und XVI sind, wie die übrigen Verbindungen der Formel l ausgezeichnete Stabilisatoren für organische Polymere. These compounds of the formulas XV and XVI, like the other compounds of the formula I, are also excellent stabilizers for organic polymers.
Sie werden vorzugsweise auch in Kombination mit einer Verbindung der Formel II, in den oben angegebenen Verhältnissen verwendet, welche Mischungen gegenüber den Einzelverbindungen einen ausgeprägten synergistischen Effekt zeigen. They are preferably also used in combination with a compound of the formula II, in the ratios given above, which mixtures have a pronounced synergistic effect compared to the individual compounds.
6 6
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 679 862 A5 CH 679 862 A5
Die erfindungsgemässen Stabilisator-Kompositionen werden vorzugsweise in Mengen von 0,01 bis 2%, insbesondere, 0,05 bis 0,3% (Gewichtsprozente) in das polymere organische Material eingearbeitet und verbessern so die Verarbeitungs- und Alterungs-Stabilität entscheidend. Insbesondere das Vergilben wird weitgehend zurückgedrängt und der «melt flow index» (M Fl) wird wesentlich verbessert. The stabilizer compositions according to the invention are preferably incorporated into the polymeric organic material in amounts of 0.01 to 2%, in particular 0.05 to 0.3% (percentages by weight) and thus decisively improve the processing and aging stability. In particular, yellowing is largely suppressed and the “melt flow index” (M Fl) is significantly improved.
Mit Erfolg zu stabilisierende polymere organische Materialien sind z.B. die Homopolymeren, Copoly-meren und Polymer-Mischungen von Celluloseacetat, Celluloseacetatobutyrat, Celluloseacetopropio-nat, Cresol/Formaldehyd-Harz, Carboxymethylcellulose, Cellulosenitrat, Cellulosepropionate, Casein Plastiks, Casein-Formaldehyde, Cellulose Triacetate, Etylcellulose, Epoxyharze, Methylcellulose, Me-lamin/Formaldehyd-Harz, Polyamid, Polyamidimide, Polyacrylonitril, Polybutylen-1, Polybutylacrylat, Po-ly-(butylenterephthalat), Polycarbonat, Poly-(chlorotrifluoräthylen), Poly-(diaIlylphthalat), Polyäthylen, chloriertes Polyäthylen, Poly-(etheretherketon), Polyetherimid, Polyäthylenoxid, Polyethersulphon, Po-lyethylenterephthalat, Polytetrafluoräthylen, Phenol/Formaldehyde-Harze, Polyimide, Polyisobutylen, Polyisocyanat, Polymethacrylimid, Poiymethylmethacrylat, Poly-(4-methylpenten-1), Poly-(a-methyl sty-rol), Polyoxymethylen, Polyacetal, Polypropylen, Polyphenylenether, Polyphenylensulphid, Polypheny-lensulphon, Polystyrol, Polysulphon, Polyurethan, Polyvinylacetat, Polyvinylalcohol, Polyvinylbutyral, chloriertes Polyvinylchlorid, Polyvinylidenchlorid, Polyvinylidenfluorid; Polyvinylfluorid, Polyvinylform-aldehyd, Polyvinylcarbazol, Polyvinylpyrrolidon, Silicon-Polymere, gesättigte Polyester, Harn-stoff/Formaldehyd-Harze, ungesättigte Polyester, Polyacrylat, Polymethacrylat, Polyacrylamide, Maleinsäure-Harze, Phenol-Harze, Anilin-Harze, Furan-Harze und Carbamid-Harze. Polymeric organic materials to be stabilized successfully are e.g. the homopolymers, copolymers and polymer mixtures of cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate, cresol / formaldehyde resin, carboxymethyl cellulose, cellulose nitrate, cellulose propionate, casein plastics, casein formaldehyde, cellulose triacetulose, etyl cellulose triacetate, et / Formaldehyde resin, polyamide, polyamideimide, polyacrylonitrile, polybutylene-1, polybutyl acrylate, poly (butylene terephthalate), polycarbonate, poly (chlorotrifluoroethylene), poly (diaIlyl phthalate), polyethylene, chlorinated polyethylene, poly (etheretherketone) Polyetherimide, polyethylene oxide, polyether sulfone, polyethylene terephthalate, polytetrafluoroethylene, phenol / formaldehyde resins, polyimides, polyisobutylene, polyisocyanate, polymethacrylimide, poiymethyl methacrylate, poly- (4-methylpentene-1), poly (a-methyl stoxymol) , Polyacetal, polypropylene, polyphenylene ether, polyphenylene sulfide, polyphenylene lens sulfone, polystyrene, polysulfone, polyurethane, polyvinyl acetate tat, polyvinyl alcohol, polyvinyl butyral, chlorinated polyvinyl chloride, polyvinylidene chloride, polyvinylidene fluoride; Polyvinyl fluoride, polyvinyl form aldehyde, polyvinyl carbazole, polyvinyl pyrrolidone, silicone polymers, saturated polyesters, urea / formaldehyde resins, unsaturated polyesters, polyacrylate, polymethacrylate, polyacrylamides, maleic acid resins, phenol resins, aniline resins, furan resins and Carbamide resins.
Geeignete Copolymere sind zum Beispiel: Suitable copolymers are, for example:
Acrylonitril/Butadieri/Acrylat, Acrylonitril/Butadien/Styrol, Acrylonitril/Methylmethacrylat, Acryloni-tril/Styrol/Acrylsäureester, Acrylonitril/Ethylen-Propylendien/Styrol; Acrylonitril/chloriertes Polyethy-len/Styrol, Ethylene/Ethylacrylat, Ethylen/Methacrylsäureester, Ethylene/Propylen, Ethylen/Propylen-dien, Ethylene/Vinylacetat, EthylenA/inylalcohol, Ethylen/Tetrafluoräthylen, Tetrafluoräthy-len/Hexafluoropropylen, Methacrylat/Butadien/Styrol, Melamin/Phenol/Formaldehyd, Polyester Blockamide, Perfluor-alkoxyalkan, Sty ro I/Acry lo n itri I, Styrol/Butadien, Styrol/Maleinsäureanhydrid, Styrol/a-Methylstyrol, Vinylchlorid/Ethylen, Vinylchlorid/Ethylen/Methacrylat, Vinylchlorid/Ethy-len/Vinylacetat, Vinylchlorid/Methylmethacrylat, Vinylchlorid/Octylacrylat, Vinylchlorid/Vinylacetat und Vinylchlorid/Vinylidechlorid. Acrylonitrile / butadieri / acrylate, acrylonitrile / butadiene / styrene, acrylonitrile / methyl methacrylate, acrylonitrile / styrene / acrylic acid ester, acrylonitrile / ethylene propylene diene / styrene; Acrylonitrile / chlorinated polyethylene / styrene, ethylene / ethyl acrylate, ethylene / methacrylic acid ester, ethylene / propylene, ethylene / propylene diene, ethylene / vinyl acetate, ethylene A / inyl alcohol, ethylene / tetrafluoroethylene, tetrafluoroethylene / hexafluoropropylene, methacrylate / butadiene , Melamine / phenol / formaldehyde, polyester block amides, perfluoroalkoxyalkane, styrofoam / acrylonitrile I, styrene / butadiene, styrene / maleic anhydride, styrene / a-methylstyrene, vinyl chloride / ethylene, vinyl chloride / ethylene / methacrylate, vinyl chloride / Ethylene / vinyl acetate, vinyl chloride / methyl methacrylate, vinyl chloride / octyl acrylate, vinyl chloride / vinyl acetate and vinyl chloride / vinylide chloride.
Die vorliegenden Stabilisator-Kompositionen eignen sich insbesondere zum Stabilisieren von Polyole-finen, d.h. besonders für Polypropylen und alle Varianten von Polyäthylen (Hochdruck-, Mittel- und Niederdruck-Polyäthylen), Polyisobutylen, Poly-4-methylpenten und deren Copolymere. Als zusätzliche Stabilisatoren können für die Polymermassen u.a. Antioxidantien, z.B. sterisch gehinderte Phenole, sekundäre aromatische Amine oder Thioäther (beschrieben z.B. in «Kunststoff-Additive», Gäch-ter/Müller, 3. Ausgabe, 1989, S. 42-8, UV-Stabilisatoren, z.B. sterisch gehinderte Amine (insbesondere N-unsubstituierte, N-AIkyl- oder N-Acyl-substituierte 2,2,6,6-Tetramethylpiperidinver-bindungen), UV-Absorber [insbesondere 2-(2'-Hydroxyphenyl)-benztriazolverbindungen, 2-Hydroxy-benzophenonverbindungen, 1,3-Bis-(2'-hydroxybenzoyl)-benzolsalicylate, Zimtsäurederivate und Oxalsäuredianilide), Antistatika, entflammungsverhindernde Mittel, Weichmacher, Nukleirmittel, Metall-De-aktivatoren, Biocide, Füllstoffe und Pigmente eingesetzt werden. The present stabilizer compositions are particularly suitable for stabilizing polyolefins, i.e. especially for polypropylene and all types of polyethylene (high pressure, medium and low pressure polyethylene), polyisobutylene, poly-4-methylpentene and their copolymers. Additional stabilizers for the polymer masses include Antioxidants, e.g. sterically hindered phenols, secondary aromatic amines or thioethers (described, for example, in “Kunststoff-Additive”, Gächter / Müller, 3rd edition, 1989, pp. 42-8), UV stabilizers, for example sterically hindered amines (especially N-unsubstituted , N-alkyl- or N-acyl-substituted 2,2,6,6-tetramethylpiperidine compounds), UV absorbers [in particular 2- (2'-hydroxyphenyl) benzotriazole compounds, 2-hydroxy-benzophenone compounds, 1,3- Bis (2'-hydroxybenzoyl) benzene salicylates, cinnamic acid derivatives and oxalic acid dianilides), antistatic agents, flame retardants, plasticizers, nucleic agents, metal deactivators, biocides, fillers and pigments.
Die erfindungsgemässen Stabilisator-Kompositionen können den Polymeren Materialien vor, während und nach ihrer Polymerisation, in fester, geschmolzener, in Lösungsmitteln gelöster Form oder als Masterbatches zugegeben werden. Die Lösungen enthalten im allgemeinen 10 bis 80% der Stabilisator-Komposition, die Masterbatches enthalten im allgemeinen ebenfalls 10 bis 80, vorzugsweise 40 bis 70% Stabilisator-Komposition, der Rest ist ein mit dem zu stabilisierenden Polymeren verträgliches Polymer. The stabilizer compositions according to the invention can be added to the polymer materials before, during and after their polymerization, in solid, molten form, dissolved in solvents or as masterbatches. The solutions generally contain 10 to 80% of the stabilizer composition, the masterbatches generally also contain 10 to 80, preferably 40 to 70%, stabilizer composition, the rest is a polymer compatible with the polymer to be stabilized.
Das Vermischen der Stabilisator-Kompositionen mit den zu stabilisierenden Polymeren wird nach üblichen Methoden durchgeführt, z.B. in geeigneten Mischern für geschmolzenes Material, in den Schmelzspinn- oder Folienblasmaschinen, im Extruder oder bei der Herstellung von Formgegenständen, Rohren, Fasern oder Schäumen. The mixing of the stabilizer compositions with the polymers to be stabilized is carried out by customary methods, e.g. in suitable mixers for molten material, in melt spinning or film blowing machines, in extruders or in the production of molded articles, tubes, fibers or foams.
In den folgenden Beispielen bedeuten, falls keine anderen Angaben vorliegen, die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben. Alle Reaktionen, bei denen AICI3 und/oder PCI3 anwesend ist, werden in einer Stickstoffatmosphäre, unter Aus-schuss von Sauerstoff und Feuchtigkeit durchgeführt. In the following examples, unless otherwise indicated, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius. All reactions in which AICI3 and / or PCI3 is present are carried out in a nitrogen atmosphere, with the exclusion of oxygen and moisture.
Beispiel 1 example 1
16,9 Teile Diphenyl, 38,5 Teile AICI3 und 58 Teile PCI3 werden intensiv gerührt und unter Rückfluss 6 Stunden auf 72 bis 74° erhitzt, wobei 5,6 Teile HCl gasförmig entstehen und abgeleitet werden. Die Reaktionsmasse wird sodann auf 55 bis 60° gekühlt und unter langsam auf ca. 80 mbar reduziertem Druck das überschüssige PCI3 abdestilliert. Man erhält so ein rötliches, klares Reaktionsprodukt, das sehr langsam, bei 80° einer Lösung von 145 Teilen 2,4-Bis-(1-phenyl-1'-methyläthyl)-phenol in 230 Teilen To-luol und 69 Teilen Pyridin zugefügt wird. Diese Mischung wird dann 4 Stunden bei 80° gerührt, der ungelöste Anteil der Reaktionsmischung erst bei 80° dann, nach Kühlung auf-10° abfiltriert und aus dem Filtrat das Lösungsmittel durch Destillation entfernt. Man erhält so ein gelbliches, glasartiges Produkt, 16.9 parts of diphenyl, 38.5 parts of AICI3 and 58 parts of PCI3 are stirred vigorously and heated under reflux at 72 to 74 ° for 6 hours, 5.6 parts of HCl being formed in gaseous form and being discharged. The reaction mass is then cooled to 55 to 60 ° and the excess PCI3 is distilled off under a pressure slowly reduced to about 80 mbar. This gives a reddish, clear reaction product which is added very slowly, at 80 °, to a solution of 145 parts of 2,4-bis (1-phenyl-1'-methylethyl) phenol in 230 parts of toluene and 69 parts of pyridine becomes. This mixture is then stirred for 4 hours at 80 °, the undissolved portion of the reaction mixture is then filtered off at 80 ° then, after cooling to -10 °, and the solvent is removed from the filtrate by distillation. This gives a yellowish, glassy product
7 7
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 679 862 A5 CH 679 862 A5
das, je nach den apparativen Bedingungen und den Bedingungen der Reaktionsführung (z.B. Rührgeschwindigkeit, Temperaturen) aus depending on the conditions of the equipment and the conditions of the reaction (e.g. stirring speed, temperatures)
0 bis 5 Mol.-% des Phenols der Formel 1a 0 to 5 mol% of the phenol of the formula 1a
R-OH (1a), R-OH (1a),
5 bis 15 MoI.-% des Phosphits der Formel 1b P(OR)3 (1b), 5 to 15 mol% of the phosphite of the formula 1b P (OR) 3 (1b),
10 bis 25 Mol.-% des Monophosphonits der Formel 1c 10 to 25 mol% of the monophosphonite of the formula 1c
(R0)2 P. (R0) 2 P.
(1c) (1c)
und 50 bis 75 Mol.-% des Diphosphonits der Formel 1d and 50 to 75 mol% of the diphosphonite of formula 1d
(R0)2R (R0) 2R
(OR)/ (OR) /
Od) Od)
besteht, wobei in den Formeln 1a bis 1d R eine Gruppe der Formel ist. exists, wherein in formulas 1a to 1d R is a group of the formula.
Das so erhaltene Produkt hat einen Schmelzpunkt von 83 bis 88° und einen Tropfpunkt von 93°. Es kann, z.B. durch Umkristallisieren (aus Dioxan oder Hexan) in seine Bestandteile aufgetrennt werden. The product thus obtained has a melting point of 83 to 88 ° and a dropping point of 93 °. It can e.g. can be separated into its constituents by recrystallization (from dioxane or hexane).
Beispiele 2 bis 22 Examples 2 to 22
Verfährt man wie im Beispiel 1 angegeben, setzt aber an Stelle von 2,4-Bis-(1'-phenyl-1'-methyläthyl)-phenol äquimolare Mengen der folgenden Verbindungen R-OH ein, erhält man ebenfalls Gemische der Verbindungen 1a bis 1d. If the procedure described in Example 1 is followed, but instead of 2,4-bis (1'-phenyl-1'-methylethyl) phenol, equimolar amounts of the following compounds R-OH are used, mixtures of compounds 1a to 1 are also obtained 1d.
8 8th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 679 862 A5 CH 679 862 A5
Tabelle 1 Table 1
Bsp. E.g.
R-OH RAW
2 2nd
2-tert.Octyl-4-methylphenyl 2-tert-octyl-4-methylphenyl
3 3rd
2,4-Di-tert.butyl-6-methylphenyl 2,4-di-tert-butyl-6-methylphenyl
4 4th
2-tert.Butylphenyl 2-tert-butylphenyl
5 5
2-Phenyl-phenyl 2-phenylphenyl
6 6
2- ( 1,1-Dime thylpropyl)phenyl 2- (1,1-dimethylpropyl) phenyl
7 7
2-Cyclohexyl phenyl 2-cyclohexyl phenyl
8 8th
2-tert.Butyl-4-phenyl-phenyl 2-tert-butyl-4-phenylphenyl
9 9
2-tert.Butyl-4-methylphenyl 2-tert-butyl-4-methylphenyl
10 10th
2,4-Dimethyl-6-tert.butylphenyl 2,4-dimethyl-6-tert-butylphenyl
11 11
2,4-Di-tert.butyl-6-ethylphenyl 2,4-di-tert-butyl-6-ethylphenyl
12 12
2,4-Diphenylphenyl 2,4-diphenylphenyl
13 13
2,4-Di-tert.octylphenyl 2,4-di-tert-octylphenyl
14 14
2-(1-Phenyl-l-methylethyl)phenyl 2- (1-phenyl-l-methylethyl) phenyl
15 15
2,4-Bis(1,1,-dime thylpropyl)phenyl 2,4-bis (1,1, -dimethylpropyl) phenyl
t.butyl t.butyl
16 16
—^5^—ch2ch2cooc8h1 7( i ) - ^ 5 ^ —ch2ch2cooc8h1 7 (i)
t^butyl t ^ butyl
17 17th
_^-ch2ch2cooch3 _ ^ - ch2ch2cooch3
t.butyl t.butyl
13 13
^OV— t.butyl ^ OV— t.butyl
co2ch3 co2ch3
9 9
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 679 862 A5 CH 679 862 A5
Bsp. E.g.
20 20th
R-OH RAW
t. butyl t. butyl
COOCgH17 (i) COOCgH17 (i)
21 21
22 22
ch3-co-n: ch3-co-n:
Beispiele 23-26 Examples 23-26
Verfährt man wie im Beispiel 1 angegeben, setzt aber an Stelle von 2,4-Bis-(1'-phenyl-1'-methyIäthyl)-phenol die halbe äquimolare Menge der bivalenten Phenole der folgenden Tabelle 2 ein, erhält man ein Gemisch von Verbindungen der Formeln 0 bis 5% der Verbindung der Formel 23a If the procedure is as described in Example 1, but instead of 2,4-bis (1'-phenyl-1'-methyl) phenol, half the equimolar amount of the bivalent phenols from Table 2 below is used, a mixture of Compounds of formulas 0 to 5% of the compound of formula 23a
R(OH)2 (23a), R (OH) 2 (23a),
5 bis 20% des Phosphits der Formel 23b 5 to 20% of the phosphite of formula 23b
(HO-Ri-O-)-P R (23b) (HO-Ri-O -) - P R (23b)
10 bis 20% des Monophosphonits der Formel 23c 10 to 20% of the monophosphonite of formula 23c
R R
0" ÌC-A /~\ (23c) 0 "ÌC-A / ~ \ (23c)
O O
und and
10 10th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 679 862 A5 CH 679 862 A5
50 bis 70% des Diphosphonits der Formel 23 50 to 70% of the diphosphonite of formula 23
(23d) (23d)
Bsp.No. E.g. no.
23 23
Tabelle 2 Table 2
cooch3 cooch3
t-butyl^ ili >butyl t-butyl ^ ili> butyl
SjÌoì SjÌoì
t-butyl t-butyl t-butyl t-butyl
24 24th
t-butyl t-butyl
t-butyl t-butyl t-butyl t-butyl
25 25th
ch- ch- ch- ch-
Beispiel 27 Example 27
a) 11,1 Teile Diphenyl, 25,4 Teile AICI3 und 37,7 Teile PCI3 werden unter Rückfluss und intensivem Rühren 6 Stunden auf 72 bis 74° erhitzt, wobei 4,1 Teile HCl entstehen. a) 11.1 parts of diphenyl, 25.4 parts of AICI3 and 37.7 parts of PCI3 are heated under reflux and vigorous stirring at 72 to 74 ° for 6 hours, producing 4.1 parts of HCl.
Bei 55 bis 60° wird der Oberschuss an PCI3 unter zunehmend vermindertem Druck (zuletzt 80 mbar) abdestilliert. At 55 to 60 ° the excess of PCI3 is distilled off under increasingly reduced pressure (finally 80 mbar).
11 11
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 679 862 A5 CH 679 862 A5
b) Dem Reaktionsprodukt werden 5,5 Teile PCI3 zugesetzt und das Gemisch sehr langsam einer 80° heissen Lösung von 66,8 Teilen 2-MethyI-6-tert. butylphenol in 160 Teilen Chlorbenzol und 54,4 Teilen Pyridin zugefügt. Man rührt 4 Stunden bei 80°, filtriert den unlöslichen Rückstand erst bei 80° dann, nach Kühlung, bei —10° ab, dampft das Lösungsmittel ab und erhält so ein Glas-ähnliches Produkt, das bei 62 bis 83° schmilzt, der Tropfpunkt ist bei 89°. b) 5.5 parts of PCI3 are added to the reaction product and the mixture is added very slowly to an 80 ° hot solution of 66.8 parts of 2-methyl-6-tert. butylphenol in 160 parts of chlorobenzene and 54.4 parts of pyridine. The mixture is stirred at 80 ° for 4 hours, the insoluble residue is filtered off only at 80 ° then, after cooling, at −10 °, the solvent is evaporated off and a glass-like product which melts at 62 to 83 ° is obtained, the dropping point is at 89 °.
Durch Umkristallisation kann das Reaktionsprodukt aufgetrennt werden, wobei man 0 bis 5 Mol.-% des Phenols der Formel 1a (Beispiel 1), 35 bis 45 Moi.-% des Phosphits der Formel 1b, 10 bis 20 Mol.-% des Monophosphonits der Formel 1c und 30 bis 40 Mol.-% des Diphosphonits der Formel 1d erhält, worin R 2-Methyl-6-tert.-butylphenyl bedeutet. The reaction product can be separated by recrystallization, 0 to 5 mol% of the phenol of the formula 1a (Example 1), 35 to 45 mol% of the phosphite of the formula 1b, 10 to 20 mol% of the monophosphonite of the Formula 1c and 30 to 40 mol% of the diphosphonite of formula 1d, in which R is 2-methyl-6-tert-butylphenyl.
Beispiele 28 bis 37 Examples 28-37
Man verfährt analog zu den Angaben im Beispiel 27, setzt aber an Stelle von 3-MethyI-6-tert.-butyl-phenol äquimolar Mengen der im folgenden angegebenen Phenole ein und erhält dabei ebenfalls Verbindungen der Formeln 1a bis 1d, worin R wieder den Phenylresten der eingesetzten Phenole entspricht. The procedure is analogous to that in Example 27, but instead of 3-methyl-6-tert-butylphenol, equimolar amounts of the phenols specified below are used, and compounds of the formulas 1a to 1d in which R is again the same are obtained Phenyl residues of the phenols used corresponds.
Tabelle 3 Table 3
Bsp.No. E.g. no.
Eingesetztes Phenol Phenol used
Schmelzpunkt Melting point
Tropfpunkt Dropping point
R-OH RAW
28 28
2-tert-ButyIphenol 2-tert-butylphenol
72-73° 72-73 °
99° 99 °
29 29
6-terL-Bulyl-3-methyI-phenol 6-terL-Bulyl-3-methyl-phenol
60° 60 °
70,8° 70.8 °
30 30th
6-tert-Butyl-2,4dimethyI-phenol 6-tert-butyl-2,4-dimethyl-phenol
90° 90 °
94,3° 94.3 °
31 31
2,6-di-sec.-ButyIphenoI 2,6-di-sec-butylphenol
ölig oily
67,0° 67.0 °
32 32
2-sec.-4-tert-Butylphenol 2-sec-4-tert-butylphenol
ölig oily
66,7° 66.7 °
33 33
2,4-di-terL-AmyIphenol 2,4-di-terL-AmyIphenol
55° 55 °
72,8É 72.8É
34 34
2-sec.-ButylphenoI 2-sec-butylphenol
ölig oily
30,0° 30.0 °
35 35
2-Isopropyl-phenol 2-isopropylphenol
ölig oily
30,3° 30.3 °
36 36
2,4-di-NonyI-phenol 2,4-di-nonylphenol
ölig oily
34,9° 34.9 °
37 37
2-tert.-Butyl-4-methyl-phenoI 2-tert-butyl-4-methylphenoI
60° 60 °
66° 66 °
Anwendunasbeisoiel Application example
Polypropylen-Proben (Hostalen PPK0160P) wurden einmal ohne Stabilisator (A), Polypropylene samples (Hostalen PPK0160P) were once without a stabilizer (A),
sowie je einmal mit 0,1% Calzium Stearat und 0,1% Pentärythrol-tetrakis-(3,5-di-tert.-butyl-4-hydroxy-phenyl) (B), and once each with 0.1% calcium stearate and 0.1% pentärythrol tetrakis (3,5-di-tert-butyl-4-hydroxyphenyl) (B),
mit 0,1% Calzium-Stearat, 0,1% Pentärythrol-tetrakis-(3,5-di-tert. Butyl-4-hydroxyphenyl) und 0,1% der Komposition gemäss Beispiel 1(C) und mit 0,1% Calzium-Stearat, 0,1% Pentärythrol-tetrakis-(3,5-di-tert.-Butyl-4-hydroxyphenyl und 0,1% des Stabilisators gemäss Beispiel 9 der CH-PS 542 249 (Handelsprodukt «Sandostab PEPQ») (D) versetzt und jeweils in einem Göttfert Extrusiometer (mit einer 20-mm-Schnecke, Kompression 1:3, Durchmesser:Länge, d:1=1:20) bei 270° mehrmals extrudiert, wobei nach dem 1., dem 3. und dem 5. Durchgang der Melt-Flow-Index MFI und der Yellowness-Index gemessen wurden: with 0.1% calcium stearate, 0.1% pentärythrol tetrakis (3,5-di-tert. butyl-4-hydroxyphenyl) and 0.1% of the composition according to Example 1 (C) and with 0.1 % Calcium stearate, 0.1% pentärythrol tetrakis (3,5-di-tert-butyl-4-hydroxyphenyl and 0.1% of the stabilizer according to Example 9 of CH-PS 542 249 (commercial product "Sandostab PEPQ" ) (D) and extruded each time in a Göttfert extrusiometer (with a 20 mm screw, compression 1: 3, diameter: length, d: 1 = 1: 20) at 270 °, whereby after the 1st, the 3rd and 5th round the Melt Flow Index MFI and the Yellowness Index were measured:
Yellowness-Index Yellowness index
MFI, Durchgänge Durchgänge MFI, passages passages
Probe sample
1 1
3 3rd
5 5
1 1
3 3rd
5 5
A A
2.8 2.8
4.7 4.7
6.9 6.9
3.8 3.8
7.2 7.2
9.8 9.8
B B
1.8 1.8
2.7 2.7
4.1 4.1
3.5 3.5
9.3 9.3
12.4 12.4
C C.
0.9 0.9
1.1 1.1
1.4 1.4
4.6 4.6
8.0 8.0
10.2 10.2
D D
1.0 1.0
1.5 1.5
2.0 2.0
2.6 2.6
10.7 10.7
17.0 17.0
Wie aus der obigen Tabelle leicht ersichtlich, weist die Probe C mit dem erfindunssgemässen Stabilisator, insgesamt die besten Werte auf. Auch bei der Anwendung der übrigen, erfindungsgemässen Stabilisator-Kompositionen erhält man ähnlich gute Werte. As can easily be seen from the table above, sample C with the stabilizer according to the invention has the best overall values. Similarly good values are also obtained when the other stabilizer compositions according to the invention are used.
12 12
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 679 862 A5 CH 679 862 A5
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898901517A GB8901517D0 (en) | 1989-01-24 | 1989-01-24 | Improvements in or relating to organic compounds |
CN90100728.5A CN1054083A (en) | 1989-01-24 | 1990-02-16 | Phosphonite compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
CH679862A5 true CH679862A5 (en) | 1992-04-30 |
Family
ID=36754787
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH207/90A CH679862A5 (en) | 1989-01-24 | 1990-01-23 |
Country Status (12)
Country | Link |
---|---|
JP (1) | JPH02270892A (en) |
CN (1) | CN1054083A (en) |
BE (1) | BE1003823A3 (en) |
CA (1) | CA2008376A1 (en) |
CH (1) | CH679862A5 (en) |
DD (1) | DD291772A5 (en) |
DE (1) | DE4001397A1 (en) |
FR (2) | FR2642081B1 (en) |
GB (2) | GB8901517D0 (en) |
HU (1) | HUT54380A (en) |
IT (1) | IT1241397B (en) |
NL (1) | NL9000170A (en) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1231769B (en) * | 1989-08-02 | 1991-12-21 | Himont Inc | PROCEDURE FOR THE STABILIZATION OF POLYOLEFINS AND PRODUCTS OBTAINED FROM IT. |
GB2247241A (en) * | 1990-08-22 | 1992-02-26 | Sandoz Ltd | Stabilising composition for filled polymeric materials |
TW209224B (en) * | 1991-05-27 | 1993-07-11 | Yoshitomi Pharmaceutical | |
FR2679913A1 (en) * | 1991-07-17 | 1993-02-05 | Sandoz Sa | NOVEL COMPOSITIONS ENHANCING THE STABILITY OF POLYMER MATERIALS FOR TRANSFORMATION. |
GB2261667A (en) * | 1991-11-20 | 1993-05-26 | Sandoz Ltd | Stabilized polymeric compositions |
GB2263280B (en) * | 1992-01-17 | 1996-07-31 | Sandoz Ltd | Use of a phosphonite and optionally a phosphite for clarifying propylene polymers |
GB2265377B (en) * | 1992-03-11 | 1996-07-31 | Sandoz Ltd | The use of phosphonite-HALS and phosphite-HALS compounds for the stabilisation of polyolefins |
US5616636A (en) * | 1992-03-11 | 1997-04-01 | Sandoz Ltd. | Phosphonite-hals and phosphite-hals compounds as stabilizers |
JP2525319B2 (en) * | 1992-04-08 | 1996-08-21 | チッソ株式会社 | Crystalline polyolefin composition |
US5703150A (en) * | 1994-12-28 | 1997-12-30 | Yoshitomi Pharmaceutical Industries, Ltd. | Phosphonite or phosphonate compounds and use thereof |
DE19647297A1 (en) | 1996-11-15 | 1998-05-20 | Basf Ag | Thermo-stable thermoplastic molding compounds |
KR100563947B1 (en) * | 1998-09-01 | 2006-03-29 | 클라리언트 파이넌스 (비브이아이)리미티드 | Process for the production of phosphor organic compounds |
TW500727B (en) * | 1999-11-02 | 2002-09-01 | Ciba Sc Holding Ag | Process for the preparation of low chloride stabilisers |
TWI226351B (en) * | 2000-07-14 | 2005-01-11 | Clariant Int Ltd | Synergistic mixtures of phosphorus-containing compounds for stabilizing polymers |
DK1910455T3 (en) | 2005-07-21 | 2012-11-19 | Basf Se | Stabilization of Polyolefins with Liquid Tris (Monoalkyl) Phenyl Phosphites |
US8008384B2 (en) | 2006-06-20 | 2011-08-30 | Chemtura Corporation | Liquid butylaryl phosphite compositions |
US8008383B2 (en) | 2006-06-20 | 2011-08-30 | Chemtura Corporation | Liquid amylaryl phosphite compositions |
US7947769B2 (en) | 2006-06-20 | 2011-05-24 | Chemtura Corporation | Liquid amylaryl phosphite compositions and alkylate compositions for manufacturing same |
US8178005B2 (en) | 2006-06-20 | 2012-05-15 | Chemtura Corporation | Liquid phosphite compositions having different alkyl groups |
US7888414B2 (en) * | 2006-06-20 | 2011-02-15 | Chemtura Corporation | Liquid phosphite blends as stabilizers |
US8183311B2 (en) | 2006-06-20 | 2012-05-22 | Chemtura Corporation | Liquid phosphite composition derived from cresols |
US8188170B2 (en) | 2006-06-20 | 2012-05-29 | Chemtura Corporation | Polymers with low gel content and enhanced gas-fading |
GB201812145D0 (en) | 2018-07-25 | 2018-09-05 | Addivant Switzerland Gmbh | Composition |
GB2591482A (en) | 2020-01-29 | 2021-08-04 | Si Group Switzerland Chaa Gmbh | Non-dust blend |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE791767A (en) * | 1971-11-24 | 1973-05-22 | Sandoz Sa | NEW ORGANIC DERIVATIVES OF TRIVALENT PHOSPHORUS FOR USE AS ORGANIC STABILIZERS AND THEIR PREPARATION |
JPS56125448A (en) * | 1980-03-10 | 1981-10-01 | Mitsubishi Gas Chem Co Inc | Polyphenylene ether resin composition |
CA1276344C (en) * | 1980-12-17 | 1990-11-13 | Markus Matzner | Processing of heat stabilized polyarylates |
FR2557882B1 (en) * | 1984-01-06 | 1986-05-02 | Solvay | STABILIZED COMPOSITIONS BASED ON ALPHA-OLEFIN POLYMERS |
GB8803439D0 (en) * | 1988-02-15 | 1988-03-16 | Sandoz Ltd | Improvements in/relating to organic compounds |
-
1989
- 1989-01-24 GB GB898901517A patent/GB8901517D0/en active Pending
-
1990
- 1990-01-16 HU HU90150A patent/HUT54380A/en unknown
- 1990-01-19 DE DE4001397A patent/DE4001397A1/en not_active Withdrawn
- 1990-01-22 GB GB9001399A patent/GB2227490B/en not_active Expired - Fee Related
- 1990-01-23 DD DD90337279A patent/DD291772A5/en not_active IP Right Cessation
- 1990-01-23 CA CA002008376A patent/CA2008376A1/en not_active Abandoned
- 1990-01-23 BE BE9000077A patent/BE1003823A3/en not_active IP Right Cessation
- 1990-01-23 CH CH207/90A patent/CH679862A5/de not_active IP Right Cessation
- 1990-01-23 FR FR909000829A patent/FR2642081B1/en not_active Expired - Lifetime
- 1990-01-24 IT IT47565A patent/IT1241397B/en active IP Right Grant
- 1990-01-24 JP JP2012748A patent/JPH02270892A/en active Pending
- 1990-01-24 NL NL9000170A patent/NL9000170A/en not_active Application Discontinuation
- 1990-02-16 CN CN90100728.5A patent/CN1054083A/en active Pending
- 1990-05-10 FR FR9006013A patent/FR2644457B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
GB2227490B (en) | 1993-01-06 |
HU900150D0 (en) | 1990-03-28 |
FR2644457B1 (en) | 1993-10-22 |
FR2644457A1 (en) | 1990-09-21 |
JPH02270892A (en) | 1990-11-05 |
GB2227490A (en) | 1990-08-01 |
IT1241397B (en) | 1994-01-10 |
FR2642081A1 (en) | 1990-07-27 |
CA2008376A1 (en) | 1990-07-24 |
DE4001397A1 (en) | 1990-07-26 |
CN1054083A (en) | 1991-08-28 |
HUT54380A (en) | 1991-02-28 |
FR2642081B1 (en) | 1992-03-06 |
IT9047565A0 (en) | 1990-01-24 |
IT9047565A1 (en) | 1991-07-24 |
GB8901517D0 (en) | 1989-03-15 |
NL9000170A (en) | 1990-08-16 |
DD291772A5 (en) | 1991-07-11 |
GB9001399D0 (en) | 1990-03-21 |
BE1003823A3 (en) | 1992-06-23 |
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