KR101605571B1 - 스티렌계 폴리머를 위한 첨가제 혼합물 - Google Patents
스티렌계 폴리머를 위한 첨가제 혼합물 Download PDFInfo
- Publication number
- KR101605571B1 KR101605571B1 KR1020107017419A KR20107017419A KR101605571B1 KR 101605571 B1 KR101605571 B1 KR 101605571B1 KR 1020107017419 A KR1020107017419 A KR 1020107017419A KR 20107017419 A KR20107017419 A KR 20107017419A KR 101605571 B1 KR101605571 B1 KR 101605571B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- substituted
- hydrogen
- phenyl
- phenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 229920000642 polymer Polymers 0.000 title claims abstract description 44
- 239000000654 additive Substances 0.000 title claims description 26
- 230000000996 additive effect Effects 0.000 title claims description 10
- -1 phenol thioether Chemical class 0.000 claims abstract description 288
- 238000000034 method Methods 0.000 claims abstract description 25
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 40
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 5
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000012815 thermoplastic material Substances 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 24
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000001118 alkylidene group Chemical group 0.000 description 8
- 239000012964 benzotriazole Substances 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000004956 cyclohexylene group Chemical group 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 0 *C1=C(*)C(CS*)=C(O)I=C1 Chemical compound *C1=C(*)C(CS*)=C(O)I=C1 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000007765 extrusion coating Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001955 polyphenylene ether Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000009182 swimming Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
- BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical compound S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 2
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- VTFXHGBOGGGYDO-UHFFFAOYSA-N 2,4-bis(dodecylsulfanylmethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCC)=C1 VTFXHGBOGGGYDO-UHFFFAOYSA-N 0.000 description 2
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 2
- QLMGIWHWWWXXME-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C1=CC(CC(O)=O)=CC(C(C)(C)C)=C1O QLMGIWHWWWXXME-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 2
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 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
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical class [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Chemical class 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical class [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- NECLQTPQJZSWOE-UHFFFAOYSA-N spiro[5.5]undecane Chemical compound C1CCCCC21CCCCC2 NECLQTPQJZSWOE-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002983 wood substitute Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/006—Removal of residual monomers by chemical reaction, e.g. scavenging
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- 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
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2425/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
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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)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
Claims (17)
- 스티렌계 폴리머의 제조 및 가공 동안 포화 또는 불포화 모노머 및 올리고머의 양을 감소시키는 방법으로서, 상기 방법은 스티렌계 폴리머에 a) 페놀 티오에테르, b) 페놀 아크릴레이트, c) 3-아릴벤조푸란-2-온 및 d) 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 2 이상의 성분으로 된 혼합물을 첨가하는 것을 포함하고,
단, 페놀 티오에테르 및 페놀 아크릴레이트를 포함하는 혼합물은, 3-아릴벤조푸란-2-온 또는 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 제3 성분을 적어도 함유하는 것이며,
여기서, 성분 a)는 하기 화학식 I의 화합물이고;
상기 식 중,
R1은 수소, C1-C20알킬, 스티릴, α-메틸-스티릴 또는 -CH2-S-R3; 또는 C2-C20알케닐, C3-C20알키닐, C5-C9시클로알킬, 페닐 또는 톨릴에 의해 치환된 C1-C20알킬이며,
R2는 C1-C20알킬 또는 -CH2-S-R3이고,
R3은 C1-C20알킬; 페닐, 히드록실, 시아노, 포르밀, 아세틸 또는 -0-CO-R5에 의해 치환된 C1-C20알킬; C2-C20알케닐, C3-C20알키닐, C5-C9시클로알킬; 또는 히드록실, 페닐, 4-클로로페닐, 2-메톡시카르보닐페닐, p-톨릴, 1,3-벤즈티아졸-2-일, -(CHR5)nCOOR6 또는 -(CHR5)nCONR7R8에 의해 치환된 C5-C9시클로알킬이며,
R4는 수소 또는 메틸이고,
R5는 수소 또는 C1-C6알킬이며,
R6은 C1-C20알킬; 산소 또는 황이 개입된 C3-C20알킬; C5-C9시클로알킬, 페닐, 벤질 또는 톨릴이고,
R7 및 R8은 서로 독립적으로 수소 또는 C1-C6알킬이며, 그리고
n은 1 또는 2이고;
성분 b)는 하기 화학식 II의 화합물이며;
상기 식 중,
R11 및 R12는 서로 독립적으로 C1-C25알킬; C1-C4알킬에 의해 치환 또는 비치환된 C5-C12시클로알킬; C7-C9페닐알킬; 또는 C1-C4알킬에 의해 치환 또는 비치환된 페닐이고,
R13은 수소 또는 메틸이며,
R14는 수소 또는 C1-C8알킬이고,
R15는 C1-C25알킬; 산소, 황 또는 이 개입된 C2-C25알킬; C2-C24알케닐; 페닐 고리 상에서 할로겐, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오에 의해 치환 또는 비치환된 C8-C30페닐알케닐; C1-C4알킬에 의해 치환 또는 비치환된 C5-C12시클로알킬; 페닐 고리 상에서 할로겐, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오에 의해 치환 또는 비치환된 C8-C30페닐알킬; 또는 할로겐, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오에 의해 치환 또는 비치환된 페닐이며,
R16은 수소 또는 C1-C18알킬이고;
성분 d)는 하기 화학식 A-1, A-2a 또는 A-2b의 화합물인 것인 방법:
- 제1항에 있어서, 성분 a), b), c) 및 d) 이외의 추가 첨가제를 포함하는 방법.
- 제3항에 있어서, 추가 첨가제로서 광 안정화제, 산 스캐빈저 및/또는 대전방지제를 포함하는 방법.
- 제1항에 있어서, 2 이상의 성분으로 된 혼합물은 스티렌계 폴리머의 중량을 기준으로 하여 0.001 내지 5%의 양으로 존재하는 것인 방법.
- 스티렌계 폴리머의 제조 및 가공 동안에 포화 또는 불포화 모노머 및 올리고머의 양을 감소시키기 위한 혼합물로서, a) 제1항에서 정의된 페놀 티오에테르, b) 제1항에서 정의된 페놀 아크릴레이트, c) 3-아릴벤조푸란-2-온 및 d) 제1항에서 정의된 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 2 이상의 성분으로 된 혼합물을 포함하고,
단, 페놀 티오에테르 및 페놀 아크릴레이트를 포함하는 혼합물은, 3-아릴벤조푸란-2-온 또는 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 제3 성분을 적어도 함유하는 것인 혼합물. - 제6항에 있어서, 단, 페놀 티오에테르 및 페놀 아크릴레이트를 포함하는 혼합물은 배제되는 것인 혼합물.
- (i) 스티렌계 폴리머, 및
(ii) a) 제1항에서 정의된 페놀 티오에테르, b) 제1항에서 정의된 페놀 아크릴레이트, c) 3-아릴벤조푸란-2-온 및 d) 제1항에서 정의된 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 2 이상의 성분으로 된 첨가제 혼합물로서,
단, 페놀 티오에테르 및 페놀 아크릴레이트를 포함하는 혼합물은, 3-아릴벤조푸란-2-온 또는 1,1-이중 치환된 에틸렌 또는 삼중 치환된 에틸렌으로 이루어진 군으로부터 선택된 제3 성분을 적어도 함유하는 것인 첨가제 혼합물
을 포함하는 조성물. - 제8항에 있어서, 페놀 티오에테르 및 페놀 아크릴레이트를 포함하는 혼합물을 함유하지 않는 조성물.
- 제8항 또는 제9항에 있어서, 성분 (i) 및 (ii) 이외에도 추가 첨가제를 포함하는 조성물.
- 제6항 또는 제7항에 따른 첨가제 혼합물과, 스티렌계 폴리머와 동일하거나 상용성인 열가소성 물질을 포함하는 마스터배치 조성물.
- 제11항에 있어서, 상기 열가소성 물질 10 내지 80 중량%를 포함하는 마스터배치 조성물.
- 제6항 또는 제7항에 따른 혼합물을 함유하는 성형 물품.
- 스티렌계 폴리머의 제조 및 가공 동안에 포화 또는 불포화 모노머 및 올리고머의 양을 감소시키기는 데 제6항에 따른 혼합물을 이용하는 방법.
- 삭제
- 삭제
- 삭제
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CH644835A5 (de) | 1978-12-06 | 1984-08-31 | Asahi Chemical Ind | Monoesterverbindungen von alkyliden-bis-(4,6-disubstituiertem phenol). |
JPS5884835A (ja) | 1981-11-17 | 1983-05-21 | Sumitomo Chem Co Ltd | 安定化合成ゴム組成物 |
US4562281A (en) | 1983-12-14 | 1985-12-31 | Sumitomo Chemical Company, Limited | Production of bisphenol derivatives |
US4774274A (en) | 1986-06-25 | 1988-09-27 | Sumitomo Chemical Company, Limited | Thermally stabilized butadiene resins containing a hindered phenolic acrylate or methacrylate |
CA2060787C (en) | 1991-02-18 | 2002-07-02 | Kikumitsu Inoue | Production of bisphenol monoester |
CH686306A5 (de) | 1993-09-17 | 1996-02-29 | Ciba Geigy Ag | 3-Aryl-benzofuranone als Stabilisatoren. |
DE4414043A1 (de) * | 1994-04-22 | 1995-10-26 | Basf Ag | Stabilisierung von Polystyrol durch phenolische Stabilisatoren |
TW303381B (ko) | 1994-12-05 | 1997-04-21 | Ciba Sc Holding Ag | |
EP0727410A1 (de) | 1995-02-08 | 1996-08-21 | Ciba-Geigy Ag | Bisphenolesterderivate |
JPH1171489A (ja) * | 1997-06-24 | 1999-03-16 | Asahi Chem Ind Co Ltd | ゴム補強スチレン系樹脂組成物 |
DE59806917D1 (de) * | 1997-09-29 | 2003-02-20 | Ciba Sc Holding Ag | Stabilisatorgemisch für organische Materialien |
AU7577900A (en) * | 1999-09-10 | 2001-04-10 | Kt Holdings, Llc | Novel polymer additives for forming objects |
TW491833B (en) | 2000-01-10 | 2002-06-21 | Ciba Sc Holding Ag | Improved process for the preparation of mercaptomethylphenols |
DE60131363T2 (de) * | 2000-05-25 | 2008-09-04 | Asahi Kasei Kabushiki Kaisha | Blockcopolymer und zusammensetzung daraus |
DE10055942A1 (de) * | 2000-11-10 | 2002-06-06 | Tesa Ag | Haftklebemasse und ihre Verwendung |
JP4703039B2 (ja) * | 2001-06-20 | 2011-06-15 | 日本エラストマー株式会社 | ブロック共重合体組成物 |
TW593303B (en) | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
WO2006024611A2 (en) | 2004-08-31 | 2006-03-09 | Ciba Specialty Chemicals Holding Inc. | Stabilization of organic materials |
JP5008566B2 (ja) * | 2004-08-31 | 2012-08-22 | チバ ホールディング インコーポレーテッド | 有機材料の安定化 |
-
2009
- 2009-01-19 KR KR1020107017419A patent/KR101605571B1/ko not_active Expired - Fee Related
- 2009-01-19 CN CN200980103307.1A patent/CN101970559B/zh not_active Expired - Fee Related
- 2009-01-19 EP EP09705627A patent/EP2238199B1/en not_active Not-in-force
- 2009-01-19 AT AT09705627T patent/ATE522569T1/de not_active IP Right Cessation
- 2009-01-19 JP JP2010544662A patent/JP5677853B2/ja not_active Expired - Fee Related
- 2009-01-19 ES ES09705627T patent/ES2372567T3/es active Active
- 2009-01-19 WO PCT/EP2009/050539 patent/WO2009095328A1/en active Application Filing
- 2009-01-19 US US12/747,547 patent/US8569405B2/en active Active
- 2009-01-22 TW TW098102465A patent/TWI465499B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
TWI465499B (zh) | 2014-12-21 |
TW200948876A (en) | 2009-12-01 |
EP2238199A1 (en) | 2010-10-13 |
KR20100117595A (ko) | 2010-11-03 |
EP2238199B1 (en) | 2011-08-31 |
JP2011511114A (ja) | 2011-04-07 |
ATE522569T1 (de) | 2011-09-15 |
US20110046278A1 (en) | 2011-02-24 |
CN101970559B (zh) | 2014-03-05 |
CN101970559A (zh) | 2011-02-09 |
US8569405B2 (en) | 2013-10-29 |
ES2372567T3 (es) | 2012-01-23 |
WO2009095328A1 (en) | 2009-08-06 |
JP5677853B2 (ja) | 2015-02-25 |
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