DE69404046T2 - Pfropfvorläufer und Verfahren zur Herstellung von gepfropften aromatischen Polycarbonaten - Google Patents
Pfropfvorläufer und Verfahren zur Herstellung von gepfropften aromatischen PolycarbonatenInfo
- Publication number
- DE69404046T2 DE69404046T2 DE69404046T DE69404046T DE69404046T2 DE 69404046 T2 DE69404046 T2 DE 69404046T2 DE 69404046 T DE69404046 T DE 69404046T DE 69404046 T DE69404046 T DE 69404046T DE 69404046 T2 DE69404046 T2 DE 69404046T2
- Authority
- DE
- Germany
- Prior art keywords
- polycarbonate resin
- aromatic polycarbonate
- weight
- carbon atoms
- carbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 80
- 239000002243 precursor Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 31
- 239000004417 polycarbonate Substances 0.000 title description 12
- 229920000515 polycarbonate Polymers 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 229920005668 polycarbonate resin Polymers 0.000 claims description 83
- 239000004431 polycarbonate resin Substances 0.000 claims description 83
- 239000000178 monomer Substances 0.000 claims description 53
- 229920002554 vinyl polymer Polymers 0.000 claims description 47
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 42
- 150000001451 organic peroxides Chemical class 0.000 claims description 41
- 239000007870 radical polymerization initiator Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000002245 particle Substances 0.000 claims description 19
- 238000005470 impregnation Methods 0.000 claims description 16
- 238000000354 decomposition reaction Methods 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 239000007900 aqueous suspension Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000004898 kneading Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 229920001567 vinyl ester resin Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical group O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 25
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000003287 optical effect Effects 0.000 description 18
- 239000008188 pellet Substances 0.000 description 18
- -1 polypropylene Polymers 0.000 description 16
- 125000002348 vinylic group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- BMPPHGZRHQWRFX-UHFFFAOYSA-N (1-tert-butylperoxy-2-carboxyoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(COC(O)=O)OOC(C)(C)C BMPPHGZRHQWRFX-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 238000010559 graft polymerization reaction Methods 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- YTEAHQIOWUNLTP-UHFFFAOYSA-N 2-carboxyoxyethyl 3-tert-butylperoxyprop-2-enoate Chemical compound CC(C)(C)OOC=CC(=O)OCCOC(O)=O YTEAHQIOWUNLTP-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- FNMTVMWFISHPEV-AATRIKPKSA-N dipropan-2-yl (e)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C\C(=O)OC(C)C FNMTVMWFISHPEV-AATRIKPKSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002898 organic sulfur compounds Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LGTYQJIJDFPOPA-UHFFFAOYSA-N (1-tert-butylperoxy-2-carboxyoxypropan-2-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(OC(O)=O)COOC(C)(C)C LGTYQJIJDFPOPA-UHFFFAOYSA-N 0.000 description 1
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- PSGRWTHSGKHGEC-UHFFFAOYSA-N (2-prop-1-en-2-ylphenyl) carbonochloridate Chemical compound CC(=C)C1=CC=CC=C1OC(Cl)=O PSGRWTHSGKHGEC-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ZORJPNCZZRLEDF-UHFFFAOYSA-N (3-methoxy-3-methylbutoxy)carbonyloxy (3-methoxy-3-methylbutyl) carbonate Chemical compound COC(C)(C)CCOC(=O)OOC(=O)OCCC(C)(C)OC ZORJPNCZZRLEDF-UHFFFAOYSA-N 0.000 description 1
- NLBJAOHLJABDAU-UHFFFAOYSA-N (3-methylbenzoyl) 3-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC(C(=O)OOC(=O)C=2C=C(C)C=CC=2)=C1 NLBJAOHLJABDAU-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- AQOSPGCCTHGZFL-UHFFFAOYSA-N 1-(3a-hydroxy-7-methoxy-1,2,4,8b-tetrahydropyrrolo[2,3-b]indol-3-yl)ethanone Chemical compound COC1=CC=C2NC3(O)N(C(C)=O)CCC3C2=C1 AQOSPGCCTHGZFL-UHFFFAOYSA-N 0.000 description 1
- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- HUOBWFKCWUVATL-UHFFFAOYSA-N 1-butyl-2-ethenylbenzene Chemical compound CCCCC1=CC=CC=C1C=C HUOBWFKCWUVATL-UHFFFAOYSA-N 0.000 description 1
- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- FBPVUBVZRPURIU-UHFFFAOYSA-N 1-hexylpyrrole-2,5-dione Chemical compound CCCCCCN1C(=O)C=CC1=O FBPVUBVZRPURIU-UHFFFAOYSA-N 0.000 description 1
- PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- YEKDUBMGZZTUDY-UHFFFAOYSA-N 1-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)N1C(=O)C=CC1=O YEKDUBMGZZTUDY-UHFFFAOYSA-N 0.000 description 1
- LGDKZTWUKPJMHD-UHFFFAOYSA-N 2-(1-tert-butylperoxy-2-carboxyoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(COC(=O)O)OOC(C)(C)C LGDKZTWUKPJMHD-UHFFFAOYSA-N 0.000 description 1
- KJJSFOGJWFNOTH-UHFFFAOYSA-N 2-(2-carboxyoxyethoxy)ethyl 3-(2,4,4-trimethylpentan-2-ylperoxy)prop-2-enoate Chemical compound CC(C)(C)CC(C)(C)OOC=CC(=O)OCCOCCOC(=O)O KJJSFOGJWFNOTH-UHFFFAOYSA-N 0.000 description 1
- BISXWFRRRLAYIJ-UHFFFAOYSA-N 2-(2-carboxyoxyethoxy)ethyl 3-(2-methylbutan-2-ylperoxy)prop-2-enoate Chemical compound CCC(C)(C)OOC=CC(=O)OCCOCCOC(=O)O BISXWFRRRLAYIJ-UHFFFAOYSA-N 0.000 description 1
- LZEZCPMWDKWWNU-UHFFFAOYSA-N 2-(2-carboxyoxyethoxy)ethyl 3-[2-(4-propan-2-ylphenyl)propan-2-ylperoxy]prop-2-enoate Chemical compound CC(C)C1=CC=C(C=C1)C(C)(C)OOC=CC(=O)OCCOCCOC(=O)O LZEZCPMWDKWWNU-UHFFFAOYSA-N 0.000 description 1
- ANHMUEBVHTUWHS-UHFFFAOYSA-N 2-(2-carboxyoxyethoxy)ethyl 3-tert-butylperoxyprop-2-enoate Chemical compound CC(C)(C)OOC=CC(=O)OCCOCCOC(=O)O ANHMUEBVHTUWHS-UHFFFAOYSA-N 0.000 description 1
- AJRRUHVEWQXOLO-UHFFFAOYSA-N 2-(fluoroamino)acetic acid Chemical compound OC(=O)CNF AJRRUHVEWQXOLO-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XNMYXBYSRGTOIG-UHFFFAOYSA-N 2-[2-carboxyoxy-1-(2,4,4-trimethylpentan-2-ylperoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(COC(=O)O)OOC(C)(C)CC(C)(C)C XNMYXBYSRGTOIG-UHFFFAOYSA-N 0.000 description 1
- SSPOMAAFIHTOHM-UHFFFAOYSA-N 2-[2-carboxyoxy-1-(2-methylbutan-2-ylperoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CCC(C)(C)OOC(COC(=O)O)OCCOC(=O)C(=C)C SSPOMAAFIHTOHM-UHFFFAOYSA-N 0.000 description 1
- GICYNLZZSDMSNC-UHFFFAOYSA-N 2-[2-carboxyoxy-1-(2-methylpentan-2-ylperoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CCCC(C)(C)OOC(COC(=O)O)OCCOC(=O)C(=C)C GICYNLZZSDMSNC-UHFFFAOYSA-N 0.000 description 1
- QYMFORJOEJUFNT-UHFFFAOYSA-N 2-[2-carboxyoxy-1-[2-(4-propan-2-ylphenyl)propan-2-ylperoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(C)C1=CC=C(C=C1)C(C)(C)OOC(COC(=O)O)OCCOC(=O)C(=C)C QYMFORJOEJUFNT-UHFFFAOYSA-N 0.000 description 1
- NZQYTVCGWJZBKK-UHFFFAOYSA-N 2-carboxyoxyethyl 3-(2,4,4-trimethylpentan-2-ylperoxy)prop-2-enoate Chemical compound CC(C)(C)CC(C)(C)OOC=CC(=O)OCCOC(O)=O NZQYTVCGWJZBKK-UHFFFAOYSA-N 0.000 description 1
- HHEFLONTMRYHPK-UHFFFAOYSA-N 2-carboxyoxyethyl 3-(2-methylbutan-2-ylperoxy)prop-2-enoate Chemical compound CCC(C)(C)OOC=CC(=O)OCCOC(O)=O HHEFLONTMRYHPK-UHFFFAOYSA-N 0.000 description 1
- JTCDBWDDCRFJFF-UHFFFAOYSA-N 2-carboxyoxyethyl 3-[2-(4-propan-2-ylphenyl)propan-2-ylperoxy]prop-2-enoate Chemical compound CC(C)C1=CC=C(C=C1)C(C)(C)OOC=CC(=O)OCCOC(=O)O JTCDBWDDCRFJFF-UHFFFAOYSA-N 0.000 description 1
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- 229920005992 thermoplastic resin Polymers 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/36—Per-compounds with more than one peroxy radical
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/02—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonates or saturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2992693 | 1993-01-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69404046D1 DE69404046D1 (de) | 1997-08-14 |
| DE69404046T2 true DE69404046T2 (de) | 1997-11-20 |
Family
ID=12289603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69404046T Expired - Fee Related DE69404046T2 (de) | 1993-01-26 | 1994-01-26 | Pfropfvorläufer und Verfahren zur Herstellung von gepfropften aromatischen Polycarbonaten |
Country Status (5)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8637127B2 (en) | 2005-06-27 | 2014-01-28 | Kennametal Inc. | Composite article with coolant channels and tool fabrication method |
| ATE512278T1 (de) | 2006-04-27 | 2011-06-15 | Tdy Ind Inc | Modulare erdbohrmeissel mit fixiertem schneider und modulare erdbohrmeisselkörper mit fixiertem schneider |
| CN102764893B (zh) | 2006-10-25 | 2015-06-17 | 肯纳金属公司 | 具有改进的抗热开裂性的制品 |
| US8790439B2 (en) | 2008-06-02 | 2014-07-29 | Kennametal Inc. | Composite sintered powder metal articles |
| US8025112B2 (en) | 2008-08-22 | 2011-09-27 | Tdy Industries, Inc. | Earth-boring bits and other parts including cemented carbide |
| US9050673B2 (en) * | 2009-06-19 | 2015-06-09 | Extreme Surface Protection Ltd. | Multilayer overlays and methods for applying multilayer overlays |
| US9643236B2 (en) | 2009-11-11 | 2017-05-09 | Landis Solutions Llc | Thread rolling die and method of making same |
| US8800848B2 (en) | 2011-08-31 | 2014-08-12 | Kennametal Inc. | Methods of forming wear resistant layers on metallic surfaces |
| US9016406B2 (en) | 2011-09-22 | 2015-04-28 | Kennametal Inc. | Cutting inserts for earth-boring bits |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331796A (en) * | 1976-09-04 | 1978-03-25 | Mitsubishi Petrochem Co Ltd | Production of modified poly-carbonate resin particles |
| JPS54117555A (en) * | 1978-03-03 | 1979-09-12 | Mitsubishi Petrochem Co Ltd | Improved polycarbonate resin composition |
| JPS5532298A (en) * | 1978-08-28 | 1980-03-06 | Mca Disco Vision | Producing video disk structure |
| JPS58180553A (ja) * | 1982-04-19 | 1983-10-22 | Idemitsu Petrochem Co Ltd | 光学機器用成形素材 |
| JPS62138514A (ja) * | 1985-12-11 | 1987-06-22 | Hitachi Chem Co Ltd | 光学用樹脂材料 |
| JPH06102702B2 (ja) * | 1987-01-31 | 1994-12-14 | 日本油脂株式会社 | グラフト化前駆体及びその製造方法 |
| JP2586025B2 (ja) * | 1987-02-12 | 1997-02-26 | 三菱瓦斯化学株式会社 | グラフトポリカ−ボネ−ト樹脂組成物． |
| JPH0651767B2 (ja) * | 1987-02-18 | 1994-07-06 | 日本油脂株式会社 | グラフト樹脂組成物の製造方法 |
| JPS63312305A (ja) * | 1987-06-16 | 1988-12-20 | Nippon Oil & Fats Co Ltd | グラフト樹脂組成物の製造方法 |
| JPS63312306A (ja) * | 1987-06-16 | 1988-12-20 | Nippon Oil & Fats Co Ltd | グラフト樹脂組成物の製造方法 |
| JPH01113456A (ja) * | 1987-10-27 | 1989-05-02 | Nippon Petrochem Co Ltd | 熱可塑性樹脂組成物およびその製造方法 |
| US5218037A (en) * | 1987-08-17 | 1993-06-08 | Nippon Petrochemicals Co., Ltd. | Thermoplastic resin composition and method for preparing the same |
| JPH01113449A (ja) * | 1987-10-27 | 1989-05-02 | Nippon Petrochem Co Ltd | 熱可塑性樹脂組成物およびその製造方法 |
| EP0307802B1 (en) * | 1987-09-09 | 1995-01-11 | Nippon Petrochemicals Company, Limited | Thermoplastic resin composition and method for preparing the same |
| JPH01252660A (ja) * | 1988-04-01 | 1989-10-09 | Nippon Petrochem Co Ltd | 熱可塑性樹脂組成物およびその製造方法 |
| JPH01256564A (ja) * | 1988-04-06 | 1989-10-13 | Nippon Petrochem Co Ltd | 熱可塑性樹脂組成物およびその製造方法 |
| JPH0374461A (ja) * | 1989-08-11 | 1991-03-29 | Nippon Petrochem Co Ltd | 熱可塑性樹脂組成物およびその製造方法 |
-
1994
- 1994-01-25 US US08/187,158 patent/US5438108A/en not_active Expired - Lifetime
- 1994-01-25 KR KR1019940001312A patent/KR0175344B1/ko not_active Expired - Fee Related
- 1994-01-25 TW TW083100616A patent/TW260690B/zh active
- 1994-01-26 DE DE69404046T patent/DE69404046T2/de not_active Expired - Fee Related
- 1994-01-26 EP EP94101122A patent/EP0608856B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR940018415A (ko) | 1994-08-18 |
| TW260690B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-10-21 |
| KR0175344B1 (ko) | 1999-04-01 |
| EP0608856B1 (en) | 1997-07-09 |
| EP0608856A3 (en) | 1995-02-15 |
| US5438108A (en) | 1995-08-01 |
| EP0608856A2 (en) | 1994-08-03 |
| DE69404046D1 (de) | 1997-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |