EP4251675A1 - Polycarbonat sowie zusammensetzungen und artikel mit dem polycarbonat - Google Patents
Polycarbonat sowie zusammensetzungen und artikel mit dem polycarbonatInfo
- Publication number
- EP4251675A1 EP4251675A1 EP21836624.3A EP21836624A EP4251675A1 EP 4251675 A1 EP4251675 A1 EP 4251675A1 EP 21836624 A EP21836624 A EP 21836624A EP 4251675 A1 EP4251675 A1 EP 4251675A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- poly
- formula
- oxyalkylcarbonate
- substituted
- bis
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000004417 polycarbonate Substances 0.000 title description 50
- 229920000515 polycarbonate Polymers 0.000 title description 50
- 125000005647 linker group Chemical group 0.000 claims abstract description 40
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- -1 poly(alkoxyaryl) Polymers 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 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 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000005587 carbonate group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004122 cyclic group Chemical class 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001118 alkylidene group Chemical group 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229920001519 homopolymer Polymers 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- 229920000412 polyarylene Polymers 0.000 description 4
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- DTFQULSULHRJOA-UHFFFAOYSA-N 2,3,5,6-tetrabromobenzene-1,4-diol Chemical compound OC1=C(Br)C(Br)=C(O)C(Br)=C1Br DTFQULSULHRJOA-UHFFFAOYSA-N 0.000 description 2
- VJIDDJAKLVOBSE-UHFFFAOYSA-N 2-ethylbenzene-1,4-diol Chemical compound CCC1=CC(O)=CC=C1O VJIDDJAKLVOBSE-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 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
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- KMOHYLHXSATLNP-UHFFFAOYSA-N carbonochloridic acid;toluene Chemical compound OC(Cl)=O.CC1=CC=CC=C1 KMOHYLHXSATLNP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- FRNQLQRBNSSJBK-UHFFFAOYSA-N divarinol Chemical compound CCCC1=CC(O)=CC(O)=C1 FRNQLQRBNSSJBK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920012287 polyphenylene sulfone Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical class ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- DIQLMURKXNKOCO-UHFFFAOYSA-N 1,1,1',1'-tetramethyl-3,3'-spirobi[3a,7a-dihydro-2H-indene]-5,5'-diol Chemical compound CC1(C)CC2(CC(C)(C)C3C=CC(O)=CC23)C2C=C(O)C=CC12 DIQLMURKXNKOCO-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- UNIVUTHKVHUXCT-UHFFFAOYSA-N 2,2-bis(4-hydroxyphenyl)acetonitrile Chemical compound C1=CC(O)=CC=C1C(C#N)C1=CC=C(O)C=C1 UNIVUTHKVHUXCT-UHFFFAOYSA-N 0.000 description 1
- ZSDAMBJDFDRLSS-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diol Chemical compound OC1=C(F)C(F)=C(O)C(F)=C1F ZSDAMBJDFDRLSS-UHFFFAOYSA-N 0.000 description 1
- GFZYRCFPKBWWEK-UHFFFAOYSA-N 2,3,5,6-tetratert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=C(C(C)(C)C)C(O)=C1C(C)(C)C GFZYRCFPKBWWEK-UHFFFAOYSA-N 0.000 description 1
- JGJKHOVONFSHBV-UHFFFAOYSA-N 2,4,5,6-tetrabromobenzene-1,3-diol Chemical compound OC1=C(Br)C(O)=C(Br)C(Br)=C1Br JGJKHOVONFSHBV-UHFFFAOYSA-N 0.000 description 1
- NLQBQVXMWOFCAU-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-diol Chemical compound OC1=C(F)C(O)=C(F)C(F)=C1F NLQBQVXMWOFCAU-UHFFFAOYSA-N 0.000 description 1
- MYMNFZDGHOLHOF-UHFFFAOYSA-N 2-(2-carboxy-4-methylphenoxy)carbonyloxy-5-methylbenzoic acid Chemical compound C(OC1=C(C=C(C=C1)C)C(=O)O)(OC1=C(C=C(C=C1)C)C(=O)O)=O MYMNFZDGHOLHOF-UHFFFAOYSA-N 0.000 description 1
- LUELYTMQTXRXOI-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)benzene-1,4-diol Chemical compound C=1C(O)=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 LUELYTMQTXRXOI-UHFFFAOYSA-N 0.000 description 1
- VXLIZRNHJIWWGV-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)cyclopentyl]phenol Chemical compound OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)CCCC1 VXLIZRNHJIWWGV-UHFFFAOYSA-N 0.000 description 1
- NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 1
- XCUMMFDPFFDQEX-UHFFFAOYSA-N 2-butan-2-yl-4-[2-(3-butan-2-yl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)CC)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)CC)=C1 XCUMMFDPFFDQEX-UHFFFAOYSA-N 0.000 description 1
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
- WKVWOPDUENJKAR-UHFFFAOYSA-N 2-cyclohexyl-4-[2-(3-cyclohexyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(C2CCCCC2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1CCCCC1 WKVWOPDUENJKAR-UHFFFAOYSA-N 0.000 description 1
- XQOAPEATHLRJMI-UHFFFAOYSA-N 2-ethyl-4-[2-(3-ethyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(CC)=CC(C(C)(C)C=2C=C(CC)C(O)=CC=2)=C1 XQOAPEATHLRJMI-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical class CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- NJRNUAVVFBHIPT-UHFFFAOYSA-N 2-propylbenzene-1,4-diol Chemical compound CCCC1=CC(O)=CC=C1O NJRNUAVVFBHIPT-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- NZBJFCOVJHEOMP-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)butan-2-one Chemical compound C=1C=C(O)C=CC=1C(C)(C(=O)C)C1=CC=C(O)C=C1 NZBJFCOVJHEOMP-UHFFFAOYSA-N 0.000 description 1
- UAVUNEWOYVVSEF-UHFFFAOYSA-N 3,5-dihydroxybiphenyl Chemical compound OC1=CC(O)=CC(C=2C=CC=CC=2)=C1 UAVUNEWOYVVSEF-UHFFFAOYSA-N 0.000 description 1
- ZFXDUWYVZMVVQT-UHFFFAOYSA-N 3-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC(O)=CC=1C(C)(C)C1=CC=C(O)C=C1 ZFXDUWYVZMVVQT-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- VGPPHDKAFHZVCF-UHFFFAOYSA-N 4,4-bis(4-hydroxyphenyl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C(=O)NC2=O)C2=CC=C1 VGPPHDKAFHZVCF-UHFFFAOYSA-N 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- QVWDCTQRORVHHT-UHFFFAOYSA-N tropone Chemical compound O=C1C=CC=CC=C1 QVWDCTQRORVHHT-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/263—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing heterocyclic amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
Definitions
- Polycarbonates, copolymers thereof, and blends formed therefrom are useful in the manufacture of articles and components for a wide range of applications, from automotive parts to electronic appliances. Because of their broad use, particularly in automotive, lighting and consumer electronics industries, it is desirable to provide polycarbonates having a specific combination of properties. It would be particularly advantageous to provide a polycarbonate having good mechanical strength, low moisture uptake, and low birefringence. It would be a further advantage to provide a polycarbonate having improved flow, which can facilitate the manufacture of thin molded parts such as lenses.
- a poly(oxyalkylcarbonate) comprises oxyalkylaryl repeating units derived from a bis(substituted or unsubstituted 4-hydroxyalkoxyaryl)- or bis(substituted or unsubstituted 4- hydroxy(poly(alkoxyaryl))-substituted ring system, wherein the ring system is a substituted or unsubstituted 2-hydrocarbyl-isoindolin-l-one, a substituted cyclohexylidene, or an unsubstituted cyclohexylidene when the 4-hydroxyalkoxyaryl or the 4-hydroxy(poly(alkoxyaryl) groups are substituted.
- a method of making the poly (oxy alky lcarbonate) comprises contacting an aromatic dihydroxy compound corresponding to the repeating units of formula (I), (II), or a combination thereof and, optionally, an aromatic dihydroxy compound not including an oxyalkylene linking group, with a carbonate precursor under conditions effective to provide the poly (oxy alky lcarbonate) .
- a composition comprises the poly (oxy alky lcarbonate).
- An article comprises the poly(oxyalkylcarbonate) or the composition.
- a polycarbonate having a particularly desirable combination of properties can be prepared from specific monomers that provide an oxyalkylene linking group in the repeating unit structure (hereinafter referred to as a “poly (oxy alky lcarbonate)”).
- the poly(oxyalkylcarbonate) can exhibit one or more of reduced glass transition temperature, reduced refractive index, reduced stress optic coefficient, reduced entanglement molecular weight, reduced modulus, and increased brittle fracture stress, each as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present (i.e., a polycarbonate having repeating units that are identical except that the oxyalkylene linking group is omitted).
- an aspect is a poly(oxyalkylcarbonate) having an oxyalkylene linking group.
- “Polycarbonate” and “poly(oxyalkylcarbonate)” as used herein means a homopolymer or copolymer.
- a poly(oxyalkylcarbonate) comprises oxyalkylaryl repeating units derived from a bis(substituted or unsubstituted 4-hydroxyalkoxyaryl)- or bis(substituted or unsubstituted 4-hydroxy(poly(alkoxyaryl))-substituted ring system.
- substituted or unsubstituted 4-hydroxyalkoxyaryl refers to the alkoxy and/or the aryl groups in the repeating unit being substituted or unsubstituted. Possible substituents are described below.
- preferred substituents include halogen or hydrocarbyl, more preferably halogen, Ci- 6 alkyl, or Ci- 6 alkyloxy.
- the ring system is a substituted or unsubstituted 2- hydrocarbyl-isoindolin-l-one, a substituted cyclohexylidene, or an unsubstituted cyclohexylidene when a 4-hydroxyalkoxyaryl or 4-hydroxy(poly(alkoxyaryl) group is substituted.
- Possible substituents are described below.
- Preferred substituents include halogen or hydrocarbyl, more preferably halogen, Ci- 6 alkyl, or Ci- 6 alkyloxy.
- the oxyalkylaryl units are derived from a 3,3-(bis(substituted or unsubstituted 4-hydroxyalkoxyaryl))-2-hydrocarbyl-isoindolin-l-one that is further substituted or unsubstituted; a 3,3-(bis(substituted or unsubstituted 4-hydroxy(polyalkoxy))aryl)-2- hydrocarbyl-isoindolin-l-one; a l,l-(bis(substituted or unsubstituted 4-hydroxy(alkoxy))aryl)- hydrocarbyl substituted cyclohexylidene that is further substituted or unsubstituted; a 1,1- (substituted or unsubstituted bis(4-hydroxy(polyalkoxy))aryl)-hydrocarbyl-substituted cyclohexylidene; a 1,1 -(substituted or unsub
- the poly (oxy alky lcarbonate) comprises repeating units of the formula (I), (II), or a combination thereof.
- R a and R b are independently at each occurrence a halogen, C1-3 alkoxy, or Ci-3 alkyl;
- R 1 is independently at each occurrence a halogen, C M alkoxy, or C1-4 alkyl;
- R 2 is independently at each occurrence a C1-4 alkyl;
- R 3 is a Ci-12 alkyl, or phenyl optionally substituted with 1 to 5 Ci-6 alkyl;
- L is a C2-12 linear or branched alkylene or alkylidene;
- n is independently at each occurrence 1 to 10, or 1 to 8, or 1 to 6, or 1 to 4, or 1 to 2 or 1;
- j is 0 or 1 to 4; and
- p and q are independently at each occurrence 0 or 1 to 4, preferably 0 or 1; and
- m is 0 to
- p and q are each 0, or p and q is each 1 and R a and R b are each a methyl group disposed meta to the bond with oxygen on each arylene group.
- R 1 is independently at each occurrence a C1-3 alkyl, or C1-3 alkoxy.
- m is 1 to 5, preferably 1 to 3, preferably 3.
- R 2 is independently at each occurrence methyl.
- R 3 is Ci-12 alkyl, or phenyl optionally substituted with 1 to 5 Ci-6 alkyl, preferably Ci-6 alkyl, or phenyl optionally substituted with 1 to 5 Ci-6 alkyl, more preferably methyl or phenyl.
- L is a C2-6 linear alkylene, for example ethylene, propylene, butylene, preferably ethylene.
- L is a C3-12 branched alkylene or alkylidene.
- L is ethylene (i.e., a C2 alkylene).
- n is 1 to 4, or 1 to 2, or 1.
- p and q are each 0, or p and q is each 1 and R a and R b are each a methyl disposed meta to the bond with oxygen on each arylene ring; j is zero or 1, and R 1 is C1-3 alkyl; m is 1 to 3, preferably 3; R 2 is methyl; R 3 is Ci- 6 alkyl, or phenyl optionally substituted with 1 to 5 Ci- 6 alkyls, more preferably methyl or phenyl; L is a C2-6 linear alkylene or a C3-12 branched alkylene or alkylidene, preferably ethylene; and n is 1 to 4, or 1 to 2, or 1.
- p and q are each 0 or p and q is each 1 and R a and R b are each a methyl disposed meta to the bond to oxygen on each arylene ring; L is a C2-6 linear alkylene or a C3-8 branched alkylidene, preferably ethylene; and n is 1 or 2, preferably 1.
- p and q are each 0; m is 1 to 10, preferably 1 to 3; R 2 is a C1-3 alkyl, preferably methyl; L is a C2-6 linear alkylene or a C3-8 branched alkylidene, preferably ethylene; and n is 1 or 2, preferably 1.
- m 3
- R 2 is methyl
- the R 2 groups are at the 3,3,5 positions on the cyclohexane ring
- L is ethylene
- n is 1
- the poly(oxyalkylcarbonate) comprises, consists essentially of, or consists of repeating units according to formula (la)
- R a and R b are each Ci- 3 alkyl, preferably methyl meta to the oxygen bond of the aryl ring; m is 0 to 3; R 2 is C1-3 alkyl, preferably methyl; L is an ethylene group and n is 1.
- R a and R b are each methyl meta to the oxygen bond of the aryl ring, m is 0, L is an ethylene group and n is 1, the poly(oxyalkylcarbonate) comprises, consists essentially of, or consists of repeating units according to formula (lb) [0019]
- p and q are each 0, or p and q is each 1 and R a and R b are each methyl disposed meta to the bond to oxygen on each arylene ring; m is 1 to 3,
- R 1 is Ci-3 alkyl, preferably methyl; R 3 is independently at each occurrence Ci- 6 alkyl or phenyl, preferably methyl or phenyl.
- L is a C2-6 linear alkylene or a C3-8 branched alkylidene, preferably ethylene; and n is 1 or 2, preferably 1.
- the poly(oxyalkylcarbonate) can comprise, consist essentially of, or consist of repeating units according to formula (Ila)
- the poly(oxyalkylcarbonate) can be a homopoly(oxyalkylcarbonate) of repeating units of formula (I) or formula (II), preferably of repeating units of formula (la), formula (lb), or formula (Ila).
- the poly(oxyalkylcarbonate) can be a copolymer comprising repeating units different from the repeating units of formula (I) or formula (II).
- the poly(oxyalkylcarbonate) is a copolymer comprising repeating units different from the repeating units of formula (la), formula (lb), or formula (Ila).
- the poly(oxyalkylcarbonate) can further comprise oxyalkylaryl repeating units of formula (III) wherein R a , R b , p, q and n are as defined above in formula (I) or formula (II.
- p and q are each 0, or p and q is each 1 and R a and R b are each a methyl) disposed meta to the bond with oxygen on each arylene ring;
- L is a C 2-6 linear alkylene or a C 3-12 branched alkylene or alkylidene, preferably ethylene; and
- n is 1 to 4, or 1 to 2, or 1.
- p and q are each 0, or p and q is each 1 and R a and R b are each a methyl disposed meta to the bond to oxygen on each arylene ring; L is a C2-6 linear alkylene or a C3-8 branched alkylidene, preferably ethylene; and n is 1 or 2, preferably 1.
- L is ethylene and n is 1, the copolycarbonate can further comprise repeating units according to formula (Ilia) (Ilia).
- the relative amounts of different oxyalkylcarbonate units in the copolycarbonates can be varied depending on the desired characteristics of the polymer.
- the poly(oxyalkylcarbonate) can include repeating units of formula (I), (II), or a combination thereof, preferably repeating units of formula (la), (lb), (Ila), or a combination thereof, in an amount of 1 to 99 mole percent, or 5 to 99 mole percent, or 10 to 99 mole percent, or 20 to 99 mole percent, or 30 to 99 mole percent, or 40 to 99 mole percent, or 50 to 99 mole percent.
- the poly(oxyalkylcarbonate) can include repeating units of formula (I), (II), or a combination thereof, preferably repeating units of formula (la), (lb), (Ila), or a combination thereof, in an amount of 1 to 95 mole percent, or 1 to 90 mole percent, or 1 to 80 mole percent, or 1 to 70 mole percent, or 1 to 60 mole percent, or 1 to 50 mole percent, with the remaining units being of formula (III), preferably of formula (Ilia), each based on the total moles of repeating units of the poly (oxyalkylcarbonate), which totals 100 mole percent.
- the poly (oxyalkylcarbonate) can comprise repeating units of formula (I), (II), or a combination thereof, preferably repeating units of formula (la), (lb), (Ila), or a combination thereof in an amount of 5 to 95 mole percent, or 10 to 90 mole percent, or 20 to 80 mole percent, or 30 to 70 mole percent, with the remaining units being of formula (III), preferably of formula (Ilia), each based on the total moles of repeating units of the poly (oxyalkylcarbonate), which totals 100 mole percent.
- the copolycarbonate can further comprise carbonate repeating units wherein no oxyalkylene linking group is present.
- These can be repeating structural carbonate units of formula (IV) wherein represents a point of attachment to the other units of the copolycarbonate or an end group, and R 4 does not contain an oxyalkylene linker group.
- R 4 does not contain an oxyalkylene linker group.
- at least 60 percent of the total number of R 4 groups are aromatic, or each R 4 group contains at least one C6-30 aromatic group.
- each R 4 can be derived from an aromatic dihydroxy compound not having an oxyalkylene linker group, such as an aromatic dihydroxy compound of formula (V) or a bisphenol of formula (5).
- each R h is independently a halogen atom, for example bromine, a CMO hydrocarbyl group such as a Ci-io alkyl, a halogen-substituted Ci-io alkyl, a C6-10 aryl, or a halogen-substituted C 6-i o aryl, and n is 0 to 4.
- a halogen atom for example bromine
- a CMO hydrocarbyl group such as a Ci-io alkyl, a halogen-substituted Ci-io alkyl, a C6-10 aryl, or a halogen-substituted C 6-i o aryl
- n is 0 to 4.
- R a and R b are each independently a halogen, Ci-12 alkoxy, or Ci- 12 alkyl, and p and q are each independently 0 or 1 to 4, such that when p or q is less than 4, the valence of each carbon of the ring is filled by hydrogen.
- p and q is each 0, or p and q is each 1
- R a and R b are each a C1-3 alkyl, preferably methyl, disposed meta to the hydroxy group on each arylene group.
- X a is a bridging group connecting the two hydroxy-substituted aromatic groups, where the bridging group and the hydroxy substituent of each Ce arylene group are disposed ortho, meta, or para (preferably para) to each other on the Ce arylene group, for example, a single bond, -0-, -S-, -S(O)-, -S(0) 2 -, -C(O)-, or a C MS organic group, which can be cyclic or acyclic, aromatic or non-aromatic, and can further comprise heteroatoms such as halogens, oxygen, nitrogen, sulfur, silicon, or phosphorous.
- bisphenol compounds include 4,4'-dihydroxybiphenyl, 1,6- dihydroxynaphthalene, 2,6-dihydroxynaphthalene, bis(4-hydroxyphenyl)methane, bis(4- hydroxyphenyl)diphenylmethane, bis(4-hydroxyphenyl)-l-naphthylmethane, l,2-bis(4- hydroxyphenyl)ethane, l,l-bis(4-hydroxyphenyl)-l-phenylethane, 2-(4-hydroxyphenyl)-2-(3- hydroxyphenyl)propane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3- bromophenyl)propane, 1,1 -bis (hydroxyphenyl)cyclopentane, l,l-bis(4- hydroxyphenyl)cyclohexane, 1 , 1 -bis(4-hydroxyphenyl)
- 1.6-bis(4-hydroxyphenyl)-l,6-hexanedione ethylene glycol bis(4-hydroxyphenyl)ether, bis(4- hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl) sulfoxide, bis(4- hydroxyphenyl)sulfone, 9,9-bis(4-hydroxyphenyl)fluorene, 2,7-dihydroxypyrene, 6,6'- dihydroxy-3,3,3',3'- tetramethylspiro(bis)indane ("spirobiindane bisphenol"), 3,3-bis(4- hydroxyphenyl)phthalimide, 2,6-dihydroxydibenzo-p-dioxin, 2,6-dihydroxythianthrene, 2,7- dihydroxyphenoxathin, 2,7-dihydroxy-9, 10-dimethylphenazine, 3,6-dihydroxydibenzofuran,
- resorcinol substituted resorcinol compounds such as 5-methyl resorcinol, 5-ethyl resorcinol, 5-propyl resorcinol, 5-butyl resorcinol, 5-t-butyl resorcinol, 5-phenyl resorcinol, 5-cumyl resorcinol, 2,4,5,6-tetrafluoro resorcinol, 2,4,5,6-tetrabromo resorcinol, or the like; catechol; hydroquinone; substituted hydroquinones such as 2-methyl hydroquinone, 2-ethyl hydroquinone, 2-propyl hydroquinone, 2-butyl hydroquinone, 2-t-butyl hydroquinone, 2-phenyl hydroquinone, 2-cumyl hydroquinone,
- the polycarbonate is a copolycarbonate further comprising repeating units derived from 2,2-bis(4-hydroxyphenyl) propane (bisphenol A), l,l-bis(4-hydroxy-3- methylphenyl)cyclohexane, 2-phenyl-3,3’-bis(4-hydroxyphenyl) phthalimidine, 4,4'-(3,3,5- trimethylcyclohexane-l,l-diyl)diphenol (also known as isophorone bisphenol or bisphenol TMC), or a combination thereof.
- bisphenol A 2,2-bis(4-hydroxyphenyl) propane
- l,l-bis(4-hydroxy-3- methylphenyl)cyclohexane 2,2-bis(4-hydroxy-3- methylphenyl)cyclohexane
- 2-phenyl-3,3’-bis(4-hydroxyphenyl) phthalimidine 4,4'-(3,3,5- trimethylcyclohexane-l,l-diyl)d
- copolycarbonates contain oxyalkylcarbonate units of formula (I), (II), or a combination thereof, and optionally units of formula (III), together with carbonate units of formula (IV), the relative amounts of each type of unit is adjusted to obtain the desired properties.
- the amount of units of formula (I), (II), or a combination thereof, preferably of formulas (la), (lb), (Ila), or a combination thereof can vary widely, from 1 to 100 mole percent, with the optional units of formula (III), preferably formula (Ilia), providing the remainder of the oxyalkylcarbonate units, i.e., 0 to 99 mole percent, each based on the total moles of oxyalkylcarbonate units, which totals 100 mole percent.
- the amount of units of formula (I), (II), or a combination thereof, preferably of formulas (la), (lb), (Ila), or a combination thereof, can be from 1 to 99 mole percent, 10 to 99 mole percent, 20 to 99 mole percent, 30 to 99 mole percent, 40 to 95 mole percent, 50 to 95 mole percent, 1 to 95 mole percent, 1 to 90 mole percent, 1 to 80 mole percent, 1 to 70 mole percent, 1 to 60 mole percent, 1 to 50 mole percent, 5 to 95 mole percent, 10 to 90 mole percent, 20 to 80 mole percent, or 30 to 70 mole percent, with the units of formula (III), preferably formula (Ilia), providing the remainder of the oxyalkylcarbonate units, each based on the total moles of oxyalkylcarbonate units, which totals 100 mole percent.
- the copolycarbonates contain oxyalkylcarbonate units of formula (I), (II), or a combination thereof, and optionally units of formula (III), together with carbonate units of formula (IV), the total amount of oxyalkylcarbonate units (the total of the amount of units of formula (I), (II), or a combination thereof and optionally formula (III), preferably the total amount of formulas (la), (lb), (Ila), or a combination thereof and optionally formula (Ilia), can vary widely, from 1 to 99 mole percent, with the carbonate units of formula (IV) providing the remainder of the carbonate units, i.e., 1 to 99 mole percent, each based on the total of the total of the oxyalkylcarbonate units and non-oxyalkylcarbonate carbonate units in the copolymer, which totals 100 mole percent.
- the total amount of oxyalkylcarbonate units can be can be from 1 to 99 mole percent, 10 to 99 mole percent, 20 to 99 mole percent, 30 to 99 mole percent, 40 to 95 mole percent, 50 to 95 mole percent, 1 to 95 mole percent, 1 to 90 mole percent, 1 to 80 mole percent, 1 to 70 mole percent, 1 to 60 mole percent, 1 to 50 mole percent, 5 to 95 mole percent, 10 to 90 mole percent, 20 to 80 mole percent, or 30 to 70 mole percent, with the units of formula (IV), preferably bisphenol A, l,l-bis(4-hydroxy-3- methylphenyl)cyclohexane, 2-phenyl-3,3’-bis(4-hydroxyphenyl) phthalimidine4,4'-(3,3,5- trimethylcyclohexane-l,l-diyl)diphenol, or a combination thereof providing the remainder of the carbonate units, each based on the total moles of oxyalkylcarbonate
- the poly(oxyalkylcarbonate) can provide one or more advantageous properties.
- the poly (oxyalkylcarbonate) can have a reduced glass transition temperature as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present. Glass transition temperature can be determined, for example, by differential scanning calorimetry.
- the poly(oxyalkylcarbonate) can have a reduced refractive index as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the poly(oxyalkylcarbonate) can have a reduced stress optic coefficient as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the poly(oxyalkylcarbonate) can have a reduced entanglement molecular weight as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the poly(oxyalkylcarbonate) can have a reduced modulus as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the poly (oxy alky lcarbonate) can have an increased brittle fracture stress as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the poly(oxyalkylcarbonate) can exhibit one, two, three, four, five, or all of the foregoing properties. Where the poly(oxyalkylcarbonate) is described as having a “reduced” property relative to the reference polycarbonate (i.e., the polycarbonate of the same composition except that the oxyalkylene linking group is not present), it will be understood that the recited property can be reduced by at least 5%, or at least 10%, or at least 20%, or at least 30%, or at least 40%, or at least 50%, relative to the reference polycarbonate.
- poly(oxyalkylcarbonate) is described as having an “increased” property relative to the reference polycarbonate (i.e., the polycarbonate of the same composition except that the oxyalkylene linking group is not present), it will be understood that the recited property can be increased by at least 5%, or at least 10%, or at least 20%, or at least 30%, or at least 40%, or at least 50%, relative to the reference polycarbonate.
- the glass transition temperature that is reduced by at least 10%, or at least 15% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present
- refractive index can be reduced by at least 0.75%, or at least 1% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- stress optic coefficient can be reduced by at least 20%, or at least 25% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- entanglement molecular weight can be reduced by at least 5%, or at least 10% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- modulus can be reduced by at least 5%, or at least 10%, or at least 15% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- brittle fracture stress can be increased by at least 10%, or at least 15% as compared to a polycarbonate of the same composition except that the oxyalkylene linking group is not present.
- the polycarbonate when the poly(oxyalkylcarbonate) comprises repeating units according to formula (I), particularly when in formula (I) p and q are each 0, m is 3, R 2 is methyl, wherein R 2 groups are at the 3,3,5 positions on the cyclohexane ring, the polycarbonate can have one or more of a glass transition temperature of less than 215°C, or 150 to 200°C, or 165 to 200°C, a refractive index of less than or equal to 1.55, or 1.53 to 1.55, a stress optic coefficient of less than 25, or 0.1 to 20, or 0.1 to 5, an entanglement molecular weight of less than 2800 g/mol, or 2000 to 2750 g/mol, a modulus of less than or equal to 2.5 GPa, or 1.9 to 2.4 GPa and a brittle fracture stress of greater than or equal to 75 MPa, or 75 to 130 MPa, or 90 to 130 MPa.
- a glass transition temperature of less than 215°C, or 150 to
- the polycarbonate when the poly (oxy alky lcarbonate) comprises repeating units according to formula (II), the polycarbonate can have one or more of a glass transition temperature of less than 260°C, or 180 to 255°C, a refractive index of less than or equal to 1.62, or 1.55 to 1.62, a stress optic coefficient of less than 50, or 1 to 48, an entanglement molecular weight of less than 3000 g/mol, or 2000 to 2900 g/mol, a modulus of less than or equal to 2.8 GPa, or 1.9 to 2.8 GPa and a brittle fracture stress of greater than or equal to 80 MPa, or 80 to 100 MPa.
- the poly(oxyalkylcarbonate) can be made from an aromatic dihydroxy compound containing an oxyalkylene linking group corresponding to the repeating units of formula (I) or (II), for example, aromatic dihydroxy compounds according to formula (Ic) or (lie). wherein the variables are as defined in formulas (I) and (II).
- One or more aromatic dihydroxy compound containing an oxyalkylene linking group optionally together with a dihydroxy compound of formula (V), (VI), or a combination can be contacted with a carbonate precursor under conditions effective to provide the polycarbonate.
- the polycarbonates can be manufactured by methods such as interfacial polymerization and melt polymerization, which are known, and are described, for example, in WO 2013/175448 A1 and WO 2014/072923 Al.
- An end-capping agent (also referred to as a chain stopper agent or chain terminating agent) can be included during polymerization to provide end groups, for example monocyclic phenols such as phenol, p-cyanophenol, and Ci-22 alkyl-substituted phenols such as p-cumyl-phenol, resorcinol monobenzoate, and p-and tertiary- butyl phenol, monoethers of diphenols, such as p-methoxyphenol, monoesters of diphenols such as resorcinol monobenzoate, functionalized chlorides of aliphatic monocarboxylic acids such as acryloyl chloride and methacryoyl chloride, and mono-chloroformates such as phenyl chloroformate, alkyl-substituted phenyl chloroformates, p-cumyl phenyl chloroformate, and toluene chloroformate. Combinations of different end
- Exemplary carbonate precursors for forming the polycarbonate can include a carbonyl halide such as carbonyl bromide or carbonyl chloride (phosgene) a bishaloformate of a dihydroxy compound (e.g., the bischloroformate of bisphenol A, hydroquinone ethylene glycol, neopentyl glycol, or the like), and diaryl carbonates. A combination thereof can also be used.
- phosgene carbonyl bromide or carbonyl chloride
- phosgene phosgene
- bishaloformate of a dihydroxy compound e.g., the bischloroformate of bisphenol A, hydroquinone ethylene glycol, neopentyl glycol, or the like
- diaryl carbonates e.g., the bischloroformate of bisphenol A, hydroquinone ethylene glycol, neopentyl glycol, or the like
- the diaryl carbonate ester can be diphenyl carbonate, or an activated diphenyl carbonate having electron-withdrawing substituents on the each aryl, such as bis(4-nitrophenyl)carbonate, bis(2- chlorophenyl)carbonate, bis(4-chlorophenyl)carbonate, bis(methyl salicyl)carbonate, bis(4- methylcarboxylphenyl) carbonate, bis(2-acetylphenyl) carboxylate, bis(4-acetylphenyl) carboxylate, or a combination thereof.
- an activated diphenyl carbonate having electron-withdrawing substituents on the each aryl such as bis(4-nitrophenyl)carbonate, bis(2- chlorophenyl)carbonate, bis(4-chlorophenyl)carbonate, bis(methyl salicyl)carbonate, bis(4- methylcarboxylphenyl) carbonate, bis(2-acetylphenyl) carboxylate,
- interfacial polymerization When interfacial polymerization is used, the polymerization can be conducted in the presence of an interfacial catalyst.
- an interfacial catalyst Among tertiary amines that can be used as catalysts in interfacial polymerization are aliphatic tertiary amines such as triethylamine and tributylamine, cycloaliphatic tertiary amines such as N,N-diethyl-cyclohexylamine, and aromatic tertiary amines such as N,N-dimethylaniline.
- phase transfer catalysts that can be used are catalysts of the formula (R 3 )4Q + X, wherein each R 3 is the same or different, and is a Ci-io alkyl; Q is a nitrogen or phosphorus atom; and X is a halogen atom or a Ci-s alkoxy or Ce-is aryloxy.
- Exemplary phase transfer catalysts include (CH3(CH2)3)4NX, (CH3(CH2)3)4PX,
- An effective amount of a phase transfer catalyst can be 0.1 to 10 wt%, or 0.5 to 2 wt%, each based on the weight of dihydroxy compound in the phosgenation mixture.
- melt processes can be used to make the polycarbonates.
- polycarbonates can generally be prepared by co-reacting, in a molten state, a dihydroxy reactant as described above and a diaryl carbonate ester as described above in the presence of a transesterification catalyst. Conditions for melt process are described, for example, in WO2013/027165 and the references cited therein.
- Catalysts used in the melt polymerization can include an alpha catalyst and a beta catalyst.
- Alpha catalysts can comprise a source of alkali or alkaline earth ions and are typically more thermally stable and less volatile than beta catalysts.
- Beta catalysts are typically volatile and degrade at elevated temperatures, and can comprise a transesterification catalyst of the formula (R 3 )4Q + X as described above.
- Beta catalysts are therefore preferred for use at early low-temperature polymerization stages.
- the alpha catalyst can be used in an amount sufficient to provide 1 x 10 2 to 1 x 10 8 moles, preferably, 1 x 10 4 to 1 x 10 7 moles of metal per mole of the dihydroxy compounds used.
- the amount of beta catalyst e.g., organic ammonium or phosphonium salts
- the amount of beta catalyst can be 1 x 10 2 to 1 x 10 5 , preferably 1 x 10 3 to 1 x 10 4 moles per total mole of the dihydroxy compounds in the reaction mixture. Quenching of the transesterification catalysts and any reactive catalysts residues with an acidic compound after polymerization is completed can also be useful in some melt polymerization processes.
- R 8 is hydrogen, Ci-12 alkyl
- An end-capping agent (also referred to as a chain stopper agent or chain terminating agent) can be included during polymerization to provide end groups.
- the end capping agent (and thus end groups) are selected based on the desired properties of the polycarbonates.
- Exemplary end-capping agents are exemplified by monocyclic phenols such as phenol and Ci-22 alkyl-substituted phenols such as p-cumyl-phenol, resorcinol monobenzoate, and p-and tertiary-butyl phenol, monoethers of diphenols, such as p-methoxyphenol, and alkyl- substituted phenols with branched chain alkyl substituents having 8 to 9 carbon atoms, 4- substituted-2-hydroxybenzophenones and their derivatives, aryl salicylates, monoesters of diphenols such as resorcinol monobenzoate, 2-(2-hydroxyaryl)-benzotriazoles and their derivatives, 2-(2-hydroxyaryl)-l,3,5-triazines and their derivatives, mono-carboxylic acid chlorides such as benzoyl chloride, Ci-22 alkyl-substituted benzoyl chloride, toluoyl chloride
- the poly(oxyalkylcarbonate) can be useful for forming a composition comprising the poly (oxy alky lcarbonate).
- the composition can comprise the poly(oxyalkylcarbonate) (i.e., including repeating units according to formulas (I), (II), or a combination thereof), and a polymer different from the poly (oxy alky lcarbonate) of the present disclosure.
- the poly(oxyalkylcarbonate) can be present in an amount of 1 to 99 weight percent, and the polymer different from the poly(oxyalkylcarbonate) can be present in an amount of 1 to 99 weight percent, each based on the total weight of the composition.
- the polymer different from the poly (oxy alky lcarbonate) can include, for example, polyacetals (e.g., polyoxyethylene and polyoxymethylene), poly(Ci- 6 alkyl)acrylates, polyacrylamides, polyamides, (e.g., aliphatic polyamides, polyphthalamides, and polyaramides), polyamideimides, polyanhydrides, polyarylates, polyarylene ethers (e.g., polyphenylene ethers), polyarylene sulfides (e.g., polyphenylene sulfides), polyarylene sulfones (e.g., polyphenylene sulfones), polybenzothiazoles, polybenzoxazoles, polycarbonates (including polycarbonate copolymers such as polycarbonate-siloxanes, polycarbonate-esters, and polycarbonate-ester- siloxanes, provided that any polycarbonate is different in composition from the poly(oxyalkylcarbonate).
- the polymer different from the poly(oxyalkylcarbonate) can comprise a polycarbonate (not including repeating units according to formulas (I) or (II)), a polyetherimide, a polyimide, a polysulfone, a polyethersulfone, a polyphenylene sulfone, a polyarylene ether, a polyetherether ketone, a polyamide, or a combination thereof.
- the poly(oxyalkylcarbonate) can be blended with a polycarbonate of repeating units derived from bisphenol A, l,l-bis(4-hydroxy-3-methylphenyl)cyclohexane, 2 -phenyl-3, 3 ’-bis(4- hydroxyphenyl) phthalimidine, or 4,4'-(3,3,5-trimethylcyclohexane-l,l-diyl)diphenol.
- the composition can optionally further comprise an additive composition comprising one or more additives.
- the one or more additives can be selected to achieve a desired property, with the proviso that the additive(s) are also selected so as to not significantly adversely affect a desired property of the composition.
- the additive composition or individual additives can be mixed at a suitable time during the mixing of the components for forming the composition.
- the additive can be soluble or non-soluble in polycarbonate.
- the additive composition can include an impact modifier, flow modifier, filler (e.g., a particulate polytetrafluoroethylene (PTFE), glass, carbon, mineral, or metal), reinforcing agent (e.g., glass fibers), antioxidant, heat stabilizer, light stabilizer, ultraviolet (UV) light stabilizer, UV absorbing additive, plasticizer, lubricant, release agent (such as a mold release agent), antistatic agent, anti-fog agent, antimicrobial agent, colorant (e.g, a dye or pigment), surface effect additive, radiation stabilizer, flame retardant, anti-drip agent (e.g., a PTFE-encapsulated styrene- acrylonitrile copolymer (TSAN)), or a combination thereof.
- filler e.g., a particulate polytetrafluoroethylene (PTFE), glass, carbon, mineral, or metal
- reinforcing agent e.g., glass fibers
- antioxidant heat stabilizer, light stabilizer, ultraviolet
- the additives are used in the amounts generally known to be effective.
- the total amount of the additive composition (other than any impact modifier, filler, or reinforcing agent) can be 0.001 to 10.0 wt%, or 0.01 to 5 wt%, each based on the total weight of the polymer in the composition.
- the composition can be manufactured by various methods known in the art. For example, powdered polycarbonate, and other optional components are first blended, optionally with any fillers, in a high speed mixer or by hand mixing. The blend is then fed into the throat of a twin-screw extruder via a hopper. Alternatively, at least one of the components can be incorporated into the composition by feeding it directly into the extruder at the throat or downstream through a sidestuffer, or by being compounded into a masterbatch with a desired polymer and fed into the extruder. The extruder is generally operated at a temperature higher than that necessary to cause the composition to flow. The extrudate can be immediately quenched in a water bath and pelletized. The pellets so prepared can be one-fourth inch long or less as desired. Such pellets can be used for subsequent molding, shaping, or forming.
- Shaped, formed, or molded articles comprising the poly(oxyalkylcarbonate) or the polycarbonate composition are also provided.
- the poly(oxyalkylcarbonate) or the polycarbonate composition can be molded into useful shaped articles by a variety of methods, such as injection molding, extrusion, rotational molding, blow molding and thermoforming.
- Some examples of articles include computer and business machine housings such as housings for monitors, handheld electronic device housings such as housings for cell phones, electrical connectors, and components of lighting fixtures, ornaments, home appliances, roofs, greenhouses, sun rooms, swimming pool enclosures, and the like.
- Additional exemplary articles include a plug, a plug housing, a switch, an electrical conductor, a connector, an electric board, a lamp holder, a lamp cover, a lamp bezel, a reflector, a signal indicator, glazing, a lens, a lens holder, a waveguide element, a collimator, a light emitting diode, a diffuser sheet, a safety pane, a film, a film laminate, a safety goggle, and a visor.
- the poly(oxyalkylcarbonate) and composition can be especially useful for articles such as a lens, an automotive part, an optical article, a dielectric film, a viewing screen, or a display.
- the ethoxylated monomers of Table 1 can be prepared using techniques that are generally known.
- BPA can be converted to BPA-Et through reaction with ethylene carbonate in the presence of triethylamine at 105°C for 24 hours to provide BPA-Et in a yield of 40-45%, or in the presence of potassium iodide at 150°C for 4 hours to provide BPA- Et in a yield of greater than 90%.
- BPA can be converted to BPA-Et through reaction with ethylene glycol in the presence of sodium carbonate, urea, and zinc oxide at a temperature of 175°C for 2 hours, to provide BPA-Et in a yield of 85-90%.
- BPA can be converted to BPA-Et through reaction with ethylene oxide in the presence of triethylamine and acetone at a temperature of 130°C for less than 1 hour to provide BPA-Et in a yield of greater than 95%.
- DMBPC-Et, PPPBP-Et and BPI-Et can be prepared using similar methods.
- a 50:50 copolymer of DMBPC-BPA (E10) is generally brittle, with a brittle fracture stress of 88 MPa.
- the ethoxylated version (Ell) provided a 50:50 copolymer with a brittle fracture stress of 110 MPa, which is similar to the BPA homopolymer, having a brittle fracture stress of 109 MPa.
- a “soft” alkyl group e.g., an ethoxy group
- incorporation of a “soft” alkyl group can lead to an improved property profile for various polycarbonate structures, including both homopolymers and copolymers.
- a “soft” alkyl group e.g., an ethoxy group
- addition of the ethoxy group can decrease chain stiffness, thereby impacting properties including mechanical strength, moisture uptake and birefringence.
- the polymer flow increases significantly, allowing for molding of very thin parts such as lenses. So, a significant improvement is provided by the present disclosure.
- compositions, methods, and articles can alternatively comprise, consist of, or consist essentially of, any appropriate materials, steps, or components herein disclosed.
- the compositions, methods, and articles can additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any materials (or species), steps, or components, that are otherwise not necessary to the achievement of the function or objectives of the compositions, methods, and articles.
- an aspect means that a particular element described in connection with the aspect is included in at least one aspect described herein, and may or may not be present in other aspects.
- the term “combination thereof’ as used herein includes one or more of the listed elements, and is open, allowing the presence of one or more like elements not named.
- the described elements may be combined in any suitable manner in the various aspects.
- test standards are the most recent standard in effect as of the filing date of this application, or, if priority is claimed, the filing date of the earliest priority application in which the test standard appears.
- hydrocarbyl refers to a residue that contains only carbon and hydrogen.
- the residue can be aliphatic or aromatic, straight-chain, cyclic, bicyclic, branched, saturated, or unsaturated. It can also contain combinations of aliphatic, aromatic, straight chain, cyclic, bicyclic, branched, saturated, and unsaturated hydrocarbon moieties.
- the hydrocarbyl residue when described as substituted, it may, optionally, contain heteroatoms over and above the carbon and hydrogen members of the substituent residue.
- the hydrocarbyl residue can also contain one or more carbonyl groups, amino groups, hydroxyl groups, or the like, or it can contain heteroatoms within the backbone of the hydrocarbyl residue.
- alkyl means a branched or straight chain, saturated aliphatic hydrocarbon group, e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n- pentyl, s-pentyl, and n- and s-hexyl.
- Alkoxy means an alkyl group that is linked via an oxygen (i.e., alkyl-O-), for example methoxy, ethoxy, and sec-butyloxy groups.
- Alkylene means a straight or branched chain, saturated, divalent aliphatic hydrocarbon group (e.g., methylene (-CH 2 -) or, propylene (-(CH 2 ) 3 - )).
- Cycloalky lene means a divalent cyclic alkylene group, -C n Fh n-x , wherein x is the number of hydrogens replaced by cyclization(s).
- Cycloalkenyl means a monovalent group having one or more rings and one or more carbon-carbon double bonds in the ring, wherein ah ring members are carbon (e.g., cyclopentyl and cyclohexyl).
- Aryl means an aromatic hydrocarbon group containing the specified number of carbon atoms, such as phenyl, tropone, indanyl, or naphthyl.
- Arylene means a divalent aryl group.
- Alkylarylene means an arylene group substituted with an alkyl group.
- Arylalkylene means an alkylene group substituted with an aryl group (e.g., benzyl).
- halo means a group or compound including one more of a fluoro, chloro, bromo, or iodo substituent. A combination of different halo atoms (e.g., bromo and fluoro), or only chloro atoms can be present.
- hetero means that the compound or group includes at least one ring member that is a heteroatom (e.g., 1, 2, or 3 heteroatom(s)), wherein the heteroatom(s) is each independently N, O, S, Si, or P.
- a heteroatom e.g., 1, 2, or 3 heteroatom(s)
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US20130317142A1 (en) | 2012-05-24 | 2013-11-28 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic compositions, methods of manufacture thereof and articles comprising the same |
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