CA1064191A - Polycarbonates thermoplastiques ramifies a poids moleculaire eleve - Google Patents

Polycarbonates thermoplastiques ramifies a poids moleculaire eleve

Info

Publication number: CA1064191A
Authority: CA; Canada
Prior art keywords: polycarbonate; mol; bis; branched; molecular weight
Prior art date: 1975-01-03
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

Application number

CA242,504A

Other languages

English (en)

Inventor

Karsten-Josef Idel

Dieter Freitag

Werner Nouvertne

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1975-01-03

Filing date

1975-12-22

Publication date

1979-10-09

1975-12-22 Application filed by Bayer AG filed Critical Bayer AG

1979-10-09 Application granted granted Critical

1979-10-09 Publication of CA1064191A publication Critical patent/CA1064191A/fr

Status Expired legal-status Critical Current

Links

239000004417 polycarbonate Substances 0.000 title claims abstract description 93
229920000515 polycarbonate Polymers 0.000 title claims abstract description 85
229920001169 thermoplastic Polymers 0.000 title claims abstract description 10
239000004416 thermosoftening plastic Substances 0.000 title claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 36
230000008569 process Effects 0.000 claims abstract description 35
239000006085 branching agent Substances 0.000 claims abstract description 28
238000002360 preparation method Methods 0.000 claims abstract description 11
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 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 24
-1 aromatic hydroxy compound Chemical class 0.000 claims description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
229930185605 Bisphenol Natural products 0.000 claims description 13
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 11
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 7
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 7
238000000149 argon plasma sintering Methods 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
239000000155 melt Substances 0.000 claims description 5
238000004132 cross linking Methods 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
125000005587 carbonate group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
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 claims 2
239000003063 flame retardant Substances 0.000 claims 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 2
125000001624 naphthyl group Chemical group 0.000 claims 1
239000011347 resin Substances 0.000 claims 1
229920005989 resin Polymers 0.000 claims 1
238000009757 thermoplastic moulding Methods 0.000 claims 1
238000001125 extrusion Methods 0.000 abstract description 21
238000012545 processing Methods 0.000 abstract description 16
238000001746 injection moulding Methods 0.000 abstract description 15
238000010348 incorporation Methods 0.000 abstract description 5
239000000243 solution Substances 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000009833 condensation Methods 0.000 description 17
230000005494 condensation Effects 0.000 description 15
SJDACOMXKWHBOW-UHFFFAOYSA-N oxyphenisatine Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2NC1=O SJDACOMXKWHBOW-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
JMRKBGGTRCRBEM-UHFFFAOYSA-N 1h-indole-2,3-dione;phenol Chemical class OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2C(=O)C(=O)NC2=C1 JMRKBGGTRCRBEM-UHFFFAOYSA-N 0.000 description 10
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 10
239000012071 phase Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
239000002253 acid Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
229940083608 sodium hydroxide Drugs 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003792 electrolyte Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005809 transesterification reaction Methods 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
OEPVVQUSBPPMKV-UHFFFAOYSA-N 3,3-bis(4-hydroxynaphthalen-1-yl)-1h-indol-2-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4NC3=O)C3=CC=C(C4=CC=CC=C43)O)=CC=C(O)C2=C1 OEPVVQUSBPPMKV-UHFFFAOYSA-N 0.000 description 2
ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000000071 blow moulding Methods 0.000 description 2
238000007664 blowing Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
OASFYFTVWALXTH-UHFFFAOYSA-L disodium;diphenoxide Chemical compound [Na+].[Na+].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OASFYFTVWALXTH-UHFFFAOYSA-L 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
230000008018 melting Effects 0.000 description 2
HMNKTRSOROOSPP-UHFFFAOYSA-N meta-ethylphenol Natural products CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
VLJSLTNSFSOYQR-UHFFFAOYSA-N meta-isopropyl phenol Natural products CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
GJHVEONIFIJEIH-UHFFFAOYSA-N (2-chloronaphthalen-1-yl) (2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=C(Cl)C=CC2=CC=CC=C12 GJHVEONIFIJEIH-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
IPIDPQZZFLZUCU-UHFFFAOYSA-N 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol 2-methylphenol Chemical compound CC1=CC=CC=C1O.CC1=CC=CC=C1O.CC1=CC=CC=C1O.CC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(C)C=3)O)C=C(C)C=2)O)=C1 IPIDPQZZFLZUCU-UHFFFAOYSA-N 0.000 description 1
SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 1
SBYWPTRVJQXVLJ-UHFFFAOYSA-N 2-chlorobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1Cl SBYWPTRVJQXVLJ-UHFFFAOYSA-N 0.000 description 1
MQSXUKPGWMJYBT-UHFFFAOYSA-N 3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1 MQSXUKPGWMJYBT-UHFFFAOYSA-N 0.000 description 1
MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 description 1
KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
UDKBLXVYLPCIAZ-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-3,6-di(propan-2-yl)phenyl]phenol Chemical compound C=1C=C(O)C=CC=1C=1C(C(C)C)=CC=C(C(C)C)C=1C1=CC=C(O)C=C1 UDKBLXVYLPCIAZ-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
QCTZEHIRXZGGSD-UHFFFAOYSA-N 5,7-dibromo-1h-indole-2,3-dione Chemical compound BrC1=CC(Br)=CC2=C1NC(=O)C2=O QCTZEHIRXZGGSD-UHFFFAOYSA-N 0.000 description 1
AYGGQJHJRFZDFH-UHFFFAOYSA-N 5,7-dichloro-1h-indole-2,3-dione Chemical compound ClC1=CC(Cl)=CC2=C1NC(=O)C2=O AYGGQJHJRFZDFH-UHFFFAOYSA-N 0.000 description 1
MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 1
XHDJYQWGFIBCEP-UHFFFAOYSA-N 5-Chloro-1H-indole-2,3-dione Chemical compound ClC1=CC=C2NC(=O)C(=O)C2=C1 XHDJYQWGFIBCEP-UHFFFAOYSA-N 0.000 description 1
OCVKSIWBTJCXPV-UHFFFAOYSA-N 7-bromo-1h-indole-2,3-dione Chemical compound BrC1=CC=CC2=C1NC(=O)C2=O OCVKSIWBTJCXPV-UHFFFAOYSA-N 0.000 description 1
MPLXQMMMGDYXIT-UHFFFAOYSA-N 7-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1NC(=O)C2=O MPLXQMMMGDYXIT-UHFFFAOYSA-N 0.000 description 1
244000198134 Agave sisalana Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100084503 Caenorhabditis elegans pas-3 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
238000012696 Interfacial polycondensation Methods 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
VCYAMSXIIWQHKV-UHFFFAOYSA-N bis(2,3,4-tribromophenyl) carbonate Chemical compound BrC1=C(Br)C(Br)=CC=C1OC(=O)OC1=CC=C(Br)C(Br)=C1Br VCYAMSXIIWQHKV-UHFFFAOYSA-N 0.000 description 1
DSEORJACOQDMQX-UHFFFAOYSA-N bis(2,3,4-trichlorophenyl) carbonate Chemical compound ClC1=C(Cl)C(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C(Cl)=C1Cl DSEORJACOQDMQX-UHFFFAOYSA-N 0.000 description 1
SJWFGMZZMOUDTF-UHFFFAOYSA-N bis(2-chloronaphthalen-1-yl) carbonate Chemical compound C1=CC=C2C(OC(=O)OC3=C4C=CC=CC4=CC=C3Cl)=C(Cl)C=CC2=C1 SJWFGMZZMOUDTF-UHFFFAOYSA-N 0.000 description 1
MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
POZGCGJFBOZPCM-UHFFFAOYSA-N bis(2-methylphenyl) carbonate Chemical compound CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1C POZGCGJFBOZPCM-UHFFFAOYSA-N 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004455 differential thermal analysis Methods 0.000 description 1
ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000005286 illumination Methods 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
229940090044 injection Drugs 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003055 poly(ester-imide) Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000009966 trimming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
- 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
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- 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
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
- 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
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Indole Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA242,504A 1975-01-03 1975-12-22 Polycarbonates thermoplastiques ramifies a poids moleculaire eleve Expired CA1064191A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2500092A DE2500092C3 (de)	1975-01-03	1975-01-03	Verzweigte, hochmolekulare, thermoplastische und lösliche Polycarbonate

Publications (1)

Publication Number	Publication Date
CA1064191A true CA1064191A (fr)	1979-10-09

Family

ID=5935917

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA242,504A Expired CA1064191A (fr)	1975-01-03	1975-12-22	Polycarbonates thermoplastiques ramifies a poids moleculaire eleve

Country Status (10)

Country	Link
JP (1)	JPS5439040B2 (fr)
BE (1)	BE837282A (fr)
BR (1)	BR7600007A (fr)
CA (1)	CA1064191A (fr)
DE (1)	DE2500092C3 (fr)
ES (1)	ES444056A1 (fr)
FR (1)	FR2296654A1 (fr)
GB (1)	GB1476108A (fr)
IT (1)	IT1052659B (fr)
NL (1)	NL176002C (fr)

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US8932684B2 (en)	2009-07-29	2015-01-13	Bayer Materialscience Ag	Multi-layer products comprising acrylate containing coatings
US8968610B2 (en)	2010-12-17	2015-03-03	Bayer Materialscience Ag	Polymer composition having heat-absorbing properties and high stability to weathering
US9029440B2 (en)	2010-12-17	2015-05-12	Bayer Materialscience Ag	Polymer composition having heat-absorbing properties and high stability to weathering

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1975
- 1975-01-03 DE DE2500092A patent/DE2500092C3/de not_active Expired
- 1975-10-31 GB GB4532175A patent/GB1476108A/en not_active Expired
- 1975-12-22 CA CA242,504A patent/CA1064191A/fr not_active Expired
- 1975-12-30 IT IT52910/75A patent/IT1052659B/it active
1976
- 1976-01-01 JP JP56476A patent/JPS5439040B2/ja not_active Expired
- 1976-01-02 ES ES444056A patent/ES444056A1/es not_active Expired
- 1976-01-02 NL NLAANVRAGE7600017,A patent/NL176002C/xx not_active IP Right Cessation
- 1976-01-02 FR FR7600029A patent/FR2296654A1/fr active Granted
- 1976-01-02 BR BR7600007A patent/BR7600007A/pt unknown
- 1976-01-02 BE BE163286A patent/BE837282A/fr unknown

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US8641784B2 (en)	2010-12-17	2014-02-04	Bayer Materialscience Ag	Organic colouring agents and coloured polymer compositions with a high stability to weathering
US8716374B2 (en)	2010-12-17	2014-05-06	Bayer Materialscience Ag	Colour-stable LED substrates
US8968610B2 (en)	2010-12-17	2015-03-03	Bayer Materialscience Ag	Polymer composition having heat-absorbing properties and high stability to weathering
US9029440B2 (en)	2010-12-17	2015-05-12	Bayer Materialscience Ag	Polymer composition having heat-absorbing properties and high stability to weathering
US9212272B2 (en)	2010-12-17	2015-12-15	Bayer Materialscience Ag	Organic colouring agents and coloured polymer compositions with a high stability to weathering

Also Published As

Publication number	Publication date
JPS5192893A (fr)	1976-08-14
JPS5439040B2 (fr)	1979-11-26
NL7600017A (nl)	1976-07-06
BE837282A (fr)	1976-07-02
FR2296654B1 (fr)	1979-07-27
NL176002C (nl)	1985-02-01
FR2296654A1 (fr)	1976-07-30
GB1476108A (en)	1977-06-10
NL176002B (nl)	1984-09-03
IT1052659B (it)	1981-07-20
DE2500092B2 (de)	1978-02-02
DE2500092A1 (de)	1976-07-08
BR7600007A (pt)	1976-08-03
ES444056A1 (es)	1977-04-16
DE2500092C3 (de)	1978-10-12

Publication	Publication Date	Title
CA1064191A (fr)	1979-10-09	Polycarbonates thermoplastiques ramifies a poids moleculaire eleve
US4185009A (en)	1980-01-22	Branched, high-molecular weight thermoplastic polycarbonates
US4894432A (en)	1990-01-16	Polycarbonate polymer from tetra arylene triphenol
TWI415874B (zh)	2013-11-21	具有改良之金屬黏附性之（共）聚碳酸酯類
US4152367A (en)	1979-05-01	Branched polyaryl-sulphone/polycarbonate mixtures and their use for the production of extruded films
JPH02222415A (ja)	1990-09-05	熱可塑性芳香族ポリカーボネート
US4059565A (en)	1977-11-22	Process for producing a branched polycarbonate or poly(ester-carbonate)
US4562242A (en)	1985-12-31	Branched polycarbonate from carboxy containing diphenol
US4960863A (en)	1990-10-02	Polycarbonate cross-linked resin
US4415724A (en)	1983-11-15	Branched aromatic polycarbonate from tetraphenol
JPH0379626A (ja)	1991-04-04	コーポリカーボネート樹脂およびその製法
US4306055A (en)	1981-12-15	Polycarbonates having sulfur-containing phenolic diols incorporated therein
US5021542A (en)	1991-06-04	Polycarbonate of polysubstituted cyclohexylidene bisphenols
US4260732A (en)	1981-04-07	UV Stabilized polycarbonate resins
JPS6284035A (ja)	1987-04-17	トリフエノ−ル系化合物
US4960839A (en)	1990-10-02	Method of making a polycarbonate cross-linked resin
EP0372323A2 (fr)	1990-06-13	Résine de réticulation à base de polycarbonate et composition ignifuge réalisée à partir de celle-ci
KR920010146B1 (ko)	1992-11-16	할로겐화된 거대고리 화합물로부터의 유도단위체를 함유한 방염 폴리카보네이트
JP2858462B2 (ja)	1999-02-17	シクロアルキリデンビスフエノールのポリカーボネート
JP4473446B2 (ja)	2010-06-02	分岐状ポリカーボネート樹脂
US5021541A (en)	1991-06-04	Polycarbonate resin from bis(hydroxy benzoyl oxy-tetra oxa spiro) cpd.
US4174437A (en)	1979-11-13	Process for the preparation of branched polycarbonates
JP3693462B2 (ja)	2005-09-07	分岐状ポリカーボネート樹脂及びその製造方法
JPWO1999028369A1 (ja)	2002-09-10	分岐状ポリカーボネート樹脂
US4515937A (en)	1985-05-07	Flame resistant sulfur-bearing copolycarbonate