CA1046693A - Polycarbonates containing s-triazine compounds as linking members between two molecules of bis-hydroxy aromatic compounds - Google Patents

Polycarbonates containing s-triazine compounds as linking members between two molecules of bis-hydroxy aromatic compounds

Info

Publication number: CA1046693A
Authority: CA; Canada
Prior art keywords: formula; bis; compounds; carbon atoms; compound
Prior art date: 1973-09-18
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

CA207,743A

Other languages

English (en)

French (fr)

Other versions

CA207743S (en

Inventor

Dieter Neuray

Hugo Vernaleken

Hans Rudolph

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.)

1973-09-18

Filing date

1974-08-26

Publication date

1979-01-16

1974-08-26 Application filed by Bayer AG filed Critical Bayer AG

1979-01-16 Application granted granted Critical

1979-01-16 Publication of CA1046693A publication Critical patent/CA1046693A/en

Status Expired legal-status Critical Current

Links

239000004417 polycarbonate Substances 0.000 title claims abstract description 98
229920000515 polycarbonate Polymers 0.000 title claims abstract description 93
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 title claims abstract description 44
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
125000003118 aryl group Chemical group 0.000 claims abstract description 40
229910052799 carbon Inorganic materials 0.000 claims abstract description 11
229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
150000002430 hydrocarbons Chemical class 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 114
150000001875 compounds Chemical class 0.000 claims description 83
-1 alkylene radicals Chemical class 0.000 claims description 67
239000000243 solution Substances 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 51
238000006243 chemical reaction Methods 0.000 claims description 41
238000000034 method Methods 0.000 claims description 32
238000002360 preparation method Methods 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 23
150000003254 radicals Chemical class 0.000 claims description 23
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 13
229910052783 alkali metal Inorganic materials 0.000 claims description 13
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
229910006069 SO3H Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
150000008282 halocarbons Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 4
REJHVSOVQBJEBF-UHFFFAOYSA-N 5-azaniumyl-2-[2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
UHVIHQSYQVURFV-UHFFFAOYSA-N 4,6-dichlorotriazin-5-amine Chemical class NC1=C(Cl)N=NN=C1Cl UHVIHQSYQVURFV-UHFFFAOYSA-N 0.000 claims description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
229940125773 compound 10 Drugs 0.000 claims description 3
125000002993 cycloalkylene group Chemical group 0.000 claims description 3
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
YJUUYXCFKWWRDE-UHFFFAOYSA-N 2,4-dichloro-6-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical group ClC1=NC(Cl)=NC(C=2N=CN=CN=2)=N1 YJUUYXCFKWWRDE-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims 4
238000002955 isolation Methods 0.000 claims 4
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 3
CASHWAGXBJSQDV-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical group C1=NC=NC(C=2N=CN=CN=2)=N1 CASHWAGXBJSQDV-UHFFFAOYSA-N 0.000 claims 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 2
125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
229940125797 compound 12 Drugs 0.000 claims 2
150000005840 aryl radicals Chemical class 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 14
125000000524 functional group Chemical group 0.000 abstract description 7
229910052757 nitrogen Inorganic materials 0.000 abstract description 7
239000002904 solvent Substances 0.000 abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 4
239000005864 Sulphur Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
238000000576 coating method Methods 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 4
239000001301 oxygen Substances 0.000 abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 abstract description 4
229920005989 resin Polymers 0.000 abstract description 2
239000011347 resin Substances 0.000 abstract description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
229940106691 bisphenol a Drugs 0.000 description 46
239000000047 product Substances 0.000 description 29
239000002244 precipitate Substances 0.000 description 26
229940086542 triethylamine Drugs 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000002253 acid Substances 0.000 description 19
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 19
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 17
229960004050 aminobenzoic acid Drugs 0.000 description 15
239000012071 phase Substances 0.000 description 15
239000000725 suspension Substances 0.000 description 15
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
229930185605 Bisphenol Natural products 0.000 description 13
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
235000015110 jellies Nutrition 0.000 description 9
239000008274 jelly Substances 0.000 description 9
230000007935 neutral effect Effects 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 8
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
235000011007 phosphoric acid Nutrition 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
229940060038 chlorine Drugs 0.000 description 6
235000017168 chlorine Nutrition 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000000499 gel Substances 0.000 description 6
239000013067 intermediate product Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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 5
229960002684 aminocaproic acid Drugs 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
229960002449 glycine Drugs 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical class ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000012266 salt solution Substances 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 3
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 3
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000004471 Glycine Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
229960004275 glycolic acid Drugs 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 2
IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical class NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 2
QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 2
MTBNVBBMBVPJHP-UHFFFAOYSA-N 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 MTBNVBBMBVPJHP-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
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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
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
- C08G18/4638—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/4661—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring

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)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Water Treatment By Sorption (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA207,743A 1973-09-18 1974-08-26 Polycarbonates containing s-triazine compounds as linking members between two molecules of bis-hydroxy aromatic compounds Expired CA1046693A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732346935 DE2346935C2 (de)	1973-09-18	1973-09-18	s-Triazinringe enthaltende Polycarbonate mit funktionellen Gruppen, ihre Herstellung und Verwendung

Publications (1)

Publication Number	Publication Date
CA1046693A true CA1046693A (en)	1979-01-16

Family

ID=5892945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA207,743A Expired CA1046693A (en)	1973-09-18	1974-08-26	Polycarbonates containing s-triazine compounds as linking members between two molecules of bis-hydroxy aromatic compounds

Country Status (8)

Country	Link
JP (3)	JPS5110895A (it)
BE (1)	BE819942A (it)
CA (1)	CA1046693A (it)
DE (1)	DE2346935C2 (it)
FR (1)	FR2243960B1 (it)
GB (1)	GB1460205A (it)
IT (1)	IT1019276B (it)
NL (1)	NL7412358A (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4999538U (it) *	1972-12-14	1974-08-28
DE2718466A1 (de) *	1977-04-26	1978-11-02	Bayer Ag	Verfahren zur herstellung von verzweigten polycarbonaten
DE3138179A1 (de) *	1981-09-25	1983-04-14	Bayer Ag, 5090 Leverkusen	Verfahren zur isolierung von polycarbonaten auf basis von 4,4'-dihydroxidiphenylsulfonen
CN103739879B (zh) *	2013-12-10	2016-01-20	青岛天人环境股份有限公司	一种普鲁兰多糖-淀粉基可降解薄膜及其制备方法
JP7593102B2 (ja) *	2019-12-26	2024-12-03	三菱ケミカル株式会社	芳香族ポリシアヌレートの製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1495141A1 (de) *	1963-09-14	1969-03-27	Basf Ag	Verfahren zum Herstellen von Triazinringe enthaltenden Polymeren
US3541049A (en) *	1969-08-21	1970-11-17	Mobay Chemical Corp	Cyanuric chloride branched polycarbonates

1973
- 1973-09-18 DE DE19732346935 patent/DE2346935C2/de not_active Expired
1974
- 1974-08-26 CA CA207,743A patent/CA1046693A/en not_active Expired
- 1974-09-16 BE BE148550A patent/BE819942A/xx unknown
- 1974-09-16 IT IT5302274A patent/IT1019276B/it active
- 1974-09-17 GB GB4044674A patent/GB1460205A/en not_active Expired
- 1974-09-18 NL NL7412358A patent/NL7412358A/xx unknown
- 1974-09-18 JP JP10681474A patent/JPS5110895A/ja active Granted
- 1974-09-18 FR FR7431556A patent/FR2243960B1/fr not_active Expired
1980
- 1980-10-06 JP JP13886980A patent/JPS56121636A/ja active Pending
1982
- 1982-03-10 JP JP3671382A patent/JPS6025049B2/ja not_active Expired

Also Published As

Publication number	Publication date
GB1460205A (en)	1976-12-31
NL7412358A (nl)	1975-03-20
FR2243960A1 (it)	1975-04-11
IT1019276B (it)	1977-11-10
DE2346935A1 (de)	1975-04-03
JPS5823825A (ja)	1983-02-12
FR2243960B1 (it)	1979-02-16
BE819942A (fr)	1975-03-17
JPS56121636A (en)	1981-09-24
DE2346935C2 (de)	1982-01-21
JPS5761045B2 (it)	1982-12-22
JPS6025049B2 (ja)	1985-06-15
JPS5110895A (en)	1976-01-28

Publication	Publication Date	Title
US3879347A (en)	1975-04-22	High molecular, statistical copolycarbonates
US3879348A (en)	1975-04-22	Saponification-resistant polycarbonates
US3912688A (en)	1975-10-14	Flameproof polycarbonates
US4188475A (en)	1980-02-12	Process for the preparation of flame-retardant polycarbonates
CA1046693A (en)	1979-01-16	Polycarbonates containing s-triazine compounds as linking members between two molecules of bis-hydroxy aromatic compounds
US3378523A (en)	1968-04-16	Bisphenol polyesters containing phosphorus
EP0146836A2 (en)	1985-07-03	Copolyester-carbonate resins
EP0146880B1 (en)	1989-08-02	Copolyester-carbonate resins exhibiting improved processability
CA1127795A (en)	1982-07-13	Method for manufacture of aromatic polyester-polycarbonate
US4092243A (en)	1978-05-30	Polycarbonates
US3894991A (en)	1975-07-15	High molecular polycarbonates containing s-triazine rings
US3957728A (en)	1976-05-18	Polycarbonates
JP3205848B2 (ja)	2001-09-04	ポリエ−テル樹脂及びその製造方法
US4404351A (en)	1983-09-13	Process for the isolation of polycarbonates based on 4,4'-dihydroxydiphenyl sulphones
US3251803A (en)	1966-05-17	Linear condensation polymers containing urethane and carbonate units
US3897391A (en)	1975-07-29	Process for preparing polycarbonate
US4139687A (en)	1979-02-13	Cyclic carbonate trimer of 2,2-bis(4-hydroxyphenyl)-1,1-dichloroethylene
EP0146076A2 (en)	1985-06-26	Copolyester-carbonate resins
US4906725A (en)	1990-03-06	Polycarbonate containing spiro dilactam segment
EP0425049A2 (en)	1991-05-02	Polythiocarbonates and a process for their preparation
CA1039442A (en)	1978-09-26	Flame-resistant, thermoplastic polyesters
US5145939A (en)	1992-09-08	Dihydroxy-meta-terphenyl polycarbonate
EP0350088B1 (en)	1994-12-21	Flame-resistant polycarbonates containing units derived from halogenated triphenyl compounds
KR0170080B1 (ko)	1999-03-30	난연성 전방향족 폴리에스테르 및 그의 제조방법
JPH0267316A (ja)	1990-03-07	熱可塑性、分枝状の高分子量ポリカーボネート及びその製法