CA1294387C - Preparation of organic polymers - Google Patents
Preparation of organic polymersInfo
- Publication number
- CA1294387C CA1294387C CA000475162A CA475162A CA1294387C CA 1294387 C CA1294387 C CA 1294387C CA 000475162 A CA000475162 A CA 000475162A CA 475162 A CA475162 A CA 475162A CA 1294387 C CA1294387 C CA 1294387C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- group
- reactant
- independently
- mol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- 229920000620 organic polymer Polymers 0.000 title abstract description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 115
- 238000000034 method Methods 0.000 claims abstract description 78
- 229920001577 copolymer Polymers 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 239000000376 reactant Substances 0.000 claims abstract description 33
- 239000006227 byproduct Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000012834 electrophilic reactant Substances 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 6
- -1 ether ketone Chemical class 0.000 claims description 35
- 229920000728 polyester Polymers 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- 230000000269 nucleophilic effect Effects 0.000 claims description 19
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052718 tin Inorganic materials 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 239000004952 Polyamide Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 14
- 239000004417 polycarbonate Substances 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229920001400 block copolymer Polymers 0.000 claims description 12
- 229920001955 polyphenylene ether Polymers 0.000 claims description 12
- 239000005864 Sulphur Substances 0.000 claims description 11
- 239000011574 phosphorus Chemical class 0.000 claims description 11
- 229910052698 phosphorus Chemical class 0.000 claims description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 125000001174 sulfone group Chemical group 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 229920001281 polyalkylene Polymers 0.000 claims description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 7
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 claims description 7
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 7
- 150000001805 chlorine compounds Chemical group 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229920001692 polycarbonate urethane Polymers 0.000 claims description 3
- 229910052716 thallium Chemical group 0.000 claims description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical group [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 150000002829 nitrogen Chemical class 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 79
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 60
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 39
- 229960001701 chloroform Drugs 0.000 description 36
- 238000010992 reflux Methods 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 28
- 235000013350 formula milk Nutrition 0.000 description 22
- 238000001914 filtration Methods 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 17
- 239000008096 xylene Substances 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 15
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 13
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 11
- 238000004566 IR spectroscopy Methods 0.000 description 10
- KJGLZJQPMKQFIK-UHFFFAOYSA-N methanolate;tributylstannanylium Chemical compound CCCC[Sn](CCCC)(CCCC)OC KJGLZJQPMKQFIK-UHFFFAOYSA-N 0.000 description 10
- 238000004611 spectroscopical analysis Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000001294 propane Substances 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 6
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920001634 Copolyester Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- XLAIWHIOIFKLEO-UHFFFAOYSA-N (E)-4-<2-(4-hydroxyphenyl)ethenyl>phenol Natural products C1=CC(O)=CC=C1C=CC1=CC=C(O)C=C1 XLAIWHIOIFKLEO-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- QOLALWJWCONGMG-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoropentanedioyl dichloride Chemical compound ClC(=O)C(F)(F)C(F)(F)C(F)(F)C(Cl)=O QOLALWJWCONGMG-UHFFFAOYSA-N 0.000 description 2
- FEAJSSRZWFESGG-OWOJBTEDSA-N 2-chloro-4-[(e)-2-(3-chloro-4-hydroxyphenyl)ethenyl]phenol Chemical compound C1=C(Cl)C(O)=CC=C1\C=C\C1=CC=C(O)C(Cl)=C1 FEAJSSRZWFESGG-OWOJBTEDSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZZBNZZCHSNOXOH-UHFFFAOYSA-N chloro(trimethyl)germane Chemical compound C[Ge](C)(C)Cl ZZBNZZCHSNOXOH-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940057952 methanol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- YCVPRTHEGLPYPB-UHFFFAOYSA-N pinosylvin Chemical compound OC1=CC(O)=CC(C=CC=2C=CC=CC=2)=C1 YCVPRTHEGLPYPB-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLAIWHIOIFKLEO-OWOJBTEDSA-N trans-stilbene-4,4'-diol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC=C(O)C=C1 XLAIWHIOIFKLEO-OWOJBTEDSA-N 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- OKJFKPFBSPZTAH-UHFFFAOYSA-N (2,4-dihydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O OKJFKPFBSPZTAH-UHFFFAOYSA-N 0.000 description 1
- PTBZRYBRVBHLCU-UHFFFAOYSA-N (2,5-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(O)C(C(=O)C=2C=CC=CC=2)=C1 PTBZRYBRVBHLCU-UHFFFAOYSA-N 0.000 description 1
- LATZCKQPCAXJJJ-NSCUHMNNSA-N (e)-2-methylbut-2-enedioyl dichloride Chemical compound ClC(=O)C(/C)=C/C(Cl)=O LATZCKQPCAXJJJ-NSCUHMNNSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- CWLGEPSKQDNHIO-JOBJLJCHSA-N (e)-n-[(e)-benzylideneamino]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1/C=N/N=C/C1=CC=CC=C1 CWLGEPSKQDNHIO-JOBJLJCHSA-N 0.000 description 1
- JSGSYRUEGRXIDF-UPHRSURJSA-N (z)-2,3-dibromobut-2-enedioyl dichloride Chemical compound ClC(=O)C(\Br)=C(\Br)C(Cl)=O JSGSYRUEGRXIDF-UPHRSURJSA-N 0.000 description 1
- JCNQHSWENHLPRQ-WAYWQWQTSA-N (z)-2,3-diethylbut-2-enedioyl dichloride Chemical compound CC\C(C(Cl)=O)=C(/CC)C(Cl)=O JCNQHSWENHLPRQ-WAYWQWQTSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 1
- DSZUZSDISUPSNE-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-diol Chemical compound C1=CC=C2C(O)=C(CCCC3)C3=C(O)C2=C1 DSZUZSDISUPSNE-UHFFFAOYSA-N 0.000 description 1
- UTCOUOISVRSLSH-UHFFFAOYSA-N 1,2-Anthracenediol Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C=C21 UTCOUOISVRSLSH-UHFFFAOYSA-N 0.000 description 1
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- 125000000732 arylene group Chemical group 0.000 description 1
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- ALDQRVOWVGRPCV-UHFFFAOYSA-N benzenethiol;tributyltin Chemical group SC1=CC=CC=C1.CCCC[Sn](CCCC)CCCC ALDQRVOWVGRPCV-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- VRPKUXAKHIINGG-UHFFFAOYSA-N biphenyl-4,4'-dithiol Chemical compound C1=CC(S)=CC=C1C1=CC=C(S)C=C1 VRPKUXAKHIINGG-UHFFFAOYSA-N 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- LAKDLYAMUUCEMZ-UHFFFAOYSA-N bis(3-chloro-4-hydroxyphenyl)methanone Chemical compound C1=C(Cl)C(O)=CC=C1C(=O)C1=CC=C(O)C(Cl)=C1 LAKDLYAMUUCEMZ-UHFFFAOYSA-N 0.000 description 1
- KLUPUCRALNWZLV-UHFFFAOYSA-N bis(4-hydroxy-2-methoxyphenyl)methanone Chemical compound COC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1OC KLUPUCRALNWZLV-UHFFFAOYSA-N 0.000 description 1
- KWKBGEYSGDAPGY-UHFFFAOYSA-N bis(4-hydroxy-3-methylphenyl)methanone Chemical compound C1=C(O)C(C)=CC(C(=O)C=2C=C(C)C(O)=CC=2)=C1 KWKBGEYSGDAPGY-UHFFFAOYSA-N 0.000 description 1
- HBSXOMANIQFJDD-UHFFFAOYSA-N bis(phenylsulfanyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OSC=2C=CC=CC=2)C=CC=1C(=O)OSC1=CC=CC=C1 HBSXOMANIQFJDD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- LCEFDICNHKVNSF-UHFFFAOYSA-N but-2-ynedioyl dichloride Chemical compound ClC(=O)C#CC(Cl)=O LCEFDICNHKVNSF-UHFFFAOYSA-N 0.000 description 1
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- 239000001569 carbon dioxide Substances 0.000 description 1
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- WKODVHZBYIBMOC-UHFFFAOYSA-N chembl116175 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(O)C=C1 WKODVHZBYIBMOC-UHFFFAOYSA-N 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 1
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- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical group C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- LSHSZIMRIAJWRM-UHFFFAOYSA-N oxolane-2,3-dicarbonyl chloride Chemical compound ClC(=O)C1CCOC1C(Cl)=O LSHSZIMRIAJWRM-UHFFFAOYSA-N 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DQSSGQQAPRAVCZ-UHFFFAOYSA-N perylene-1,2-diol Chemical group C1=CC(C2=C(C(O)=CC=3C2=C2C=CC=3)O)=C3C2=CC=CC3=C1 DQSSGQQAPRAVCZ-UHFFFAOYSA-N 0.000 description 1
- VSFGGPAWSZWOTI-UHFFFAOYSA-N phenazine-1,2-diol Chemical compound C1=CC=CC2=NC3=C(O)C(O)=CC=C3N=C21 VSFGGPAWSZWOTI-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 125000002743 phosphorus functional group Chemical group 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QKYIPVJKWYKQLX-UHFFFAOYSA-N pyrene-2,7-diol Chemical compound C1=C(O)C=C2C=CC3=CC(O)=CC4=CC=C1C2=C43 QKYIPVJKWYKQLX-UHFFFAOYSA-N 0.000 description 1
- WPNXWWLAOCWIDT-UHFFFAOYSA-N pyridine-2,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1C(Cl)=O WPNXWWLAOCWIDT-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- PYELIMVFIITPER-UHFFFAOYSA-N quinoline-4,8-diol Chemical compound C1=CC=C2C(O)=CC=NC2=C1O PYELIMVFIITPER-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- TWRYZRQZQIBEIE-UHFFFAOYSA-N tetramethoxystannane Chemical compound [Sn+4].[O-]C.[O-]C.[O-]C.[O-]C TWRYZRQZQIBEIE-UHFFFAOYSA-N 0.000 description 1
- GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical group [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical compound C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/26—Polythioesters
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/191—Hydroquinones
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
- C08G63/195—Bisphenol A
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/547—Hydroxy compounds containing aromatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6826—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
- C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
- C08G63/6956—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
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)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyamides (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicon Polymers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8405049 | 1984-02-27 | ||
| GB848405049A GB8405049D0 (en) | 1984-02-27 | 1984-02-27 | Organic polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1294387C true CA1294387C (en) | 1992-01-14 |
Family
ID=10557224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000475162A Expired - Lifetime CA1294387C (en) | 1984-02-27 | 1985-02-26 | Preparation of organic polymers |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US4845179A (en:Method) |
| EP (1) | EP0154506B1 (en:Method) |
| JP (1) | JPH0725894B2 (en:Method) |
| AT (1) | ATE72451T1 (en:Method) |
| AU (1) | AU585213B2 (en:Method) |
| CA (1) | CA1294387C (en:Method) |
| DE (1) | DE3585330D1 (en:Method) |
| ES (1) | ES8707984A1 (en:Method) |
| GB (1) | GB8405049D0 (en:Method) |
| IL (1) | IL74444A (en:Method) |
| IN (1) | IN164380B (en:Method) |
| ZA (1) | ZA851492B (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8405049D0 (en) * | 1984-02-27 | 1984-04-04 | Raychem Ltd | Organic polymers |
| GB8521324D0 (en) * | 1985-08-27 | 1985-10-02 | Raychem Ltd | Preparation of monomers |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| GB8521325D0 (en) * | 1985-08-27 | 1985-10-02 | Raychem Ltd | Preparation of side-chain polymers |
| US4975522A (en) * | 1988-06-07 | 1990-12-04 | Adademie der Wissenschaften der DDR | Crosslinkable compounds and method for making |
| US5001215A (en) * | 1989-11-02 | 1991-03-19 | Hoechst Celanese Corp. | Aromatic polyester from 1,3-bis(p-carboxyphenoxy)propane |
| US5336653A (en) * | 1992-11-03 | 1994-08-09 | Chisso Corporation | Catalyst for asymmetric synthesis |
| JP4771895B2 (ja) * | 2006-08-30 | 2011-09-14 | 株式会社リコー | 電子写真感光体、それを用いた画像形成方法、画像形成装置及び画像形成装置用プロセスカートリッジ |
| JP5084204B2 (ja) * | 2006-09-06 | 2012-11-28 | キヤノン株式会社 | 発光素子及び高分子混合金属錯体 |
| US7851579B2 (en) * | 2006-12-11 | 2010-12-14 | General Electric Company | Carbazolyl polymers for organic electronic devices |
| US7806275B2 (en) * | 2007-05-09 | 2010-10-05 | The United States Of America As Represented By The Secretary Of The Interior, The Bureau Of Reclamation | Chlorine resistant polyamides and membranes made from the same |
| WO2014012240A1 (en) * | 2012-07-20 | 2014-01-23 | Rhodia Operations | Novel polyamide, preparation process therefor and uses thereof |
| US11906901B2 (en) | 2021-06-07 | 2024-02-20 | International Business Machines Corporation | Alternating copolymer chain scission photoresists |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA786853A (en) * | 1968-06-04 | F. Klebe Johann | Organosilylated polyamic resins | |
| US2435429A (en) * | 1943-08-11 | 1948-02-03 | Shell Dev | Alkyd resins |
| DE861610C (de) * | 1946-11-02 | 1953-01-05 | Wingfoot Corp | Verfahren zur Herstellung von Polythioestern |
| FR83790E (fr) * | 1959-12-18 | 1964-10-09 | Kodak Pathe | Nouveaux polymères dérivés des 2, 2, 4, 4-tétraalcoyl-1, 3-cyclobutanediols et leurs applications industrielles |
| US3153010A (en) * | 1961-12-06 | 1964-10-13 | Monsanto Co | Process for preparing polyester amides in the presence of stannous oxalate catalyst |
| US3194791A (en) * | 1962-02-23 | 1965-07-13 | Eastman Kodak Co | Tin salts catalysts for polyesterification process |
| US3287285A (en) * | 1963-10-17 | 1966-11-22 | Hughes Aircraft Co | Chain extended stannosiloxanes and method |
| DE1239850B (de) * | 1964-10-14 | 1967-05-03 | Basf Ag | Verfahren zur Herstellung siliciumorganischer Bindemittel |
| US3408334A (en) * | 1965-04-05 | 1968-10-29 | Eastman Kodak Co | Preparation of polyamides from aromatic amino compounds |
| GB1137151A (en) * | 1965-04-05 | 1968-12-18 | Eastman Kodak Co | Polyamides |
| US3330872A (en) * | 1966-04-28 | 1967-07-11 | Monsanto Res Corp | Fluorine-containing hemiketals |
| US3539657A (en) * | 1968-03-21 | 1970-11-10 | Union Carbide Corp | Two-phase siloxane-polyarylene polyether block copolymers |
| US3480656A (en) * | 1969-03-18 | 1969-11-25 | Mobay Chemical Corp | N-tin carbamic acid derivatives |
| US3703564A (en) * | 1970-01-05 | 1972-11-21 | Gen Electric | Bis(polyphenylene oxide)-ester block copolymers |
| AU1792370A (en) * | 1970-04-29 | 1972-01-27 | Imperial Chemical Industries Limited | New polymers |
| US3706774A (en) * | 1971-02-02 | 1972-12-19 | M & T Chemicals Inc | Stannous glycoloxides |
| FR2128559A1 (en) * | 1971-03-04 | 1972-10-20 | Ici Ltd | Block copolymers - contg aromatic polymers and thermoplastic condensation polymers |
| US3898196A (en) * | 1974-02-14 | 1975-08-05 | Goodyear Tire & Rubber | Copolyesters of fluorine containing aliphatic dicarboxylic acids |
| US4072665A (en) * | 1976-03-08 | 1978-02-07 | The Upjohn Company | Polyamide from arylene diamine, isophthalic acid and alkylene dicarboxylic acid |
| US4075319A (en) * | 1976-06-24 | 1978-02-21 | The United States Of America As Represented By The Secretary Of The Navy | Low leaching antifouling organometallic polyvinyls |
| CA1102469A (en) * | 1976-12-20 | 1981-06-02 | General Electric Company | Flame retardant compositions comprising block copolyesters of polybutylene terephthalate |
| GB1569229A (en) * | 1976-12-20 | 1980-06-11 | Gen Electric | Block copolyesters of polybutylene terephthalate |
| US4129607A (en) * | 1977-05-31 | 1978-12-12 | Unitech Chemical Inc. | Hot melt adhesive having both high peel and tensile shear strength |
| DE2907613A1 (de) * | 1979-02-27 | 1980-09-04 | Basf Ag | Verfahren zur herstellung von aromatischen polyestern |
| US4245084A (en) * | 1979-05-07 | 1981-01-13 | Celanese Corporation | Thermotropic, wholly aromatic polythiolesters capable of forming an anisotropic melt and a process for preparing the polythiolesters |
| DE3015374A1 (de) * | 1980-04-22 | 1981-10-29 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von harnstoffen |
| US4358568A (en) | 1980-09-16 | 1982-11-09 | General Electric Company | Copolymers of polyarylates with polyethylene arylates and process for their preparation |
| JPS5773021A (en) * | 1980-10-24 | 1982-05-07 | Kanegafuchi Chem Ind Co Ltd | Heat-resistant aromatic polyester coplymer and its preparation |
| GB8405049D0 (en) * | 1984-02-27 | 1984-04-04 | Raychem Ltd | Organic polymers |
| US4611049A (en) * | 1984-06-07 | 1986-09-09 | Teijin Limited | Process for producing aromatic polyester |
| US4857630A (en) * | 1987-12-07 | 1989-08-15 | E. I. Du Pont De Nemours And Company | Hyperbranched polyarylene |
-
1984
- 1984-02-27 GB GB848405049A patent/GB8405049D0/en active Pending
-
1985
- 1985-02-26 ES ES540702A patent/ES8707984A1/es not_active Expired
- 1985-02-26 CA CA000475162A patent/CA1294387C/en not_active Expired - Lifetime
- 1985-02-26 IL IL74444A patent/IL74444A/xx not_active IP Right Cessation
- 1985-02-26 IN IN161/MAS/85A patent/IN164380B/en unknown
- 1985-02-27 EP EP85301326A patent/EP0154506B1/en not_active Expired - Lifetime
- 1985-02-27 AU AU39221/85A patent/AU585213B2/en not_active Ceased
- 1985-02-27 DE DE8585301326T patent/DE3585330D1/de not_active Expired - Lifetime
- 1985-02-27 AT AT85301326T patent/ATE72451T1/de not_active IP Right Cessation
- 1985-02-27 JP JP60040262A patent/JPH0725894B2/ja not_active Expired - Lifetime
- 1985-02-27 ZA ZA851492A patent/ZA851492B/xx unknown
-
1988
- 1988-10-12 US US07/257,159 patent/US4845179A/en not_active Expired - Fee Related
-
1989
- 1989-05-23 US US07/355,936 patent/US4960835A/en not_active Expired - Fee Related
-
1990
- 1990-07-25 US US07/557,883 patent/US4999411A/en not_active Expired - Fee Related
-
1991
- 1991-01-24 US US07/645,914 patent/US5128429A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60210633A (ja) | 1985-10-23 |
| IN164380B (en:Method) | 1989-03-04 |
| EP0154506A2 (en) | 1985-09-11 |
| ATE72451T1 (de) | 1992-02-15 |
| US4845179A (en) | 1989-07-04 |
| GB8405049D0 (en) | 1984-04-04 |
| AU585213B2 (en) | 1989-06-15 |
| AU3922185A (en) | 1985-09-05 |
| DE3585330D1 (de) | 1992-03-19 |
| ES540702A0 (es) | 1987-09-01 |
| EP0154506B1 (en) | 1992-02-05 |
| JPH0725894B2 (ja) | 1995-03-22 |
| US4960835A (en) | 1990-10-02 |
| IL74444A (en) | 1988-12-30 |
| ZA851492B (en) | 1986-10-29 |
| US5128429A (en) | 1992-07-07 |
| US4999411A (en) | 1991-03-12 |
| EP0154506A3 (en) | 1987-08-26 |
| ES8707984A1 (es) | 1987-09-01 |
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| Date | Code | Title | Description |
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| MKLA | Lapsed |