CA1055641A - Copolymeres thermoplastiques de polycarbonate de polysiloxane et constituants de polyesters - Google Patents

Copolymeres thermoplastiques de polycarbonate de polysiloxane et constituants de polyesters

Info

Publication number: CA1055641A
Authority: CA; Canada
Prior art keywords: dihydric phenol; organic acid; polysiloxane; phosgene; blocks
Prior art date: 1976-04-12
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

CA255,301A

Other languages

English (en)

Inventor

Dean G. Laurin

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.)

Baxter International Inc

Original Assignee

Baxter Travenol Laboratories Inc

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.)

1976-04-12

Filing date

1976-06-21

Publication date

1979-05-29

1976-04-12 Priority claimed from US05/675,799 external-priority patent/US3994988A/en

1976-06-21 Application filed by Baxter Travenol Laboratories Inc filed Critical Baxter Travenol Laboratories Inc

1979-05-29 Application granted granted Critical

1979-05-29 Publication of CA1055641A publication Critical patent/CA1055641A/fr

Status Expired legal-status Critical Current

Links

-1 polysiloxane Polymers 0.000 title claims abstract description 88
229920001296 polysiloxane Polymers 0.000 title claims abstract description 48
229920000728 polyester Polymers 0.000 title claims abstract description 11
239000004417 polycarbonate Substances 0.000 title claims abstract description 5
229920000515 polycarbonate Polymers 0.000 title claims abstract description 5
239000000470 constituent Substances 0.000 title abstract description 11
239000004416 thermosoftening plastic Substances 0.000 title abstract description 8
229920001169 thermoplastic Polymers 0.000 title abstract description 6
229920001577 copolymer Polymers 0.000 claims abstract description 73
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 36
238000006243 chemical reaction Methods 0.000 claims abstract description 30
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 26
239000002243 precursor Substances 0.000 claims abstract description 13
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 45
238000000034 method Methods 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 23
239000000463 material Substances 0.000 claims description 21
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 13
239000000047 product Substances 0.000 claims description 12
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical group [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 12
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 10
229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 9
238000007789 sealing Methods 0.000 claims description 8
239000012467 final product Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
239000004033 plastic Substances 0.000 claims description 6
229920003023 plastic Polymers 0.000 claims description 6
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 claims description 5
239000004205 dimethyl polysiloxane Substances 0.000 claims description 5
235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 5
229920005645 diorganopolysiloxane polymer Polymers 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
238000001125 extrusion Methods 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 18
239000002904 solvent Substances 0.000 abstract description 15
239000003153 chemical reaction reagent Substances 0.000 abstract description 10
150000004820 halides Chemical class 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 8
239000003054 catalyst Substances 0.000 abstract description 8
150000007860 aryl ester derivatives Chemical class 0.000 abstract description 3
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 2
239000003960 organic solvent Substances 0.000 abstract 1
238000012643 polycondensation polymerization Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
229940106691 bisphenol a Drugs 0.000 description 17
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000306 component Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
239000008280 blood Substances 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
229920000642 polymer Polymers 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
238000013019 agitation Methods 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
239000007789 gas Substances 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
230000006835 compression Effects 0.000 description 4
238000007906 compression Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000035699 permeability Effects 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
150000003457 sulfones Chemical class 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
LRNRWPYXVVMMLQ-UHFFFAOYSA-N carbonic acid;terephthalic acid Chemical compound OC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 LRNRWPYXVVMMLQ-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000835 fiber Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
230000001954 sterilising effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000009864 tensile test Methods 0.000 description 3
238000012546 transfer Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
JHOPNNNTBHXSHY-UHFFFAOYSA-N 2-(4-hydroxyphenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1O JHOPNNNTBHXSHY-UHFFFAOYSA-N 0.000 description 2
LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
229930185605 Bisphenol Natural products 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000008378 aryl ethers Chemical class 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
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KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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125000005270 trialkylamine group Chemical group 0.000 description 2
SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
GPASWZHHWPVSRG-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C)C=C1O GPASWZHHWPVSRG-UHFFFAOYSA-N 0.000 description 1
OTLMQCNHFVYECA-UHFFFAOYSA-N 2-(2-carboxybenzoyl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1C(O)=O OTLMQCNHFVYECA-UHFFFAOYSA-N 0.000 description 1
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
CGFCKPWPXHKFPU-UHFFFAOYSA-N 3-chloro-4-[1-(2-chloro-4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=C(Cl)C=1C(C)C1=CC=C(O)C=C1Cl CGFCKPWPXHKFPU-UHFFFAOYSA-N 0.000 description 1
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IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 1
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AMBWAOVSEACQJG-UHFFFAOYSA-N 4-[4-[4-(4-hydroxyphenyl)phenyl]phenyl]phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)C=C1 AMBWAOVSEACQJG-UHFFFAOYSA-N 0.000 description 1
YZYGDZRBLOLVDY-UHFFFAOYSA-N 4-[cyclohexyl-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1CCCCC1 YZYGDZRBLOLVDY-UHFFFAOYSA-N 0.000 description 1
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
AOHHHMKJDRSAFF-UHFFFAOYSA-N N,N-dibutyl-3,4-diethyl-6,6-dipropylnonan-3-amine Chemical class C(C)C(C(N(CCCC)CCCC)(CC)CC)CC(CCC)(CCC)CCC AOHHHMKJDRSAFF-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical group [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
229920001234 Polybisphenol-A terephthalate Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
ZXQYGBMAQZUVMI-QQDHXZELSA-N [cyano-(3-phenoxyphenyl)methyl] (1r,3r)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-QQDHXZELSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005376 alkyl siloxane group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910000410 antimony oxide Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
TXNQQGFCDIJFSI-UHFFFAOYSA-N benzene-1,3-diol carbonyl dichloride Chemical compound C1(O)=CC(O)=CC=C1.C(=O)(Cl)Cl TXNQQGFCDIJFSI-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000013060 biological fluid Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 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
239000012503 blood component Substances 0.000 description 1
239000010951 brass Substances 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000004087 circulation Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
125000005028 dihydroxyaryl group Chemical group 0.000 description 1
150000005205 dihydroxybenzenes Chemical class 0.000 description 1
HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical group CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000012246 gene addition Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940071643 prefilled syringe Drugs 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 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
150000003222 pyridines Chemical class 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
125000005023 xylyl group Chemical group 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- 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
- 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

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)

CA255,301A 1976-04-12 1976-06-21 Copolymeres thermoplastiques de polycarbonate de polysiloxane et constituants de polyesters Expired CA1055641A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/675,799 US3994988A (en)	1975-03-10	1976-04-12	Thermoplastic copolymers of polysiloxane polycarbonate and polyester constituents

Publications (1)

Publication Number	Publication Date
CA1055641A true CA1055641A (fr)	1979-05-29

Family

ID=24712022

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA255,301A Expired CA1055641A (fr)	1976-04-12	1976-06-21	Copolymeres thermoplastiques de polycarbonate de polysiloxane et constituants de polyesters

Country Status (3)

Country	Link
CA (1)	CA1055641A (fr)
DE (1)	DE2640241A1 (fr)
GB (1)	GB1580128A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10272639B2 (en)	2015-03-23	2019-04-30	Emd Millipore Corporation	Abrasion resistant film for biocontainers

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3344911A1 (de) *	1983-12-13	1985-06-13	Bayer Ag, 5090 Leverkusen	Thermoplastische polysiloxan-polyester(carbonat)-blockcopolymere, ihre herstellung und verwendung
DE3838106A1 (de) *	1988-11-10	1990-05-17	Bayer Ag	Thermoplastische polyestercarbonat-polysiloxan-blockcopolymere
DE3929401A1 (de) *	1989-09-05	1991-03-07	Bayer Ag	Thermoplastische polyestercarbonat-polysiloxan-blockcopolymere
DE4113292A1 (de) *	1991-04-24	1992-10-29	Bayer Ag	Optisch klare block(polydiorganosiloxan-co-poly(ester) -carbonate) zur herstellung von ophthalmischen formkoerpern
US8870814B2 (en)	2003-07-31	2014-10-28	Boston Scientific Scimed, Inc.	Implantable or insertable medical devices containing silicone copolymer for controlled delivery of therapeutic agent

1976
- 1976-06-21 CA CA255,301A patent/CA1055641A/fr not_active Expired
- 1976-09-07 DE DE19762640241 patent/DE2640241A1/de active Pending
1977
- 1977-03-07 GB GB944177A patent/GB1580128A/en not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10272639B2 (en)	2015-03-23	2019-04-30	Emd Millipore Corporation	Abrasion resistant film for biocontainers
US10675836B2 (en)	2015-03-23	2020-06-09	Emd Millipore Corporation	Abrasion resistant film for biocontainers
US11110684B2 (en)	2015-03-23	2021-09-07	Emd Millipore Corporation	Abrasion resistant film for biocontainers

Also Published As

Publication number	Publication date
GB1580128A (en)	1980-11-26
DE2640241A1 (de)	1977-10-20

Publication	Publication Date	Title
US3994988A (en)	1976-11-30	Thermoplastic copolymers of polysiloxane polycarbonate and polyester constituents
US5109076A (en)	1992-04-28	Polydiorganosiloxane/polycarbonate block cocondensates based on certain dihydroxydiphenylcycloalkanes
US3781378A (en)	1973-12-25	High temperature membrane materials
US3821325A (en)	1974-06-28	Organopolysiloxane-polycarbonate block copolymers
US4333809A (en)	1982-06-08	Cross-linkable polycarbonate elastomers, a process for their preparation and use for packaging medicines
EP3406648B1 (fr)	2022-10-19	Copolymère de polyester-polycarbonate et son procédé de production
CA2013923A1 (fr)	1990-12-16	Compositions de polymeres bloques polycarbonate-silicone
US4374233A (en)	1983-02-15	Block copolymers of polyphenylene oxides and non-sterically-hindered high molecular weight aromatic polycarbonates
KR101432616B1 (ko)	2014-08-21	내화학성 열가소성 수지 조성물 및 그로부터 제조된 성형품
US4681922A (en)	1987-07-21	Thermoplastic polysiloxane-polyester (carbonate) block copolymers, their preparation and use
JPH0753702A (ja)	1995-02-28	シロキサンポリカーボネートブロックコポリマーと耐熱性ポリカーボネートの組成物
EP1836235B1 (fr)	2010-11-17	Polycarbonates dotes de groupes terminaux carbonate de fluoroalkylene
CA1174395A (fr)	1984-09-11	Resine de polycarbonate offrant une meilleure resistance aux chocs, contenant des polyolefines et des corps fluides a base d'organopolysiloxannes
US3087908A (en)	1963-04-30	Resinous mixture comprising a polycarbonate and an organopolysiloxane
CN101087828A (zh)	2007-12-12	具有含氟亚烷基碳酸酯端基的聚碳酸酯
CN115124707A (zh)	2022-09-30	一种含磷硅共聚聚碳酸酯及其制备方法与应用
KR20140146694A (ko)	2014-12-29	난연성과 투명성이 우수한 열가소성 공중합체 수지 및 그 제조방법
EP2788428A2 (fr)	2014-10-15	Mélanges de polyphénylène éther sulfone et de polyester carbonate
KR900004584B1 (ko)	1990-06-30	테트라브로모 비스페놀계 폴리에스테르 카보네이트 격막
GB1580128A (en)	1980-11-26	Thermoplastic copolymers of polysiloxane polycarbonate and polyester constituents
Merrill	1961	Block copolymers based on 2, 2‐bis (4‐hydroxyphenyl)‐propane polycarbonate. I. Preparation and properties of copolymers from a variety of homopolymers
EP3398984A1 (fr)	2018-11-07	Nouveau polyorganosiloxane et copolycarbonate préparé au moyen de celui-ci
JPH06299079A (ja)	1994-10-25	エポキシ末端分岐状シリコーン及びそれらの共重合体
EP0418377A4 (en)	1993-01-13	Process for the preparation of polycarbonate and/or polyarylate block copolymers with poly(aryl ethers)
KR101184801B1 (ko)	2012-09-20	실록산 화합물 및 이를 이용하여 제조된 분지상 폴리카보네이트