CH492748A - Procédé de préparation de polymères de l'oxyméthylène par polymérisation cationique - Google Patents

Procédé de préparation de polymères de l'oxyméthylène par polymérisation cationique

Info

Publication number: CH492748A
Authority: CH; Switzerland
Prior art keywords: trioxane; antimony; catalyst; oxymethylene; triphenylmethyl
Prior art date: 1966-09-16

Application number

CH1243867A

Other languages

English (en)

French (fr)

Inventor

Anthony De Fazio Charles

Burton Price Martin

Original Assignee

Celanese Corp

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.)

1966-09-16

Filing date

1967-09-06

Publication date

1970-06-30

1967-09-06 Application filed by Celanese Corp filed Critical Celanese Corp

1970-06-30 Publication of CH492748A publication Critical patent/CH492748A/fr

Links

239000003054 catalyst Substances 0.000 title claims abstract description 69
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims abstract description 12
125000002091 cationic group Chemical group 0.000 title 1
229920001577 copolymer Polymers 0.000 claims abstract description 45
150000001875 compounds Chemical class 0.000 claims abstract description 41
150000004292 cyclic ethers Chemical class 0.000 claims abstract description 27
239000000203 mixture Substances 0.000 claims abstract description 15
125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 45
238000000034 method Methods 0.000 claims description 40
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
-1 phenyl radicals Chemical class 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
239000002685 polymerization catalyst Substances 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 18
230000008569 process Effects 0.000 claims description 18
239000000178 monomer Substances 0.000 claims description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
SFLGHFVLKDOXEF-UHFFFAOYSA-N C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)[Sb] Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)[Sb] SFLGHFVLKDOXEF-UHFFFAOYSA-N 0.000 claims description 14
238000010538 cationic polymerization reaction Methods 0.000 claims description 11
229910052787 antimony Inorganic materials 0.000 claims description 10
238000007334 copolymerization reaction Methods 0.000 claims description 9
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 8
150000005840 aryl radicals Chemical class 0.000 claims description 7
229920001519 homopolymer Polymers 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 3
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000006386 neutralization reaction Methods 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 6
229920000642 polymer Polymers 0.000 description 47
KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 44
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
238000006116 polymerization reaction Methods 0.000 description 24
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 21
229910015900 BF3 Inorganic materials 0.000 description 16
230000006641 stabilisation Effects 0.000 description 16
238000011105 stabilization Methods 0.000 description 16
239000000243 solution Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
230000035484 reaction time Effects 0.000 description 8
229920001897 terpolymer Polymers 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000007792 addition Methods 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
238000005406 washing Methods 0.000 description 7
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
230000001588 bifunctional effect Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
125000005702 oxyalkylene group Chemical group 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical group 0.000 description 4
239000007788 liquid Substances 0.000 description 4
JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 3
BGCSUUSPRCDKBQ-UHFFFAOYSA-N 2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OCOCC21COCOC2 BGCSUUSPRCDKBQ-UHFFFAOYSA-N 0.000 description 3
ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910052797 bismuth Inorganic materials 0.000 description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
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 2
239000002775 capsule Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
230000008570 general process Effects 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
238000007654 immersion Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
239000013638 trimer Substances 0.000 description 2
GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
ULAGGPJVDRGWTI-UHFFFAOYSA-N 1,3,5-trioxepane Chemical compound C1COCOCO1 ULAGGPJVDRGWTI-UHFFFAOYSA-N 0.000 description 1
GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
MQWSHBCKOSWEFJ-UHFFFAOYSA-N CC[P] Chemical compound CC[P] MQWSHBCKOSWEFJ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
BGVBFRLDGWSYDA-UHFFFAOYSA-N O.O.O.B(F)(F)F Chemical compound O.O.O.B(F)(F)F BGVBFRLDGWSYDA-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010923 batch production Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
RAQGPBPLJWJAFE-UHFFFAOYSA-N bismuth;ethane Chemical compound CC[Bi] RAQGPBPLJWJAFE-UHFFFAOYSA-N 0.000 description 1
229940106691 bisphenol a Drugs 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000011951 cationic catalyst Substances 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000007872 degassing Methods 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
229910001651 emery Inorganic materials 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
QKODANAAHZUYET-UHFFFAOYSA-N ethylantimony Chemical compound CC[Sb] QKODANAAHZUYET-UHFFFAOYSA-N 0.000 description 1
KQTKYCXEDDECIZ-UHFFFAOYSA-N ethylarsenic Chemical compound CC[As] KQTKYCXEDDECIZ-UHFFFAOYSA-N 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229960000587 glutaral Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000011068 loading method Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
PKFBLQVMCGBBCG-UHFFFAOYSA-N methyl(diphenyl)stibane Chemical compound C=1C=CC=CC=1[Sb](C)C1=CC=CC=C1 PKFBLQVMCGBBCG-UHFFFAOYSA-N 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
SXUXONJXVIQGLC-UHFFFAOYSA-N oxathiirane 2,2-dioxide Chemical compound O=S1(=O)CO1 SXUXONJXVIQGLC-UHFFFAOYSA-N 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
229960003868 paraldehyde Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010008 shearing Methods 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/10—Polymerisation of cyclic oligomers of formaldehyde

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Polyethers (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

CH1243867A 1966-09-16 1967-09-06 Procédé de préparation de polymères de l'oxyméthylène par polymérisation cationique CH492748A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57985766A	1966-09-16	1966-09-16

Publications (1)

Publication Number	Publication Date
CH492748A true CH492748A (fr)	1970-06-30

Family

ID=24318635

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1243867A CH492748A (fr)	1966-09-16	1967-09-06	Procédé de préparation de polymères de l'oxyméthylène par polymérisation cationique

Country Status (10)

Country	Link
AT (1)	AT276757B (pl)
BE (1)	BE703582A (pl)
CH (1)	CH492748A (pl)
DE (1)	DE1720409A1 (pl)
ES (1)	ES344669A1 (pl)
GB (1)	GB1187233A (pl)
IL (1)	IL28509A (pl)
LU (1)	LU54309A1 (pl)
NL (1)	NL6712302A (pl)
SE (1)	SE352645B (pl)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1054861B (de) *	1956-06-22	1959-04-09	Opel Adam Ag	Lagerschmierung fuer die Welle des Antriebsritzels bei Kegel- und Kegelschraubgetrieben, insbesondere in Vorderachsgetrieben von Kraftfahrzeugen
DE10215978A1 (de)	2002-04-11	2003-10-23	Basf Ag	Herstellung von Polyoxymethylen und dafür geeignete Katalysatoren
DE10215973A1 (de) *	2002-04-11	2003-10-23	Basf Ag	Herstellung von Polyoxymethylen und dafür geeignete Katalysatoren II
DE102009014316B4 (de)	2009-03-25	2019-03-14	Sew-Eurodrive Gmbh & Co Kg	Getriebe
DE102009014317A1 (de)	2009-03-25	2010-10-07	Sew-Eurodrive Gmbh & Co. Kg	Getriebe
DE102009014315B4 (de)	2009-03-25	2018-01-25	Sew-Eurodrive Gmbh & Co Kg	Getriebe
DE102009061042B4 (de)	2009-03-25	2024-11-14	Sew-Eurodrive Gmbh & Co Kg	Zumindest teilweise mit Öl befülltes Getriebe

1967
- 1967-08-14 LU LU54309D patent/LU54309A1/xx unknown
- 1967-08-15 IL IL28509A patent/IL28509A/en unknown
- 1967-08-31 ES ES344669A patent/ES344669A1/es not_active Expired
- 1967-08-31 GB GB39869/67A patent/GB1187233A/en not_active Expired
- 1967-09-02 DE DE19671720409 patent/DE1720409A1/de active Pending
- 1967-09-06 AT AT815667A patent/AT276757B/de not_active IP Right Cessation
- 1967-09-06 CH CH1243867A patent/CH492748A/fr not_active IP Right Cessation
- 1967-09-07 BE BE703582D patent/BE703582A/xx unknown
- 1967-09-07 NL NL6712302A patent/NL6712302A/xx unknown
- 1967-09-15 SE SE12748/67A patent/SE352645B/xx unknown

Also Published As

Publication number	Publication date
BE703582A (pl)	1968-03-07
GB1187233A (en)	1970-04-08
LU54309A1 (pl)	1967-12-07
AT276757B (de)	1969-12-10
IL28509A (en)	1971-05-26
ES344669A1 (es)	1968-10-16
NL6712302A (pl)	1968-03-18
DE1720409A1 (de)	1971-06-16
SE352645B (pl)	1973-01-08

Legal Events

Date	Code	Title	Description
1972-04-14	PL	Patent ceased

Publication	Publication Date	Title
EP1752482B1 (en)	2011-04-20	Aliphatic polyester copolymer
CN104837890B (zh)	2016-08-17	经高分子量化的芳香族聚碳酸酯树脂的制造方法
JP2014502306A (ja)	2014-01-30	イソソルビド含有ポリカーボネート、及びその調製
CH492748A (fr)	1970-06-30	Procédé de préparation de polymères de l'oxyméthylène par polymérisation cationique
EP2694568B1 (fr)	2015-11-25	Procede de fabrication de polycarbonate a partir de derives de dianhydrohexitols portant deux fonctions carbonate d'alkyle
EP2694569B1 (fr)	2015-11-04	Procede de fabrication de polycarbonate a partir de dialkylcarbonate de dianhydrohexitol
JP2008533265A (ja)	2008-08-21	ポリオキシメチレンの製造方法
US3442864A (en)	1969-05-06	Formals of norbornane-2,7-diols and copolymers thereof with trioxane
US3293219A (en)	1966-12-20	Polyacetal terpolymers containing randomly recurring groups derived from a methylene-bis-
JP5419450B2 (ja)	2014-02-19	ポリオキシメチレンの製造法
EP0308186A2 (en)	1989-03-22	Low Tg non-crystalline acetal copolymers
US4898925A (en)	1990-02-06	Elastomeric acetal polymers
EP3673003B1 (fr)	2021-12-08	Polymeres multiblocs dont la synthese met en oeuvre d'oligocarbonates polyols
DE19612139A1 (de)	1997-10-02	Zweistufenverfahren zur Herstellung von thermoplastischem Polycarbonat
JPH0570584A (ja)	1993-03-23	脂環式ポリカーボネートおよびその製造方法
US4937312A (en)	1990-06-26	Process for producing elastomeric acetal polymers
JP2005526880A (ja)	2005-09-08	ポリオキシメチレンの製造及びそのために適当な触媒（ｉｉｉ）
US5045607A (en)	1991-09-03	Acetal polymer blends
US3369039A (en)	1968-02-13	Process for the production of siliconcontaining trioxane copolymers
US3293211A (en)	1966-12-20	Process for the production of high molecular weight linear organo-silicic acid arylene polyesters
US7064177B2 (en)	2006-06-20	Production of polyoxymethylene and suitable (II) catalysts
JPH0578461A (ja)	1993-03-30	脂環式ポリマーの製造方法
WO2019077252A1 (fr)	2019-04-25	Oligocarbonates dimethacryles ou diacryles obtenus a partir de dialkylcarbonate de dinahydrohexitol ou un dimere de carbonate de dianhydrohexitol, leur procede de fabrication et leurs utilisations
US3539477A (en)	1970-11-10	Graft polymers of cellulose esters and process for their manufacture
KR100763987B1 (ko)	2007-10-08	지방족 폴리에스테르 공중합체