DE1256896B - Verfahren zur Herstellung von Copolymerisaten des Formaldehyds - Google Patents
Verfahren zur Herstellung von Copolymerisaten des FormaldehydsInfo
- Publication number
- DE1256896B DE1256896B DEP27337A DEP0027337A DE1256896B DE 1256896 B DE1256896 B DE 1256896B DE P27337 A DEP27337 A DE P27337A DE P0027337 A DEP0027337 A DE P0027337A DE 1256896 B DE1256896 B DE 1256896B
- Authority
- DE
- Germany
- Prior art keywords
- vinyl
- formaldehyde
- radical
- ether
- carbon atoms
- 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.)
- Pending
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 199
- 229920001577 copolymer Polymers 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 alkenyl radical Chemical class 0.000 claims description 31
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 9
- QYCVBOXNHNZFKO-UHFFFAOYSA-N ethylideneazanide Chemical class [CH2]C=[N] QYCVBOXNHNZFKO-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000000047 product Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 229960000834 vinyl ether Drugs 0.000 description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 13
- 229920001519 homopolymer Polymers 0.000 description 13
- 239000012429 reaction media Substances 0.000 description 13
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 11
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000012760 heat stabilizer Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- STYHKGTUMYFCLA-UHFFFAOYSA-N 1-ethenoxybut-1-ene Chemical class CCC=COC=C STYHKGTUMYFCLA-UHFFFAOYSA-N 0.000 description 3
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 3
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- SHIGCAOWAAOWIG-UHFFFAOYSA-N n-prop-2-enylformamide Chemical compound C=CCNC=O SHIGCAOWAAOWIG-UHFFFAOYSA-N 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- RCRRYCRTBURQSZ-UHFFFAOYSA-N 1-ethenoxy-4-methoxybutane Chemical compound COCCCCOC=C RCRRYCRTBURQSZ-UHFFFAOYSA-N 0.000 description 2
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 125000005670 ethenylalkyl group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- GFEKWEFJJHFPCD-UHFFFAOYSA-N 1-(2-ethenoxypropoxy)butane Chemical compound CCCCOCC(C)OC=C GFEKWEFJJHFPCD-UHFFFAOYSA-N 0.000 description 1
- ZDUPJYURNBOSAV-UHFFFAOYSA-N 1-(ethenoxymethoxy)butane Chemical compound CCCCOCOC=C ZDUPJYURNBOSAV-UHFFFAOYSA-N 0.000 description 1
- GHGLTMYUWRIKAD-UHFFFAOYSA-N 1-(ethenoxymethoxy)propane Chemical compound CCCOCOC=C GHGLTMYUWRIKAD-UHFFFAOYSA-N 0.000 description 1
- PNSAKLKMKPWBIC-UHFFFAOYSA-N 1-[2-(2-ethenoxyethoxy)ethoxy]-2-ethoxyethane Chemical compound CCOCCOCCOCCOC=C PNSAKLKMKPWBIC-UHFFFAOYSA-N 0.000 description 1
- KKARRJAMIBWONX-UHFFFAOYSA-N 1-butoxy-4-ethenoxybutane Chemical compound CCCCOCCCCOC=C KKARRJAMIBWONX-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- SHXWNOMJGVQIMH-UHFFFAOYSA-N 1-ethenoxy-5-methoxypentane Chemical compound COCCCCCOC=C SHXWNOMJGVQIMH-UHFFFAOYSA-N 0.000 description 1
- CNYZWOVHNQIMIM-UHFFFAOYSA-N 1-ethenoxy-6-ethoxyhexane Chemical compound CCOCCCCCCOC=C CNYZWOVHNQIMIM-UHFFFAOYSA-N 0.000 description 1
- OKMDPCZOIUBKBI-UHFFFAOYSA-N 1-ethenoxy-6-methoxyhexane Chemical compound COCCCCCCOC=C OKMDPCZOIUBKBI-UHFFFAOYSA-N 0.000 description 1
- PSPHUEMBSBTXKQ-UHFFFAOYSA-N 1-ethenoxybut-2-ene Chemical compound CC=CCOC=C PSPHUEMBSBTXKQ-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- GBUXVHGYEZDBMQ-UHFFFAOYSA-N 1-ethenoxyoct-1-ene Chemical class CCCCCCC=COC=C GBUXVHGYEZDBMQ-UHFFFAOYSA-N 0.000 description 1
- IOSXLUZXMXORMX-UHFFFAOYSA-N 1-ethenoxypentane Chemical compound CCCCCOC=C IOSXLUZXMXORMX-UHFFFAOYSA-N 0.000 description 1
- YKLWPGCWVBBCTO-UHFFFAOYSA-N 1-ethenoxyprop-1-ene Chemical compound CC=COC=C YKLWPGCWVBBCTO-UHFFFAOYSA-N 0.000 description 1
- SCGQVABHLGNHJZ-UHFFFAOYSA-N 1-ethenoxypropa-1,2-diene Chemical compound C=COC=C=C SCGQVABHLGNHJZ-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- RCSKFKICHQAKEZ-UHFFFAOYSA-N 1-ethenylindole Chemical compound C1=CC=C2N(C=C)C=CC2=C1 RCSKFKICHQAKEZ-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical compound C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
- QUMBYNOKZMNRAJ-UHFFFAOYSA-N 2-ethenoxy-1-methoxypropane Chemical compound COCC(C)OC=C QUMBYNOKZMNRAJ-UHFFFAOYSA-N 0.000 description 1
- OAASAJNCDIMPDW-UHFFFAOYSA-N 2-ethenyl-n-phenylaniline Chemical compound C=CC1=CC=CC=C1NC1=CC=CC=C1 OAASAJNCDIMPDW-UHFFFAOYSA-N 0.000 description 1
- PZNHAQALPSHGRA-UHFFFAOYSA-N 2-n-ethenylbenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC=C1C(=O)NC=C PZNHAQALPSHGRA-UHFFFAOYSA-N 0.000 description 1
- CEGOHIRBPWQSQD-UHFFFAOYSA-N 4-ethenoxybut-1-ene Chemical compound C=CCCOC=C CEGOHIRBPWQSQD-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- JQPJSNHVJHUGRD-UHFFFAOYSA-N C(=C)OCC(OCC(C)OC)C Chemical compound C(=C)OCC(OCC(C)OC)C JQPJSNHVJHUGRD-UHFFFAOYSA-N 0.000 description 1
- MBWIPSPDZIKCMQ-UHFFFAOYSA-N C(=C)OCCCCCCCOC Chemical compound C(=C)OCCCCCCCOC MBWIPSPDZIKCMQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BSADTNDLQSPKPA-UHFFFAOYSA-N N-cyclohexyl-N-ethenylacetamide Chemical compound C(C)(=O)N(C=C)C1CCCCC1 BSADTNDLQSPKPA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- QLCCBKRRTJZZOE-UHFFFAOYSA-N ethenoxycyclobutane Chemical compound C=COC1CCC1 QLCCBKRRTJZZOE-UHFFFAOYSA-N 0.000 description 1
- VGIYPVFBQRUBDD-UHFFFAOYSA-N ethenoxycyclohexane Chemical compound C=COC1CCCCC1 VGIYPVFBQRUBDD-UHFFFAOYSA-N 0.000 description 1
- HJVKTYVDOZVQPA-UHFFFAOYSA-N ethenoxycyclopentane Chemical compound C=COC1CCCC1 HJVKTYVDOZVQPA-UHFFFAOYSA-N 0.000 description 1
- XREZAPYWZGJIFS-UHFFFAOYSA-N ethenoxymethoxyethane Chemical compound CCOCOC=C XREZAPYWZGJIFS-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UVSNPDMUGCTOGJ-UHFFFAOYSA-N methoxymethoxyethene Chemical compound COCOC=C UVSNPDMUGCTOGJ-UHFFFAOYSA-N 0.000 description 1
- LQODOTZUMBVWPM-UHFFFAOYSA-N methyl 2-ethenoxyacetate Chemical compound COC(=O)COC=C LQODOTZUMBVWPM-UHFFFAOYSA-N 0.000 description 1
- QOKOTJJYPXKHJF-UHFFFAOYSA-N methyl 3-ethenoxypropanoate Chemical compound COC(=O)CCOC=C QOKOTJJYPXKHJF-UHFFFAOYSA-N 0.000 description 1
- AMKCHXUZZRBEQV-UHFFFAOYSA-N methyl 4-ethenoxybutanoate Chemical compound COC(=O)CCCOC=C AMKCHXUZZRBEQV-UHFFFAOYSA-N 0.000 description 1
- ZYINSGTUXKQIHW-UHFFFAOYSA-N methyl 5-ethenoxypentanoate Chemical compound COC(=O)CCCCOC=C ZYINSGTUXKQIHW-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XNUXFGBVDUGRCE-UHFFFAOYSA-N n-butyl-n-ethenylbutan-1-amine Chemical compound CCCCN(C=C)CCCC XNUXFGBVDUGRCE-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- CDXZRBLOGJXGTN-UHFFFAOYSA-N prop-2-enoxycyclohexane Chemical compound C=CCOC1CCCCC1 CDXZRBLOGJXGTN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C08G2/06—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
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/26—Copolymerisation of aldehydes or ketones with compounds containing carbon-to-carbon unsaturation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D159/00—Coating compositions based on polyacetals; Coating compositions based on derivatives of polyacetals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S74/00—Machine element or mechanism
- Y10S74/10—Polymer digest - plastic gears
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3542160A | 1960-06-13 | 1960-06-13 | |
| US35419A US3076786A (en) | 1960-06-13 | 1960-06-13 | Copolymers of formaldehyde and vinyl ethers |
| US35420A US3194790A (en) | 1960-06-13 | 1960-06-13 | Copolymers of formaldehyde and vinylnitrogen compounds |
| US5129460A | 1960-08-23 | 1960-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1256896B true DE1256896B (de) | 1967-12-21 |
Family
ID=27488299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP27337A Pending DE1256896B (de) | 1960-06-13 | 1961-06-13 | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds |
Country Status (5)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126410C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-06-13 | |||
| GB1002761A (en) * | 1960-10-17 | 1965-08-25 | British Industrial Plastics | Polymeric products from trioxan and aldehydes |
| NL271115A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-11-12 | |||
| NL271613A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-11-21 | |||
| DE1301542B (de) * | 1963-01-29 | 1969-08-21 | Ube Industries | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds |
| GB1050135A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-03-20 | |||
| US3408332A (en) * | 1963-04-26 | 1968-10-29 | Ethyl Corp | Formaldehyde and diene interpolymers |
| US3299005A (en) * | 1963-06-03 | 1967-01-17 | Diamond Alkali Co | Oxymethylene-epsilon caprolactam copolymers and method of preparation |
| US3367919A (en) * | 1963-06-24 | 1968-02-06 | Uniroyal Inc | Copolymers formed by reacting terephthalaldehyde with unsaturated monomer utilizing a friedel-crafts catalyst |
| DE1239098B (de) * | 1963-10-29 | 1967-04-20 | Ethyl Corp | Verfahren zur Herstellung von Homo- oder Copolymerisaten des Formaldehyds |
| US3336263A (en) * | 1964-03-02 | 1967-08-15 | Diamond Alkali Co | Process for preparing copolymers of formaldehyde and n, n'-methylenebisacrylamide and resulting product |
| DE1218154B (de) * | 1964-04-20 | 1966-06-02 | Bayer Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| NL124223C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-05-19 | |||
| DE1217067B (de) * | 1964-06-18 | 1966-05-18 | Bayer Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| DE1231009B (de) * | 1964-07-02 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| FR1415612A (fr) * | 1964-07-31 | 1965-10-29 | Pechiney Saint Gobain | Copolymères à base de formaldéhyde, leur procédé de préparation et leurs applications |
| FR1415611A (fr) * | 1964-07-31 | 1965-10-29 | Pechiney Saint Gobain | Procédé de préparation de copolymères à base de formaldéhyde, copolymères en résultant et leurs applications |
| DE1252898B (de) * | 1965-06-12 | 1967-10-26 | Bayer Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| US3380318A (en) * | 1965-08-10 | 1968-04-30 | Shakespeare Co | Cable assembly |
| FR2261296B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-02-14 | 1978-09-29 | Onera (Off Nat Aerospatiale) | |
| US4399272A (en) * | 1979-11-15 | 1983-08-16 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyacetal copolymers |
| JPS59115318A (ja) * | 1982-12-21 | 1984-07-03 | Ube Ind Ltd | ホルムアルデヒド共重合体の製法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB503623A (en) * | 1936-09-11 | 1939-04-12 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of artificial resins |
| GB583173A (en) * | 1942-07-04 | 1946-12-11 | Ici Ltd | Manufacture of polymers containing oxygen |
| FR1221148A (fr) * | 1958-02-28 | 1960-05-31 | Celanese Corp | Polymères d'oxyméthylène et d'oxyalkylène |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2312743A (en) * | 1939-12-01 | 1943-03-02 | Standard Oil Dev Co | Alkoxy meta-dioxanes |
| US2484423A (en) * | 1945-10-30 | 1949-10-11 | Eastman Kodak Co | Process for the preparation of polyvinylamine salts |
| US2653923A (en) * | 1948-11-13 | 1953-09-29 | Gen Aniline & Film Corp | Method for preparation of a polyvinyl methyl ether |
| US2543312A (en) * | 1948-11-13 | 1951-02-27 | Gen Aniline & Film Corp | Resinous acetals and process for producing and hydrolyzing the same to produce unsaturated aldehydes |
| US2526638A (en) * | 1949-03-03 | 1950-10-24 | Du Pont | Paper treated with formaldehyde and a polymeric polyamine |
| US3037963A (en) * | 1955-02-24 | 1962-06-05 | Pittsburgh Plate Glass Co | Resinous materials |
| US2936298A (en) * | 1957-10-21 | 1960-05-10 | Celanese Corp | Stabilized polymers |
| US3027352A (en) * | 1958-02-28 | 1962-03-27 | Celanese Corp | Copolymers |
| NL126410C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-06-13 |
-
0
- NL NL126410D patent/NL126410C/xx active
- NL NL285319D patent/NL285319A/xx unknown
-
1960
- 1960-06-13 US US35420A patent/US3194790A/en not_active Expired - Lifetime
- 1960-06-13 US US35419A patent/US3076786A/en not_active Expired - Lifetime
-
1961
- 1961-05-19 GB GB18341/61A patent/GB911960A/en not_active Expired
- 1961-06-13 DE DEP27337A patent/DE1256896B/de active Pending
- 1961-06-13 FR FR864807A patent/FR1302995A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB503623A (en) * | 1936-09-11 | 1939-04-12 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of artificial resins |
| GB583173A (en) * | 1942-07-04 | 1946-12-11 | Ici Ltd | Manufacture of polymers containing oxygen |
| FR1221148A (fr) * | 1958-02-28 | 1960-05-31 | Celanese Corp | Polymères d'oxyméthylène et d'oxyalkylène |
Also Published As
| Publication number | Publication date |
|---|---|
| US3194790A (en) | 1965-07-13 |
| US3076786A (en) | 1963-02-05 |
| FR1302995A (fr) | 1962-09-07 |
| NL126410C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| NL285319A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB911960A (en) | 1962-12-05 |
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