GB807196A - Polyarylenethylenes and their copolymers - Google Patents
Polyarylenethylenes and their copolymersInfo
- Publication number
- GB807196A GB807196A GB13072/56A GB1307256A GB807196A GB 807196 A GB807196 A GB 807196A GB 13072/56 A GB13072/56 A GB 13072/56A GB 1307256 A GB1307256 A GB 1307256A GB 807196 A GB807196 A GB 807196A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- trimethyl
- ammonium
- chloride
- poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 title abstract 2
- -1 hydrocarbon radical Chemical class 0.000 abstract 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 7
- 229920000642 polymer Polymers 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- 235000019270 ammonium chloride Nutrition 0.000 abstract 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 4
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229940107816 ammonium iodide Drugs 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 3
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 abstract 3
- UAQJEIWAMCLVTE-UHFFFAOYSA-N (3-methylthiophen-2-yl)methanol Chemical compound CC=1C=CSC=1CO UAQJEIWAMCLVTE-UHFFFAOYSA-N 0.000 abstract 2
- HVKXEXAOIBFLPI-UHFFFAOYSA-N 1-[5-[(4-chlorophenyl)methyl]thiophen-2-yl]-N,N-dimethylmethanamine Chemical compound ClC1=CC=C(CC2=CC=C(S2)CN(C)C)C=C1 HVKXEXAOIBFLPI-UHFFFAOYSA-N 0.000 abstract 2
- UTVXZWJURALNGC-UHFFFAOYSA-N 2,3-dimethylidenethiophene Chemical compound C=C1C=CSC1=C UTVXZWJURALNGC-UHFFFAOYSA-N 0.000 abstract 2
- ZTFYRZFWGRCCCK-UHFFFAOYSA-N 2,5-dimethylidenefuran Chemical compound C=C1C=CC(=C)O1 ZTFYRZFWGRCCCK-UHFFFAOYSA-N 0.000 abstract 2
- WHHHHDCPJAZHFA-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]thiophene Chemical compound C1=CC(Cl)=CC=C1CC1=CC=CS1 WHHHHDCPJAZHFA-UHFFFAOYSA-N 0.000 abstract 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 abstract 2
- PCVIGYOOZPUNSI-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]thiophene-2-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CC1=CC=C(C=O)S1 PCVIGYOOZPUNSI-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- BDDPNKBFSYKBPX-UHFFFAOYSA-M [Br-].BrC=1C=C(SC1C)[Mg+] Chemical compound [Br-].BrC=1C=C(SC1C)[Mg+] BDDPNKBFSYKBPX-UHFFFAOYSA-M 0.000 abstract 2
- GXUUUEFYENWEJQ-UHFFFAOYSA-M [Br-].C[N+](CC1=C(C=CC=C1)C)(C)C Chemical compound [Br-].C[N+](CC1=C(C=CC=C1)C)(C)C GXUUUEFYENWEJQ-UHFFFAOYSA-M 0.000 abstract 2
- QNJVZDSCGARGER-UHFFFAOYSA-M [Br-].C[N+](CC1=CC(=C(S1)C)Br)(C)C Chemical compound [Br-].C[N+](CC1=CC(=C(S1)C)Br)(C)C QNJVZDSCGARGER-UHFFFAOYSA-M 0.000 abstract 2
- QILNRLTXIOBNHQ-UHFFFAOYSA-M [Cl-].C[N+](C(C1=CC=CC=C1)CC1=CC=CC=C1)(C)C Chemical compound [Cl-].C[N+](C(C1=CC=CC=C1)CC1=CC=CC=C1)(C)C QILNRLTXIOBNHQ-UHFFFAOYSA-M 0.000 abstract 2
- IWEQICGKGUMCAH-UHFFFAOYSA-M [Cl-].C[N+](CC1=CC(=CC=C1C)I)(C)C Chemical compound [Cl-].C[N+](CC1=CC(=CC=C1C)I)(C)C IWEQICGKGUMCAH-UHFFFAOYSA-M 0.000 abstract 2
- CUXCNMQFIABXMX-UHFFFAOYSA-M [I-].C[N+](CC1=CC=C(S1)CC1=CC=C(C=C1)Cl)(C)C Chemical compound [I-].C[N+](CC1=CC=C(S1)CC1=CC=C(C=C1)Cl)(C)C CUXCNMQFIABXMX-UHFFFAOYSA-M 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 2
- 229960002903 benzyl benzoate Drugs 0.000 abstract 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- 229960004279 formaldehyde Drugs 0.000 abstract 2
- 235000019256 formaldehyde Nutrition 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 abstract 2
- ITURGVBDBUJAGD-UHFFFAOYSA-N n,n-dimethyl-1-(5-methylthiophen-2-yl)methanamine Chemical compound CN(C)CC1=CC=C(C)S1 ITURGVBDBUJAGD-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- QXLZGGOHVWNJAU-UHFFFAOYSA-M trimethyl-[(4-methylpyridin-2-yl)methyl]azanium chloride Chemical compound [Cl-].CC1=CC(=NC=C1)C[N+](C)(C)C QXLZGGOHVWNJAU-UHFFFAOYSA-M 0.000 abstract 2
- MPPJPOYFHKXSJO-UHFFFAOYSA-M trimethyl-[(5-methylthiophen-2-yl)methyl]azanium;iodide Chemical compound [I-].CC1=CC=C(C[N+](C)(C)C)S1 MPPJPOYFHKXSJO-UHFFFAOYSA-M 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- CEMOVHOFGZDHBR-UHFFFAOYSA-M (1,5-dimethylpyrrol-2-yl)-trimethylazanium chloride Chemical compound [Cl-].CN1C(=CC=C1C)[N+](C)(C)C CEMOVHOFGZDHBR-UHFFFAOYSA-M 0.000 abstract 1
- VXPAHRDPGPUJTP-UHFFFAOYSA-M (2,4-dimethylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CC1=CC=C(C[N+](C)(C)C)C(C)=C1 VXPAHRDPGPUJTP-UHFFFAOYSA-M 0.000 abstract 1
- AOPNDIFEGFXMJH-UHFFFAOYSA-K (3-chloro-4-methylphenyl)methyl-trimethylazanium phosphate Chemical compound P(=O)([O-])([O-])[O-].C[N+](CC1=CC(=C(C=C1)C)Cl)(C)C.C[N+](C)(C)CC1=CC(=C(C=C1)C)Cl.C[N+](C)(C)CC1=CC(=C(C=C1)C)Cl AOPNDIFEGFXMJH-UHFFFAOYSA-K 0.000 abstract 1
- ARRRJDFAZQCOHH-UHFFFAOYSA-M (3-chloro-4-methylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CC1=CC=C(C[N+](C)(C)C)C=C1Cl ARRRJDFAZQCOHH-UHFFFAOYSA-M 0.000 abstract 1
- ZEBBBIBTZSSMHF-UHFFFAOYSA-M (3-fluoro-4-methylphenyl)methyl-trimethylazanium chloride Chemical compound [Cl-].C[N+](CC1=CC(=C(C=C1)C)F)(C)C ZEBBBIBTZSSMHF-UHFFFAOYSA-M 0.000 abstract 1
- FLNNQSULPGHRHU-UHFFFAOYSA-M (3-fluoro-4-methylphenyl)methyl-trimethylazanium fluoride Chemical compound [F-].C[N+](CC1=CC(=C(C=C1)C)F)(C)C FLNNQSULPGHRHU-UHFFFAOYSA-M 0.000 abstract 1
- DVWNWBOKPLHBAP-UHFFFAOYSA-N (4-methylphenyl)methylazanium;chloride Chemical compound Cl.CC1=CC=C(CN)C=C1 DVWNWBOKPLHBAP-UHFFFAOYSA-N 0.000 abstract 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 abstract 1
- WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-UHFFFAOYSA-N 0.000 abstract 1
- PMNASCXFSVTLTC-UHFFFAOYSA-N 2-(chloromethyl)-3-methylthiophene Chemical compound CC=1C=CSC=1CCl PMNASCXFSVTLTC-UHFFFAOYSA-N 0.000 abstract 1
- LRABPQDNJCKSIR-UHFFFAOYSA-N 2-(chloromethyl)-4-iodo-1-methylbenzene Chemical compound IC=1C=C(CCl)C(=CC1)C LRABPQDNJCKSIR-UHFFFAOYSA-N 0.000 abstract 1
- DDGKEWIOOGLGAK-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyrazine Chemical compound CC1=CN=C(CCl)C=N1 DDGKEWIOOGLGAK-UHFFFAOYSA-N 0.000 abstract 1
- MXOPKPMEGUYUCV-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridine Chemical compound CC1=CC=C(CCl)N=C1 MXOPKPMEGUYUCV-UHFFFAOYSA-N 0.000 abstract 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 abstract 1
- WYOIVQNJGQPQLR-UHFFFAOYSA-N 2-benzylidene-5-methylidenefuran Chemical compound C(C1=CC=CC=C1)=C1OC(C=C1)=C WYOIVQNJGQPQLR-UHFFFAOYSA-N 0.000 abstract 1
- LROCVRUZMNKOTO-UHFFFAOYSA-N 2-phenylmethoxyethanethioamide Chemical compound NC(=S)COCC1=CC=CC=C1 LROCVRUZMNKOTO-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- DOFYUESISLMHPY-UHFFFAOYSA-N 3-bromo-2,5-dimethylidenethiophene Chemical compound BrC=1C(SC(C1)=C)=C DOFYUESISLMHPY-UHFFFAOYSA-N 0.000 abstract 1
- QPEGJWUCXATARO-UHFFFAOYSA-N 3-bromo-5-(bromomethyl)-2-methylthiophene Chemical compound BrC=1C=C(SC1C)CBr QPEGJWUCXATARO-UHFFFAOYSA-N 0.000 abstract 1
- BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- USNSCDIOWAJUKR-UHFFFAOYSA-N 4-(chloromethyl)-1-methyl-2-phenylbenzene Chemical compound CC1=CC=C(CCl)C=C1C1=CC=CC=C1 USNSCDIOWAJUKR-UHFFFAOYSA-N 0.000 abstract 1
- CDFRDDZQCBOCGF-UHFFFAOYSA-N 4-(chloromethyl)-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1F CDFRDDZQCBOCGF-UHFFFAOYSA-N 0.000 abstract 1
- MMMHSZNSSOEFAP-UHFFFAOYSA-N 5-(bromomethyl)-2-methylpyridine Chemical compound CC1=CC=C(CBr)C=N1 MMMHSZNSSOEFAP-UHFFFAOYSA-N 0.000 abstract 1
- VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 abstract 1
- JZVPBFSWJCRTEB-UHFFFAOYSA-N 9-(iodomethyl)-10-methylanthracene Chemical compound C1=CC=C2C(C)=C(C=CC=C3)C3=C(CI)C2=C1 JZVPBFSWJCRTEB-UHFFFAOYSA-N 0.000 abstract 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- YFMAWSAZCQEWQG-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].C[N+](CC1=CC(=C(C=C1)C)Cl)(C)C.C[N+](C)(C)CC1=CC(=C(C=C1)C)Cl Chemical compound S(=O)(=O)([O-])[O-].C[N+](CC1=CC(=C(C=C1)C)Cl)(C)C.C[N+](C)(C)CC1=CC(=C(C=C1)C)Cl YFMAWSAZCQEWQG-UHFFFAOYSA-L 0.000 abstract 1
- YMLXEGNDAXNLPY-UHFFFAOYSA-M [Br-].CC1=CC=C(N1C1=CC=CC=C1)C[N+](C)(C)C Chemical compound [Br-].CC1=CC=C(N1C1=CC=CC=C1)C[N+](C)(C)C YMLXEGNDAXNLPY-UHFFFAOYSA-M 0.000 abstract 1
- FTWJNDJQEHHISK-UHFFFAOYSA-M [Br-].CC1=NC=C(C=C1)C[N+](C)(C)C Chemical compound [Br-].CC1=NC=C(C=C1)C[N+](C)(C)C FTWJNDJQEHHISK-UHFFFAOYSA-M 0.000 abstract 1
- DKTNSRGBOVLTDP-UHFFFAOYSA-M [Br-].C[N+](CC1=C(C(=C(S1)C)Br)Br)(C)C Chemical compound [Br-].C[N+](CC1=C(C(=C(S1)C)Br)Br)(C)C DKTNSRGBOVLTDP-UHFFFAOYSA-M 0.000 abstract 1
- IGBSLGORFFHODX-UHFFFAOYSA-N [Cl-].CC1=C(C=C(C[NH3+])C=C1)C1=CC=CC=C1 Chemical compound [Cl-].CC1=C(C=C(C[NH3+])C=C1)C1=CC=CC=C1 IGBSLGORFFHODX-UHFFFAOYSA-N 0.000 abstract 1
- JFDKCDWWTOAVML-UHFFFAOYSA-M [Cl-].CC1=CC=C(N=N1)C[N+](C)(C)C Chemical compound [Cl-].CC1=CC=C(N=N1)C[N+](C)(C)C JFDKCDWWTOAVML-UHFFFAOYSA-M 0.000 abstract 1
- DCVLKALTYQKUQP-UHFFFAOYSA-M [Cl-].C[N+](CC1=C(C=CS1)C)(C)C Chemical compound [Cl-].C[N+](CC1=C(C=CS1)C)(C)C DCVLKALTYQKUQP-UHFFFAOYSA-M 0.000 abstract 1
- OBZLVJOIBLMCHC-UHFFFAOYSA-M [Cl-].C[N+](CC1=CC(=C(C=C1)C)C1=CC=CC=C1)(C)C Chemical compound [Cl-].C[N+](CC1=CC(=C(C=C1)C)C1=CC=CC=C1)(C)C OBZLVJOIBLMCHC-UHFFFAOYSA-M 0.000 abstract 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006298 dechlorination reaction Methods 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000002074 melt spinning Methods 0.000 abstract 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical group C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229940075930 picrate Drugs 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 1
- 229920000052 poly(p-xylylene) Polymers 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 abstract 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 1
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Inorganic materials [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- AZBDGHQMDZIFRS-UHFFFAOYSA-N tert-butyl-(5-methyl-1-phenylpyrrol-2-yl)azanium bromide Chemical compound [Br-].CC([NH2+]C=1N(C(=CC1)C)C1=CC=CC=C1)(C)C AZBDGHQMDZIFRS-UHFFFAOYSA-N 0.000 abstract 1
- TZGAGGCXQTZANF-UHFFFAOYSA-N tert-butyl-(6-methylpyridin-3-yl)azanium bromide Chemical compound [Br-].CC([NH2+]C=1C=CC(=NC1)C)(C)C TZGAGGCXQTZANF-UHFFFAOYSA-N 0.000 abstract 1
- IHLLJDQPJPQUDQ-UHFFFAOYSA-N tert-butyl-(8-methylquinolin-5-yl)azanium bromide Chemical compound [Br-].CC([NH2+]C1=C2C=CC=NC2=C(C=C1)C)(C)C IHLLJDQPJPQUDQ-UHFFFAOYSA-N 0.000 abstract 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- VGLIDTJHISILDF-UHFFFAOYSA-M trimethyl-[(10-methylanthracen-9-yl)methyl]azanium;iodide Chemical compound [I-].C1=CC=C2C(C)=C(C=CC=C3)C3=C(C[N+](C)(C)C)C2=C1 VGLIDTJHISILDF-UHFFFAOYSA-M 0.000 abstract 1
- FLYAUGRKDQYHOT-UHFFFAOYSA-M trimethyl-[(4-methylphenyl)methyl]azanium fluoride Chemical compound [F-].C[N+](CC1=CC=C(C=C1)C)(C)C FLYAUGRKDQYHOT-UHFFFAOYSA-M 0.000 abstract 1
- SLHXWNISKGRYSY-UHFFFAOYSA-M trimethyl-[(4-methylphenyl)methyl]azanium;bromide Chemical compound [Br-].CC1=CC=C(C[N+](C)(C)C)C=C1 SLHXWNISKGRYSY-UHFFFAOYSA-M 0.000 abstract 1
- BHZSLQZBUUWFED-UHFFFAOYSA-M trimethyl-[(4-methylphenyl)methyl]azanium;hydroxide Chemical compound [OH-].CC1=CC=C(C[N+](C)(C)C)C=C1 BHZSLQZBUUWFED-UHFFFAOYSA-M 0.000 abstract 1
- OZJHRTRJMVRCII-UHFFFAOYSA-M trimethyl-[(5-methylpyrazin-2-yl)methyl]azanium;chloride Chemical compound [Cl-].CC1=CN=C(C[N+](C)(C)C)C=N1 OZJHRTRJMVRCII-UHFFFAOYSA-M 0.000 abstract 1
- CWTUIBYTKOQDKP-UHFFFAOYSA-M trimethyl-[(5-methylthiophen-2-yl)methyl]azanium hydroxide Chemical compound [OH-].C[N+](CC1=CC=C(S1)C)(C)C CWTUIBYTKOQDKP-UHFFFAOYSA-M 0.000 abstract 1
- LZWMPOZTHGNQSX-UHFFFAOYSA-M trimethyl-[(8-methylquinolin-5-yl)methyl]azanium bromide Chemical compound [Br-].CC=1C=CC(=C2C=CC=NC12)C[N+](C)(C)C LZWMPOZTHGNQSX-UHFFFAOYSA-M 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/025—Polyxylylenes
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Polymers having the recurring units -CHR-Ar-CH2-, where R is hydrogen or a monovalent hydrocarbon radical and Ar is a bivalent aromatic unit wherein the two valences stem from the terminal carbon atoms of a chain of 2 or 4 ring atoms in an aromatic ring which may be substituted e.g. by halogen or lower alkyl radicals are made by heating to a temperature of at least 100 DEG C. in an aqueous alkali metal hydroxide solution maintained at at least 5 molal concentration one or more quaternary ammonium hydroxides or quaternary ammonium salts of strong inorganic acids in which the quaternary ammonium nitrogen is attached to three methyl groups and to a methylene radical whose remaining valency is satisfied by a carbon atom in an aromatic ring which aromatic ring has on a carbon atom thereof a hydrocarbon substituent, separated by a chain of 2 or 4 ring atoms from the methylene radical, and having at least two hydrogen atoms attached to the carbon atom of the hydrocarbon which is linked to the carbon atom of the aromatic ring. The quaternary ammonium compound containing the aromatic ring which may be carbocyclic or heterocyclic, may be trimethyl (p-methylbenzyl) ammonium bromide, chloride or hydroxide, trimethyl (o-methylbenzyl) ammonium bromide, trimethyl ( (3 - chloro - or 3 - fluoro - 4 - methylbenzyl) - ammonium chloride or fluoride, trimethyl (3-iodo-6-methylbenzyl) ammonium chloride, trimethyl (benzyl benzyl) ammonium chloride, trimethyl-(5 - methyl - 2 - furfuryl) ammonium iodide or hydroxide, trimethyl (5 - methyl - 2 - thenyl) ammonium iodide or hydroxide, trimethyl (5-p-chlorobenzyl-2-thenyl) ammonium iodide, trimethyl (4-bromo-5-methyl-2-thenyl) ammonium bromide, trimethyl (3,4-dibromo-5-methyl-2-thenyl) ammonium bromide, trimethyl (2,4-di methyl benzyl) ammonium chloride, trimethyl (4-methyl-3-phenyl) benzyl ammonium chloride trimethyl (alpha-duryl) ammonium chloride 10 - methyl - 9 - anthrylmethyltrimethyl ammonium iodide, 4,5 - dimethyl - 2 - thiazyltrimethyl ammonium chloride, (4 - methyl - 2-pyridylmethyl) trimethyl ammonium chloride, (1,5 - dimethyl - 2 - pyrrolyl) trimethyl ammonium chloride, trimethyl (2-methyl-5-pyridyl) methyl ammonium bromide, trimethyl (5- or 6-methyl- 2 or 3-pyridazinyl) methyl-ammonium chloride), trimethyl (8-methyl-5-quinolyl) methyl ammonium bromide, trimethyl (5-methyl-N - phenyl - 2 - pyrrolyl) methyl ammonium bromide and mixtures. Specified polymers are poly - p - xylylene, poly - 2 - chloro - p - xylylene, poly - 2,5 - dimethylenefuran, poly - 2,5-dimethylenethiophene, poly - 2 - p - chlorobenzlidene - 5 - methylenethiophene, poly - 3,4 - dibromo - 2,5 - dimethylenethiophene, poly - 2,3-dimethylenethiophene, poly - o - methyl - p-xylylene, poly - 2,5 - dimethyl - p - xylylene, poly - 9,10 - dimethyleneanthracene, poly - 4-methyl - 2,5 - dimethylenethiazole, poly - 2,5-dimethylene pyridine, poly - 2,5 - dimethylene-N - methyl - pyrrole, poly - 2,5 - dimethylene-pyridine, poly - 2,5 - dimethylenepyrazine, poly - 3,6 - dimethylenepyridazine, poly - 2,5-dimethylenepyrimidine, poly - 5,8 - dimethylenequinoline, poly - 5,8 - dimethyleneisoquinoline, poly - 2,5 - dimethylene - N - phenylpyrrole, and copolymers of p-xylylene/o-xylylene, alphaphenyl - o - xylylene/alpha - phenyl-p - xylylene, alpha - phenyl - o - xylylene/alpha-phenyl - p - xylylene/2,5 - dimethylenefuran, p-xylylene/2,5 - dimethyl - p - xylylene, 3 - bromo-2,5 - dimethylenethiophene/2,3 - dimethylenethiophene, 2 - benzylidene - 5 - methylenefuran/2,3 - dimethylenethiophene, 2,5 - dimethylene-furan/alpha - phenyl - o - xylylene, and 2-chloro - p - xylylene/o - xylylene. The alkali metal hydroxide may be sodium, potassium, lithium, rubidium, or cesium hydroxide. The process is preferably effected in a system containing an aqueous phase and a liquid non-aqueous phase such as toluene, p-fluorotoluene, xylene, ethylbenzene, cumene, mesitylene, chlorobenzene, bromobenzene, iodobenzene, or tetrahydronaphthalene. The polymer formation may be effected in the presence of a free radical initiator such as alpha, alpha1-azobisisobutyramidine hydrochloride or alpha, alpha1-azodicyclohexane-carbonitrile. The polymers may be made into fibres, e.g. by melt spinning, and the fibres sintered and/or drawn at elevated temperatures. The p-xylylene homopolymer is said to have a specific unimolecular thermal degradation constant k of less than 2.0 X 10-5 min.-1 when determined at 305 DEG C. in a solution in benzyl benzoate at a concentration of 0.39 gm. of polymer in 100 ml. of benzyl benzoate, where <FORM:0807196/IV (a)/1> where t is the heating time in minutes at 305 DEG C., Mm is the molecular weight of the p-xylylene unit, i.e. 104.14, and M is the molecular weight of the polymer determined from the inherent viscosity of the solution at a time t as given by the equation <FORM:0807196/IV (a)/2> and Mo is, at time zero, the molecular weight of the polymer. Specifications 650,947 and 673,651 are referred to.ALSO:Trimethyl (para-methylbenzyl) ammonium chloride, trimethyl (ortho-methylbenzyl) ammonium bromide, trimethyl (3-chloro-4-methylbenzyl) ammonium chloride, trimethyl (3-fluoro-4-methylbenzyl) ammonium chloride, trimethyl (3-iodo-6-methylbenzyl) ammonium chloride, trimethyl (benzylbenzyl) ammonium chloride, trimethyl (4-bromo - 5 - methyl - 2 - thenyl) ammonium bromide, trimethyl (3: 4-dibromo-5-methyl-3-thenyl) ammonium bromide, trimethyl (3-methyl-2-thenyl) ammonium chloride, trimethyl (2 : 4-dimethylbenzyl) ammonium chloride, trimethyl (4-methyl-3-phenylbenzyl) ammonium chloride, trimethyl (a -duryl) ammonium chloride, (10-methyl-9-anthrylmethyl) trimethyl ammonium iodide, (4 : 5-dimethyl - 2 - thiazylmethyl) trimethylammonium chloride, (4 - methyl - 2 - pyridylmethyl) trimethylammonium chloride, (1 : 5-dimethyl-2-pyrrolylmethyl) trimethylammonium chloride, (2-methyl-5-pyridylmethyl) trimethylammonium bromide, (5-methyl - 2 - pyrazinylmethyl) trimethylammonium chloride, (6-methyl-3-pyridazinylmethyl) trimethyl ammonium chloride, (8-methyl-5-quinolylmethyl) trimethyl ammonium bromide and (5-methyl-N-phenyl-2-pyrrolylmethyl) trimethylammonium bromide are prepared by quaternating trimethylamine. Trimethyl (para-methylbenzyl) ammonium hydroxide, trimethyl (3-fluoro-4-methylbenzyl) ammonium fluoride, trimethyl (5-methyl-2-furfuryl) ammonium hydroxide, trimethyl (5-methyl-2-thenyl) ammonium hydroxide, trimethyl (paramethylbenzyl) ammonium fluoride, trimethyl (3-chloro - 4 - methylbenzyl) ammonium sulphate and trimethyl (3-chloro-4-methylbenzyl) ammonium phosphate are prepared by anion exchange. 3 - Fluoro - 4 - methylbenzyl chloride, 3 - iodo-6-methylbenzyl chloride, 2 : 4-dimethylbenzyl chloride, 4-methyl-3-phenylbenzyl chloride and 10-methyl - 9 - iodomethylanthracene are prepared by appropriate halomethylation. 5 - Ethyl - 2 - furfuryldimethylamine and 5-benzyl - 2 - furfuryl dimethylamine are prepared by treating a -ethylfuran and furylphenylmethane respectively with a mixture of form-aldehyde and methylamine hydrochloride. 5 - Methyl - 2 - thenyldimethylamine and 5-parachlorobenzyl - 2 - thenyldimethylamine are prepared by treating 5-methyl-2-thiophene carboxaldehyde and 5 - para - chlorobenzyl - 2-thiophene carboxaldehyde respectively with a mixture of dimethylamine and formic acid according to the process described in J. Am. Chem. Soc. 75, 3033 (1953). Trimethyl (5 - ethyl - 2 - furfuryl) ammonium iodide, trimethyl (5 - methyl - 2 - thenyl) ammonium iodide, trimethyl (5 - para - chlorobenzyl-2-thenyl) ammonium iodide and trimethyl (5-benzyl - 2 - furfuryl) ammonium iodide are prepared by quaternating 5-ethyl-2-furfuryldimethylamine, 5 - methyl - 2 - thenyldimethylamine, 5 - para - chlorobenzyl - 2 - thenyldimethylamine and 5-benzyl-2-furfuryldimethylamine respectively. 2 - (Para - chlorobenzyl) thiophene is prepared by heating para-chlorobenzyl chloride with thiophene in presence of zinc chloride. 5 - Para - chlorobenzyl - 2 - thiophenecarboxaldehyde is prepared by reacting 2-(para-chlorobenzyl) thiophene with N : N-dimethylformamide and phosphorus oxychloride. 4 - Bromo - 5 - methyl - 2 - thienylmagnesium bromide and 3 : 4 - dibromo - 5 - methyl - 2-thienyl-magnesium bromide are prepared by treating 2 : 4-dibromo-5-methylthiophene and 2 : 3 : 4 - tribromo - 5 - methylthiophene respectively with magnesium and methyl bromide in ether. 4 - Bromo - 5 - methyl - 2 - thenyl alcohol and 3 : 4 - dibromo - 5 - methyl - 2 - thenyl alcohol are prepared by treating 4-bromo-5-methyl-2-thienylmagnesium bromide and 3 : 4-dibromo-5-methyl-2-thienylmagnesium bromide respectively with formaldehyde. 3-Methyl-2-hydroxymethylthiophene is prepared by sodium borohydride reduction of 3 - methyl - 2 - thenaldehyde. 2-Hydroxymethyl-4 : 5-dimethylthiazole is prepared by heating a mixture of benzyloxythioacetamide and a -bromoethyl methyl ketone with pyridine and ethanol, followed by further heating with aqueous NaOH. The picrate is described. 2 : 5 - Dimethyl - 4 : 6 - dihydroxypyrimidine is prepared by condensing diethyl a -methylmalonate with acetamidine. 4 - Bromo - 5 - methyl - 2 - thenyl bromide, 3 : 4 - dibromo - 5 - methyl - 2 - thenyl bromide, 3 - methyl - 2 - thenyl chloride and 4 : 5 - dimethyl-2-chloromethylthiazole are prepared by reacting 4-bromo-5-methyl-2-thenyl alcohol, 3 : 4 - dibromo - 5 - methyl - 2 - thenyl alcohol, 3 - methyl - 2 - hydroxymethylthiophene and 1-hydroxymethyl-4 : 5-dimethylthiazole respectively with hydrobromic acid or thionyl chloride. 2 : 5 - Dimethyl - 4 : 6 - dichloropyrimidine is prepared by treating 2 : 5-dimethyl-4 : 6-dihydroxypyrimidine with phosphorus pentachloride. 2 : 5 - Dimethylpyrimidine is prepared by dechlorination of 2 : 5 - dimethyl - 4 : 6 - dichloropyrimidine in presence of nickel. 2 - Chloromethyl - 5 - methylpyridine, 2-methyl - 5 - bromomethylpyridine, 2 - methyl - 5-chloromethylpyrazine, 3 - methyl - 6 - ch
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US807196XA | 1955-05-02 | 1955-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB807196A true GB807196A (en) | 1959-01-07 |
Family
ID=22159172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13072/56A Expired GB807196A (en) | 1955-05-02 | 1956-04-27 | Polyarylenethylenes and their copolymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB807196A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361726A (en) * | 1963-09-30 | 1968-01-02 | Du Pont | Process for preparing poly(9, 10-dimethyleneanthracene) |
| EP0220743A1 (en) * | 1985-10-30 | 1987-05-06 | Montedison S.p.A. | Process for the preparation of (2,2)-paracyclophane |
| EP0220744A1 (en) * | 1985-10-30 | 1987-05-06 | Montedison S.p.A. | Process for the preparation of halogenated (2,2)-paracyclophanes |
| EP0291889A1 (en) * | 1987-05-15 | 1988-11-23 | Union Carbide Corporation | Process for the preparation of dichloro-[2,2] paracyclophane |
| US4795838A (en) * | 1986-06-27 | 1989-01-03 | Montedison S.P.A. | Process for the preparation of (2,2)-paracyclophane and derivatives thereof |
| US4816608A (en) * | 1986-06-27 | 1989-03-28 | Montedison S.P.A. | Process for the preparation of (2,2)-paracyclophane and derivatives thereof |
| EP0436957A1 (en) * | 1989-12-29 | 1991-07-17 | Daisan Kasei Kabushiki Kaisha | Process for the preparation of dichloro-(2,2)-paracyclophane |
| US5310858A (en) * | 1992-01-31 | 1994-05-10 | Hoechst Aktiengesellschaft | Process for preparing polymers of p-xylylene from p-xylylene diesters |
| JPH0747553B2 (en) | 1989-12-29 | 1995-05-24 | 第三化成株式会社 | Process for producing dichloro- (2,2) -paracyclophane |
-
1956
- 1956-04-27 GB GB13072/56A patent/GB807196A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361726A (en) * | 1963-09-30 | 1968-01-02 | Du Pont | Process for preparing poly(9, 10-dimethyleneanthracene) |
| EP0220743A1 (en) * | 1985-10-30 | 1987-05-06 | Montedison S.p.A. | Process for the preparation of (2,2)-paracyclophane |
| EP0220744A1 (en) * | 1985-10-30 | 1987-05-06 | Montedison S.p.A. | Process for the preparation of halogenated (2,2)-paracyclophanes |
| US4783561A (en) * | 1985-10-30 | 1988-11-08 | Montedison S.P.A. | Process for the preparation of halogenated (2,2)-paracyclophanes and mixtures of resultant halogenated (2,2)-paracyclophanes |
| US4816608A (en) * | 1986-06-27 | 1989-03-28 | Montedison S.P.A. | Process for the preparation of (2,2)-paracyclophane and derivatives thereof |
| US4795838A (en) * | 1986-06-27 | 1989-01-03 | Montedison S.P.A. | Process for the preparation of (2,2)-paracyclophane and derivatives thereof |
| JPS6445322A (en) * | 1987-05-15 | 1989-02-17 | Union Carbide Corp | Manufacture of dichloro-(2,2)paracyclophane |
| EP0291889A1 (en) * | 1987-05-15 | 1988-11-23 | Union Carbide Corporation | Process for the preparation of dichloro-[2,2] paracyclophane |
| US4849559A (en) * | 1987-05-15 | 1989-07-18 | Union Carbide Corporation | Process for the preparation of dichloro-[2,2]paracyclophane |
| JPH0669973B2 (en) | 1987-05-15 | 1994-09-07 | ユニオン・カーバイド・コーポレーション | Process for producing dichloro- [2,2] paracyclophane |
| EP0436957A1 (en) * | 1989-12-29 | 1991-07-17 | Daisan Kasei Kabushiki Kaisha | Process for the preparation of dichloro-(2,2)-paracyclophane |
| JPH0747553B2 (en) | 1989-12-29 | 1995-05-24 | 第三化成株式会社 | Process for producing dichloro- (2,2) -paracyclophane |
| US5310858A (en) * | 1992-01-31 | 1994-05-10 | Hoechst Aktiengesellschaft | Process for preparing polymers of p-xylylene from p-xylylene diesters |
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