NO159284B - Katalysator til polymerisering av alfa-alkener og anvendelse av katalysatoren. - Google Patents
Katalysator til polymerisering av alfa-alkener og anvendelse av katalysatoren. Download PDFInfo
- Publication number
- NO159284B NO159284B NO820660A NO820660A NO159284B NO 159284 B NO159284 B NO 159284B NO 820660 A NO820660 A NO 820660A NO 820660 A NO820660 A NO 820660A NO 159284 B NO159284 B NO 159284B
- Authority
- NO
- Norway
- Prior art keywords
- polymerization
- weight
- parts
- compounds
- catalyst
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title abstract description 9
- 238000006116 polymerization reaction Methods 0.000 title abstract description 9
- 150000001336 alkenes Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 9
- 229920006305 unsaturated polyester Polymers 0.000 claims description 11
- 239000002685 polymerization catalyst Substances 0.000 claims description 10
- 239000003349 gelling agent Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 230000000737 periodic effect Effects 0.000 abstract description 2
- 150000003623 transition metal compounds Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000003825 pressing Methods 0.000 description 10
- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000428199 Mustelinae Species 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- -1 high flammability Chemical class 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- JWLJITRPNAZVRK-UHFFFAOYSA-N (1,2-dichloro-1,2,2-triphenylethyl)benzene Chemical compound C=1C=CC=CC=1C(C(Cl)(C=1C=CC=CC=1)C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JWLJITRPNAZVRK-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 239000010459 dolomite Substances 0.000 description 2
- 229910000514 dolomite Inorganic materials 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SWNTUXVFZXJRMT-UHFFFAOYSA-N 1,2-diphenyl-1,2-dipyridin-3-ylethane-1,2-diol Chemical compound C=1C=CN=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=NC=CC=1)(O)C1=CC=CC=C1 SWNTUXVFZXJRMT-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- ZZYASVWWDLJXIM-UHFFFAOYSA-N 2,5-di-tert-Butyl-1,4-benzoquinone Chemical compound CC(C)(C)C1=CC(=O)C(C(C)(C)C)=CC1=O ZZYASVWWDLJXIM-UHFFFAOYSA-N 0.000 description 1
- XISFOXBYRQWDNK-UHFFFAOYSA-N 2-(2-methylphenyl)propan-2-amine;hydrochloride Chemical compound [Cl-].CC1=CC=CC=C1C(C)(C)[NH3+] XISFOXBYRQWDNK-UHFFFAOYSA-N 0.000 description 1
- ZQNFUXDRYQQYAQ-UHFFFAOYSA-N 2-amino-1,1,2-triphenylethanol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC=CC=1)C(N)C1=CC=CC=C1 ZQNFUXDRYQQYAQ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/02—Carriers therefor
- C08F4/022—Magnesium halide as support anhydrous or hydrated or complexed by means of a Lewis base for Ziegler-type catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Description
Fremgangsmåte ved trinnvis fremstilling av formlegemer ut fra pressmasser på
basis av umettet polyester og sampolymeriserbare monomere forbindelser.
Det er kjent å herde blandinger av
umettede polyestere og sampolymeriserbare monomere forbindelser, i det følg-ende kalt polyesterpressmasser, til formlegemer. Det er videre kjent først å over-føre sådanne polyesterpressmasser ved
delvis polymerisasjon til forpolymerisater
og derefter å herde disse forpolymerisater
til formlegemer i ett eller flere ytterligere
polymerisasjonstrinn. Som utgangsmate-rialer for fremstilling av formlegemer byr
sådanne forpolymerisater ofte på betyde-lige fordeler sammenlignet med de ikke
forpolymeriserte pressmasser. For eksempel som faste eller halvfaste masser byr de
på mangfoldige forarbeidelsesmuligheter.
Ved deres anvendelse unngås dessuten i
stor utstrekning polymerisasjonsskrump-ning.
Som kjent lar umettede polyesterpressmasser seg utherde under innsjaltning av
en forpolymerisasjon, altså trinnvis, ved at
der foruten peroxydiske polymerisasjonskatalysatorer, som skal frembringe den
endelige herdning først ved sterkt forhøyet
temperatur, tilsettes såkalte geleringsmidler. Det dreier seg her om stoffer som
bringer pressmassene til å gelere ved romtemperatur eller moderat forhøyede temperaturer. Ulempene ved en slik fremgangsmåte ligger deri at de peroxydiske
katalysatorer i seg selv, leilighetsvis også
ved vekselvirkning med geleringsmidlet,
bare har begrenset stabilitet allerede ved
romtemperatur eller moderat forhøyet
temperatur og derfor setter et spørsmåls-
tegn ved regulert fremstilling av forpolymerisatene og også ved deres lagringssta-bilitet.
Den foreliggende oppfinnelse angår en fremgangsmåte ved trinnvis fremstilling av formlegemer ut fra pressmasser på basis av umettet polyester og sampolymeriserbare monomere forbindelser med et innhold av polymerisasjonskatalysatorer og geleringsmidler og eventuelt fyllstoffer.
Det karakteristiske ved oppfinnelsen er den kombinasjon av trekk at det som polymerisasjonskatalysatorer anvendes 1,2-substituerte ethanderivater med den generelle formel:
i hvilken Rx og R3 betegner aromatiske radikaler, R2 betegner hydrogen eller et alifatisk eller aromatisk radikal, R4 betegner et alifatisk eller aromatisk radikal og X og Y betegner en eventuelt blokkert hydroxylgruppe og/eller en eventuelt substituert NH2-gruppe og/eller halogen, og at utgangsblandingen i første trinn oppvarmes til en temperatur ved hvilken det anvendte geleringsmiddel er virksomt, men polymerisasjonskatalysatoren er uvirksom, hvoretter blandingen i det senere sluttherd-ningstrinn oppvarmes til en så høy temperatur at polymerisasjonskatalysatoren trer i virksomhet.
De nevnte katalysatorer er å foretrek-ke fremfor de hittil vanligvis anvendte peroxyder på grunn av deres fremragende stabilitet ved romtemperatur og moderat forhøyet temperatur — også i nærvær av geleringsmidler — som letter reguleringen av geleringen og muliggjør fremstilling av forpolymerisater med særlig høy lagrings-stabilitet. Videre er det en fordel at disse katalysatorer ikke er beheftet med de kjente mangler ved peroxydene, nemlig stor brennbarhet, tendens til å eksplodere og allergisk irritasjonsvirkning.
Typiske representanter for disse ethanderivater er benzpinakon og dets kjerne-substitusjonsprodukter. Blant andre forbindelser som tilhører denne klasse, kan nevnes:: benzpinakonmono- og di-alkyl-ether, benzpinakonmono- og di-fenylether, det cykliske carbonat av benzpinakon og benzpinakondibenzoat, dessuten acetofe-nonpinakon og dets cykliske sulfitt, xan-thonpinakon og fluorenonpinakon, dessuten l,2-di-(3-pyridyl)-l,2-difenyl-ethan-l,2-diol, 1,2-diklortetrafenylethan, trifenyl-glycol og trifenylethanolamin.
Katalysatorene anvendes fortrinnsvis i mengder av omtrent 0,1—10 pst. beregnet på pressmassen.
Som eksempler på geleringsmidler som på i og for seg kjent vis bevirker forpoly-merisering av umettede poplyesterpress-masser til geltrinnet, kan nevnes bortri-fluorid, svovelsyre, fosforpentoxyd, haloge-nider av elementer i gruppene 3—5 i det periodiske system, f. eks. tinn-II-klorid, eventuelt i blanding av mercaptaner, videre alkylmetall og Grignard-forbindelser, dessuten blandinger av aminsalter og mercaptaner, f. eks. trimethylbenzylaminhyd-roklorid og dodecylmercaptan, og endelig også sterke reduksjonsmidler, såsom f. eks. ascorbinsyre.
Umettede polyestere som kan anvendes ved fremgangsmåten ifølge oppfinnelsen, er de vanlig anvendte kondensasjons-produkter av a,|3-ethylenisk umettede dicarboxylsyrer, såsom maleinsyre, fumar-syre, mesaconsyre og citraconsyre, med polyalkoholer såsom ethylenglycol, diethy-lenglycol, propan-, butan- og hexandioler, trimethylolpropan og pentaerythrit, som eventuelt også kan inneholde radikaler av andre dicarboxylsyrer, f. eks. fthalsyre, tetraklorfthalsyre, terefthalsyre, adipinsy-re og lignende, dessuten monofunksjonelle alkoho<l>er, såsom butanol, tetrahydrofur-furylalkohol og ethylenglycolmonobutyl-ether, såvel som énbasiske syrer, såsom benzoesyre, oljesyre, linoljefettsyre og ri-cinenfettsyre.
Egnede monomere umettede forbindelser som kan sampolymeriseres med de umettede polyestere, er f. eks. vinylfor-bindelser såsom styren, vinyltoluen og di-vinylbenzen, videre vinylestere såsom vi-nylacetat, dessuten umettede carboxylsy-rer og deres derivater, såsom (meth)-acrylsyreester og -nitril, og dessuten allyl-estere, såsom allylacetat, allylacrylat, fthalsyrediallylester, triallylfosfat og tri-allylcyanurat.
Nevnes skal også blandinger av umettede polyestere med monomere umettede forbindelser, som foruten de a,p-umettede dicarboxylsyreradiakaler som bestanddeler av polyesteren også inneholder p.y-umettede etherrester, enten som bestanddel av polyestere såsom ifølge tysk utlegnings-skrift 1 024 654, eller som bestanddel av andre blandingskomponenter, såsom ifølge tysk patent nr. 1 067 210 og tysk patent nr. 1 081 222, som ved siden av at de er sampolymeriserbare også er lufttørkende.
Eventuelt kan der som inhibitorer tilsettes kjente tilsetningsmidler såsom f. eks. p-benzokinon, 2,5-di-tert.-butylkinon, hydrokinon, tert.butylbrenzkatekin og 4-ethyl-brenzkatekin og videre kobberfor-bindelser og hydroxylaminderivater.
Ved siden av katalysatorer, geleringsmidler og eventuelt inhibitorer kan de umettede polyesterpressmasser også inneholde i faget kjente tilsetningsmidler som f. eks. magnesiumoxyd, kritt, skifermel, tungspat, talkum, farvestoffer, vevede strukturer eller fibre av glass, plast- eller tekstilprodukter, forbindelser som gir be-skyttelse mot lys, varme eller forbrenning, osv. Det er fordelaktig å tilsette disse stoffer før eller under forpolymeriseringen.
Forpolymeriseringen utføres hensikts-messig i blandeapparater, knaere, snekker eller valseapparatur ved romtemperatur eller moderat forhøyet temperatur. For å oppnå gode resultater ved fremgangsmåten er det nødvendig at forpolymeriseringen til geltrinnet finner sted i et tempe-raturområde i hvilket de tilblandede polymerisasjonskatalysatorer ikke ansporer den endelige utherdning. Hensiktsmessige temperaturer kan bestemmes ved hjelp av enkle innledende forsøk. Overgangen til geltilstanden gir seg tilkjenne — også for sterkt fylte massers vedkommende — ved en karakteristisk, lett kjennelig konsistens-endring.
Forpolymerisatene kan, eksempelvis som dryssbare pressmasser, også efter lang lagringstid utherdes varmt under form-givning på vanlig måte.
Ytterligere enkelheter vil fremgå av de efterfølgende eksempler.
Eksempel 1.
En umettet polyester fremstilt ved kondensasjon av 1720 vektdeler maleinsy-reanhydrid, 660 vektdeler fthalsyreanhyd-rid, 590 vektdeler glycol og 1188 vektdeler butandiol-1,3, oppløses i 65 pst.ig styren.
600 vektdeler av den således erholdte pressmasse forarbeides sammen med 1800 vektdeler dolomit, 24 vektdeler sinkstea-rat, 12 vektdeler magnesiumoxyd, 12 vektdeler benzpinakon, 4,2 vektdeler av en 25 pstig sink-II-klorid-oppløsning i dimethylformamid og 2,4 vektdeler dodecylmercaptan i en til 40° C oppvarmet knaer under nitrogenatomosfære. Ef ter omtrent 40 minutter inntrer gelering, hvorved den opprinnelige tyktflytende masse festner. Ef ter avkjøling til romtemperatur bringes det erholdte forpolymerisat på en korn-størrelse på 3—4 mm 0.
280 deler av den således erholdte dryssbare masse presses i et standardverk-tøy (DIN 53,470 for fremstilling av standardstaver) ved 145° C og 30 t trykk i 4 minutter. Standardstavene har følgende egenskaper: Martensgrad: 120° Bøyefasthet: 300 kp/cm<2>
Slagbøyefasthet: 1,8 cm.kp/cm<2>
Gjentatt presning efter 5 måneders lagring av pressmassen ga likeverdige resultater.
Eksempel 2.
1000 vektdeler av pressmassen fra eksempel 1 knaes ved 60° C inntil gelering er inntrått, sammen med 2000 vektdeler dolomit, 300 vektdeler glassull, 40 deler sink-stearat, 20 vektdeler magnesiumoxyd, 20 vektdeler benzpinakon og 1 vektdel ascorbinsyre (oppløst i dimethylformamid i for-holdet 1 : 3),hvoretter det erholdte produkt avkjøles og males til ønsket kornstørrelse.
Standardstaver fremstilt ved 4 minut-ters presning av det forpolymeriserte mate-riale (145° C, 30 t) i standardverktøyet har følgende egenskaper: Martensgrad: 136° C Bøyefasthet: 500 kp/cm<2>
Slagbøyefasthet: 6,0 cm.kp/cm<2>
Også her oppnåes der efter gjentatt presning efter 5 måneders lagring av for-polymerisatet et likeverdig resultat.
Eksempel 3.
Man går frem som i eksempel 2, bort-sett fra at man i stedet for 20 vektdeler benzpinakon anvender 20 vektdeler aceto-fenonpinakon.
De erholdte standardstaver har følg-ende egenskaper: Martensgrad: 124° C Bøyefasthet: 480 kp/cm<2>
Slagbøyefasthet: 6,4 cm.kp/cm<2>
Eksempel 4.
Man går frem som i eksempel 2, bort-sett fra at man i stedet for 20 vektdeler benzpinakon anvender 20 vektdeler 1,2-diklor-tetrafenylethan.
De erholdte standardstaver har følg-ende egenskaper: Martensgrad: 126° C Bøyefasthet: 480 kp/cm<2>
Slagbøyefasthet: 5,9 cm.kp/cm<2>
Eksempel 5.
Man går frem som i eksempel 2, bort-sett fra at man i stedet for 20 vektdeler benzpinakon anvender 20 vektdeler benz-pinakondimethylether.
De erholdte standardstaver har følg-ende egenskaper: Martensgrad: 140° C Bøyefasthet: 490 kp/cm<2>
Slagbøyefasthet: 6,0 cm.kp/cm<2>
Claims (1)
- Fremgangsmåte ved trinnvis fremstilling av formlegemer ut fra pressmasser på basis av umettet polyester og sampolymeriserbare monomere forbindelser med et innhold av polymerisasjonskatalysatorer og geleringsmidler og eventuelt fyllstoffer, karakterisert ved den kombinasjon av trekk at det som polymerisasjonskatalysatorer anvendes 1,2-substituerte ethanderivater med den generelle formel:i hvilken Rx og R3 betegner aromatiske radikaler, R2 betegner hydrogen eller et alifatisk eller aromatisk radikal, R4 beteg- ner et alifatisk eller aromatisk radikal og X og Y betegner en eventuelt blokkert hydroxylgruppe og/eller en eventuelt substituert NH2-gruppe og/eller halogen, og at utgangsblandingen i første trinn oppvarmes til en temperatur ved hvilken det an- vendte geleringsmiddel er virksomt men polymerisasjonskatalysatoren er uvirksom, hvorefter blandingen i det senere slutt-herdingstrinn oppvarmes til en så høy temperatur at polymerisasjonskatalysatoren trer i virksomhet.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/240,533 US4394291A (en) | 1981-03-04 | 1981-03-04 | Polyolefin polymerization process and catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO820660L NO820660L (no) | 1982-09-06 |
| NO159284B true NO159284B (no) | 1988-09-05 |
| NO159284C NO159284C (no) | 1988-12-14 |
Family
ID=22906926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO820660A NO159284C (no) | 1981-03-04 | 1982-03-03 | Katalysator til polymerisering av alfa-alkener og anvendelse av katalysatoren. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4394291A (no) |
| EP (1) | EP0060443B1 (no) |
| JP (1) | JPS57158207A (no) |
| AT (1) | ATE48145T1 (no) |
| BR (1) | BR8201027A (no) |
| CA (1) | CA1183119A (no) |
| DE (1) | DE3280033D1 (no) |
| ES (1) | ES8306768A1 (no) |
| GB (1) | GB2093851B (no) |
| MX (1) | MX159971A (no) |
| NO (1) | NO159284C (no) |
| SG (1) | SG16385G (no) |
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-
1981
- 1981-03-04 US US06/240,533 patent/US4394291A/en not_active Expired - Lifetime
-
1982
- 1982-02-08 CA CA000395763A patent/CA1183119A/en not_active Expired
- 1982-02-24 MX MX191553A patent/MX159971A/es unknown
- 1982-02-26 JP JP57030472A patent/JPS57158207A/ja active Granted
- 1982-02-26 BR BR8201027A patent/BR8201027A/pt not_active IP Right Cessation
- 1982-03-03 EP EP82101638A patent/EP0060443B1/en not_active Expired
- 1982-03-03 AT AT82101638T patent/ATE48145T1/de not_active IP Right Cessation
- 1982-03-03 NO NO820660A patent/NO159284C/no unknown
- 1982-03-03 DE DE8282101638T patent/DE3280033D1/de not_active Expired
- 1982-03-04 GB GB8206320A patent/GB2093851B/en not_active Expired
- 1982-03-04 ES ES510130A patent/ES8306768A1/es not_active Expired
-
1985
- 1985-03-04 SG SG163/85A patent/SG16385G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX159971A (es) | 1989-10-17 |
| NO820660L (no) | 1982-09-06 |
| NO159284C (no) | 1988-12-14 |
| ES510130A0 (es) | 1983-06-16 |
| DE3280033D1 (en) | 1989-12-28 |
| ES8306768A1 (es) | 1983-06-16 |
| US4394291A (en) | 1983-07-19 |
| BR8201027A (pt) | 1983-01-04 |
| GB2093851A (en) | 1982-09-08 |
| JPS57158207A (en) | 1982-09-30 |
| EP0060443A1 (en) | 1982-09-22 |
| EP0060443B1 (en) | 1989-11-23 |
| SG16385G (en) | 1985-08-16 |
| ATE48145T1 (de) | 1989-12-15 |
| JPH0465084B2 (no) | 1992-10-19 |
| GB2093851B (en) | 1985-01-09 |
| CA1183119A (en) | 1985-02-26 |
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