IL28877A - Anionic lactam catalyst solution for the polymerisation of lactams - Google Patents

Anionic lactam catalyst solution for the polymerisation of lactams

Info

Publication number: IL28877A
Authority: IL; Israel
Prior art keywords: lactam; metal; sulfoxide; disubstituted; catalyst
Prior art date: 1966-11-18

Application number

IL28877A

Other languages

English (en)

Original Assignee

Monsanto Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-11-18

Filing date

1967-11-01

Publication date

1972-01-27

1967-11-01 Application filed by Monsanto Co filed Critical Monsanto Co

1972-01-27 Publication of IL28877A publication Critical patent/IL28877A/en

Links

239000003054 catalyst Substances 0.000 title claims description 62
150000003951 lactams Chemical class 0.000 title claims description 55
-1 Anionic lactam Chemical class 0.000 title claims description 24
229910052751 metal Inorganic materials 0.000 claims description 49
239000002184 metal Substances 0.000 claims description 49
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 28
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 23
239000007788 liquid Substances 0.000 claims description 23
150000003462 sulfoxides Chemical class 0.000 claims description 23
238000012693 lactam polymerization Methods 0.000 claims description 18
229910052749 magnesium Inorganic materials 0.000 claims description 18
235000001055 magnesium Nutrition 0.000 claims description 18
239000011777 magnesium Substances 0.000 claims description 18
229940091250 magnesium supplement Drugs 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
230000008569 process Effects 0.000 claims description 9
229910052708 sodium Inorganic materials 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
230000003014 reinforcing effect Effects 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
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 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
150000002736 metal compounds Chemical class 0.000 claims description 6
150000004703 alkoxides Chemical class 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 4
150000004681 metal hydrides Chemical class 0.000 claims description 4
230000006872 improvement Effects 0.000 claims description 3
229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
150000004692 metal hydroxides Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000003505 polymerization initiator Substances 0.000 claims description 3
239000011256 inorganic filler Substances 0.000 claims 1
229910003475 inorganic filler Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 description 37
239000000178 monomer Substances 0.000 description 34
239000002904 solvent Substances 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000006116 polymerization reaction Methods 0.000 description 15
239000002002 slurry Substances 0.000 description 15
239000000945 filler Substances 0.000 description 13
239000002685 polymerization catalyst Substances 0.000 description 12
DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 11
239000000654 additive Substances 0.000 description 11
238000002156 mixing Methods 0.000 description 11
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
239000007787 solid Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 7
229910052782 aluminium Inorganic materials 0.000 description 7
238000004821 distillation Methods 0.000 description 7
150000007975 iminium salts Chemical class 0.000 description 7
239000003999 initiator Substances 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000000996 additive effect Effects 0.000 description 6
238000001879 gelation Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
MOMGDEWWZBKDDR-UHFFFAOYSA-M sodium;3,4,5,6-tetrahydro-2h-azepin-7-olate Chemical compound [Na+].O=C1CCCCC[N-]1 MOMGDEWWZBKDDR-UHFFFAOYSA-M 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012744 reinforcing agent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000007822 coupling agent Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000000379 polymerizing effect Effects 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000011952 anionic catalyst Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000005266 casting Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 description 2
WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
OJTRWQFLEGVVKJ-UHFFFAOYSA-N cyclopentylsulfinylcyclopentane Chemical compound C1CCCC1S(=O)C1CCCC1 OJTRWQFLEGVVKJ-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
229910001623 magnesium bromide Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000001282 organosilanes Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
235000007686 potassium Nutrition 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910052712 strontium Inorganic materials 0.000 description 2
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
239000002023 wood Substances 0.000 description 2
UDDBCWCQRQREBI-UHFFFAOYSA-N 1-methylsulfinylethene Chemical compound CS(=O)C=C UDDBCWCQRQREBI-UHFFFAOYSA-N 0.000 description 1
VWCFQNQVNVMFGV-UHFFFAOYSA-N 1-octylsulfinyloctane Chemical compound CCCCCCCCS(=O)CCCCCCCC VWCFQNQVNVMFGV-UHFFFAOYSA-N 0.000 description 1
LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Natural products CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 1
DPWSGFWYGDIGTM-UHFFFAOYSA-N 2-ethylsulfinylpropane Chemical compound CCS(=O)C(C)C DPWSGFWYGDIGTM-UHFFFAOYSA-N 0.000 description 1
XYGIHYNABFJESU-UHFFFAOYSA-N 3-prop-2-enylsulfinylprop-1-ene Chemical compound C=CCS(=O)CC=C XYGIHYNABFJESU-UHFFFAOYSA-N 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 1
239000005955 Ferric phosphate Substances 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000012190 activator Substances 0.000 description 1
238000004026 adhesive bonding Methods 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
CNLWCVNCHLKFHK-UHFFFAOYSA-N aluminum;lithium;dioxido(oxo)silane Chemical compound [Li+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O CNLWCVNCHLKFHK-UHFFFAOYSA-N 0.000 description 1
INJRKJPEYSAMPD-UHFFFAOYSA-N aluminum;silicic acid;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O INJRKJPEYSAMPD-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
238000005844 autocatalytic reaction Methods 0.000 description 1
YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
HTMQZWFSTJVJEQ-UHFFFAOYSA-N benzylsulfinylmethylbenzene Chemical compound C=1C=CC=CC=1CS(=O)CC1=CC=CC=C1 HTMQZWFSTJVJEQ-UHFFFAOYSA-N 0.000 description 1
HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910052620 chrysotile Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000010433 feldspar Substances 0.000 description 1
229940032958 ferric phosphate Drugs 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000003517 fume Substances 0.000 description 1
239000002223 garnet Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
229910000271 hectorite Inorganic materials 0.000 description 1
229910001691 hercynite Inorganic materials 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
229910000399 iron(III) phosphate Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
239000010443 kyanite Substances 0.000 description 1
229910052850 kyanite Inorganic materials 0.000 description 1
239000011133 lead Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
229910052863 mullite Inorganic materials 0.000 description 1
WZKOKGOAHBIPCI-UHFFFAOYSA-N n,n,4-trimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C)C=C1 WZKOKGOAHBIPCI-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000000803 paradoxical effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000000049 pigment Substances 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229940088417 precipitated calcium carbonate Drugs 0.000 description 1
239000002243 precursor Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
229910000275 saponite Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
229910052642 spodumene Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000011135 tin Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
ULEFFCDROVNTRO-UHFFFAOYSA-N trimagnesium;disodium;dihydroxy(oxo)silane;iron(3+) Chemical compound [Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Fe+3].[Fe+3].O[Si](O)=O.O[Si](O)=O.O[Si](O)=O.O[Si](O)=O.O[Si](O)=O.O[Si](O)=O.O[Si](O)=O.O[Si](O)=O ULEFFCDROVNTRO-UHFFFAOYSA-N 0.000 description 1
CWBIFDGMOSWLRQ-UHFFFAOYSA-N trimagnesium;hydroxy(trioxido)silane;hydrate Chemical compound O.[Mg+2].[Mg+2].[Mg+2].O[Si]([O-])([O-])[O-].O[Si]([O-])([O-])[O-] CWBIFDGMOSWLRQ-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000010456 wollastonite Substances 0.000 description 1
229910052882 wollastonite Inorganic materials 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0228—Sulfur-containing compounds with a metal-sulfur link, e.g. mercaptides
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0252—Nitrogen containing compounds with a metal-nitrogen link, e.g. metal amides, metal guanidides
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
- C08G69/20—Anionic polymerisation characterised by the catalysts used

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyamides (AREA)
Hydrogenated Pyridines (AREA)

IL28877A 1966-11-18 1967-11-01 Anionic lactam catalyst solution for the polymerisation of lactams IL28877A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US59533466A	1966-11-18	1966-11-18

Publications (1)

Publication Number	Publication Date
IL28877A true IL28877A (en)	1972-01-27

Family

ID=24382825

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28877A IL28877A (en)	1966-11-18	1967-11-01	Anionic lactam catalyst solution for the polymerisation of lactams

Country Status (10)

Country	Link
US (1)	US3450662A (fr)
BE (1)	BE706110A (fr)
CH (1)	CH478174A (fr)
DE (1)	DE1695519A1 (fr)
DK (1)	DK138082B (fr)
ES (1)	ES347331A1 (fr)
FR (1)	FR1554779A (fr)
GB (1)	GB1206649A (fr)
IL (1)	IL28877A (fr)
NL (1)	NL155283B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1285051A (en) *	1969-03-27	1972-08-09	Ici Ltd	Fibre reinforced polymer compositions
US3901845A (en) *	1974-04-01	1975-08-26	Gen Motors Corp	Filled and reinforced polyamide molding compositions
IT1033860B (it) *	1975-02-13	1979-08-10	Russo S	Processo di polimerizzazione di poliammidi lavorabili a temperature piu basse delle loro temperature convenzionali di fusione e di decomposizione
US4098774A (en) *	1976-05-19	1978-07-04	Chevron Research Company	Quaternary ammonium catalyst system for the polymerization of 2-pyrrolidone
US4683344A (en) *	1984-01-30	1987-07-28	Ppg Industries, Inc.	Process for the preparation of an organomagnesium compound
US4508646A (en) *	1984-01-30	1985-04-02	Ppg Industries, Inc.	Process for the preparation of a catalyst useful for anionic lactam polymerization
DE3730538A1 (de) *	1987-09-11	1989-03-30	Basf Ag	Polycaprolactame mit einem gehalt an titandioxid und dessen verwendung

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA676302A (en) *		1963-12-17	A. Lewis Dennis	Lactam polymerisation
US2806829A (en) *	1955-04-25	1957-09-17	Chemstrand Corp	Solutions of polycaprolactam in dimethyl sulfoxide and method of making same
US3018273A (en) *	1958-04-21	1962-01-23	Monsanto Chemicals	Process of polymerizing higher lactams
US3017391A (en) *	1956-12-13	1962-01-16	Monsanto Chemicals	Preparation of polycaprolactam using n-acyl activators
US3017392A (en) *	1956-12-13	1962-01-16	Monsanto Chemicals	Polymerization of higher lactams
US3342783A (en) *	1962-04-06	1967-09-19	Hoechst Ag	Process for the manufacture of polyamides from alpha, alpha-dialkyl substituted beta-lactams
DE1301112C2 (de) *	1963-05-11	1973-08-02	Degussa	Verfahren zur Herstellung von Formkoerpern auf der Basis von Polyamiden

1966
- 1966-11-18 US US595334A patent/US3450662A/en not_active Expired - Lifetime
1967
- 1967-11-01 IL IL28877A patent/IL28877A/en unknown
- 1967-11-06 BE BE706110D patent/BE706110A/xx unknown
- 1967-11-10 CH CH1569567A patent/CH478174A/fr not_active IP Right Cessation
- 1967-11-15 DE DE19671695519 patent/DE1695519A1/de active Pending
- 1967-11-17 FR FR1554779D patent/FR1554779A/fr not_active Expired
- 1967-11-17 GB GB52488/67A patent/GB1206649A/en not_active Expired
- 1967-11-17 NL NL676715660A patent/NL155283B/xx unknown
- 1967-11-17 DK DK575167AA patent/DK138082B/da unknown
- 1967-11-18 ES ES347331A patent/ES347331A1/es not_active Expired

Also Published As

Publication number	Publication date
ES347331A1 (es)	1969-05-16
GB1206649A (en)	1970-09-23
DK138082C (fr)	1978-12-11
DE1695519A1 (de)	1972-03-09
FR1554779A (fr)	1969-01-24
NL155283B (nl)	1977-12-15
CH478174A (fr)	1969-09-15
US3450662A (en)	1969-06-17
DK138082B (da)	1978-07-10
NL6715660A (fr)	1968-05-20
BE706110A (fr)	1968-05-06

Publication	Publication Date	Title
US3086962A (en)	1963-04-23	Process for polymerizing higher lactams
US3451963A (en)	1969-06-24	Polymerization of lactams
US3372137A (en)	1968-03-05	Process for preparing mineral reinforced polylactam compositions
US3575938A (en)	1971-04-20	Anionic lactam catalyst system
EP0222432A1 (fr)	1987-05-20	Polymérisation en masse de dicyclopentadiène
IL28877A (en)	1972-01-27	Anionic lactam catalyst solution for the polymerisation of lactams
US3121768A (en)	1964-02-18	Method of casting
US3341501A (en)	1967-09-12	Polyamides containing silane end groups
EP0536697B1 (fr)	1996-06-05	Polysilazanes substitués par un péroxyde
KR900004791B1 (ko)	1990-07-05	나일론-6-중합체의 제조방법
US4214065A (en)	1980-07-22	Reinforced polylactams
CN102199169A (zh)	2011-09-28	有机酰胺基硅烷的一种新的制备方法
US3671501A (en)	1972-06-20	Lactam polymerization with substituted biuret initiators
US3567696A (en)	1971-03-02	Storable polyamide-forming compositions and process for the production of polyamides
US3919175A (en)	1975-11-11	Method of anionic polymerization and copolymerization of lactam of {107 -aminocarboxylic acids
JPS61143431A (ja)	1986-07-01	粘稠化ラクタム重合開始剤溶液
JPS61281126A (ja)	1986-12-11	ラクタムを重合せさる方法及びそれより得られる生成物
US3410831A (en)	1968-11-12	Anionic process for preparing reinforced polylactam in the presence of a coupling agent and a tetraalkyl orthosilicate
JPS6132334B2 (fr)	1986-07-26
US3397185A (en)	1968-08-13	Anionic polymerization of lactams with a carbonate diester containing nu-heterocyclic substituent as promoter
JPH0248172B2 (fr)	1990-10-24
US4596865A (en)	1986-06-24	Promotion of ε-caprolactam block copolymerization
US3681296A (en)	1972-08-01	Polymerization of 2-pyrrolidone using azetidinone co-activators and carbon dioxide as activator
JPH03170533A (ja)	1991-07-24	ポリシラザン及びその製法
US3696075A (en)	1972-10-03	Lactam polymerization with diacyl methane initiators