DD151759A5 - Verfahren zur herstellung silyierter polyaether - Google Patents
Verfahren zur herstellung silyierter polyaether Download PDFInfo
- Publication number
- DD151759A5 DD151759A5 DD80222214A DD22221480A DD151759A5 DD 151759 A5 DD151759 A5 DD 151759A5 DD 80222214 A DD80222214 A DD 80222214A DD 22221480 A DD22221480 A DD 22221480A DD 151759 A5 DD151759 A5 DD 151759A5
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- DD
- German Democratic Republic
- Prior art keywords
- radical
- radicals
- carbon
- formula
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- 238000000034 method Methods 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 oxyalkylene compound Chemical class 0.000 claims abstract description 85
- 229920000570 polyether Polymers 0.000 claims abstract description 65
- 239000000463 material Substances 0.000 claims abstract description 38
- 239000004753 textile Substances 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 19
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910000077 silane Inorganic materials 0.000 claims abstract description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000003254 radicals Chemical class 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 23
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002091 cationic group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920003180 amino resin Polymers 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 abstract description 4
- 239000007858 starting material Substances 0.000 abstract description 3
- 239000011734 sodium Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000001846 repelling effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 36
- 229920001577 copolymer Polymers 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 13
- 239000004744 fabric Substances 0.000 description 13
- 229940014800 succinic anhydride Drugs 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 3
- 229920004934 Dacron® Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HXJZEGBVQCRLOD-UHFFFAOYSA-N 1-triethoxysilylpropan-2-amine Chemical compound CCO[Si](CC(C)N)(OCC)OCC HXJZEGBVQCRLOD-UHFFFAOYSA-N 0.000 description 1
- GXCDRJSFHAJTAI-UHFFFAOYSA-N 2-(1-trimethoxysilylpropan-2-yloxy)ethanamine Chemical compound CO[Si](OC)(OC)CC(C)OCCN GXCDRJSFHAJTAI-UHFFFAOYSA-N 0.000 description 1
- SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZFAITYKOYYJOIJ-UHFFFAOYSA-N 3-(2,2-dihydroxyethyl)-1,1-bis(hydroxymethyl)urea Chemical compound C(O)N(C(NCC(O)O)=O)CO ZFAITYKOYYJOIJ-UHFFFAOYSA-N 0.000 description 1
- ZDZYGYFHTPFREM-UHFFFAOYSA-N 3-[3-aminopropyl(dimethoxy)silyl]oxypropan-1-amine Chemical compound NCCC[Si](OC)(OC)OCCCN ZDZYGYFHTPFREM-UHFFFAOYSA-N 0.000 description 1
- JMFBXUMHVSZUKY-UHFFFAOYSA-N 3-bromopropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCBr JMFBXUMHVSZUKY-UHFFFAOYSA-N 0.000 description 1
- IIFBEYQLKOBDQH-UHFFFAOYSA-N 3-chloropropyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCCCl IIFBEYQLKOBDQH-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- RXWJNRNTLJCMOD-UHFFFAOYSA-N 4-bromobutyl-ethyl-dimethoxysilane Chemical compound CC[Si](OC)(OC)CCCCBr RXWJNRNTLJCMOD-UHFFFAOYSA-N 0.000 description 1
- NCZKQXDWBVYFQA-UHFFFAOYSA-N 4-iodobutyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCI NCZKQXDWBVYFQA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- 206010040007 Sense of oppression Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000001153 anti-wrinkle effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- MIGNWTQKRPNYLP-UHFFFAOYSA-N but-2-ene-2,3-diol urea Chemical compound NC(=O)N.OC(=C(C)O)C MIGNWTQKRPNYLP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
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- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
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- 239000011487 hemp Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 230000002045 lasting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- YQMWDQQWGKVOSQ-UHFFFAOYSA-N trinitrooxystannyl nitrate Chemical compound [Sn+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YQMWDQQWGKVOSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31736—Next to polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/3175—Next to addition polymer from unsaturated monomer[s]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/074,188 US4312993A (en) | 1979-09-10 | 1979-09-10 | Silylated polyethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD151759A5 true DD151759A5 (de) | 1981-11-04 |
Family
ID=22118203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80222214A DD151759A5 (de) | 1979-09-10 | 1980-06-27 | Verfahren zur herstellung silyierter polyaether |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4312993A (fr) |
| EP (1) | EP0026366B1 (fr) |
| JP (1) | JPS5640691A (fr) |
| KR (1) | KR840000038B1 (fr) |
| AU (1) | AU527193B2 (fr) |
| BR (1) | BR8003398A (fr) |
| CA (1) | CA1158253A (fr) |
| DD (1) | DD151759A5 (fr) |
| DE (1) | DE3064640D1 (fr) |
| DK (1) | DK338680A (fr) |
| ES (2) | ES8105349A1 (fr) |
| IE (1) | IE49771B1 (fr) |
| IL (1) | IL59828A (fr) |
| MX (1) | MX154095A (fr) |
| NO (1) | NO802660L (fr) |
| NZ (1) | NZ193875A (fr) |
| SE (1) | SE8003908L (fr) |
| ZA (1) | ZA802220B (fr) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL62282A (en) * | 1980-07-18 | 1984-11-30 | Sws Silicones Corp | Silicone polymer compositions,their preparation and their use for treating textile materials |
| US4401698A (en) * | 1980-09-18 | 1983-08-30 | Sws Silicones Corporation | Hydrophilic coatings for textile materials |
| US4352917A (en) * | 1980-09-18 | 1982-10-05 | Sws Silicones Corporation | Hydrophilic coatings for textile materials |
| DE3214985C2 (de) * | 1982-04-22 | 1985-07-04 | Th. Goldschmidt Ag, 4300 Essen | Verfahren zur Herstellung eines mit Wasser verdünnbaren, wärmehärtbaren, mit organischen Polyolen modifizierten Organopolysiloxans |
| DE3214984C2 (de) * | 1982-04-22 | 1985-05-15 | Th. Goldschmidt Ag, 4300 Essen | Verfahren zur Herstellung von eines in organischen Lösungsmitteln löslichen, hitzehärtbaren Siliconharzes |
| US4390713A (en) * | 1982-05-21 | 1983-06-28 | Sws Silicones Corporation | Quaternary ammonium-functional silicon compounds |
| US4394517A (en) * | 1982-05-21 | 1983-07-19 | Sws Silicones Corporation | Quaternary ammonium functional silicon compounds |
| US4615706A (en) * | 1982-05-21 | 1986-10-07 | Stauffer-Wacker Silicones Corporation | Quaternary ammonium-functional silicon compounds |
| US4384130A (en) * | 1982-05-21 | 1983-05-17 | Sws Silicones Corporation | Quaternary ammonium-functional silicon compounds |
| US4511727A (en) * | 1982-05-21 | 1985-04-16 | Sws Silicones Corporation | Quaternary ammonium-functional silicon compounds |
| US4512764A (en) * | 1982-09-27 | 1985-04-23 | Wunsch Richard E | Manifold for controlling administration of multiple intravenous solutions and medications |
| AU1417383A (en) * | 1982-09-30 | 1984-04-05 | Sws Silicones Corp. | Textile finishing composition |
| US4588830A (en) * | 1982-12-09 | 1986-05-13 | The Dow Chemical Company | Addition polymerizable adducts for nonaqueous dispersions |
| JPS59179883A (ja) * | 1983-03-30 | 1984-10-12 | 竹本油脂株式会社 | 繊維処理用油剤及び該油剤による熱可塑性合成繊維糸の処理方法 |
| US4668716A (en) * | 1983-09-30 | 1987-05-26 | Union Carbide Corporation | Novel fatty ethenoid acylaminoorganosilicon compounds and their use as a coupling agent |
| US4584138A (en) * | 1983-09-30 | 1986-04-22 | Union Carbide Corporation | Novel fatty ethenoid acylaminoorganosilicon compounds and their use as a coupling agent |
| FR2557735B1 (fr) * | 1984-01-02 | 1986-04-25 | Elf Aquitaine | Nouveau materiau macromoleculaire a conduction ionique et son procede de fabrication |
| US4699966A (en) * | 1984-01-30 | 1987-10-13 | Loctite (Ireland) Ltd. | Polymer bound calixarenes |
| US5286562A (en) * | 1988-07-01 | 1994-02-15 | Ppg Industries, Inc. | Weavable textile glass strand |
| US5041593A (en) * | 1989-07-19 | 1991-08-20 | Dow Corning Corporation | Method for preparation of silyl functional fumarates |
| US5296625A (en) * | 1991-11-06 | 1994-03-22 | Siltech Inc. | Silicone alkoxylated esters carboxylates |
| US5408012A (en) * | 1993-05-27 | 1995-04-18 | Comfort Technologies, Inc. | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
| GB9424247D0 (en) * | 1994-12-01 | 1995-01-18 | Dow Corning Sa | Silyl group containing organic polymers |
| GB9424250D0 (en) * | 1994-12-01 | 1995-01-18 | Dow Corning Sa | Silyl group containing organic polymers |
| GB9424246D0 (en) * | 1994-12-01 | 1995-01-18 | Dow Corning Sa | Moisture curable compositions |
| US6511928B2 (en) | 1998-09-30 | 2003-01-28 | The Procter & Gamble Company | Rayon fabric with substantial shrink-resistant properties |
| US5885303A (en) | 1997-05-13 | 1999-03-23 | American Laundry Machinery Incorporated | Durable press/wrinkle-free process |
| US6375685B2 (en) | 1997-05-13 | 2002-04-23 | The Procter & Gamble Company | Textile finishing process |
| US6565612B2 (en) | 1998-09-30 | 2003-05-20 | The Procter & Gamble Company | Shrink resistant rayon fabrics |
| US7169293B2 (en) * | 1999-08-20 | 2007-01-30 | Uop Llc | Controllable space velocity reactor and process |
| US7144431B2 (en) * | 2001-10-18 | 2006-12-05 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
| US7018422B2 (en) | 2001-10-18 | 2006-03-28 | Robb Richard Gardner | Shrink resistant and wrinkle free textiles |
| US7008457B2 (en) * | 2001-10-18 | 2006-03-07 | Mark Robert Sivik | Textile finishing composition and methods for using same |
| US6989035B2 (en) | 2001-10-18 | 2006-01-24 | The Procter & Gamble Company | Textile finishing composition and methods for using same |
| US6841198B2 (en) * | 2001-10-18 | 2005-01-11 | Strike Investments, Llc | Durable press treatment of fabric |
| US7169742B2 (en) * | 2001-10-18 | 2007-01-30 | The Procter & Gamble Company | Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents |
| US7919722B2 (en) | 2006-10-30 | 2011-04-05 | Applied Materials, Inc. | Method for fabricating plasma reactor parts |
| USD906088S1 (en) * | 2018-12-03 | 2020-12-29 | Charlie Pizanias | Adjustable lock down door bar |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128826C (fr) * | 1963-09-30 | |||
| US3694480A (en) * | 1968-06-11 | 1972-09-26 | Union Carbide Corp | Novel organofunctional silicon compounds substituted with halogen and processes for making same |
| GB1257650A (fr) * | 1968-12-30 | 1971-12-22 | ||
| DE1905101C3 (de) * | 1969-02-01 | 1978-06-22 | Bayer Ag, 5090 Leverkusen | Siloxanmodifizierte Carbamidsäurederivate |
| US3639156A (en) * | 1970-05-19 | 1972-02-01 | Us Agriculture | Siloxane polymers for soil-repellent and soil-release textile finishes |
| US3861915A (en) * | 1973-03-30 | 1975-01-21 | Eastman Kodak Co | Block copolyesters of polysiloxanes as additives to photoconductive layers |
| US3876459A (en) * | 1973-06-29 | 1975-04-08 | Dow Corning | Treatment of fibres |
| US4088670A (en) * | 1974-10-01 | 1978-05-09 | Rhone-Poulenc Industries | Ethylenic silicon compounds and thermoplastic elastomers obtained therefrom |
| US4260725A (en) * | 1979-12-10 | 1981-04-07 | Bausch & Lomb Incorporated | Hydrophilic contact lens made from polysiloxanes which are thermally bonded to polymerizable groups and which contain hydrophilic sidechains |
-
1979
- 1979-09-10 US US06/074,188 patent/US4312993A/en not_active Expired - Lifetime
-
1980
- 1980-04-11 AU AU57369/80A patent/AU527193B2/en not_active Ceased
- 1980-04-14 ZA ZA00802220A patent/ZA802220B/xx unknown
- 1980-04-14 IL IL5982880A patent/IL59828A/xx unknown
- 1980-04-23 MX MX182060A patent/MX154095A/es unknown
- 1980-04-29 IE IE869/80A patent/IE49771B1/en unknown
- 1980-05-13 JP JP6267480A patent/JPS5640691A/ja active Granted
- 1980-05-23 KR KR1019800002020A patent/KR840000038B1/ko active
- 1980-05-27 SE SE8003908A patent/SE8003908L/ not_active Application Discontinuation
- 1980-05-29 NZ NZ19387580A patent/NZ193875A/xx unknown
- 1980-05-30 BR BR8003398A patent/BR8003398A/pt unknown
- 1980-05-30 CA CA000353113A patent/CA1158253A/fr not_active Expired
- 1980-06-27 DD DD80222214A patent/DD151759A5/de unknown
- 1980-06-30 ES ES492943A patent/ES8105349A1/es not_active Expired
- 1980-07-18 US US06/170,297 patent/US4331797A/en not_active Expired - Lifetime
- 1980-08-06 DK DK338680A patent/DK338680A/da not_active Application Discontinuation
- 1980-09-09 NO NO802660A patent/NO802660L/no unknown
- 1980-09-10 DE DE8080105396T patent/DE3064640D1/de not_active Expired
- 1980-09-10 EP EP80105396A patent/EP0026366B1/fr not_active Expired
-
1981
- 1981-01-30 ES ES498995A patent/ES8205279A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1158253A (fr) | 1983-12-06 |
| KR840000038B1 (ko) | 1984-01-28 |
| NZ193875A (en) | 1983-06-14 |
| EP0026366A1 (fr) | 1981-04-08 |
| SE8003908L (sv) | 1981-03-11 |
| ES492943A0 (es) | 1981-05-16 |
| AU5736980A (en) | 1981-03-19 |
| BR8003398A (pt) | 1981-03-24 |
| ES498995A0 (es) | 1982-06-01 |
| JPS5640691A (en) | 1981-04-16 |
| US4331797A (en) | 1982-05-25 |
| NO802660L (no) | 1981-03-11 |
| ES8205279A1 (es) | 1982-06-01 |
| DK338680A (da) | 1981-03-11 |
| IE49771B1 (en) | 1985-12-11 |
| JPH0234956B2 (fr) | 1990-08-07 |
| ZA802220B (en) | 1981-11-25 |
| MX154095A (es) | 1987-05-07 |
| KR830002833A (ko) | 1983-05-30 |
| US4312993A (en) | 1982-01-26 |
| EP0026366B1 (fr) | 1983-08-24 |
| DE3064640D1 (en) | 1983-09-29 |
| AU527193B2 (en) | 1983-02-17 |
| IL59828A (en) | 1983-09-30 |
| IE800869L (en) | 1981-03-10 |
| IL59828A0 (en) | 1980-06-30 |
| ES8105349A1 (es) | 1981-05-16 |
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