FI85591B - Vattenloesliga polyuretankampolymerer samt deras framstaellning. - Google Patents
Vattenloesliga polyuretankampolymerer samt deras framstaellning. Download PDFInfo
- Publication number
- FI85591B FI85591B FI844942A FI844942A FI85591B FI 85591 B FI85591 B FI 85591B FI 844942 A FI844942 A FI 844942A FI 844942 A FI844942 A FI 844942A FI 85591 B FI85591 B FI 85591B
- Authority
- FI
- Finland
- Prior art keywords
- polymer
- polyethylene glycol
- hydrophobic
- polyisocyanate
- residue
- Prior art date
Links
- 101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims description 111
- 230000002209 hydrophobic effect Effects 0.000 claims description 95
- 229920001223 polyethylene glycol Polymers 0.000 claims description 72
- 239000002202 Polyethylene glycol Substances 0.000 claims description 58
- 239000007858 starting material Substances 0.000 claims description 45
- -1 nonylphenyl Chemical group 0.000 claims description 38
- 229920001228 polyisocyanate Polymers 0.000 claims description 34
- 239000005056 polyisocyanate Substances 0.000 claims description 34
- 239000004814 polyurethane Substances 0.000 claims description 33
- 229920002635 polyurethane Polymers 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 125000001165 hydrophobic group Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 230000008719 thickening Effects 0.000 claims description 26
- 150000002009 diols Chemical class 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229920001519 homopolymer Polymers 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003827 glycol group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- OQYDOTAIOMTHEN-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1NCNC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1NCNC1=CC=CC=C1 OQYDOTAIOMTHEN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000002245 particle Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 11
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 10
- 239000004816 latex Substances 0.000 description 10
- 229920000126 latex Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 6
- 239000000693 micelle Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920003169 water-soluble polymer Polymers 0.000 description 5
- YITMLDIGEJSENC-HWKANZROSA-N (e)-hexadec-2-ene Chemical compound CCCCCCCCCCCCC\C=C\C YITMLDIGEJSENC-HWKANZROSA-N 0.000 description 4
- XWAMHGPDZOVVND-UHFFFAOYSA-N 1,2-octadecanediol Chemical compound CCCCCCCCCCCCCCCCC(O)CO XWAMHGPDZOVVND-UHFFFAOYSA-N 0.000 description 4
- YITMLDIGEJSENC-UHFFFAOYSA-N Hexadecen Natural products CCCCCCCCCCCCCC=CC YITMLDIGEJSENC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- KUQIWULJSBTNPX-HWKANZROSA-N (e)-octadec-2-ene Chemical compound CCCCCCCCCCCCCCC\C=C\C KUQIWULJSBTNPX-HWKANZROSA-N 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 2
- BTOOAFQCTJZDRC-UHFFFAOYSA-N 1,2-hexadecanediol Chemical compound CCCCCCCCCCCCCCC(O)CO BTOOAFQCTJZDRC-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009499 grossing Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229940096826 phenylmercuric acetate Drugs 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229940031723 1,2-octanediol Drugs 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- DAHZCNRVTNHGGR-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-diol Chemical compound OCC(O)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DAHZCNRVTNHGGR-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- FLSYUAYKNBCPHB-UHFFFAOYSA-N CC(C)(C1)CC(C)(CN=C=O)CC1N=C=O.N=C=O.N=C=O.C(NC1=CC=CC=C1)NC1=CC=CC=C1 Chemical compound CC(C)(C1)CC(C)(CN=C=O)CC1N=C=O.N=C=O.N=C=O.C(NC1=CC=CC=C1)NC1=CC=CC=C1 FLSYUAYKNBCPHB-UHFFFAOYSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYKAKDPHDGCKTF-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOO FYKAKDPHDGCKTF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- ZZUFUNZTPNRBID-UHFFFAOYSA-K bismuth;octanoate Chemical compound [Bi+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ZZUFUNZTPNRBID-UHFFFAOYSA-K 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 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
- 239000003792 electrolyte Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002398 hexadecan-1-ols Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229920013746 hydrophilic polyethylene oxide Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- 230000037361 pathway Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4858—Polyethers containing oxyalkylene groups having more than four carbon atoms in the alkylene group
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4862—Polyethers containing at least a part of the ether groups in a side chain
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Engineering & Computer Science (AREA)
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- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
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Claims (24)
1. Kampolymer som omfattar ett vattenlösligt polyuretan, som innehäller de äterkommande enheterna Xe' “/ “ Yb" OCh ” ( “X" ) m~ Zo “ där: X är resten av ett organiskt polyisocyanat; Y är resten av en polyetylenglykolhomopolymer eller -sampolymer med upp till 50 molprocent C3 - Cs-polyoxialkylen, eller den monomera ekvivalenten av nämnda polyetylenglykol; Z är resten av en hydrofob reaktant som innehäller en monovalent hydrofob grupp som ger en molvolymkontribution om atminstone ca 130 cm1/mol; b är minst ca 2; £ är minst ca 2; m är 0 eller 1; a' är sadan, att (a'+mc)/(b+c) är ca 0, 50...1, 25 och tillräcklig för att ge en polymermolekylvikt om minst 10000, kännetecknadav att (1) polymeren har minst en Z-enhet separerad frän vardera änden av polymeren med minst en Y-enhet; och (2) polymerens hydrofil/lipofilbalans är 14...19,5, varvid ·.: (3) Z-enheterna är närvarande i polymeren som en- skilda hydrofober.
2. Polymer enligt patentkravet 1, kännetecknadav att polyisocyanatet har strukturen: ; 0=C=N-Ri -N=C*0 där Ri är alkylen, cykloalkylen eller arylen. Polymer enligt patentkravet 2, kännetecknadav att polyisocyanatet är toluendiisocyanat, metylendianilindi-isocyanat eller isoforondiisocyanat. 42 85591
4. Polymer enligt patentkravet 1, kännetecknad av att polyetylenglykolen är en homopolymer med en molekylvikt om upp till ca 14000.
5. Polymer enligt patentkravet 1, kännetecknad av att den monovalenta hydrofobgruppens molvolymkontribution är minst ca 190 cm3/mol.
6. Polymer enligt patentkravet 1, kännetecknad av att den monovalenta hydrofobgruppen är en osubstituerad eller halogensubstituerad kolväteradikal med minst 8 kolatomer.
7. Polymer enligt patentkravet 6, kännetecknad av att kolväteradikalen har minst 12 kolatomer.
8. Polymer enligt patentkravet 7, kännetecknad av att kolväteradikalen är alkyl eller aralkyl med ca 14...16 kolatomer.
9. Polymer enligt patentkravet 8, kännetecknad av att kolväteradikalen är nonylfenyl, n-tetradecyl eller n-hexa-decyl.
10. Polymer enligt patentkravet 1, kännetecknad av att polyuretanet har ändhydroxylgrupper.
11. Polymer enligt patentkravet 1, kännetecknad av att m är 1 och att polyuretanet har formeln: HO -{—(—Y-X——Z-X-hr-Y-OH (II) där b^_ är medeltalet av antalet av polyetylenglykol- : rester per hydrofobrest; och c, X, Y och Z betecknar samma som ovan definierats.
12. Polymer enligt patentkravet 1, kännetecknad av att m är 0 och polyuretanet har formeln: 43 85591 HO—[—f-Yi-ZcP—Ya·· )b--T-X- |—Y-OH (III) där a, b, X och Z betecknar samma som ovan definierats, £' är medeltalet av antalet monovalenta hydrofob-grupper per äterkommande polyetylenglykolenhet; och Yi och Ϊ2 är rester av nämnda polyetylenglykol eller monomera ekvivalent, vilka bringats att reagera med nämnda hydrofobreaktant.
13. En förtjocknande vattenlösning, som innehaller en effektiv förtjockande mängd av kampolymeren enligt patentkravet 1, som omfattar ett vattenlösligt polyuretan, som innehaller de äterkommande enheterna — Xa‘ -/ - Yt>- OCh — (— X- ) m-Zc~ där: X är resten av ett organiskt polyisocyanat; Y är resten av en polyetylenglykolhomopolymer eller -sampolymer med upp tili 50 molprocent C3 - Cs-polyoxialkylen, eller den monomera ekvivalenten av nämnda polyetylenglykol; Z är resten av en hydrofob reaktant som innehaller en monovalent hydrofob grupp som ger en molvolymkontribution om ätminstone ca 130 cm3/mol; b är minst ca 2; £ är minst ca 2; m är 0 eller 1; a' är sädan, att (a' +mc) / (b+c) är ca 0, 50...1, 25 och tillräcklig för att ge en molekylvikt om minst 10000, kännetecknad av att (1) polymeren har minst en Z-enhet separerad frän vardera änden av polymeren med minst en Y-enhet; och (2) polymerens hydrofil/lipofilbalans är 14...19,5, varvid (3) Z-enheterna är närvarande i polymeren som en-skilda hydrofober.
14. Förfarande för framställning av en kampolymer enligt patentkravet 1 som är ett vattenlösligt polyuretan, i vilket 44 85591 förfarande, man bringar (a) a mol av ett organiskt polyisocyanat; (b) b mol av en polyetylenglykolhomopolymer eller -sampolymer med upp tili 50 molprocent C3 - Cs-polyoxialkylen, eller den monomera ekvivalenten av nämnda polyetylenglykol; och (c) £ mol av en hydrofob reaktant som innehäller en monovalent hydrofob grupp och som ger en molvolymkontribution om ätminstone ca 130 cm3/mol, att reagera med varandra, varvid b är minst ca 2; £ är minst ca 2; a är sadan, att a/(b + c) är ca 0, 50. . . 1, 25 och till-räcklig för att ge en molekylvikt om minst 10000; känne-t e c n a t av att komponenterna bringas att reagera (d) pä ett sätt, som är tillräckligt för att produ-cera nämnda polymer med (1) minst en monovalent hydrofob grupp separerad fran vardera änden av polymeren med minst en poly-etylenglykolrest och (2) en hydrofil/lipofilbalans om 14...19,5, varvid (3) hydrofobgrupperna är närvarande som enskilda hydrofober.
15. Förfarande enligt patentkravet 14, känneteck- n a t av att det organiska polyisocyanatet, polyetylenglykolen och den hydrofoba reaktanten bringas att reagera samtidigt.
16. Förfarande enligt patentkravet 14, känneteck- n a t av att den hydrofoba reaktanten har formeln R_ .3 (VI) R2-(-CH2CHO-^pQ där n är mellan 0 och ca 40; Ra är den monovalenta hydrofoba gruppen; varje R3 är individuellt väte eller Ci-s-alkyl; och Q är en funktionell grupp som är reaktiv med poly-. · . isocyanatet eller polyetylenglykolen. li 45 85591
17. Förfarande enligt patentkravet 16, känneteck- n a t av att n är 0.
18. Förfarande enligt patentkravet 16, känneteck- n a t av att Q är en aikylenglykolradikai eller alkenylradi-kal.
19. Förfarande enligt patentkravet 18, känneteck- n a t av att Q är OH -CHCH2OH.
20. Förfarande enligt patentkravet 18, känneteck- n a t av att Q är -CH=CH2.
21. Förfarande enligt patentkravet 19, känneteck- n a t av att man (1) bringar ett molöverskott av polyisocyanatet att reagera med polyetylenglykolen för att bilda en polyetylen- i glykol-diisocyanat-mellanprodukt med formeln ! 0=C = N-X—{—Y-X—Ηε*—N = C = 0 (VII) ! där b' är medeltalet av antalet polyetylenglykolrester per molekyl, X är polyisocyanatresten och Y är polyetylenglykol-' resten; varefter man (2) bringar polyetylenglykolmellanprodukten att reagera med den nämnda hydrofobreaktanten för att producera polyuretanet med den äterkommande strukturen C«2 S (VIII) ^°?HCH2-VR2 R3 där b' , £, n, R2, Ra, X och Y betecknar samma som ovan de-- finierats. 46 85591
22. Förfarande enligt patentkravet 19, känneteck-n a t av att man (1) bringar ett mol överskott av polyisocyanatet att reagera med den hydrofoba reaktanten för att bilda en hydro-fob-diisocyanat-mellanprodukt med formeln:
0-C.N-X-CHCH2-X-N«C«0 CH l 1 (IX) 1—f-OCHCH2-4^-R2 *3 där n, Ra och R3 betecknar samma som ovan definierats; och X är polyisocyanatresten; varefter man (2) bringar hydrofob-diisocyanatmellanprodukten att reagera med polyetylenglykolen för att producera polyuretanet med den aterkommande strukturen (VIII) som definierats i patentkravet 21.
23. Förfarande enligt patentkravet 19, känneteck-n a t av att man (1) bringar den hydrofoba reaktanten att reagera med (a) polyetylenglykolen eller (b) dess monomera ekvivalent som omfattar tillräckligt mänga mol av minst en oxialkylenglykol med formeln: R4 HOCHaCHOH .! där R« är väte eller Ci-3-alkyl för att bilda b mol av en diolmellanprodukt med formeln: H0-V3-t-j:HCH20 f-c f -Y4-OH LL *3 där c' är medeltalet av antalet monovalenta hydrofob-: : grupper per diolmellanprodukt; n, R2 och R3 betecknar samma som ovan definierats; och li 47 85591 Y3 och Υ« är rester av nämnda polyetylenglykol-eller oxialkylenreaktion; varefter man (2) bringar diolmellanprodukten att reagera med polyisocyanatet för att producera polyuretanet med den äter-kommande strukturen ?H2 <Χ) U-OCncB^Fj B3 där a, b, c' , n, Ra, Ra, X, Y3 och Y* betecknar samma som ovan definierats.
24. Förfarande enligt patentkravet 20, känneteck-n a t av att man (1) ympar den hydrofoba reaktanten pä polyetylen-glykolen för att bilda en diolmellanprodukt med formeln HO-Y^CHCHjO-^-Y^OH (χι) *2 där Ra betecknar samma som ovan definierats; £' är medeltalet av antalet ympningar som innehäller den monovalenta hydrofobgruppen; och Ys och Y« är rester an polyetylenglykolen; varefter man (2) bringar diolmellanprodukten att reagera med polyisocyanatet för att producera polyuretanet med den äter-kommande strukturen H-HY^CHCHjO-^Y^X-hr *2 där a, b, c' , Ra, X, Ys och Ye betecknar samma som ovan definierats. * ' ' l
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/561,472 US4496708A (en) | 1983-12-14 | 1983-12-14 | Water-soluble polyurethane comb polymer production |
| US56147283 | 1983-12-14 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI844942A0 FI844942A0 (fi) | 1984-12-13 |
| FI844942L FI844942L (fi) | 1985-06-15 |
| FI85591B true FI85591B (fi) | 1992-01-31 |
| FI85591C FI85591C (sv) | 1992-05-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI844942A FI85591C (sv) | 1983-12-14 | 1984-12-13 | Vattenlösliga polyuretankampolymerer samt deras framställning |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4496708A (sv) |
| EP (1) | EP0151748A1 (sv) |
| JP (2) | JPS60144317A (sv) |
| KR (1) | KR910000427B1 (sv) |
| AR (1) | AR241089A1 (sv) |
| AU (1) | AU579596B2 (sv) |
| BR (1) | BR8406376A (sv) |
| CA (1) | CA1227594A (sv) |
| DK (1) | DK598484A (sv) |
| FI (1) | FI85591C (sv) |
| NO (1) | NO162422C (sv) |
| OA (1) | OA07892A (sv) |
| ZA (1) | ZA849724B (sv) |
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| US4167502A (en) * | 1972-12-06 | 1979-09-11 | Rohm And Haas Company | Carboxylic polymeric thickeners |
| US3794608A (en) * | 1973-05-11 | 1974-02-26 | Dow Chemical Co | Aqueous coating compositions thickened by a terpolymer of an alkenyl aromatic compound,an unsaturated dicarboxylic acid,and an ether of vinyl benzyl alcohol and an oxyalkylated compound |
| DE2503872A1 (de) * | 1974-02-04 | 1975-10-30 | Ciba Geigy Ag | Perfluoralkylthiogruppen enthaltende polyurethane, verfahren zu ihrer herstellung und ihre verwendung |
| DE2457972C3 (de) * | 1974-12-07 | 1980-07-31 | Akzo Gmbh, 5600 Wuppertal | Anionische Polyurethane |
| US4138381A (en) * | 1975-04-14 | 1979-02-06 | E. I. Du Pont De Nemours And Company | Polymeric thickeners, processes for their preparation and uses thereof |
| US4079028A (en) * | 1975-10-03 | 1978-03-14 | Rohm And Haas Company | Polyurethane thickeners in latex compositions |
| EP0000137B1 (de) * | 1977-06-25 | 1982-03-24 | Hoechst Aktiengesellschaft | Polyglykolester, Verfahren zu ihrer Herstellung und ihre Verwendung als oberflächenaktive Mittel |
| JPS5480349A (en) * | 1977-12-06 | 1979-06-27 | Rohm & Haas | Polyurethane thickener for latex composition |
| US4169818A (en) * | 1978-04-17 | 1979-10-02 | Celanese Corporation | Mixture of hydroxypropylcellulose and poly(maleic anhydride/alkyl vinyl ether) as a hydrocolloid gelling agent |
| US4230844A (en) * | 1978-09-28 | 1980-10-28 | E. I. Du Pont De Nemours And Company | Processes for the preparation of polymeric thickeners and uses thereof |
| US4268641A (en) * | 1979-04-24 | 1981-05-19 | Union Carbide Corporation | Acrylic acid-acrylate copolymer thickening agents |
| JPS58104359A (ja) * | 1981-12-16 | 1983-06-21 | Hitachi Ltd | 混合気供給装置 |
| US4426485A (en) * | 1982-06-14 | 1984-01-17 | Union Carbide Corporation | Polymers with hydrophobe bunches |
-
1983
- 1983-12-14 US US06/561,472 patent/US4496708A/en not_active Expired - Lifetime
-
1984
- 1984-11-13 CA CA000467719A patent/CA1227594A/en not_active Expired
- 1984-12-12 AU AU36533/84A patent/AU579596B2/en not_active Ceased
- 1984-12-12 BR BR8406376A patent/BR8406376A/pt not_active IP Right Cessation
- 1984-12-13 FI FI844942A patent/FI85591C/sv not_active IP Right Cessation
- 1984-12-13 JP JP59261943A patent/JPS60144317A/ja active Granted
- 1984-12-13 DK DK598484A patent/DK598484A/da not_active Application Discontinuation
- 1984-12-13 OA OA58469A patent/OA07892A/xx unknown
- 1984-12-13 AR AR298939A patent/AR241089A1/es active
- 1984-12-13 ZA ZA849724A patent/ZA849724B/xx unknown
- 1984-12-13 NO NO845004A patent/NO162422C/no unknown
- 1984-12-13 EP EP84115351A patent/EP0151748A1/en not_active Ceased
-
1988
- 1988-06-23 KR KR1019890700339A patent/KR910000427B1/ko not_active Expired
-
1989
- 1989-03-16 JP JP1062336A patent/JPH07113051B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR850004775A (ko) | 1985-07-27 |
| AU3653384A (en) | 1985-06-20 |
| JPH07113051B2 (ja) | 1995-12-06 |
| FI85591C (sv) | 1992-05-11 |
| DK598484D0 (da) | 1984-12-13 |
| US4496708A (en) | 1985-01-29 |
| ZA849724B (en) | 1985-07-31 |
| JPS60144317A (ja) | 1985-07-30 |
| BR8406376A (pt) | 1985-10-08 |
| NO162422C (no) | 1989-12-27 |
| CA1227594A (en) | 1987-09-29 |
| DK598484A (da) | 1985-06-15 |
| AR241089A1 (es) | 1991-10-31 |
| FI844942A0 (fi) | 1984-12-13 |
| NO162422B (no) | 1989-09-18 |
| JPH0155654B2 (sv) | 1989-11-27 |
| AR241089A2 (es) | 1991-10-31 |
| FI844942L (fi) | 1985-06-15 |
| NO845004L (no) | 1985-06-17 |
| JPH0249021A (ja) | 1990-02-19 |
| OA07892A (fr) | 1986-11-20 |
| AU579596B2 (en) | 1988-12-01 |
| EP0151748A1 (en) | 1985-08-21 |
| KR910000427B1 (ko) | 1991-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: UNION CARBIDE CORPORATION |