NO127973B - - Google Patents
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- Publication number
- NO127973B NO127973B NO04056/68A NO405668A NO127973B NO 127973 B NO127973 B NO 127973B NO 04056/68 A NO04056/68 A NO 04056/68A NO 405668 A NO405668 A NO 405668A NO 127973 B NO127973 B NO 127973B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- fatty acid
- reaction
- reaction mixture
- foam
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 69
- 229930195729 fatty acid Natural products 0.000 claims description 69
- 239000000194 fatty acid Substances 0.000 claims description 69
- 150000004665 fatty acids Chemical class 0.000 claims description 65
- 229920005862 polyol Polymers 0.000 claims description 47
- 150000003077 polyols Chemical class 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 239000011496 polyurethane foam Substances 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 26
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- -1 nitrogen-containing polyol Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 6
- 229940043276 diisopropanolamine Drugs 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 150000004965 peroxy acids Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000006260 foam Substances 0.000 description 46
- 238000004519 manufacturing process Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 229920002635 polyurethane Polymers 0.000 description 15
- 239000004814 polyurethane Substances 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000005187 foaming Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 238000010640 amide synthesis reaction Methods 0.000 description 4
- 229910001651 emery Inorganic materials 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 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
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000011347 resin Chemical class 0.000 description 2
- 229920005989 resin Chemical class 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- KQIXMZWXFFHRAQ-UHFFFAOYSA-N 1-(2-hydroxybutylamino)butan-2-ol Chemical compound CCC(O)CNCC(O)CC KQIXMZWXFFHRAQ-UHFFFAOYSA-N 0.000 description 1
- QZEJJPSZCXBLAI-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCNCCO QZEJJPSZCXBLAI-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- XGZOMURMPLSSKQ-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)N(CCO)CCO XGZOMURMPLSSKQ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920006113 non-polar polymer Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C30/00—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process
- C23C30/005—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process on hard metal substrates
-
- 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
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/0058—≥50 and <150kg/m3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polyurethanes Or Polyureas (AREA)
- Fats And Perfumes (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4667167 | 1967-10-12 | ||
| GB4771568 | 1967-10-12 | ||
| GB8268/68A GB1247671A (en) | 1967-10-12 | 1968-02-20 | Polyurethane materials derived from fatty acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127973B true NO127973B (cs) | 1973-09-10 |
Family
ID=27255180
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04055/68A NO127972B (cs) | 1967-10-12 | 1968-10-11 | |
| NO04056/68A NO127973B (cs) | 1967-10-12 | 1968-10-11 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04055/68A NO127972B (cs) | 1967-10-12 | 1968-10-11 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US3637539A (cs) |
| AT (2) | AT297320B (cs) |
| BE (2) | BE722287A (cs) |
| CH (1) | CH553232A (cs) |
| CS (2) | CS158226B2 (cs) |
| DE (3) | DE1802500A1 (cs) |
| DK (2) | DK131945C (cs) |
| ES (2) | ES359102A1 (cs) |
| FI (2) | FI49314C (cs) |
| FR (2) | FR1588352A (cs) |
| GB (2) | GB1248919A (cs) |
| IE (2) | IE32410B1 (cs) |
| IL (2) | IL31634A (cs) |
| LU (2) | LU57048A1 (cs) |
| NL (2) | NL161471C (cs) |
| NO (2) | NO127972B (cs) |
| SE (1) | SE347596B (cs) |
| YU (1) | YU32764B (cs) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH14393A (en) * | 1973-02-08 | 1981-06-25 | Daiichi Seiyaku Co | Flame-resistant polyurethane foam and process for producing same |
| US4201847A (en) * | 1973-02-16 | 1980-05-06 | Bayer Aktiengesellschaft | Process of preparing foams with internal mold-release agents |
| DE2307589C3 (de) * | 1973-02-16 | 1984-11-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Schaumstoffen mit vorzüglichen Entformungseigenschaften |
| US3971764A (en) * | 1974-12-26 | 1976-07-27 | Akzona Incorporated | Process for producing a cationic polyurethane |
| FI57270C (fi) * | 1977-02-16 | 1980-07-10 | Vaeinoe Erae | Foerfarande foer framstaellning av laempliga polyuretanbelaeggningar foer metallplaot ur neutralaemnen av blandsaopa |
| US4094838A (en) * | 1977-06-03 | 1978-06-13 | The United States Of America As Represented By The Secretary Of Agriculture | Triglyceride oil-derived water-dispersible urethane resin coatings |
| DE2915458A1 (de) * | 1979-04-17 | 1980-10-30 | Basf Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| DE2915468A1 (de) * | 1979-04-17 | 1980-10-30 | Basf Ag | Verfahren zur herstellung urethangruppenhaltiger polyisocyanuratschaumstoffe |
| GB2058098B (en) * | 1979-06-11 | 1983-12-07 | Upjohn Co | Miscible fluorocarbon-polyol blends |
| US4246364A (en) * | 1980-02-19 | 1981-01-20 | The Upjohn Company | Process for polyisocyanurate foams based on an amide-diol blend |
| US4609513A (en) * | 1984-08-15 | 1986-09-02 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US4752637A (en) * | 1984-08-15 | 1988-06-21 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US4549005A (en) * | 1984-10-09 | 1985-10-22 | Ashland Oil, Inc. | Cured polymeric material prepared by reacting an azadioxabicyclooctane with a polyisocyanate in the presence of moisture |
| US4562240A (en) * | 1984-12-20 | 1985-12-31 | Ashland Oil, Inc. | Bicyclic amide acetal/polyol/polyisocyanate polymers |
| FI77676C (fi) * | 1986-01-22 | 1989-04-10 | Lohja Ab Oy | Foerfarande foer framstaellning av ett isocyanuratmodifierat polyuretanskum och medelst foerfarandet framstaellt polyuretanskum. |
| DE3641217A1 (de) * | 1986-12-03 | 1988-06-16 | Bayer Ag | Estergruppen- und urethangruppen-haltige bindemittel, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von ueberzuegen |
| EP0672697A1 (de) * | 1994-03-17 | 1995-09-20 | Bayer Ag | Verfahren zur Herstellung von Urethan-, Harnstoff- und Biuretgruppen aufweisenden Hartschaumstoffen und deren Verwendung |
| DE4409042A1 (de) * | 1994-03-17 | 1995-09-21 | Bayer Ag | Verfahren zur Herstellung von gegebenenfalls zellförmigen Polyurethanen und/oder Polyurethanharnstoffen |
| IT1280096B1 (it) * | 1995-10-06 | 1997-12-29 | Ediltec S R L | Schiuma poliuretanica |
| DE19603877C1 (de) * | 1996-02-03 | 1997-07-10 | Vetter Foerdertechnik Gmbh | Schäkel |
| US5910515A (en) * | 1997-03-24 | 1999-06-08 | Ediltec S.R.L. | Polyurethane foam |
| US6121398A (en) * | 1997-10-27 | 2000-09-19 | University Of Delaware | High modulus polymers and composites from plant oils |
| US6780908B1 (en) | 2000-06-21 | 2004-08-24 | E. I. Du Pont De Nemours And Company | Coating composition |
| US6433085B1 (en) * | 2000-06-21 | 2002-08-13 | E.I. Du Pont De Nemours And Company | Coating composition |
| US6846849B2 (en) | 2001-10-24 | 2005-01-25 | Temple-Inland Forest Products Corporation | Saccharide-based resin for the preparation of foam |
| WO2003035740A1 (en) | 2001-10-24 | 2003-05-01 | Temple-Inland Forest Products Corporation | Saccharide-based resin for the preparation of composite products |
| US20050159625A1 (en) * | 2004-01-19 | 2005-07-21 | Coates John S. | Alkoxylated amine and process therefor |
| CA2565313C (en) | 2004-05-07 | 2013-06-25 | Drexel University | Multi-modal vinyl ester resins |
| US8048949B1 (en) | 2004-05-07 | 2011-11-01 | Drexel University | Composite repair resins containing minimal hazardous air pollutants and volatile organic compound |
| EP1761580B1 (en) * | 2004-06-10 | 2008-04-30 | Dow Gloval Technologies Inc. | Polyurethane carpet backings made using fatty acid amide polyols |
| CN101039977B (zh) * | 2004-10-25 | 2011-10-12 | 陶氏环球技术有限责任公司 | 由含羟甲基的脂肪酸或这种脂肪酸的烷基酯制成的聚氨酯 |
| EP1913049B1 (en) * | 2005-08-03 | 2009-07-22 | Dow Global Technologies Inc. | Polyurethanes made from hydroxyl-containing fatty acid amides |
| JP2009513461A (ja) * | 2005-10-27 | 2009-04-02 | オーチス エレベータ カンパニー | 複数のポリマ構成物を備えたジャケットを有するエレベータ荷重支持アッセンブリ |
| MY144354A (en) * | 2005-11-08 | 2011-09-15 | Malaysian Palm Oil Board Mpob | A process for the production of a polyol monomer |
| AR064261A1 (es) * | 2006-11-16 | 2009-03-25 | Cargill Inc | Espumas poliuretanicas viscoelasticas que comprenden polioles de aceite natural oligomerico amidado o transesterificado |
| US8097739B2 (en) * | 2007-04-18 | 2012-01-17 | BioBases Technologies, LLC | Process for the manufacture of natural oil hydroxylates |
| DE102007055489B4 (de) | 2007-11-21 | 2019-07-11 | Mcpu Polymer Engineering Llc | Polyole aus Pflanzenölen und Verfahren zur Umwandlung |
| US20090143257A1 (en) * | 2007-12-03 | 2009-06-04 | Ling Kong Teng | Methods and Compositions for Controlling Water Production |
| WO2012006282A1 (en) | 2010-07-08 | 2012-01-12 | Dow Global Technologies Llc | Improved polyurethane sealing foam compositions plasticized with fatty acid esters |
| DE102011007468A1 (de) | 2011-04-15 | 2012-10-18 | Evonik Goldschmidt Gmbh | Zusammensetzung, enthaltend spezielle Carbamat-artige Verbindungen, geeignet zur Herstellung von Polyurethanschäumen |
| DE102011007479A1 (de) | 2011-04-15 | 2012-10-18 | Evonik Goldschmidt Gmbh | Zusammensetzung, enthaltend spezielle Amide und organomodifizierte Siloxane, geeignet zur Herstellung von Polyurethanschäumen |
| WO2012154393A2 (en) | 2011-05-12 | 2012-11-15 | Dow Global Technologies Llc | Stabilizer polymerization process and process for making polymer polyols |
| PL2726544T3 (pl) | 2011-06-29 | 2017-08-31 | Dow Global Technologies Llc | Sposób wytwarzania kompozytów pianek organicznych zawierających cząstki aerożelu |
| US9120896B2 (en) * | 2012-09-28 | 2015-09-01 | Elevance Renewable Sciences, Inc. | Polymers containing metathesized natural oil derivatives |
| WO2014055282A1 (en) | 2012-10-05 | 2014-04-10 | Dow Global Technologies Llc | Macromer and process for making polymer polyols |
| DE102013217395A1 (de) | 2013-09-02 | 2015-03-05 | Evonik Industries Ag | Verwendung von Mischungen organofunktionell modifizierter Polysiloxane mit Amiden bei der Herstellung von Polyurethanweichschäumen |
| DE102013226575B4 (de) | 2013-12-19 | 2021-06-24 | Evonik Operations Gmbh | Zusammensetzung, geeignet zur Herstellung von Polyurethanschäumen, enthaltend mindestens einen ungesättigten Fluorkohlenwasserstoff oder ungesättigten Fluorkohlenwasserstoff als Treibmittel, Polyurethanschäume, Verfahren zu deren Herstellung und deren Verwendung |
| EP2886591A1 (de) | 2013-12-19 | 2015-06-24 | Evonik Industries AG | Zusammensetzung, geeignet zur Herstellung von Polyurethanschäumen, enthaltend mindestens ein Nukleierungsmittel |
| JP6936810B2 (ja) | 2016-03-31 | 2021-09-22 | ダウ グローバル テクノロジーズ エルエルシー | 単分散分散ポリマー粒子を有するポリマーポリオールを作製するプロセス |
| JP7788382B2 (ja) | 2020-01-06 | 2025-12-18 | ダウ グローバル テクノロジーズ エルエルシー | ポリマーポリオールを作製するためのマクロマー及びプロセス |
| EP4299656A1 (de) * | 2022-07-01 | 2024-01-03 | Evonik Operations GmbH | Herstellung von propoxylierten benzoldicarbonsäureamiden und dem entsprechenden polyurethanschaum |
| CN115368532B (zh) * | 2022-09-01 | 2023-08-08 | 安徽农业大学 | 一种交联热固型聚氨酯弹性体及其制备方法 |
-
0
- DE DENDAT1248919D patent/DE1248919B/de active Pending
-
1967
- 1967-10-12 GB GB47716/68A patent/GB1248919A/en not_active Expired
-
1968
- 1968-02-20 GB GB8268/68A patent/GB1247671A/en not_active Expired
- 1968-10-04 US US765027A patent/US3637539A/en not_active Expired - Lifetime
- 1968-10-07 DK DK481668A patent/DK131945C/da active
- 1968-10-07 DK DK481768AA patent/DK133816B/da unknown
- 1968-10-07 US US765641A patent/US3637540A/en not_active Expired - Lifetime
- 1968-10-08 IE IE1201/68A patent/IE32410B1/xx unknown
- 1968-10-08 IE IE1200/68A patent/IE32893B1/xx unknown
- 1968-10-09 LU LU57048D patent/LU57048A1/xx unknown
- 1968-10-09 LU LU57049D patent/LU57049A1/xx unknown
- 1968-10-09 AT AT984268A patent/AT297320B/de not_active IP Right Cessation
- 1968-10-11 AT AT994668A patent/AT297321B/de not_active IP Right Cessation
- 1968-10-11 NO NO04055/68A patent/NO127972B/no unknown
- 1968-10-11 CS CS702468A patent/CS158226B2/cs unknown
- 1968-10-11 DE DE19681802500 patent/DE1802500A1/de active Pending
- 1968-10-11 YU YU2376/68A patent/YU32764B/xx unknown
- 1968-10-11 ES ES359102A patent/ES359102A1/es not_active Expired
- 1968-10-11 CH CH1526768A patent/CH553232A/xx not_active IP Right Cessation
- 1968-10-11 SE SE13775/68A patent/SE347596B/xx unknown
- 1968-10-11 CS CS7023A patent/CS174764B2/cs unknown
- 1968-10-11 DE DE19681802503 patent/DE1802503A1/de active Pending
- 1968-10-11 NO NO04056/68A patent/NO127973B/no unknown
- 1968-10-11 ES ES359104A patent/ES359104A1/es not_active Expired
- 1968-10-14 FR FR1588352D patent/FR1588352A/fr not_active Expired
- 1968-10-14 FI FI682906A patent/FI49314C/fi active
- 1968-10-14 FR FR1588353D patent/FR1588353A/fr not_active Expired
- 1968-10-14 FI FI682907A patent/FI49727C/fi active
- 1968-10-14 NL NL6814676.A patent/NL161471C/xx active
- 1968-10-14 BE BE722287D patent/BE722287A/xx unknown
- 1968-10-14 NL NL6814677A patent/NL6814677A/xx unknown
- 1968-10-14 BE BE722285D patent/BE722285A/xx unknown
-
1969
- 1969-02-16 IL IL31634A patent/IL31634A/en unknown
- 1969-02-16 IL IL31633A patent/IL31633A/en unknown
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