JPS59193916A - 脂肪族と芳香族との混合ポリカルボジイミドの製法 - Google Patents
脂肪族と芳香族との混合ポリカルボジイミドの製法Info
- Publication number
- JPS59193916A JPS59193916A JP59031572A JP3157284A JPS59193916A JP S59193916 A JPS59193916 A JP S59193916A JP 59031572 A JP59031572 A JP 59031572A JP 3157284 A JP3157284 A JP 3157284A JP S59193916 A JPS59193916 A JP S59193916A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- range
- aliphatic
- diisocyanates
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 22
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 14
- -1 hardboard Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical group O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- 239000003431 cross linking reagent Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 abstract description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001718 carbodiimides Chemical class 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000004594 Masterbatch (MB) Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000007824 aliphatic compounds Chemical class 0.000 description 4
- 229940072049 amyl acetate Drugs 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZMFWEWMHABZQNB-UHFFFAOYSA-N 6-acetyloxyhexyl acetate Chemical compound CC(=O)OCCCCCCOC(C)=O ZMFWEWMHABZQNB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004908 Emulsion polymer Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QKUNKVYPGIOQNP-UHFFFAOYSA-N 4,8,11,14,17,21-hexachlorotetracosane Chemical compound CCCC(Cl)CCCC(Cl)CCC(Cl)CCC(Cl)CCC(Cl)CCCC(Cl)CCC QKUNKVYPGIOQNP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 241000533950 Leucojum Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- KAPCRJOPWXUMSQ-UHFFFAOYSA-N [2,2-bis[3-(aziridin-1-yl)propanoyloxymethyl]-3-hydroxypropyl] 3-(aziridin-1-yl)propanoate Chemical compound C1CN1CCC(=O)OCC(COC(=O)CCN1CC1)(CO)COC(=O)CCN1CC1 KAPCRJOPWXUMSQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241001251094 Formica Species 0.000 description 1
- 235000008612 Gnetum gnemon Nutrition 0.000 description 1
- 240000000018 Gnetum gnemon Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- 241000282330 Procyon lotor Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 102220468232 Uromodulin-like 1_R96D_mutation Human genes 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910021386 carbon form Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 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
- 239000011346 highly viscous material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UELAIMNOXLAYRW-UHFFFAOYSA-M sodium;1,4-dicyclohexyloxy-1,4-dioxobutane-2-sulfonate Chemical compound [Na+].C1CCCCC1OC(=O)C(S(=O)(=O)[O-])CC(=O)OC1CCCCC1 UELAIMNOXLAYRW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Organic Insulating Materials (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US469434 | 1983-02-24 | ||
| US06/469,434 US4487964A (en) | 1983-02-24 | 1983-02-24 | Method of making mixed aliphatic/aromatic polycarbodiimides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59193916A true JPS59193916A (ja) | 1984-11-02 |
| JPS6411051B2 JPS6411051B2 (OSRAM) | 1989-02-23 |
Family
ID=23863788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59031572A Granted JPS59193916A (ja) | 1983-02-24 | 1984-02-23 | 脂肪族と芳香族との混合ポリカルボジイミドの製法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4487964A (OSRAM) |
| EP (1) | EP0120305B1 (OSRAM) |
| JP (1) | JPS59193916A (OSRAM) |
| KR (1) | KR900008527B1 (OSRAM) |
| AT (1) | ATE21386T1 (OSRAM) |
| AU (1) | AU559037B2 (OSRAM) |
| CA (1) | CA1213394A (OSRAM) |
| DE (1) | DE3460449D1 (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021132474A1 (ja) | 2019-12-25 | 2021-07-01 | 日清紡ケミカル株式会社 | 水性樹脂用架橋剤組成物および水性樹脂組成物 |
| US12195637B2 (en) | 2019-03-05 | 2025-01-14 | Nisshinbo Chemical Inc. | Crosslinking agent for aqueous resin, liquid containing crosslinking agent for aqueous resin, and aqueous-resin composition |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820863A (en) * | 1986-03-31 | 1989-04-11 | Union Carbide Corporation | Surface active polycarbodiimides |
| US5108653A (en) * | 1986-03-31 | 1992-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Surface active polycarbodiimides and their dispersions |
| AR244271A1 (es) * | 1986-12-30 | 1993-10-29 | Union Carbide Corp | Una policarbodiimida tensioactiva. |
| US5352831A (en) * | 1987-09-02 | 1994-10-04 | Ciba-Geigy Corporation | Oligomeric cyanoguanidines |
| IT1230088B (it) * | 1989-05-26 | 1991-10-05 | Italiane Vernici Ind | Composizione di rivestimento a rapido indurimento. |
| JP2796385B2 (ja) * | 1989-12-22 | 1998-09-10 | ミネソタ マイニング アンド マニユフアクチユアリング カンパニー | 撥水撥油処理剤 |
| US5008363A (en) * | 1990-03-23 | 1991-04-16 | Union Carbide Chemicals And Plastics Technology Corporation | Low temperature active aliphatic aromatic polycarbodiimides |
| US5240811A (en) * | 1991-04-15 | 1993-08-31 | Ocg Microelectronic Materials, Inc. | Photogenerated polycarbodiimides from poly(tetrazole-5-thiones) and use in the preparation of coatings and deep-UV photoresists |
| US5276096A (en) * | 1991-08-28 | 1994-01-04 | Basf Corporation | Two package coating composition comprising a polycarbodimide with improved rheology control |
| JP3165971B2 (ja) * | 1991-12-26 | 2001-05-14 | 日清紡績株式会社 | ポリテトラメチルキシリレンカルボジイミド |
| US5352400A (en) * | 1992-04-29 | 1994-10-04 | E. I. Du Pont De Nemours And Company | Carbodiimides and processes therefor |
| JP3188959B2 (ja) * | 1992-08-10 | 2001-07-16 | 日清紡績株式会社 | ポリカルボジイミド樹脂の製造方法 |
| JP3438957B2 (ja) * | 1994-08-11 | 2003-08-18 | 日清紡績株式会社 | 補強材用の水性表面処理剤、該水性表面処理剤で処理された補強材及び補強材により強化された複合材 |
| US5936043A (en) | 1995-12-22 | 1999-08-10 | Rohm And Haas Company | Polymers crosslinkable with aliphatic polycarbodiimides |
| KR100304475B1 (ko) * | 1996-01-18 | 2001-11-22 | 야마모토 히데키 | 방향족폴리카보디이미드및이로부터제조된필름 |
| JP3518149B2 (ja) † | 1996-02-29 | 2004-04-12 | 日清紡績株式会社 | 水性プレコートメタル用塗料 |
| JP3393752B2 (ja) * | 1996-04-26 | 2003-04-07 | 日清紡績株式会社 | エステル基を有する樹脂用の耐加水分解安定剤及び該安定剤によるエステル基を有する樹脂の耐加水分解安定化方法 |
| US5885662A (en) † | 1997-01-31 | 1999-03-23 | Atoma International, Inc. | Decorative automotive interior trim articles with integral light stable polyurethane elastomer covering and process for making the same |
| US6362247B1 (en) | 2000-05-08 | 2002-03-26 | Rohm And Haas Company | Method of improving stability of aromatic polycarbodiimides |
| US6566437B2 (en) | 2000-06-05 | 2003-05-20 | Rohm And Haas Company | Wear-resistant coating composition and method of producing a coating |
| US7045571B2 (en) * | 2001-05-21 | 2006-05-16 | 3M Innovative Properties Company | Emulsion polymerization of fluorinated monomers |
| US6737489B2 (en) | 2001-05-21 | 2004-05-18 | 3M Innovative Properties Company | Polymers containing perfluorovinyl ethers and applications for such polymers |
| AU2002311389B2 (en) * | 2001-12-13 | 2008-01-31 | Rohm And Haas Company | Crosslinkable composition |
| US6890360B2 (en) | 2001-12-17 | 2005-05-10 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
| MXPA04011628A (es) * | 2002-05-24 | 2005-03-31 | 3M Innovative Properties Co | Composiciones fluoroquimicas que comprenden perfluoropolieter y un alargador para tratamiento de substratos fibrosos. |
| US7425279B2 (en) * | 2002-05-24 | 2008-09-16 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| EP1507814B1 (en) * | 2002-05-24 | 2007-11-21 | 3M Innovative Properties Company | Fluorochemical composition comprising a fluorinated polyether and treatment of a fibrous substrate therewith |
| EP1507916A1 (en) * | 2002-05-24 | 2005-02-23 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| JP4791369B2 (ja) * | 2003-11-12 | 2011-10-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | インクジェット・インク、インクセットおよび印刷の方法 |
| US7504523B2 (en) * | 2006-03-10 | 2009-03-17 | Basf Corporation | Uretonimine-modified isocyanate composition and method of forming the same |
| US7541397B2 (en) * | 2006-03-10 | 2009-06-02 | Basf Corporation | Uretonimine-modified isocyanate composition and method of forming the same |
| US20080116414A1 (en) * | 2006-11-22 | 2008-05-22 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| WO2008154421A1 (en) | 2007-06-08 | 2008-12-18 | 3M Innovative Properties Company | Blends of fluoroalkyl-containing ester oligomers with polydicarbodiimide(s) |
| WO2011109386A1 (en) * | 2010-03-02 | 2011-09-09 | Ppg Industries Ohio, Inc. | One-component, ambient curable waterborne coating compositions, related methods and coated substrates |
| ES2624297T3 (es) | 2012-11-28 | 2017-07-13 | Evonik Röhm Gmbh | Señalizaciones viales novedosas para el apoyo de la percepción del entorno de vehículos |
| DE102013206116A1 (de) | 2013-04-08 | 2014-10-09 | Evonik Industries Ag | Neuartige Straßenmarkierungen zur Unterstützung der Umfeldwahrnehmung von Fahrzeugen |
| CN108003313B (zh) * | 2017-12-21 | 2020-08-04 | 上海朗亿功能材料有限公司 | 一种嵌段型聚碳化二亚胺水性交联剂及其制备方法 |
| KR102219875B1 (ko) * | 2019-10-07 | 2021-02-24 | 공주대학교 산학협력단 | 소각용 액체 연료 분무 인젝터 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005726B (de) * | 1955-10-26 | 1957-04-04 | Bayer Ag | Stabilisierendes Mittel gegenueber den Einfluessen von Waerme und Feuchtigkeit in durch polysocyanate modifizierten Polyestermassen |
| US2853473A (en) * | 1956-08-27 | 1958-09-23 | Du Pont | Production of carbodiimides |
| NL272088A (OSRAM) * | 1960-12-02 | |||
| NL273087A (OSRAM) * | 1960-12-31 | |||
| DE1190176B (de) * | 1961-04-25 | 1965-04-01 | Bayer Ag | Verwendung von Carbodiimiden gemeinsam mit siliciumorganischen Verbindungen als stabilisierende Mittel in estergruppenhaltigen Polyurethanen |
| FR1469946A (fr) * | 1965-02-25 | 1967-02-17 | Bayer Ag | Procédé de préparation de carbodiimides |
| US3639353A (en) * | 1970-03-20 | 1972-02-01 | Goodrich Co B F | Polymers crosslinked with polycarbodiimides |
| US3929733A (en) * | 1974-10-02 | 1975-12-30 | Upjohn Co | Polycarbodiimides from 4,4{40 -methylenebis(phenyl isocyanate) and certain carbocyclic monoisocyanates |
| DE2536493A1 (de) * | 1975-08-16 | 1977-02-24 | Bayer Ag | Polymerisationsprodukte |
| DE2624198C2 (de) * | 1976-05-29 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Polymerisationsprodukte |
-
1983
- 1983-02-24 US US06/469,434 patent/US4487964A/en not_active Expired - Fee Related
-
1984
- 1984-02-03 CA CA000446741A patent/CA1213394A/en not_active Expired
- 1984-02-23 DE DE8484101922T patent/DE3460449D1/de not_active Expired
- 1984-02-23 AT AT84101922T patent/ATE21386T1/de active
- 1984-02-23 JP JP59031572A patent/JPS59193916A/ja active Granted
- 1984-02-23 KR KR1019840000874A patent/KR900008527B1/ko not_active Expired
- 1984-02-23 EP EP84101922A patent/EP0120305B1/en not_active Expired
- 1984-02-23 AU AU24864/84A patent/AU559037B2/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12195637B2 (en) | 2019-03-05 | 2025-01-14 | Nisshinbo Chemical Inc. | Crosslinking agent for aqueous resin, liquid containing crosslinking agent for aqueous resin, and aqueous-resin composition |
| WO2021132474A1 (ja) | 2019-12-25 | 2021-07-01 | 日清紡ケミカル株式会社 | 水性樹脂用架橋剤組成物および水性樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2486484A (en) | 1984-08-30 |
| JPS6411051B2 (OSRAM) | 1989-02-23 |
| AU559037B2 (en) | 1987-02-19 |
| EP0120305A1 (en) | 1984-10-03 |
| US4487964A (en) | 1984-12-11 |
| EP0120305B1 (en) | 1986-08-13 |
| KR850000484A (ko) | 1985-02-27 |
| CA1213394A (en) | 1986-10-28 |
| DE3460449D1 (en) | 1986-09-18 |
| ATE21386T1 (de) | 1986-08-15 |
| KR900008527B1 (ko) | 1990-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS59193916A (ja) | 脂肪族と芳香族との混合ポリカルボジイミドの製法 | |
| US3954684A (en) | Foam process using tertiary amine/quaternary ammonium salt catalyst | |
| US4587301A (en) | Method of using mixed aliphatic/aromatic polycarbodiimides | |
| DE3850475T2 (de) | Wässrige Polyurethan Dispersionen. | |
| JPH0570625B2 (OSRAM) | ||
| JPS62109813A (ja) | 水性ポリウレタン分散体 | |
| NO148817B (no) | Plastblanding for belegning eller stoeping inneholdende titanat-fosfittaddukter. | |
| JPS59187029A (ja) | ウオ−タ−ボ−ン樹脂の低温架橋 | |
| US5357021A (en) | Reactive carbodimide compositions | |
| US3211674A (en) | Polyurethane foam from hydroxylated tall oil | |
| US4143009A (en) | Polyurethane-epoxy casting resin | |
| US3644234A (en) | Method of preparing cellular polymers from organic polyisocyanates and polycarboxylic acid compounds | |
| US4225678A (en) | Foamed polyurethane materials with a bitumen and a hydroxy fatty oil | |
| JPS6253975A (ja) | ブロツク化ポリイソシアヌレ−ト | |
| JPS612721A (ja) | オルガノミネラル生成物の製法 | |
| US2877193A (en) | Stabilization of polyurethane reaction products | |
| SU862833A3 (ru) | Состав дл покрытий | |
| JPS6346212A (ja) | 一液型ウレタン樹脂組成物 | |
| JPS6172013A (ja) | 樹脂組成物 | |
| US3223678A (en) | Chain shortening of polycarbonate resins using monoethanolamine or morpholine as the shortening agent | |
| US4255527A (en) | Novel blowing agent for polymeric foam process | |
| US4011179A (en) | Continuous sulfur foam preparation using polyisocyanates | |
| JP2001031738A (ja) | 硬化性エポキシ樹脂組成物 | |
| JPH0415270B2 (OSRAM) | ||
| JPH0390090A (ja) | 新規イミノシラン |