KR100774086B1 - 아실우레아 및 아실우레아를 포함하는 조성물의 합성 - Google Patents
아실우레아 및 아실우레아를 포함하는 조성물의 합성 Download PDFInfo
- Publication number
- KR100774086B1 KR100774086B1 KR1020067012662A KR20067012662A KR100774086B1 KR 100774086 B1 KR100774086 B1 KR 100774086B1 KR 1020067012662 A KR1020067012662 A KR 1020067012662A KR 20067012662 A KR20067012662 A KR 20067012662A KR 100774086 B1 KR100774086 B1 KR 100774086B1
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- composition
- acids
- functional groups
- strong acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 150000007945 N-acyl ureas Chemical class 0.000 title claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 title abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 86
- 239000000178 monomer Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 40
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000007513 acids Chemical class 0.000 claims abstract description 26
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 22
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 22
- 125000000524 functional group Chemical group 0.000 claims description 32
- -1 aromatic sulfonic acids Chemical class 0.000 claims description 31
- 239000012948 isocyanate Substances 0.000 claims description 29
- 150000002513 isocyanates Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000012429 reaction media Substances 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 150000003009 phosphonic acids Chemical class 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 23
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 235000019260 propionic acid Nutrition 0.000 description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical group [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical group 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000003973 paint Substances 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
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003573 thiols Chemical group 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
- GNDOBZLRZOCGAS-JTQLQIEISA-N 2-isocyanatoethyl (2s)-2,6-diisocyanatohexanoate Chemical compound O=C=NCCCC[C@H](N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-JTQLQIEISA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RVQUQYAITLEMNM-UHFFFAOYSA-N C(CCCCCN=C=O)N=C=O.CC(CCCCN=C=O)N=C=O Chemical compound C(CCCCCN=C=O)N=C=O.CC(CCCCN=C=O)N=C=O RVQUQYAITLEMNM-UHFFFAOYSA-N 0.000 description 1
- AHWDQDMGFXRVFB-UHFFFAOYSA-N CN(C(N(C)C(N1C)=O)=O)C1=O Chemical compound CN(C(N(C)C(N1C)=O)=O)C1=O AHWDQDMGFXRVFB-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002735 metacrylic acids Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002023 wood Substances 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
- C08G18/08—Processes
- C08G18/16—Catalysts
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret 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
- C08G18/08—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
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims (28)
- 둘 이상의 이소시아네이트 관능기를 포함하는 유도체를 포함하는 "출발" 조성물에, 하나 이상의 산은 강산 (pKa ≤ 3)이고 또 다른 하나 이상의 산은 중간산 (3 ≤ pKa ≤ 6)인 둘 이상의 산을 50℃ 이상의 온도에서 작용시키는 것을 특징으로 하는, 아실우레아를 포함하는 폴리이소시아네이트 조성물의 합성 방법.
- 제1항에 있어서, 하나 이상의 이소시아네이트 유도체가 단량체인 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 단량체 유도체가 상기 출발 조성물의 1/3 중량 이상을 나타내는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 단량체 유도체 또는 단량체 유도체들이 상기 출발 조성물의 90 중량% 이상을 나타내는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 단량체 유도체 또는 단량체 유도체 중 하나 이상이 적어도 부분적으로 지방족인 것임을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 상기 폴리이소시아네이트 조성물이 뷰렛 관능기를 포함하는 유도체를 포함하고, 상기 출발 조성물이 아민 또는 아민 생성 반응물에 추가로 접촉하게 되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 상기 폴리이소시아네이트 조성물이 뷰렛 관능기를 포함하는 유도체를 포함하고, 상기 출발 조성물이 아민 또는 아민 생성 반응물에 접촉하게 되며, (생성되는 또는 도입되는) 아민 대 총 단량체의 몰수로 표현되는 몰비가 1/2 내지 1/50의 폐쇄 범위 (즉, 한계를 포함함) 내에서 선택되는 것을 특징으로 하는 방법.
- 제6항에 있어서, 상기 출발 조성물이 상기 중간산(들) 및 강산(들)의 존재하에서 물과 접촉하게 되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 강산이 지방족 또는 방향족 설폰산, 카르복실-포스폰산을 포함하는 포스폰산, 인산에스테르 또는 퍼할로알칸산으로부터 선택되는 것임을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 중간산이 지방족 또는 방향족 카르복실산으로부터 선택되는 것임을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 중간산(들)이 전구체의 형태로 반응 매질에 적어도 부분적으로 도입되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 강산(들)이 전구체의 형태로 반응 매질에 적어도 부분적으로 도입되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 하나 이상의 중간산이 하나 이상의 강산과 1 pK 단위 이상 차이가 나는 것임을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 강산(들)의 함량이, 당량으로 표현되는 총 강산 관능기 대 몰수로 표현되는 총 단량체의 몰비가 0.1‰ 이상이도록 선택되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 강산(들)의 함량이, 당량으로 표현되는 총 강산 관능기 대 몰수로 표현되는 총 단량체의 몰비가 2% 이하이도록 선택되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 중간산(들)의 함량이, 당량으로 표현되는 총 중간산 관능기 대 몰수로 표현되는 총 단량체의 몰비가 2‰ 이상이도록 선택되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 중간산(들)의 함량이, 당량으로 표현되는 총 중간산 관능기 대 몰수로 표현되는 총 단량체의 몰비가 10% 이하이도록 선택되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 상기 강산이 희석된 형태로 도입되는 것을 특징으로 하는 방법.
- 제18항에 있어서, 상기 강산이 물에 희석되는 것을 특징으로 하는 방법.
- 제19항에 있어서, 상기 강산이 C1 내지 C14 알콜에 희석되는 것을 특징으로 하는 방법.
- 제20항에 있어서, 상기 강산이 상기 중간산에 희석되는 것을 특징으로 하는 방법.
- 다섯 개 디아미노 단위 이하의 아실우레아 1 중량% 이상 및 실제 뷰렛 단위를 포함하는 화합물 5% 이상을 포함하는 이소시아네이트 조성물.
- 제22항에 있어서, 모노아실우레아를 1% 이상 포함하는 것을 특징으로 하는 조성물.
- 제22항 또는 제23항에 있어서, 이관능성 이상의 산에 대응하는 디아실우레아를 2% 이상 포함하는 것을 특징으로 하는 조성물.
- 제22항 또는 제23항에 있어서, 실제 뷰렛을 10 중량% 이상 포함하는 것을 특징으로 하는 조성물.
- 제22항 또는 제23항에 있어서, 실제 뷰렛을 4/5 중량 이하 포함하는 것을 특징으로 하는 조성물.
- 제22항 또는 제23항에 있어서, 모노아실우레아 (분자) 대 여섯 개 디아미노 단위 이상의 올리고머의 중량비가 2% 이상인 것을 특징으로 하는 조성물.
- 제22항 또는 제23항에 있어서, 모노아실우레아 (분자) 대 여섯 개 디아미노 단위 이상의 올리고머의 중량비가 50% 이하인 것을 특징으로 하는 조성물.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0315409A FR2864534B1 (fr) | 2003-12-24 | 2003-12-24 | Synthese d'acylurees et composition comportant des acylurees |
FR0315409 | 2003-12-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20060108730A KR20060108730A (ko) | 2006-10-18 |
KR100774086B1 true KR100774086B1 (ko) | 2007-11-06 |
Family
ID=34639615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020067012662A KR100774086B1 (ko) | 2003-12-24 | 2004-12-16 | 아실우레아 및 아실우레아를 포함하는 조성물의 합성 |
Country Status (10)
Country | Link |
---|---|
US (2) | US20070106048A1 (ko) |
EP (1) | EP1697438B1 (ko) |
JP (1) | JP4884233B2 (ko) |
KR (1) | KR100774086B1 (ko) |
CN (1) | CN100569824C (ko) |
AT (1) | ATE500286T1 (ko) |
DE (1) | DE602004031668D1 (ko) |
FR (1) | FR2864534B1 (ko) |
PL (1) | PL1697438T3 (ko) |
WO (1) | WO2005070882A2 (ko) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2750308A1 (fr) * | 1996-04-11 | 1998-01-02 | Exal Diffusion | Verre a degustation pour alcools tels que les eaux de vie, les spiritueux et les liqueurs |
DE10110437A1 (de) * | 2001-03-05 | 2002-09-19 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten durch Umsetzung von Carbonsäuren mit Isocyanaten, die nach diesem Verfahren hergestellten Produkte und deren Verwendung in Polyurethankunststoffen |
FR2864534B1 (fr) | 2003-12-24 | 2006-02-17 | Rhodia Chimie Sa | Synthese d'acylurees et composition comportant des acylurees |
JP5476962B2 (ja) * | 2009-12-09 | 2014-04-23 | 日本ポリウレタン工業株式会社 | アシルウレア変性ポリイソシアネート組成物の製造方法 |
JP2011136912A (ja) * | 2009-12-25 | 2011-07-14 | Nippon Polyurethane Ind Co Ltd | アシルウレア変性ポリイソシアネート組成物の製造方法 |
EP2998331A1 (en) * | 2014-09-17 | 2016-03-23 | Construction Research & Technology GmbH | A curable organic polymer comprising at least one acylurea unit, its preparation and use |
WO2021142570A1 (zh) * | 2020-01-13 | 2021-07-22 | 万华化学集团股份有限公司 | 一种储存稳定的缩二脲多异氰酸酯的制备方法 |
CN112250835B (zh) * | 2020-09-14 | 2022-03-11 | 万华化学(宁波)有限公司 | 一种制备无色多异氰酸酯组合物的方法 |
CN114539508B (zh) * | 2020-11-25 | 2023-05-30 | 万华化学集团股份有限公司 | 一种改善水分散性的低粘多异氰酸酯组合物 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230778B (de) * | 1965-05-24 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten |
GB1515523A (en) * | 1974-07-30 | 1978-06-28 | Bayer Ag | Process for the production of polyisocyanates |
US4625052A (en) | 1984-01-31 | 1986-11-25 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates which have a biuret structure |
EP1238993A1 (de) * | 2001-03-05 | 2002-09-11 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten durch Umsetzung von Carbonsäuren mit Isocyanaten, die nach diesem Verfahren hergestellten Produkte und deren Verwendung in Polyurethankunststoffen |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1229067B (de) * | 1964-01-11 | 1966-11-24 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten |
US4077989A (en) * | 1974-07-30 | 1978-03-07 | Bayer Aktiengesellschaft | Process for the production of modified polyisocyanates |
DE2641448A1 (de) * | 1976-09-15 | 1978-03-16 | Bayer Ag | Verfahren zur herstellung von urethan- und biuretgruppen enthaltenden polyisocyanaten |
DE3247350A1 (de) * | 1982-12-22 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hydantoinestern |
DE10007820A1 (de) * | 2000-02-21 | 2001-08-23 | Bayer Ag | Acylharnstoffgruppen enthaltende Polyisocyanatgemische |
FR2864534B1 (fr) | 2003-12-24 | 2006-02-17 | Rhodia Chimie Sa | Synthese d'acylurees et composition comportant des acylurees |
-
2003
- 2003-12-24 FR FR0315409A patent/FR2864534B1/fr not_active Expired - Fee Related
-
2004
- 2004-12-16 KR KR1020067012662A patent/KR100774086B1/ko active IP Right Grant
- 2004-12-16 AT AT04816402T patent/ATE500286T1/de not_active IP Right Cessation
- 2004-12-16 WO PCT/FR2004/003262 patent/WO2005070882A2/fr not_active Application Discontinuation
- 2004-12-16 CN CNB2004800372051A patent/CN100569824C/zh active Active
- 2004-12-16 PL PL04816402T patent/PL1697438T3/pl unknown
- 2004-12-16 DE DE602004031668T patent/DE602004031668D1/de active Active
- 2004-12-16 US US10/582,438 patent/US20070106048A1/en not_active Abandoned
- 2004-12-16 JP JP2006543589A patent/JP4884233B2/ja active Active
- 2004-12-16 EP EP04816402A patent/EP1697438B1/fr active Active
-
2010
- 2010-03-01 US US12/714,873 patent/US8158817B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230778B (de) * | 1965-05-24 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten |
GB1515523A (en) * | 1974-07-30 | 1978-06-28 | Bayer Ag | Process for the production of polyisocyanates |
US4625052A (en) | 1984-01-31 | 1986-11-25 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates which have a biuret structure |
EP1238993A1 (de) * | 2001-03-05 | 2002-09-11 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten durch Umsetzung von Carbonsäuren mit Isocyanaten, die nach diesem Verfahren hergestellten Produkte und deren Verwendung in Polyurethankunststoffen |
Also Published As
Publication number | Publication date |
---|---|
EP1697438B1 (fr) | 2011-03-02 |
FR2864534B1 (fr) | 2006-02-17 |
JP2007513195A (ja) | 2007-05-24 |
ATE500286T1 (de) | 2011-03-15 |
DE602004031668D1 (de) | 2011-04-14 |
CN1894300A (zh) | 2007-01-10 |
WO2005070882A3 (fr) | 2006-03-09 |
WO2005070882A2 (fr) | 2005-08-04 |
EP1697438A2 (fr) | 2006-09-06 |
US20070106048A1 (en) | 2007-05-10 |
JP4884233B2 (ja) | 2012-02-29 |
PL1697438T3 (pl) | 2011-06-30 |
KR20060108730A (ko) | 2006-10-18 |
CN100569824C (zh) | 2009-12-16 |
US8158817B2 (en) | 2012-04-17 |
FR2864534A1 (fr) | 2005-07-01 |
US20100216966A1 (en) | 2010-08-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8158817B2 (en) | Synthesis of acylureas and composition comprising acylureas | |
US4160080A (en) | Process for the preparation of allophanates which contain isocyanate groups | |
US8173742B2 (en) | Synthesis of biurets and isocyanates with alkoxysilane functions, formulations containing same and use thereof | |
WO1999011690A1 (en) | Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings | |
CA2162832A1 (en) | Polyisocyanates containing allophanate groups | |
JP4234997B2 (ja) | 高官能価の低粘度ポリイソシアネート組成物及びその製造方法 | |
JP2008512519A (ja) | 乳化性ポリイソシアネート | |
CA2352688A1 (en) | Process for preparing low-odor and storage-stable monomer-containing polyisocyanurates from isophorone diisocyanate | |
EP1670840B1 (en) | Process for making amide acetals | |
JP3729857B2 (ja) | ビウレット基含有ポリイソシアネートの製法 | |
US8039574B2 (en) | Method for the preparation of low-viscosity (poly) isocyanates | |
EP0394058B1 (en) | Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof | |
US5925711A (en) | Polyamines and their use in aqueous coating compositions | |
JP2005520895A (ja) | 高い官能価を有する低粘度ポリイソシアネート組成物及びその製造方法 | |
CA2169226A1 (en) | Blocked polyisocyanates, process for their preparation, and coating materials and coating systems produced therefrom | |
JP2000038436A (ja) | 低温解離ブロックイソシアネート及びこれを含有する塗料 | |
US5663274A (en) | Heat-curable compositions based on cyclic isocyanate addition products | |
US5726273A (en) | Heat-curable compositions based on cyclic isocyanate addition reproducts | |
JP3419604B2 (ja) | 変性ポリイソシアネート混合物の製造方法 | |
JPH0959244A (ja) | ジイソシアネート化合物の反応促進方法および組成物 | |
RU2479597C1 (ru) | Способ получения фторсодержащего форполимера с изоцианатными группами | |
RU2479595C1 (ru) | Способ получения фторсодержащего форполимера с изоцианатными группами | |
US20240018097A1 (en) | Process for preparing a polyisocyanate, polyisocyanate, its use and polyaddition products prepared therefrom | |
JPH03143916A (ja) | エポキシウレタン樹脂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20121009 Year of fee payment: 6 |
|
FPAY | Annual fee payment |
Payment date: 20131011 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20141008 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20151006 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20161021 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20171020 Year of fee payment: 11 |