JP2007527942A - チオカルバミド酸エステル基を有するカルボジイミド - Google Patents
チオカルバミド酸エステル基を有するカルボジイミド Download PDFInfo
- Publication number
- JP2007527942A JP2007527942A JP2007502246A JP2007502246A JP2007527942A JP 2007527942 A JP2007527942 A JP 2007527942A JP 2007502246 A JP2007502246 A JP 2007502246A JP 2007502246 A JP2007502246 A JP 2007502246A JP 2007527942 A JP2007527942 A JP 2007527942A
- Authority
- JP
- Japan
- Prior art keywords
- group
- thiocarbamide
- polymer
- carbodiimide
- groups
- 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
- 150000001718 carbodiimides Chemical class 0.000 title claims description 35
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 72
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims description 36
- 229920000642 polymer Polymers 0.000 claims description 35
- -1 mercapto compound Chemical class 0.000 claims description 32
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 21
- 230000001070 adhesive effect Effects 0.000 claims description 16
- 239000000853 adhesive Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 239000004815 dispersion polymer Substances 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003010 ionic group Chemical group 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 239000006185 dispersion Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920003009 polyurethane dispersion Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- HIUQIUQSEYDPNQ-YFKPBYRVSA-N (2s)-6-amino-2-(phosphonoamino)hexanoic acid Chemical class NCCCC[C@@H](C(O)=O)NP(O)(O)=O HIUQIUQSEYDPNQ-YFKPBYRVSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
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- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- DMADTXMQLFQQII-UHFFFAOYSA-N 1-decyl-4-ethenylbenzene Chemical compound CCCCCCCCCCC1=CC=C(C=C)C=C1 DMADTXMQLFQQII-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- LYDHLGJJJAWBDY-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatocyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(N=C=O)CCC1C(C)(C)C1CCC(N=C=O)CC1 LYDHLGJJJAWBDY-UHFFFAOYSA-N 0.000 description 1
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- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- YJSSCAJSFIGKSN-UHFFFAOYSA-N hex-1-en-2-ylbenzene Chemical compound CCCCC(=C)C1=CC=CC=C1 YJSSCAJSFIGKSN-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 229960004635 mesna Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical class CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 230000007704 transition Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/08—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
-
- 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
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
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- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/765—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
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Abstract
Description
a)少なくとも1個のイソシアナート基を有するカルボジイミド、
b)少なくとも1個のメルカプト基を有するメルカプト化合物及び
c)場合により、イソシアナート基又はイソシアナートと反応性の基を有する別の化合物
の反応により好ましくは得ることができる。
メルカプト酢酸、2−及び3−メルカプトプロピオン酸、メルカプトコハク酸、メルカプトエタンスルホン酸、2−及び3−メルカプトプロパンスルホン酸。
I.成分(a)のイソシアナート基の一部をカルボジイミド化することによって、末端イソシアナート基を有するカルボジイミドを製造し、かつ
II.工程Iにより製造された末端イソシアナート基を有する化合物を、成分(b)及び場合により成分(c)と反応させる
ことによって、行われる。
IIa)炭素原子4〜30個を有するジイソシアナート、
IIb)以下のジオール
IIb1)前記ジオール(IIb)の全量に対して、500〜5000の分子量を有するジオール10〜100mol%、及び
IIb2)前記ジオールの全量に対して、60〜500g/molの分子量を有するジオール0〜90mol%、
IIc)モノマー(IIa)及び(IIb)とは異なり、少なくとも1個のイソシアナート基又はイソシアナート基に対して反応性の少なくとも1個の基を有しており、さらにまた少なくとも1個の親水性基又は1個の潜在的な親水性基を有するモノマー、それにより、前記ポリウレタンの水分散性が引き起こされる、
IId)場合により、モノマー(IIa)〜(IIc)とは異なり、アルコール性ヒドロキシル基、第一級又は第二級アミノ基又はイソシアナート基である反応性基を有する別の多価化合物、及び
IIe)場合により、モノマー(IIa)〜(IId)とは異なり、アルコール性ヒドロキシル基、第一級又は第二級アミノ基又はイソシアナート基である反応性基を有する一価化合物
から構成されている。
A)イソシアナート基のモル量及び
B)ヒドロキシル基のモル量及びイソシアナートと付加反応において反応することができる官能基のモル量からなる総和
である。極めて特に好ましくは比A:Bはできるだけほぼ1:1である。
IIIa)C1−〜C20−アルキル(メタ)アクリレート、炭素原子を20個まで有しているカルボン酸のビニルエステル、炭素原子を20個まで有するビニル芳香族化合物、エチレン系不飽和ニトリル、ハロゲン化ビニル及び炭素原子2〜8個及び二重結合1又は2個を有する脂肪族炭化水素から選択される主モノマー30〜100質量%、
IIIb) オレフィン系二重結合1個を有するカルボン酸0〜20質量%、好ましくは0.01〜20質量%及び
IIIc) (IIIa)及び(IIIb)とは異なるラジカル重合性モノマー0〜20質量%
から構成されている。
1.親水性カルボジイミド
1.1.チオカルバミド酸エステル基を有する親水性カルボジイミドの製造(本発明による)
7.8質量%のNCO含量を有し、TMXDIからなるNCOを末端基とするカルボジイミド471gをアセトン800g中に溶解させ、45℃に加熱した。これに、撹拌しながらNaOH 40g、メルカプト酢酸73.7g、水320g及びアセトン200gの混合物を添加した。撹拌6min後に水700gで希釈し、アセトンを真空中で除去した。
7.8質量%のNCO含量を有し、TMXDIからなるNCOを末端基とするカルボジイミド471gをアセトン800g中に溶解させ、45℃に加熱した。これに、撹拌しながら、NaOH 40g、グリシン60.0g、水320g及びアセトン200gの混合物を添加した。撹拌6min後に水700gで希釈し、アセトンを真空中で除去した。
省略形:
DMPA:ジメチロールプロピオン酸
DBTL:ジブチルスズジラウレート
IPDI:イソホロンジイソシアナート。
熱ラミネート接着剤としての試験のために、ポリウレタン分散液100部をAirflex EP 17 100部(酢酸ビニル及びエチレンからなるコポリマーの分散液)及び例1.1.及び1.2.からの架橋剤10部と混合した。前記混合物を、ABSからなる自動車(Kfz)成形部材上へ施与し、23℃で1h乾燥させた。乾燥後に、加熱プレス中で工業用自動車ラミネート用の市販のPVCシートをフィルム温度60℃及び1barで積層する。
a)はく離強さ:
常用の引張試験機を用いる100℃でのローラーはく離試験、はく離角90゜、はく離速度100mm/min。はく離力はN/50mmで測定される。
PVCシート及びABS成形部材からなる試験すべきラミネートを、PVCシートと水平に、下へ向かって枠に張り、かつ自由な接着されていないPVC端部上に300gのおもりを取り付けて、前記シートをおもりの下でABS上の接着位置まで垂直に下へ向かって屈曲させた。試験体を80℃に加熱し、かつ前記シートが接着の開始から出発してABSからはがれた距離を測定した(記載[mm])。
チオカルバミド酸エステル基を有するカルボジイミド:34N/50mm
尿素基を有するカルボジイミド:24N/50mm
さらに熱安定性を決定した。
チオカルバミド酸エステル基を有するカルボジイミド(例1.1.、本発明による):4mm
尿素基を有するカルボジイミド(例1.2.、本発明によらない):13mm
Claims (17)
- 付加的に親水性基を有している、請求項1記載のチオカルバミド。
- 親水性基がイオン性基又は非イオン性の親水性基から選択されている、請求項1又は2記載のチオカルバミド。
- 非イオン性基がポリアルキレンオキシド基である、請求項1から3までのいずれか1項記載のチオカルバミド。
- 前記化合物が、
a)少なくとも1個のイソシアナート基を有するカルボジイミド、
b)少なくとも1個のメルカプト基を有するメルカプト化合物及び
c)場合により、イソシアナート基又はイソシアナートと反応性の基を有する別の化合物
の反応により得ることができる、請求項1から4までのいずれか1項記載のチオカルバミド。 - カルボジイミドa)が、脂肪族又は芳香脂肪族のC4〜C20ポリイソシアナートから誘導されている、請求項5記載のチオカルバミド。
- メルカプト化合物b)が、少なくとも1個のメルカプト基に加えて、少なくとも1個の親水性基を有している、請求項5又は6記載のチオカルバミド。
- 平均してカルボジイミド基1〜20個及びチオカルバミド酸エステル基1〜4個を有している、請求項1から7までのいずれか1項記載のチオカルバミド。
- チオカルバミド1kg当たり平均して親水性基0.01〜2molを有している、請求項1から8までのいずれか1項記載のチオカルバミド。
- 水中に分散又は溶解されたポリマー用の架橋剤としての、請求項1から9までのいずれか1項記載のチオカルバミドの使用。
- ポリマー100質量部当たり請求項1から9までのいずれか1項記載のチオカルバミド0.1〜50質量部を含有している、水性ポリマー分散液又はポリマー水溶液。
- 分散又は溶解されたポリマーが、ポリウレタン又はエチレン系不飽和化合物(モノマー)のラジカル重合により得ることができるポリマー(重付加物と略す)である、請求項11記載の水性ポリマー分散液又はポリマー水溶液。
- 溶解又は分散されたポリマーが、カルボン酸基を有している、請求項11又は12記載の水性ポリマー分散液又はポリマー水溶液。
- 接着剤、含浸剤又はコーティング剤としての、請求項11から13までのいずれか1項記載のポリマー分散液又はポリマー溶液の使用。
- 熱活性化可能な接着剤として又は熱活性化可能な接着剤における、請求項11から13までのいずれか1項記載のポリマー分散液又はポリマー溶液の使用。
- 請求項11から13までのいずれか1項記載のポリマー分散液又はポリマー溶液を用いてコーティング、含浸又は接着された基体。
- エステル基又はアミド基含有のポリマー用の安定剤としての、請求項1から9までのいずれか1項記載のチオカルバミドの使用。
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DE200410011833 DE102004011833A1 (de) | 2004-03-09 | 2004-03-09 | Carbodiimide mit Thiocarbamidsäureestergruppen |
PCT/EP2005/002293 WO2005087718A2 (de) | 2004-03-09 | 2005-03-04 | Carbodiimide mit thiocarbamidsäureestergruppen |
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JP2007527942A true JP2007527942A (ja) | 2007-10-04 |
JP4521026B2 JP4521026B2 (ja) | 2010-08-11 |
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JP2007502246A Expired - Fee Related JP4521026B2 (ja) | 2004-03-09 | 2005-03-04 | チオカルバミド酸エステル基を有するカルボジイミド |
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US (1) | US7563837B2 (ja) |
EP (1) | EP1725609B1 (ja) |
JP (1) | JP4521026B2 (ja) |
AT (1) | ATE396227T1 (ja) |
DE (2) | DE102004011833A1 (ja) |
ES (1) | ES2306104T3 (ja) |
WO (1) | WO2005087718A2 (ja) |
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EP2361938A1 (de) * | 2010-02-18 | 2011-08-31 | Bayer MaterialScience AG | Lichtechte Beschichtungsmittel |
WO2011061206A1 (en) * | 2009-11-19 | 2011-05-26 | Bayer Materialscience Ag | Light-stable anionic polyurethane polyureas |
MX2012010068A (es) * | 2010-03-02 | 2012-12-17 | Ppg Ind Ohio Inc | Composiciones de revestimiento de un componente, curables al ambiente, que cotienen agua, metodos relacionados y sustratos revestidos. |
US11814558B2 (en) * | 2018-02-21 | 2023-11-14 | Basf Se | Method for producing articles coated with adhesive |
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JPH05117221A (ja) * | 1991-04-03 | 1993-05-14 | Stahl Holland Bv | 多官能基性水分散性交差結合剤 |
JP2003513952A (ja) * | 1999-11-11 | 2003-04-15 | ビーエーエスエフ アクチェンゲゼルシャフト | カルボキシル又はカルボキシレート基を含むカルボジイミド |
JP2003306476A (ja) * | 2002-04-16 | 2003-10-28 | Nippon Paint Co Ltd | 3鎖型親水性カルボジイミド化合物及び水性塗料組成物 |
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DE3720860A1 (de) | 1987-06-24 | 1989-01-05 | Basf Ag | Lagerstabile waessrige polymerdispersionen |
US5160507A (en) * | 1990-06-04 | 1992-11-03 | Mobil Oil Corp. | Multifunctional ester-type additives for liquid hydrocarbyl or hydrocarbyloxy fuel |
US5859166A (en) * | 1994-06-10 | 1999-01-12 | Nisshinbo Industries, Inc. | Hydrophilic resin composition |
DE19521500A1 (de) | 1995-06-13 | 1996-06-05 | Basf Ag | Wässerige Dispersion enthaltend ein Polyurethan und einen Fluoreszenzfarbstoff |
EP0937563A1 (de) | 1998-02-24 | 1999-08-25 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Häuten aus Polyurethandispersionen |
US6121406A (en) | 1998-04-20 | 2000-09-19 | Nisshinbo Industries, Inc. | Mixture of hydrophilic dicyclohexylmethanecarbodiimide |
DE10000656A1 (de) | 2000-01-11 | 2001-07-12 | Basf Ag | Carbodiimide mit Carboxyl- oder Carboxylatgruppen |
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2004
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- 2005-03-04 DE DE200550004188 patent/DE502005004188D1/de active Active
- 2005-03-04 WO PCT/EP2005/002293 patent/WO2005087718A2/de active IP Right Grant
- 2005-03-04 US US10/591,283 patent/US7563837B2/en not_active Expired - Fee Related
- 2005-03-04 JP JP2007502246A patent/JP4521026B2/ja not_active Expired - Fee Related
- 2005-03-04 EP EP05715729A patent/EP1725609B1/de not_active Not-in-force
- 2005-03-04 ES ES05715729T patent/ES2306104T3/es active Active
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05117221A (ja) * | 1991-04-03 | 1993-05-14 | Stahl Holland Bv | 多官能基性水分散性交差結合剤 |
JP2003513952A (ja) * | 1999-11-11 | 2003-04-15 | ビーエーエスエフ アクチェンゲゼルシャフト | カルボキシル又はカルボキシレート基を含むカルボジイミド |
JP2003306476A (ja) * | 2002-04-16 | 2003-10-28 | Nippon Paint Co Ltd | 3鎖型親水性カルボジイミド化合物及び水性塗料組成物 |
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WO2005087718A3 (de) | 2005-11-10 |
ES2306104T3 (es) | 2008-11-01 |
EP1725609A2 (de) | 2006-11-29 |
EP1725609B1 (de) | 2008-05-21 |
US7563837B2 (en) | 2009-07-21 |
JP4521026B2 (ja) | 2010-08-11 |
US20070179226A1 (en) | 2007-08-02 |
DE102004011833A1 (de) | 2005-09-29 |
DE502005004188D1 (en) | 2008-07-03 |
ATE396227T1 (de) | 2008-06-15 |
WO2005087718A2 (de) | 2005-09-22 |
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