JP2010504400A - ジアミン系鎖延長剤組成物 - Google Patents
ジアミン系鎖延長剤組成物 Download PDFInfo
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- JP2010504400A JP2010504400A JP2009529282A JP2009529282A JP2010504400A JP 2010504400 A JP2010504400 A JP 2010504400A JP 2009529282 A JP2009529282 A JP 2009529282A JP 2009529282 A JP2009529282 A JP 2009529282A JP 2010504400 A JP2010504400 A JP 2010504400A
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- JP
- Japan
- Prior art keywords
- diamine
- group
- aliphatic
- hydrocarbyl
- aliphatic secondary
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 239000004970 Chain extender Substances 0.000 title claims abstract description 37
- 125000004427 diamine group Chemical group 0.000 title abstract 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 133
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 99
- 125000003118 aryl group Chemical group 0.000 claims abstract description 88
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims abstract description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000004985 diamines Chemical group 0.000 claims description 119
- -1 3,3-dimethyl-2-butyl Chemical group 0.000 claims description 63
- 125000003277 amino group Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 36
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 229920005862 polyol Polymers 0.000 claims description 17
- 150000003077 polyols Chemical class 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 13
- 239000004615 ingredient Substances 0.000 claims description 11
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- MORNPDNVUROSRS-UHFFFAOYSA-N n,n'-bis(3,3-dimethylbutan-2-yl)hexane-1,6-diamine Chemical compound CC(C)(C)C(C)NCCCCCCNC(C)C(C)(C)C MORNPDNVUROSRS-UHFFFAOYSA-N 0.000 claims description 10
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920002396 Polyurea Polymers 0.000 abstract description 22
- 229920002635 polyurethane Polymers 0.000 abstract description 15
- 239000004814 polyurethane Substances 0.000 abstract description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 25
- 239000000306 component Substances 0.000 description 23
- 238000009472 formulation Methods 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 150000002513 isocyanates Chemical class 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000002312 hydrocarbylidene group Chemical group 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 150000004984 aromatic diamines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- KZTROCYBPMKGAW-UHFFFAOYSA-N 4-[[4-amino-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C(C)C)C=2)C(C)C)=C1 KZTROCYBPMKGAW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 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 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 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 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- RPXCKTUCFRWQEX-UHFFFAOYSA-N 1-cyclobutyl-n-[6-[[2-(1-cyclobutylethylideneamino)-3,4-dihexylphenyl]methyl]-2,3-dihexylphenyl]ethanimine Chemical compound C1CCC1C(C)=NC1=C(CCCCCC)C(CCCCCC)=CC=C1CC1=CC=C(CCCCCC)C(CCCCCC)=C1N=C(C)C1CCC1 RPXCKTUCFRWQEX-UHFFFAOYSA-N 0.000 description 1
- JPQWKGFRVOYHPG-UHFFFAOYSA-N 1-cyclopentyl-n-[4-[2-[4-(1-cyclopentylethylideneamino)-3,5-diethylphenyl]ethyl]-2,6-diethylphenyl]ethanimine Chemical compound C=1C(CC)=C(N=C(C)C2CCCC2)C(CC)=CC=1CCC(C=C1CC)=CC(CC)=C1N=C(C)C1CCCC1 JPQWKGFRVOYHPG-UHFFFAOYSA-N 0.000 description 1
- ZCZRMWDMWAVPSK-UHFFFAOYSA-N 1-cyclopentyl-n-[4-[2-[4-(1-cyclopentylethylideneamino)-3-methylphenyl]ethyl]-2-methylphenyl]ethanimine Chemical compound C1CCCC1C(C)=NC(C(=C1)C)=CC=C1CCC(C=C1C)=CC=C1N=C(C)C1CCCC1 ZCZRMWDMWAVPSK-UHFFFAOYSA-N 0.000 description 1
- PRJGEUSHXHRGKR-UHFFFAOYSA-N 1-cyclopropyl-N-[4-(1-cyclopropylethylideneamino)-3-pentylphenyl]ethanimine Chemical compound CCCCCC1=CC(N=C(C)C2CC2)=CC=C1N=C(C)C1CC1 PRJGEUSHXHRGKR-UHFFFAOYSA-N 0.000 description 1
- ZCCYZPVCYWWTTH-UHFFFAOYSA-N 1-cyclopropyl-n-[4,6-di(butan-2-yl)-3-(1-cyclopropylethylideneamino)-2-methylphenyl]ethanimine Chemical compound CC1=C(N=C(C)C2CC2)C(C(C)CC)=CC(C(C)CC)=C1N=C(C)C1CC1 ZCCYZPVCYWWTTH-UHFFFAOYSA-N 0.000 description 1
- QTZIZDZBCKDYLI-UHFFFAOYSA-N 1-cyclopropyl-n-[5-(1-cyclopropylethylideneamino)pentyl]ethanimine Chemical compound C1CC1C(C)=NCCCCCN=C(C)C1CC1 QTZIZDZBCKDYLI-UHFFFAOYSA-N 0.000 description 1
- MTPCYYDPKXMORZ-UHFFFAOYSA-N 1-n,2-n-bis(3-methylcyclohex-2-en-1-yl)propane-1,2-diamine Chemical compound C1CCC(C)=CC1NC(C)CNC1CCCC(C)=C1 MTPCYYDPKXMORZ-UHFFFAOYSA-N 0.000 description 1
- PZJXBTPESLUFLK-UHFFFAOYSA-N 1-n,2-n-di(butan-2-yl)propane-1,2-diamine Chemical compound CCC(C)NCC(C)NC(C)CC PZJXBTPESLUFLK-UHFFFAOYSA-N 0.000 description 1
- FRDZCJLKUYDJIY-UHFFFAOYSA-N 1-n,2-n-di(hexan-3-yl)cyclohexane-1,2-diamine Chemical compound CCCC(CC)NC1CCCCC1NC(CC)CCC FRDZCJLKUYDJIY-UHFFFAOYSA-N 0.000 description 1
- CKQQEEOHXRBWCG-UHFFFAOYSA-N 1-n,2-n-di(undecyl)cyclohexane-1,2-diamine Chemical compound CCCCCCCCCCCNC1CCCCC1NCCCCCCCCCCC CKQQEEOHXRBWCG-UHFFFAOYSA-N 0.000 description 1
- NDHGSGLGMQOHPA-UHFFFAOYSA-N 1-n,2-n-dihexylcyclohexane-1,2-diamine Chemical compound CCCCCCNC1CCCCC1NCCCCCC NDHGSGLGMQOHPA-UHFFFAOYSA-N 0.000 description 1
- GJJBLVIGIOFBDJ-UHFFFAOYSA-N 1-n,3-n-dicyclohexylcyclohexane-1,3-diamine Chemical compound C1CCCCC1NC1CC(NC2CCCCC2)CCC1 GJJBLVIGIOFBDJ-UHFFFAOYSA-N 0.000 description 1
- GAARTPZCZSZNTM-UHFFFAOYSA-N 1-n,3-n-didecylcyclohexane-1,3-diamine Chemical compound CCCCCCCCCCNC1CCCC(NCCCCCCCCCC)C1 GAARTPZCZSZNTM-UHFFFAOYSA-N 0.000 description 1
- PAVHOAHCTHEZIQ-UHFFFAOYSA-N 1-n,4-n-bis(1-cyclobutylethyl)cyclohexane-1,4-diamine Chemical compound C1CCC1C(C)NC(CC1)CCC1NC(C)C1CCC1 PAVHOAHCTHEZIQ-UHFFFAOYSA-N 0.000 description 1
- VCDVGFPZVKFESM-UHFFFAOYSA-N 1-n,4-n-dibutylcyclohexane-1,4-diamine Chemical compound CCCCNC1CCC(NCCCC)CC1 VCDVGFPZVKFESM-UHFFFAOYSA-N 0.000 description 1
- KOINUAKALTWYOS-UHFFFAOYSA-N 1-phenyl-n-[4-[2-[4-(1-phenylbutan-2-ylideneamino)-3,5-di(propan-2-yl)phenyl]ethyl]-2,6-di(propan-2-yl)phenyl]butan-2-imine Chemical compound CC(C)C=1C=C(CCC=2C=C(C(N=C(CC)CC=3C=CC=CC=3)=C(C(C)C)C=2)C(C)C)C=C(C(C)C)C=1N=C(CC)CC1=CC=CC=C1 KOINUAKALTWYOS-UHFFFAOYSA-N 0.000 description 1
- BQJNDFXBOSXMLM-UHFFFAOYSA-N 2,3,5,6-tetraethylbenzene-1,4-diamine Chemical compound CCC1=C(N)C(CC)=C(CC)C(N)=C1CC BQJNDFXBOSXMLM-UHFFFAOYSA-N 0.000 description 1
- HNEIEUKJFTUIBM-UHFFFAOYSA-N 2,3,5-tripropylbenzene-1,4-diamine Chemical compound CCCC1=CC(N)=C(CCC)C(CCC)=C1N HNEIEUKJFTUIBM-UHFFFAOYSA-N 0.000 description 1
- ABQQPHFTJYCSIA-UHFFFAOYSA-N 2,3-diethylbenzene-1,4-diamine Chemical compound CCC1=C(N)C=CC(N)=C1CC ABQQPHFTJYCSIA-UHFFFAOYSA-N 0.000 description 1
- JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 description 1
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- NRUAHCQFVDVWJK-UHFFFAOYSA-N 2,5-dimethyl-2-n,5-n-bis(5-methyl-2-propan-2-ylcyclohexyl)hexane-2,5-diamine Chemical compound CC(C)C1CCC(C)CC1NC(C)(C)CCC(C)(C)NC1C(C(C)C)CCC(C)C1 NRUAHCQFVDVWJK-UHFFFAOYSA-N 0.000 description 1
- BDBODCFNUORELH-UHFFFAOYSA-N 2,5-dimethyl-2-n,5-n-di(pentan-3-yl)hexane-2,5-diamine Chemical compound CCC(CC)NC(C)(C)CCC(C)(C)NC(CC)CC BDBODCFNUORELH-UHFFFAOYSA-N 0.000 description 1
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- OBEARTBLLJIVLW-UHFFFAOYSA-N 2,5-dioctylbenzene-1,4-diamine Chemical compound CCCCCCCCC1=CC(N)=C(CCCCCCCC)C=C1N OBEARTBLLJIVLW-UHFFFAOYSA-N 0.000 description 1
- FFRIGRDLHKLAQD-UHFFFAOYSA-N 2-[(2-amino-3-propylphenyl)methyl]-6-propylaniline Chemical compound CCCC1=CC=CC(CC=2C(=C(CCC)C=CC=2)N)=C1N FFRIGRDLHKLAQD-UHFFFAOYSA-N 0.000 description 1
- KXKMZNOTGIBFNP-UHFFFAOYSA-N 2-[(2-amino-4-tert-butylphenyl)methyl]-5-tert-butylaniline Chemical compound NC1=CC(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C=C1N KXKMZNOTGIBFNP-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- HDVUPIFFKAHPJY-UHFFFAOYSA-N 2-butylaniline Chemical compound CCCCC1=CC=CC=C1N HDVUPIFFKAHPJY-UHFFFAOYSA-N 0.000 description 1
- TZFFGICBCZBYDO-UHFFFAOYSA-N 2-ethyl-4-methyl-6-propan-2-ylbenzene-1,3-diamine Chemical compound CCC1=C(N)C(C)=CC(C(C)C)=C1N TZFFGICBCZBYDO-UHFFFAOYSA-N 0.000 description 1
- SDSPYJRNPBYBHY-UHFFFAOYSA-N 2-phenyl-n-[2,3,5,6-tetraethyl-4-(2-phenylethylideneamino)phenyl]ethanimine Chemical compound CCC=1C(CC)=C(N=CCC=2C=CC=CC=2)C(CC)=C(CC)C=1N=CCC1=CC=CC=C1 SDSPYJRNPBYBHY-UHFFFAOYSA-N 0.000 description 1
- MIFBCZGDOOSVDT-UHFFFAOYSA-N 2-phenyl-n-[3,4,6-tripentyl-2-[[2,3,5-tripentyl-6-(2-phenylethylideneamino)phenyl]methyl]phenyl]ethanimine Chemical compound CCCCCC=1C(CCCCC)=CC(CCCCC)=C(N=CCC=2C=CC=CC=2)C=1CC1=C(CCCCC)C(CCCCC)=CC(CCCCC)=C1N=CCC1=CC=CC=C1 MIFBCZGDOOSVDT-UHFFFAOYSA-N 0.000 description 1
- HLOXRRSFYXEJMC-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=C(N)C=CC=C1N HLOXRRSFYXEJMC-UHFFFAOYSA-N 0.000 description 1
- GWIUAENVORNODL-UHFFFAOYSA-N 2-tert-butyl-6-methylaniline Chemical compound CC1=CC=CC(C(C)(C)C)=C1N GWIUAENVORNODL-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- POZCGQKROVHZNL-UHFFFAOYSA-N 3,4-diheptyl-5,6-dimethylbenzene-1,2-diamine Chemical compound CCCCCCCC1=C(C)C(C)=C(N)C(N)=C1CCCCCCC POZCGQKROVHZNL-UHFFFAOYSA-N 0.000 description 1
- GBFXOJRWKYQINU-UHFFFAOYSA-N 3,6-dibutylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(CCCC)C(N)=C1N GBFXOJRWKYQINU-UHFFFAOYSA-N 0.000 description 1
- QEFONSYHZREXGC-UHFFFAOYSA-N 3-[(3-amino-2,4-dibutylphenyl)methyl]-2,6-dibutylaniline Chemical compound CCCCC1=C(N)C(CCCC)=CC=C1CC1=CC=C(CCCC)C(N)=C1CCCC QEFONSYHZREXGC-UHFFFAOYSA-N 0.000 description 1
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- MZSSACKNPQFLOH-UHFFFAOYSA-N n-[4-[[4-(cyclohexylideneamino)-2,3,5-trimethylphenyl]methyl]-2,3,6-trimethylphenyl]cyclohexanimine Chemical compound CC=1C(C)=C(N=C2CCCCC2)C(C)=CC=1CC(C(=C1C)C)=CC(C)=C1N=C1CCCCC1 MZSSACKNPQFLOH-UHFFFAOYSA-N 0.000 description 1
- HRVICIFYGIAVSX-UHFFFAOYSA-N n-[4-[[4-(heptan-2-ylideneamino)-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)phenyl]heptan-2-imine Chemical compound C1=C(C(C)C)C(N=C(C)CCCCC)=C(C(C)C)C=C1CC1=CC(C(C)C)=C(N=C(C)CCCCC)C(C(C)C)=C1 HRVICIFYGIAVSX-UHFFFAOYSA-N 0.000 description 1
- IQOHSDPXJDONOD-UHFFFAOYSA-N n-[5-(but-2-enylideneamino)-2,3,4-trihexylphenyl]but-2-en-1-imine Chemical compound CCCCCCC1=C(CCCCCC)C(N=CC=CC)=CC(N=CC=CC)=C1CCCCCC IQOHSDPXJDONOD-UHFFFAOYSA-N 0.000 description 1
- UGDZNNPZKYTCMQ-UHFFFAOYSA-N n-[5-(cyclopent-2-en-1-ylideneamino)-2,4-dipropylphenyl]cyclopent-2-en-1-imine Chemical compound CCCC1=CC(CCC)=C(N=C2C=CCC2)C=C1N=C1CCC=C1 UGDZNNPZKYTCMQ-UHFFFAOYSA-N 0.000 description 1
- HTVMKYLVVQABPJ-UHFFFAOYSA-N n-[5-tert-butyl-2-[[4-tert-butyl-2-(2,4-dimethylpentan-3-ylideneamino)phenyl]methyl]phenyl]-2,4-dimethylpentan-3-imine Chemical compound CC(C)C(C(C)C)=NC1=CC(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C=C1N=C(C(C)C)C(C)C HTVMKYLVVQABPJ-UHFFFAOYSA-N 0.000 description 1
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- OZZQFRVQKUXZOH-UHFFFAOYSA-N n-[7-(propan-2-ylideneamino)heptyl]propan-2-imine Chemical compound CC(C)=NCCCCCCCN=C(C)C OZZQFRVQKUXZOH-UHFFFAOYSA-N 0.000 description 1
- KRIUVVHXHMZGOU-UHFFFAOYSA-N n-[8-(butan-2-ylideneamino)octyl]butan-2-imine Chemical compound CCC(C)=NCCCCCCCCN=C(C)CC KRIUVVHXHMZGOU-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
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- C07C211/12—1,6-Diaminohexanes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/51—Phenylenediamines
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
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- 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
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/50—Polyethers having heteroatoms other than oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/534,968 US7964695B2 (en) | 2005-03-28 | 2006-09-25 | Chain extenders |
| PCT/US2007/068384 WO2008039571A1 (en) | 2006-09-25 | 2007-05-07 | Diamine chain extender compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010504400A true JP2010504400A (ja) | 2010-02-12 |
| JP2010504400A5 JP2010504400A5 (enExample) | 2010-05-06 |
Family
ID=38567027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009529282A Pending JP2010504400A (ja) | 2006-09-25 | 2007-05-07 | ジアミン系鎖延長剤組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7964695B2 (enExample) |
| EP (1) | EP2078048A1 (enExample) |
| JP (1) | JP2010504400A (enExample) |
| KR (1) | KR20090074159A (enExample) |
| CN (1) | CN101516948B (enExample) |
| AU (1) | AU2007300409B2 (enExample) |
| BR (1) | BRPI0716043A2 (enExample) |
| CA (1) | CA2661513A1 (enExample) |
| EA (1) | EA017131B1 (enExample) |
| WO (1) | WO2008039571A1 (enExample) |
Cited By (1)
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| JP7171956B1 (ja) | 2022-03-29 | 2022-11-15 | アイカ工業株式会社 | コンクリート床用目地材組成物及びその施工方法及びコンクリート床 |
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| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| US8212078B2 (en) * | 2005-03-28 | 2012-07-03 | Albemarle Corporation | Diimines and secondary diamines |
| US8076518B2 (en) * | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| JP2010515811A (ja) * | 2007-01-10 | 2010-05-13 | アルベマール・コーポレーシヨン | 反応射出成形および噴霧システムのための組成物 |
| US20090035350A1 (en) * | 2007-08-03 | 2009-02-05 | John Stankus | Polymers for implantable devices exhibiting shape-memory effects |
| US9259515B2 (en) | 2008-04-10 | 2016-02-16 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from polyurethanes with grafted radiopaque groups |
| US10000608B2 (en) * | 2013-03-15 | 2018-06-19 | The Board Of Trustees Of The University Of Illinois | Dynamic urea bonds for reversible and self-healing polymers |
| US10507621B2 (en) * | 2014-06-11 | 2019-12-17 | Basf Se | Polyurethane compound for producing an integrated insulation component |
| CN107663671B (zh) * | 2017-08-16 | 2020-07-28 | 东华大学 | 一种耐热聚氨酯弹性纤维及其制备方法 |
| CN107686548B (zh) * | 2017-08-22 | 2021-12-10 | 山西省建筑科学研究院 | 水性纯聚脲的制备方法 |
| WO2025224005A1 (en) * | 2024-04-25 | 2025-10-30 | Huntsman International Llc | Slow cure hybrid polyurea |
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- 2007-05-07 EA EA200970324A patent/EA017131B1/ru not_active IP Right Cessation
- 2007-05-07 CN CN2007800354095A patent/CN101516948B/zh not_active Expired - Fee Related
- 2007-05-07 WO PCT/US2007/068384 patent/WO2008039571A1/en not_active Ceased
- 2007-05-07 EP EP07783397A patent/EP2078048A1/en not_active Withdrawn
- 2007-05-07 AU AU2007300409A patent/AU2007300409B2/en not_active Ceased
- 2007-05-07 KR KR1020097005110A patent/KR20090074159A/ko not_active Withdrawn
- 2007-05-07 BR BRPI0716043-7A patent/BRPI0716043A2/pt not_active IP Right Cessation
- 2007-05-07 JP JP2009529282A patent/JP2010504400A/ja active Pending
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| JPH04132722A (ja) * | 1990-01-02 | 1992-05-07 | Basf Ag | N−置換された尿素基およびアミド基を結合して有するエラストマーをベースとする弾性成形体を製造する方法 |
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|---|---|---|---|---|
| JP7171956B1 (ja) | 2022-03-29 | 2022-11-15 | アイカ工業株式会社 | コンクリート床用目地材組成物及びその施工方法及びコンクリート床 |
| JP2023146075A (ja) * | 2022-03-29 | 2023-10-12 | アイカ工業株式会社 | コンクリート床用目地材組成物及びその施工方法及びコンクリート床 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007300409A1 (en) | 2008-04-03 |
| US8080626B2 (en) | 2011-12-20 |
| CA2661513A1 (en) | 2008-04-03 |
| WO2008039571A1 (en) | 2008-04-03 |
| KR20090074159A (ko) | 2009-07-06 |
| BRPI0716043A2 (pt) | 2013-01-08 |
| EA017131B1 (ru) | 2012-10-30 |
| US20070270566A1 (en) | 2007-11-22 |
| CN101516948B (zh) | 2012-08-15 |
| EP2078048A1 (en) | 2009-07-15 |
| US20110137005A1 (en) | 2011-06-09 |
| EA200970324A1 (ru) | 2009-08-28 |
| AU2007300409B2 (en) | 2010-10-14 |
| US7964695B2 (en) | 2011-06-21 |
| CN101516948A (zh) | 2009-08-26 |
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