AU2007300409B2 - Diamine chain extender compositions - Google Patents
Diamine chain extender compositions Download PDFInfo
- Publication number
- AU2007300409B2 AU2007300409B2 AU2007300409A AU2007300409A AU2007300409B2 AU 2007300409 B2 AU2007300409 B2 AU 2007300409B2 AU 2007300409 A AU2007300409 A AU 2007300409A AU 2007300409 A AU2007300409 A AU 2007300409A AU 2007300409 B2 AU2007300409 B2 AU 2007300409B2
- Authority
- AU
- Australia
- Prior art keywords
- diamine
- aliphatic
- aromatic
- group
- butyl
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 79
- 239000004970 Chain extender Substances 0.000 title claims description 38
- 125000004427 diamine group Chemical group 0.000 title 1
- 125000001931 aliphatic group Chemical group 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 150000004985 diamines Chemical group 0.000 claims description 73
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 71
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 31
- 229910000071 diazene Inorganic materials 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 24
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000002312 hydrocarbylidene group Chemical group 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 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 10
- 239000004615 ingredient Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 6
- MORNPDNVUROSRS-UHFFFAOYSA-N n,n'-bis(3,3-dimethylbutan-2-yl)hexane-1,6-diamine Chemical group CC(C)(C)C(C)NCCCCCCNC(C)C(C)(C)C MORNPDNVUROSRS-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 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 claims description 3
- GMTFURRRXIRGLH-UHFFFAOYSA-N C12CCCC2C2(CN)CC1CC2 Chemical compound C12CCCC2C2(CN)CC1CC2 GMTFURRRXIRGLH-UHFFFAOYSA-N 0.000 claims description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- -1 aliphatic diamines Chemical group 0.000 description 45
- 239000000306 component Substances 0.000 description 34
- 125000003277 amino group Chemical group 0.000 description 29
- 238000009472 formulation Methods 0.000 description 20
- 229920002396 Polyurea Polymers 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 12
- 239000004814 polyurethane Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 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 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 2
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 101100065878 Caenorhabditis elegans sec-10 gene Proteins 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 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
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 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
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- VWTSFKBXVRJWRK-UHFFFAOYSA-N 1-cyclobutyl-n-[4-[[4-(1-cyclobutylethylideneamino)-1,3,5,6-tetramethylcyclohexa-2,4-dien-1-yl]methyl]-2,3,4,6-tetramethylcyclohexa-1,5-dien-1-yl]ethanimine Chemical compound CC1=CC(CC2(C)C(C(C)=C(N=C(C)C3CCC3)C(C)=C2)C)(C)C(C)C(C)=C1N=C(C)C1CCC1 VWTSFKBXVRJWRK-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
- 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
- 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
- GAARTPZCZSZNTM-UHFFFAOYSA-N 1-n,3-n-didecylcyclohexane-1,3-diamine Chemical compound CCCCCCCCCCNC1CCCC(NCCCCCCCCCC)C1 GAARTPZCZSZNTM-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
- 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
- USRBRYHXYFBBHZ-UHFFFAOYSA-N 2,3-dihexylaniline Chemical compound CCCCCCC1=CC=CC(N)=C1CCCCCC USRBRYHXYFBBHZ-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
- PXPRVOINQSYRMT-UHFFFAOYSA-N 2,4-diethyl-6-methylcyclohexane-1,3-diamine Chemical compound CCC1CC(C)C(N)C(CC)C1N PXPRVOINQSYRMT-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
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- LULKKMCLPODSOJ-UHFFFAOYSA-N 2-[(2-amino-3,5,6-tripentylphenyl)methyl]-3,4,6-tripentylaniline Chemical compound CCCCCC1=CC(CCCCC)=C(CCCCC)C(CC=2C(=C(CCCCC)C=C(CCCCC)C=2N)CCCCC)=C1N LULKKMCLPODSOJ-UHFFFAOYSA-N 0.000 description 1
- DHCADOBAAZQBTI-UHFFFAOYSA-N 2-[(2-amino-3,6-dipropylphenyl)methyl]-3,6-dipropylaniline Chemical compound CCCC1=CC=C(CCC)C(CC=2C(=C(CCC)C=CC=2CCC)N)=C1N DHCADOBAAZQBTI-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
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-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
- QNDKVZNTVPQFRH-UHFFFAOYSA-N 2-heptylbenzene-1,3-diamine Chemical compound C(CCCCCC)C1=C(C=CC=C1N)N QNDKVZNTVPQFRH-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-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
- 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
- SKJBZOVACDONGZ-UHFFFAOYSA-N 3-[(3-amino-2,4,5-trihexylphenyl)methyl]-2,5,6-trihexylaniline Chemical compound NC1=C(CCCCCC)C(CCCCCC)=CC(CC=2C(=C(N)C(CCCCCC)=C(CCCCCC)C=2)CCCCCC)=C1CCCCCC SKJBZOVACDONGZ-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
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- XQROPVBSRZPIEX-UHFFFAOYSA-N 3-[[3-amino-2,4-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=C1CC1=CC=C(C(C)C)C(N)=C1C(C)C XQROPVBSRZPIEX-UHFFFAOYSA-N 0.000 description 1
- PWBIXBPEKXAHGI-UHFFFAOYSA-N 3-methyl-n-[4-[[3-[(3-methylcyclohex-2-en-1-ylidene)amino]phenyl]methyl]phenyl]cyclohex-2-en-1-imine Chemical compound C1CCC(C)=CC1=NC(C=C1)=CC=C1CC1=CC=CC(N=C2C=C(C)CCC2)=C1 PWBIXBPEKXAHGI-UHFFFAOYSA-N 0.000 description 1
- DPKTVUKEPNBABS-UHFFFAOYSA-N 3-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC(N)=C1 DPKTVUKEPNBABS-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- NGRMNIHDBVGDOO-UHFFFAOYSA-N 4,6-di(butan-2-yl)-2-methylbenzene-1,3-diamine Chemical compound CCC(C)C1=CC(C(C)CC)=C(N)C(C)=C1N NGRMNIHDBVGDOO-UHFFFAOYSA-N 0.000 description 1
- XMUFMUCUOXTGQX-UHFFFAOYSA-N 4,6-dipropylbenzene-1,3-diamine Chemical compound CCCC1=CC(CCC)=C(N)C=C1N XMUFMUCUOXTGQX-UHFFFAOYSA-N 0.000 description 1
- CNJLMVZFWLNOEP-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]heptan-5-one Chemical group O=C1C(C)CCC2C(C)(C)C12 CNJLMVZFWLNOEP-UHFFFAOYSA-N 0.000 description 1
- KTCJNULAKCARHF-UHFFFAOYSA-N 4-[(4-amino-1,3,5,6-tetramethylcyclohexa-2,4-dien-1-yl)methyl]-2,3,4,6-tetramethylcyclohexa-1,5-dien-1-amine Chemical compound CC1C(C)=C(N)C(C)=CC1(C)CC1(C)C(C)C(C)=C(N)C(C)=C1 KTCJNULAKCARHF-UHFFFAOYSA-N 0.000 description 1
- SYCGFGRXCVNIPF-UHFFFAOYSA-N 4-[(4-amino-2,3,5-trimethylphenyl)methyl]-2,3,6-trimethylaniline Chemical compound CC1=C(N)C(C)=CC(CC=2C(=C(C)C(N)=C(C)C=2)C)=C1C SYCGFGRXCVNIPF-UHFFFAOYSA-N 0.000 description 1
- OSRXTGYUAJPODP-UHFFFAOYSA-N 4-[(4-amino-2,6-ditert-butylphenyl)methyl]-3,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC(N)=CC(C(C)(C)C)=C1CC1=C(C(C)(C)C)C=C(N)C=C1C(C)(C)C OSRXTGYUAJPODP-UHFFFAOYSA-N 0.000 description 1
- NRXZKUIQDDRUMV-UHFFFAOYSA-N 4-[(4-amino-2-butan-2-ylphenyl)methyl]-3-butan-2-ylaniline Chemical compound CCC(C)C1=CC(N)=CC=C1CC1=CC=C(N)C=C1C(C)CC NRXZKUIQDDRUMV-UHFFFAOYSA-N 0.000 description 1
- FLNVGZMDLLIECD-UHFFFAOYSA-N 4-[(4-amino-3-methyl-5-propan-2-ylphenyl)methyl]-2-methyl-6-propan-2-ylaniline Chemical compound CC1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C)C=2)C(C)C)=C1 FLNVGZMDLLIECD-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- ZDJPRKOFFQXIAI-UHFFFAOYSA-N 4-[2-(4-amino-3,5-diethylphenyl)ethyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CCC=2C=C(CC)C(N)=C(CC)C=2)=C1 ZDJPRKOFFQXIAI-UHFFFAOYSA-N 0.000 description 1
- ROJMDQBRKBPHIU-UHFFFAOYSA-N 4-ethylbenzene-1,2-diamine Chemical compound CCC1=CC=C(N)C(N)=C1 ROJMDQBRKBPHIU-UHFFFAOYSA-N 0.000 description 1
- AKZOLEPNYXGNEH-UHFFFAOYSA-N 4-methyl-2,6-di(propan-2-yl)benzene-1,3-diamine Chemical compound CC(C)C1=CC(C)=C(N)C(C(C)C)=C1N AKZOLEPNYXGNEH-UHFFFAOYSA-N 0.000 description 1
- ZQNCDDVHPDSDKC-UHFFFAOYSA-N 5-butan-2-yl-2,3-diethylbenzene-1,4-diamine Chemical compound CCC(C)C1=CC(N)=C(CC)C(CC)=C1N ZQNCDDVHPDSDKC-UHFFFAOYSA-N 0.000 description 1
- FAFLSDGRQSUCAW-UHFFFAOYSA-N 5-methyl-n-[3-[[2-[(5-methyl-2-propan-2-ylcyclohexylidene)amino]phenyl]methyl]phenyl]-2-propan-2-ylcyclohexan-1-imine Chemical compound CC(C)C1CCC(C)CC1=NC1=CC=CC(CC=2C(=CC=CC=2)N=C2C(CCC(C)C2)C(C)C)=C1 FAFLSDGRQSUCAW-UHFFFAOYSA-N 0.000 description 1
- 101100148780 Caenorhabditis elegans sec-16A.1 gene Proteins 0.000 description 1
- 101100172886 Caenorhabditis elegans sec-6 gene Proteins 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- DNNXXFFLRWCPBC-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC=C1 Chemical class N=C=O.N=C=O.C1=CC=CC=C1 DNNXXFFLRWCPBC-UHFFFAOYSA-N 0.000 description 1
- 241001061036 Otho Species 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CSFZOENQUCDFFR-UHFFFAOYSA-N bis(aminomethyl)tricyclo[5,2,1,02,6]decane Chemical compound C12CCCC2(CN)C2(CN)CC1CC2 CSFZOENQUCDFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LUNQZVCDZKODKF-PFVVTREHSA-L copper acetic acid (2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoate (2S)-6-amino-2-[[(2S)-2-[(2-amino-1-oxidoethylidene)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoate hydron Chemical compound [Cu+2].CC(O)=O.CC(O)=O.NCCCC[C@@H](C([O-])=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1.NCCCC[C@@H](C([O-])=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 LUNQZVCDZKODKF-PFVVTREHSA-L 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- VZRUGPJUVWRHKM-UHFFFAOYSA-N dibutylhexamethylenediamine Chemical compound CCCCNCCCCCCNCCCC VZRUGPJUVWRHKM-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 108010038983 glycyl-histidyl-lysine Proteins 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- BBPXVYVXKAYBSS-UHFFFAOYSA-N hexane-2,5-diamine Chemical compound CC(N)CCC(C)N BBPXVYVXKAYBSS-UHFFFAOYSA-N 0.000 description 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 239000000463 material Substances 0.000 description 1
- YSWNJGZWTUUJNK-UHFFFAOYSA-N n,n'-di(nonyl)pentane-1,5-diamine Chemical compound CCCCCCCCCNCCCCCNCCCCCCCCC YSWNJGZWTUUJNK-UHFFFAOYSA-N 0.000 description 1
- MFIGJRRHGZYPDD-UHFFFAOYSA-N n,n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)NCCNC(C)C MFIGJRRHGZYPDD-UHFFFAOYSA-N 0.000 description 1
- WZJHIUUUFOXJHV-UHFFFAOYSA-N n,n'-dibutyloctane-1,8-diamine Chemical compound CCCCNCCCCCCCCNCCCC WZJHIUUUFOXJHV-UHFFFAOYSA-N 0.000 description 1
- AIGSVGROQWQSJH-UHFFFAOYSA-N n,n'-didecylpropane-1,3-diamine Chemical compound CCCCCCCCCCNCCCNCCCCCCCCCC AIGSVGROQWQSJH-UHFFFAOYSA-N 0.000 description 1
- ALZARSJEJMWPOM-UHFFFAOYSA-N n,n'-didodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCCCCCCCCCCC ALZARSJEJMWPOM-UHFFFAOYSA-N 0.000 description 1
- YNMUHYFHRWKFOF-UHFFFAOYSA-N n,n'-diheptyl-2-methylpentane-1,5-diamine Chemical compound CCCCCCCNCCCC(C)CNCCCCCCC YNMUHYFHRWKFOF-UHFFFAOYSA-N 0.000 description 1
- QFWFCEYVPYDGIL-UHFFFAOYSA-N n,n'-dihexyldodecane-1,12-diamine Chemical compound CCCCCCNCCCCCCCCCCCCNCCCCCC QFWFCEYVPYDGIL-UHFFFAOYSA-N 0.000 description 1
- LRJJEDYDYUMYAA-UHFFFAOYSA-N n,n'-dipropylheptane-1,7-diamine Chemical compound CCCNCCCCCCCNCCC LRJJEDYDYUMYAA-UHFFFAOYSA-N 0.000 description 1
- SOIVBKVKRNRGDW-UHFFFAOYSA-N n-[2,6-dibutyl-3-[[2,4-dibutyl-3-(2,4-dimethylpentan-3-ylideneamino)phenyl]methyl]phenyl]-2,4-dimethylpentan-3-imine Chemical compound CCCCC1=C(N=C(C(C)C)C(C)C)C(CCCC)=CC=C1CC1=CC=C(CCCC)C(N=C(C(C)C)C(C)C)=C1CCCC SOIVBKVKRNRGDW-UHFFFAOYSA-N 0.000 description 1
- LAKDHZNIRXILFM-UHFFFAOYSA-N n-[2,6-dibutyl-3-[[2,4-dibutyl-3-(propan-2-ylideneamino)phenyl]methyl]phenyl]propan-2-imine Chemical compound CCCCC1=C(N=C(C)C)C(CCCC)=CC=C1CC1=CC=C(CCCC)C(N=C(C)C)=C1CCCC LAKDHZNIRXILFM-UHFFFAOYSA-N 0.000 description 1
- OQRFABWPUTXSQV-UHFFFAOYSA-N n-[2-(cyclopentylideneamino)-4-ethylphenyl]cyclopentanimine Chemical compound C1CCCC1=NC1=CC(CC)=CC=C1N=C1CCCC1 OQRFABWPUTXSQV-UHFFFAOYSA-N 0.000 description 1
- ZNGHEIZDAPHIAV-UHFFFAOYSA-N n-[2-(propan-2-ylideneamino)phenyl]propan-2-imine Chemical compound CC(C)=NC1=CC=CC=C1N=C(C)C ZNGHEIZDAPHIAV-UHFFFAOYSA-N 0.000 description 1
- LKUHJJLFBLRERG-UHFFFAOYSA-N n-[2-[[2-(butan-2-ylideneamino)-3,6-dipropylphenyl]methyl]-3,6-dipropylphenyl]butan-2-imine Chemical compound CCCC1=CC=C(CCC)C(N=C(C)CC)=C1CC1=C(CCC)C=CC(CCC)=C1N=C(C)CC LKUHJJLFBLRERG-UHFFFAOYSA-N 0.000 description 1
- JZLKLTORQUKJCX-UHFFFAOYSA-N n-[2-[[2-(butan-2-ylideneamino)-3-propylphenyl]methyl]-6-propylphenyl]butan-2-imine Chemical compound CCCC1=CC=CC(CC=2C(=C(CCC)C=CC=2)N=C(C)CC)=C1N=C(C)CC JZLKLTORQUKJCX-UHFFFAOYSA-N 0.000 description 1
- TYNNTOKMDJAYLB-UHFFFAOYSA-N n-[2-[[2-[(2,5-dimethylcyclopentylidene)amino]phenyl]methyl]phenyl]-2,5-dimethylcyclopentan-1-imine Chemical compound CC1CCC(C)C1=NC1=CC=CC=C1CC1=CC=CC=C1N=C1C(C)CCC1C TYNNTOKMDJAYLB-UHFFFAOYSA-N 0.000 description 1
- YRSKAXXJFYWWOG-UHFFFAOYSA-N n-[2-tert-butyl-4-[[3-tert-butyl-5-methyl-4-[(3-methylcyclohex-2-en-1-ylidene)amino]phenyl]methyl]-6-methylphenyl]-3-methylcyclohex-2-en-1-imine Chemical compound C1CCC(C)=CC1=NC(C(=C1)C(C)(C)C)=C(C)C=C1CC(C=C1C(C)(C)C)=CC(C)=C1N=C1C=C(C)CCC1 YRSKAXXJFYWWOG-UHFFFAOYSA-N 0.000 description 1
- JTXZVRLBPPTGAB-UHFFFAOYSA-N n-[3-(3,3-dimethylbutan-2-ylideneamino)-2-ethyl-6-methyl-4-propan-2-ylphenyl]-3,3-dimethylbutan-2-imine Chemical compound CCC1=C(N=C(C)C(C)(C)C)C(C)=CC(C(C)C)=C1N=C(C)C(C)(C)C JTXZVRLBPPTGAB-UHFFFAOYSA-N 0.000 description 1
- ZMXWEFOIUNXAMB-UHFFFAOYSA-N n-[3-(but-2-enylideneamino)-2,4,5,6-tetrapropylphenyl]but-2-en-1-imine Chemical compound CCCC1=C(CCC)C(N=CC=CC)=C(CCC)C(N=CC=CC)=C1CCC ZMXWEFOIUNXAMB-UHFFFAOYSA-N 0.000 description 1
- JZLHKESNLNZTTM-UHFFFAOYSA-N n-[3-(butan-2-ylideneamino)-4-tert-butylphenyl]butan-2-imine Chemical compound CCC(C)=NC1=CC=C(C(C)(C)C)C(N=C(C)CC)=C1 JZLHKESNLNZTTM-UHFFFAOYSA-N 0.000 description 1
- XGJWMPBYMBTXGV-UHFFFAOYSA-N n-[3-(butan-2-ylideneamino)phenyl]butan-2-imine Chemical compound CCC(C)=NC1=CC=CC(N=C(C)CC)=C1 XGJWMPBYMBTXGV-UHFFFAOYSA-N 0.000 description 1
- ANLCHNSDNZEGNE-UHFFFAOYSA-N n-[3-[[3-(heptan-4-ylideneamino)-2,4,5-trihexylphenyl]methyl]-2,5,6-trihexylphenyl]heptan-4-imine Chemical compound CCCC(CCC)=NC1=C(CCCCCC)C(CCCCCC)=CC(CC=2C(=C(N=C(CCC)CCC)C(CCCCCC)=C(CCCCCC)C=2)CCCCCC)=C1CCCCCC ANLCHNSDNZEGNE-UHFFFAOYSA-N 0.000 description 1
- UQJQKAQAKLWDRN-UHFFFAOYSA-N n-[4-(butan-2-ylideneamino)-2,3,5,6-tetraethylphenyl]butan-2-imine Chemical compound CCC(C)=NC1=C(CC)C(CC)=C(N=C(C)CC)C(CC)=C1CC UQJQKAQAKLWDRN-UHFFFAOYSA-N 0.000 description 1
- KKVACVKMWOICGX-UHFFFAOYSA-N n-[4-(butan-2-ylideneamino)-2,3-diethylphenyl]butan-2-imine Chemical compound CCC(C)=NC1=CC=C(N=C(C)CC)C(CC)=C1CC KKVACVKMWOICGX-UHFFFAOYSA-N 0.000 description 1
- DGBBRLXMRHTXFG-UHFFFAOYSA-N n-[4-(hexan-3-ylideneamino)phenyl]hexan-3-imine Chemical compound CCCC(CC)=NC1=CC=C(N=C(CC)CCC)C=C1 DGBBRLXMRHTXFG-UHFFFAOYSA-N 0.000 description 1
- ATFXTKFYOJUPJB-UHFFFAOYSA-N n-[4-[2-[4-(butan-2-ylideneamino)-3,5-diethylphenyl]ethyl]-2,6-diethylphenyl]butan-2-imine Chemical compound C1=C(CC)C(N=C(C)CC)=C(CC)C=C1CCC1=CC(CC)=C(N=C(C)CC)C(CC)=C1 ATFXTKFYOJUPJB-UHFFFAOYSA-N 0.000 description 1
- UBCLZIZRLSSLFS-UHFFFAOYSA-N n-[4-[2-[4-(pentan-3-ylideneamino)phenyl]ethyl]phenyl]pentan-3-imine Chemical compound C1=CC(N=C(CC)CC)=CC=C1CCC1=CC=C(N=C(CC)CC)C=C1 UBCLZIZRLSSLFS-UHFFFAOYSA-N 0.000 description 1
- AMCDYMZKVGATAN-UHFFFAOYSA-N n-[4-[[2-(propan-2-ylideneamino)phenyl]methyl]phenyl]propan-2-imine Chemical compound C1=CC(N=C(C)C)=CC=C1CC1=CC=CC=C1N=C(C)C AMCDYMZKVGATAN-UHFFFAOYSA-N 0.000 description 1
- QWPWYWSMEUHNAR-UHFFFAOYSA-N n-[4-[[3,5-diethyl-4-(propan-2-ylideneamino)phenyl]methyl]-2,6-diethylphenyl]propan-2-imine Chemical compound CCC1=C(N=C(C)C)C(CC)=CC(CC=2C=C(CC)C(N=C(C)C)=C(CC)C=2)=C1 QWPWYWSMEUHNAR-UHFFFAOYSA-N 0.000 description 1
- IHIGZORFCDHTNA-UHFFFAOYSA-N n-[4-[[4-(3,3-dimethylbutan-2-ylideneamino)phenyl]methyl]phenyl]-3,3-dimethylbutan-2-imine Chemical compound C1=CC(N=C(C)C(C)(C)C)=CC=C1CC1=CC=C(N=C(C)C(C)(C)C)C=C1 IHIGZORFCDHTNA-UHFFFAOYSA-N 0.000 description 1
- UPTZAPWQVNBGPV-UHFFFAOYSA-N n-[4-[[4-(benzylideneamino)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]-1-phenylmethanimine Chemical compound C=1C(CC)=C(N=CC=2C=CC=CC=2)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N=CC1=CC=CC=C1 UPTZAPWQVNBGPV-UHFFFAOYSA-N 0.000 description 1
- YVCDJTPKTRESHF-UHFFFAOYSA-N n-[4-[[4-(butan-2-ylideneamino)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]butan-2-imine Chemical compound C1=C(CC)C(N=C(C)CC)=C(CC)C=C1CC1=CC(CC)=C(N=C(C)CC)C(CC)=C1 YVCDJTPKTRESHF-UHFFFAOYSA-N 0.000 description 1
- NDLJLXRPQAVQOO-UHFFFAOYSA-N n-[4-[[4-(cyclobutylideneamino)-3-methyl-5-propan-2-ylphenyl]methyl]-2-methyl-6-propan-2-ylphenyl]cyclobutanimine Chemical compound C=1C(C)=C(N=C2CCC2)C(C(C)C)=CC=1CC(C=C1C(C)C)=CC(C)=C1N=C1CCC1 NDLJLXRPQAVQOO-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- WWBKLTVZYOWOQX-UHFFFAOYSA-N n-[[3-[(pentylamino)methyl]cyclohexyl]methyl]pentan-1-amine Chemical compound CCCCCNCC1CCCC(CNCCCCC)C1 WWBKLTVZYOWOQX-UHFFFAOYSA-N 0.000 description 1
- FBVCLOFGMWMUDW-UHFFFAOYSA-N n-[[4-[(nonylamino)methyl]cyclohexyl]methyl]nonan-1-amine Chemical compound CCCCCCCCCNCC1CCC(CNCCCCCCCCC)CC1 FBVCLOFGMWMUDW-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-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
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 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
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000008096 xylene 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
- C08G18/70—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
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C211/09—Diamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C211/09—Diamines
- C07C211/12—1,6-Diaminohexanes
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C211/44—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 having amino groups bound to only one six-membered aromatic ring
- C07C211/49—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 having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C211/44—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 having amino groups bound to only one six-membered aromatic ring
- C07C211/49—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 having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—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 having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/324—Polyamines aromatic containing only one aromatic ring
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/325—Polyamines containing secondary or tertiary amino 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
- C08G18/70—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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/534,968 US7964695B2 (en) | 2005-03-28 | 2006-09-25 | Chain extenders |
| US11/534,968 | 2006-09-25 | ||
| PCT/US2007/068384 WO2008039571A1 (en) | 2006-09-25 | 2007-05-07 | Diamine chain extender compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007300409A1 AU2007300409A1 (en) | 2008-04-03 |
| AU2007300409B2 true AU2007300409B2 (en) | 2010-10-14 |
Family
ID=38567027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007300409A Ceased AU2007300409B2 (en) | 2006-09-25 | 2007-05-07 | Diamine chain extender compositions |
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) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2143707B1 (en) * | 2005-03-28 | 2018-04-11 | Line-X LLC | Secondary diamine |
| US8076518B2 (en) * | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| BRPI0809262A2 (pt) * | 2007-01-10 | 2014-10-07 | Albemarle Corp | Revestimento por aspersão; processo para formação de um revestimento por aspersão; artigo formado através da moldagem por injeção de reação; e processo para preparação de um produto de moldagem por injeção de reação. |
| 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 |
| WO2014144539A2 (en) * | 2013-03-15 | 2014-09-18 | 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 |
| 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 |
| WO2025224005A1 (en) * | 2024-04-25 | 2025-10-30 | Huntsman International Llc | Slow cure hybrid polyurea |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1070759A (en) * | 1964-02-13 | 1967-06-01 | Goodyear Tire & Rubber | Polyurethanes and method of making |
| EP0288067A1 (en) * | 1987-04-24 | 1988-10-26 | Asahi Glass Company Ltd. | Process for producing polyurethane elastomer and compositon as starting material therefor |
| US4798862A (en) * | 1986-08-01 | 1989-01-17 | Ici Americas Inc. | Polyureas prepared from a mixture of polyamines and polyisocyanate |
| US5008453A (en) * | 1989-04-14 | 1991-04-16 | Ethyl Corporation | Aromatic diimines |
| US5591807A (en) * | 1995-05-23 | 1997-01-07 | The Sherwin-Williams Company | Polyimine/polyisocyanate coating composition containing polymeric anhydride |
| DE19701835A1 (de) * | 1997-01-21 | 1998-07-23 | Huels Chemische Werke Ag | Kalthärtende, lösemittelarme oder lösemittelfreie Zweikomponenten-Polyurethan-Polyharnstoff-Massen |
| WO2002102869A1 (en) * | 2001-06-15 | 2002-12-27 | Huntsman Petrochemical Corporation | Synergistic amine chain-extenders in polyurea spray elastomers |
| US20030004265A1 (en) * | 2001-05-16 | 2003-01-02 | Gupta Laxmi C. | Polyurea coating composition |
| US20030036585A1 (en) * | 1997-06-13 | 2003-02-20 | 3M Innovative Properties Company | Liquid pavement marking compositions |
| WO2006028728A1 (en) * | 2004-09-02 | 2006-03-16 | Ppg Industries Ohio, Inc. | Composite films and process for making the same |
Family Cites Families (104)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE264014C (enExample) | 1913-09-09 | |||
| US2380420A (en) * | 1940-12-16 | 1945-07-31 | William S Emerson | Production of secondary and tertiary amines from nitrogen compounds |
| US2497292A (en) * | 1946-05-07 | 1950-02-14 | Du Pont | Preparation of n-isobutyl hexamethylenediamines |
| US2582128A (en) * | 1950-02-11 | 1952-01-08 | Rohm & Haas | Aldimines |
| US2953579A (en) * | 1958-05-07 | 1960-09-20 | Shell Oil Co | Epoxy aldimines |
| US2965605A (en) * | 1958-06-23 | 1960-12-20 | Shell Oil Co | Nu, nu'-dialkyl aromatic diamines |
| US3209030A (en) * | 1962-07-09 | 1965-09-28 | Universal Oil Prod Co | Reductive alkylation of amines |
| DE1163315B (de) | 1962-12-10 | 1964-02-20 | Bayer Ag | Verfahren zur Herstellung von Trihalogenessigsaeureimidchloriden |
| NL127232C (enExample) * | 1963-03-12 | 1900-01-01 | ||
| US3275567A (en) * | 1963-06-27 | 1966-09-27 | Engelhard Ind Inc | Method of preparing a sulfided platinum on carbon catalyst |
| US3350450A (en) * | 1963-08-12 | 1967-10-31 | Uniroyal Inc | Process of preparing aromatic amines by the catalytic hydrogenation of aromatic nitro compounds |
| BR6569895D0 (pt) * | 1964-05-25 | 1973-12-27 | C Summers | Aperfeicoamento em processo para a producao de iminas e em processo de alcoilacao redutiva para a producao de aminas secunda rias |
| CH481963A (de) * | 1967-06-08 | 1969-11-30 | Ciba Geigy | Neue härtbare Mischungen aus Diepoxydverbindungen, disekundären Aminen sowie mindestens 3 Aminwasserstoffatome enthaltenden Polyaminen |
| US3538161A (en) * | 1967-10-20 | 1970-11-03 | Uniroyal Inc | Reductive alkylation of aromatic amino compounds utilizing platinum metal selendies and tellurides as catalysts |
| SU387551A3 (enExample) | 1968-03-18 | 1973-06-21 | ||
| US3625710A (en) * | 1969-06-25 | 1971-12-07 | Procter & Gamble | Aldimines as chocolate-like flavors |
| NL7011639A (enExample) * | 1969-08-11 | 1971-02-15 | ||
| US3943158A (en) * | 1970-07-01 | 1976-03-09 | Bayer Aktiengesellschaft | Urea diisocyanate compositions |
| US3761425A (en) | 1971-02-19 | 1973-09-25 | Hoechst Ag | Process for preparing sulfided platinum on carbon catalysts |
| US3952056A (en) * | 1972-02-07 | 1976-04-20 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US3937730A (en) * | 1972-06-06 | 1976-02-10 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US3994975A (en) * | 1974-10-07 | 1976-11-30 | Petrolite Corporation | Cyclohexylamines |
| US4161492A (en) * | 1975-01-24 | 1979-07-17 | Bayer Aktiengesellschaft | Cycloaliphatic amines and process for preparing same |
| DE2503261C2 (de) | 1975-01-28 | 1976-12-30 | Ruhrchemie Ag | Verfahren zur sulfidierung von platin-auf-kohlenstoff-katalysatoren |
| DE2525295C3 (de) * | 1975-06-06 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Azomethinen |
| US4140718A (en) * | 1976-10-14 | 1979-02-20 | Uop Inc. | Preparation of N,N'-dialkylphenylenediamines |
| ZA80701B (en) | 1979-02-21 | 1981-02-25 | Uniroyal Inc | Trialkylamine preparation by reductive alkylation of dialkylamines with ketones |
| US4317916A (en) * | 1979-04-16 | 1982-03-02 | Ciba-Geigy Corporation | Process for producing N-substituted-N-acetyl-2,6-dialkyl-anilines |
| DE2940738A1 (de) | 1979-10-08 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls zellhaltigen polyurethan-polyharnstoff-formkoerpern |
| JPS6033423B2 (ja) * | 1980-08-13 | 1985-08-02 | 宇部興産株式会社 | N−アルキルアルキレンジアミンの製法 |
| DE3126435A1 (de) | 1981-07-04 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls zelligen polyurethan-polyharnstoff-formkoerpern und alkylsubstituierte phenylendiamine hierzu |
| US4900868A (en) * | 1982-01-18 | 1990-02-13 | Monsanto Company | Process for producing N,N'-disubstituted paraphenylene diamine mixtures by sequential reductive alkylation |
| DE3232736A1 (de) * | 1982-09-03 | 1984-03-08 | Bayer Ag, 5090 Leverkusen | Aromatische uretdion-di-harnstoff-diamine, verfahren zu ihrer herstellung und ihre verwendung bei der polyurethansynthese |
| JPS59155470A (ja) * | 1983-02-23 | 1984-09-04 | Kansai Paint Co Ltd | 熱硬化性塗料用樹脂組成物 |
| US4521624A (en) * | 1984-04-16 | 1985-06-04 | Ethyl Corporation | Process for making cyclic amines |
| US4714512A (en) * | 1985-03-25 | 1987-12-22 | Uop Inc. | Polyurethane coatings and adhesives |
| US4578446A (en) * | 1985-03-25 | 1986-03-25 | Uop Inc. | Secondary aromatic diamines as curing agents in polyurethane manufacturing |
| DE3528262A1 (de) * | 1985-08-07 | 1987-02-12 | Hoechst Ag | Verfahren zur herstellung aromatischer dialkylamine |
| US4631298A (en) * | 1985-12-16 | 1986-12-23 | Ethyl Corporation | Mixed diamine chain extender |
| US4663201A (en) * | 1986-04-25 | 1987-05-05 | Uop Inc. | Polyurea coatings for objects of metal glass wood or plastic |
| JPS6352146A (ja) | 1986-08-22 | 1988-03-05 | Konica Corp | 正帯電用電子写真感光体 |
| DE3710432A1 (de) * | 1987-03-28 | 1988-10-06 | Basf Ag | Polyamid- und polyharnstoffgruppen gebunden enthaltende elastomere sowie verfahren zur herstellung von elastischen, kompakten oder zelligen formkoerpern hieraus |
| DE3728141A1 (de) | 1987-08-22 | 1989-03-02 | Bayer Ag | Katalysator |
| DD264014A1 (de) | 1987-08-27 | 1989-01-18 | Zeiss Jena Veb Carl | Epoxid/amin-(meth)acrylat-klebstoffe |
| EP0309980A1 (en) | 1987-10-02 | 1989-04-05 | The B.F. Goodrich Company | Alkylated polyalkylene polyamines and process for selective alkylation |
| DE3739480A1 (de) * | 1987-11-21 | 1989-06-01 | Huels Chemische Werke Ag | Verfahren zur herstellung von blockierten harnstoffgruppenhaltigen polyisocyanaten sowie die danach hergestellten produkte |
| US4806616A (en) * | 1987-12-09 | 1989-02-21 | Uop Inc. | N-N'-dialkylphenylenediamines as curing agents in polyurethane and polyurea manufacture by reaction injection molding |
| US5001267A (en) * | 1987-12-21 | 1991-03-19 | Texaco Chemical Company | Secondary alkyl amine derivatives of ethylenediamine |
| US5041668A (en) * | 1989-04-14 | 1991-08-20 | Ethyl Corporation | Secondary diamines |
| EP0420426A3 (en) | 1989-09-29 | 1991-09-04 | Texaco Chemical Company | Sprayable and pourable polyurea elastomer |
| DE4000014A1 (de) * | 1990-01-02 | 1991-07-04 | Basf Ag | Verfahren zur herstellung von elastischen, kompakten oder zelligen formkoerpern auf der grundlage von n-substituierte harnstoff- und amidgruppen gebunden enthaltenden elastomere derartige und hierfuer geeignete inhaltige polyoxyalkylen-polyamin-mischungen |
| US5002806A (en) * | 1990-01-11 | 1991-03-26 | Ashland Oil, Inc. | Curative for structural urethane adhesive |
| US5082917A (en) * | 1990-05-29 | 1992-01-21 | Texaco Chemical Co. | Piperazine derivatives as chain extenders in polyurea elastomer systems and method making same |
| US5059672A (en) * | 1990-06-25 | 1991-10-22 | Thare Coat, Inc. | Elastomeric reaction products of aromatic isocyanate, aliphatic isocyanate and aromatic diamine components |
| US5087661A (en) | 1990-07-20 | 1992-02-11 | Mitsui Toatsu Chemicals, Inc. | Moisture curable polyurethane composition comprising polyaldimine |
| US5145825A (en) * | 1991-04-08 | 1992-09-08 | Engelhard Corporation | Oxidation catalyst resistant to sulfation |
| US5198524A (en) | 1991-04-22 | 1993-03-30 | W.R. Grace & Co.-Conn. | Moisture-curing acrylate/epoxy hybrid adhesives |
| JPH05274914A (ja) | 1992-03-25 | 1993-10-22 | Hitachi Chem Co Ltd | 絶縁材料 |
| MY109091A (en) * | 1992-12-29 | 1996-11-30 | Syngenta Participations Ag | Process for the preparation of 2-alkyl-6-methyl-n-(1''''''''- methoxy-2''''''''-propyl)-aniline and a process for the preparation of their chloracetanilides. |
| TW322432B (enExample) * | 1993-06-14 | 1997-12-11 | Degussa | |
| US5312886A (en) * | 1993-09-20 | 1994-05-17 | Uop | Bis(N-alkylaminocyclohexyl)methanes as curing agents for polyurethanes and polyureas |
| DE4406949A1 (de) * | 1994-03-03 | 1995-09-07 | Bayer Ag | Verfahren zur Herstellung von aliphatischen Iminen |
| DE4413618A1 (de) * | 1994-04-19 | 1995-10-26 | Hoechst Ag | Verfahren zur Herstellung von Glykoloylaniliden |
| US5470890A (en) * | 1994-06-17 | 1995-11-28 | Uop | Bis-(N-alkylaminocyclohexyl)methanes as curing agents in polyurethane and polyurea flexible foam manufacture |
| CA2151672C (en) | 1994-06-24 | 2007-05-29 | Dudley Joseph Ii Primeaux | Preparation of sprayable aliphatic polyurea elastomers having improved properties |
| US5616790A (en) * | 1994-11-18 | 1997-04-01 | California Institute Of Technology | Lipid-based metal sensor |
| US5646235A (en) * | 1995-03-27 | 1997-07-08 | Huntsman Petrochemical Corporation | Reductive alkylation of polyamines |
| JPH09100260A (ja) | 1995-04-13 | 1997-04-15 | Nippon Kayaku Co Ltd | 4,4′−ジ(n−アルキルアニリン)類の製造方法 |
| JPH11508557A (ja) | 1995-06-28 | 1999-07-27 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | ケチミン硬化剤ならびにケチミンを用いて作製された迅速硬化性の磁気記録媒体およびフィルム |
| DE19546750A1 (de) | 1995-12-14 | 1997-06-19 | Huels Chemische Werke Ag | Uretdiongruppenhaltige Polyadditionsprodukte sowie deren Herstellung |
| US5731397A (en) | 1996-04-16 | 1998-03-24 | Huntman Petrochemical Corporation | Polyurea spray railcar lining systems |
| DE19637375A1 (de) * | 1996-09-13 | 1998-03-19 | Huels Chemische Werke Ag | Uretdiongruppenhaltige Polyisocyanate, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| DE19637377A1 (de) * | 1996-09-13 | 1998-03-19 | Huels Chemische Werke Ag | Uretdiongruppenhaltige Polyadditionsverbindungen, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| US6399736B1 (en) * | 1997-03-11 | 2002-06-04 | Huntsman Petrochemical Corporation | Method of preparing spray elastomer systems |
| US6013755A (en) * | 1997-03-11 | 2000-01-11 | Huntsman Petrochemical Corporation | Method of preparing an aliphatic polyurea spray elastomer system |
| US6218480B1 (en) * | 1997-06-16 | 2001-04-17 | Mmr Technologies, Inc. | Water-compatible urethane-containing amine hardener |
| US6103799A (en) | 1998-01-20 | 2000-08-15 | Air Products And Chemicals, Inc. | Surface tension reduction with N,N'-dialkylalkylenediamines |
| US5874619A (en) * | 1998-04-07 | 1999-02-23 | Albemarle Corporation | Reducing the coloration of aromatic diamines |
| DE19816547A1 (de) * | 1998-04-15 | 1999-10-21 | Degussa | Harnstoff- und uretdiongruppenhaltige Polyisocyanate |
| WO2000026181A1 (de) | 1998-10-30 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Verfahren zur herstellung von ketiminen |
| AUPP991799A0 (en) * | 1999-04-23 | 1999-05-20 | Cardiac Crc Nominees Pty Limited | Siloxane-containing polyurethane-urea compositions |
| EP1067116A1 (en) | 1999-07-09 | 2001-01-10 | The Procter & Gamble Company | Process for the production of imines |
| AU1306401A (en) | 1999-11-11 | 2001-05-30 | Idemitsu Petrochemical Co., Ltd. | Transition metal compound, olefin polymerization catalyst, and method of polymerizing olefin |
| DE10002089A1 (de) * | 2000-01-19 | 2001-07-26 | Basf Ag | Witterungsstabile, strahlungshärtbare Polyurethane |
| US6403752B1 (en) * | 2000-07-17 | 2002-06-11 | Uop Llc | Secondary aliphatic diamines as curing agents for polyurethanes and polyureas prepared using high-pressure impingement mixing |
| US6803445B2 (en) * | 2001-08-08 | 2004-10-12 | The Yokohama Rubber Co., Ltd. | Moisture curable polyurethane and/or epoxy resin composition and storage stabilizer contained therein |
| AUPR732601A0 (en) | 2001-08-28 | 2001-09-20 | Polychip Pharmaceuticals Pty Ltd | Methods for the synthesis of amines such as ephedrine and inter mediates |
| CN1169844C (zh) | 2001-12-10 | 2004-10-06 | 中国科学院长春应用化学研究所 | 双核镍烯烃聚合催化剂 |
| US6831187B2 (en) * | 2001-12-18 | 2004-12-14 | Univation Technologies, Llc | Multimetallic catalyst compositions for the polymerization of olefins |
| US6429338B1 (en) * | 2002-01-17 | 2002-08-06 | Air Products And Chemicals, Inc. | Hydrogenation of single ring aromatic diamines |
| US20040015016A1 (en) * | 2002-07-22 | 2004-01-22 | Huntsman Petrochemical Corporation | Preparation of secondary amines |
| CA2515780C (en) | 2003-02-20 | 2012-12-11 | Encysive Pharmaceuticals Inc. | Phenylenediamine urotensin-ii receptor antagonists and ccr-9 antagonists |
| US6939939B2 (en) * | 2003-02-24 | 2005-09-06 | Younger Mfg. | Polyurea/urethane optical material and method for making it |
| US7045632B2 (en) * | 2003-03-04 | 2006-05-16 | Chevron Phillips Chemical Company, Lp | Composition and method for a hexadentate ligand and bimetallic complex for polymerization of olefins |
| US20040197472A1 (en) | 2003-04-04 | 2004-10-07 | Scofield Harry J. | Process and apparatus for sealing freezer enclosures from moisture and contamination |
| GB0323213D0 (en) | 2003-10-03 | 2003-11-05 | Univ Warwick | Metallo-supramolecular arrays as anti-cancer and anti-viral agent |
| US8076518B2 (en) * | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| EP2143707B1 (en) * | 2005-03-28 | 2018-04-11 | Line-X LLC | Secondary diamine |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| US20070066786A1 (en) * | 2005-09-22 | 2007-03-22 | The Hanson Group, Llc | Methods of preparing and using polyurea elastomers |
| US9856355B2 (en) | 2005-09-27 | 2018-01-02 | Evonik Degussa Gmbh | Silanol-functionalized compounds for the preparation of polyurethane foams |
| DE102005046641B4 (de) | 2005-09-29 | 2019-08-22 | Tib Chemicals Ag | Verfahren zum Schutz der Aussenflächen von metallischen Werkstoffen gegen Korrosion durch Beschichtung mit härtbaren Mischungen auf der Basis von Glycidylverbindungen und aminischen Härtern |
| US20070100112A1 (en) | 2005-10-27 | 2007-05-03 | Bayer Materialscience Llc | Polyurethane-urea elastomers |
| CN100439414C (zh) | 2006-09-30 | 2008-12-03 | 北京展辰化工有限公司 | 低游离tdi聚氨酯固化剂的制造方法、制得的固化剂及其制品 |
-
2006
- 2006-09-25 US US11/534,968 patent/US7964695B2/en not_active Expired - Fee Related
-
2007
- 2007-05-07 WO PCT/US2007/068384 patent/WO2008039571A1/en not_active Ceased
- 2007-05-07 BR BRPI0716043-7A patent/BRPI0716043A2/pt not_active IP Right Cessation
- 2007-05-07 KR KR1020097005110A patent/KR20090074159A/ko not_active Withdrawn
- 2007-05-07 JP JP2009529282A patent/JP2010504400A/ja active Pending
- 2007-05-07 CN CN2007800354095A patent/CN101516948B/zh not_active Expired - Fee Related
- 2007-05-07 CA CA002661513A patent/CA2661513A1/en not_active Abandoned
- 2007-05-07 AU AU2007300409A patent/AU2007300409B2/en not_active Ceased
- 2007-05-07 EP EP07783397A patent/EP2078048A1/en not_active Withdrawn
- 2007-05-07 EA EA200970324A patent/EA017131B1/ru not_active IP Right Cessation
-
2011
- 2011-02-16 US US13/028,579 patent/US8080626B2/en not_active Expired - Fee Related
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1070759A (en) * | 1964-02-13 | 1967-06-01 | Goodyear Tire & Rubber | Polyurethanes and method of making |
| US4798862A (en) * | 1986-08-01 | 1989-01-17 | Ici Americas Inc. | Polyureas prepared from a mixture of polyamines and polyisocyanate |
| EP0288067A1 (en) * | 1987-04-24 | 1988-10-26 | Asahi Glass Company Ltd. | Process for producing polyurethane elastomer and compositon as starting material therefor |
| US5008453A (en) * | 1989-04-14 | 1991-04-16 | Ethyl Corporation | Aromatic diimines |
| US5591807A (en) * | 1995-05-23 | 1997-01-07 | The Sherwin-Williams Company | Polyimine/polyisocyanate coating composition containing polymeric anhydride |
| DE19701835A1 (de) * | 1997-01-21 | 1998-07-23 | Huels Chemische Werke Ag | Kalthärtende, lösemittelarme oder lösemittelfreie Zweikomponenten-Polyurethan-Polyharnstoff-Massen |
| US20030036585A1 (en) * | 1997-06-13 | 2003-02-20 | 3M Innovative Properties Company | Liquid pavement marking compositions |
| US20030004265A1 (en) * | 2001-05-16 | 2003-01-02 | Gupta Laxmi C. | Polyurea coating composition |
| WO2002102869A1 (en) * | 2001-06-15 | 2002-12-27 | Huntsman Petrochemical Corporation | Synergistic amine chain-extenders in polyurea spray elastomers |
| WO2006028728A1 (en) * | 2004-09-02 | 2006-03-16 | Ppg Industries Ohio, Inc. | Composite films and process for making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070270566A1 (en) | 2007-11-22 |
| BRPI0716043A2 (pt) | 2013-01-08 |
| US8080626B2 (en) | 2011-12-20 |
| CN101516948A (zh) | 2009-08-26 |
| US7964695B2 (en) | 2011-06-21 |
| EP2078048A1 (en) | 2009-07-15 |
| WO2008039571A1 (en) | 2008-04-03 |
| AU2007300409A1 (en) | 2008-04-03 |
| EA017131B1 (ru) | 2012-10-30 |
| KR20090074159A (ko) | 2009-07-06 |
| CA2661513A1 (en) | 2008-04-03 |
| JP2010504400A (ja) | 2010-02-12 |
| CN101516948B (zh) | 2012-08-15 |
| US20110137005A1 (en) | 2011-06-09 |
| EA200970324A1 (ru) | 2009-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2007300409B2 (en) | Diamine chain extender compositions | |
| AU2003262972A1 (en) | Polyether polyamine agents and mixtures therefor | |
| AU2007300253B2 (en) | Chain extenders | |
| US8143365B2 (en) | Formulations for reaction injection molding and for spray systems | |
| EP2157110B1 (en) | Mixed polycycloaliphatic amines (MPCA) and MPCA alkylates as curatives for polyisocyanates | |
| WO2008112636A1 (en) | Chain extenders | |
| WO2024145439A1 (en) | Polyurea and method of making using an amine compound | |
| KR102123893B1 (ko) | 아민 기능성 모노아스파르틱 에스테르기를 함유한 이민계 사슬연장제 조성물 및 이를 포함하는 탄성체 조성물 | |
| KR102123894B1 (ko) | 아민 기능성 모노아스파르틱 에스테르기를 함유한 이민계 가교제 조성물 및 이를 포함하는 탄성체 조성물 | |
| US20080262187A1 (en) | Blends of Diamines Having Reduced Color | |
| WO2008039715A1 (en) | Chain extenders |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |