KR20090071513A - 사슬 연장제 - Google Patents
사슬 연장제 Download PDFInfo
- Publication number
- KR20090071513A KR20090071513A KR1020087026907A KR20087026907A KR20090071513A KR 20090071513 A KR20090071513 A KR 20090071513A KR 1020087026907 A KR1020087026907 A KR 1020087026907A KR 20087026907 A KR20087026907 A KR 20087026907A KR 20090071513 A KR20090071513 A KR 20090071513A
- Authority
- KR
- South Korea
- Prior art keywords
- diamine
- aliphatic
- diamines
- aliphatic secondary
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000004970 Chain extender Substances 0.000 title claims abstract description 37
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 119
- 150000004985 diamines Chemical group 0.000 claims abstract description 99
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 29
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 18
- 150000003077 polyols Chemical class 0.000 claims description 18
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 14
- 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 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 10
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical group CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 125000002312 hydrocarbylidene group Chemical group 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 4
- 229910000071 diazene Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000004427 diamine group Chemical group 0.000 claims 24
- 229920002396 Polyurea Polymers 0.000 abstract description 18
- 229920002635 polyurethane Polymers 0.000 abstract description 15
- 239000004814 polyurethane Substances 0.000 abstract description 15
- -1 aliphatic diamines Chemical class 0.000 description 23
- 239000000126 substance Substances 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 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
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000003118 aryl group Chemical group 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
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 239000000463 material Substances 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
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- GTKFREDCXXGRMN-UHFFFAOYSA-N 1-cyclobutyl-n-[4-(1-cyclobutylethylideneamino)cyclohexyl]ethanimine Chemical compound C1CCC1C(C)=NC(CC1)CCC1N=C(C)C1CCC1 GTKFREDCXXGRMN-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
- 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
- GJJBLVIGIOFBDJ-UHFFFAOYSA-N 1-n,3-n-dicyclohexylcyclohexane-1,3-diamine Chemical compound C1CCCCC1NC1CC(NC2CCCCC2)CCC1 GJJBLVIGIOFBDJ-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
- 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
- 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
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- OCEYGOKEUYVKGO-UHFFFAOYSA-N 3-methyl-n-[2-[(3-methylcyclohex-2-en-1-ylidene)amino]propyl]cyclohex-2-en-1-imine Chemical compound C1CCC(C)=CC1=NC(C)CN=C1CCCC(C)=C1 OCEYGOKEUYVKGO-UHFFFAOYSA-N 0.000 description 1
- BMRZDCMBELSVGA-UHFFFAOYSA-N 4,6-diethyl-2-methylcyclohexane-1,3-diamine Chemical compound CCC1CC(CC)C(N)C(C)C1N BMRZDCMBELSVGA-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
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001575980 Mendoza Species 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- MPYOXCAHVAWKKU-UHFFFAOYSA-N ethanamine tricyclo[5.2.1.02,6]decane Chemical compound CCN.CCN.C1CC2C3CCC(C3)C2C1 MPYOXCAHVAWKKU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002334 glycols Chemical class 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
- 239000012760 heat stabilizer Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-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
- 150000002466 imines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- ARBOHFITIICHFH-UHFFFAOYSA-N n,n'-bis(1-cyclopropylethyl)pentane-1,5-diamine Chemical compound C1CC1C(C)NCCCCCNC(C)C1CC1 ARBOHFITIICHFH-UHFFFAOYSA-N 0.000 description 1
- RLXUAEUYPUKKNB-UHFFFAOYSA-N n,n'-bis(2,5-dimethylcyclopentyl)butane-1,4-diamine Chemical compound CC1CCC(C)C1NCCCCNC1C(C)CCC1C RLXUAEUYPUKKNB-UHFFFAOYSA-N 0.000 description 1
- HGLSFWZWRNSPNZ-UHFFFAOYSA-N n,n'-bis(3,3-dimethylbutan-2-yl)-2-methylpentane-1,5-diamine Chemical compound CC(C)(C)C(C)NCC(C)CCCNC(C)C(C)(C)C HGLSFWZWRNSPNZ-UHFFFAOYSA-N 0.000 description 1
- HBDXMESKEKYWMT-UHFFFAOYSA-N n,n'-bis(but-2-enyl)propane-1,3-diamine Chemical compound CC=CCNCCCNCC=CC HBDXMESKEKYWMT-UHFFFAOYSA-N 0.000 description 1
- QKRHUNNQVRLNBN-UHFFFAOYSA-N n,n'-di(butan-2-yl)hexane-1,6-diamine Chemical compound CCC(C)NCCCCCCNC(C)CC QKRHUNNQVRLNBN-UHFFFAOYSA-N 0.000 description 1
- ZRSMNEWSFHELIS-UHFFFAOYSA-N n,n'-di(butan-2-yl)octane-1,8-diamine Chemical compound CCC(C)NCCCCCCCCNC(C)CC ZRSMNEWSFHELIS-UHFFFAOYSA-N 0.000 description 1
- VXOZMGMHXFBFLV-UHFFFAOYSA-N n,n'-di(hexan-3-yl)dodecane-1,12-diamine Chemical compound CCCC(CC)NCCCCCCCCCCCCNC(CC)CCC VXOZMGMHXFBFLV-UHFFFAOYSA-N 0.000 description 1
- OYVRGZCAZZFVPI-UHFFFAOYSA-N n,n'-di(pentan-2-yl)decane-1,10-diamine Chemical compound CCCC(C)NCCCCCCCCCCNC(C)CCC OYVRGZCAZZFVPI-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
- JDATUVOTFKQHGU-UHFFFAOYSA-N n,n'-di(propan-2-yl)heptane-1,7-diamine Chemical compound CC(C)NCCCCCCCNC(C)C JDATUVOTFKQHGU-UHFFFAOYSA-N 0.000 description 1
- LDVAQIQJUVHMIN-UHFFFAOYSA-N n-[10-(pentan-2-ylideneamino)decyl]pentan-2-imine Chemical compound CCCC(C)=NCCCCCCCCCCN=C(C)CCC LDVAQIQJUVHMIN-UHFFFAOYSA-N 0.000 description 1
- NYUMCTQXUNDLRG-UHFFFAOYSA-N n-[12-(hexan-3-ylideneamino)dodecyl]hexan-3-imine Chemical compound CCCC(CC)=NCCCCCCCCCCCCN=C(CC)CCC NYUMCTQXUNDLRG-UHFFFAOYSA-N 0.000 description 1
- OBCUCYFDXXOOQC-UHFFFAOYSA-N n-[2,5-dimethyl-5-(pentan-3-ylideneamino)hexan-2-yl]pentan-3-imine Chemical compound CCC(CC)=NC(C)(C)CCC(C)(C)N=C(CC)CC OBCUCYFDXXOOQC-UHFFFAOYSA-N 0.000 description 1
- XYUPSAQDSQCJQV-UHFFFAOYSA-N n-[2-(butan-2-ylideneamino)propyl]butan-2-imine Chemical compound CCC(C)=NCC(C)N=C(C)CC XYUPSAQDSQCJQV-UHFFFAOYSA-N 0.000 description 1
- PQRAATAFIIHXJR-UHFFFAOYSA-N n-[2-(hexan-3-ylideneamino)cyclohexyl]hexan-3-imine Chemical compound CCCC(CC)=NC1CCCCC1N=C(CC)CCC PQRAATAFIIHXJR-UHFFFAOYSA-N 0.000 description 1
- KWAQMTIQRQEKCQ-UHFFFAOYSA-N n-[2-(propan-2-ylideneamino)ethyl]propan-2-imine Chemical compound CC(C)=NCCN=C(C)C KWAQMTIQRQEKCQ-UHFFFAOYSA-N 0.000 description 1
- IUXQSEOMZZVAJQ-UHFFFAOYSA-N n-[2-(undecylideneamino)cyclohexyl]undecan-1-imine Chemical compound CCCCCCCCCCC=NC1CCCCC1N=CCCCCCCCCCC IUXQSEOMZZVAJQ-UHFFFAOYSA-N 0.000 description 1
- HRCUMKIOUKAEPZ-UHFFFAOYSA-N n-[3-(but-2-enylideneamino)propyl]but-2-en-1-imine Chemical compound CC=CC=NCCCN=CC=CC HRCUMKIOUKAEPZ-UHFFFAOYSA-N 0.000 description 1
- LWUJZQSGZUNVBG-UHFFFAOYSA-N n-[3-(cyclohexylideneamino)cyclohexyl]cyclohexanimine Chemical compound C1CCCCC1=NC1CC(N=C2CCCCC2)CCC1 LWUJZQSGZUNVBG-UHFFFAOYSA-N 0.000 description 1
- MDDBUAXOAOFRET-UHFFFAOYSA-N n-[4-[(2,5-dimethylcyclopentylidene)amino]butyl]-2,5-dimethylcyclopentan-1-imine Chemical compound CC1CCC(C)C1=NCCCCN=C1C(C)CCC1C MDDBUAXOAOFRET-UHFFFAOYSA-N 0.000 description 1
- IEKLTHXMJBNIHV-UHFFFAOYSA-N n-[5-(3,3-dimethylbutan-2-ylideneamino)-4-methylpentyl]-3,3-dimethylbutan-2-imine Chemical compound CC(C)(C)C(C)=NCC(C)CCCN=C(C)C(C)(C)C IEKLTHXMJBNIHV-UHFFFAOYSA-N 0.000 description 1
- COEITCNWTMGMTR-UHFFFAOYSA-N n-[6-(butan-2-ylideneamino)hexyl]butan-2-imine Chemical compound CCC(C)=NCCCCCCN=C(C)CC COEITCNWTMGMTR-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000005060 rubber Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- 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
-
- 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
- C07C211/53—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 the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- 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
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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
- 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
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic 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
- C08G18/70—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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
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| US11/534,980 US8076518B2 (en) | 2005-03-28 | 2006-09-25 | Chain extenders |
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| KR20090071513A true KR20090071513A (ko) | 2009-07-01 |
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| KR1020087026907A Ceased KR20090071513A (ko) | 2006-09-25 | 2007-09-21 | 사슬 연장제 |
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| US (1) | US8076518B2 (https=) |
| EP (1) | EP2066715A1 (https=) |
| JP (1) | JP2010504411A (https=) |
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| CN (1) | CN101516944A (https=) |
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| EA (1) | EA016982B1 (https=) |
| WO (1) | WO2008039699A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| RU2007139697A (ru) * | 2005-03-28 | 2009-05-10 | Альбемарл Корпорейшн (Us) | Диимины и вторичные диамины |
| EP2102265A1 (en) * | 2007-01-10 | 2009-09-23 | Albermarle Corporation | Formulations for reaction injection molding and for spray systems |
| FR2927903B1 (fr) * | 2008-02-25 | 2011-02-18 | Seppic Sa | Nouveaux allongeurs de chaines pour formulations d'elastomeres de polyurethanes. |
| FR2979912A1 (fr) | 2011-09-08 | 2013-03-15 | Seppic Sa | Amelioration des proprietes physiques de polymeres polyurethanes |
| US12559592B2 (en) * | 2020-04-15 | 2026-02-24 | 3M Innovative Properties Company | Branched amorphous polyamide (co)polymers and methods of making and using same |
Family Cites Families (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2380420A (en) | 1940-12-16 | 1945-07-31 | William S Emerson | Production of secondary and tertiary amines from nitrogen compounds |
| 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 (https=) | 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 |
| GB1070759A (en) | 1964-02-13 | 1967-06-01 | Goodyear Tire & Rubber | Polyurethanes and method of making |
| GB1107336A (en) | 1964-05-25 | 1968-03-27 | Monsanto Co | Condensation of amines with aldehydes and ketones |
| 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 (https=) | 1968-03-18 | 1973-06-21 | ||
| US3625710A (en) | 1969-06-25 | 1971-12-07 | Procter & Gamble | Aldimines as chocolate-like flavors |
| NL7011639A (https=) | 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 |
| 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 |
| DE3528262A1 (de) | 1985-08-07 | 1987-02-12 | Hoechst Ag | Verfahren zur herstellung aromatischer dialkylamine |
| CH666260A5 (de) * | 1985-10-23 | 1988-07-15 | Lonza Ag | Substituierte p,p'-methylen-bis-aniline und deren verwendung als kettenverlaengerungsmittel oder vernetzungsmittel fuer polyurethane. |
| 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 |
| EP0288067A1 (en) | 1987-04-24 | 1988-10-26 | Asahi Glass Company Ltd. | Process for producing polyurethane elastomer and compositon as starting material therefor |
| DE3728141A1 (de) | 1987-08-22 | 1989-03-02 | Bayer Ag | Katalysator |
| 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 |
| US5008453A (en) | 1989-04-14 | 1991-04-16 | Ethyl Corporation | Aromatic diimines |
| 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 |
| US5002806A (en) * | 1990-01-11 | 1991-03-26 | Ashland Oil, Inc. | Curative for structural urethane adhesive |
| 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 (https=) | 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 |
| 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 |
| US5591807A (en) | 1995-05-23 | 1997-01-07 | The Sherwin-Williams Company | Polyimine/polyisocyanate coating composition containing polymeric anhydride |
| KR19990028421A (ko) | 1995-06-28 | 1999-04-15 | 스프레이그 로버트 월터 | 케트이민 경화제 및 케트이민으로 제조된 신속하게 경화되는 자기 기록 매체 및 필름 |
| 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 |
| DE19637377A1 (de) | 1996-09-13 | 1998-03-19 | Huels Chemische Werke Ag | Uretdiongruppenhaltige Polyadditionsverbindungen, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| DE19637375A1 (de) | 1996-09-13 | 1998-03-19 | Huels Chemische Werke Ag | Uretdiongruppenhaltige Polyisocyanate, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| DE19701835A1 (de) * | 1997-01-21 | 1998-07-23 | Huels Chemische Werke Ag | Kalthärtende, lösemittelarme oder lösemittelfreie Zweikomponenten-Polyurethan-Polyharnstoff-Massen |
| US6013755A (en) | 1997-03-11 | 2000-01-11 | Huntsman Petrochemical Corporation | Method of preparing an aliphatic polyurea spray elastomer system |
| US6399736B1 (en) | 1997-03-11 | 2002-06-04 | Huntsman Petrochemical Corporation | Method of preparing spray elastomer systems |
| EP0988333B1 (en) | 1997-06-13 | 2006-03-15 | Minnesota Mining And Manufacturing Company | Liquid pavement marking compositions |
| 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 |
| DE19816547A1 (de) | 1998-04-15 | 1999-10-21 | Degussa | Harnstoff- und uretdiongruppenhaltige Polyisocyanate |
| CN1325381A (zh) | 1998-10-30 | 2001-12-05 | 西巴特殊化学品控股有限公司 | 酮亚胺的制备方法 |
| EP1645580A3 (de) * | 1999-03-12 | 2007-03-28 | Basf Aktiengesellschaft | Polyharnstoffe |
| 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 |
| JP4659322B2 (ja) | 1999-11-11 | 2011-03-30 | 出光興産株式会社 | 遷移金属化合物、オレフィン重合触媒及びオレフィンの重合方法 |
| US7211624B2 (en) * | 1999-12-03 | 2007-05-01 | Acushnet Company | Golf ball layers formed of polyurethane-based and polyurea-based compositions incorporating block copolymers |
| 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 |
| US7001948B2 (en) * | 2001-05-16 | 2006-02-21 | American Polymer Corporation | Polyurea coating compositions |
| US20030004265A1 (en) | 2001-05-16 | 2003-01-02 | Gupta Laxmi C. | Polyurea coating composition |
| MXPA03011419A (es) | 2001-06-15 | 2004-06-30 | Huntsman Spec Chem Corp | Extensores sinergicos de cadena de amina en elastomeros de rocio de poliurea. |
| 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 |
| US7319111B2 (en) | 2003-02-20 | 2008-01-15 | Encysive Pharmaceuticals, Inc. | Phenylenediamine Urotensin-II receptor antagonists and CCR-9 antagonists |
| 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 |
| US20070043197A1 (en) * | 2003-07-07 | 2007-02-22 | Huntsman Petrochemical Corporation | Polyurea polymers from secondary polyether polyamines |
| GB0323213D0 (en) | 2003-10-03 | 2003-11-05 | Univ Warwick | Metallo-supramolecular arrays as anti-cancer and anti-viral agent |
| US20060068198A1 (en) | 2004-09-02 | 2006-03-30 | Bratys Dan M | Composite films and process for making the same |
| RU2007139697A (ru) | 2005-03-28 | 2009-05-10 | Альбемарл Корпорейшн (Us) | Диимины и вторичные диамины |
| 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 |
| 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 |
| 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 US11/534,980 patent/US8076518B2/en active Active
-
2007
- 2007-09-21 JP JP2009529412A patent/JP2010504411A/ja active Pending
- 2007-09-21 CN CNA2007800321710A patent/CN101516944A/zh active Pending
- 2007-09-21 WO PCT/US2007/079170 patent/WO2008039699A1/en not_active Ceased
- 2007-09-21 EA EA200870346A patent/EA016982B1/ru not_active IP Right Cessation
- 2007-09-21 EP EP07842972A patent/EP2066715A1/en not_active Withdrawn
- 2007-09-21 AU AU2007300253A patent/AU2007300253B2/en not_active Ceased
- 2007-09-21 CA CA002649230A patent/CA2649230A1/en not_active Abandoned
- 2007-09-21 KR KR1020087026907A patent/KR20090071513A/ko not_active Ceased
- 2007-09-21 BR BRPI0710717-0A patent/BRPI0710717A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007300253B2 (en) | 2011-10-13 |
| CN101516944A (zh) | 2009-08-26 |
| CA2649230A1 (en) | 2008-04-03 |
| US20070073030A1 (en) | 2007-03-29 |
| BRPI0710717A2 (pt) | 2011-08-23 |
| WO2008039699A1 (en) | 2008-04-03 |
| EP2066715A1 (en) | 2009-06-10 |
| AU2007300253A1 (en) | 2008-04-03 |
| US8076518B2 (en) | 2011-12-13 |
| EA016982B1 (ru) | 2012-08-30 |
| JP2010504411A (ja) | 2010-02-12 |
| EA200870346A1 (ru) | 2009-04-28 |
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