CA1248552A - 1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane - Google Patents

1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane

Info

Publication number: CA1248552A
Authority: CA; Canada
Prior art keywords: isocyanatomethyl; isocyanato; aminomethyl; methyl; alkyl
Prior art date: 1983-05-17
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.): Expired

Application number

CA000529628A

Other languages

English (en)

Inventor

Erwin Hahn

Peter Neumann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1983-05-17

Filing date

1987-02-12

Publication date

1989-01-10

1983-05-17 Priority claimed from DE3317875A external-priority patent/DE3317875A1/de

1987-02-12 Application filed by BASF SE filed Critical BASF SE

1987-02-12 Priority to CA000529628A priority Critical patent/CA1248552A/fr

1989-01-10 Application granted granted Critical

1989-01-10 Publication of CA1248552A publication Critical patent/CA1248552A/fr

Status Expired legal-status Critical Current

Links

150000004985 diamines Chemical class 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 33
NIDAJEKVJBGCCT-UHFFFAOYSA-N 5-(aminomethyl)-2-methylcyclohexan-1-amine Chemical compound CC1CCC(CN)CC1N NIDAJEKVJBGCCT-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
XXUDRZNTPMRRJH-UHFFFAOYSA-N 3-(aminomethyl)-2-methylcyclohexan-1-amine Chemical compound CC1C(N)CCCC1CN XXUDRZNTPMRRJH-UHFFFAOYSA-N 0.000 claims 1
JFKNFQZRGODHKY-UHFFFAOYSA-N 3-(aminomethyl)-4-methylcyclohexan-1-amine Chemical compound CC1CCC(N)CC1CN JFKNFQZRGODHKY-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 16
125000005442 diisocyanate group Chemical group 0.000 abstract description 15
238000003776 cleavage reaction Methods 0.000 abstract description 4
230000007017 scission Effects 0.000 abstract description 4
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract description 3
239000004033 plastic Substances 0.000 abstract description 3
229920003023 plastic Polymers 0.000 abstract description 3
239000004814 polyurethane Substances 0.000 abstract description 2
229920002635 polyurethane Polymers 0.000 abstract description 2
239000011814 protection agent Substances 0.000 abstract description 2
-1 aliphatic diamines Chemical class 0.000 description 15
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
238000000034 method Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
238000004949 mass spectrometry Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000006396 nitration reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229920001228 polyisocyanate Polymers 0.000 description 3
239000005056 polyisocyanate Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 2
NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 2
KOFBNBCOGKLUOM-UHFFFAOYSA-N 4-methyl-3-nitrobenzonitrile Chemical compound CC1=CC=C(C#N)C=C1[N+]([O-])=O KOFBNBCOGKLUOM-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
XWURZHGKODQZMK-UHFFFAOYSA-N O.[Ru]=O Chemical compound O.[Ru]=O XWURZHGKODQZMK-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ZPIUNWNJPUKYQQ-UHFFFAOYSA-N 1,4-diisocyanato-1-methylcyclohexane Chemical class O=C=NC1(C)CCC(N=C=O)CC1 ZPIUNWNJPUKYQQ-UHFFFAOYSA-N 0.000 description 1
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
BMIJPNFRJPTSQO-UHFFFAOYSA-N 1-decyl-2-isocyanato-4-(isocyanatomethyl)cyclohexane Chemical compound CCCCCCCCCCC1CCC(CN=C=O)CC1N=C=O BMIJPNFRJPTSQO-UHFFFAOYSA-N 0.000 description 1
YHGNUFDTIGJFTK-UHFFFAOYSA-N 1-dodecyl-2-isocyanato-4-(isocyanatomethyl)cyclohexane Chemical compound CCCCCCCCCCCCC1CCC(CN=C=O)CC1N=C=O YHGNUFDTIGJFTK-UHFFFAOYSA-N 0.000 description 1
ULQCGAYIOMNISK-UHFFFAOYSA-N 1-ethyl-2-isocyanato-4-(isocyanatomethyl)cyclohexane Chemical compound CCC1CCC(CN=C=O)CC1N=C=O ULQCGAYIOMNISK-UHFFFAOYSA-N 0.000 description 1
HFDJNGGIBFYLFS-UHFFFAOYSA-N 1-heptyl-2-isocyanato-4-(isocyanatomethyl)cyclohexane Chemical compound CCCCCCCC1CCC(CN=C=O)CC1N=C=O HFDJNGGIBFYLFS-UHFFFAOYSA-N 0.000 description 1
OVXXGXGXZXQOIY-UHFFFAOYSA-N 1-hexyl-2-isocyanato-4-(isocyanatomethyl)cyclohexane Chemical compound CCCCCCC1CCC(CN=C=O)CC1N=C=O OVXXGXGXZXQOIY-UHFFFAOYSA-N 0.000 description 1
ZTGKSPOFKTUXCY-UHFFFAOYSA-N 2-(nitromethyl)benzonitrile Chemical compound [O-][N+](=O)CC1=CC=CC=C1C#N ZTGKSPOFKTUXCY-UHFFFAOYSA-N 0.000 description 1
WNTBPQPTPPOSPW-UHFFFAOYSA-N 2-isocyanato-1-(isocyanatomethyl)-4-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(CN=C=O)C(N=C=O)C1 WNTBPQPTPPOSPW-UHFFFAOYSA-N 0.000 description 1
BPQILIOHBVHJFC-UHFFFAOYSA-N 2-isocyanato-1-(isocyanatomethyl)-4-propylcyclohexane Chemical compound CCCC1CCC(CN=C=O)C(N=C=O)C1 BPQILIOHBVHJFC-UHFFFAOYSA-N 0.000 description 1
IXONRNUDOGMJAN-UHFFFAOYSA-N 2-isocyanato-4-(isocyanatomethyl)-1-methylcyclohexane Chemical compound CC1CCC(CN=C=O)CC1N=C=O IXONRNUDOGMJAN-UHFFFAOYSA-N 0.000 description 1
YJOKTVPBGXTPSX-UHFFFAOYSA-N 2-isocyanato-4-(isocyanatomethyl)-1-pentylcyclohexane Chemical compound CCCCCC1CCC(CN=C=O)CC1N=C=O YJOKTVPBGXTPSX-UHFFFAOYSA-N 0.000 description 1
ZYPMEESAXRBJIB-UHFFFAOYSA-N 2-isocyanato-4-(isocyanatomethyl)-1-propylcyclohexane Chemical compound CCCC1CCC(CN=C=O)CC1N=C=O ZYPMEESAXRBJIB-UHFFFAOYSA-N 0.000 description 1
BIQSLBBDPQJGFN-UHFFFAOYSA-N 2-isocyanato-4-(isocyanatomethyl)-1-undecylcyclohexane Chemical compound CCCCCCCCCCCC1CCC(CN=C=O)CC1N=C=O BIQSLBBDPQJGFN-UHFFFAOYSA-N 0.000 description 1
FTFQRHBFTRLIND-UHFFFAOYSA-N 2-methyl-3-nitrobenzonitrile Chemical compound CC1=C(C#N)C=CC=C1[N+]([O-])=O FTFQRHBFTRLIND-UHFFFAOYSA-N 0.000 description 1
XOSDYLFXPMFRGF-UHFFFAOYSA-N 2-methyl-5-nitrobenzonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C#N XOSDYLFXPMFRGF-UHFFFAOYSA-N 0.000 description 1
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 1
RRCZRUXYTNNVBQ-UHFFFAOYSA-N 4-(aminomethyl)cyclohexan-1-amine Chemical class NCC1CCC(N)CC1 RRCZRUXYTNNVBQ-UHFFFAOYSA-N 0.000 description 1
VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
NZFHCGGMOCDYNN-UHFFFAOYSA-N 5-(aminomethyl)-2-ethylcyclohexan-1-amine Chemical compound CCC1CCC(CN)CC1N NZFHCGGMOCDYNN-UHFFFAOYSA-N 0.000 description 1
WNCSDYWOHLQEHM-UHFFFAOYSA-N 5-(aminomethyl)-2-methylaniline Chemical compound CC1=CC=C(CN)C=C1N WNCSDYWOHLQEHM-UHFFFAOYSA-N 0.000 description 1
CBWZLOYQDDMXHO-UHFFFAOYSA-N 5-(aminomethyl)-2-propylcyclohexan-1-amine Chemical compound CCCC1CCC(CN)CC1N CBWZLOYQDDMXHO-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 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
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000003136 n-heptyl 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])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003973 paint Substances 0.000 description 1
101150078860 pho gene Proteins 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000529628A 1983-05-17 1987-02-12 1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane Expired CA1248552A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000529628A CA1248552A (fr)	1983-05-17	1987-02-12	1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP3317875.5		1983-05-17
DE3317875A DE3317875A1 (de)	1983-05-17	1983-05-17	1-alkyl-2-isocyanatomethyl-isocyanato-cyclohexane und/oder 1-alkyl-4-isocyanatomethyl-isocyanato-cyclohexane sowie die entsprechenden diamine, verfahren zu deren herstellung und verwendung
CA000454484A CA1239415A (fr)	1983-05-17	1984-05-16	Amino-aminomethylcyclohexanes utiles pour la preparation des diisocyanates correspondants
CA000529628A CA1248552A (fr)	1983-05-17	1987-02-12	1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000454484A Division CA1239415A (fr)	1983-05-17	1984-05-16	Amino-aminomethylcyclohexanes utiles pour la preparation des diisocyanates correspondants

Publications (1)

Publication Number	Publication Date
CA1248552A true CA1248552A (fr)	1989-01-10

Family

ID=25670390

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000529628A Expired CA1248552A (fr)	1983-05-17	1987-02-12	1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane

Country Status (1)

Country	Link
CA (1)	CA1248552A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5786438A (en) *	1996-04-11	1998-07-28	Bayer Aktiengesellschaft	Mixtures of cycloaliphatic diisocyanates, a process for their preparation and their use for the production of polyisocyanate addition products
US5837796A (en) *	1996-07-10	1998-11-17	Bayer Aktiengesellschaft	Polyisocyanates containing isocyanurate groups and prepared by trimerizing alkyl-substituted cycloaliphatic diisocyanates

1987
- 1987-02-12 CA CA000529628A patent/CA1248552A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5786438A (en) *	1996-04-11	1998-07-28	Bayer Aktiengesellschaft	Mixtures of cycloaliphatic diisocyanates, a process for their preparation and their use for the production of polyisocyanate addition products
US5837796A (en) *	1996-07-10	1998-11-17	Bayer Aktiengesellschaft	Polyisocyanates containing isocyanurate groups and prepared by trimerizing alkyl-substituted cycloaliphatic diisocyanates

Legal Events

Date	Code	Title	Description
2006-01-10	MKEX	Expiry

Publication	Publication Date	Title
JPH0115498B2 (fr)	1989-03-17
US4761498A (en)	1988-08-02	Diisocyanates and diisocyanate mixtures based on diphenylmethane, processes for their production and their use as isocyanate component in the production of polyurethane plastics by the isocyanate polyaddition process
US4835239A (en)	1989-05-30	Diisocyanates and their use for the preparation of polyurethanes
CA1171097A (fr)	1984-07-17	Polyisocyanates de la serie diphenylmethane et methode d'obtention
CA1248552A (fr)	1989-01-10	1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane
US4597909A (en)	1986-07-01	Process for the production of polyisocyanates
CA1216857A (fr)	1987-01-20	Di-isocyanates, leurs melanges et leur production
US2963504A (en)	1960-12-06	Alkyl toluene diisocyanates
CA1239415A (fr)	1988-07-19	Amino-aminomethylcyclohexanes utiles pour la preparation des diisocyanates correspondants
US4675437A (en)	1987-06-23	Cycloaliphatic triisocyanates
CA1217198A (fr)	1987-01-27	Diisocyanates cycloaliphatiques pouvant exister sous forme d'isomeres; preparation
US4587058A (en)	1986-05-06	Diisocyanates of the diphenyl methane series and processes for the production thereof
US4914238A (en)	1990-04-03	Process for the production of diisocyanates, selected diisocyantes produced thereby and the production of polyurethane plastics therefrom
US2729666A (en)	1956-01-03	Alkyl-aryl diisocyanates with reduced activity
US4603189A (en)	1986-07-29	Triisocyanates and a process for their preparation
US3162664A (en)	1964-12-22	Carbonate dhsocyanates
US3379758A (en)	1968-04-23	Phosgenation of n-arylsulfonyl, n'-alkyl-ureas to produce arylsulfonyl isocyanates
US4879409A (en)	1989-11-07	Cycloaliphatic diisocyanates, optionally in the form of isomeric mixtures and a process for their preparation
US4942164A (en)	1990-07-17	Polyfluorinated diisocyanates and fluorinated polyurethanes prepared therefrom
US4107199A (en)	1978-08-15	Bis(isocyanatopropyl) arylacetonitriles
CA1115285A (fr)	1981-12-29	Methode de preparation des urethanes
JPH07107042B2 (ja)	1995-11-15	高度に選択的なＳｎＯ２又はＣｕＯ触媒を用いるイソホロンジカルバミルエステルからのイソホロンジイソシアナ−トの製造方法
KR20250047805A (ko)	2025-04-04	이소포론 디이소시아네이트 조성물 및 이의 블록킹된 제품
US4512929A (en)	1985-04-23	1-Alkyl-2-isocyanatomethyl-isocyanatobenzenes and/or 1-alkyl-4-isocyanatomethyl-isocyanatobenzenes
US3461151A (en)	1969-08-12	Urethane containing isocyanates

CA1248552A - 1-alcoyl-2-aminomethyl-aminocyclohexane et (ou) 1-alcoyl-4-aminomethyl-aminocyclohexane - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (4)

Related Parent Applications (1)

Publications (1)

Family

ID=25670390

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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