DD206151A5 - Neue polyisozyanatgemische - Google Patents

Neue polyisozyanatgemische Download PDF

Info

Publication number: DD206151A5
Authority: DD; German Democratic Republic
Prior art keywords: mixture; weight; alkyl; polyisocyanate; residue
Prior art date: 1980-08-28

Application number

DD81232754A

Other languages

German (de)

English (en)

Inventor

Hartmut Knoefel

Michael Brockelt

Original Assignee

Bayer Ag

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.)

1980-08-28

Filing date

1981-08-24

Publication date

1984-01-18

1981-08-24 Application filed by Bayer Ag filed Critical Bayer Ag

1984-01-18 Publication of DD206151A5 publication Critical patent/DD206151A5/de

Links

239000000203 mixture Substances 0.000 title abstract description 99
239000005056 polyisocyanate Substances 0.000 title abstract description 55
229920001228 polyisocyanate Polymers 0.000 title abstract description 55
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 3
-1 4-nitrobenzyl halide Chemical class 0.000 abstract description 23
239000000047 product Substances 0.000 abstract description 22
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 12
150000004996 alkyl benzenes Chemical class 0.000 abstract description 9
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract description 8
238000005984 hydrogenation reaction Methods 0.000 abstract description 7
238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 6
125000003277 amino group Chemical group 0.000 abstract description 6
125000004432 carbon atom Chemical group C* 0.000 abstract description 6
239000007795 chemical reaction product Substances 0.000 abstract description 6
235000019445 benzyl alcohol Nutrition 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract description 3
BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical class [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 abstract description 2
239000003377 acid catalyst Substances 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
150000005181 nitrobenzenes Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
238000000034 method Methods 0.000 description 47
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
238000003756 stirring Methods 0.000 description 22
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 19
238000009835 boiling Methods 0.000 description 18
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
238000001816 cooling Methods 0.000 description 18
238000004821 distillation Methods 0.000 description 17
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 15
238000006396 nitration reaction Methods 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 12
239000012948 isocyanate Substances 0.000 description 12
150000002513 isocyanates Chemical class 0.000 description 12
229910017604 nitric acid Inorganic materials 0.000 description 12
229920000768 polyamine Polymers 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
239000007858 starting material Substances 0.000 description 11
230000000802 nitrating effect Effects 0.000 description 10
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
229940073608 benzyl chloride Drugs 0.000 description 6
239000004814 polyurethane Substances 0.000 description 6
229920002635 polyurethane Polymers 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000012043 crude product Substances 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
150000002828 nitro derivatives Chemical class 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000004033 plastic Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 3
239000000470 constituent Substances 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
238000007700 distillative separation Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000005524 benzylchlorides Chemical class 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
GYAKCBLLZSLOPW-UHFFFAOYSA-N (1-nitro-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C([N+]([O-])=O)(C)C1=CC=CC=C1 GYAKCBLLZSLOPW-UHFFFAOYSA-N 0.000 description 1
FXLWSUHZHAZSGJ-UHFFFAOYSA-N (2,2-diisocyanato-1-phenylethyl)benzene Chemical class C=1C=CC=CC=1C(C(N=C=O)N=C=O)C1=CC=CC=C1 FXLWSUHZHAZSGJ-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical compound CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 description 1
KSYQGOYOIKQFNA-UHFFFAOYSA-N 1-benzyl-3-methylbenzene Chemical compound CC1=CC=CC(CC=2C=CC=CC=2)=C1 KSYQGOYOIKQFNA-UHFFFAOYSA-N 0.000 description 1
SIYISNUJKMAQBV-UHFFFAOYSA-N 1-benzyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1CC1=CC=CC=C1 SIYISNUJKMAQBV-UHFFFAOYSA-N 0.000 description 1
CGQSTTINOGWALD-UHFFFAOYSA-N 1-methyl-2-nitro-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 CGQSTTINOGWALD-UHFFFAOYSA-N 0.000 description 1
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
ARUXXUTXKQNTGM-UHFFFAOYSA-N 2,2-diphenylethane-1,1-diamine Chemical compound C=1C=CC=CC=1C(C(N)N)C1=CC=CC=C1 ARUXXUTXKQNTGM-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 description 1
FTIYSRPLLHVLSK-UHFFFAOYSA-N 3-(1-phenylethyl)benzene-1,2-diamine Chemical class C1(=CC=CC=C1)C(C)C1=C(C(=CC=C1)N)N FTIYSRPLLHVLSK-UHFFFAOYSA-N 0.000 description 1
ZXRJUBLHFHDUJH-UHFFFAOYSA-N 3-ethylbenzene-1,2-diamine Chemical compound CCC1=CC=CC(N)=C1N ZXRJUBLHFHDUJH-UHFFFAOYSA-N 0.000 description 1
GFYLESPRRMAABM-UHFFFAOYSA-N 4-(1-phenylethyl)benzene-1,2,3-triamine Chemical compound NC1=C(C(=C(C=C1)C(C1=CC=CC=C1)C)N)N GFYLESPRRMAABM-UHFFFAOYSA-N 0.000 description 1
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
101710091681 Methanogen homoaconitase small subunit Proteins 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
101710140240 Probable methanogen homoaconitase large subunit Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
NYTOUQBROMCLBJ-UHFFFAOYSA-N Tetranitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O NYTOUQBROMCLBJ-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
JYPKTXWNQVIJJE-UHFFFAOYSA-N [dinitro(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C([N+]([O-])=O)([N+](=O)[O-])C1=CC=CC=C1 JYPKTXWNQVIJJE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
SYWDWCWQXBUCOP-UHFFFAOYSA-N benzene;ethene Chemical compound C=C.C1=CC=CC=C1 SYWDWCWQXBUCOP-UHFFFAOYSA-N 0.000 description 1
JJPUEFAGHJREQD-UHFFFAOYSA-N benzhydryl cyanate Chemical class C=1C=CC=CC=1C(OC#N)C1=CC=CC=C1 JJPUEFAGHJREQD-UHFFFAOYSA-N 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical class NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
229920000582 polyisocyanurate Polymers 0.000 description 1
239000011495 polyisocyanurate Substances 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000004448 titration Methods 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyurethanes Or Polyureas (AREA)

DD81232754A 1980-08-28 1981-08-24 Neue polyisozyanatgemische DD206151A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803032358 DE3032358A1 (de)	1980-08-28	1980-08-28	Neue polyisocyanate bzw. polyisocyanatgemische der diphenylmethanreihe, verfahren zu ihrer herstellung, sowie ihre verwendung als aufbaukomponente bei der herstellung von polyurethankunststoffen nach dem isocyanat-polyadditionsverfahren

Publications (1)

Publication Number	Publication Date
DD206151A5 true DD206151A5 (de)	1984-01-18

Family

ID=6110541

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81232754A DD206151A5 (de)	1980-08-28	1981-08-24	Neue polyisozyanatgemische

Country Status (8)

Country	Link
US (1)	US4613687A (fr)
EP (1)	EP0046917B1 (fr)
JP (1)	JPS5775965A (fr)
AT (1)	ATE5533T1 (fr)
AU (1)	AU546902B2 (fr)
CA (1)	CA1171097A (fr)
DD (1)	DD206151A5 (fr)
DE (2)	DE3032358A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2525216B1 (fr) *	1982-04-16	1985-10-25	Ugine Kuhlmann	Isocyanates aromatiques halogenes, ou leurs melanges, a structure diphenylmethane et leur procede de fabrication
DE3234996A1 (de) *	1982-09-22	1984-03-22	Bayer Ag, 5090 Leverkusen	Gegebenenfalls isomerengemische darstellende cycloaliphatische diisocyanate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als ausgangsmaterialien bei der herstellung von polyurethankunststoffen
DE3235573A1 (de) *	1982-09-25	1984-03-29	Bayer Ag, 5090 Leverkusen	Gegebenenfalls isomerengemische darstellende cycloaliphatische diisocyanate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als ausgangsmaterialien bei der herstellung von polyurethankunststoffen
DE3417683A1 (de) *	1984-05-12	1985-11-14	Bayer Ag, 5090 Leverkusen	Neue cycloaliphatische triisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung bei der herstellung von polyurethankunststoffen
DE3417684A1 (de) *	1984-05-12	1985-11-14	Bayer Ag, 5090 Leverkusen	Neue triisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethankunststoffen
DE3721058A1 (de)	1987-06-26	1989-01-05	Bayer Ag	Verfahren zur herstellung von kalthaertenden polyurethan-weichformschaumstoffen
DE3829290A1 (de) *	1988-08-30	1990-03-15	Bayer Ag	Polyetherpolyole auf basis aromatischer di- und/oder polyamine, verfahren zu ihrer herstellung und verwendung fuer polyurethan- und polyisocyanurat-kunststoffe
US5977422A (en) *	1997-06-09	1999-11-02	The Dow Chemical Company	Organoaluminum catalysis of alkylation reactions
US6740192B1 (en)	1999-09-27	2004-05-25	Georgia Tech Research Corp.	Joining electroconductive materials with electroconductive adhesive containing epoxide-modified polyurethane
ATE478907T1 (de) *	2006-04-12	2010-09-15	Basf Se	Verfahren zur herstellung von polyurethanen
EP2028206A1 (fr) *	2007-08-23	2009-02-25	Huntsman International Llc	Compositions polyisocyanates polyaromatiques

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3255226A (en) *	1962-12-21	1966-06-07	Du Pont	Process for the preparation of arylmethane isocyanates and the purification of alkyl and haloalkyl isocyanates
DE1812565C3 (de) *	1968-12-04	1975-04-24	Bayer Ag	Verkleben von Werkstoffen mit polyisocyanathaltigen Klebstoffen auf Basis von Natur- oder Synthesekautschuk
US3903124A (en) *	1973-11-15	1975-09-02	Olin Corp	Methylene-bridged diaryl diisocyanates
US3941822A (en) *	1974-10-03	1976-03-02	Olin Corporation	Process for the preparation of methylene-bridged diaryl isocyanates
US3933701A (en) *	1975-01-29	1976-01-20	Olin Corporation	High resilience polyurethane foam
DE2935318A1 (de) *	1979-08-31	1981-03-26	Bayer Ag, 51373 Leverkusen	Neue diisocyanate bzw. diisocyanatgemische der diphenylmethanreihe, verfahren zu ihrer herstellung, sowie ihre verwendung als aufbaukomponente bei der herstellung von polyurethankunststoffen nach dem isocyanat-polyadditionsverfahren
DE3032128A1 (de) *	1980-08-26	1982-04-08	Bayer Ag, 5090 Leverkusen	Neue diisocyanate bzw. diisocyanatgemische der diphenylmethanreihe, verfahren zu ihrer herstellung, sowie ihre verwendung als aufbaukomponente bei der herstellung von polyurethankunststoffen nach dem isocyanat-polyadditionsverfahren

1980
- 1980-08-28 DE DE19803032358 patent/DE3032358A1/de not_active Withdrawn
1981
- 1981-07-31 CA CA000383031A patent/CA1171097A/fr not_active Expired
- 1981-08-17 AT AT81106367T patent/ATE5533T1/de not_active IP Right Cessation
- 1981-08-17 DE DE8181106367T patent/DE3161591D1/de not_active Expired
- 1981-08-17 US US06/293,748 patent/US4613687A/en not_active Expired - Fee Related
- 1981-08-17 EP EP81106367A patent/EP0046917B1/fr not_active Expired
- 1981-08-24 DD DD81232754A patent/DD206151A5/de unknown
- 1981-08-26 JP JP56132650A patent/JPS5775965A/ja active Granted
- 1981-08-26 AU AU74624/81A patent/AU546902B2/en not_active Ceased

Also Published As

Publication number	Publication date
US4613687A (en)	1986-09-23
EP0046917A1 (fr)	1982-03-10
ATE5533T1 (de)	1983-12-15
DE3032358A1 (de)	1982-04-08
CA1171097A (fr)	1984-07-17
AU546902B2 (en)	1985-09-26
DE3161591D1 (en)	1984-01-12
AU7462481A (en)	1982-03-04
EP0046917B1 (fr)	1983-12-07
JPS5775965A (en)	1982-05-12
JPH0319219B2 (fr)	1991-03-14

Publication	Publication Date	Title
EP0024665B1 (fr)	1982-05-05	Diisocyanates ou mélanges de diisocyanates de la série diphénylméthane, procédé pour leur préparation et leur utilisation comme produits de départ pour la préparation de polyuréthanes selon le procédé de polymérisation par addition d'isocyanates
DE1568017A1 (de)	1970-03-26	Verfahren zur Herstellung von stabilen Polyisocyanaten
EP0046917B1 (fr)	1983-12-07	Mélanges de polyisocyanates du type diphénylméthane, ainsi que leur application comme composants de synthèse lors de la fabrication de polyuréthanes en utilisant le procédé de polyaddition des isocyanates
EP0062823B1 (fr)	1985-01-30	Procédé de production de polyisocyanates aromatiques porteurs de groupes urée et/ou de groupes biuret et leur utilisation comme composant isocyanate dans la fabrication de polyuréthannes
EP0046556B1 (fr)	1983-03-09	Diisocyanates et mélanges de diisocyanates du type diphénylméthane, procédé pour leur préparation ainsi que leur application comme composants de synthèse lors de la fabrication de polyuréthanes en utilisant le procédé de polyaddition des isocyanates
EP0158059B1 (fr)	1986-12-30	Procédé de préparation de polyamines et leur utilisation pour la préparation de polyisocyanates
DE19958389A1 (de)	2001-06-07	Verfahren zur Herstellung eines Dinitronaphthalin-Isomerengemisches mit erhöhtem Anteil an 1,5-Dinitronaphthalin
EP0696571B1 (fr)	2000-01-26	Procédé pour la préparation de dinitrotoluène
EP0113044B1 (fr)	1986-09-03	Diisocyanates ou mélanges de diisocyanates, un procédé pour leur fabrication, ainsi que leur utilisation pour la fabrication de polyuréthanes
EP0162347B1 (fr)	1987-12-09	Triisocyanates cycloaliphatiques, procédé de leur production et leur utilisation dans la fabrication des polyuréthanes
EP0104531B1 (fr)	1985-11-21	Diisocyanates cycloaliphatiques, éventuellement sous forme de mélanges d'isomères, leur méthode de préparation et leur utilisation comme produits de départ dans la préparation de produits synthétiques du type polyuréthanes
EP0104551B1 (fr)	1985-11-13	Diisocyanates cycloaliphatiques, éventuellement sous forme de mélanges d'isomères, leur méthode de préparation et leur utilisation comme produits de départ dans la préparation de produits synthétiques du type polyuréthanes
EP0162346B1 (fr)	1987-06-03	Triisocyanates, procédé de leur production et leur utilisation dans la fabrication des polyuréthanes
DE1793137A1 (de)	1972-03-09	Verfahren zur Herstellung von Di(aminophenyl)methan
DE3641702A1 (de)	1988-06-16	Diisocyanate und diisocyanatgemische, ein verfahren zu ihrer herstellung und ihrer verwendung bei der herstellung von polyurethankunststoffen
DE3231912A1 (de)	1984-03-01	Diamine oder diamingemische, sowie ein verfahren zu ihrer herstellung
EP0113043B1 (fr)	1985-09-11	Diisocyanates ou un mélange de diisocyanates, leur méthode de préparation et leur application pour la préparation de matières synthétiques du type polyuréthane
DE3105362A1 (de)	1982-09-02	Neue diamine, ein verfahren zu ihrer herstellung, sowie ihre verwendung als kettenverlaengerungsmittel bei der herstellung von polyurethankunststoffen
DE2307864A1 (de)	1974-08-22	Verfahren zur herstellung von diaminodiarylmethanen
EP0206060B1 (fr)	1988-05-18	Diisocyanates, leur procédé de préparation et leur utilisation comme composants de synthèse dans la préparation de Polyuréthanes ou d'intermédiaires de polyuréthanes
DE2207492A1 (de)	1972-11-23	Verfahren zur Reinigung von Aminen
DE2709490A1 (de)	1978-09-07	Verfahren zur herstellung von polyarylaminen
DE2031289A1 (de)	1971-01-14	Verfahren zur Herstellung von alpha-Isocyanatoalkylarenen mit ein oder mehre ren Isocyanatoalkylgruppen
EP0283884A1 (fr)	1988-09-28	Diisocyanates et leur procédé pour la préparation des diisocyanates