DD236539A5 - Verwendung und herstellung von substituierten p,p'-methylen-bis-anilinen - Google Patents
Verwendung und herstellung von substituierten p,p'-methylen-bis-anilinen Download PDFInfo
- Publication number
- DD236539A5 DD236539A5 DD85277942A DD27794285A DD236539A5 DD 236539 A5 DD236539 A5 DD 236539A5 DD 85277942 A DD85277942 A DD 85277942A DD 27794285 A DD27794285 A DD 27794285A DD 236539 A5 DD236539 A5 DD 236539A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- bis
- aniline
- methylene
- mol
- diethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003822 epoxy resin Substances 0.000 claims abstract description 9
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 9
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- 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 claims abstract description 8
- 239000004814 polyurethane Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 30
- 239000004970 Chain extender Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229920005749 polyurethane resin Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 230000003505 mutagenic effect Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 231100000243 mutagenic effect Toxicity 0.000 description 11
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 10
- 206010028400 Mutagenic effect Diseases 0.000 description 10
- YJWWPPMNMFNBHX-UHFFFAOYSA-N 2-chloro-6-ethylaniline Chemical compound CCC1=CC=CC(Cl)=C1N YJWWPPMNMFNBHX-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 241001112258 Moca Species 0.000 description 8
- 239000004848 polyfunctional curative Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 6
- 238000010953 Ames test Methods 0.000 description 6
- 231100000039 Ames test Toxicity 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- -1 Dichloro-ethylene-bis-aniline Chemical compound 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- NHYYMKIPFJBWQY-UHFFFAOYSA-N n'-(2-chloro-6-ethylphenyl)-n-(2,6-diethylphenyl)methanediamine Chemical compound CCC1=CC=CC(Cl)=C1NCNC1=C(CC)C=CC=C1CC NHYYMKIPFJBWQY-UHFFFAOYSA-N 0.000 description 4
- GRZJGKXZOJLTTA-UHFFFAOYSA-N n,n'-bis(2-chloro-6-ethylphenyl)methanediamine Chemical compound CCC1=CC=CC(Cl)=C1NCNC1=C(Cl)C=CC=C1CC GRZJGKXZOJLTTA-UHFFFAOYSA-N 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 3
- ZOOFYKBJOLCAJU-UHFFFAOYSA-N N-(2-butan-2-yl-6-ethylphenyl)-N'-(2-chloro-6-ethylphenyl)methanediamine Chemical compound CCC(C)C1=CC=CC(CC)=C1NCNC1=C(Cl)C=CC=C1CC ZOOFYKBJOLCAJU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- CXIYYOYZPKTYPY-UHFFFAOYSA-N n'-(2-butan-2-yl-6-ethylphenyl)-n-(2,6-diethylphenyl)methanediamine Chemical compound CCC(C)C1=CC=CC(CC)=C1NCNC1=C(CC)C=CC=C1CC CXIYYOYZPKTYPY-UHFFFAOYSA-N 0.000 description 3
- SFVJGQYZZVZUDN-UHFFFAOYSA-N n,n'-bis(2,6-diethylphenyl)methanediamine Chemical compound CCC1=CC=CC(CC)=C1NCNC1=C(CC)C=CC=C1CC SFVJGQYZZVZUDN-UHFFFAOYSA-N 0.000 description 3
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 3
- 229920003225 polyurethane elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 2
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- XJRWMFDPXGJBIC-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]methanediamine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NCNC1=C(C(C)C)C=CC=C1C(C)C XJRWMFDPXGJBIC-UHFFFAOYSA-N 0.000 description 2
- YXYPMKULICLSPP-UHFFFAOYSA-N n-(2,6-diethylphenyl)-n'-[2,6-di(propan-2-yl)phenyl]methanediamine Chemical compound CCC1=CC=CC(CC)=C1NCNC1=C(C(C)C)C=CC=C1C(C)C YXYPMKULICLSPP-UHFFFAOYSA-N 0.000 description 2
- VZUVKYJVVRTZDY-UHFFFAOYSA-N n-(2-chloro-6-ethylphenyl)-n'-[2,6-di(propan-2-yl)phenyl]methanediamine Chemical compound CCC1=CC=CC(Cl)=C1NCNC1=C(C(C)C)C=CC=C1C(C)C VZUVKYJVVRTZDY-UHFFFAOYSA-N 0.000 description 2
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1N=C=O ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical class CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-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
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 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
- 239000007791 liquid phase Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/3243—Polyamines aromatic containing two or more aromatic rings
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3814—Polyamines
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Indole Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Developing Agents For Electrophotography (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3281/84A CH660358A5 (de) | 1984-07-06 | 1984-07-06 | Substituierte p,p'-methylen-bisaniline. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD236539A5 true DD236539A5 (de) | 1986-06-11 |
Family
ID=4252582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85277942A DD236539A5 (de) | 1984-07-06 | 1985-06-28 | Verwendung und herstellung von substituierten p,p'-methylen-bis-anilinen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4978791A (fr) |
| EP (1) | EP0171588B1 (fr) |
| JP (1) | JPH0617438B2 (fr) |
| AT (1) | ATE56943T1 (fr) |
| CA (1) | CA1226302A (fr) |
| CH (1) | CH660358A5 (fr) |
| CS (1) | CS251789B2 (fr) |
| DD (1) | DD236539A5 (fr) |
| DE (1) | DE3579872D1 (fr) |
| DK (1) | DK167065B1 (fr) |
| FI (1) | FI85464C (fr) |
| HU (1) | HU198007B (fr) |
| IL (1) | IL75555A (fr) |
| NO (1) | NO852718L (fr) |
| SU (1) | SU1375122A3 (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH660358A5 (de) * | 1984-07-06 | 1987-04-15 | Lonza Ag | Substituierte p,p'-methylen-bisaniline. |
| 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. |
| DD292005A5 (de) * | 1989-03-17 | 1991-07-18 | ������@������������k�� | Kettenverlaengerungsmittel fuer p-phenylen-methylendiisocyanat-(mdi)-prepolymere fuer gegossene polyurethan-elastomere (pu-elastomere) |
| US5015718A (en) * | 1989-06-30 | 1991-05-14 | Martin Marietta Energy Systems, Inc. | Adhesives and method for making the same |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| JP2591354B2 (ja) * | 1991-01-18 | 1997-03-19 | 東洋製罐株式会社 | 缶詰製造ラインにおける缶への非液体内容物充填装置 |
| FR2773809B1 (fr) | 1998-01-22 | 2000-03-17 | Inst Francais Du Petrole | Compositions de polymeres, leurs preparations et leurs utilisations |
| US6350514B1 (en) | 2000-02-02 | 2002-02-26 | General Electric Co. | Thermoplastic blends with improved adhesion and thermal stability |
| US7501461B2 (en) * | 2004-04-12 | 2009-03-10 | University Of North Texas | Composition of epoxy resin, aliphatic amine curing agent and halogenated amine |
| RU2272046C1 (ru) * | 2004-08-12 | 2006-03-20 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт полимерных материалов" | Способ получения отвердителя |
| ES2319367B1 (es) * | 2007-07-03 | 2010-01-12 | Kao Corporation, S.A. | Composiciones antiapelmazantes para fertilizantes. |
| GB2478343A (en) * | 2010-03-05 | 2011-09-07 | Hexcel Composites Ltd | Asymmetric bis-aniline resin curing agent |
| GB201004940D0 (en) | 2010-03-24 | 2010-05-12 | Hexcel Composites Ltd | Novel curing agents |
| EP2638088B1 (fr) | 2010-09-02 | 2015-11-18 | Lonza Ltd | Halogénation des 4,4'-méthylène-bis-anilines |
| US9321881B2 (en) * | 2011-08-12 | 2016-04-26 | Air Products And Chemicals, Inc. | Liquid methylenedianiline compositions |
| RU2682250C2 (ru) * | 2014-02-06 | 2019-03-18 | Хексел Композитс Лимитед | Отверждающие агенты для эпоксидных смол |
| CN105693526A (zh) * | 2016-04-01 | 2016-06-22 | 衢州信步化工科技有限公司 | 一种4,4′-亚甲基-双-(3-氯-2,6-二乙基苯胺)的制备方法 |
| WO2019077523A1 (fr) * | 2017-10-17 | 2019-04-25 | Aditya Birla Chemicals (Thailand) Limited | Résines époxy du type glycidylamine basées sur des amines négatives ames |
| US20210403637A1 (en) * | 2018-11-13 | 2021-12-30 | Cytec Industries Inc. | Curable resin composition and fiber reinforced resin matrix composite material |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA714092A (en) * | 1965-07-20 | Monsanto Company | Preparation of bis(substituted phenyl)methanes | |
| BE611425A (fr) * | 1960-12-15 | |||
| US3203932A (en) * | 1961-03-10 | 1965-08-31 | Wyandotte Chemicals Corp | Metallo-organic catalyzed one-shot process for preparing urethaneurea elastomers |
| US3322810A (en) * | 1963-09-19 | 1967-05-30 | Monsanto Co | Hindered isothiocyanates, and the method of preparing the same |
| DE1240654B (de) * | 1965-05-14 | 1967-05-18 | Bayer Ag | Verfahren zur Herstellung vernetzter Kunststoffe nach dem Isocyanat-Polyadditions-Verfahren |
| US3427282A (en) * | 1967-03-28 | 1969-02-11 | Uniroyal Inc | Use of selected 4,4'-methylene-bis(2-alkylanilines) as curing agent for epoxy resins |
| US3857890A (en) * | 1969-07-25 | 1974-12-31 | Upjohn Co | Process for preparing methylene-di-anilines |
| FR2054814A5 (en) * | 1969-07-28 | 1971-05-07 | Rhodiaceta | Diamino diphenyl methane derivs prodn |
| DE2239237A1 (de) * | 1972-08-09 | 1974-02-21 | Heinz Bildner | Verfahren zum herstellen von kuverts mit kaschierungsstreifen |
| US3804806A (en) * | 1972-08-09 | 1974-04-16 | Sherwin Williams Co | Alkoxy anilines as curing agents for epoxy resins |
| DE2339237A1 (de) * | 1973-08-02 | 1975-02-20 | Nippon Kayaku Kk | 4,4'-diaminodiphenylmethane, verfahren zu ihrer herstellung und ihre verwendung als haerter fuer epoxyharze |
| 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 |
| DE3126436A1 (de) * | 1981-07-04 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls zellhaltigen polyurethan- oder polyurethan-polyharnstoff-formkoerpern |
| FR2522653A1 (fr) * | 1982-03-05 | 1983-09-09 | Ugine Kuhlmann | Diamines aromatiques halogenees, leur procede de fabrication, et leur application a la fabrication des polyurethannes |
| CH660358A5 (de) * | 1984-07-06 | 1987-04-15 | Lonza Ag | Substituierte p,p'-methylen-bisaniline. |
| 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. |
-
1984
- 1984-07-06 CH CH3281/84A patent/CH660358A5/de not_active IP Right Cessation
-
1985
- 1985-06-13 FI FI852356A patent/FI85464C/fi not_active IP Right Cessation
- 1985-06-14 DK DK270485A patent/DK167065B1/da not_active IP Right Cessation
- 1985-06-18 IL IL75555A patent/IL75555A/xx not_active IP Right Cessation
- 1985-06-25 US US06/748,594 patent/US4978791A/en not_active Expired - Fee Related
- 1985-06-27 CA CA000485743A patent/CA1226302A/fr not_active Expired
- 1985-06-28 DD DD85277942A patent/DD236539A5/de not_active IP Right Cessation
- 1985-07-03 CS CS855003A patent/CS251789B2/cs unknown
- 1985-07-04 SU SU853915009A patent/SU1375122A3/ru active
- 1985-07-04 JP JP60147596A patent/JPH0617438B2/ja not_active Expired - Lifetime
- 1985-07-05 NO NO852718A patent/NO852718L/no unknown
- 1985-07-05 DE DE8585108373T patent/DE3579872D1/de not_active Expired - Fee Related
- 1985-07-05 AT AT85108373T patent/ATE56943T1/de not_active IP Right Cessation
- 1985-07-05 HU HU852623A patent/HU198007B/hu not_active IP Right Cessation
- 1985-07-05 EP EP85108373A patent/EP0171588B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SU1375122A3 (ru) | 1988-02-15 |
| FI852356A0 (fi) | 1985-06-13 |
| FI85464C (fi) | 1992-04-27 |
| CS251789B2 (en) | 1987-08-13 |
| EP0171588A1 (fr) | 1986-02-19 |
| DK270485D0 (da) | 1985-06-14 |
| CH660358A5 (de) | 1987-04-15 |
| DE3579872D1 (de) | 1990-10-31 |
| FI85464B (fi) | 1992-01-15 |
| IL75555A0 (en) | 1985-10-31 |
| IL75555A (en) | 1989-06-30 |
| CA1226302A (fr) | 1987-09-01 |
| DK167065B1 (da) | 1993-08-23 |
| JPS6131419A (ja) | 1986-02-13 |
| ATE56943T1 (de) | 1990-10-15 |
| NO852718L (no) | 1986-01-07 |
| FI852356L (fi) | 1986-01-07 |
| HUT38606A (en) | 1986-06-30 |
| JPH0617438B2 (ja) | 1994-03-09 |
| DK270485A (da) | 1986-01-07 |
| CS500385A2 (en) | 1986-12-18 |
| EP0171588B1 (fr) | 1990-09-26 |
| HU198007B (en) | 1989-07-28 |
| US4978791A (en) | 1990-12-18 |
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| ENJ | Ceased due to non-payment of renewal fee |