DE2219336A1 - Härtbare Polyepoxidmasse - Google Patents
Härtbare PolyepoxidmasseInfo
- Publication number
- DE2219336A1 DE2219336A1 DE19722219336 DE2219336A DE2219336A1 DE 2219336 A1 DE2219336 A1 DE 2219336A1 DE 19722219336 DE19722219336 DE 19722219336 DE 2219336 A DE2219336 A DE 2219336A DE 2219336 A1 DE2219336 A1 DE 2219336A1
- Authority
- DE
- Germany
- Prior art keywords
- oxazoline
- radical
- carbon atoms
- oxazine
- composition according
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 13
- -1 2-oxazoline compound Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 16
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims description 14
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 14
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000012456 homogeneous solution Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000000376 2-oxazolines Chemical class 0.000 claims description 2
- IQOZTIKBIHWYQQ-UHFFFAOYSA-N 4h-1,3-oxazine Chemical compound C1C=COC=N1 IQOZTIKBIHWYQQ-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical class C1COC=NC1 YWOIQIYQBRDOQA-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- BEQDKWKSUMQVMX-UHFFFAOYSA-N 2,4-dimethyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C)=N1 BEQDKWKSUMQVMX-UHFFFAOYSA-N 0.000 description 1
- DXPIUHXKXUKZDK-UHFFFAOYSA-N 2,5-dimethyl-4,5-dihydro-1,3-oxazole Chemical compound CC1CN=C(C)O1 DXPIUHXKXUKZDK-UHFFFAOYSA-N 0.000 description 1
- UJFPWTWHKKVRHN-UHFFFAOYSA-N 2-(1-dodecylsulfanylpropan-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound CC(CSCCCCCCCCCCCC)C=1OCCN1 UJFPWTWHKKVRHN-UHFFFAOYSA-N 0.000 description 1
- LIDKWXWXDCAJCX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NCCO1 LIDKWXWXDCAJCX-UHFFFAOYSA-N 0.000 description 1
- SJJQTHCDSIMQGE-UHFFFAOYSA-N 2-(3-bromophenyl)-4,5-dihydro-1,3-oxazole Chemical compound BrC1=CC=CC(C=2OCCN=2)=C1 SJJQTHCDSIMQGE-UHFFFAOYSA-N 0.000 description 1
- OHJDDVYUQCSBSG-UHFFFAOYSA-N 2-(4-bromophenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(Br)=CC=C1C1=NCCO1 OHJDDVYUQCSBSG-UHFFFAOYSA-N 0.000 description 1
- RJDGOJYDQPRINZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1C1=NCCO1 RJDGOJYDQPRINZ-UHFFFAOYSA-N 0.000 description 1
- YSYWCNBSAQZIRO-UHFFFAOYSA-N 2-(4-fluorophenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(F)=CC=C1C1=NCCO1 YSYWCNBSAQZIRO-UHFFFAOYSA-N 0.000 description 1
- WSDXRZFWXBZSGW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=NCCO1 WSDXRZFWXBZSGW-UHFFFAOYSA-N 0.000 description 1
- MKLMHXJJPZJQKH-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-phenyl-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=NCC(C=2C=CC=CC=2)O1 MKLMHXJJPZJQKH-UHFFFAOYSA-N 0.000 description 1
- NYTUDOKVKPJSOI-UHFFFAOYSA-N 2-(4-methylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(C)=CC=C1C1=NCCO1 NYTUDOKVKPJSOI-UHFFFAOYSA-N 0.000 description 1
- MPQNFLWWBYWJGE-UHFFFAOYSA-N 2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NCCO1 MPQNFLWWBYWJGE-UHFFFAOYSA-N 0.000 description 1
- FRSCTGCNUCVOAC-UHFFFAOYSA-N 2-(dichloromethyl)-4,5-dihydro-1,3-oxazole Chemical compound ClC(Cl)C1=NCCO1 FRSCTGCNUCVOAC-UHFFFAOYSA-N 0.000 description 1
- YQXKCIOMIMUZGT-UHFFFAOYSA-N 2-(furan-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CO1 YQXKCIOMIMUZGT-UHFFFAOYSA-N 0.000 description 1
- NOJLQJLMXLMIRP-UHFFFAOYSA-N 2-(trichloromethyl)-4,5-dihydro-1,3-oxazole Chemical compound ClC(Cl)(Cl)C1=NCCO1 NOJLQJLMXLMIRP-UHFFFAOYSA-N 0.000 description 1
- SZTLLTPPOMQBLT-UHFFFAOYSA-N 2-[2-[2-(4,5-dihydro-1,3-oxazol-2-yl)ethylsulfanyl]ethyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCSCCC1=NCCO1 SZTLLTPPOMQBLT-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- OBIHXJLKWHVCEA-UHFFFAOYSA-N 2-cyclopropyl-4,5-dihydro-1,3-oxazole Chemical compound C1CC1C1=NCCO1 OBIHXJLKWHVCEA-UHFFFAOYSA-N 0.000 description 1
- MTYHIWQZNFDCJT-UHFFFAOYSA-N 2-ethoxy-4,5-dihydro-1,3-oxazole Chemical compound CCOC1=NCCO1 MTYHIWQZNFDCJT-UHFFFAOYSA-N 0.000 description 1
- MSOOXKBBMBRJCW-UHFFFAOYSA-N 2-ethylsulfanyl-4,5-dihydro-1,3-oxazole Chemical compound CCSC1=NCCO1 MSOOXKBBMBRJCW-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- KGBDUSZYCRLGHV-UHFFFAOYSA-N 4,4-dimethyl-2-(3,4,5-trimethoxyphenyl)-5h-1,3-oxazole Chemical compound COC1=C(OC)C(OC)=CC(C=2OCC(C)(C)N=2)=C1 KGBDUSZYCRLGHV-UHFFFAOYSA-N 0.000 description 1
- HELSSAYJULNHHM-UHFFFAOYSA-N 5,5-dimethyl-2-(3,4,5-trimethoxyphenyl)-4H-1,3-oxazole Chemical compound CC1(CN=C(O1)C1=CC(=C(C(=C1)OC)OC)OC)C HELSSAYJULNHHM-UHFFFAOYSA-N 0.000 description 1
- UWHWRJUMACAJPY-UHFFFAOYSA-N 5-methyl-2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1C(C)CN=C1C1=CC=CC=C1 UWHWRJUMACAJPY-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
- C08G59/68—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 catalysts used
- C08G59/72—Complexes of boron halides
-
- 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
- C08G59/5046—Amines heterocyclic
-
- 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
- C08G59/5093—Complexes of amines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13761971A | 1971-04-26 | 1971-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2219336A1 true DE2219336A1 (de) | 1972-11-30 |
Family
ID=22478282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722219336 Pending DE2219336A1 (de) | 1971-04-26 | 1972-04-20 | Härtbare Polyepoxidmasse |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU453009B2 (enExample) |
| BE (1) | BE782685A (enExample) |
| BR (1) | BR7202503D0 (enExample) |
| CA (1) | CA951046A (enExample) |
| DE (1) | DE2219336A1 (enExample) |
| FR (1) | FR2134456B1 (enExample) |
| GB (1) | GB1375266A (enExample) |
| IT (1) | IT952748B (enExample) |
| NL (1) | NL7205189A (enExample) |
-
1972
- 1972-03-24 CA CA138,096,A patent/CA951046A/en not_active Expired
- 1972-03-30 AU AU40604/72A patent/AU453009B2/en not_active Expired
- 1972-04-18 NL NL7205189A patent/NL7205189A/xx not_active Application Discontinuation
- 1972-04-20 DE DE19722219336 patent/DE2219336A1/de active Pending
- 1972-04-24 FR FR7214504A patent/FR2134456B1/fr not_active Expired
- 1972-04-24 IT IT4980872A patent/IT952748B/it active
- 1972-04-25 BR BR250372A patent/BR7202503D0/pt unknown
- 1972-04-26 GB GB1942272A patent/GB1375266A/en not_active Expired
- 1972-04-26 BE BE782685A patent/BE782685A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE782685A (fr) | 1972-10-26 |
| FR2134456A1 (enExample) | 1972-12-08 |
| BR7202503D0 (pt) | 1973-07-10 |
| GB1375266A (enExample) | 1974-11-27 |
| CA951046A (en) | 1974-07-09 |
| IT952748B (it) | 1973-07-30 |
| AU4060472A (en) | 1973-12-04 |
| AU453009B2 (en) | 1974-08-28 |
| NL7205189A (enExample) | 1972-10-30 |
| FR2134456B1 (enExample) | 1979-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |