DE1966743A1 - Neue mono- bzw. dialkohole von nheterocyclischen verbindungen - Google Patents
Neue mono- bzw. dialkohole von nheterocyclischen verbindungenInfo
- Publication number
- DE1966743A1 DE1966743A1 DE19691966743 DE1966743A DE1966743A1 DE 1966743 A1 DE1966743 A1 DE 1966743A1 DE 19691966743 DE19691966743 DE 19691966743 DE 1966743 A DE1966743 A DE 1966743A DE 1966743 A1 DE1966743 A1 DE 1966743A1
- Authority
- DE
- Germany
- Prior art keywords
- hours
- mixture
- mol
- vsm
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title description 20
- -1 β-hydroxyethoxyethoxyethyl Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- ATIAIEWDRRJGSL-UHFFFAOYSA-N 1,3-bis(2-hydroxyethyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(CCO)C(=O)N(CCO)C1=O ATIAIEWDRRJGSL-UHFFFAOYSA-N 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- KVQUADFBNUQFNX-UHFFFAOYSA-N 1,3-bis(2-hydroxypropyl)-5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1N(CC(C)O)C(=O)N(CC(C)O)C1=O KVQUADFBNUQFNX-UHFFFAOYSA-N 0.000 claims description 2
- IZEUNSNECKZMNL-UHFFFAOYSA-N 5,5-dimethyl-6-propan-2-yl-1,3-diazinane-2,4-dione Chemical compound CC(C)C1NC(=O)NC(=O)C1(C)C IZEUNSNECKZMNL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- FZTQHUJTDIINEP-UHFFFAOYSA-N 5,5-diethyl-1,3-bis(2-hydroxypropyl)-1,3-diazinane-2,4,6-trione Chemical compound CCC1(CC)C(=O)N(CC(C)O)C(=O)N(CC(C)O)C1=O FZTQHUJTDIINEP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 97
- 239000000203 mixture Substances 0.000 description 79
- 239000000243 solution Substances 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 34
- 229920005989 resin Polymers 0.000 description 33
- 239000011347 resin Substances 0.000 description 33
- 150000002118 epoxides Chemical group 0.000 description 31
- 235000011121 sodium hydroxide Nutrition 0.000 description 31
- 238000003756 stirring Methods 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000004593 Epoxy Substances 0.000 description 29
- 229920000647 polyepoxide Polymers 0.000 description 29
- 239000003822 epoxy resin Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 24
- 230000009102 absorption Effects 0.000 description 23
- 238000010521 absorption reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 20
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 20
- 229910052782 aluminium Inorganic materials 0.000 description 19
- 235000002639 sodium chloride Nutrition 0.000 description 18
- 238000004821 distillation Methods 0.000 description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 14
- 229940091173 hydantoin Drugs 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- 241000428199 Mustelinae Species 0.000 description 12
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 238000000465 moulding Methods 0.000 description 11
- XZYMCKIPUJEQSY-UHFFFAOYSA-N [Na+].[Na+].[Na+].CCCCCC([O-])([O-])[O-] Chemical compound [Na+].[Na+].[Na+].CCCCCC([O-])([O-])[O-] XZYMCKIPUJEQSY-UHFFFAOYSA-N 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 8
- 238000005266 casting Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000004848 polyfunctional curative Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- FQCOFQIGUJZEJO-UHFFFAOYSA-N 1,3-bis(2-hydroxypropyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC(O)CN1C(=O)N(CC(C)O)C(C)(C)C1=O FQCOFQIGUJZEJO-UHFFFAOYSA-N 0.000 description 4
- VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 4
- 239000008240 homogeneous mixture Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 3
- 229910014570 C—OH Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000007656 barbituric acids Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011346 highly viscous material Substances 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 3
- 229940035893 uracil Drugs 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
- HTKIZIQFMHVTRJ-UHFFFAOYSA-N 5-butyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC1C(=O)NC(=O)NC1=O HTKIZIQFMHVTRJ-UHFFFAOYSA-N 0.000 description 2
- VMAQYKGITHDWKL-UHFFFAOYSA-N 5-methylimidazolidine-2,4-dione Chemical compound CC1NC(=O)NC1=O VMAQYKGITHDWKL-UHFFFAOYSA-N 0.000 description 2
- PBNUQCWZHRMSMS-UHFFFAOYSA-N 5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1NC(=O)NC1=O PBNUQCWZHRMSMS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- 229960002319 barbital Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- 229920003986 novolac Polymers 0.000 description 2
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- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
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- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
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- 239000012264 purified product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 1
- 239000013008 thixotropic agent 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- 238000000214 vapour pressure osmometry Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/10—Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds 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
- C08G59/20—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 epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/908—Polymer containing a hydantoin group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Organic Insulating Materials (AREA)
- Laminated Bodies (AREA)
- Polyethers (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1680368A CH523278A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Diglycidyläthern von N-heterocyclischen Verbindungen und deren Verwendung |
| CH1662271A CH523279A (de) | 1968-11-11 | 1968-11-11 | Verfahren zur Herstellung von neuen Diglycidylverbindungen von N-heterocyclischen Verbindungen und deren Verwendung |
| CH134870A CH557398A (de) | 1968-11-11 | 1970-01-30 | Epoxidharzmischung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1966743A1 true DE1966743A1 (de) | 1973-11-15 |
Family
ID=27172919
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691966743 Ceased DE1966743A1 (de) | 1968-11-11 | 1969-10-29 | Neue mono- bzw. dialkohole von nheterocyclischen verbindungen |
| DE19702020091 Pending DE2020091A1 (de) | 1968-11-11 | 1970-04-24 | Epoxidharzmischungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702020091 Pending DE2020091A1 (de) | 1968-11-11 | 1970-04-24 | Epoxidharzmischungen |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US3629263A (en:Method) |
| AT (3) | AT296331B (en:Method) |
| BE (2) | BE741506A (en:Method) |
| CH (3) | CH523278A (en:Method) |
| DE (2) | DE1966743A1 (en:Method) |
| FR (2) | FR2022997A1 (en:Method) |
| GB (3) | GB1290728A (en:Method) |
| NL (2) | NL6916903A (en:Method) |
| SE (1) | SE391924B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016175668A1 (en) | 2015-04-28 | 2016-11-03 | Politechnika Rzeszowska | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161594A (en) * | 1968-11-11 | 1979-07-17 | Ciba-Geigy Ag | Dialcohols |
| US3882137A (en) * | 1969-11-18 | 1975-05-06 | Ciba Geigy Corp | Bis-hydantoin dialcohols |
| CH532158A (de) * | 1969-12-10 | 1972-12-31 | Ciba Geigy Ag | Verwendung N-heterocyclischer Perfluoralkylmonocarbonsäureester zum Veredeln von textilem Fasermaterial |
| US3948916A (en) * | 1970-04-20 | 1976-04-06 | Ciba-Geigy Ag | Diglycidyl compounds of N-heterocyclic compounds |
| CH547820A (de) * | 1970-05-22 | 1974-04-11 | Ciba Geigy Ag | Verfahren zur herstellung von neuen 5-nitrofurylderivaten. |
| US3852302A (en) * | 1971-04-16 | 1974-12-03 | Ciba Geigy Corp | Diacrylic acid ester derivatives of hydantoin compounds |
| US4024146A (en) * | 1971-04-16 | 1977-05-17 | Ciba-Geigy Corporation | Diacrylic acid ester derivatives of uracil compounds |
| US4001236A (en) * | 1972-06-23 | 1977-01-04 | Ciba-Geigy Corporation | Polyglycidyl compounds containing n-heterocyclic structure |
| US3956309A (en) * | 1972-06-23 | 1976-05-11 | Ciba-Geigy Corporation | Polyglycidyl compounds containing N-heterocyclic structure |
| CH581131A5 (en:Method) * | 1972-06-23 | 1976-10-29 | Ciba Geigy Ag | |
| DE2245345A1 (de) * | 1972-09-15 | 1974-03-21 | Bayer Ag | Hydantoinringe enthaltende polyaetherurethane und deren verwendung als antistatika |
| GB1446089A (en) * | 1972-12-12 | 1976-08-11 | Ciba Geigy Ag | Adducts of polyglycidyl compounds and phosphonoalkyl derivatives of cyclic ureides |
| US3920685A (en) * | 1972-12-12 | 1975-11-18 | Ciba Geigy Corp | Dialkoxyphosphonalkyl derivatives of cyclicureides containing glycidyl groups |
| US3943109A (en) * | 1972-12-29 | 1976-03-09 | Ciba-Geigy Corporation | Diglycidylbenzimidiazolones |
| US3939125A (en) * | 1972-12-29 | 1976-02-17 | Ciba-Geigy Corporation | Diglycidylimidazolidones |
| SE7411007L (en:Method) * | 1973-10-10 | 1975-04-11 | Ciba Geigy Ag | |
| US4093809A (en) * | 1976-06-21 | 1978-06-06 | Ciba-Geigy Corporation | 5-Substituted phosphonate hydantoins and derivatives thereof |
| US4144120A (en) | 1976-06-25 | 1979-03-13 | Ciba-Geigy Corporation | Method for treating paper with a composition containing hydantoin compounds and a copolymer |
| US4145247A (en) | 1976-06-25 | 1979-03-20 | Ciba-Geigy Corporation | Composition, for the treatment of paper, which contains hydantoin compounds and an amine curing agent |
| US4167465A (en) * | 1976-08-04 | 1979-09-11 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
| US4104238A (en) * | 1976-11-23 | 1978-08-01 | Westinghouse Electric Corp. | Silica-alumina trihydrate filled epoxy castings resistant to arced SF6 |
| US4214928A (en) * | 1976-11-29 | 1980-07-29 | The United States Of America As Represented By The Secretary Of The Navy | Dimethyl hydantoin bonding agents in solid propellants |
| CH633779A5 (de) * | 1977-07-07 | 1982-12-31 | Ciba Geigy Ag | Verfahren zur herstellung neuer vinylaether und deren verwendung zur herstellung von polymeren. |
| US4258149A (en) * | 1978-03-13 | 1981-03-24 | Ciba-Geigy Corporation | Process for curing saturated polymers using divinyl hydantoin coagents |
| US4286097A (en) * | 1978-07-28 | 1981-08-25 | Ciba-Geigy Corporation | Carboxylic acid dianhydrides based on trimellitic anhydride |
| US4228294A (en) * | 1978-10-10 | 1980-10-14 | Ppg Industries, Inc. | Esters of imidazolidinedione-based diepoxides and coating compositions containing same |
| US4174337A (en) * | 1978-10-10 | 1979-11-13 | Ppg Industries, Inc. | Hydroxy-functional esters of substituted imidazolidinediones and compositions containing same |
| DE2908627A1 (de) * | 1979-03-06 | 1980-09-11 | Bayer Ag | Neue trishydroxyalkylheterocyclen |
| GB2046244A (en) * | 1979-04-10 | 1980-11-12 | Lim Holding Sa | Novel diisatoic and triisatoic acid derivatives |
| US4629779A (en) * | 1983-10-27 | 1986-12-16 | Union Carbide Corporation | Low viscosity adducts of a polycaprolactone polyol and a polyepoxide |
| US4786705A (en) * | 1983-10-27 | 1988-11-22 | Union Carbide Corporation | Low viscosity adducts of a poly(active hydrogen) organic compound and a polyepoxide |
| US4725653A (en) * | 1983-10-27 | 1988-02-16 | Union Carbide Corporation | Low viscosity adducts of a polycaprolactone polyol and a polyepoxide |
| US4599401A (en) * | 1983-10-27 | 1986-07-08 | Union Carbide Corporation | Low viscosity adducts of poly(active hydrogen) organic compounds and a polyepoxide |
| US4707535A (en) * | 1983-10-27 | 1987-11-17 | Union Carbide Corporation | Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide |
| AU578068B2 (en) * | 1984-03-08 | 1988-10-13 | Nippon Zoki Pharmaceutical Co., Ltd. | Hydantoin derivatives and pharmaceutical compositions containing them |
| US4691021A (en) * | 1985-09-09 | 1987-09-01 | The Dow Chemical Company | Aminoalkyl hydantoins and glycidyl derivatives thereof |
| US4672101A (en) * | 1985-09-09 | 1987-06-09 | The Dow Chemical Company | Polyepoxy aromatic hydantoins |
| US5489315A (en) * | 1994-09-19 | 1996-02-06 | Shell Oil Company | Fuel compositions comprising hydantoin-containing polyether alcohol additives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3088948A (en) * | 1963-05-07 | Production of tris | ||
| US2211001A (en) * | 1937-03-18 | 1940-08-13 | Gen Aniline & Film Corp | Oxalkyl derivatives of imidazolines |
| US2890132A (en) * | 1954-11-03 | 1959-06-09 | John A Howsmon | Producing all skin viscose rayon |
| US3018246A (en) * | 1958-02-03 | 1962-01-23 | Petrolite Corp | Process of preventing corrosion |
| US3216957A (en) * | 1962-08-14 | 1965-11-09 | Union Carbide Corp | Antistatic thermoplastic vinyl resin compositions comprising oxyalkylated imidazolines |
| US4161594A (en) * | 1968-11-11 | 1979-07-17 | Ciba-Geigy Ag | Dialcohols |
-
1968
- 1968-11-11 CH CH1680368A patent/CH523278A/de not_active IP Right Cessation
- 1968-11-11 CH CH1662271A patent/CH523279A/de not_active IP Right Cessation
-
1969
- 1969-10-29 DE DE19691966743 patent/DE1966743A1/de not_active Ceased
- 1969-11-04 FR FR6937821A patent/FR2022997A1/fr not_active Withdrawn
- 1969-11-04 US US870547A patent/US3629263A/en not_active Expired - Lifetime
- 1969-11-10 GB GB1290728D patent/GB1290728A/en not_active Expired
- 1969-11-10 BE BE741506D patent/BE741506A/xx unknown
- 1969-11-10 AT AT896070A patent/AT296331B/de not_active IP Right Cessation
- 1969-11-10 AT AT1052869A patent/AT293433B/de not_active IP Right Cessation
- 1969-11-10 GB GB1290729D patent/GB1290729A/en not_active Expired
- 1969-11-10 SE SE7210622A patent/SE391924B/xx unknown
- 1969-11-10 NL NL6916903A patent/NL6916903A/xx not_active Application Discontinuation
-
1970
- 1970-01-30 CH CH134870A patent/CH557398A/xx not_active IP Right Cessation
- 1970-04-14 FR FR7013419A patent/FR2077627B2/fr not_active Expired
- 1970-04-24 DE DE19702020091 patent/DE2020091A1/de active Pending
- 1970-05-06 AT AT410770A patent/AT298807B/de not_active IP Right Cessation
- 1970-05-06 NL NL7006624A patent/NL7006624A/xx not_active Application Discontinuation
- 1970-05-08 GB GB22480/70A patent/GB1291187A/en not_active Expired
- 1970-05-08 BE BE750116D patent/BE750116R/xx active
- 1970-05-14 US US37299A patent/US3631221A/en not_active Expired - Lifetime
-
1971
- 1971-12-20 US US00210211A patent/US3772326A/en not_active Expired - Lifetime
-
1978
- 1978-10-31 US US05/956,523 patent/US4227005A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016175668A1 (en) | 2015-04-28 | 2016-11-03 | Politechnika Rzeszowska | Preparation method for 1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione and 1-phenyl-2,6-bis(2-hydroxypropyl)imidazo[1,5-c]quinazoline-3,5-dione |
Also Published As
| Publication number | Publication date |
|---|---|
| US3629263A (en) | 1971-12-21 |
| GB1290729A (en:Method) | 1972-09-27 |
| DE2020091A1 (de) | 1971-08-19 |
| NL6916903A (en:Method) | 1970-05-13 |
| US3631221A (en) | 1971-12-28 |
| US4227005A (en) | 1980-10-07 |
| FR2077627B2 (en:Method) | 1976-01-16 |
| GB1291187A (en) | 1972-10-04 |
| NL7006624A (en:Method) | 1971-08-03 |
| AT293433B (de) | 1971-10-11 |
| CH523279A (de) | 1972-05-31 |
| GB1290728A (en:Method) | 1972-09-27 |
| FR2022997A1 (en:Method) | 1970-08-07 |
| AT296331B (de) | 1972-02-10 |
| CH523278A (de) | 1972-05-31 |
| CH557398A (de) | 1974-12-31 |
| FR2077627A2 (en:Method) | 1971-10-29 |
| BE741506A (en:Method) | 1970-05-11 |
| US3772326A (en) | 1973-11-13 |
| SE391924B (sv) | 1977-03-07 |
| AT298807B (de) | 1972-05-25 |
| BE750116R (fr) | 1970-11-09 |
Similar Documents
| Publication | Publication Date | Title |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| 8131 | Rejection |