KR20110039339A - 중합성 벤족사진 조성물 - Google Patents
중합성 벤족사진 조성물 Download PDFInfo
- Publication number
- KR20110039339A KR20110039339A KR1020117003126A KR20117003126A KR20110039339A KR 20110039339 A KR20110039339 A KR 20110039339A KR 1020117003126 A KR1020117003126 A KR 1020117003126A KR 20117003126 A KR20117003126 A KR 20117003126A KR 20110039339 A KR20110039339 A KR 20110039339A
- Authority
- KR
- South Korea
- Prior art keywords
- polymerizable composition
- formula
- benzoxazine
- nitrogen
- hydrogen
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 119
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims description 62
- 150000005130 benzoxazines Chemical class 0.000 claims abstract description 45
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- -1 benzoxazine compound Chemical class 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 239000000835 fiber Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229940126062 Compound A Drugs 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 16
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 150000003457 sulfones Chemical class 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 150000003573 thiols Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- QEQVCPKISCKMOQ-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine Chemical group C1=CC=CC2=C(C=CNO3)C3=CC=C21 QEQVCPKISCKMOQ-UHFFFAOYSA-N 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Chemical group C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003536 tetrazoles Chemical group 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000010348 incorporation Methods 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000011521 glass Substances 0.000 description 14
- 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 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 101000901617 Notophthalmus viridescens Homeobox protein DLX-3 Proteins 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241001598984 Bromius obscurus Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 2
- 229920003319 Araldite® Polymers 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- JPIGSMKDJQPHJC-UHFFFAOYSA-N 1-(2-aminoethoxy)ethanol Chemical compound CC(O)OCCN JPIGSMKDJQPHJC-UHFFFAOYSA-N 0.000 description 1
- IPLIJMUJLJBZDZ-UHFFFAOYSA-N 1-amino-3-imidazol-1-ylpropan-2-ol Chemical compound NCC(O)CN1C=CN=C1 IPLIJMUJLJBZDZ-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- YTDHEFNWWHSXSU-UHFFFAOYSA-N 2,3,5,6-tetrachloroaniline Chemical compound NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl YTDHEFNWWHSXSU-UHFFFAOYSA-N 0.000 description 1
- RIAIKPXVFURCBS-UHFFFAOYSA-N 2-(2,2,4-trimethylpentoxymethyl)oxirane Chemical compound CC(C)CC(C)(C)COCC1CO1 RIAIKPXVFURCBS-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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- NDUDHWBKFFJGMA-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propan-1-amine Chemical compound CC1=NC=CN1CCCN NDUDHWBKFFJGMA-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- QOHHOCDXTLIHPG-UHFFFAOYSA-N 4,4-diphenylcyclohexane-1,1-diol Chemical compound C1CC(O)(O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QOHHOCDXTLIHPG-UHFFFAOYSA-N 0.000 description 1
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- NAXUFNXWXFZVSI-UHFFFAOYSA-N 4-aminobutan-2-ol Chemical compound CC(O)CCN NAXUFNXWXFZVSI-UHFFFAOYSA-N 0.000 description 1
- JVZPYJSJSQIEOG-UHFFFAOYSA-N 4-imidazol-1-ylbutan-1-amine Chemical compound NCCCCN1C=CN=C1 JVZPYJSJSQIEOG-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- KYJSXYQQYWMITG-UHFFFAOYSA-N 7-aminoheptan-1-ol Chemical compound NCCCCCCCO KYJSXYQQYWMITG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920003329 Araldite® ECN 1400 Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08014512 | 2008-08-14 | ||
| EP08014512.1 | 2008-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110039339A true KR20110039339A (ko) | 2011-04-15 |
Family
ID=41228600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117003126A Withdrawn KR20110039339A (ko) | 2008-08-14 | 2009-08-12 | 중합성 벤족사진 조성물 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110189458A1 (https=) |
| EP (1) | EP2323995B1 (https=) |
| JP (1) | JP5484464B2 (https=) |
| KR (1) | KR20110039339A (https=) |
| CN (1) | CN102119154A (https=) |
| WO (1) | WO2010018198A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160023672A (ko) * | 2013-06-21 | 2016-03-03 | 닛산 가가쿠 고교 가부시키 가이샤 | 특정 말단구조를 갖는 중합체를 포함하는 열경화성 수지 조성물 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8288591B2 (en) | 2008-11-20 | 2012-10-16 | Designer Molecules, Inc. | Curing agents for epoxy resins |
| DE102009028099A1 (de) * | 2009-07-29 | 2011-02-03 | Henkel Ag & Co. Kgaa | Schlagzähmodifizierte Zusammensetzungen |
| WO2011116050A2 (en) * | 2010-03-17 | 2011-09-22 | Designer Molecules, Inc. | Curing agents for epoxy resins |
| CN105108929B (zh) * | 2010-04-13 | 2021-06-22 | 汉高知识产权控股有限责任公司 | 可固化的组合物、利用该组合物制备复合材料的方法以及制备表面光洁度优异且纤维固结高的复合材料的方法 |
| US9178237B2 (en) | 2010-12-14 | 2015-11-03 | Samsung Electronics Co., Ltd. | Conductive composition and method of preparation, polymer thereof, and electrode, electrolyte membrane and fuel cell including the composition or polymer |
| JP5923291B2 (ja) * | 2010-12-14 | 2016-05-24 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 伝導性作用基を有する化合物、その重合体、これを含んだ燃料電池用電極、これを含んだ燃料電池用電解質膜及びこれを採用した燃料電池 |
| US9416302B2 (en) * | 2012-09-28 | 2016-08-16 | 3M Innovative Properties Company | Polybenzoxazine composition |
| EP3240829B1 (en) * | 2014-12-29 | 2019-08-21 | Cytec Industries Inc. | Benzoxazines and compositions containing the same |
| CN107428708B (zh) * | 2015-03-04 | 2021-11-09 | 亨斯迈先进材料美国有限责任公司 | 苯并噁嗪低温可固化组合物 |
| BR112018001264B1 (pt) * | 2015-07-23 | 2022-04-19 | Huntsman Advanced Materials Americas Llc | Composição curável, processo para produção de uma composição curável, artigo curado, e, método para produção de um prepreg ou towpreg. |
| CN106518926B (zh) * | 2016-11-09 | 2018-08-14 | 湖北大学 | 一种含dopo的水溶性苯并恶嗪化合物的制备方法 |
| KR101997349B1 (ko) * | 2017-11-03 | 2019-07-05 | 주식회사 케이씨씨 | 에폭시 수지 조성물 |
| LU102316B1 (en) * | 2020-12-09 | 2022-06-13 | Luxembourg Inst Science & Tech List | Catalysts for benzoxazine |
| CN116745271A (zh) * | 2021-01-29 | 2023-09-12 | 本州化学工业株式会社 | 苯并噁嗪化合物的新型制造方法 |
| US20240279189A1 (en) * | 2021-01-29 | 2024-08-22 | Honshu Chemical Industry Co., Ltd. | Method for producing benzoxazine compound |
| CN116724027B (zh) * | 2021-01-29 | 2026-03-06 | 本州化学工业株式会社 | 新型苯并噁嗪化合物、含有该化合物的树脂原料组合物、固化性树脂组合物及其固化物 |
| US20240101522A1 (en) * | 2021-01-29 | 2024-03-28 | Honshu Chemical Industry Co., Ltd. | Novel method for producing benzoxazine compound |
| KR20230137341A (ko) | 2021-01-29 | 2023-10-04 | 혼슈우 카가쿠고교 가부시키가이샤 | 신규한 벤즈옥사진 화합물, 그것을 함유하는 수지 원료조성물, 경화성 수지 조성물 및 그의 경화물 |
| US20250051509A1 (en) | 2021-09-10 | 2025-02-13 | Honshu Chemical Industry Co., Ltd. | Curable resin composition, varnish, cured product, and method for producing cured product |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3433851C2 (de) * | 1984-09-14 | 1987-01-08 | Gurit-Essex Ag, Freienbach | Chemisch härtbare Harze aus 1-Oxa-3-aza-tetralin-Gruppen enthaltenden Verbindungen und cycloaliphatischen Epoxid-harzen, Verfahren zu deren Herstellung sowie Verwendung solcher Harze |
| DE58909626D1 (de) * | 1988-07-18 | 1996-04-25 | Gurit Essex Ag | Zu schwerentflammbaren und hochtemperaturbeständigen Kunststoffen härtbare Harze und Verfahren zu deren Herstellung |
| US5443911A (en) * | 1990-05-21 | 1995-08-22 | Gurit-Essex Ag | Curable resins comprising halogenated epoxy resins and 1-oxa-3-aza tetraline compounds, method for preparing and use of resins |
| EP0493310A1 (de) * | 1990-12-21 | 1992-07-01 | Gurit-Essex AG | Zu schwerentflammbaren Kunststoffen härtbare Harzmischungen und deren Verwendung |
| US5543516A (en) * | 1994-05-18 | 1996-08-06 | Edison Polymer Innovation Corporation | Process for preparation of benzoxazine compounds in solventless systems |
| JPH111604A (ja) * | 1997-06-11 | 1999-01-06 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
| US6225440B1 (en) * | 1998-06-26 | 2001-05-01 | Edison Polymer Innovation Corporation | Cationic ring-opening polymerization of benzoxazines |
| US6376080B1 (en) * | 1999-06-07 | 2002-04-23 | Loctite Corporation | Method for preparing polybenzoxazine |
| WO2001034581A1 (en) * | 1999-11-05 | 2001-05-17 | The Dow Chemical Company | High char yield benzoxazine compositions |
| US6437026B1 (en) * | 2001-01-05 | 2002-08-20 | Cookson Singapore Pte Ltd. | Hardener for epoxy molding compounds |
| US20030023007A1 (en) * | 2001-07-27 | 2003-01-30 | Hycomp, Inc. | Enhancement of thermal properties of benzoxazine polymers by use of aromatic polyamines to incorporate internal benzoxazine groups within the monomer |
| US6743852B2 (en) * | 2001-11-13 | 2004-06-01 | Henkel Corporation | Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof |
| US6620905B1 (en) * | 2002-02-23 | 2003-09-16 | National Starch And Chemical Investment Holding Corporation | Curable compositions containing benzoxazine |
| US20070191555A1 (en) * | 2004-03-30 | 2007-08-16 | Hatsuo Ishida | Thermosetting resin composition and its article |
| US20060025509A1 (en) * | 2004-07-29 | 2006-02-02 | Ruzhi Zhang | Fluxing no-flow underfill composition containing benzoxazines |
| US7649060B2 (en) * | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| EP2218748B1 (en) * | 2005-09-03 | 2012-10-10 | Samsung SDI Co., Ltd. | Polybenzoxazine-based compound, electrolyte membrane including the same, and fuel cell employing the electrolyte membrane |
| JP2007169587A (ja) * | 2005-11-24 | 2007-07-05 | Sekisui Chem Co Ltd | 繊維複合体及びその製造方法 |
| JP2008050557A (ja) * | 2005-11-24 | 2008-03-06 | Sekisui Chem Co Ltd | 繊維複合体及びその製造方法 |
| KR100754374B1 (ko) * | 2006-02-07 | 2007-08-31 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물을 이용한 전해질막 및 그제조방법 |
| KR100818255B1 (ko) * | 2006-05-29 | 2008-04-02 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물, 이를 포함한 전해질막 및 이를채용한 연료전지 |
| JP5409373B2 (ja) * | 2006-11-13 | 2014-02-05 | ヘンケル コーポレイション | コア−シェルゴムを有するベンゾキサジン組成物 |
| JP2008195907A (ja) * | 2007-02-16 | 2008-08-28 | Shikoku Chem Corp | 熱硬化性ベンゾオキサジン樹脂組成物 |
-
2009
- 2009-08-12 EP EP20090781761 patent/EP2323995B1/en not_active Not-in-force
- 2009-08-12 JP JP2011522512A patent/JP5484464B2/ja not_active Expired - Fee Related
- 2009-08-12 KR KR1020117003126A patent/KR20110039339A/ko not_active Withdrawn
- 2009-08-12 WO PCT/EP2009/060448 patent/WO2010018198A1/en not_active Ceased
- 2009-08-12 CN CN2009801313246A patent/CN102119154A/zh active Pending
-
2011
- 2011-02-14 US US13/026,639 patent/US20110189458A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160023672A (ko) * | 2013-06-21 | 2016-03-03 | 닛산 가가쿠 고교 가부시키 가이샤 | 특정 말단구조를 갖는 중합체를 포함하는 열경화성 수지 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011530570A (ja) | 2011-12-22 |
| EP2323995B1 (en) | 2012-11-21 |
| WO2010018198A1 (en) | 2010-02-18 |
| US20110189458A1 (en) | 2011-08-04 |
| JP5484464B2 (ja) | 2014-05-07 |
| CN102119154A (zh) | 2011-07-06 |
| EP2323995A1 (en) | 2011-05-25 |
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