CA2055880C - Fire retardant curable 1-oxa-3-aza tetraline (also termed "3,4-dihydro-1,3-benzoxazine") derived resin composition - Google Patents
Fire retardant curable 1-oxa-3-aza tetraline (also termed "3,4-dihydro-1,3-benzoxazine") derived resin compositionInfo
- Publication number
- CA2055880C CA2055880C CA002055880A CA2055880A CA2055880C CA 2055880 C CA2055880 C CA 2055880C CA 002055880 A CA002055880 A CA 002055880A CA 2055880 A CA2055880 A CA 2055880A CA 2055880 C CA2055880 C CA 2055880C
- Authority
- CA
- Canada
- Prior art keywords
- resin mixture
- mixture according
- compounds
- group
- compound
- 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.)
- Expired - Lifetime
Links
- WTAVYBAEMMFITK-UHFFFAOYSA-N 3,4-dihydro-2h-1,3-benzoxazine Chemical compound C1=CC=C2OCNCC2=C1 WTAVYBAEMMFITK-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000003063 flame retardant Substances 0.000 title description 10
- 239000011342 resin composition Substances 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 117
- 239000011347 resin Substances 0.000 claims abstract description 117
- 239000000203 mixture Substances 0.000 claims abstract description 93
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 20
- 239000002952 polymeric resin Substances 0.000 claims abstract description 19
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000000737 periodic effect Effects 0.000 claims abstract description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 8
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 8
- 239000010949 copper Substances 0.000 claims abstract description 8
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004744 fabric Substances 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 11
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 9
- 239000012783 reinforcing fiber Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 7
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920003986 novolac Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 238000007731 hot pressing Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- -1 phosphorus compound Chemical class 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 239000012209 synthetic fiber Substances 0.000 claims description 5
- 229920002994 synthetic fiber Polymers 0.000 claims description 5
- 239000003677 Sheet moulding compound Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical class C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 claims description 4
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 4
- 229910001679 gibbsite Inorganic materials 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000004291 polyenes Chemical class 0.000 claims description 4
- 150000004032 porphyrins Chemical class 0.000 claims description 4
- 239000010453 quartz Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 239000004917 carbon fiber Substances 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009730 filament winding Methods 0.000 claims description 3
- 238000001746 injection moulding Methods 0.000 claims description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 27
- 229940105305 carbon monoxide Drugs 0.000 claims 11
- 239000004414 compression moulding compound Substances 0.000 claims 6
- 229910052698 phosphorus Inorganic materials 0.000 claims 6
- 239000011574 phosphorus Substances 0.000 claims 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 4
- 150000004982 aromatic amines Chemical class 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- PGMJMZADHYDBQF-UHFFFAOYSA-H calcium magnesium barium(2+) tricarbonate Chemical compound [Ca+2].[Mg+2].C([O-])([O-])=O.[Ba+2].C([O-])([O-])=O.C([O-])([O-])=O PGMJMZADHYDBQF-UHFFFAOYSA-H 0.000 claims 2
- CXLSVMAGOLTCSL-UHFFFAOYSA-J calcium;barium(2+);dicarbonate Chemical compound [Ca+2].[Ba+2].[O-]C([O-])=O.[O-]C([O-])=O CXLSVMAGOLTCSL-UHFFFAOYSA-J 0.000 claims 2
- HHSPVTKDOHQBKF-UHFFFAOYSA-J calcium;magnesium;dicarbonate Chemical compound [Mg+2].[Ca+2].[O-]C([O-])=O.[O-]C([O-])=O HHSPVTKDOHQBKF-UHFFFAOYSA-J 0.000 claims 2
- 239000003365 glass fiber Substances 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 2
- 239000001095 magnesium carbonate Substances 0.000 claims 2
- GYLDZLVKMWTSGQ-UHFFFAOYSA-J magnesium;barium(2+);dicarbonate Chemical compound [Mg+2].[Ba+2].[O-]C([O-])=O.[O-]C([O-])=O GYLDZLVKMWTSGQ-UHFFFAOYSA-J 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 8
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 8
- 229960004279 formaldehyde Drugs 0.000 description 7
- 235000019256 formaldehyde Nutrition 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 5
- 229940039407 aniline Drugs 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005496 tempering Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N meta-ethylphenol Natural products CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N meta-isopropyl phenol Natural products CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- LVLNPXCISNPHLE-UHFFFAOYSA-N (2-Hydroxy-phenyl)-(4-hydroxy-phenyl)-methan Natural products C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 1
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- DXADWKPCWTXPOY-UHFFFAOYSA-N 3-[(3-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC(CC=2C=C(O)C=CC=2)=C1 DXADWKPCWTXPOY-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- QEYQMWSESURNPP-UHFFFAOYSA-N 4-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=C(O)C=C1 QEYQMWSESURNPP-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- 241001279686 Allium moly Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 101000824971 Homo sapiens Sperm surface protein Sp17 Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 102100022441 Sperm surface protein Sp17 Human genes 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940024545 aluminum hydroxide Drugs 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- UOCIZHQMWNPGEN-UHFFFAOYSA-N dialuminum;oxygen(2-);trihydrate Chemical compound O.O.O.[O-2].[O-2].[O-2].[Al+3].[Al+3] UOCIZHQMWNPGEN-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH410690 | 1990-12-21 | ||
| CH4106/90-0 | 1990-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2055880A1 CA2055880A1 (en) | 1992-06-22 |
| CA2055880C true CA2055880C (en) | 1996-11-26 |
Family
ID=4269935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002055880A Expired - Lifetime CA2055880C (en) | 1990-12-21 | 1991-11-20 | Fire retardant curable 1-oxa-3-aza tetraline (also termed "3,4-dihydro-1,3-benzoxazine") derived resin composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5200452A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0493310A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3336437B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100225374B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2055880C (cg-RX-API-DMAC7.html) |
| TW (1) | TW229220B (cg-RX-API-DMAC7.html) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3487083B2 (ja) * | 1996-02-09 | 2004-01-13 | 日立化成工業株式会社 | 熱硬化性樹脂組成物及びその硬化物 |
| JP3423170B2 (ja) * | 1996-12-26 | 2003-07-07 | 日立化成工業株式会社 | 熱硬化性樹脂組成物 |
| US7452585B1 (en) | 2000-07-21 | 2008-11-18 | Henkel Corporation | Monolithic structures, methods of manufacture and composite structures |
| US6743852B2 (en) * | 2001-11-13 | 2004-06-01 | Henkel Corporation | Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof |
| US7157509B2 (en) * | 2003-06-27 | 2007-01-02 | Henkel Corporation | Curable compositions |
| US20050042961A1 (en) * | 2003-08-18 | 2005-02-24 | Henkel Loctite Corporation | Curable compositions for advanced processes, and products made therefrom |
| DE102004046744B4 (de) | 2004-09-27 | 2007-05-24 | Atotech Deutschland Gmbh | Verfahren zur Übertragung von Pulvern und Pulverlacken auf Substrate und Verwendung zur Herstellung von Leiterplatten und Solarzellen |
| DE102004046745B4 (de) * | 2004-09-27 | 2008-04-24 | Atotech Deutschland Gmbh | Verfahren zur lösungsmittelfreien Herstellung einer faserverstärkten, mit Harz beschichteten Folie und Verwendung derselben |
| TWI374137B (en) * | 2004-09-28 | 2012-10-11 | Huntsman Adv Mat Switzerland | Organic compounds |
| US7666938B2 (en) * | 2004-12-03 | 2010-02-23 | Henkel Corporation | Nanoparticle silica filled benzoxazine compositions |
| US7649060B2 (en) * | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| US8029889B1 (en) | 2004-12-03 | 2011-10-04 | Henkel Corporation | Prepregs, towpregs and preforms |
| RU2399623C2 (ru) * | 2005-02-25 | 2010-09-20 | Хантсман Эдванст Матириалз (Свитзерланд) Гмбх | Производные бороксина в качестве огнезащитных соединений |
| WO2007008199A1 (en) * | 2005-07-08 | 2007-01-18 | Henkel Corporation | Primer compositions for adhesive bonding systems |
| KR100646939B1 (ko) * | 2005-08-29 | 2006-11-23 | 삼성에스디아이 주식회사 | 박막트랜지스터 및 그 제조방법 |
| US8318878B2 (en) * | 2006-09-21 | 2012-11-27 | Henkel Ag & Co. Kgaa | Benzoxazine-containing formulations polymerizable/curable at low temperature |
| US7759435B2 (en) * | 2006-09-26 | 2010-07-20 | Loctite (R&D) Limited | Adducts and curable compositions using same |
| KR101433982B1 (ko) | 2006-10-25 | 2014-08-25 | 헨켈 아일랜드 리미티드 | 이미늄염 및 이러한 신규 이미늄염을 사용하는 전자 결핍 올레핀의 제조 방법 |
| CA2669040C (en) | 2006-11-13 | 2014-10-07 | Henkel Corporation | Benzoxazine compositions with core shell rubbers |
| WO2008063611A2 (en) * | 2006-11-21 | 2008-05-29 | Henkel Corporation | Toughened binder compositions for use in advance processes |
| US7537827B1 (en) | 2006-12-13 | 2009-05-26 | Henkel Corporation | Prepreg laminates |
| CA2708261C (en) * | 2007-12-06 | 2016-02-02 | Stefan Kreiling | Curable compositions containing isocyanate-based tougheners |
| CN101889048B (zh) * | 2007-12-06 | 2012-09-05 | 汉高两合股份公司 | 基于苯并噁嗪的可固化组合物、它们的制备及其固化产物 |
| WO2009137144A2 (en) * | 2008-02-21 | 2009-11-12 | Huntsman Advanced Materials Americas Inc. | Halogen-free benzoxazine based curable compositions for high tg applications |
| US7847034B2 (en) * | 2008-03-20 | 2010-12-07 | Loctite (R&D) Limited | Adducts and curable compositions using same |
| DE102008023076A1 (de) * | 2008-05-09 | 2009-11-12 | Henkel Ag & Co. Kgaa | Polymerisierbare Zusammensetzung |
| DE102008031555A1 (de) | 2008-07-07 | 2010-01-14 | Henkel Ag & Co. Kgaa | Polymerisierbare Zusammensetzung enthaltend anorganische Partikel mit organischer Hülle |
| DE102008032176A1 (de) | 2008-07-09 | 2010-01-14 | Henkel Ag & Co. Kgaa | Polymerisierbare Zusammensetzung |
| EP2323995B1 (en) * | 2008-08-14 | 2012-11-21 | Henkel AG & Co. KGaA | Polymerizable benzoxazine compositions |
| PT2370219E (pt) | 2008-11-21 | 2014-10-03 | Henkel US IP LLC | Pós de metal revestidos com polímero termicamente decomponível |
| DE102009003033B4 (de) | 2009-05-12 | 2013-02-21 | Henkel Ag & Co. Kgaa | Polymerisierbare Benzoxazin-Verbindungen mit grenzflächenaktiven bzw. oberflächenaktiven Eigenschaften |
| DE102009003032A1 (de) | 2009-05-12 | 2010-11-18 | Henkel Ag & Co. Kgaa | Kationische Benzoxazin(co)polymere |
| US8853302B2 (en) * | 2009-05-14 | 2014-10-07 | Huntsman Advanced Materials Americas Llc | Liquid monobenzoxazine based resin system |
| DE102009028099A1 (de) | 2009-07-29 | 2011-02-03 | Henkel Ag & Co. Kgaa | Schlagzähmodifizierte Zusammensetzungen |
| JP5654026B2 (ja) | 2009-10-15 | 2015-01-14 | ヘンケル コーポレイションＨｅｎｋｅｌ Ｃｏｒｐｏｒａｔｉｏｎ | 嫌気硬化性組成物 |
| JP2013508486A (ja) | 2009-10-22 | 2013-03-07 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | ベンゾオキサジン化合物および熱活性化触媒としての環状構造を有するスルホン酸エステルを含有する硬化性組成物 |
| EP2314579A1 (en) | 2009-10-22 | 2011-04-27 | Henkel AG & Co. KGaA | Fast-curing benzoxazine compounds |
| WO2011050834A1 (en) | 2009-10-27 | 2011-05-05 | Henkel Ag & Co. Kgaa | Benzoxazine-containing compositions |
| CN103201079B (zh) | 2010-04-13 | 2015-09-09 | 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 |
| US9682447B2 (en) | 2010-08-20 | 2017-06-20 | Henkel IP & Holding GmbH | Organic acid- or latent organic acid-functionalized polymer-coated metal powders for solder pastes |
| EP2431438B1 (en) | 2010-09-20 | 2012-11-28 | Henkel AG & Co. KGaA | Electrically conductive adhesives |
| EP2336221A1 (en) | 2010-12-10 | 2011-06-22 | Henkel AG & Co. KGaA | Curable compositions |
| GB201101302D0 (en) | 2011-01-25 | 2011-03-09 | Cytec Tech Corp | Benzoxazine resins |
| EP2487215B1 (en) | 2011-02-11 | 2013-07-24 | Henkel AG & Co. KGaA | Electrically conductive adhesives comprising at least one metal precursor |
| CN102250383B (zh) * | 2011-06-28 | 2013-02-13 | 华南理工大学 | 含苯并噁嗪的无卤阻燃剂及含无卤阻燃剂的聚合物材料 |
| KR101879018B1 (ko) | 2011-09-06 | 2018-07-16 | 헨켈 아이피 앤드 홀딩 게엠베하 | 솔더 페이스트용 이- 또는 다-관능성 전자 결핍 올레핀 코팅된 금속 분말 |
| KR102011258B1 (ko) | 2012-02-17 | 2019-08-16 | 헌츠만 어드밴스드 머티리얼스 아메리카스 엘엘씨 | 벤족사진, 에폭시 및 무수물의 혼합물 |
| DE102012215510A1 (de) | 2012-08-31 | 2014-05-28 | Henkel Ag & Co. Kgaa | Flammgeschützte Benzoxazin-haltige Zusammensetzung |
| WO2014052255A1 (en) * | 2012-09-28 | 2014-04-03 | 3M Innovative Properties Company | Polybenzoxazine composition |
| JP6516731B2 (ja) | 2013-09-24 | 2019-05-22 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 熱分解有機層およびそれによって製造される導電性プリプレグ |
| WO2016031552A1 (ja) | 2014-08-29 | 2016-03-03 | 古河電気工業株式会社 | 導電性接着剤組成物 |
| CA2960646A1 (en) | 2014-09-12 | 2016-03-17 | Henkel IP & Holding GmbH | Cationically curable benzoxazine compositions |
| JP2018515629A (ja) | 2015-03-04 | 2018-06-14 | ハンツマン・アドバンスド・マテリアルズ・アメリカズ・エルエルシー | 低温硬化性ベンゾオキサジン組成物 |
| CN107995916B (zh) | 2015-07-23 | 2021-08-10 | 亨斯迈先进材料美国有限责任公司 | 可固化的苯并噁嗪组合物 |
| ES2982344T3 (es) | 2019-10-02 | 2024-10-15 | Toray Industries | Composición de resina de benzoxazina, producto preimpregnado y material compuesto reforzado con fibra |
| US20240043636A1 (en) | 2020-12-04 | 2024-02-08 | Toray Composite Materials America, Inc. | Prepreg and carbon fiber-reinforced composite material |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876208A (en) * | 1954-03-18 | 1959-03-03 | Shell Dev | Phenolic resin compositions containing a metal chelate and glass fiber impregnated therewith |
| US3655606A (en) * | 1971-04-01 | 1972-04-11 | American Cyanamid Co | Heat stabilization of polyimides formed from 3 4 - dicarboxy-1 2 3 4-tetrahydro-1-naphthalene succinic dianhydrides and diprimary diamines |
| JPS4944053A (cg-RX-API-DMAC7.html) * | 1972-09-04 | 1974-04-25 | ||
| US4501864A (en) * | 1983-12-22 | 1985-02-26 | Monsanto Company | Polymerizable compositions comprising polyamines and poly(dihydrobenzoxazines) |
| EP0149987A3 (en) * | 1983-12-22 | 1987-11-25 | Monsanto Company | Polymerizable compositions comprising polyamines and poly (dihydrobenzoxazines) |
| JPS60195153A (ja) * | 1984-03-16 | 1985-10-03 | Sekisui Chem Co Ltd | Ａｂｓ樹脂組成物 |
| 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 |
| US4812501A (en) * | 1986-04-23 | 1989-03-14 | Ciba-Geigy Corporation | 1,3,2-oxazaphospholidine stabilizers |
| JPS63128038A (ja) * | 1986-11-19 | 1988-05-31 | Mitsubishi Cable Ind Ltd | 難燃性樹脂組成物 |
| JPS63128043A (ja) * | 1986-11-19 | 1988-05-31 | Mitsubishi Cable Ind Ltd | 難燃性樹脂組成物 |
| JPH0791425B2 (ja) * | 1986-11-19 | 1995-10-04 | 三菱電線工業株式会社 | 難燃性樹脂組成物 |
| JPH0788444B2 (ja) * | 1986-11-19 | 1995-09-27 | 三菱電線工業株式会社 | 難燃性樹脂組成物 |
| JPS63128042A (ja) * | 1986-11-19 | 1988-05-31 | Mitsubishi Cable Ind Ltd | 難燃性樹脂組成物 |
| DE58909626D1 (de) * | 1988-07-18 | 1996-04-25 | Gurit Essex Ag | Zu schwerentflammbaren und hochtemperaturbeständigen Kunststoffen härtbare Harze und Verfahren zu deren Herstellung |
| DE4016296C1 (en) * | 1990-05-21 | 1991-09-05 | Gurit-Essex Ag, Freienbach, Ch | Flame retardant thermosetting adhesive for metals etc. - comprises oxa:aza:tetralin, halogenated epoxy] resins and opt. additives |
-
1991
- 1991-11-11 EP EP91810867A patent/EP0493310A1/de not_active Withdrawn
- 1991-11-18 US US07/793,817 patent/US5200452A/en not_active Expired - Lifetime
- 1991-11-20 CA CA002055880A patent/CA2055880C/en not_active Expired - Lifetime
- 1991-11-27 KR KR1019910021405A patent/KR100225374B1/ko not_active Expired - Lifetime
- 1991-12-16 JP JP33207691A patent/JP3336437B2/ja not_active Expired - Lifetime
- 1991-12-19 TW TW080109950A patent/TW229220B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR920012257A (ko) | 1992-07-25 |
| TW229220B (cg-RX-API-DMAC7.html) | 1994-09-01 |
| CA2055880A1 (en) | 1992-06-22 |
| JPH073121A (ja) | 1995-01-06 |
| KR100225374B1 (ko) | 1999-10-15 |
| JP3336437B2 (ja) | 2002-10-21 |
| US5200452A (en) | 1993-04-06 |
| EP0493310A1 (de) | 1992-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2055880C (en) | Fire retardant curable 1-oxa-3-aza tetraline (also termed "3,4-dihydro-1,3-benzoxazine") derived resin composition | |
| US5443911A (en) | Curable resins comprising halogenated epoxy resins and 1-oxa-3-aza tetraline compounds, method for preparing and use of resins | |
| US5021484A (en) | Fire retardant curable 1-oxa-3-aza tetraline (also termed "3,4-dihydro-1,3-benzoxazine") derived resin composition | |
| US2950266A (en) | Cross-linked polycarbonate resinous compositions and method for preparing same | |
| CA1316627C (en) | Metal acetylacetonate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols | |
| AU636226B2 (en) | Resins which may be cured to form polymeric resins which are difficultly inflammable and resistant to high temperatures, method for preparing and use of said polymeric resins | |
| US3355511A (en) | Flame retardant epoxy compositions containing polyglycidyl ethers of hexahalo bicycloheptadiene bisphenols | |
| CA1057441A (en) | Flame resistant thermosetting resin composition and metal clad laminate composed of the thermosetting resin composition | |
| US4759978A (en) | Epoxy resin composition | |
| EP0155517B1 (en) | Polyester composition and process for producing shaped articles using same | |
| KR0139001B1 (ko) | 방향족 디아민 경화제를 포함하는 에폭시 수지 조성물 | |
| US3839300A (en) | Aromatic resins | |
| US4916203A (en) | Curable resin composition from epoxy compound and propargyl aromatic ether | |
| US5015719A (en) | Aromatic dicyanate/aromatic diepoxy compositions, cured products and methods | |
| JPH0539370A (ja) | ポリアリーレンスルフイド系樹脂プリプレーグ及びその成形品 | |
| US3370023A (en) | Curable composition comprising rubber and the co-condensation product of an aromatic hydrocarbon-aldehyde resin and a terpene phenol | |
| KR0153777B1 (ko) | 내열난연성 에폭시 수지조성물 | |
| JPH0468313B2 (cg-RX-API-DMAC7.html) | ||
| US3755210A (en) | Cellular polymeric materials | |
| JPH0125494B2 (cg-RX-API-DMAC7.html) | ||
| JPH0543629A (ja) | 耐熱性樹脂組成物 | |
| CA1048676A (en) | Resin composition comprising aralkylene phenol resin and formaldehyde condensate | |
| JP2702226B2 (ja) | 耐熱難燃性エポキシ樹脂組成物 | |
| JPH05114502A (ja) | 電子部品封止用材料 | |
| JPH0125496B2 (cg-RX-API-DMAC7.html) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |