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 |
|---|---|---|---|
| CH4106/90-0 | 1990-12-21 | ||
| CH410690 | 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 (enExample) |
| EP (1) | EP0493310A1 (enExample) |
| JP (1) | JP3336437B2 (enExample) |
| KR (1) | KR100225374B1 (enExample) |
| CA (1) | CA2055880C (enExample) |
| TW (1) | TW229220B (enExample) |
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| 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 |
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| 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 |
| DE102004046745B4 (de) * | 2004-09-27 | 2008-04-24 | Atotech Deutschland Gmbh | Verfahren zur lösungsmittelfreien Herstellung einer faserverstärkten, mit Harz beschichteten Folie und Verwendung derselben |
| 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 |
| 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 |
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| CN101516922B (zh) * | 2006-09-21 | 2013-03-06 | 汉高两合股份公司 | 在低温下能够聚合/固化的含苯并噁嗪的制剂 |
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| JP2010510110A (ja) * | 2006-11-21 | 2010-04-02 | ヘンケル コーポレイション | 最新方法で使用するための強化バインダー組成物 |
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| CA2708081C (en) * | 2007-12-06 | 2016-06-14 | Henkel Ag & Co. Kgaa | Curable benzoxazine-based compositions, their preparation and cured products thereof |
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| US8975318B2 (en) * | 2008-02-21 | 2015-03-10 | Huntsman Advanced Materials Americas Llc | Halogen-free benzoxazine based curable compositions for high TG applications |
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| CN102119154A (zh) * | 2008-08-14 | 2011-07-06 | 汉高股份有限及两合公司 | 可聚合的苯并噁嗪组合物 |
| ES2498718T3 (es) | 2008-11-21 | 2014-09-25 | Henkel US IP LLC | Polvos metálicos recubiertos de polímero térmicamente descomponible |
| 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 |
| WO2010132772A1 (en) * | 2009-05-14 | 2010-11-18 | Huntsman Advanced Materials Americas Llc | Liquid monobenzoxazine based resin system |
| DE102009028099A1 (de) | 2009-07-29 | 2011-02-03 | Henkel Ag & Co. Kgaa | Schlagzähmodifizierte Zusammensetzungen |
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| WO2011047939A1 (en) | 2009-10-22 | 2011-04-28 | Henkel Ag & Co. Kgaa | Curable composition comprising a benzoxazine compound and a sulfonic acid ester having a cyclic structure as a heat-activatable catalyst |
| KR20120099024A (ko) | 2009-10-27 | 2012-09-06 | 헨켈 아게 운트 코. 카게아아 | 벤족사진-함유 조성물 |
| ES2851010T3 (es) | 2010-04-13 | 2021-09-02 | Henkel IP & Holding GmbH | Procedimientos para preparar materiales compuestos que tienen acabado de superficie superior y alta consolidación de fibras |
| 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 |
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| 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 |
| CN103945961B (zh) | 2011-09-06 | 2017-01-18 | 汉高知识产权控股有限责任公司 | 用于焊膏的涂覆有二官能或多官能缺电子烯烃的金属粉末 |
| JP6273213B2 (ja) | 2012-02-17 | 2018-01-31 | 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 | ベンズオキサジン、エポキシ及び無水物の混合物 |
| DE102012215510A1 (de) | 2012-08-31 | 2014-05-28 | Henkel Ag & Co. Kgaa | Flammgeschützte Benzoxazin-haltige Zusammensetzung |
| US9416302B2 (en) * | 2012-09-28 | 2016-08-16 | 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 |
| EP3187560B1 (en) | 2014-08-29 | 2024-01-17 | Furukawa Electric Co., Ltd. | Electrically conductive adhesive composition |
| WO2016040541A1 (en) | 2014-09-12 | 2016-03-17 | Henkel IP & Holding GmbH | Cationically curable benzoxazine compositions |
| ES2943008T3 (es) | 2015-03-04 | 2023-06-08 | Huntsman Advanced Mat Americas Llc | Composición de benzoxazina curable a baja temperatura |
| 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. |
| JP7613459B2 (ja) | 2019-10-02 | 2025-01-15 | 東レ株式会社 | ベンゾオキサジン樹脂組成物、プリプレグ、及び繊維強化複合材料 |
| WO2022120053A1 (en) | 2020-12-04 | 2022-06-09 | 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 (enExample) * | 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 |
| 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 |
| 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 |
| JPS63128042A (ja) * | 1986-11-19 | 1988-05-31 | Mitsubishi Cable Ind Ltd | 難燃性樹脂組成物 |
| EP0356379B1 (de) * | 1988-07-18 | 1996-03-20 | 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 |
|---|---|
| US5200452A (en) | 1993-04-06 |
| EP0493310A1 (de) | 1992-07-01 |
| KR100225374B1 (ko) | 1999-10-15 |
| CA2055880A1 (en) | 1992-06-22 |
| JP3336437B2 (ja) | 2002-10-21 |
| JPH073121A (ja) | 1995-01-06 |
| TW229220B (enExample) | 1994-09-01 |
| KR920012257A (ko) | 1992-07-25 |
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| MKEX | Expiry |