JPS6036212B2 - 燃焼遅廷性エポキシ樹脂 - Google Patents
燃焼遅廷性エポキシ樹脂Info
- Publication number
- JPS6036212B2 JPS6036212B2 JP57081678A JP8167882A JPS6036212B2 JP S6036212 B2 JPS6036212 B2 JP S6036212B2 JP 57081678 A JP57081678 A JP 57081678A JP 8167882 A JP8167882 A JP 8167882A JP S6036212 B2 JPS6036212 B2 JP S6036212B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- mol
- phosphine oxide
- hydroxypropyl
- resin
- 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
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 64
- 229920000647 polyepoxide Polymers 0.000 title claims description 64
- 238000002485 combustion reaction Methods 0.000 title description 7
- 230000003111 delayed effect Effects 0.000 title description 2
- SZTDSGCADFWGKM-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphoryl]propan-1-ol Chemical compound OCCCP(=O)(CCCO)CCCO SZTDSGCADFWGKM-UHFFFAOYSA-N 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical group NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003063 flame retardant Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 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 claims description 7
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 7
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 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 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- YWTFOHHOVZEFHA-UHFFFAOYSA-N 3-bis(3-hydroxy-2-methylpropyl)phosphoryl-2-methylpropan-1-ol Chemical compound OCC(C)CP(=O)(CC(C)CO)CC(C)CO YWTFOHHOVZEFHA-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- FGYHQFZISBDLDR-UHFFFAOYSA-N OCCC[PH2]=O Chemical compound OCCC[PH2]=O FGYHQFZISBDLDR-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 229920005989 resin Polymers 0.000 description 28
- 239000011347 resin Substances 0.000 description 28
- 230000009477 glass transition Effects 0.000 description 25
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000011521 glass Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 150000008064 anhydrides Chemical class 0.000 description 13
- 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 13
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 9
- 239000004744 fabric Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- -1 dicyandiamide or 4 Chemical class 0.000 description 6
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 239000012456 homogeneous solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 239000000654 additive Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OLTMTZWPLUTCDV-UHFFFAOYSA-N 3-[butan-2-yl(3-hydroxypropyl)phosphoryl]propan-1-ol Chemical compound OCCCP(=O)(C(C)CC)CCCO OLTMTZWPLUTCDV-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- 239000005041 Mylar™ Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000124033 Salix Species 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- ASFYPVGAALGVNR-AATRIKPKSA-N (e)-hept-2-en-1-ol Chemical compound CCCC\C=C\CO ASFYPVGAALGVNR-AATRIKPKSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- ASFYPVGAALGVNR-UHFFFAOYSA-N 2-Hepten-1-ol Natural products CCCCC=CCO ASFYPVGAALGVNR-UHFFFAOYSA-N 0.000 description 1
- KURWIEWPUMFWKP-UHFFFAOYSA-N 2-methoxyhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)OC KURWIEWPUMFWKP-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- YICAEXQYKBMDNH-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphanyl]propan-1-ol Chemical compound OCCCP(CCCO)CCCO YICAEXQYKBMDNH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KFDATXAEMFCUSA-UHFFFAOYSA-N CCC(C)[PH2]=O Chemical compound CCC(C)[PH2]=O KFDATXAEMFCUSA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000449980 Mansa Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- IOUQKAGSUTVTPK-UHFFFAOYSA-M tris(3-hydroxypropyl)-methylphosphanium;chloride Chemical compound [Cl-].OCCC[P+](C)(CCCO)CCCO IOUQKAGSUTVTPK-UHFFFAOYSA-M 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009756 wet lay-up Methods 0.000 description 1
Classifications
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/264,256 US4345059A (en) | 1981-05-18 | 1981-05-18 | Fire retardant epoxy resins containing 3-hydroxyalkylphosphine oxides |
| US264256 | 1981-05-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57195141A JPS57195141A (en) | 1982-11-30 |
| JPS6036212B2 true JPS6036212B2 (ja) | 1985-08-19 |
Family
ID=23005226
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57081678A Expired JPS6036212B2 (ja) | 1981-05-18 | 1982-05-17 | 燃焼遅廷性エポキシ樹脂 |
| JP60004192A Granted JPS60166457A (ja) | 1981-05-18 | 1985-01-16 | 燃焼遅延性エポキシ樹脂積層品とその製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60004192A Granted JPS60166457A (ja) | 1981-05-18 | 1985-01-16 | 燃焼遅延性エポキシ樹脂積層品とその製造法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4345059A (enExample) |
| EP (1) | EP0066171B1 (enExample) |
| JP (2) | JPS6036212B2 (enExample) |
| KR (1) | KR860000214B1 (enExample) |
| AR (1) | AR228093A1 (enExample) |
| AT (1) | ATE21409T1 (enExample) |
| AU (1) | AU552464B2 (enExample) |
| BR (1) | BR8202845A (enExample) |
| CA (1) | CA1184699A (enExample) |
| DE (1) | DE3272549D1 (enExample) |
| ES (1) | ES512269A0 (enExample) |
| NO (1) | NO821628L (enExample) |
| ZA (1) | ZA823441B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4621123A (en) * | 1984-12-20 | 1986-11-04 | Sumitomo Chemical Company, Limited | Phosphinylmethyl polypenols and polyglycidyl ethers thereof |
| CA1311496C (en) * | 1988-03-28 | 1992-12-15 | Allan James Robertson | 1,4-disubstituted-2,3,5,6-tetrahydroxy-1, 4-diphosphorinanes and their oxides or sulfides |
| US5086156A (en) * | 1989-10-06 | 1992-02-04 | Virginia Tech Intellectual Properties, Inc. | Novel phosphorus containing epoxy networks based on trihydrocarbyl phosphine oxides having active substituents |
| US4973631A (en) * | 1989-10-06 | 1990-11-27 | Virginia Tech Intellectual Properties Inc. | Novel phosphorus containing epoxy networks |
| US5084546A (en) * | 1990-12-12 | 1992-01-28 | American Cyanamid Company | Fire retardant epoxy resin compositions containing methylol substituted phosphine oxides |
| GB9106505D0 (en) * | 1991-03-27 | 1991-05-15 | Shell Int Research | A flame-retardant composition |
| EP0675131B1 (en) * | 1994-03-24 | 1999-12-01 | Shell Internationale Researchmaatschappij B.V. | Fire retardant epoxy resin composition |
| WO2001042253A2 (en) * | 1999-12-13 | 2001-06-14 | The Dow Chemical Company | Phosphorus element-containing crosslinking agents and flame retardant phosphorus element-containing epoxy resin compositions prepared therewith |
| DE10064890A1 (de) * | 2000-12-23 | 2002-06-27 | Trespa Int Bv | Plattenförmiges Formteil, Verfahren zu seiner Herstellung und seine Verwendung |
| KR100701455B1 (ko) * | 2001-02-15 | 2007-03-29 | 그레이트 레이크스 케미칼 코포레이션 | 하이드록시아릴 포스핀 옥사이드의 혼합물 및 이의 제조방법, 및 이로부터 유도된 에폭시 올리고머 생성물, 난연성 에폭시 조성물, 수지-함침된 복합물 및 적층물 |
| US6887950B2 (en) * | 2001-02-15 | 2005-05-03 | Pabu Services, Inc. | Phosphine oxide hydroxyaryl mixtures with novolac resins for co-curing epoxy resins |
| WO2003099900A1 (fr) * | 2002-05-29 | 2003-12-04 | Nippon Chemical Industrial Co., Ltd. | Resine epoxy contenant du phosphore, composition a base de ladite resine, procede de fabrication, materiau et stratifie d'etancheification renfermant cette resine ou fabriquee a partir de cette resine |
| CN100465196C (zh) * | 2005-10-31 | 2009-03-04 | 杭州师范学院 | 一种采用离子液体聚合引发体系制备高分子化合物的方法 |
| CA2696950A1 (en) * | 2007-09-13 | 2009-03-19 | Basf Se | Flame retardant combinations of hydroxyalkyl phosphine oxides with 1,3,5-triazines and epoxides |
| JP5031681B2 (ja) * | 2008-06-23 | 2012-09-19 | キヤノン株式会社 | インクジェット用記録媒体 |
| US20110065838A1 (en) | 2009-09-11 | 2011-03-17 | Chemtura Corporation | Hydroxyphenyl Phosphine Oxide Mixtures and their use as Flame Retardants for Epoxy Resins |
| US20110065870A1 (en) | 2009-09-11 | 2011-03-17 | Chemtura Corporation | Tris(Hydroxoxyphenyl) Phosphine Oxides and their Use as Flame Retardants for Epoxy Resins |
| JP6113969B2 (ja) * | 2012-07-04 | 2017-04-12 | 帝人フィルムソリューション株式会社 | 難燃性ポリエステルフィルム |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2916473A (en) * | 1955-06-17 | 1959-12-08 | Austin L Bullock | Methylol-phosphorus modified epoxy resins |
| US3008926A (en) * | 1958-02-14 | 1961-11-14 | Hoechst Ag | Non-combustible, phosphorus-containing condensation resins and process for their manufacture |
| US3258492A (en) * | 1960-12-06 | 1966-06-28 | Melpar Inc | P-chloro or hydroxy benzyl tertiary phosphine oxides |
| NL289936A (enExample) * | 1962-03-07 | |||
| US3267149A (en) * | 1962-07-13 | 1966-08-16 | Monsanto Res Corp | 4-hydroxybutyl phosphorus compounds |
| US3716580A (en) * | 1968-12-17 | 1973-02-13 | Monsanto Co | Functional tertiary phosphine oxides |
| US3666543A (en) * | 1969-11-24 | 1972-05-30 | Ludwig Maier | Tris-(2-hydroxyalkyl)-phosphine oxide flame retardant articles |
| US3661857A (en) * | 1970-04-13 | 1972-05-09 | Monsanto Co | Polymeric compositions |
| US3645919A (en) * | 1970-10-20 | 1972-02-29 | Monsanto Co | Copolymers from phosphine oxide anhydrides |
| US3925265A (en) * | 1970-11-12 | 1975-12-09 | Hooker Chemicals Plastics Corp | Methyl phosphine oxides as flame retardants for organic polymers |
| US3948980A (en) * | 1970-12-30 | 1976-04-06 | Hoechst Aktiengesellschaft | Tertiary phosphine |
| US3981832A (en) * | 1971-02-11 | 1976-09-21 | Fokker-V.F.W. B.V. | Fire-protecting epoxy resins |
| US4151229A (en) * | 1973-11-14 | 1979-04-24 | Ciba-Geigy Corporation | Process for the manufacture of aminoalkyl-phosponic acid esters |
| CH582195A5 (enExample) | 1973-12-03 | 1976-11-30 | Ciba Geigy Ag | |
| US3888942A (en) * | 1973-12-13 | 1975-06-10 | Gen Electric | Resinous compositions and laminates made therefrom |
| DE2538675A1 (de) | 1975-08-30 | 1977-03-03 | Hoechst Ag | Verfahren zur herstellung von phosphorhaltigen epoxidharzen und ihre verwendung zur flammfestausruestung |
| ZA782445B (en) | 1977-04-30 | 1979-04-25 | Ciba Geigy Ag | Crosslinked epoxide resin compositions having flame retardant properties |
-
1981
- 1981-05-18 US US06/264,256 patent/US4345059A/en not_active Expired - Lifetime
-
1982
- 1982-04-27 CA CA000401754A patent/CA1184699A/en not_active Expired
- 1982-05-14 AR AR289400A patent/AR228093A1/es active
- 1982-05-14 NO NO821628A patent/NO821628L/no unknown
- 1982-05-17 EP EP82104311A patent/EP0066171B1/en not_active Expired
- 1982-05-17 JP JP57081678A patent/JPS6036212B2/ja not_active Expired
- 1982-05-17 AU AU83768/82A patent/AU552464B2/en not_active Ceased
- 1982-05-17 BR BR8202845A patent/BR8202845A/pt unknown
- 1982-05-17 AT AT82104311T patent/ATE21409T1/de not_active IP Right Cessation
- 1982-05-17 ES ES512269A patent/ES512269A0/es active Granted
- 1982-05-17 DE DE8282104311T patent/DE3272549D1/de not_active Expired
- 1982-05-18 KR KR8202172A patent/KR860000214B1/ko not_active Expired
- 1982-05-18 ZA ZA823441A patent/ZA823441B/xx unknown
-
1985
- 1985-01-16 JP JP60004192A patent/JPS60166457A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0066171A1 (en) | 1982-12-08 |
| ATE21409T1 (de) | 1986-08-15 |
| CA1184699A (en) | 1985-03-26 |
| JPS6119435B2 (enExample) | 1986-05-17 |
| AR228093A1 (es) | 1983-01-14 |
| EP0066171B1 (en) | 1986-08-13 |
| KR830010162A (ko) | 1983-12-26 |
| AU8376882A (en) | 1982-11-25 |
| ZA823441B (en) | 1983-03-30 |
| US4345059A (en) | 1982-08-17 |
| JPS60166457A (ja) | 1985-08-29 |
| NO821628L (no) | 1982-11-19 |
| KR860000214B1 (ko) | 1986-03-15 |
| JPS57195141A (en) | 1982-11-30 |
| AU552464B2 (en) | 1986-06-05 |
| ES8307012A1 (es) | 1983-06-16 |
| DE3272549D1 (en) | 1986-09-18 |
| BR8202845A (pt) | 1983-04-26 |
| ES512269A0 (es) | 1983-06-16 |
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