WO2015049965A1 - 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 - Google Patents
含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 Download PDFInfo
- Publication number
- WO2015049965A1 WO2015049965A1 PCT/JP2014/073994 JP2014073994W WO2015049965A1 WO 2015049965 A1 WO2015049965 A1 WO 2015049965A1 JP 2014073994 W JP2014073994 W JP 2014073994W WO 2015049965 A1 WO2015049965 A1 WO 2015049965A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- phosphorus
- containing compound
- epoxy resin
- alkyl group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 53
- 239000011574 phosphorus Substances 0.000 title claims abstract description 53
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 38
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 230000007246 mechanism Effects 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract description 7
- 230000009257 reactivity Effects 0.000 abstract description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 3
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- -1 phosphorus compound Chemical class 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
- 229960001755 resorcinol Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 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 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 2
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 2
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 2
- PEHXKUVLLWGBJS-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1O PEHXKUVLLWGBJS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 2
- OXRFNJSKALBWCF-UHFFFAOYSA-N 4-[4,4-bis(4-hydroxyphenyl)butan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 OXRFNJSKALBWCF-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBWIAVHZEWSRJI-UHFFFAOYSA-N Cl.Cl.OP(O)(=O)OC1=CC=CC=C1 Chemical compound Cl.Cl.OP(O)(=O)OC1=CC=CC=C1 XBWIAVHZEWSRJI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- JHHMSRLTZAUMOJ-UHFFFAOYSA-N methanamine;oxolane Chemical compound NC.C1CCOC1 JHHMSRLTZAUMOJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
- HIZADXNOHHWORN-UHFFFAOYSA-N 1-[(2-methylimidazol-1-yl)methyl]naphthalen-2-ol Chemical compound CC1=NC=CN1CC1=C(O)C=CC2=CC=CC=C12 HIZADXNOHHWORN-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VRRDONHGWVSGFH-UHFFFAOYSA-N 2,5-diethylcyclohexane-1,4-diamine Chemical compound CCC1CC(N)C(CC)CC1N VRRDONHGWVSGFH-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- VEGUCZXWLYWJFN-UHFFFAOYSA-N 3-[(3-hydroxy-2-methylphenyl)methyl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1CC1=CC=CC(O)=C1C VEGUCZXWLYWJFN-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-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
- 239000004566 building material Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000011083 cement mortar Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- QFUVJRPYJHRPSB-UHFFFAOYSA-N cyclohexylmethyl 2-methylcyclohexane-1-carboxylate Chemical compound CC1CCCCC1C(=O)OCC2CCCCC2 QFUVJRPYJHRPSB-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XBIMXRVVZSNNGI-UHFFFAOYSA-N ethanamine;oxolane Chemical compound CCN.C1CCOC1 XBIMXRVVZSNNGI-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- WYLQARGYFXBZMD-UHFFFAOYSA-N n-[chloro(dimethylamino)phosphoryl]-n-methylmethanamine Chemical compound CN(C)P(Cl)(=O)N(C)C WYLQARGYFXBZMD-UHFFFAOYSA-N 0.000 description 1
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1488—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/44—Amides
- C08G59/446—Phosphoramides
Definitions
- the present invention relates to a phosphorus-containing compound, and in particular, includes a reactivity, and can be used to provide a curable epoxy resin composition that can be expected to have flame retardancy, a low dielectric constant, and the like when used in combination with an epoxy compound. It relates to phosphorus compounds.
- Bromine-based flame retardants have good flame retardancy but generate harmful hydrogen halide (hydrogen bromide) gas during combustion. Therefore, their use is being suppressed. Therefore, a composition in which a non-halogen flame retardant, for example, a nitrogen compound, a phosphorus compound, or an inorganic compound is blended with a normal epoxy resin has been developed.
- a non-halogen flame retardant for example, a nitrogen compound, a phosphorus compound, or an inorganic compound
- these flame retardant imparting additives have problems such as insufficient flame retardant effect, adversely affecting the curing of the epoxy resin, and reducing physical properties such as the glass transition temperature of the cured composition. is there.
- Patent Document 1 proposes to use a reactive phosphate ester compound.
- An object of the present invention is to provide a phosphorus-containing compound having reactivity with a glycidyl group, specifically, by having reactivity with a glycidyl group, flame retardancy, low dielectric constant and the like can be expected.
- the object is to provide a phosphorus-containing compound capable of providing a curable epoxy resin composition.
- a phosphorus-containing compound having a specific structure is a compound that can achieve the above object, and have reached the present invention.
- the present invention provides a phosphorus-containing compound represented by the following general formula (I).
- R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, an alkyl group or an aryl group
- R 5 represents an alkyl group
- X represents an oxygen atom or a sulfur atom
- Y represents an oxygen atom, a sulfur atom or ⁇ NR ′
- R ′ represents a hydrogen atom.
- the present invention also provides a reaction method characterized in that the phosphorus-containing compound reacts with an epoxy compound by the following reaction mechanism.
- R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, an alkyl group or an aryl group
- R 5 represents an alkyl group
- X represents an oxygen atom or a sulfur atom
- Y represents an oxygen atom, a sulfur atom or ⁇ NR ′
- R ′ represents a hydrogen atom.
- Ar represents an aromatic group.
- the present invention also provides an epoxy resin curing agent comprising the above phosphorus-containing compound.
- the present invention also provides a curable epoxy resin composition containing the above epoxy resin curing agent.
- the present invention it is possible to provide a phosphorus-containing compound having excellent reactivity with an epoxy resin. By blending this, it is expected that the epoxy resin has flame retardancy, a low dielectric constant, and the like.
- FIG. 1 is a diagram showing a 1 H-NMR chart of the phosphorus-containing compound (I-1) obtained in Example 1.
- FIG. 2 is a 31 P-NMR chart of the phosphorus-containing compound (I-1) obtained in Example 1.
- FIG. 3 is a view showing a GC-MS chart of the phosphorus-containing compound (I-1) obtained in Example 1.
- 4 is a diagram showing a 1 H-NMR chart of the phosphorus-containing compound (I-2) obtained in Example 2.
- FIG. FIG. 5 is a diagram showing a 31 P-NMR chart of the phosphorus-containing compound (I-2) obtained in Example 2.
- 6 is a view showing a GC-MS chart of the phosphorus-containing compound (I-2) obtained in Example 2.
- FIG. 7 is a diagram showing a 1 H-NMR chart of the phosphorus-containing compound (I-3) obtained in Example 3.
- FIG. 8 is a diagram showing a 31 P-NMR chart of the phosphorus-containing compound (I-3) obtained in Example 3.
- FIG. 9 is a view showing a GC-MS chart of the phosphorus-containing compound (I-3) obtained in Example 3.
- 10 is a view showing a 1 H-NMR chart of the phosphorus-containing compound (I-9) obtained in Example 4.
- FIG. FIG. 11 is a 31 P-NMR chart of the phosphorus-containing compound (I-9) obtained in Example 4.
- 12 is a view showing a 1 H-NMR chart of S4 obtained in Example 5.
- FIG. 13 is a view showing a 31 P-NMR chart of S4 obtained in Example 5.
- FIG. 14 is a GC-MS chart of S4 obtained in Example 5.
- FIG. 15 is a view showing a 1 H-NMR chart of S5 obtained in Example 6.
- FIG. 16 is a view showing a 31 P-NMR chart of S5 obtained in Example 6.
- FIG. 17 is a view showing a GC-MS chart of S5 obtained in Example 6.
- the phosphorus-containing compound of the present invention is a novel compound represented by the general formula (I), and has a group having reactivity with a glycidyl group in its structure.
- examples of the alkyl group represented by R ′ include a methyl group, an ethyl group, a propyl group, and isopropyl.
- examples of the alkyl group represented by R ′ include a methyl group, an ethyl group, a propyl group, and isopropyl.
- Examples thereof include an alkyl group having 1 to 10 carbon atoms.
- R 1 , R 2 , R 3 , R 4 and Y are ⁇ NR ′
- examples of the aryl group represented by R ′ include a phenyl group and a naphthyl group.
- an aryl group having 1 to 5 carbon atoms is preferred as R 1 , R 2 , R 3 and R 4 .
- Examples of the alkyl group represented by R 5 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tertiary butyl group, an amyl group, an isoamyl group, a tertiary amyl group, a hexyl group, Examples include an isohexyl group, an octyl group, a 2-ethylhexyl group, a tertiary octyl group, a nonyl group, an alkyl group having 1 to 10 carbon atoms of a decyl group, and the alkanediyl group represented by R 5 includes, for example, a methylene group , An alkanediyl group having 1 to 10 carbon atoms such as an ethylene group, a propylene group, a butylene group and an octylene group.
- alkanetriyl group represented by R 3 examples include methylenetriyl, 1,1, Examples include alkanetriyl groups having 1 to 6 carbon atoms such as 3-ethylenetriyl group. Examples of alkanetetrayl groups include 1,1,2,2-ethylenetriyl groups. The include alkanetriyl group having 2 to 6 carbon atoms.
- Examples of the aromatic group represented by R 5 include mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F), methylene bis (orthocresol) ), Ethylidene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1,4-bis (4-hydroxyc) Milbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane, thiobisphenol, sulfonylbisphenol, oxybisphenol
- Examples thereof include polynuclear polyphenol compounds such as phenol novolak, orthocresol novolak, ethylphenol novol
- Examples of the phosphorus-containing compound of the present invention include compounds represented by the following formulas (I-1) to (I-9).
- R 1 , R 2 , R 3 and R 4 in the general formula (I) are independent of each other from the viewpoint of the phosphorus content in the phosphorus-containing compound and the availability of raw materials.
- Particularly preferred are compounds in which R 1 represents an alkyl group having 1 to 5 carbon atoms, R 5 represents an aromatic group represented by the above formulas (1) to (9), and X and Y represent oxygen atoms.
- the method for producing the phosphorus-containing compound of the present invention can be produced by a method such as the following formula (A) or formula (B).
- a method such as the following formula (A) or formula (B).
- R 1 to R 5 , X and Y have the same meaning as in the general formula (I).
- R 1 to R 5 , X and Y have the same meaning as in the general formula (I).
- Examples of the base used herein include tertiary amines such as triethylamine, tributylamine, diazabicycloundecene, diazabicyclononene, 1,4-diazabicyclo [2.2.2] octane, pyridine, N Pyridines such as N-dimethylaminopyridine, imidazoles such as 1-methylimidazole, phosphines such as triphenylphosphine, tributylphosphine, and tricyclohexylphosphine.
- tertiary amines such as triethylamine, tributylamine, diazabicycloundecene, diazabicyclononene, 1,4-diazabicyclo [2.2.2] octane
- pyridine N Pyridines such as N-dimethylaminopyridine, imidazoles such as 1-methylimidazole, phosphines
- Examples of the solvent (solv) used here include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, propylene glycol monomethyl ether acetate, and cyclohexanone; tetrahydrofuran, 1,2-dimethoxyethane, Ethers such as 1,2-diethoxyethane and propylene glycol monomethyl ether; esters such as ethyl acetate and n-butyl acetate; aromatic hydrocarbons such as benzene, toluene and xylene; carbon tetrachloride, chloroform, trichloroethylene, And halogenated aliphatic hydrocarbons such as methylene chloride; halogenated aromatic hydrocarbons such as chlorobenzene.
- ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl
- the phosphorus-containing compound of the present invention reacts efficiently with an epoxy compound (epoxy resin) by the following reaction mechanism, it can be preferably used as an epoxy resin curing agent.
- R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, an alkyl group or an aryl group
- R 5 represents an alkyl group
- X represents an oxygen atom or a sulfur atom
- Y represents an oxygen atom, a sulfur atom or ⁇ NR ′
- R ′ represents a hydrogen atom.
- Ar represents an aromatic group.
- examples of the aromatic group represented by Ar include the aryl group represented by R 1 and the like, the groups exemplified as the aromatic group represented by R 5 in the description of the general formula (I), and the like. Is mentioned.
- the epoxy resin curing agent of the present invention only needs to contain at least one phosphorus-containing compound of the present invention, and can be used alone or in combination.
- a known epoxy resin curing agent can be used.
- curing agent the general purpose epoxy resin hardening
- the content of the phosphorus-containing compound of the present invention is preferably 5 to 100% by mass, more preferably 20 to 100% by mass.
- the curable epoxy resin composition of the present invention is a combination of an epoxy resin curing agent containing the phosphorus-containing compound of the present invention and an epoxy compound (epoxy resin).
- Examples of the epoxy compound used in the curable epoxy resin composition of the present invention include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, Methylene bisphenol (bisphenol F), methylene bis (orthocresol), ethylidene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene) 1,4-bis (4-hydroxycumylbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as thiobisphenol, sulfonylbisphenol, oxy
- heterocyclic compounds such as conjugated diene polymers and triglycidyl isocyanurate.
- These epoxy compounds may be those internally crosslinked by a prepolymer of a terminal isocyanate or those having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). .
- the epoxy compound is preferably one having an epoxy equivalent of 70 to 3000, and more preferably 90 to 2000. If the epoxy equivalent is less than 70, the physical properties of the cured product may be lowered, and if it is greater than 3000, sufficient curability may not be obtained.
- the amount of the epoxy resin curing agent comprising the phosphorus-containing compound of the present invention and the amount of the epoxy compound used is preferably an epoxy compound relative to 1 equivalent of the phosphorus-containing compound of the present invention. 0.1 to 5 equivalents, more preferably 1 to 3 equivalents.
- a curing catalyst As such a curable catalyst, p-dimethylaminopyridine, triphenylphosphine, imidazole, tertiary amine, phosphine, quaternary ammonium salt, and quaternary phosphonium salt are used.
- a general-purpose epoxy resin curing agent can be used for the curable epoxy resin composition of the present invention.
- the epoxy resin curing agent include imidazoles such as 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 1- (2-methylimidazol-1-ylmethyl) naphthalen-2-ol; diethylenetriamine, Polyalkylpolyamines such as triethylenetriamine and tetraethylenepentamine; alicyclic polyamines such as 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane and isophoronediamine; m-xylylenediamine And aromatic polyamines such as diaminodiphenylmethane and diaminodiphenylsulfone.
- polyamines and glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, bisphenol F-diglycidyl ether, or various epoxy resins such as glycidyl esters of carboxylic acid are used in a conventional manner.
- a polyepoxy addition modification product produced by reacting with a carboxylic acid such as phthalic acid, isophthalic acid, dimer acid, etc.
- polyamines and aldehydes such as formaldehyde and phenols having at least one aldehyde-reactive site in the nucleus such as phenol, cresol, xylenol, tert-butylphenol, and resorcin are prepared by a conventional method. Mannich-modified products, etc. which is produced by response and the like. Furthermore, latent curing agents such as dicyandiamide, acid anhydrides, and imidazoles can also be used.
- the curable epoxy resin composition of the present invention includes a reactive or non-reactive diluent (plasticizer) such as monoglycidyl ethers, dioctyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar and the like, if necessary.
- a reactive or non-reactive diluent such as monoglycidyl ethers, dioctyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar and the like, if necessary.
- Fillers such as glass fiber, carbon fiber, cellulose, silica sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, fine powder silica, titanium dioxide, carbon black, graphite, iron oxide, and bitumen Pigment: ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) -N′- ⁇ - (aminoethyl) - ⁇ -aminopropyl Triethoxysilane, ⁇ -anilinopropyltriethoxysilane, ⁇ -glycidoxy Propyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, vinyltriethoxysilane, N- ⁇ - (N-vinylbenzy
- the curable epoxy resin composition of the present invention includes, for example, paints or adhesives for concrete, cement mortar, various metals, leather, glass, rubber, plastic, wood, cloth, paper, etc .; packaging adhesive tape, adhesive label, frozen Food labels, removable labels, POS labels, adhesive wallpaper, adhesives for adhesive flooring; art paper, lightweight coated paper, cast coated paper, coated paperboard, carbonless copiers, impregnated paper and other processed paper; natural fiber, synthetic Fiber treatment agents such as fibers, glass fibers, carbon fibers, metal fibers, etc., fiber treatment agents such as fraying prevention agents and processing agents; building materials such as sealing materials, cement admixtures and waterproofing materials; sealants for electronic and electrical equipment, etc. It can be used for a wide range of applications.
- the aerobic layer was washed with 10 mL of water, dried over anhydrous magnesium sulfate, and the solvent was removed with an evaporator to obtain a pale yellow liquid (crude yield 93.3%, GC purity 70.5%).
- the identification results are shown in FIG. 1 ( 1 H-NMR), FIG. 2 ( 31 P-NMR) and FIG. 3 (GC-MS).
- Example 5 According to the following reaction formula, 57.1 mg (0.25 mmol) of the phosphorus-containing compound [I-2] obtained in Example 2 and 51.6 mg of Adekaglycilol ED-509S (in the presence of 2.3 mg (7.5 mol%) of DMPA catalyst ( 0.25 mmol) was reacted at 140 ° C. for 2 hours under a nitrogen stream. From 1 H-NMR (FIG. 12), 31 P-NMR (FIG. 13) and GC-MS (FIG. 14), it was confirmed that S4 was obtained as the main product.
- Example 6 According to the following reaction formula, 50.0 mg (0.25 mmol) of the phosphorus-containing compound [I-3] obtained in Example 3 and 51.6 mg of Adekaglycilol ED-509S (in the presence of 2.3 mg (7.5 mol%) of DMPA catalyst 0.25 mmol) was reacted at 130 ° C. for 2 hours under a nitrogen stream. From 1 H-NMR (FIG. 15), 31 P-NMR (FIG. 16) and GC-MS (FIG. 17), it was confirmed that S5 was obtained as the main product.
- Example 7 Adeka Resin EP-4100L 1.02 g (100.0 phr.), The phosphorus-containing compound [I-9] of the present invention 0.16 g (15.7 phr.) And 2-ethyl-4-methylimidazole 0.03 g (3.0 phr.) Were mixed, Heating at 150 ° C. for 3 hours in a thermostatic bath, followed by heating at 180 ° C. for 3 hours, a brown cured product having no tack was obtained. It was 140 degreeC when Tg of this hardened
- the phosphorus-containing compound of the present invention has reactivity with a glycidyl group.
- the phosphoric acid ester of the present invention By blending the phosphoric acid ester of the present invention into the epoxy resin composition, it is possible to provide a cured epoxy resin that can be expected to have a flame retardancy and a low dielectric constant by suppressing a decrease in physical properties of the cured product. .
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
Abstract
Description
しかし、これらの難燃剤で充分な難燃性を付与するには多量に配合する必要があり、多量に配合して難燃性を満足すると、ガラス転移温度が低下し、逆に、ガラス転移温度を高くするために、難燃剤の配合量を少量にすると、難燃性が不足する。また、特許文献2には、反応性のリン酸エステル化合物を用いることが提案されているが、リン酸エステルが樹脂中に組み込まれると吸湿し易くなったり、一部が3次元構造になってエポキシ樹脂の粘度が増大し、作業性が大きく低下したりするため、実用的ではなかった。
本発明の含リン化合物は、一般式(I)で表される新規化合物であり、その構造中に、グリシジル基との反応性を有する基を有する。
R5で表されるアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、第三ブチル基、アミル基、イソアミル基、第三アミル基、ヘキシル基、イソヘキシル基、オクチル基、2-エチルヘキシル基、第三オクチル基、ノニル基、デシル基の炭素数1~10のアルキル基等が挙げられ、R5で表されるアルカンジイル基としては、例えばメチレン基、エチレン基、プロピレン基、ブチレン基、オクチレン基等の炭素数1~10のアルカンジイル基が挙げられ、R3で表されるアルカントリイル基としては、例えば、メチレントリイル、1,1,3-エチレントリイル基等の炭素数1~6のアルカントリイル基が挙げられ、アルカンテトライル基としては、1,1,2,2-エチレントリイル等の炭素数2~6のアルカントリイル基が挙げられる。
R5で表される芳香族基としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノール等の単核多価フェノール化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(ビスフェノールA)、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3-ビス(4-ヒドロキシクミルベンゼン)、1,4-ビス(4-ヒドロキシクミルベンゼン)、1,1,3-トリス(4-ヒドロキシフェニル)ブタン、1,1,2,2-テトラ(4-ヒドロキシフェニル)エタン、チオビスフェノール、スルホニルビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物等が挙げられ、中でも下記式(1)~(9)で表される基が好ましい。
回転子、還流管及びセプタムを備えた100mL三口フラスコに、4-メチルアミノピリジン(DMAP)0.1g(1mmol)を仕込んだ。十分に乾燥、窒素置換し、シリンジでフェノール0.9g(10mmol)、超脱水テトラヒドロフラン10mLを仕込んだ。ビス(ジメチルアミノ)ホスホリルクロリド2.0g(12mmol)を反応温度が30℃を超えないようにシリンジで滴下した。滴下終了後、10分間攪拌し、トリエチルアミン1.2 g(12mmol)を反応温度が40℃を超えないようにシリンジで滴下した。滴下終了後、一晩攪拌した。反応溶液に、飽和アンモニウムクロリド水溶液5mL及び水5mLを加え良く攪拌した。反応溶液を分液漏斗に移し、ジエチルエーテル10mLで3回抽出し、有気層を得た。有気層を水10mLで洗浄、無水硫酸マグネシウムで乾燥、エバポレーターで溶媒を除去し、淡黄色液体を得た(粗収率93.3%、GC純度70.5%)。粗生成物をカラムクロマトグラフィー(固定相:シリカゲル、移動相:酢酸エチル(2vol)/ヘキサン(1vol)、Rf=0.20)で精製することで、目的の含リン化合物〔I-1〕を得た(無色液体、総収率:44.0%、GC純度:>99%、31P-NMR:15.94ppm)。同定結果を図1(1H-NMR)、図2(31P-NMR)及び図3(GC-MS)に示す。
回転子、還流管及びセプタムを備えた100mL三口フラスコを十分に乾燥、窒素置換した。食塩/氷水バスで冷却しながら、エチルアミンテトラヒドロフラン溶液 9.5g(21mmol)、トリエチルアミン2.1g(21mmol)及び超脱水テトラヒドロフラン5mLを仕込んだ。5分間攪拌した後、リン酸フェニルジクロリド2.1g(10mmol)を反応温度が0℃を超えないようにシリンジで滴下した。滴下終了後、さらに1時間攪拌した。食塩/氷水バスを除去し、室温で一晩攪拌した。反応溶液に飽和アンモニウムクロリド水溶液5mL、水 5mLを加え良く攪拌した。溶液を分液漏斗に移し、酢酸エチル10mLで3回抽出し、有気層を得た。有気層を水10mLで洗浄、無水硫酸マグネシウムで乾燥、エバポレーターで溶媒を除去し、淡黄色液体を得た(粗収率92.9%、GC純度98.5%)。粗生成物をカラムクロマトグラフィー(固定相:シリカゲル、移動相:酢酸エチル、Rf=0.23)で精製することで目的の含リン化合物〔I-2〕を得た(無色液体、総収率:73.8%、GC純度:>99%、31P-NMR:12.01ppm)。同定結果を図4(1H-NMR)、図5(31P-NMR)及び図6(GC-MS)に示す。
回転子、還流管及びセプタムを備えた100mL三口フラスコを十分に乾燥、窒素置換した。食塩/氷水バスで冷却しながら、メチルアミンテトラヒドロフラン溶液 9.0g(21mmol)トリエチルアミン2.1g(21mmol)及び超脱水テトラヒドロフラン5mLを仕込んだ。5分間攪拌した後、リン酸フェニルジクロリド2.1g(10mmol)を反応温度が0℃を超えないようにシリンジで滴下した。滴下終了後、さらに1時間攪拌した。食塩/氷水バスを除去し、室 温で一晩攪拌した。反応溶液にアセトン10mLを加え良く攪拌し、濾過で固形分と濾液に分離した。得られた固形分にアセトン10mLを加え良く攪拌し、再度固形分と濾液に分離した。同様の手順で固形分を再度アセトンで洗浄した。全ての濾液を回収し、エバポレーターで溶媒を除去し、淡黄色結晶を得た(粗収率110.3%、GC純度95.5%)。粗生成物をカラムクロマトグラフィー(固定相:シリカゲル、移動相:酢酸エチル(6vol)/メタノール(1vol)、Rf=0.46)することで目的の含リン化合物〔I-3〕を得た(白色結晶、総収率:56.5%、GC純度:97.4%、31P-NMR:15.27ppm)。同定結果を図7(1H-NMR)、図8(31P-NMR)及び図9(GC-MS)に示す。
回転子、還流管及びN2導入口を備えた30 mL二口フラスコに、塩化マグネシウム0.03g(0.3 mmol)、4,4'-メチレンジフェノール2.00 g( 10 mmol)及びオキシ塩化リン30.67 g(200mmol)を仕込んだ。N2を導入しながら反応溶液が還流するまで加熱し、そのままの温度で一晩撹拌した。導入したN2は還流管上部より排気し、排気は全て水酸化ナトリウム水溶液にバブリングさせ、反応で発生する塩化水素をトラップした。反応後、エバポレーターで過剰量のオキシ塩化リンを除去し、黄色の液体を得た(中間体)。得られた中間体は脱水テトラヒドロフラン10mLで溶解し、中間体のTHF溶液を調製した。次に、回転子、還流管及びセプタムを備えた100 mL三口フラスコを十分に乾燥、窒素置換した。食塩/氷水バスで冷却しながら、メチルアミンテトラヒドロフラン溶液18.08 g(42 mmol)、トリエチルアミン4.25 g(42 mmol)を仕込んだ。5分間撹拌した後、中間体のTHF溶液を反応温度が20℃を超えないようにシリンジで滴下した。滴下終了後、さらに1時間撹拌した。食塩/氷水バスを除去し、室温で一晩撹拌した。反応後、エバポレーターで溶媒及び過剰量の原料を除去し、淡黄 色固体を得た。粗生成物をカラムクロマトグラフィー(固定相:シリカゲル、移動相:酢酸エチル(5 vol.)/メタノール(1 vol.)、Rf=0.29)することで目的の含リン化合物[I-9]を得た(白色固体、総収率:35.2%)。同定結果を図10(1H-NMR)及び図11(31P-NMR)に示す。
下記反応式に従い、DMPA 2.3 mg(7.5mol%)触媒存在下、実施例2で得られた含リン化合物〔I-2〕57.1mg(0.25mmol)とアデカグリシロールED-509S 51.6mg(0.25mmol)を窒素気流下、140℃で2時間反応させた。1H-NMR(図12)、31P-NMR(図13)及びGC-MS(図14)から、S4が主生成物で得られることを確認した。
下記反応式に従い、DMPA 2.3 mg(7.5mol%)触媒存在下、実施例3で得られた含リン化合物〔I-3〕50.0mg(0.25mmol)とアデカグリシロールED-509S 51.6mg(0.25mmol)を窒素気流下、130℃で2時間反応させた。1H-NMR(図15)、31P-NMR(図16)及びGC-MS(図17)から、S5が主生成物で得られることを確認した。
アデカレジンEP-4100L 1.02 g(100.0 phr.)、本発明の含リン化合物[I-9] 0.16 g(15.7 phr.)及び2-エチル-4-メチルイミダゾール 0.03 g(3.0 phr.)を混合し、恒温槽で150℃で3 時間、続いて180℃で3 時間加熱しタックのない褐色の硬化物を得た。この硬化物のTgをDSCで調べたところ140℃であった。
Claims (6)
- 上記一般式(I)において、R1、R2、R3及びR4が互いに独立して炭素数1~5のアルキル基を表し、R5が上記式(1)~(9)で表される芳香族基を表し、X及びYが酸素原子を表すことを特徴とする請求項1又は2記載の含リン化合物。
- 請求項1~3の何れか1項に記載の含リン化合物を含有してなるエポキシ樹脂硬化剤。
- 請求項5に記載のエポキシ樹脂硬化剤を含有してなる硬化性エポキシ樹脂組成物。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112016005231-5A BR112016005231B1 (pt) | 2013-10-01 | 2014-09-10 | Composto contendo fósforo, processo, agente de cura de resina epóxi, e, composição de resina epóxi curável |
CN201480049257.4A CN105764910A (zh) | 2013-10-01 | 2014-09-10 | 含磷化合物以及含有该化合物的固化性环氧树脂组合物 |
EP14850484.8A EP3053928A4 (en) | 2013-10-01 | 2014-09-10 | Phosphorus-containing compound, and curable epoxy resin composition containing same |
JP2015540441A JP6499968B2 (ja) | 2013-10-01 | 2014-09-10 | 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 |
KR1020167005774A KR102320939B1 (ko) | 2013-10-01 | 2014-09-10 | 인 함유 화합물 및 그것을 함유하는 경화성 에폭시 수지 조성물 |
US14/915,766 US9738667B2 (en) | 2013-10-01 | 2014-11-10 | Phosphorus-containing compound and curing epoxy resin composition containing same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013-206637 | 2013-10-01 | ||
JP2013206637 | 2013-10-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015049965A1 true WO2015049965A1 (ja) | 2015-04-09 |
Family
ID=52778561
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2014/073994 WO2015049965A1 (ja) | 2013-10-01 | 2014-09-10 | 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US9738667B2 (ja) |
EP (1) | EP3053928A4 (ja) |
JP (1) | JP6499968B2 (ja) |
KR (1) | KR102320939B1 (ja) |
CN (2) | CN105764910A (ja) |
BR (1) | BR112016005231B1 (ja) |
TW (1) | TWI623547B (ja) |
WO (1) | WO2015049965A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016152839A1 (ja) * | 2015-03-23 | 2016-09-29 | 株式会社Adeka | エポキシ樹脂組成物 |
JP2019038988A (ja) * | 2017-08-23 | 2019-03-14 | 株式会社Adeka | 難燃性エポキシ樹脂組成物 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3531550A (en) * | 1965-08-12 | 1970-09-29 | Monsanto Co | Phosphorus ester amides |
GB1333276A (en) * | 1970-08-17 | 1973-10-10 | Monsanto Co | Functional fluid compositions |
JPS5082150A (ja) * | 1973-11-21 | 1975-07-03 | ||
GB1494774A (en) * | 1974-02-12 | 1977-12-14 | Fahlberg List Veb | Animal fodder |
JPH08337709A (ja) | 1995-04-10 | 1996-12-24 | Shin Etsu Chem Co Ltd | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
JPH10195178A (ja) | 1997-01-06 | 1998-07-28 | Toshiba Chem Corp | 難燃性エポキシ樹脂組成物、プリプレグ、積層板、銅張積層板及びプリント配線板 |
JPH10265487A (ja) * | 1997-03-21 | 1998-10-06 | Kanagawa Univ | ホスホン酸エステル類並びにポリホスホネートの 製造方法と硬化性組成物 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1333276A (en) * | 1919-10-25 | 1920-03-09 | Thomas E Murray | Seal-fastening |
US1494774A (en) * | 1923-05-29 | 1924-05-20 | Eugene H Davis | Cake-cutting machine |
NL131206C (ja) * | 1965-09-03 | |||
US3475536A (en) * | 1967-06-01 | 1969-10-28 | Dow Chemical Co | Method for the systemic control of ectoparasites with phosphorodiamidates |
US3645971A (en) * | 1969-03-10 | 1972-02-29 | Hooker Chemical Corp | Fire retardant epoxy resins containing phosphoramidates |
US3764374A (en) * | 1970-07-21 | 1973-10-09 | Eastman Kodak Co | Process for placing modifiers within polyester fibers and films |
JPS521592B2 (ja) * | 1972-07-31 | 1977-01-17 | ||
JPS5438649B2 (ja) * | 1972-11-28 | 1979-11-22 | ||
JPS5093949A (ja) * | 1973-12-24 | 1975-07-26 | ||
DE2505326A1 (de) * | 1974-02-18 | 1975-08-21 | Sandoz Ag | Flammfest ausgeruestete regenerierte cellulose |
US4062909A (en) * | 1974-04-08 | 1977-12-13 | Monsanto Company | Phosphoroamidates |
DE2417991A1 (de) * | 1974-04-11 | 1975-10-23 | Univ Moskovsk | Thiophosphorsaeureamide, verfahren zu deren herstellung und deren anwendung |
US4086302A (en) * | 1975-07-28 | 1978-04-25 | Monsanto Company | Phosphoroamidates |
US4518413A (en) * | 1983-06-06 | 1985-05-21 | Allied Corporation | Poly-phosphorodiamide urease inhibitors and urease inhibited urea based fertilizer compositions |
RU2175242C1 (ru) * | 2000-09-27 | 2001-10-27 | Московский НИИ глазных болезней имени Гельмгольца | Способ лечения увеальной меланомы |
CN102617637B (zh) * | 2012-02-23 | 2015-07-08 | 四川大学 | 以对苯二酚磷酸酯为骨架的有机磷氮系阻燃剂的制备方法 |
-
2014
- 2014-09-10 KR KR1020167005774A patent/KR102320939B1/ko active IP Right Grant
- 2014-09-10 CN CN201480049257.4A patent/CN105764910A/zh active Pending
- 2014-09-10 WO PCT/JP2014/073994 patent/WO2015049965A1/ja active Application Filing
- 2014-09-10 JP JP2015540441A patent/JP6499968B2/ja active Active
- 2014-09-10 EP EP14850484.8A patent/EP3053928A4/en not_active Withdrawn
- 2014-09-10 BR BR112016005231-5A patent/BR112016005231B1/pt active IP Right Grant
- 2014-09-10 CN CN202010926152.XA patent/CN112029073A/zh active Pending
- 2014-09-19 TW TW103132525A patent/TWI623547B/zh active
- 2014-11-10 US US14/915,766 patent/US9738667B2/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3531550A (en) * | 1965-08-12 | 1970-09-29 | Monsanto Co | Phosphorus ester amides |
GB1333276A (en) * | 1970-08-17 | 1973-10-10 | Monsanto Co | Functional fluid compositions |
JPS5082150A (ja) * | 1973-11-21 | 1975-07-03 | ||
GB1494774A (en) * | 1974-02-12 | 1977-12-14 | Fahlberg List Veb | Animal fodder |
JPH08337709A (ja) | 1995-04-10 | 1996-12-24 | Shin Etsu Chem Co Ltd | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
JPH10195178A (ja) | 1997-01-06 | 1998-07-28 | Toshiba Chem Corp | 難燃性エポキシ樹脂組成物、プリプレグ、積層板、銅張積層板及びプリント配線板 |
JPH10265487A (ja) * | 1997-03-21 | 1998-10-06 | Kanagawa Univ | ホスホン酸エステル類並びにポリホスホネートの 製造方法と硬化性組成物 |
Non-Patent Citations (5)
Title |
---|
BUINA, N. A. ET AL.: "Synthesis and addition reactions of arylphosphorus acid tetraethyldiamides", IZVESTIYA AKADEMII NAUK SSSR, 1967, pages 1606 - 8, XP008183140 * |
QUAST, HELMUT ET AL.: "Three-membered heterocycles. 10. Phosphonohydrazidic esters by alkoxide-induced rearrangement of N-chlorophosphonic diamides", LIEBIGS ANNALEN DER CHEMIE, vol. 5, 1981, pages 943 - 66, XP002970414 * |
ROTH, HERMANN J. ET AL.: "Synthesis of phenyl phosphorodiamidates. I", ARCHIV DER PHARMAZIE, vol. 314, no. 1, 1981, pages 85 - 91, XP008183191 * |
See also references of EP3053928A4 * |
SKROWACZEWSKA, ZOFIA ET AL.: "Action of hydrogen halides upon the P-N bond in some amide derivatives of phosphoric acid", ROCZNIKI CHEMII, vol. 29, 1955, pages 415 - 30, XP008182912 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016152839A1 (ja) * | 2015-03-23 | 2016-09-29 | 株式会社Adeka | エポキシ樹脂組成物 |
US10655005B2 (en) | 2015-03-23 | 2020-05-19 | Adeka Corporation | Epoxy resin composition |
JP2019038988A (ja) * | 2017-08-23 | 2019-03-14 | 株式会社Adeka | 難燃性エポキシ樹脂組成物 |
JP7066268B2 (ja) | 2017-08-23 | 2022-05-13 | 株式会社Adeka | 難燃性エポキシ樹脂組成物 |
Also Published As
Publication number | Publication date |
---|---|
BR112016005231B1 (pt) | 2021-04-13 |
KR102320939B1 (ko) | 2021-11-03 |
KR20160065814A (ko) | 2016-06-09 |
TW201518312A (zh) | 2015-05-16 |
EP3053928A4 (en) | 2017-03-01 |
CN112029073A (zh) | 2020-12-04 |
US20160200747A1 (en) | 2016-07-14 |
US9738667B2 (en) | 2017-08-22 |
EP3053928A1 (en) | 2016-08-10 |
TWI623547B (zh) | 2018-05-11 |
JPWO2015049965A1 (ja) | 2017-03-09 |
JP6499968B2 (ja) | 2019-04-10 |
CN105764910A (zh) | 2016-07-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5754731B2 (ja) | エポキシ樹脂、エポキシ樹脂の製造方法、及びその使用 | |
WO2010113784A1 (ja) | エポキシ樹脂、エポキシ樹脂組成物及び硬化物 | |
JP6161340B2 (ja) | ビスイミダゾール化合物、該ビスイミダゾール化合物を含有するエポキシ樹脂用硬化剤及び該エポキシ樹脂用硬化剤を含有する一液型硬化性エポキシ樹脂組成物 | |
JP6499968B2 (ja) | 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 | |
JP6618049B2 (ja) | 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 | |
JP5996977B2 (ja) | ポリチオウレタン化合物、該化合物を含有するエポキシ樹脂用硬化剤、及び、該エポキシ樹脂用硬化剤を含有してなる一液型硬化性エポキシ樹脂組成物 | |
JP6240940B2 (ja) | エポキシ樹脂組成物 | |
JP2013139527A (ja) | イソシアヌレート化合物 | |
JP2006022146A (ja) | 硬化性樹脂組成物 | |
JP2005097473A (ja) | 新規エポキシ化合物、その製造方法、硬化性エポキシ樹脂組成物およびその硬化体 | |
US7074946B2 (en) | Method of producing glycidyl 2-hydroxyisobutyrate | |
JP6307245B2 (ja) | エポキシ樹脂組成物 | |
JP2017031275A (ja) | 熱硬化性樹脂組成物の硬化方法および熱硬化性樹脂組成物 | |
JP4605855B2 (ja) | エポキシ樹脂組成物 | |
JP2006022153A (ja) | 硬化性樹脂組成物 | |
JP2006057013A (ja) | 樹脂組成物 | |
TW202144322A (zh) | 環氧胺加合物、硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14850484 Country of ref document: EP Kind code of ref document: A1 |
|
REEP | Request for entry into the european phase |
Ref document number: 2014850484 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14915766 Country of ref document: US Ref document number: 2014850484 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 20167005774 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2015540441 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112016005231 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112016005231 Country of ref document: BR Kind code of ref document: A2 Effective date: 20160309 |