TWI623546B - 含磷化合物及含有其之硬化性環氧樹脂組合物 - Google Patents
含磷化合物及含有其之硬化性環氧樹脂組合物 Download PDFInfo
- Publication number
- TWI623546B TWI623546B TW103128852A TW103128852A TWI623546B TW I623546 B TWI623546 B TW I623546B TW 103128852 A TW103128852 A TW 103128852A TW 103128852 A TW103128852 A TW 103128852A TW I623546 B TWI623546 B TW I623546B
- Authority
- TW
- Taiwan
- Prior art keywords
- phosphorus
- containing compound
- group
- alkyl group
- epoxy resin
- Prior art date
Links
- 229920000647 polyepoxide Polymers 0.000 title claims description 22
- 239000003822 epoxy resin Substances 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title claims description 11
- 150000003018 phosphorus compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 31
- 239000011574 phosphorus Substances 0.000 claims abstract description 31
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract description 5
- 230000009257 reactivity Effects 0.000 abstract description 4
- -1 phosphorus compound Chemical class 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 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 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 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 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 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
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 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 4
- 239000000243 solution Substances 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
- 239000001993 wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 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
- 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 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
- 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 2
- AWDVJPLMXAORRQ-UHFFFAOYSA-N 3-hydroxy-2-(2-hydroxyphenyl)benzenesulfonic acid Chemical compound S(=O)(=O)(O)C1=C(C(=CC=C1)O)C=1C(=CC=CC1)O AWDVJPLMXAORRQ-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 150000004945 aromatic hydrocarbons Chemical class 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
- 239000003054 catalyst Substances 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
- 238000007796 conventional method Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- 150000002118 epoxides Chemical class 0.000 description 2
- DEBBJJUTLAGABF-UHFFFAOYSA-N ethene;phenol Chemical compound C=C.OC1=CC=CC=C1.OC1=CC=CC=C1 DEBBJJUTLAGABF-UHFFFAOYSA-N 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
- 239000003365 glass fiber Substances 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
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 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
- 125000001624 naphthyl group Chemical group 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-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
- 239000012044 organic layer Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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
- 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
- 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
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical class CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-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
- ZUESTMNQCYNCPP-UHFFFAOYSA-N 3-[2-(3-hydroxy-2-methylphenyl)propan-2-yl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(C)(C)C1=CC=CC(O)=C1C ZUESTMNQCYNCPP-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
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical class C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- JPKVIAIUBLGJQH-UHFFFAOYSA-N 6-methylidenecyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CCC(=C)C1C(O)=O JPKVIAIUBLGJQH-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- BLJDJVLDTYVWCL-UHFFFAOYSA-N CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C Chemical compound CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C BLJDJVLDTYVWCL-UHFFFAOYSA-N 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
- 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
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 239000006004 Quartz sand Substances 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
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 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
- 125000001931 aliphatic group Chemical group 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001409 amidines Chemical class 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
- 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
- 230000015572 biosynthetic process Effects 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
- 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
- 239000004566 building material Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 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
- 238000000576 coating method Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- YPWYKIZLWMBFKH-UHFFFAOYSA-N diamino(diphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](N)(N)C1=CC=CC=C1 YPWYKIZLWMBFKH-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 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
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 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
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class 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
- 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 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
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 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
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 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
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- 239000012170 montan wax Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical class C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-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
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical class C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical group NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl 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])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 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
- 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
- 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
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 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
- 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
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 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
- 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
- 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
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3282—Esters with 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- 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
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Abstract
本發明提供一種具有與縮水甘油基之反應性之含磷化合物，具體而言，本發明提供一種下述通式(I)所表示之含磷化合物。
(式中，m表示1~10之數，R1、R2互相獨立，表示氫原子、烷基、芳基，R3表示烷基、烷二基、烷三基、烷四基、芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或-NR4-，R4表示氫原子、烷基、芳基)
Description
本發明係關於一種含磷化合物，詳細而言，係關於一種具有反應性、藉由與聚環氧化合物併用而可提供一種可期待阻燃化、低介電常數化等之硬化性環氧樹脂組合物之含磷化合物。
近年來，對世界性環境問題、對於人體之安全性之關心提高，同時對於電氣、電子製品，除了阻燃性，更少之有害性、更高之安全性之要求正增大。即，要求減少有害性氣體或冒煙之產生。
溴系阻燃劑雖然具有良好之阻燃性，但於燃燒時會產生有害之鹵化氫(溴化氫)氣體，故而其之使用正被抑制。因此，正開發有於通常之環氧樹脂中調配非鹵素系阻燃劑、例如氮化合物、磷化合物、或無機化合物等而成之組合物。然而，該等阻燃賦予性添加劑存在如下問題：阻燃化效果不充分，或對環氧樹脂之硬化造成不良影響，使硬化組合物之玻璃轉移溫度等物性降低等。
例如，作為磷系阻燃劑，而將磷酸三苯酯廣泛用於各種樹脂中，於專利文獻1中提出有將作為高分子量型之二酚與含有酚之磷系阻燃劑用於環氧樹脂。然而，為了藉由該等阻燃劑對環氧樹脂賦予充分之阻燃性，必須調配大量阻燃劑，若滿足阻燃性，則玻璃轉移溫度降低，若提高玻璃轉移溫度，則阻燃性不足。又，於專利文獻2中提出有使用反應性之磷酸酯化合物作為阻燃劑，但若於樹脂中混入磷酸酯，則樹脂變得容易吸濕，或部分成為三維結構，環氧樹脂之黏度增
大，作業性大幅降低，故而並不實用。
專利文獻1：US5739187(A)
專利文獻2：日本專利特開平10-195178號公報
本發明之目的在於：提供一種具有與縮水甘油基之反應性之含磷化合物；提供一種藉此可提供可期待阻燃化、低介電常數化等之硬化性環氧樹脂組合物之含磷化合物。
本發明者等人為了解決上述課題而進行銳意研究，結果發現一種特定之含磷化合物係可達成上述目的之化合物，從而達成本發明。
即，本發明提供一種下述通式(I)所表示之含磷化合物。
(式中，m表示1~10之數，R1、R2互相獨立，表示氫原子、烷基、芳基，R3表示烷基、烷二基、烷三基、烷四基、芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或-NR4-，R4表示氫原子、烷基、芳基)
藉由本發明，而提供一種與環氧樹脂之反應性優異之含磷化合
物，可期待環氧樹脂之阻燃化、低介電常數化等。
圖1係表示實施例1中獲得之含磷化合物之1H-NMR(nuclear magnetic resonance，核磁共振)的圖。
圖2係表示實施例1中獲得之含磷化合物之31P-NMR的圖。
圖3係表示實施例1中獲得之含磷化合物之GC-MS(gas chromatograph-mass spectrometry，氣相層析-質譜)的圖。
圖4係表示實施例2中獲得之P2之1H-NMR的圖。
圖5係表示實施例2中獲得之P2之31P-NMR的圖。
圖6係表示實施例2中獲得之P2之GC-MS的圖。
以下，對本發明之含磷化合物進行詳細說明。
通式(I)中，作為R1、R2所表示之烷基，例如可列舉：甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基、戊基、異戊基、第三戊基、己基、異己基、辛基、2-乙基己基、第三辛基、壬基、癸基等，作為R1、R2所表示之芳基，例如可列舉：苯基、萘基等，作為R3所表示之烷基，例如可列舉：甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基、戊基、異戊基、第三戊基、己基、異己基、辛基、2-乙基己基、第三辛基、壬基、癸基等，作為R3所表示之芳基，例如可列舉：苯基、萘基等，作為R3所表示之烷二基，例如可列舉：亞甲基、伸乙基、伸丙基、伸丁基、伸辛基等，作為R3所表示之烷三基，例如可列舉：亞甲基三基、1,1,3-伸乙基三基等，作為R3所表示之烷四基，可列舉1,1,2,2-伸乙基三基等。作為R3所表示之芳香族基，例如可列舉：對苯二酚、間苯二酚、鄰苯二酚、間苯三酚等單核多酚化合物；二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚
A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺醯基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物等，其中可較佳地使用下述式所表示之基。
作為本發明之含磷化合物，較佳為上述通式(I)中R1表示碳原子數1~5之烷基、R2表示碳原子數1~5之烷基、R3表示芳香族基、X及Y表示氧原子之含磷化合物。
作為本發明之含磷化合物，例如可列舉下述式(I-1)~(I-8)所表示之化合物。
[化8]
本發明之含磷化合物之製造方法可藉由如下述式所示之方法而製造。
(式中，m、R1、R2、R3、X、Y與上述之m、R1、R2、R3、X、Y相同)
作為此處所使用之鹼，例如可列舉：三乙胺、三丁胺、二氮雜雙環十一烯、二氮雜雙環壬烯、1,4-二氮雜雙環[2.2.2]辛烷等三級胺；吡啶、N,N-二甲胺基吡啶等吡啶類；1-甲基咪唑等咪唑類；三苯基膦、三丁基膦、三環己基膦等膦類等。
作為此處所使用之溶劑，例如可列舉：甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、丙二醇單甲醚乙酸酯、環己酮等酮類；四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇單甲醚等醚類；乙酸乙酯、乙酸正丁酯等酯類；苯、甲苯、二甲苯等芳香族烴；四氯化碳、氯仿、三氯乙烯、二氯甲烷等鹵化脂肪族烴；氯苯等鹵化芳香族烴等。
該等反應可於-80~100℃、較佳為室溫~50℃下花費0.5小時~72小時、較佳為1小時~24小時而實施。
又，本發明提供一種反應方法，其特徵在於上述含磷化合物利用下述反應機制而與環氧化合物反應。
(式中，m表示1~10之數，R1、R2互相獨立，表示氫原子、烷基、芳基，R3表示烷基、烷二基、烷三基、烷四基、芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或-NR4-，R4表示氫原子、烷基、芳基)
本發明之含磷化合物藉由與聚環氧化合物組合而提供硬化性環氧樹脂組合物。
作為用於本發明之聚環氧化合物，例如可列舉：對苯二酚、間苯二酚、鄰苯二酚、間苯三酚等單核多酚化合物之聚縮水甘油醚化合物；二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚
A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺醯基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物之聚縮水甘油醚化合物；乙二醇、丙二醇、丁二醇、己二醇、聚二醇、硫代二乙二醇、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇、雙酚A-環氧乙烷加成物等多元醇類之聚縮水甘油醚；順丁烯二酸、反丁烯二酸、伊康酸、丁二酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、均苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸、內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯類及甲基丙烯酸縮水甘油酯之均聚物或共聚物；N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺等具有縮水甘油基胺基之環氧化合物；乙烯基環己烯二環氧化物、二環戊二烯二環氧化物、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、3,4-環氧-6-甲基環己基甲基-6-甲基環己烷羧酸酯、雙(3,4-環氧-6-甲基環己基甲基)己二酸酯等環狀烯烴化合物之環氧化物；環氧化聚丁二烯、環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物；三縮水甘油基異氰尿酸酯等雜環化合物。又，該等環氧樹脂亦可為藉由末端異氰酸酯之預聚物而內部交聯者或藉由多元之活性氫化合物(多酚、多胺、含羰基之化合物、多磷酸酯等)而高分子量化者。
又，聚環氧化合物較佳為環氧當量為70~3000、進而較佳為90~2000者。若該環氧當量未達70，則有硬化物之物性降低之虞，於大於3000之情形時，有無法獲得充分之硬化性之虞，故而欠佳。
本發明之硬化性環氧樹脂組合物中較佳為使用硬化觸媒，可使
用對二甲胺基吡啶、三苯基膦、咪唑、三級胺、膦、四級銨鹽、四級鏻鹽。
本發明之硬化性環氧樹脂組合物中可使用通用之環氧樹脂硬化劑，作為該環氧樹脂硬化劑，例如可列舉：2-乙基-4-甲基咪唑、1,2-二甲基咪唑、1-(2-甲基咪唑-1-基甲基)萘-2-醇等咪唑類；二伸乙基三胺、三伸乙基三胺、四伸乙基五胺等聚烷基多胺類；1,2-二胺基環己烷、1,4-二胺基-3,6-二乙基環己烷、異佛爾酮二胺等脂環式多胺類；間苯二甲胺、二胺基二苯甲烷、二胺基二苯基碸等芳香族多胺類等。又，可列舉：藉由利用常規方法使該等多胺類與苯基縮水甘油醚、丁基縮水甘油醚、雙酚A-二縮水甘油醚、雙酚F-二縮水甘油醚等縮水甘油醚類或羧酸之縮水甘油酯類等各種環氧樹脂反應所製造之聚環氧加成改性物；藉由利用常規方法使該等有機多胺類與鄰苯二甲酸、間苯二甲酸、二聚酸等羧酸類反應所製造之醯胺化改性物；藉由利用常規方法使該等多胺類與甲醛等醛類及苯酚、甲酚、二甲苯酚、第三丁基苯酚、間苯二酚等核中至少具有一個醛化反應性部位之酚類反應所製造之曼尼希化改性物等。進而，亦可使用雙氰胺、酸酐、咪唑類等潛伏性硬化劑。
又，視需要亦可含有如下之常用添加物：單縮水甘油醚類、鄰苯二甲酸二辛酯、鄰苯二甲酸二丁酯、苄醇、煤焦油等反應性或非反應性之稀釋劑(塑化劑)；玻璃纖維、碳纖維、纖維素、石英砂、水泥、高嶺土、黏土、氫氧化鋁、膨潤土、滑石、二氧化矽、細粉末二氧化矽、二氧化鈦、碳黑、石墨、氧化鐵、瀝青物質等填充劑或顏料；γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-N'-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-苯胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三乙氧基矽烷、乙烯基三乙氧基矽烷、N-β-(N-
乙烯基苄基胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷等矽烷偶合劑；堪地里拉蠟、巴西棕櫚蠟、木蠟、蟲蠟、蜂蠟、羊毛脂、鯨蠟、褐煤蠟、石油蠟、脂肪酸蠟、脂肪酸酯、脂肪酸醚、芳香族酯、芳香族醚等潤滑劑；增黏劑；觸變劑；抗氧化劑；光穩定劑；紫外線吸收劑；阻燃劑；消泡劑；防銹劑；膠體二氧化矽、膠體氧化鋁等，進而，亦可併用二甲苯樹脂、石油樹脂等黏著性之樹脂類。
本發明之硬化性環氧樹脂組合物例如可用於如下之廣泛之用途：針對混凝土、水泥砂漿、各種金屬、皮革、玻璃、橡膠、塑膠、木、布、紙等之塗料或接著劑；包裝用膠帶、附著標籤、冷凍食品標籤、可移標籤、POS(point-of-sale)標籤、黏著壁紙、黏著地板材之黏著劑；銅版紙、輕量塗料紙、拋光塗料紙、塗佈紙板、無碳影印機、含浸紙等加工紙；天然纖維、合成纖維、玻璃纖維、碳纖維、金屬纖維等上漿劑、防散紗劑、加工劑等纖維處理劑；密封材、水泥混和劑、防水材等建築材料；電子電氣設備用密封劑等。
繼而，藉由實施例，進一步詳細說明本發明，但本發明並不受該等實施例任何限定。
將具備轉子、回流管、隔墊之100mL三口燒瓶充分乾燥並進行氮氣置換，利用注射器加入苯酚0.75g(8.8mmol)、三乙胺0.89g(8.8mmol)、超脫水四氫呋喃3mL。於另一容器中加入二甲基次膦醯氯0.90g(8mmol)、超脫水四氫呋喃3mL，製備二甲基次膦醯氯溶液。以反應溫度不超過30℃之方式利用注射器滴加所製備之二甲基次膦醯
氯溶液。滴加結束後，攪拌一晚。於反應溶液中加入飽和氯化銨水溶液5mL、水5mL並充分攪拌。將溶液轉移至分液漏斗中，利用乙酸乙酯10mL萃取3次而獲得有機層。利用水10mL洗淨有機層，並藉由無水硫酸鎂進行乾燥，利用蒸發器去除溶劑而獲得淡黃色液體。藉由管柱層析法(固定相：矽膠，流動相：乙酸乙酯，Rf=0.07)將粗產物(粗產率：60.3%，GC純度：87.1%)進行精製，從而獲得目標之含磷化合物[I-1](白色結晶，總產率：45.8%，GC純度：>99%，31P-NMR：52.44ppm)。分別將所獲得之含磷化合物之1H-NMR、31P-NMR及GC-MS示於圖1~3。
在DMAP(Dimethylaminopyridine，二甲胺基吡啶)0.9mg(7.5mol%)觸媒存在下，於氮氣氣流、160℃下使含磷化合物[I-1]17.0mg(0.25mmol)與ADEKA Glycilol ED-509S 20.6mg(0.25mmol)反應2小時。藉由下述之[化13]所示之反應機制而高選擇性地獲得[化13]所示之P2。將所獲得之P2之1H-NMR、31P-NMR及GC-MS分別示於圖4~6。
根據本發明之實施例，表示本發明之含磷化合物具有與縮水甘油基之反應性。藉由將本發明之磷酸酯調配於環氧樹脂組合物中，而可提供一種可期待抑制硬化物之物性降低，且具有阻燃性、低介電常數之環氧樹脂硬化物。
Claims (4)
- 一種含磷化合物，其係下述通式(I)所表示者，(式中，m表示1~4之數，R1、R2互相獨立，表示碳原子數1~5之烷基，R3表示以下述式表示之芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或-NR4-，R4表示氫原子、烷基、芳基)，
- 如請求項1之含磷化合物，其中於上述通式(I)中，X及Y表示氧原子。
- 一種反應方法，其特徵在於：如請求項1之含磷化合物係利用下述反應機制而與環氧化合物反應，(式中，m表示1~4之數，R1、R2互相獨立，表示碳原子數1~5之烷基，R3表示以下述式表示之芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或-NR4-，R4表示氫原子、烷基、芳基)，
- 一種硬化性環氧樹脂組合物，其係含有如請求項1之含磷化合物而成。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013171940 | 2013-08-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201512213A TW201512213A (zh) | 2015-04-01 |
| TWI623546B true TWI623546B (zh) | 2018-05-11 |
Family
ID=52483675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103128852A TWI623546B (zh) | 2013-08-22 | 2014-08-21 | 含磷化合物及含有其之硬化性環氧樹脂組合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10562924B2 (zh) |
| EP (1) | EP3037426B1 (zh) |
| JP (1) | JP6618049B2 (zh) |
| KR (1) | KR102301768B1 (zh) |
| CN (2) | CN111057104A (zh) |
| BR (1) | BR112016000802B1 (zh) |
| DK (1) | DK3037426T3 (zh) |
| ES (1) | ES2878126T3 (zh) |
| TW (1) | TWI623546B (zh) |
| WO (1) | WO2015025904A1 (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6666857B2 (ja) * | 2015-01-29 | 2020-03-18 | 株式会社Adeka | 難燃性エポキシ樹脂組成物、それを用いてなるプリプレグ及び積層板 |
| WO2020009001A1 (ja) * | 2018-07-04 | 2020-01-09 | 株式会社Adeka | 樹脂組成物、その硬化物、繊維強化プラスチック及び繊維強化プラスチックの難燃化方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121461A (en) * | 1964-07-28 | 1968-07-31 | Nippon Kokan Kk | Process of and apparatus for continuously annealing cold-rolled low-carbon steel |
| US3527850A (en) * | 1965-03-31 | 1970-09-08 | Monsanto Co | Phenyl dialkyl phosphinates |
| 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 |
| TW201002729A (en) * | 2008-03-28 | 2010-01-16 | Nippon Kayaku Kk | Aqueous dispersions of organic phosphorous compounds and flame retarding modification method using the dispersions |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE251134C (zh) | ||||
| NL259583A (zh) * | 1959-12-31 | |||
| GB991590A (en) * | 1963-08-01 | 1965-05-12 | Shell Res Ltd | Phosphinothionate insecticides |
| US3371046A (en) * | 1963-12-30 | 1968-02-27 | Douglas Aircraft Co Inc | Inhibition of corrosion of hydraulic fluids |
| DE1252680B (de) * | 1964-07-29 | 1967-10-26 | Monsanto Company, St. Louis, Mo. (V. St. A.) | Verfahren zur Herstellung von Phosphinsäureestern |
| DE1956187A1 (de) * | 1969-11-07 | 1971-05-13 | Vnii Fitopatologii | Als Fungizide anwendbare Organophosphorverbindungen und Verfahren zu deren Herstellung |
| DE2542009A1 (de) | 1975-09-20 | 1977-03-24 | Hoechst Ag | Bromhaltige phosphinsaeureester |
| SU584008A1 (ru) * | 1976-07-07 | 1977-12-15 | Казанский Химико-Технологический Институт Имени С.М.Кирова | Способ получени фениловых эфиров фосфиновых кислот |
| DD251134A1 (de) * | 1986-07-09 | 1987-11-04 | Univ Halle Wittenberg | Verfahren zur herstellung von organosilylmethylphosphinsaeureestern |
| EP0742261B1 (en) | 1995-04-10 | 2000-08-02 | Shin-Etsu Chemical Co., Ltd. | Semiconductor encapsulating epoxy resin compositions suitable for semiconductor encapsulation, their manufacture and use, semiconductor devices encapsulated therewith |
| 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 |
| WO2000017268A1 (en) | 1998-09-18 | 2000-03-30 | Albemarle Corporation | Halogen-free flame retardant thermoplastic polymer compositions |
| DE19917070A1 (de) | 1999-04-15 | 2000-10-19 | Basf Ag | Stabilisierte Phosphorverbindungen beinhaltende Zusammensetzung |
| KR20090073474A (ko) * | 2007-12-31 | 2009-07-03 | 제일모직주식회사 | 새로운 인계 난연제, 그 제조방법 및 이를 함유하는 난연열가소성 수지 조성물 |
| KR20090122819A (ko) * | 2008-05-26 | 2009-12-01 | 강원대학교산학협력단 | 분자내 하이드로아미네이션 반응용 신규 촉매와, 이 촉매를이용한 고리형 이민 화합물의 제조방법 |
| DE102008063640A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von gemischtsubstituierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
| KR101344792B1 (ko) * | 2010-12-17 | 2013-12-24 | 제일모직주식회사 | 하드마스크 조성물, 이를 사용한 패턴 형성 방법 및 상기 패턴을 포함하는 반도체 집적회로 디바이스 |
| WO2014206487A1 (en) * | 2013-06-28 | 2014-12-31 | Fundacion Imdea Materiales | A halogen free flame retardant epoxy resin composition |
-
2014
- 2014-08-21 WO PCT/JP2014/071825 patent/WO2015025904A1/ja active Application Filing
- 2014-08-21 DK DK14837177.6T patent/DK3037426T3/da active
- 2014-08-21 BR BR112016000802-2A patent/BR112016000802B1/pt active IP Right Grant
- 2014-08-21 TW TW103128852A patent/TWI623546B/zh active
- 2014-08-21 KR KR1020167002688A patent/KR102301768B1/ko active IP Right Grant
- 2014-08-21 CN CN201911290765.2A patent/CN111057104A/zh active Pending
- 2014-08-21 US US14/900,844 patent/US10562924B2/en active Active
- 2014-08-21 ES ES14837177T patent/ES2878126T3/es active Active
- 2014-08-21 CN CN201480043901.7A patent/CN105452263A/zh active Pending
- 2014-08-21 EP EP14837177.6A patent/EP3037426B1/en active Active
- 2014-08-21 JP JP2015532887A patent/JP6618049B2/ja active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121461A (en) * | 1964-07-28 | 1968-07-31 | Nippon Kokan Kk | Process of and apparatus for continuously annealing cold-rolled low-carbon steel |
| US3527850A (en) * | 1965-03-31 | 1970-09-08 | Monsanto Co | Phenyl dialkyl phosphinates |
| 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 |
| TW201002729A (en) * | 2008-03-28 | 2010-01-16 | Nippon Kayaku Kk | Aqueous dispersions of organic phosphorous compounds and flame retarding modification method using the dispersions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2015025904A1 (ja) | 2017-04-27 |
| US10562924B2 (en) | 2020-02-18 |
| EP3037426A4 (en) | 2017-05-03 |
| WO2015025904A1 (ja) | 2015-02-26 |
| TW201512213A (zh) | 2015-04-01 |
| EP3037426A1 (en) | 2016-06-29 |
| ES2878126T3 (es) | 2021-11-18 |
| EP3037426B1 (en) | 2021-06-23 |
| US20160152643A1 (en) | 2016-06-02 |
| CN105452263A (zh) | 2016-03-30 |
| KR20160046795A (ko) | 2016-04-29 |
| DK3037426T3 (da) | 2021-07-19 |
| BR112016000802B1 (pt) | 2021-05-18 |
| JP6618049B2 (ja) | 2019-12-11 |
| CN111057104A (zh) | 2020-04-24 |
| KR102301768B1 (ko) | 2021-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102388192B1 (ko) | 경화성 조성물 및 그 경화물 | |
| JP6120661B2 (ja) | アニオン硬化性化合物用硬化剤、硬化性組成物、硬化物、及び新規イミダゾール系化合物 | |
| JP5611192B2 (ja) | エポキシ樹脂、エポキシ樹脂組成物及び硬化物 | |
| JPWO2018235425A1 (ja) | 活性エステル樹脂並びにこれを用いた組成物および硬化物 | |
| JPH07292067A (ja) | 変性エポキシ樹脂の製造方法と製造された変性エポキシ樹脂及びこのエポキシ樹脂の組成物 | |
| 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 | |
| TWI623546B (zh) | 含磷化合物及含有其之硬化性環氧樹脂組合物 | |
| 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 | |
| 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 | |
| US7074946B2 (en) | Method of producing glycidyl 2-hydroxyisobutyrate | |
| JP6307245B2 (ja) | エポキシ樹脂組成物 | |
| JP4605855B2 (ja) | エポキシ樹脂組成物 | |
| JP2006022153A (ja) | 硬化性樹脂組成物 | |
| WO2023074258A1 (ja) | 活性エステル化合物 | |
| WO2023021900A1 (ja) | 活性エステル化合物 |