CN105452263A - 含磷化合物及含有该含磷化合物的固化性环氧树脂组合物 - Google Patents
含磷化合物及含有该含磷化合物的固化性环氧树脂组合物 Download PDFInfo
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- CN105452263A CN105452263A CN201480043901.7A CN201480043901A CN105452263A CN 105452263 A CN105452263 A CN 105452263A CN 201480043901 A CN201480043901 A CN 201480043901A CN 105452263 A CN105452263 A CN 105452263A
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- Prior art keywords
- alkyl
- base
- contained compound
- epoxy resin
- alkane
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 229920000647 polyepoxide Polymers 0.000 title claims description 24
- 239000003822 epoxy resin Substances 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 title abstract description 6
- 239000011574 phosphorus Substances 0.000 title abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000007246 mechanism Effects 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 abstract description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- -1 phosphorus compound Chemical class 0.000 description 35
- 239000000126 substance Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000003063 flame retardant Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 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 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 235000013824 polyphenols Nutrition 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000123 paper Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 150000002460 imidazoles Chemical class 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
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- 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
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
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- 230000000704 physical effect Effects 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 2
- 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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- WHAMSPBTGLCOJH-UHFFFAOYSA-N C(C)(C)(C1=C(C=CC=C1)O)C1=C(C=CC=C1)O.OC(CC)(C1=CC=CC=C1)O Chemical compound C(C)(C)(C1=C(C=CC=C1)O)C1=C(C=CC=C1)O.OC(CC)(C1=CC=CC=C1)O WHAMSPBTGLCOJH-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
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- 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
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes 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
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
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Classifications
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- 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
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Abstract
本发明提供与缩水甘油基具有反应性的含磷化合物,具体而言,提供下述通式(I)所表示的含磷化合物。式中,m表示1~10的数,R1、R2彼此独立地表示氢原子、烷基、芳基,R3表示烷基、烷烃二基、烷烃三基、烷烃四基、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表示氢原子、烷基、芳基,
Description
技术领域
本发明涉及含磷化合物,详细而言,涉及具有反应性、通过与聚环氧化合物并用能够提供可以期待阻燃化、低介电常数化等的固化性环氧树脂组合物的含磷化合物。
背景技术
近年来,随着对于世界环境问题、相对于人体的安全性的关心的提高,对于电气和电子产品,除了阻燃性以外,更少的有害性、更高的安全性的要求增大。即,迫切期望有害性气体或发烟的产生少。
溴系阻燃剂虽然具有良好的阻燃性,但是由于在燃烧时产生有害的卤化氢(溴化氢)气体,所以其使用一直受到抑制。因此,开发了在通常的环氧树脂中配合非卤素系阻燃剂、例如氮化合物、磷化合物或无机化合物等而得到的组合物。然而,这些阻燃赋予性添加剂存在以下等问题:阻燃化效果不充分,或者对环氧树脂的固化造成不良影响,或者使固化组合物的玻璃化转变温度等物性降低。
例如,作为磷系阻燃剂,磷酸三苯酯被广泛用于各种树脂中,在专利文献1中,提出了将由高分子量型即2元酚与苯酚构成的磷系阻燃剂用于环氧树脂。可是,为了通过这些阻燃剂对环氧树脂赋予充分的阻燃性,必须大量地配合阻燃剂,若满足阻燃性则玻璃化转变温度降低,若提高玻璃化转变温度则阻燃性不足。此外,在专利文献2中,提出了使用反应性的磷酸酯化合物作为阻燃剂,但由于若磷酸酯被加入树脂中,则树脂变得容易吸湿,一部分变成三维结构而环氧树脂的粘度增大,操作性大大降低,所以并不实用。
现有技术文献
专利文献
专利文献1:US5739187(A)
专利文献2:日本特开平10-195178号公报
发明内容
发明所要解决的问题
本发明的目的在于提供与缩水甘油基具有反应性的含磷化合物,并提供由此可以提供能够期待阻燃化、低介电常数化等的固化性环氧树脂组合物的含磷化合物。
用于解决问题的手段
本发明人们为了解决上述课题进行了深入研究,结果发现,特定的含磷化合物为可达成上述目的的化合物,从而完成了本发明。
即,本发明提供下述通式(I)所表示的含磷化合物。
[化学式1]
(式中,m表示1~10的数,R1、R2彼此独立地表示氢原子、烷基、芳基,R3表示烷基、烷烃二基、烷烃三基、烷烃四基、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表示氢原子、烷基、芳基。)
发明效果
根据本发明,能够提供与环氧树脂的反应性优异的含磷化合物,能够期待环氧树脂的阻燃化、低介电常数化等。
附图说明
图1是表示实施例1中得到的含磷化合物的1H-NMR的图。
图2是表示实施例1中得到的含磷化合物的31P-NMR的图。
图3是表示实施例1中得到的含磷化合物的GC-MS的图。
图4是表示实施例2中得到的P2的1H-NMR的图。
图5是表示实施例2中得到的P2的31P-NMR的图。
图6是表示实施例2中得到的P2的GC-MS的图。
具体实施方式
以下,对本发明的含磷化合物进行详细说明。
通式(I)中,作为R1、R2所表示的烷基,可列举出例如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、异戊基、叔戊基、己基、异己基、辛基、2-乙基己基、叔辛基、壬基、癸基等,作为R1、R2所表示的芳基,可列举出例如苯基、萘基等,作为R3所表示的烷基,可列举出例如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、异戊基、叔戊基、己基、异己基、辛基、2-乙基己基、叔辛基、壬基、癸基等,作为R3所表示的芳基,可列举出例如苯基、萘基等,作为R3所表示的烷烃二基,可列举出例如亚甲基、亚乙基、亚丙基、亚丁基、亚辛基等,作为R3所表示的烷烃三基,可列举出例如亚甲基三基、1,1,3-亚乙基三基等,作为R3所表示的烷烃四基,可列举出1,1,2,2-亚乙基三基等。作为R3所表示的芳香族基,可列举出例如氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的残基;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、亚异丙基双酚(双酚A)、亚异丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺酰基双酚、氧代双苯酚、线型酚醛清漆、邻甲酚酚醛清漆、乙基线型酚醛清漆、丁基线型酚醛清漆、辛基线型酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的残基等,其中,优选使用下述式所表示的基团。
[化学式2]
作为本发明的含磷化合物,优选上述通式(I)中R1表示碳原子数为1~5的烷基、R2表示碳原子数为1~5的烷基、R3表示芳香族基、X及Y表示氧原子的含磷化合物。
作为本发明的含磷化合物,可列举出例如下述式(I-1)~(I-8)所表示的化合物。
[化学式3]
[化学式4]
[化学式5]
[化学式6]
[化学式7]
[化学式8]
[化学式9]
[化学式10]
本发明的含磷化合物的制造方法可以通过如下述式所示的方法来制造。
[化学式11]
(式中,m、R1、R2、R3、X、Y与上述的m、R1、R2、R3、X、Y相同。)
作为这里使用的碱,可列举出例如三乙基胺、三丁基胺、二氮杂二环十一碳烯、二氮杂二环壬烯、1,4-二氮杂二环[2.2.2]辛烷等叔胺、吡啶、N,N-二甲基氨基吡啶等吡啶类、1-甲基咪唑等咪唑类、三苯基膦、三丁基膦、三环己基膦等膦类等。
作为这里使用的溶剂,可列举出例如甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、丙二醇单甲基醚醋酸酯、环己酮等酮类;四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇单甲基醚等醚类;醋酸乙酯、醋酸正丁酯等酯类;苯、甲苯、二甲苯等芳香族烃;四氯化碳、氯仿、三氯乙烯、二氯甲烷等卤代脂肪族烃;氯苯等卤代芳香族烃等。
这些反应可以在-80~100℃、优选在室温~50℃下、用0.5小时~72小时、优选1小时~24小时实施。
本发明还提供一种反应方法,其特征在于,上述含磷化合物通过下述反应机理与环氧化合物进行反应。
[化学式12]
(式中,m表示1~10的数,R1、R2彼此独立地表示氢原子、烷基、芳基,R3表示烷基、烷烃二基、烷烃三基、烷烃四基、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表示氢原子、烷基、芳基。)
本发明的含磷化合物通过与聚环氧化合物组合,提供固化性环氧树脂组合物。
作为本发明中使用的聚环氧化合物,可列举出例如氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化合物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、亚异丙基双酚(双酚A)、亚异丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺酰基双酚、氧代双苯酚、线型酚醛清漆、邻甲酚酚醛清漆、乙基线型酚醛清漆、丁基线型酚醛清漆、辛基线型酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、硫代二甘醇、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧乙烷加成物等多元醇类聚缩水甘油醚;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三酸、均苯四酸、四氢邻苯二甲酸、六氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯类及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、二环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物、三缩水甘油基异氰脲酸酯等杂环化合物。此外,这些环氧树脂也可以是通过末端异氰酸酯的预聚物进行内部交联而得到的物质或以多价的活性氢化合物(多元酚、多胺、含羰基化合物、聚磷酸酯等)经过高分子量化而得到的物质。
此外,聚环氧化合物优选环氧当量为70~3000、进一步为90~2000的化合物。由于该环氧当量低于70时,有可能固化物的物性降低,在大于3000的情况下,有可能得不到充分的固化性,所以不优选。
本发明的固化性环氧树脂组合物中,优选使用固化催化剂,使用对二甲基氨基吡啶、三苯基膦、咪唑、叔胺、膦、季铵盐、季鏻盐。
本发明的固化性环氧树脂组合物中,可以使用通用的环氧树脂固化剂,作为该环氧树脂固化剂,可列举出例如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-酚等咪唑类;二亚乙基三胺、三亚乙基三胺、四亚乙基五胺等聚烷基多胺类;1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、异佛尔酮二胺等脂环式多胺类;间苯二甲基二胺、二氨基二苯基甲烷、二氨基二苯基砜等芳香族多胺类等。此外,可列举出通过使这些多胺类与苯基缩水甘油醚、丁基缩水甘油醚、双酚A-二缩水甘油醚、双酚F-二缩水甘油醚等缩水甘油醚类或羧酸的缩水甘油酯类等各种环氧树脂利用常规方法反应而制造的聚环氧加成改性物;通过使这些有机多胺类与邻苯二甲酸、间苯二甲酸、二聚酸等羧酸类利用常规方法反应而制造的酰胺化改性物;通过使这些多胺类与甲醛等醛类及苯酚、甲酚、二甲苯酚、叔丁基苯酚、间苯二酚等核上至少具有一个醛化反应性部位的酚类利用常规方法反应而制造的曼尼希化改性物等。进而还可以使用双氰胺、酸酐、咪唑类等潜在性固化剂。
此外,根据需要,也可以含有单缩水甘油醚类、邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇、煤焦油等反应性或非反应性的稀释剂(增塑剂);玻璃纤维、碳纤维、纤维素、硅砂、水泥、高岭土、粘土、氢氧化铝、膨润土、滑石、二氧化硅、微粉末二氧化硅、二氧化钛、炭黑、石墨、氧化铁、沥青物质等填充剂或颜料;γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷等硅烷偶联剂;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯、芳香族醚等润滑剂;增稠剂;触变剂;抗氧化剂;光稳定剂;紫外线吸收剂;阻燃剂;消泡剂;防锈剂;胶体二氧化硅、胶体氧化铝等常用的添加物,进而,还可以并用二甲苯树脂、石油树脂等粘合性的树脂类。
本发明的固化性环氧树脂组合物可以用于例如相对于混凝土、水泥灰浆、各种金属、皮革、玻璃、橡胶、塑料、木、布、纸等的涂料或粘接剂;包装用粘合带、粘合标签、冷冻食品标签、可移动标签、POS标签、粘合壁纸、粘合地板材料的粘合剂;美术纸、轻量涂布纸、流延涂布纸、涂敷板纸、无碳复印纸、浸渗纸等加工纸;天然纤维、合成纤维、玻璃纤维、碳纤维、金属纤维等的施胶剂、防磨损剂、加工剂等纤维处理剂;天花板材料、水泥混合剂、防水材料等建筑材料;电子和电气设备用密封剂等广泛的用途中。
实施例
接着,通过实施例对本发明进一步进行详细说明,但本发明并不受这些实施例的任何限定。
实施例1
含磷化合物〔I-1〕的合成
将具备转子、回流管、隔片的100mL三口烧瓶充分干燥,进行氮气置换,通过注射器注入苯酚0.75g(8.8mmol)、三乙基胺0.89g(8.8mmol)、超脱水四氢呋喃3mL。在另外的容器中投入二甲基膦酰氯0.90g(8mmol)、超脱水四氢呋喃3mL,调整二甲基膦酰氯溶液。将经调整的二甲基膦酰氯溶液按照反应温度不超过30℃的方式用注射器进行滴加。滴加结束后,搅拌一夜。在反应溶液中添加饱和氯化铵水溶液5mL、水5mL并充分搅拌。将溶液转移至分液漏斗中,用醋酸乙酯10mL萃取3次,得到有机层。将有机层用水10mL洗涤,用无水硫酸镁干燥,用蒸发器将溶剂除去而得到淡黄色液体。将(粗收率:60.3%、GC纯度:87.1%)粗产物通过柱色谱法(固定相:硅胶、流动相:醋酸乙酯、Rf=0.07)进行精制,得到目标含磷化合物〔I-1〕(白色结晶、总收率:45.8%、GC纯度:>99%、31P-NMR:52.44ppm)。将所得到的含磷化合物的1H-NMR、31P-NMR及GC-MS分别示于图1~3中。
实施例2
在DMAP0.9mg(7.5mol%)催化剂存在下,使含磷化合物〔I-1〕17.0mg(0.25mmol)与AdekaGlycirolED-509S20.6mg(0.25mmol)在氮气流下、160℃下反应2小时。通过下述的[化学式13]中所示的反应机理,高选择性地得到[化学式13]中所示的P2。将所得到的P2的1H-NMR、31P-NMR及GC-MS分别示于图4~6中。
[化学式13]
由本发明的实施例显示,本发明的含磷化合物与缩水甘油基具有反应性。通过将本发明的磷酸酯配合到环氧树脂组合物中,能够提供可期待固化物的物性的降低受到抑制、具有阻燃性、低介电常数的环氧树脂固化物。
Claims (5)
1.一种含磷化合物,其以下述通式(I)表示,
式中,m表示1~10的数,R1、R2彼此独立地表示氢原子、烷基、芳基,R3表示烷基、烷烃二基、烷烃三基、烷烃四基、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表示氢原子、烷基、芳基。
2.根据权利要求1所述的含磷化合物,其特征在于,R3所表示的芳香族基以下述式表示,
3.根据权利要求1或2所述的含磷化合物,其特征在于,在所述通式(I)中,R1表示碳原子数为1~5的烷基,R2表示碳原子数为1~5的烷基,R3表示所述芳香族基,X及Y表示氧原子。
4.一种反应方法,其特征在于,权利要求1~3中任一项所述的含磷化合物通过下述反应机理与环氧化合物进行反应,
式中,m表示1~10的数,R1、R2彼此独立地表示氢原子、烷基、芳基,R3表示烷基、烷烃二基、烷烃三基、烷烃四基、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表示氢原子、烷基、芳基。
5.一种固化性环氧树脂组合物,其含有权利要求1~3中任一项所述的含磷化合物。
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