TW201518312A - 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
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- TW201518312A TW201518312A TW103132525A TW103132525A TW201518312A TW 201518312 A TW201518312 A TW 201518312A TW 103132525 A TW103132525 A TW 103132525A TW 103132525 A TW103132525 A TW 103132525A TW 201518312 A TW201518312 A TW 201518312A
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- Prior art keywords
- group
- phosphorus
- containing compound
- epoxy resin
- alkyl group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 66
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 58
- 239000011574 phosphorus Substances 0.000 title claims abstract description 58
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 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 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 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 23
- 239000004593 Epoxy Substances 0.000 claims description 12
- 239000004848 polyfunctional curative Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 4
- 230000007246 mechanism Effects 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 5
- 230000009257 reactivity Effects 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- -1 phosphorus compound Chemical class 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- 239000000243 solution Substances 0.000 description 14
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000003063 flame retardant Substances 0.000 description 10
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- 238000005481 NMR spectroscopy Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 8
- 235000013824 polyphenols Nutrition 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 5
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 4
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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- 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
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- 229910019142 PO4 Inorganic materials 0.000 description 3
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Abstract
本發明提供一種新穎之含磷化合物，其藉由具有與縮水甘油基之反應性，而能夠提供可期待阻燃化、低介電常數化等之硬化性環氧樹脂組合物，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之整數，R1、R2、R3及R4相互獨立地表示氫原子、烷基或芳基，R5表示烷基、烷二基、烷三基、烷四基或芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或=NR'，R'表示氫原子、烷基或芳基)
Description
本發明係關於一種含磷化合物，詳細而言係關於一種藉由具有反應性且與環氧化合物併用而能夠提供可期待阻燃化、低介電常數化等之硬化性環氧樹脂組合物的含磷化合物。
近年來，對於世界性環境問題、對人體之安全性之關心日益提高，而且對於電氣、電子製品，除阻燃性以外，更低之有害性、更高之安全性之要求日益增大。即，期望較少地產生有害性氣體或冒煙。
溴系阻燃劑具有良好之阻燃性，但燃燒時產生有害之鹵化氫(溴化氫)氣體，因此其使用正受到抑制。因此，開發有對通常之環氧樹脂調配非鹵系阻燃劑、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有以下問題：阻燃化效果不充分，對環氧樹脂之硬化造成不良影響，或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，磷酸三苯酯被廣泛用於各種樹脂，於專利文獻1中提出有將作為高分子量型磷系阻燃劑之包含二酚及苯酚之磷系阻燃劑用於環氧樹脂。
然而，為了利用該等阻燃劑賦予充分之阻燃性，而必須大量地調配，若大量地調配而滿足阻燃性，則玻璃轉移溫度降低，反之，若為了提高玻璃轉移溫度而使阻燃劑之調配量較少，則阻燃性不足。又，於專利文獻2中提出了使用反應性磷酸酯化合物，但若將磷酸酯
組入樹脂中，則容易吸濕，或者一部分成為三維結構而導致環氧樹脂之黏度增大，作業性大幅降低，因此不實用。
專利文獻1：日本專利特開平8-337709號公報
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，具體而言，目的在於提供一種藉由具有與縮水甘油基之反應性，而能夠提供可期待阻燃化、低介電常數化等之硬化性環氧樹脂組合物的含磷化合物。
本發明者等人為了達成上述目的而努力進行研究，結果發現具有特定結構之含磷化合物為可達成上述目的之化合物，從而完成了本發明。
即，本發明提供下述通式(I)所表示之含磷化合物。
(式中，m表示1~10之整數，R1、R2、R3及R4相互獨立地表示氫原子、烷基或芳基，R5表示烷基、烷二基、烷三基、烷四基或芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或=NR'，R'表示氫原子、烷基或芳基)
又，本發明提供一種反應方法，其特徵在於：上述含磷化合物以下述反應機制與環氧化合物進行反應。
(式中，m表示1~10之整數，R1、R2、R3及R4相互獨立地表示氫原子、烷基或芳基，R5表示烷基、烷二基、烷三基、烷四基或芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或=NR'，R'表示氫原子、烷基或芳基，Ar表示芳香族基)
又，本發明提供一種含有上述含磷化合物而成之環氧樹脂硬化劑。
又，本發明提供一種含有上述環氧樹脂硬化劑而成之硬化性環氧樹脂組合物。
根據本發明，可提供與環氧樹脂之反應性優異之含磷化合物，且藉由調配該含磷化合物，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中所獲得之含磷化合物(I-1)之1H-NMR圖譜之圖。
圖2係表示實施例1中所獲得之含磷化合物(I-1)之31P-NMR圖譜之圖。
圖3係表示實施例1中所獲得之含磷化合物(I-1)之GC-MS圖譜之圖。
圖4係表示實施例2中所獲得之含磷化合物(I-2)之1H-NMR圖譜之圖。
圖5係表示實施例2中所獲得之含磷化合物(I-2)之31P-NMR圖譜之圖。
圖6係表示實施例2中所獲得之含磷化合物(I-2)之GC-MS圖譜之圖。
圖7係表示實施例3中所獲得之含磷化合物(I-3)之1H-NMR圖譜之圖。
圖8係表示實施例3中所獲得之含磷化合物(I-3)之31P-NMR圖譜之圖。
圖9係表示實施例3中所獲得之含磷化合物(I-3)之GC-MS圖譜之圖。
圖10係表示實施例4中所獲得之含磷化合物(I-9)之1H-NMR圖譜之圖。
圖11係表示實施例4中所獲得之含磷化合物(I-9)之31P-NMR圖譜之圖。
圖12係表示實施例5中所獲得之S4之1H-NMR圖譜之圖。
圖13係表示實施例5中所獲得之S4之31P-NMR圖譜之圖。
圖14係表示實施例5中所獲得之S4之GC-MS圖譜之圖。
圖15係表示實施例6中所獲得之S5之1H-NMR圖譜之圖。
圖16係表示實施例6中所獲得之S5之31P-NMR圖譜之圖。
圖17係表示實施例6中所獲得之S5之GC-MS圖譜之圖。
以下，基於較佳之實施形態對本發明進行詳細說明。
本發明之含磷化合物為通式(I)所表示之新穎化合物，其結構中含有具有與縮水甘油基之反應性之基。
通式(I)中，作為R1、R2、R3、R4及Y為=NR'時R'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、癸基等碳數1~10之烷基，作為R1、R2、R3、R4及Y為=NR'時R'所表示之芳基，例如可列舉苯基、萘基之碳數6~12之芳基等，作為R1、R2、R3、R4，較佳為碳數1~5之烷基。
作為R5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、癸基之碳數1~10之烷基等，作為R5所表示之烷二基，例如可列舉：亞甲基、伸乙基、伸丙基、伸丁基、伸辛基等碳數1~10之烷二基，作為R3所表示之烷三基，例如可列舉：亞甲三基、1,1,3-伸乙三基等碳數1~6之烷三基，作為烷四基，可列舉1,1,2,2-伸乙三基等碳數2~6之烷三基。
作為R5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，其中較佳為下述式(1)~(9)所表示之基。
[化2]
作為本發明之含磷化合物，例如可列舉下述式(I-1)~(I-9)所表示之化合物。
[化6]
[化10]
於本發明之含磷化合物中，就含磷化合物中之含磷量或獲取原料之容易性之方面而言，尤佳為如下化合物：上述通式(I)中R1、R2、R3及R4相互獨立地表示碳數1~5之烷基，R5表示上述式(1)~(9)所表示之芳香族基，X及Y表示氧原子。
本發明之含磷化合物之製造方法可藉由如下述式(A)或式(B)之方法製造。
(式(A)中，R1~R5、X及Y與上述通式(I)含義相同)
(式(B)中，R1~R5、X及Y與上述通式(I)含義相同)
作為此處所使用之鹼(base)，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(solv)，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；氯苯等鹵代芳香族烴等。
該等之反應可於-80~100℃、較佳為室溫~50℃下歷時0.5小時~72小時、較佳為1小時~24小時實施。
本發明之含磷化合物藉由下述反應機制而效率良好地與環氧化合物(環氧樹脂)反應，故而可較佳地用作環氧樹脂硬化劑。
[化11B]
(式中，m表示1~10之整數，R1、R2、R3及R4相互獨立地表示氫原子、烷基或芳基，R5表示烷基、烷二基、烷三基、烷四基或芳香族基，X表示氧原子或硫原子，Y表示氧原子、硫原子或=NR'，R'表示氫原子、烷基或芳基，Ar表示芳香族基)
於上述反應式中，作為Ar所表示之芳香族基，可列舉通式(I)中之說明中例示為R1等所表示之芳基、R5所表示之芳香族基之基等。
本發明之環氧樹脂硬化劑只要含有至少一種本發明之含磷化合物即可，可單獨使用或將複數種組合而使用。又，除本發明之含磷化合物以外，亦可使用公知之環氧樹脂硬化劑。作為公知之硬化劑，可列舉下述本發明之硬化性環氧樹脂組合物中例示之通用之環氧樹脂硬化劑。該等亦可將複數種混合而使用。
於本發明之環氧樹脂硬化劑中，本發明之含磷化合物之含量較佳為5~100質量%，更佳為20~100質量%。
本發明之硬化性環氧樹脂組合物係將包含本發明之含磷化合物而成之環氧樹脂硬化劑與環氧化合物(環氧樹脂)組合而成者。
作為用於本發明之硬化性環氧樹脂組合物之環氧化合物，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、硫代二甘醇、甘油、三羥甲基丙烷、季戊四醇、山梨醇、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、亞甲基丁二酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、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-環氧環己羧酸酯、3,4-環氧-6-甲基環己基甲基-6-甲基環己羧酸酯、雙(3,4-環氧-6-甲基環己基甲基)己二酸酯等環烯化合物之環氧化物；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、異氰尿酸三縮水甘油酯等雜環化合物。又，該等環氧化合物亦可為經末端異氰酸酯之預聚物內部交聯而成者或經多元活性氫化合物(多酚、聚胺、含羰基之化合物、聚磷酸酯等)高分子量化而成者。
作為上述環氧化合物，較佳為環氧當量70~3000者，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，因此欠佳。
於本發明之硬化性環氧樹脂組合物中，包含本發明之含磷化合物而成之環氧樹脂硬化劑及環氧化合物之使用量較佳為相對於本發明之含磷化合物1當量將環氧化合物設為0.1~5當量，更佳為1~3當
量。
較佳為於本發明之硬化性環氧樹脂組合物中使用硬化觸媒。作為此種硬化性觸媒，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聚胺類；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聚胺類；間苯二甲胺、二胺基二苯基甲烷、二胺基二苯基碸等芳香族聚胺類等。又，可列舉：藉由利用常規方法使該等聚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而製造之聚環氧加成改性物；藉由利用常規方法使該等有機聚胺類與鄰苯二甲酸、間苯二甲酸、二聚酸等羧酸類反應而製造之醯胺化改性物；藉由利用常規方法使該等聚胺類與甲醛等醛類及苯酚、甲酚、二甲苯酚、第三丁基苯酚、間苯二酚等核內具有至少一個醛化反應性部位之酚類反應而製造之曼尼希化改性物等。進而，亦可使用二氰基二醯胺、酸酐、咪唑類等潛伏性硬化劑。
又，本發明之硬化性環氧樹脂組合物亦可視需要含有單縮水甘油醚類、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稀釋劑(塑化劑)；玻璃纖維、碳纖維、纖維素、矽砂、水泥、高嶺土、黏土、氫氧化鋁、膨潤土、滑石、氧化矽、細粉末氧化矽、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-環氧基環己基)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；膠體氧化矽、膠體氧化鋁等常用添加物，進而亦可併用二甲苯樹脂、石油樹脂等黏著性樹脂類。
本發明之硬化性環氧樹脂組合物例如可用於對混凝土、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、黏著標籤、冷凍食品標籤、可撕標籤、POS標籤、黏著牆紙、黏著地板材之黏著劑；銅版紙、輕量塗佈紙、塗料紙、塗佈紙板、無碳影印機、浸漬紙等加工紙；天然纖維、合成纖維、玻璃纖維、碳纖維、金屬纖維等之上漿劑、防散紗劑、加工劑等纖維處理劑；密封材料、水泥混和劑、防水材料等建築材料；電子、電氣設備用密封劑等廣泛之用途。
其次，藉由實施例進而詳細地說明本發明，但本發明不受該等實施例任何限定。
向具備轉子、回流管及隔墊之100mL三口燒瓶中加入4-甲基胺基吡啶(DMAP)0.1g(1mmol)。充分地乾燥並進行氮氣置換，利用注射器加入苯酚0.9g(10mmol)、超脫水四氫呋喃10mL。以反應溫度不超過30℃之方式利用注射器滴加雙(二甲胺基)磷醯氯2.0g(12mmol)。滴
加結束後攪拌10分鐘，並以反應溫度不超過40℃之方式利用注射器滴加三乙胺1.2g(12mmol)。滴加結束後攪拌一晚。對反應溶液添加飽和氯化銨水溶液5mL及水5mL並充分攪拌。將反應溶液移至分液漏斗，並利用二乙醚10mL萃取3次，獲得有機層。利用水10mL將有機層洗淨，利用無水硫酸鎂加以乾燥，並利用蒸發器去除溶劑，獲得淺黃色液體(粗產率93.3%、GC(Gas chromatography，氣相層析)純度70.5%)。利用管柱層析法(固定相：矽膠，移動相：乙酸乙酯(2vol)/己烷(1vol)，Rf=0.20)對粗產物進行純化，藉此獲得目標含磷化合物[I-1](無色液體，總產率：44.0%，GC純度：>99%，31P-NMR：15.94ppm)。將鑑定結果示於圖1(1H-NMR)、圖2(31P-NMR)及圖3(GC-MS)。
將具備轉子、回流管及隔墊之100mL三口燒瓶充分乾燥並進行氮氣置換。一面利用食鹽/冰水浴進行冷卻，一面加入乙胺四氫呋喃溶液9.5g(21mmol)、三乙胺2.1g(21mmol)及超脫水四氫呋喃5mL。攪拌5分鐘後，以反應溫度不超過0℃之方式利用注射器滴加二氯磷酸苯酯2.1g(10mmol)。滴加結束後，進而攪拌1小時。去除食鹽/冰水浴，並於室溫下攪拌一晚。對反應溶液添加飽和氯化銨水溶液5mL、水5mL並充分攪拌。將溶液移至分液漏斗，並利用乙酸乙酯10mL萃取3次，獲得有機層。利用水10mL將有機層洗淨，利用無水硫酸鎂加以乾燥，並利用蒸發器去除溶劑，獲得淺黃色液體(粗產率92.9%，GC純度98.5%)。利用管柱層析法(固定相：矽膠，移動相：乙酸乙酯，Rf=0.23)對粗產物進行純化，藉此獲得目標含磷化合物[I-2](無色液體，總產率：73.8%，GC純度：>99%，31P-NMR：12.01ppm)。將鑑定結果示於圖4(1H-NMR)、圖5(31P-NMR)及圖6(GC-MS)。
將具備轉子、回流管及隔墊之100mL三口燒瓶充分乾燥並進行氮氣置換。一面利用食鹽/冰水浴進行冷卻一面加入甲胺四氫呋喃溶液9.0g(21mmol)、三乙胺2.1g(21mmol)及超脫水四氫呋喃5mL。攪拌5分鐘後，以反應溫度不超過0℃之方式利用注射器滴加二氯磷酸苯酯2.1g(10mmol)。滴加結束後，進而攪拌1小時。去除食鹽/冰水浴，並於室溫下攪拌一晚。對反應溶液添加丙酮10mL並充分攪拌，藉由過濾而分離成固形物成分及濾液。對所獲得之固形物成分添加丙酮10mL並充分攪拌，再次分離成固形物成分及濾液。以同樣之程序再次利用丙酮將固形物成分洗淨。回收所有濾液並利用蒸發器去除溶劑，獲得淺黃色結晶(粗產率110.3%，GC純度95.5%)。對粗產物進行管柱層析(固定相：矽膠，移動相：乙酸乙酯(6vol)/甲醇(1vol)、Rf=0.46)，藉此獲得目標含磷化合物[I-3](白色結晶，總產率：56.5%，GC純度：97.4%，31P-NMR：15.27ppm)。將鑑定結果示於圖7(1H-NMR)、圖8(31P-NMR)及圖9(GC-MS)。
向具備轉子、回流管及氮氣(N2)導入口之30mL雙口燒瓶中加入氯化鎂0.03g(0.3mmol)、4,4'-亞甲基聯苯酚2.00g(10mmol)及氧氯化磷30.67g(200mmol)。一面導入氮氣(N2)一面加熱直至反應溶液回流，以該狀態之溫度攪拌一晚。導入之氮氣(N2)係自回流管上部排出，使所有排氣通入氫氧化鈉水溶液，捕獲反應中產生之氯化氫。反應後，利用蒸發器去除過量之氧氯化磷，獲得黃色液體(中間體)。將所獲得之中間體利用脫水四氫呋喃10mL溶解，製備中間體之THF溶液。其次，將具備轉子、回流管及隔墊之100mL三口燒瓶充分乾燥並進行氮氣置換。一面利用食鹽/冰水浴進行冷卻一面加入甲胺四氫呋喃溶液18.08g(42mmol)、三乙胺4.25g(42mmol)。攪拌5分鐘後，
以反應溫度不超過20℃之方式利用注射器滴加中間體之THF溶液。滴加結束後，進而攪拌1小時。去除食鹽/冰水浴並於室溫下攪拌一晚。反應後，利用蒸發器去除溶劑及過量之原料，獲得淺黃色固體。對粗產物進行管柱層析(固定相：矽膠，移動相：乙酸乙酯(5vol.)/甲醇(1vol.)、Rf=0.29)，藉此獲得目標含磷化合物[I-9](白色固體，總產率：35.2%)。將鑑定結果示於圖10(1H-NMR)及圖11(31P-NMR)。
按照下述反應式，於存在觸媒DMPA 2.3mg(7.5mol%)之條件下，使實施例2中所獲得之含磷化合物[I-2]57.1mg(0.25mmol)與ADEKA GLYCIROL ED-509S 51.6mg(0.25mmol)在氮氣流下、140℃下反應2小時。根據1H-NMR(圖12)、31P-NMR(圖13)及GC-MS(圖14)確認到主產物中獲得S4。
按照下述反應式，於存在觸媒DMPA 2.3mg(7.5mol%)之條件下，使實施例3中所獲得之含磷化合物[I-3]50.0mg(0.25mmol)與ADEKA GLYCIROL ED-509S 51.6mg(0.25mmol)在氮氣流下、130℃下反應2小時。根據1H-NMR(圖15)、31P-NMR(圖16)及GC-MS(圖17)確認到主產物中獲得S5。
將ADEKA RESIN EP-4100L 1.02g(100.0phr.)、本發明之含磷化合物[I-9]0.16g(15.7phr.)及2-乙基-4-甲基咪唑0.03g(3.0phr.)進行混合，於恆溫槽中以150℃加熱3小時，繼而以180℃加熱3小時，獲得不發黏之褐色硬化物。利用DSC(differential scanning calorimetry，示差掃描熱量測定)研究該硬化物之Tg，結果為140℃。
根據本發明之實施例，揭示出本發明之含磷化合物與縮水甘油基具有反應性。藉由將本發明之磷酸酯調配至環氧樹脂組合物中，能
夠提供可期待硬化物物性之降低受到抑制且具有阻燃性、低介電常數之環氧樹脂硬化物。
Claims (6)
- 一種下述通式(I)所表示之含磷化合物，
- 如請求項1之含磷化合物，其中R5所表示之芳香族基係由下述式(1)至(9)中之任一式所表示，
- 如請求項1之含磷化合物，其中於上述通式(I)中，R1、R2、R3及R4相互獨立地表示碳數1~5之烷基，R5表示上述式(1)~(9)所表示之芳香族基，X及Y表示氧原子。
- 一種反應方法，其特徵在於：如請求項1之含磷化合物以下述反應機制與環氧化合物進行反應，
- 一種環氧樹脂硬化劑，其係含有如請求項1之含磷化合物而成。
- 一種硬化性環氧樹脂組合物，其係含有如請求項5之環氧樹脂硬化劑而成。
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| JP2019038989A (ja) * | 2017-08-23 | 2019-03-14 | 株式会社Adeka | 難燃性エポキシ樹脂組成物 |
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| 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 |
| US3531550A (en) * | 1965-08-12 | 1970-09-29 | Monsanto Co | Phosphorus ester amides |
| NL131206C (zh) * | 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 |
| FR2102301A1 (zh) * | 1970-08-17 | 1972-04-07 | Monsanto Co | |
| AU5867073A (en) * | 1972-07-31 | 1975-01-30 | Monsanto Co | Phosphoroamidates |
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| JPS5093949A (zh) * | 1973-12-24 | 1975-07-26 | ||
| DD117153A3 (zh) * | 1974-02-12 | 1976-01-05 | ||
| 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 |
| 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 |
| 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 |
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| JP6499968B2 (ja) | 2019-04-10 |
| KR20160065814A (ko) | 2016-06-09 |
| BR112016005231B1 (pt) | 2021-04-13 |
| EP3053928A1 (en) | 2016-08-10 |
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| TWI623547B (zh) | 2018-05-11 |
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