JP2014201732A - 4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物及びその製造法並びにそれらを含有するラジカル重合性組成物及びその重合物 - Google Patents
4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物及びその製造法並びにそれらを含有するラジカル重合性組成物及びその重合物 Download PDFInfo
- Publication number
- JP2014201732A JP2014201732A JP2013081680A JP2013081680A JP2014201732A JP 2014201732 A JP2014201732 A JP 2014201732A JP 2013081680 A JP2013081680 A JP 2013081680A JP 2013081680 A JP2013081680 A JP 2013081680A JP 2014201732 A JP2014201732 A JP 2014201732A
- Authority
- JP
- Japan
- Prior art keywords
- naphthyl
- oxy
- hydroxy
- acrylate
- phosphate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 4-[(di-substituted phosphoryl)oxy]-1-naphthyl Chemical group 0.000 title claims abstract description 120
- 229920000642 polymer Polymers 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000007870 radical polymerization initiator Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052753 mercury Inorganic materials 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 5
- 125000004437 phosphorous atom Chemical group 0.000 abstract description 5
- 230000009970 fire resistant effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 239000003063 flame retardant Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NTNOSKVPKWSUDB-UHFFFAOYSA-N (4-diethoxyphosphoryloxynaphthalen-1-yl) 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC1=CC=C(C2=CC=CC=C12)OP(=O)(OCC)OCC NTNOSKVPKWSUDB-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 238000004811 liquid chromatography Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- JJNWWDRVFBEJOH-UHFFFAOYSA-N (4-diphenoxyphosphoryloxynaphthalen-1-yl) 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC1=CC=C(C2=CC=CC=C12)OP(=O)(OC1=CC=CC=C1)OC1=CC=CC=C1 JJNWWDRVFBEJOH-UHFFFAOYSA-N 0.000 description 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- VJTIHVVXNASAJZ-UHFFFAOYSA-N (4-dimethoxyphosphoryloxynaphthalen-1-yl) 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC1=CC=C(C2=CC=CC=C12)OP(=O)(OC)OC VJTIHVVXNASAJZ-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- OURFWHUAQFXKSK-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C(C3=CC=CC=C3C(=C2C4=CC=CC=C4)OP(=O)(O)O)O Chemical compound C1=CC=C(C=C1)C2=C(C3=CC=CC=C3C(=C2C4=CC=CC=C4)OP(=O)(O)O)O OURFWHUAQFXKSK-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- GZIWDJCUGGGAIY-UHFFFAOYSA-N (4-hydroxy-2,3-dimethylnaphthalen-1-yl) dihydrogen phosphate Chemical compound C1=CC=CC2=C(O)C(C)=C(C)C(OP(O)(O)=O)=C21 GZIWDJCUGGGAIY-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- MRPGLZGPIMUOJG-UHFFFAOYSA-N CCC(C(C)=C(C1=C(C)C=CC=C11)O)=C1OP(O)(O)=O Chemical compound CCC(C(C)=C(C1=C(C)C=CC=C11)O)=C1OP(O)(O)=O MRPGLZGPIMUOJG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WBANXBXFCKKMKU-UHFFFAOYSA-N diethyl (4-hydroxynaphthalen-1-yl) phosphate Chemical compound CCOP(=O)(OCC)Oc1ccc(O)c2ccccc12 WBANXBXFCKKMKU-UHFFFAOYSA-N 0.000 description 4
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003136 n-heptyl 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])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- GUJZYNPNQPJNLH-UHFFFAOYSA-N (4-diethoxyphosphoryloxynaphthalen-1-yl) prop-2-enoate Chemical compound C(C=C)(=O)OC1=CC=C(C2=CC=CC=C12)OP(=O)(OCC)OCC GUJZYNPNQPJNLH-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- XJACNVFYWIDFBJ-UHFFFAOYSA-N 2-diphenylphosphorylnaphthalene-1,4-diol Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C(=C1)O)O XJACNVFYWIDFBJ-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- OPKFWRVRCVCMJH-UHFFFAOYSA-N 6-methylnaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(C)=CC=C21 OPKFWRVRCVCMJH-UHFFFAOYSA-N 0.000 description 2
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- RVUWUNKXRXPIBJ-UHFFFAOYSA-N CCCCC1=C(C2=C(C(=C(C(=C2C=C1)OP(=O)(O)O)CCCC)C)O)C Chemical compound CCCCC1=C(C2=C(C(=C(C(=C2C=C1)OP(=O)(O)O)CCCC)C)O)C RVUWUNKXRXPIBJ-UHFFFAOYSA-N 0.000 description 2
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- 241000254158 Lampyridae Species 0.000 description 2
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- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical class C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- UFFAFBPZFGAMJJ-UHFFFAOYSA-N (2-methoxy-4,6-dimethylphenyl)boronic acid Chemical compound COC1=CC(C)=CC(C)=C1B(O)O UFFAFBPZFGAMJJ-UHFFFAOYSA-N 0.000 description 1
- HEXDQNXIVJEYLG-UHFFFAOYSA-N (2-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1C HEXDQNXIVJEYLG-UHFFFAOYSA-N 0.000 description 1
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- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明の4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物は、一般式(2)に示すジ置換−4−ヒドロキシ−1−ナフチルホスフェート化合物を(メタ)アクリロイル化することにより得ることができる。
ジメチル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート、ジエチル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート、ジ−n−プロピル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート、ジ−n−ブチル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート、ジメチル−4−ヒドロキシ−n−6−ブチル−1−ナフチルホスフェート、ジフェニル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート、ジトリル−4−ヒドロキシ−6−n−ブチル−1−ナフチルホスフェート等が挙げられる。
かくして得られた4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物は、ラジカル重合開始剤を用いることによりラジカル重合し、重合物とすることができる。ラジカル重合開始剤としては、熱ラジカル重合開始剤及び光ラジカル重合開始剤を用いることができる。
本発明の4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物及び上記ラジカル重合開始剤を混合することによりラジカル重合性組成物を調製したのち重合させることができる。
当該ラジカル重合性組成物の重合はフィルム状で行うことも出来るし、塊状に硬化させることも可能である。フィルム状に重合させる場合は、液状の当該重合性組成物をたとえばポリエステルフィルムなどの基材に、たとえばバーコーターなどを用いて膜厚5〜300ミクロンになるように塗布する。本発明の4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物は、薄膜だけでなく厚膜においても容易に重合させることができる。
(1)融点:ゲレンキャンプ社製の融点測定装置、型式MFB−595(JIS K0064に準拠)
(2)屈折計:エルマー社製 型式ER−7MWH
(3)赤外線(IR)分光光度計:日本分光社製、型式IR−810
(4)核磁気共鳴装置(NMR):日本電子社製、型式GSX FT NMR Spectorometer
反応容器に1,4−ナフトキノン5.0g(31.6mmol)、亜リン酸ジメチル5.2g(47.4mmol)および溶媒としてトルエン40mlを仕込んだ。この混合物を窒素気流化、室温で撹拌しながら、ここへ触媒として1,8−ジアザビシクロ[5,4,0]−7−ウンデセン(以下、DBUとよぶ)200mgをトルエン10mlに溶かした溶液を5分かけて添加した。この間、反応液温度は19℃から43℃まで上昇した。放冷により室温まで戻した後、油浴上で55℃に加熱し、30分間撹拌を行った。反応終了時点で器壁に結晶が多量付着しているのが認められた。反応器を氷水に浸して放置した後、析出結晶をろ過により取得した。この褐色結晶、6.0gを更にトルエンから再結晶し、淡褐色の結晶、5.1gを得た。このものは分析の結果、ジメチル−4−ヒドロキシ−1−ナフチルホスフェートであり、高速液体クロマトグラフィー(LC)純度はピーク面積比で93.5%であった。結晶までの通し収率は、60.7モル%であった。一方、結晶を除いた反応母液を水洗した後、得られた有機層から溶媒を減圧留去し、褐色液体、2.3gを得た。このものをLCで分析したところ、その組成は、ピーク面積比でジメチル−4−ヒドロキシ−1−ナフチルホスフェートが33.9%、2−ジメトキシホスホリル−1,4−ジヒドロキシナフタレンが48.1%であった。
(1)融点:141.0−141.6℃
(2)IR(KBr,cm−1):3205、1635、1595、1460、1388、1358、1270、1240、1190、1042、935、918、857、830、773
(3)MS−スペクトル:M+=268
反応容器に1,4−ナフトキノン2.0g(12.6mmol)、亜リン酸ジエチル2、6g(18.9mmol)および溶媒としてトルエン20mlを仕込んだ。この混合物を質素気流下、氷水で冷却下に撹拌。ここへ触媒としてDBU67mgをトルエンに溶かした溶液を17分かけて添加した。この間、反応液温度を20℃から25℃の範囲を保つようにした。触媒添加後、さらに室温で1時間撹拌を行った。反応液に抽出溶媒としてトルエンを更に添加し、1規定塩酸、次いで水で洗浄した後、得られた有機層から溶媒を減圧留去し、赤褐色液体、3.6gを得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、その組成は、ピーク面積比でジエチル−4−ヒドロキシ−1−ナフチルホスフェートが69.8%、2−ジエトキシホスホリル−1,4−ジヒドロキシナフタレンが17.8%であった。室温で放置すると結晶が多量析出した。これを酢酸エチル−ヘキサンの混合溶媒で洗浄して、白色結晶、1.89gを得た。このものは分析の結果、ジエチル−4−ヒドロキシ−1−ナフチルホスフェートであり、純度はピーク面積比で98%であった。結晶までの収率は49.7%であった。
(1)融点:102.3−104.2℃
(2)IR(KBr,cm−1):3190、1635、1598、1580、1476、1445、1387、1358、1263、1248、1157、1035、960、903、823、762
(3)MS−スペクトル:M+=296
反応容器に1,4−ナフトキノン3.0g(15.9mmol)、亜リン酸ジフェニル4、4g(19.1mmol)、触媒のジメチルアミノピリジン、20mgおよび溶媒としてトルエン30mlを仕込んだ。この混合物を質素気流下、70℃で50分加熱撹拌を行った。冷却後、反応液に抽出溶媒として酢酸エチルを加え、1規定塩酸、次いで水で洗浄した後、得られた有機層から溶媒を減圧留去し、暗赤色液体、6.8gを得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、その組成は、ピーク面積比でジフェニル−4−ヒドロキシ−1−ナフチルホスフェートが41.4%、2−ジフェニルホスホリル−1,4−ジヒドロキシナフタレンが9.1%、亜リン酸ジフェニルが8.8%であった。この反応粗体をシリカゲルを用いたカラムクロマト精製に付した。溶離液として酢酸エチルとヘキサンの混合溶媒を流した。亜リン酸ジフェニル、2−ジフェニルホスホリル−1,4−ジヒドロキシナフタレン次いで目的物のジフェニル−4−ヒドロキシ−1−ナフチルホスフェートの順に溶出した。目的物を含む分画から溶媒を留去すると淡褐色の結晶が得られた。これを酢酸エチル−ヘキサンから再結晶し、白色結晶、1.31gを得た。このものは分析の結果、ジフェニル−4−ヒドロキシ−1−ナフチルホスフェートであり、純度はピーク面積比で97.3%であった。
(1) 融点:101.2−103.4℃
(2)IR(KBr,cm−1):3230、1635、1590、1488、1383、1362、1260、1208、1183、1065、965、820、762
(3)MS−スペクトル:M+=392
十分に窒素置換した反応器に、合成例1と同様の方法で合成したジチル−4−ヒドロキシ−1−ナフチルホスフェート、1.0g(3.7mmol)、トリエチルアミン1.1g(11.2mmol)及び溶媒のアセトニトリル10mlを仕込んで、攪拌下に溶解した。この溶液を氷水で冷やし、反応液の温度を10−15℃に保ち、窒素気流中、攪拌下に塩化メタクリロイル590mg(5.6mmol)を20分かけて滴下した。滴下終了後、室温に戻して、更に20分間攪拌を続けて反応を終了した。当該反応液に抽出溶媒として酢酸エチルと、生成したトリエチルアミン・塩酸塩を除去するための水を加え、攪拌後、静置したところ水相と有機相の二相に分離した。この有機相を取りだし、水洗した後、溶媒を溜去することで淡黄色油状物770mgを得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、ピーク面積比で4−[(ジメトキシホスホリル)オキシ]−1−ナフチルメタクリレートの純度は95.7%であった。
(1)融点:室温で液状
(2)屈折率:nD=1.5562
(3)IR(neat,cm−1):3080、2960、2860、1740、1638、1602、1465、1392、1295、1222、1123、1043、905、875、797、763
(4)1H−NMR(270MHz、CDCl3):δ=8.13−8.18(m、1H)、7.82−7.87(m、1H)、7.44−7.62(m、3H)、7.20−7.27(m、1H)、6.50(s、1H)、6.83−6.86(m、1H)、3.87−3.92(m、6H)、2.13(s、3H)
(5)MS−スペクトル:M+=336
十分に窒素置換した反応器に、合成例2と同様の方法で合成したジエチル−4−ヒドロキシ−1−ナフチルホスフェート、2.0g(6.8mmol)、トリエチルアミン2.0g(20mmol)及び溶媒のアセトニトリル20mlを仕込んで、攪拌下に溶解した。この溶液を氷水で冷やし、反応液の温度を10−15℃に保ち、窒素気流中、攪拌下に塩化メタクリロイル1.1g(10.1mmol)を12分かけて滴下した。滴下終了後、室温に戻して、更に1時間攪拌を続けて反応を終了した。当該反応液に抽出溶媒として酢酸エチルと、生成したトリエチルアミン・塩酸塩を除去するための水を加え、攪拌後、静置したところ水相と有機相の二相に分離した。この有機相を取りだし、水洗した後、溶媒を溜去することで黄褐色油状物2.23gを得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、ピーク面積比で4−[(ジエトキシホスホリル)オキシ]−1−ナフチルメタクリレートの純度は91.6%であった。この油状物質、1.85gをグラスチューブオーブン装置(柴田科学(株)製、GTO−250RS型)を用いて、減圧蒸留を行った。200Paの減圧下、オーブン温度、220−240℃で淡黄色液体、1.41gが得られた。高速液体クロマトグラフィーの分析により、純度94.6%の目的物であった。
(1)融点:室温で液状
(2)屈折率:nD=1.5404
(3)IR(neat,cm−1):3070、2990、2940、1740、1638、1602、1467、1392、1297、1222、1122、1044、950、895、808、764、704
(4)1H−NMR(270MHz、CDCl3):δ=8.14−8.19(m、1H)、7.78−7.86(m、1H)、7.47−7.58(m、3H)、7.17−7.25(m、1H)、6.49(s、1H)、5.85(s、1H)、4.19−4.30(m、4H)、2.13(s、3H)、1.30−1.37(m、6H)
(5)MS−スペクトル:M+=364
合成例2と同様の方法で合成したジエチル−4−ヒドロキシ−1−ナフチルホスフェート、3.0g(6.8mmol)、トリエチルアミン3.0g(30mmol)及び塩化メタクリロイルの代わりに塩化アクリロイル1.4g(15.2mmol)を用いた他は、実施例2とほぼ同様の操作を行い、粗体の4−[(ジエトキシホスホリル)オキシ]−1−アクリレートを3.0gの黄褐色液体として得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、4−[(ジエトキシホスホリル)オキシ]−1−ナフチルアクリレートの純度は95.4%であった。この油状物質、3.0gを実施例2と同様にグラスチューブオーブン装置を用いて、減圧蒸留を行った。150Paの減圧下、オーブン温度、220−230℃で淡黄色液体、2.10gが得られた。高速液体クロマトグラフィーの分析により、このものはピーク面積比で純度96.5%の目的物であった。
(1)融点:室温で液状
(2)屈折率:nD=1.5476
(3)IR(neat,cm−1):3080、2990、2905、1748、1635、1600、1465、1390、1280、1220、1142、1044、905、800、764、
(4)1H−NMR(270MHz、CDCl3):δ=8.12−8.20(m、1H)、7.80−7.87(m、1H)、7.47−7.58(m、3H)、7.19−7.25(m、1H)、6.66−6.73(m、1H)、6.40−6.48(m、1H)、6.07−6.11(m、1H),4.17−4.28(m、4H)、1.27−1.37(m、6H)
(5)MS−スペクトル:M+=350
十分に窒素置換した反応器に、合成例3と同様の方法で合成したジフェニル−4−ヒドロキシ−1−ナフチルホスフェート、750mg(1.9mmol)、トリエチルアミン570mg(5.7mmol)及び溶媒のアセトニトリル10mlを仕込んで、攪拌下に溶解した。この溶液を氷水で冷やし、反応液の温度を10−15℃に保ち、窒素気流中、攪拌下に塩化メタクリロイル300mg(2.9mmol)を15分かけて滴下した。滴下終了後、室温に戻して、更に30分攪拌を続けて反応を終了した。当該反応液に抽出溶媒として酢酸エチルと水を加え、攪拌後、静置したところ水相と有機相の二相に分離した。この有機相を取りだし、水洗した後、溶媒を溜去することで褐色油状物820mgを得た。このものを高速液体クロマトグラフィー(LC)で分析したところ、4−[(ジフェノキシホスホリル)オキシ]−1−ナフチルメタクリレートの純度はピーク面積比で93.5%であった。この反応粗体、700mgをシリカゲルを用いたカラムクロマト精製に付した。溶離液として酢酸エチルとヘキサンの混合溶媒を流した。目的物を含む分画から溶媒を留去すると白色結晶、70mgが得られた。このものは分析の結果、4−[(ジフェノキシホスホリル)オキシ]−1−ナフチルメタクリレートであり、純度はピーク面積比で98.5%であった。
(1)融点:48.5−49.3℃
(2)屈折率:nD=1.614
(3)IR(KBr,cm−1):1732、1635、1590、1488、1463、1390、1296、1215、1195、1125、1064、1010、962、900、775、762
(4)1H−NMR(270MHz、CDCl3):δ=8.00−8.03(m、1H)、7.82−7.86(m、1H)、7.46−7.58(m、3H)、7.18−7.38(m、11H)、6.50−6.52(m、1H)、5.84−5.88(m、1H)、2.15(s−3H)
(5)MS−スペクトル:M+=460
トリメチロールプロパントリアクリレート100重量部、合成実施例2と同様の方法で合成した4−[(ジエトキシホスホリル)オキシ]−1−ナフチルメタクリレート50重量部に対し、光ラジカル重合開始剤イルガキュア819(ビー・エー・エス・エフ社製)を1重量部添加し光ラジカル重合性組成物を調製した。次に、ポリエステルフィルム(東レ製ルミラー膜厚100ミクロン、ルミラーは東レ株式会社の登録商標)上に調製した組成物を膜厚が100ミクロンとなるようにバーコーターを使用して塗布した。塗布後、窒素雰囲気下、紫外LED(Phoseon Technology社製 RX Firefly、中心波長 395nm、照射強度1.0w/cm2)を用いて5秒間光照射したところ、硬化していることを確認した。得られた光硬化物の屈折率はnD=1.535であった。
トリメチロールプロパントリアクリレート100重量部、合成実施例4と同様の方法で合成した4−[(ジフェノキシホスホリル)オキシ]−1−ナフチルメタクリレート50重量部に対し、光ラジカル重合開始剤イルガキュア819(ビー・エー・エス・エフ社製)を1重量部添加し光ラジカル重合性組成物を調製した。次に、ポリエステルフィルム(東レ製ルミラー膜厚100ミクロン、ルミラーは東レ株式会社の登録商標)上に調製した組成物を膜厚が100ミクロンとなるようにバーコーターを使用して塗布した。塗布後、窒素雰囲気下、紫外LED(Phoseon Technology社製 RX Firefly、中心波長 395nm、照射強度1.0w/cm2)を用いて5秒間光照射したところ、硬化していることを確認した。得られた光硬化物の屈折率はnD=1.548であった。
4−[(ジエトキシホスホリル)オキシ]−1−ナフチルメタクリレートを0部、トリメチロールプロパントリアクリレートを100部とした以外は、評価実施例1と同様に行ったところ、10秒でベタつきが無くなり硬化した。得られた重合物の屈折率は1.512であった。
Claims (4)
- 一般式(1)で示される4−[(ジ置換ホスホリル)オキシ]−1−ナフチルメタクリレート化合物。
(一般式(1)中、R3は水素原子又はメチル基を示し、R1、R2は同一であっても異なっていても良く、炭素数1以上4以下のアルキル基又は炭素数6もしくは7のアリール基のいずれかを示し、X、Yは同一であっても異なっていてもよく、水素原子又は炭素数1以上8以下のアルキル基のいずれかを示す。) - 請求項1に記載の一般式(1)で示される4−[(ジ置換ホスホリル)オキシ]−1−ナフチルメタクリレート化合物、及びラジカル重合開始剤を含有するラジカル重合性組成物。
- 請求項2に記載のラジカル重合性組成物を重合してなる重合物。
- 一般式(2)に示すジ置換−4−ヒドロキシ−1−ナフチルホスフェート化合物を(メタ)アクリロイル化することよりなる請求項1に記載の4−[(ジ置換ホスホリル)オキシ]−1−ナフチル(メタ)アクリレート化合物の製造方法。
(一般式(2)中、R1、R2は同一であっても異なっていてもよく、炭素数1以上4以下のアルキル基もしくは炭素数6又は7のアリール基のいずれかを示し、X、Yは同一であっても異なっていてもよく、水素原子又は炭素数1以上8以下のアルキル基のいずれかを示す。)
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