JP6179874B2 - 新規なリン置換ジヒドロキシナフタレン化合物及びその製造法 - Google Patents
新規なリン置換ジヒドロキシナフタレン化合物及びその製造法 Download PDFInfo
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- -1 phosphorus-substituted dihydroxynaphthalene compound Chemical class 0.000 title claims description 72
- 238000000034 method Methods 0.000 title description 4
- CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 claims description 34
- 239000003063 flame retardant Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- 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 claims description 24
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000000191 1,4-naphthoquinones Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 229930192627 Naphthoquinone Natural products 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical group CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 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 2
- 230000001771 impaired effect Effects 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- 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 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NHDJZQSOUDOKRS-UHFFFAOYSA-N 4-hydroxy-6-methoxynaphthalene-1,2-dione Chemical compound O=C1C(=O)C=C(O)C2=CC(OC)=CC=C21 NHDJZQSOUDOKRS-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- HGAZJKGZTZTKCO-UHFFFAOYSA-N C12=CC=CC=C2OP(=O)=C2C1=CCCC2 Chemical compound C12=CC=CC=C2OP(=O)=C2C1=CCCC2 HGAZJKGZTZTKCO-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000018380 Chemical injury Diseases 0.000 description 1
- ZJPOEIQBAPCMMA-UHFFFAOYSA-N ClC1=CC=C2C(=O)C(O)=CC(=O)C2=C1 Chemical compound ClC1=CC=C2C(=O)C(O)=CC(=O)C2=C1 ZJPOEIQBAPCMMA-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XUCVMOFAXIVYME-UHFFFAOYSA-N O=C1C(O)=CC(=O)C2=CC(C)=CC=C21 Chemical compound O=C1C(O)=CC(=O)C2=CC(C)=CC=C21 XUCVMOFAXIVYME-UHFFFAOYSA-N 0.000 description 1
- GYNUEBLEZDPNRP-UHFFFAOYSA-N OC1=CC(=O)C2=C(C=CC(Br)=C2)C1=O Chemical compound OC1=CC(=O)C2=C(C=CC(Br)=C2)C1=O GYNUEBLEZDPNRP-UHFFFAOYSA-N 0.000 description 1
- YFJKEBQQYZPKRK-UHFFFAOYSA-N OC=1C(C2=CC=C(C=C2C(C=1)=O)CC)=O Chemical compound OC=1C(C2=CC=C(C=C2C(C=1)=O)CC)=O YFJKEBQQYZPKRK-UHFFFAOYSA-N 0.000 description 1
- UJCJISYUYYZBTH-UHFFFAOYSA-N OC=1C(C2=CC=C(C=C2C(C=1)=O)OCC)=O Chemical compound OC=1C(C2=CC=C(C=C2C(C=1)=O)OCC)=O UJCJISYUYYZBTH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000002743 phosphorus functional group Chemical group 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N tetrabromobisphenol-F Natural products C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Fireproofing Substances (AREA)
Description
これらのリン置換ジヒドロキシナフタレン化合物は、下記反応式に示したように、一般式(4)で表される2−ヒドロキシ−1,4−ナフトキノン化合物と式(5)で表される9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイドを反応させることにより位置異性体混合物として得ることができる。
で行う。反応温度が低すぎると実用的な反応速度が得られず、一方、温度が高すぎると高次副生物の生成が多くなるなどの不利を招く。
当該反応により得られたリン置換ジヒドロキシナフタレン化合物及びその位置異性体混合物は、エポキシ樹脂類の反応性難燃剤として用いることができる。すなわち、当該反応生成物に、エポキシ樹脂類を添加して反応を行うことにより、リン化合物中にエポキシ基を導入することができる。
(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)屈折率計:エルマーER−7MW−H
(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ECS400 FT NMR Spectorometer
(5)質量分析計:島津製作所社製質量分析計、型式GCMS−QP5000
反応容器に9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド(HCA)12.9g(59.7mmol)、溶媒の2−エトキシエタノール23.9g)を仕込んだ。次に、窒素ガス雰囲気中、油浴上で内温を70℃前後に保ち、2−ヒドロキシ−1,4−ナフトキノン10.0g(57.4mmol)を5回に分け、2時間で仕込んだ。その後油浴の温度を上げ、120℃前後に内温を保ちながら5時間撹拌した。室温に戻した後、溶媒の2−エトキシエタノールを減圧留去した。残留した固体にメタノール50gを加えて、室温で30分懸洗した。減圧濾過により固液分離を行い、メタノール20gで2回ケーキ洗浄を行った後、減圧乾燥を行うことによりリン置換ジヒドロキシナフタレン化合物19.3gを位置異性体の混合物として得た。粗収率は86.2モル%であった。
(1)融点:162−164℃
(2)屈折率:nD=1.692
(3)IR(KBr,cm−1):3320、1650、1590、1410、1310、1260、1240、1200、1160、1140、1080、990、950、910、750、710、600、520、430
(4)1H−NMR(400MHz、DMSO-d6):δ=6.58(s、1H)、7.17−8.22(m、12H)、9.85(s、1H)、10.13(s、1H)
(5)32P−NMR(400MHz、DMSO-d6):δ=8.41
(6)MS−スペクトル:M+=390
Claims (4)
- 一般式(1)、(2)若しくは(3)で示されるリン置換ジヒドロキシナフタレン化合物又はこれらの少なくとも二種以上からなる位置異性体混合物。
(一般式(1)、(2)及び(3)中、Xは水素原子、アルキル基、ハロゲン原子又はアルコキシ基のいずれかを示す。) - 一般式(4)で示される2−ヒドロキシ−1,4−ナフトキノン化合物と式(5)で示される9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイドを反応させることを特徴とする一般式(1)、(2)若しくは(3)で示されるリン置換ジヒドロキシナフタレン化合物又はこれらの少なくとも二種以上からなる位置異性体混合物の製造法。
(一般式(4)中、Xは水素原子、アルキル基、ハロゲン原子又はアルコキシ基のいずれかを示す。)
(一般式(1)、(2)及び(3)中、Xは水素原子、アルキル基、ハロゲン原子又はアルコキシ基のいずれかを示す。) - 2−ヒドロキシ−1,4−ナフトキノン化合物が2−ヒドロキシ−1,4−ナフトキノンであることを特徴とする請求項2に記載の製造法。
- 少なくとも一般式(1)、(2)又は(3)で示されるリン置換ジヒドロキシナフタレン化合物を含有する難燃化剤。
(一般式(1)、(2)及び(3)中、Xは水素原子、アルキル基、ハロゲン原子又はアルコキシ基のいずれかを示す。)
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JP2002128860A (ja) * | 2000-10-27 | 2002-05-09 | Dainippon Ink & Chem Inc | エポキシ樹脂の製造方法及びエポキシ樹脂組成物 |
JP5587542B2 (ja) * | 2008-02-01 | 2014-09-10 | 新日鉄住金化学株式会社 | リン含有エポキシ樹脂およびリン含有エポキシ樹脂組成物、その製造方法と該樹脂および該樹脂組成物を用いた硬化性樹脂組成物および硬化物 |
JP5823134B2 (ja) * | 2010-02-09 | 2015-11-25 | 丸菱油化工業株式会社 | 難燃性樹脂組成物 |
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