JP5607091B2 - 含フッ素マレイミド化合物及びその製造方法 - Google Patents
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- 229910052731 fluorine Inorganic materials 0.000 title claims description 57
- 239000011737 fluorine Substances 0.000 title claims description 55
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 54
- -1 maleimide compound Chemical class 0.000 title claims description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 24
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 22
- 229910052710 silicon Inorganic materials 0.000 claims description 21
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 9
- 125000000962 organic group Chemical class 0.000 claims description 8
- 238000007126 N-alkylation reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 150000002222 fluorine compounds Chemical class 0.000 description 6
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007100 recyclization reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
少なくとも一つのケイ素原子に結合した下記一般式(1)で示される残基を有するものであることを特徴とする含フッ素マレイミド化合物を提供する。
一分子中に、少なくとも一つのフルオロアルキル基及び/又はフルオロポリエーテル基を有し、少なくとも一つのケイ素原子を含み、塩素、臭素、及びヨウ素から選ばれるハロゲン原子により変性された有機基を有する含ハロゲン変性有機ケイ素化合物と、下記一般式(3)で示される化合物とをN−アルキル化反応させ、
得られた化合物を100℃以上に加熱することで前記含フッ素マレイミド化合物を得ることを特徴とする含フッ素マレイミド化合物の製造方法を提供する。
少なくとも一つのケイ素原子に結合した下記一般式(1)で示される残基を有するものである。
このような含ハロゲン変性有機ケイ素化合物として好ましいものとしては、以下のような化合物が挙げられる。
下記の化合物(5)20.0gと4−ブロモ−1−ブテン10.6g、m−キシレンヘキサフルオライド20gを、攪拌および還流装置を備えたフラスコ中で90℃に昇温し、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.040g(Pt単体として1.0×10−7モルを含有)を混合し、12時間加熱攪拌を継続した。加熱停止後に得られた混合溶液に活性炭1質量部を加え1時間攪拌した後に加圧ろ過を行った。ろ液から有機溶媒をエバポレーターで110℃/2Torrの条件で揮発させ、29.5gの淡黄色透明液体を得た。得られた液体は1H NMR、13C NMRから下記(6)の化合物であると同定した。
下記化合物(11)20.0gと4−ブロモ−1−ブテン13.5g、m−キシレンヘキサフルオライド20gを、攪拌および還流装置を備えたフラスコ中で90℃に昇温し、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.040g(Pt単体として1.0×10−7モルを含有)を混合し、12時間加熱攪拌を継続した。その後、反応溶液から、減圧留去により110℃/2Torrで揮発分を除去し、30.2gの淡黄色透明液体を得た。得られた液体は1H−NMR、13C−NMRから下記化合物(12)であると同定した。
下記化合物(15)20.0gと4−ブロモ−1−ブテン15.0g、m−キシレンヘキサフルオライド20gを、攪拌および還流装置を備えたフラスコ中で90℃に昇温し、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.040g(Pt単体として1.0×10−7モルを含有)を混合し、12時間加熱攪拌を継続した。その後、反応溶液から、減圧留去により110℃/2Torrで揮発分を除去し、33.4gの淡黄色透明液体を得た。得られた液体は1H−NMR、13C−NMRから下記化合物(16)であると同定した。
4−ブロモ−1−ブテンに替えて、3−ブロモ−1−プロペン9.52gを使用した以外は実施例1の(6)の合成方法と全く同一の手順で反応を行ったが、付加反応は進行せず、原料(5)がそのまま回収された。
化合物(5)20.0gと下記化合物(9)16.2g、m−キシレンヘキサフルオライド20gを、攪拌および還流装置を備えたフラスコ中で90℃に昇温し、塩化白金酸/ビニルシロキサン錯体のトルエン溶液0.040g(Pt単体として1.0×10−7モルを含有)を混合し、12時間加熱攪拌を継続した。反応溶液の1H NMRを測定したところ、目的とするアリル基への付加反応は進行しておらず、下記のような化合物(10)が生成しており、目的の化合物は得られなかった。
Claims (4)
- 一分子中に、少なくとも一つのフルオロアルキル基及び/又はフルオロポリエーテル基を有し、
少なくとも一つのケイ素原子に結合した下記一般式(1)で示される残基を有するものである含フッ素マレイミド化合物であって、
下記一般式(2)で示されるものであることを特徴とする含フッ素マレイミド化合物。
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JP2012039682A JP5607091B2 (ja) | 2012-02-27 | 2012-02-27 | 含フッ素マレイミド化合物及びその製造方法 |
TW102106599A TWI557132B (zh) | 2012-02-27 | 2013-02-25 | Fluorine-containing maleimide compound and method for producing the same |
CN201310060694.3A CN103288866B (zh) | 2012-02-27 | 2013-02-26 | 含氟马来酰亚胺化合物及其制造方法 |
KR1020130020357A KR101946071B1 (ko) | 2012-02-27 | 2013-02-26 | 불소 함유 말레이미드 화합물 및 그의 제조 방법 |
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KR (1) | KR101946071B1 (ja) |
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TW (1) | TWI557132B (ja) |
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JP2023077454A (ja) * | 2021-11-25 | 2023-06-06 | 信越化学工業株式会社 | イミド結合及び重合性不飽和結合含有環状オルガノシロキサン、及びそれを含む硬化性樹脂組成物 |
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JPH0796591B2 (ja) * | 1988-07-22 | 1995-10-18 | 信越化学工業株式会社 | フッ化ビニリデン系グラフト共重合体の製造方法 |
JP3281030B2 (ja) | 1992-05-08 | 2002-05-13 | 株式会社メニコン | 眼用レンズ材料 |
JPH0756125A (ja) * | 1993-08-11 | 1995-03-03 | Toray Ind Inc | コンタクトレンズ |
JP2000143983A (ja) * | 1998-11-06 | 2000-05-26 | Tomoegawa Paper Co Ltd | 回路積層材料 |
JP2000212189A (ja) * | 1999-01-18 | 2000-08-02 | Aisin Seiki Co Ltd | O―シリル化アリ―ルマレイミドの製造 |
US20060009578A1 (en) * | 2004-07-07 | 2006-01-12 | Dershem Stephen M | Compositions containing maleimide-substituted silsesquioxanes and methods for use thereof |
US7777064B2 (en) * | 2006-03-02 | 2010-08-17 | Designer Molecules, Inc. | Adhesive compositions containing cyclic siloxanes and methods for use thereof |
WO2007100329A1 (en) * | 2006-03-02 | 2007-09-07 | Designer Molecules, Inc. | Adhesive composition containing cyclic siloxanes |
US20100113643A1 (en) * | 2007-04-09 | 2010-05-06 | Designer Molecules, Inc. | Curatives for epoxy adhesive compositions |
CN102020846B (zh) * | 2010-09-29 | 2014-03-19 | 北京化工大学 | 糠胺型苯并噁嗪树脂/马来酰亚胺化合物组合物 |
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