JP5328006B2 - イミド−リンクしたマレインイミドおよびポリマレインイミド化合物 - Google Patents
イミド−リンクしたマレインイミドおよびポリマレインイミド化合物 Download PDFInfo
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- JP5328006B2 JP5328006B2 JP2006513422A JP2006513422A JP5328006B2 JP 5328006 B2 JP5328006 B2 JP 5328006B2 JP 2006513422 A JP2006513422 A JP 2006513422A JP 2006513422 A JP2006513422 A JP 2006513422A JP 5328006 B2 JP5328006 B2 JP 5328006B2
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- 150000001875 compounds Chemical class 0.000 title abstract description 40
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title abstract description 22
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 28
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 22
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 abstract description 14
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 14
- 150000003923 2,5-pyrrolediones Chemical class 0.000 abstract description 9
- 150000001412 amines Chemical class 0.000 abstract description 8
- 150000008064 anhydrides Chemical class 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 4
- 230000005494 condensation Effects 0.000 abstract description 4
- 230000006872 improvement Effects 0.000 abstract description 4
- 238000010348 incorporation Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 92
- 239000000853 adhesive Substances 0.000 description 72
- 230000001070 adhesive effect Effects 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- -1 maleimide compound Chemical class 0.000 description 40
- 239000000758 substrate Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 150000003949 imides Chemical group 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 229940098779 methanesulfonic acid Drugs 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007822 coupling agent Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 229920001169 thermoplastic Polymers 0.000 description 9
- 239000004416 thermosoftening plastic Substances 0.000 description 9
- IMYZQPCYWPFTAG-UHFFFAOYSA-N Mecamylamine Chemical compound C1CC2C(C)(C)C(NC)(C)C1C2 IMYZQPCYWPFTAG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 7
- 229910000071 diazene Inorganic materials 0.000 description 7
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 7
- 238000004377 microelectronic Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 0 CCC(CC)(CC(C(CC1)=O)C1=O)*N(C(CC1)=O)C1=O Chemical compound CCC(CC)(CC(C(CC1)=O)C1=O)*N(C(CC1)=O)C1=O 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229910002804 graphite Inorganic materials 0.000 description 5
- 239000010439 graphite Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 4
- VZUHQRBBQSLSHS-SSZFMOIBSA-N Isoimide Chemical compound C1=CC(Br)=CC=C1\N=C/1C(CCCC2)=C2C(=O)O\1 VZUHQRBBQSLSHS-SSZFMOIBSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000011231 conductive filler Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229920005603 alternating copolymer Polymers 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BSBSDQUZDZXGFN-UHFFFAOYSA-N cythioate Chemical compound COP(=S)(OC)OC1=CC=C(S(N)(=O)=O)C=C1 BSBSDQUZDZXGFN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002893 slag Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 1
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- HWWFIBWWDPKWSI-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione 1,5-diaminoanthracene-9,10-dione Chemical compound NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)N)=O.NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)N HWWFIBWWDPKWSI-UHFFFAOYSA-N 0.000 description 1
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 1
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 1
- LNXVNZRYYHFMEY-UHFFFAOYSA-N 2,5-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C(Cl)=CC1=O LNXVNZRYYHFMEY-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- WQOWBWVMZPPPGX-UHFFFAOYSA-N 2,6-diaminoanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 WQOWBWVMZPPPGX-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- OJSPYCPPVCMEBS-UHFFFAOYSA-N 2,8-dimethyl-5,5-dioxodibenzothiophene-3,7-diamine Chemical compound C12=CC(C)=C(N)C=C2S(=O)(=O)C2=C1C=C(C)C(N)=C2 OJSPYCPPVCMEBS-UHFFFAOYSA-N 0.000 description 1
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- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- GTIBACHAUHDNPH-WHYMJUELSA-N n,n'-bis[(z)-benzylideneamino]oxamide Chemical compound C=1C=CC=CC=1\C=N/NC(=O)C(=O)N\N=C/C1=CC=CC=C1 GTIBACHAUHDNPH-WHYMJUELSA-N 0.000 description 1
- KQYREKISXCBRQB-UHFFFAOYSA-N n,n-diethylethanamine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCN(CC)CC KQYREKISXCBRQB-UHFFFAOYSA-N 0.000 description 1
- KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000005254 oxyacyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- VPRFQZSTJXHBHL-UHFFFAOYSA-N phenanthrene-9,10-diamine Chemical compound C1=CC=C2C(N)=C(N)C3=CC=CC=C3C2=C1 VPRFQZSTJXHBHL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- JGMHZIHMNAXXPH-UHFFFAOYSA-N tert-butyl 2-[[1-(2-amino-1,3-thiazol-4-yl)-2-diethoxyphosphinothioyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)ON=C(C(=O)OP(=S)(OCC)OCC)C1=CSC(N)=N1 JGMHZIHMNAXXPH-UHFFFAOYSA-N 0.000 description 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L79/085—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09J179/085—Unsaturated polyimide precursors
Description
本出願は、2003年5月5日に出願された出願番号60/468,037号に基づく優先権を主張し、その内容は本明細書において参照され、その一部とされる。
本発明の技術分野
本発明の背景
発明の要約
RとQは、各々独立して、置換または非置換の、脂肪族、芳香族、ヘテロ芳香族、またはシロキサン部位であり;
また、nは1から約10である、ただしイミド延長されたビスマレインイミドは以下のものではない。
R2は置換または非置換の、脂肪族、芳香族またはシロキサンである。
R3は、置換または非置換の脂肪族、芳香族、ヘテロ芳香族、またはシロキサン部位である。
R4は置換または非置換の直鎖、分岐または環状の、2から約100の炭素原子を有する脂肪族部位、または置換または非置換の芳香族部位である。
a) 上記のモノマレインイミド、ビスマレインイミドあるいはポリマレインイミド化合物の少なくとも1つ、またはそれらの組み合わせを、組成物の全重量に基づいて2重量%(wt%)から約98重量%;
b) 伝導性フィラー0から約90重量%;
d) 少なくとも1つの硬化開始剤を組成物の全重量に基づいて0.1重量%から約5重量%;
e) 少なくとも1つのカップリング剤を組成物の全重量に基づいて0.1重量%から約4重量%。
そのような方法は、たとえば、以下の方法により行うことができる。
a.イミド延長されたモノ−、ビス−あるいはポリマレインイミドを含む接着性組成物の提供;および
b.円形に形作られた形状を介して接着性の組成物を押し出して、それにより接着性のロープを形成すること。
図面の簡単な説明
発明の詳細な説明
RとQは、各々独立して、置換または非置換の、脂肪族、芳香族、ヘテロ芳香族、またはシロキサン部位であり; また、nは1から約10である、ただしイミド延長されたビスマレインイミドは以下のものではない。
第1工程は、ジアンハイドライドとダイマージアミンとの縮合によりアミン末端ポリイミドを形成することを含んでいる。
ジアミンは少なくとも若干過剰に存在し、イミド結合されたジアミン中間体を形成する必要がある。
1,10−ジアミノデカン;1,12−ジアミノドデカン;ダイマージアミン;1,2−ジアミノ−2−メチルプロパン;1,2−ジアミノシクロヘキサン;1,2−ジアミノプロパン;1,3−ジアミノプロパン;1,4−ジアミノブタン;1,5−ジアミノペンタン;1,7−ジアミノヘプタン;1,8−ジアミノメンタン;1,8−ジアミノオクタン;1,9−ジアミノノナン;3,3’−ジアミノ−N−メチルジプロピルアミン;ジアミノマレオニトリル;1,3−ジアミノペンタン;9,10−ジアミノフェナントレン;4,4’−ジアミノオクタフルオロビフェニル;3,5−ジアミノ安息香酸;3,7−ジアミノ−2−メトキシフルオレン;4,4’−ジアミノベンゾフェノン;3,4−ジアミノベンゾフェノン;3,4−ジアミノトルエン;2,6−ジアミノアントラキノン;2,6−ジアミノトルエン;2,3−ジアミノトルエン;1,8−ジアミノナフタレン;2,4−ジアミノトルエン;2,5−ジアミノトルエン;1,4−ジアミノアントラキノン;1,5−ジアミノアントラキノン;1,5−ジアミノナフタレン;1,2−ジアミノアントラキノン;2,4−クメンジアミン;1,3−ビスアミノメチルベンゼン;1,3−ビスアミノメチルシクロヘキサン;2−クロロ−1,4−ジアミノベンゼン;1,4−ジアミノ−2,5−ジクロロベンゼン;1,4−ジアミノ−2,5−ジメチルベンゼン;4,4’−ジアミノ−2,2’―ビストリフルオロメチルビフェニル;ビス(アミノ−3−クロロフェニ)エタン;ビス(4−アミノ−3,5−ジメチルフェニル)メタン;ビス(4−アミノ−3,5−ジエチルフェニル)メタン;ビス(4−アミノ−3−エチルジアミノフルオレン;ジアミノ安息香酸;2,3−ジアミノナフタレン;2,3−ジアミノフェノール;−5−メチルフェニル)メタン;ビス(4−アミノ−3−メチルフェニル)メタン;ビス(4−アミノ−3−エチルフェニル)メタン;4,4’−ジアミノフェニルスルホン;3,3’−ジアミノフェニルスルホン;2,2−ビス(4,(4アミノフェノキシ)フェニル)スルホン;2,2−ビス(4−(3−アミノフェノキシ)フェニル)スルホン;4,4’―オキシジアニリン;4,4’−ジアミノジフェニルスルフィド;3,4’−オキシジアニリン;2,2−ビス(4−(4−アミノフェノキシ)フェニル)プロパン;1,3−ビス(4−アミノフェノキシ)ベンゼン;4,4’−ビス(4−アミノフェノキシ)ビフェニル;4,4’−ジアミノ−3,3’−ジヒドロキシビフェニル;4,4’−ジアミノ−3,3’―ジメチルビフェニル;4,4’−ジアミノ−3,3’−ジメトキシビフェニル;Bisaniline M;Bisaniline P;9,9−ビス(4−アミノフェニル)フルオレン;o‐トリジンスルホン;メチレンビス(アントラニル酸);1,3−ビス(4−アミノフェノキシ)−2,2−ジメチルプロパン;1,3−ビス(4−アミノフェノキシ)プロパン;1,4−ビス(4−アミノフェノキシ)ブタン;1,5−ビス(4−アミノフェノキシ)ブタン;2,3,5,6−テトラメチル−1,4−フェニレンジアミン;3,3’,5,5’−テトラメチルベンジジン;4,4’−ジアミノベンザニリド;2,2−ビス(4−アミノフェニル)ヘキサフルオロプロパン;ポリオキシアルキレンジアミン類(たとえば、Huntsmanの Jeffamine D−230、D400、D−2000およびD−4000);1,3−シクロヘキサンビス(メチルアミン);m−キシリレンジアミン;p−キシリレンジアミン;ビス(4−アミノ−3−メチルシクロヘキシル)メタン;1,2−ビス(2−アミノエトキシ)エタン;3(4),8(9)−ビス(アミノメチル)トリシクロ(5.2.1.02,6)デカン;なとがあげられる。
ポリブタジエン−グラフト−無水マレイン酸;ポリエチレン−グラフト−無水マレイン酸;ポリエチレン−無水マレイン酸交互共重合体;ポリ無水マレイン酸−1−オクタデセン交互共重合体;ポリプロピレン−グラフト−無水マレイン酸;ポリ(スチレン−コ−無水マレイン酸);無水ピロメリト酸;無水マレイン酸、無水コハク酸;1,2,3,4−シクロブタンテトラカルボン酸二無水物;1,4,5,8−ナフタレンテトラカルボン酸二無水物;3,4,9,10−ペリレンテトラカルボン酸二無水物;ビシクロ(2.2.2)オクト−7−エン−2,3,5,6−テトラカルボン酸二無水物;ジエチレントリアミンペンタ酢酸二無水物;エチレンジアミン四酢酸二無水物;3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物;3,3’,4,4’−ビフェニルテトラカルボン酸二無水物;4,4’−オキシジフタリックス無水物;3,3’,4,4’−ジフェニルスルホンテトラカルボン酸二無水物;2,2’−ビス(3,4−ジカルボキシフェニル)ヘキサフルオロプロパン二無水物;4,4’−ビスフェノールA ジフタル酸無水物;5−(2,5−ジオキシテトラヒドロ)−3−メチル−3−シクロヘキセン−1,2−ジカルボン無水物;エチレングリコールビス(トリメリット酸無水物);ヒドロキノンジフタル酸無水物;アリルナディック酸無水物(allyl nadic anhydride);2−オクテン−1−イルコハク酸無水物;無水フタル酸;1,2,3,6−テトラヒドロフタル酸無水物;3,4,5,6−テトラヒドロフタル酸無水物;1,8−ナフタル酸無水物;グルタル酸無水物;ドデセニルコハク酸無水物;ヘキサデセニルコハク酸無水物;ヘキサヒドロフタル酸無水物;メチルヘキサヒドロフタル酸無水物;テトラデセニルコハク酸無水物;およびこれらの類似物があげられる。
R3は置換または非置換の脂肪族、芳香族、ヘテロ芳香族あるいはシロキサン部位である。
R4は、置換または非置換の直鎖、分岐鎖、または環状の、2から約100の炭素原子を有する脂肪族の部位、あるいは芳香族部位である。
a) 組成物の全重量に基づいて2重量%(wt%)から約98の重量%の、以下の構造を有するイミド延長されたビスマレインイミド:
RおよびQは各々独立して置換または非置換の、脂肪族、芳香族、ヘテロ芳香族あるいはシロキサン部位であり;
nは、1から約10であり、イミド延長されたビスマレインイミドは以下のものではない;
d) 組成物の全重量に基づいて0.1重量%から約5重量%の少なくとも1つの硬化開始剤;
e) 組成物の全重量に基づいて0.1重量%から約4重量%の少なくとも1つのカップリング剤。
更に、この方法は、接着剤の正確なポジショニングを容易にし、基体および周囲の作業領域の接着剤による望まれない汚染を低減する。これらの接着剤の熱可塑性の性質は、ダイアタッチに使用された従来のペースト接着剤と比較して、商用用途のために他の著しい長所を有する。本明細書において記述された材料は、ペースト接着剤に伝統的に使用された−40℃の冷凍貯蔵条件を要求しない。十分なインヒビターを含んでいる完全に配合されられた熱可塑性接着剤混合物は、性能を何ら損なうことなく、数か月の間室温ないし若干低い温度で保持することができる。この接着剤の熱可塑性の性質は、そのような貯蔵中に樹脂基体からのフィラーの沈降を更に防ぐ。
(a)第1の物品に上記接着性組成物を適用すること、
(b)第1の物品および第2の物品を緊密に接触させアセンブリを形成する、ここで、第1および第2の物品は(a)に適用された接着性組成物によってのみ隔てられる、そしてその後、
(c)アセンブリーを接着性組成物を硬化するのに適当な条件に暴露すること。
(a) 上記ダイアタッチペーストを基体および/またはマイクロエレクトロニックデバイスに適用すること、
(b)基体とデバイスを緊密に接触させアセンブリを形成する、ここで、基体とデバイスは(a)に適用されたダイアタッチ組成物によってのみ隔てられる、そしてその後、
(c)アセンブリーをダイアタッチ組成物が硬化するのに適当な条件に暴露すること。
イミド延長されたモノ−、ビス−およびポリマレインイミドの合成
実施例1
テフロンコーティングされた撹拌バーを装備した500mlの丸底フラスコに、250mlのトルエンを投入した。35g(0.35モル)のトリエチルアミンをフラスコに加え、ついで無水メタンスルホン酸35g(0.36モル)をゆっくりと加え、塩を形成した。ほぼ10分間撹拌して混合し、ついでVersamine 552(ダイマージアミン、Cognis社製)の57g(0.11モル)を加えた。無水ピロメリト酸(10.9g、0.05モル)を、撹拌された混合物にゆっくり加えた。ディーンスタークトラップとコンデンサーをフラスコに取り付けた。混合物を2時間還流に熱し、アミン末端のジイミドを形成した。この縮合からの水の理論的な量は、この時までに集められた。反応混合物は、室温以下に冷却され、無水マレイン酸の12.8g(0.13モル)がフラスコに加えられ、続いて無水メタンスルホン酸の5gを加えた。混合物は、さらに12時間還流され、期待された量の水を得た。室温に冷却された後、さらにトルエン100mlがフラスコに加えられた。また、混合物は沈殿された。溶液の上澄みを除去し、塩は追加のトルエン(2×100ml)ですすがれた。抽出物は一緒にされ、次に一晩沈殿され、追加の塩および酸が分離するのに十分な時間が提供された。溶液は、30gのシリカゲルがしっかりと詰められたガラスフリット漏斗を通してろ過された。溶剤を真空下で除去し、暗色のワックス状の樹脂60g(収率84%)を得た。
前の実施例において概説された方法と同様な方法により、38g(0.38モル)のトリエチルアミンと、250mlのトルエン中の無水メタンスルホン酸38g(0.39モル)を混合して、塩を形成した。Versamine 552の59g(0.11モル)をフラスコに加え、ついで3,3,’,4,4’−ベンゾフェノンテトラカルボン酸二無水物の16.1g(0.05モル)を、ゆっくりと加えた。混合物を約2時間還流し、水を共沸除去し、アミン末端のジイミドを形成した。反応混合物は、室温に冷却され、無水マレイン酸の12.5g(0.13モル)およびメタンスルホン酸の5gを加えた。混合物は、さらに12時間還流され、ビスマレインイミドを形成した。生成物は先の実施例に記載された手順により処理された。溶剤を完全に除去した後、暗い琥珀色の樹脂(65g、収率82%)を得た。
10g(0.10モル)のトリエチルアミンと、200mlのトルエン中のメタンスルホン酸11g(0.11モル)を混合して、塩を形成した。Versamine 552の32g(0.06モル)を混合物に加え、ついで1,1,3,3−テトラメチル−1,3−ビス(ノルボルニルジカルボン酸 無水物)ジシロキサンの13.5g(0.03モル)を、ゆっくりと加えた。水を共沸除去し、アミン末端のジイミドを形成した。これはほぼ1時間の還流を要した。反応混合物は冷却され、無水マレイン酸の10g(0.10モル)およびメタンスルホン酸の3gを加えた。混合物は、さらに18時間還流され、ディーンスタークトラップに必要な量の水を採取した。生成物は先の実施例に記載された手順により処理された。溶剤を除去した後、暗い琥珀色の樹脂として最終生成物(35g、収率73%)を得た。
40g(0.40モル)のトリエチルアミンと、200mlのトルエン中のメタンスルホン酸40g(0.42モル)を混合して、塩を形成した。Versamine 552の57g(0.11モル)と2,8−デカジエン−1,10−ジコハク酸無水物の17g(0.05モル)を、シーケンシャルに加えた。混合物を12時間還流し、水を共沸除去し、アミン末端のジイミドを形成した。反応混合物は室温に冷却され、無水マレイン酸の12.8g(0.13モル)およびメタンスルホン酸の5gをフラスコに加えた。混合物は、さらに一晩加熱され還流され、水を共沸除去した。生成物を処理し、琥珀色の樹脂65g(収率82%)を得た。
500mlのフラスコ中で35g(0.35モル)のトリエチルアミンと、250mlのトルエン中のメタンスルホン酸36g(0.37モル)を混合して、塩を形成した。
Versamine 552の90g(0.17モル)をフラスコに加え、ついで無水ピロメリト酸24g(0.11モル)を、ゆっくりと加えた。ほぼ2時間の還流の後、水を完全に共沸除去し、アミン末端のジイミドを形成した。反応混合物は室温に冷却され、無水マレイン酸の13g(0.13モル)およびメタンスルホン酸の10gを加えた。混合物は、再度12時間還流され、イミド−リンクされたビスマレインイミドが生成された。生成物は先の実施例に記載された手順により処理された。溶剤を完全に除去した後、暗い琥珀色の樹脂(100g、収率82%)を得た。
1リットルのフラスコ中で50g(0.50モル)のトリエチルアミンと、400mlのトルエン中の無水メタンスルホン酸50g(0.52モル)を混合して、塩を形成した。ビス(アミノメチル)トリシクロ[5.2.1.2.6]デカンの33g(0.17モル)をフラスコに加え、ついで4,4’−ビスフェノール−A 二無水物42g(0.08モル)を、ゆっくりと加えた。ほぼ2時間の還流により水を完全に共沸除去し、アミン末端のジイミドを形成した。反応混合物は室温に冷却され、無水マレイン酸の22g(0.22モル)およびメタンスルホン酸の8gを加えた。混合物は、再度16時間還流され、イミド−リンクされたビスマレインイミドが生成された。生成物は先の実施例に記載された手順により処理された。溶剤を完全に除去した後、ガラス質の、淡黄色の固体80g(収率94%)を得た。
1リットルのフラスコ中で35g(0.35モル)のトリエチルアミンと、400mlのトルエン中の無水メタンスルホン酸36g(0.38モル)を混合して、塩を形成した。2,2’−ビス[4−(4−アミノフェノキシ)フェニル]プロバン42g(0.10モル)をフラスコに加え、ついで無水ピロメリト酸11g(0.05モル)を、ゆっくりと加えた。ほぼ2時間の還流により水を共沸除去し、所望のアミン末端のジイミドを形成した。反応混合物は室温に冷却され、無水マレイン酸の8g(0.08モル)およびメタンスルホン酸の8gを加えた。混合物は、再度6時間還流され、ビスマレインイミドが生成された。真空下での溶剤除去、ブフナー漏斗での水による固体の洗浄による塩および酸の除去からなる生成物の処理を行った。水のほとんどを除去するため、アセトンで最後のリンスを行った。生成物を浅いパンの上に広げ、ほぼ100℃でオーブン中で一晩乾燥された。乾燥後、細かな黄色の粉末(44g、収率86%)を得た。
1リットルのフラスコ中で35g(0.35モル)のトリエチルアミンと、400mlのトルエン中の無水メタンスルホン酸36g(0.38モル)を混合して、塩を形成した。ビスフェノールA 二無水物(32g、0.06モル)をフラスコに加え、ついでVersamine 552の16g(0.03モル)を加えた。混合物を室温で1時間撹拌した後、2,2’−ビス[4−(4−アミノフェノキシ)フェニル]プロバン24g(0.06モル)をフラスコに加えた。水の共沸除去を約20時間行い、所望のアミン末端のイミドを形成した。反応混合物は室温に冷却され、無水マレイン酸の10g(0.10モル)およびメタンスルホン酸の5gを加えた。混合物は、再度18時間還流され、イミド−延長されたビスマレインイミドが生成された。生成物は先の実施例に記載された手順により処理された。溶剤を除去した後、黄色の砕けやすいガラス質の固体60g(収率82%)を得た。
テフロンコーティングを施した撹拌バーを装備した500mlの丸底フラスコに、トルエンの100mlと共にエチレンジアミン24g(0.40モル)を投入した。8重量%の無水マレイン酸でグラフトされたポリブタジエン(RI130MA8、Sartomer社製)の100gをゆっくりと加えた。水および過剰のエチレンジアミンの共沸除去が12時間の還流により行なわれた。過剰のエチレンジアミンの除去は反応容器への蒸気の導入によって援助された。その後、トリエチルアミン−メタンスルホン酸の塩(25g)が、メタンスルホン酸の3gおよび無水マレイン酸の12g(0.12モル)とともに溶液に加えられた。水の共沸除去を12時間の間行い、ポリマレインイミドを形成した。生成物は先の実施例に記載された手順により処理された。琥珀色の粘ちゅうな液体樹脂を100g得た。
トルエン(350ml)が、テフロンをコーティングした撹拌バーを装備した1リットルの丸底フラスコに加えられた。トリエチルアミン、50g(約0.50モル)がフラスコに加えられ、ついで無水のメタンスルホン酸の50g(0.52モル)のをゆっくりと加えた。混合物を室温でほぼ10分間撹拌し、ついでVersamine 552(ダイマー ジアミン(Cognis社製))の90g(0.17モル)を加えた。混合物に、BPADA(4、4’−ビスフェノールA 二無水物、GEプラスチック)の41g(0.08モル)を加えた。ディーンスタークトラップとコンデンサーをフラスコに取り付け、混合物を還流に加熱した。およそ2時間の後、アミン末端ジイミドへの完全な転化に対応する量の水が採取された。混合物は、40℃以下に冷却され、粉砕された無水マレイン酸の22g(0.23モル、約20%過剰)がフラスコに加えられ、ついでさらに10gの無水メタンスルホン酸を加えた。混合物は、再度ゆっくりと加熱され、還流された。ディーンスタークトラップ中に期待される量の水を採取するまでに、ほぼ18時間の還流が必要であった。室温に冷却した後に、200mlの追加のトルエンがフラスコに加えられ;撹拌がこの時点で停止され、混合物は分離することを許容された。上部(トルエン溶液)のフラクションは、2リットルのエルレンマイヤーフラスコへ注意深くデカントされた。塩はトルエン(2×500ml)で洗浄され、そのすすぎ液もデカントされ、一緒にされた。一緒にされたトルエン溶液から、より多くの塩および酸が分離されるよう、十分な時間を与えるため、琥珀色の溶液は一晩沈殿された。その後、溶液は、65gのシリカゲルがしっかりと詰められたガラスフリット漏斗を通してろ過された。濾過後、シリカゲルは追加のトルエン100mlで洗浄された。トルエンを真空下で除去し、暗色の琥珀色の樹脂120g(収率約85%)を得た。
引っ張り接着試験が先の実施例からの生成物について行われた。試験樹脂に加えられた唯一の成分は2重量%のジクミルパーオキサイド開始剤であった。触媒された樹脂混合物は、アルミニウムスタッドに銅スラグを付けるために使用された。アルミニウムポストは、290ミルの接触ヘッド直径を有していた。銅スラグの寸法は1000×400×150ミルであった。触媒された樹脂混合物について、それぞれ10個の試験アセンブリが作られた。部材は200℃のオーブン中で30分間硬化された。部材はついで室温に冷却され、SebastianIII引っ張り試験機を使用して接着強度が測定された。試験混合物とともに対照の組成物について試験が行われた。対照混合物はダイマージアミン(すなわちVersamine 552)から誘導されたビスマレインイミドであり、2%のジクミルパーオキサイドで触媒された。
Claims (1)
- 無水ピロメリト酸とC36−アルキレンジアミンとの両末端がアミン基である反応生成物を、無水マレイン酸と縮合させて得られるビスマレインイミド。
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2004
- 2004-04-30 WO PCT/US2004/013204 patent/WO2004099331A2/en active Application Filing
- 2004-04-30 MX MXPA05012039A patent/MXPA05012039A/es active IP Right Grant
- 2004-04-30 US US10/835,911 patent/US7208566B2/en active Active
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- 2004-04-30 JP JP2006513422A patent/JP5328006B2/ja active Active
- 2004-04-30 CN CN2004800119195A patent/CN1784457B/zh active Active
- 2004-04-30 EP EP04750876A patent/EP1620495A4/en not_active Withdrawn
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KR20060009903A (ko) | 2006-02-01 |
CN1784457A (zh) | 2006-06-07 |
US7208566B2 (en) | 2007-04-24 |
EP1620495A4 (en) | 2006-06-14 |
CN1784457B (zh) | 2010-07-14 |
KR101179815B1 (ko) | 2012-09-04 |
KR20120064711A (ko) | 2012-06-19 |
US20040225026A1 (en) | 2004-11-11 |
MXPA05012039A (es) | 2006-05-31 |
EP1620495A2 (en) | 2006-02-01 |
TW200508284A (en) | 2005-03-01 |
JP2006526014A (ja) | 2006-11-16 |
JP2012117070A (ja) | 2012-06-21 |
WO2004099331A3 (en) | 2005-07-14 |
JP5562360B2 (ja) | 2014-07-30 |
JP2014194021A (ja) | 2014-10-09 |
WO2004099331A2 (en) | 2004-11-18 |
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