JPH0231516B2 - - Google Patents
Info
- Publication number
- JPH0231516B2 JPH0231516B2 JP57039921A JP3992182A JPH0231516B2 JP H0231516 B2 JPH0231516 B2 JP H0231516B2 JP 57039921 A JP57039921 A JP 57039921A JP 3992182 A JP3992182 A JP 3992182A JP H0231516 B2 JPH0231516 B2 JP H0231516B2
- Authority
- JP
- Japan
- Prior art keywords
- aminophenoxy
- minutes
- adhesive
- film
- polyimide
- 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.)
- Expired - Lifetime
Links
- 239000000853 adhesive Substances 0.000 claims description 12
- 230000001070 adhesive effect Effects 0.000 claims description 12
- 229920001721 polyimide Polymers 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000004642 Polyimide Substances 0.000 claims description 5
- 239000011888 foil Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000004427 diamine group Chemical group 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 239000011889 copper foil Substances 0.000 description 8
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- -1 m-aminophenoxy Chemical group 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-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
- 229930003836 cresol Natural products 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- BBRLKRNNIMVXOD-UHFFFAOYSA-N bis[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 BBRLKRNNIMVXOD-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VCFRAMZVMJTSDM-UHFFFAOYSA-N (1,2,2,3,3,3-hexafluoro-1-phenylpropyl)benzene Chemical compound C=1C=CC=CC=1C(F)(C(F)(F)C(F)(F)F)C1=CC=CC=C1 VCFRAMZVMJTSDM-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- JFEXPVDGVLNUSC-UHFFFAOYSA-N 3-(3-aminophenyl)sulfanylaniline Chemical compound NC1=CC=CC(SC=2C=C(N)C=CC=2)=C1 JFEXPVDGVLNUSC-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- BZXJAHGHOJFYRT-UHFFFAOYSA-N 3-[2-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)OC=2C=C(N)C=CC=2)=C1 BZXJAHGHOJFYRT-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 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 description 1
- 239000011521 glass Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000463 material Substances 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
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
- H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Structure Of Printed Boards (AREA)
Description
【発明の詳細な説明】
本発明はフレキシブル印刷回路用基板の製造法
に関する。特に耐熱性、可撓性、電気絶縁性、難
燃性のすぐれたフレキシブル印刷回路基板の製造
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method of manufacturing a flexible printed circuit board. In particular, the present invention relates to a method for manufacturing a flexible printed circuit board with excellent heat resistance, flexibility, electrical insulation, and flame retardancy.
現在、ポリイミドフイルムと銅箔とを接着剤を
用いてはり合せてフレキシブル印刷回路用基板を
製造しているが、ポリイミドフイルムは十分耐熱
性があるが、接着剤の耐熱性が悪いために、フレ
キシブル基板の熱的性質が不満足で、例えば半田
耐熱性はせいぜい280℃程度である。 Currently, flexible printed circuit boards are manufactured by gluing polyimide film and copper foil together using an adhesive. Although the polyimide film has sufficient heat resistance, the adhesive has poor heat resistance, making it difficult to manufacture flexible printed circuit boards. The thermal properties of the board are unsatisfactory; for example, the solder heat resistance is only about 280°C at most.
そこで、耐熱性のすぐれた接着剤が要望されて
おり本発明は上述の欠点に鑑みてなされたもので
ある。 Therefore, there is a need for an adhesive with excellent heat resistance, and the present invention was made in view of the above-mentioned drawbacks.
即ち、本発明の特徴は耐熱性のすぐれた接着剤
にある。本発明の接着剤の化学構造を一般式で表
わせば
である。ここでＸはＯ、SO2、Ｓ、CO、CH2、
Ｃ（CH3）2及びＣ（CF3）2からなる群から選ばれる
二価の基であり、それぞれのＸは同じであつても
異なつていてもよく、R1及びR3はテトラカルボ
ン酸残基、R2はジアミン残基、ｘ＋ｙ＝１とす
るとｘは１〜0.2、ｙは０〜0.8であり、ｎは正数
であり、４個のベンゼン環に結合している３個の
Ｘ、Ｎ及び結合は互いにメタ−位又はパラ−位の
位置にある。また、芳香族環に結合されている水
素は他の不活性基で置換されていてもよい。 That is, the feature of the present invention is an adhesive having excellent heat resistance. The chemical structure of the adhesive of the present invention can be expressed as a general formula: It is. Here, X is O, SO 2 , S, CO, CH 2 ,
A divalent group selected from the group consisting of C(CH 3 ) 2 and C(CF 3 ) 2 , each X may be the same or different, and R 1 and R 3 are tetracarboxylic. An acid residue, R 2 is a diamine residue, x + y = 1, then x is 1 to 0.2, y is 0 to 0.8, n is a positive number, and the three atoms bonded to the four benzene rings are X, N and the bond are in meta- or para-positions with respect to each other. Furthermore, hydrogen bonded to the aromatic ring may be substituted with another inert group.
本発明に用いられる前記ポリイミドは有機溶媒
に可溶であり、一般式
であらわされるジアミン（ただし、該一般式中、
Ｘは前記と同じであり、４個のベンゼン環に結合
している３個のＸ及び２個のアミノ基は互いにメ
タ−位又はパラ−位の位置にある）とテトラカル
ボン酸無水物とを必要に応じて通常のジアミンを
加えて加熱反応させることにより製造される。 The polyimide used in the present invention is soluble in organic solvents and has the general formula Diamine represented by (however, in the general formula,
X is the same as above, and the three Xs and two amino groups bonded to the four benzene rings are at meta- or para-positions with respect to each other) and tetracarboxylic acid anhydride. It is manufactured by adding a normal diamine as needed and carrying out a heating reaction.
一般式
で表わされるジアミンの具体例としては４，4′−
ジ（ｍ−アミノフエノキシ）ジフエニルスルホ
ン、４，4′−ジ（Ｐ−アミノフエノキシ）ジフエ
ニルスルホン、４，4′−ジ（ｍ−アミノフエノキ
シ）ジフエニルエーテル、４，4′−ジ（Ｐ−アミ
ノフエノキシ）ジフエニルエーテル、４，4′−ジ
（ｍ−アミノフエノキシ）ジフエニルプロパン、
４，4′−ジ（Ｐ−アミノフエノキシ）ジフエニル
プロパン、４，4′−ジ（ｍ−アミノフエニルスル
ホニル）ジフエニルエーテル、４，4′−ジ（Ｐ−
アミノフエニルスルホニル）ジフエニルエーテ
ル、４，4′−ジ（ｍ−アミノフエニルチオエーテ
ル）ジフエニルスルフイド、４，4′−ジ（Ｐ−ア
ミノフエニルチオエーテル）ジフエニルスルフイ
ド、４，4′−ジ（ｍ−アミノフエノキシ）ジフエ
ニルケトン、４，4′−ジ（Ｐ−アミノフエノキ
シ）ジフエニルケトン、４，4′−ジ（ｍ−アミノ
フエノキシ）ジフエニルメタン、４，4′−ジ（Ｐ
−アミノフエノキシ）ジフエニルメタン、４，
4′−ジ（Ｐ−アミノフエノキシ）ジフエニルヘキ
サフルオロプロパン等がある。 general formula A specific example of the diamine represented by is 4,4'-
Di(m-aminophenoxy) diphenyl sulfone, 4,4'-di(P-aminophenoxy) diphenyl sulfone, 4,4'-di(m-aminophenoxy) diphenyl ether, 4,4'-di(P-aminophenoxy) ) diphenyl ether, 4,4'-di(m-aminophenoxy)diphenylpropane,
4,4'-di(P-aminophenoxy)diphenylpropane, 4,4'-di(m-aminophenylsulfonyl)diphenyl ether, 4,4'-di(P-
Aminophenyl sulfonyl) diphenyl ether, 4,4'-di(m-aminophenylthioether) diphenyl sulfide, 4,4'-di(P-aminophenyl thioether) diphenyl sulfide, 4 , 4'-di(m-aminophenoxy) diphenyl ketone, 4,4'-di(P-aminophenoxy) diphenyl ketone, 4,4'-di(m-aminophenoxy) diphenylmethane, 4,4'-di(P
-aminophenoxy)diphenylmethane, 4,
Examples include 4'-di(P-aminophenoxy)diphenylhexafluoropropane.
テトラカルボン酸ジ無水物としては３，3′，
４，4′−ベンゾフエノンテトラカルボン酸ジ無水
物、ピロメリト酸無水物、３，3′，４，4′−ジフ
エニルテトラカルボン酸ジ無水物、２，３，６，
７−ナフタリンテトラカルボン酸ジ無水物、１，
４，５，８−ナフタリンテトラカルボン酸ジ無水
物、４，4′−スルホニルジフタル酸無水物、３，
3′，４，4′−ジフエニルエーテルテトラカルボン
酸ジ無水物、シクロペンタンテトラカルボン酸ジ
無水物、ブタンテトラカルボン酸ジ無水物、エチ
レンビストリメリテートジ無水物などがある。 The tetracarboxylic dianhydride is 3,3′,
4,4'-benzophenonetetracarboxylic dianhydride, pyromellitic anhydride, 3,3',4,4'-diphenyltetracarboxylic dianhydride, 2,3,6,
7-naphthalene tetracarboxylic dianhydride, 1,
4,5,8-naphthalenetetracarboxylic dianhydride, 4,4'-sulfonyl diphthalic anhydride, 3,
Examples include 3',4,4'-diphenyl ether tetracarboxylic dianhydride, cyclopentane tetracarboxylic dianhydride, butane tetracarboxylic dianhydride, and ethylene bistrimelitate dianhydride.
また併用できる通常のジアミンとしては４，
4′−ジアミノジフエニルエーテル、４，4′−ジア
ミノジフエニルメタン、４，4′−ジアミノジフエ
ニルスルホン、３，3′−ジアミノジフエニルスル
ホン、メタフエニレンジアミン、パラフエニレン
ジアミン、４，4′−ジアミノジフエニルプロパ
ン、４，4′−ジアミノジフエニルスルフイド、
１，５−ジアミノナフタリン、２，６−ジアミノ
ナフタリン、２，６−ジアミノピリジン、１，４
−ジ（Ｐ−アミノフエノキシ）ベンゼン、１，３
−ジ（Ｐ−アミノフエノキシ）ベンゼンなどがあ
る。 Also, common diamines that can be used in combination include 4,
4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, metaphenylenediamine, paraphenylenediamine, 4, 4'-diaminodiphenylpropane, 4,4'-diaminodiphenyl sulfide,
1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 2,6-diaminopyridine, 1,4
-di(P-aminophenoxy)benzene, 1,3
-di(P-aminophenoxy)benzene and the like.
本発明のポリイミドを溶解する溶媒としてはク
レゾール、オルトクロルフエノール、Ｐ−クロル
フエノール、Ｐ−ブロムフエノール、２，４−ジ
クロルフエノール、２，４，６−トリクロルフエ
ノール、ニトロベンゼン、フエノール、スルホラ
ン、メチルスルホラン、ジメチルスルホキシド、
トリフルオロ酢酸、キシレノール、Ｎ−メチル−
２−ピロリドン、Ｎ，Ｎ−ジメチルアセトアミ
ド、Ｎ，Ｎ−ジメチルホルムアミド、ヘキサメチ
ルホスホルアミド等を用いることができる。 Solvents for dissolving the polyimide of the present invention include cresol, orthochlorophenol, P-chlorophenol, P-bromophenol, 2,4-dichlorophenol, 2,4,6-trichlorophenol, nitrobenzene, phenol, sulfolane, methyl Sulfolane, dimethyl sulfoxide,
Trifluoroacetic acid, xylenol, N-methyl-
2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, hexamethylphosphoramide, etc. can be used.
また、ポリイミド化する際に生成する水を共沸
により除去するためにトルエンやキシレンを用い
てもよい。 Furthermore, toluene or xylene may be used to azeotropically remove water produced during polyimidation.
前記一般式で示される接着剤は高温にすると架
橋し、有機溶媒に不溶となるものもあるが、さら
に、必要に応じて架橋剤を添加することもでき
る。架橋剤としてはイソシアネート化合物、マレ
イミド化合物などがある。 Some of the adhesives represented by the above general formula crosslink when exposed to high temperatures and become insoluble in organic solvents; however, a crosslinking agent may be added if necessary. Examples of crosslinking agents include isocyanate compounds and maleimide compounds.
接着剤の一般式においてｘは１〜0.2の範囲で
あるが、0.2よりも小さいと溶媒に対する溶解性
が悪くなる。ｎはＮ，Ｎ−ジメチルアセトアミド
中で0.1％の濃度で30℃で還元粘度を測定した場
合、還元粘度が0.1dl／ｇ以上になる数を示す。
この値以下だとフレキシブル基板としたときの可
撓性が悪くなる。 In the general formula of the adhesive, x is in the range of 1 to 0.2, but if it is smaller than 0.2, the solubility in the solvent will be poor. n indicates the number at which the reduced viscosity is 0.1 dl/g or more when measured at 30° C. at a concentration of 0.1% in N,N-dimethylacetamide.
If it is less than this value, the flexibility will be poor when used as a flexible substrate.
本発明には金属箔が必要であるが、一般に銅箔
やアルミニウム箔が用いられる。 Although the present invention requires a metal foil, copper foil or aluminum foil is generally used.
接着方法としては本発明の接着剤をポリイミド
フイルムに塗布した後、溶媒を加熱乾燥する。加
熱乾燥の条件は100〜300℃で30秒〜30分である。
この後、塗布、乾燥されたポリイミドフイルムと
銅箔を重ね、加熱、加圧することにより接着させ
てフレキシブル印刷回路用基板とする。 As for the bonding method, the adhesive of the present invention is applied to a polyimide film, and then the solvent is heated and dried. The heating drying conditions are 100 to 300°C for 30 seconds to 30 minutes.
Thereafter, the coated and dried polyimide film and copper foil are stacked and bonded together by heating and pressurizing to form a flexible printed circuit board.
さらに、本発明の接着剤から一旦フイルムを作
り、このフイルムをポリイミドフイルムと金属箔
の間にはさみ、加熱、加圧することにより接着さ
せてフレキシブル印刷回路用基板とすることも可
能である。 Furthermore, it is also possible to make a film from the adhesive of the present invention, sandwich this film between a polyimide film and a metal foil, and bond them by heating and pressurizing them to make a flexible printed circuit board.
以下に接着剤の製法及び実施例について説明す
る。 The manufacturing method and examples of the adhesive will be described below.
接着剤の製法
温度計、撹拌棒、リービツヒ冷却器、窒素ガス
導入管を備えた300mlの四口フラスコに、４，
4′−ジ（ｍ−アミノフエノキシ）ジフエニルスル
ホン16.2ｇ、３，3′，４，4′−ベンゾフエノンテ
トラカルボン酸二無水物12.075ｇ、クレゾール
200ｇ、トルエン40ｇを入れ170℃、５時間反応さ
せて水をトルエンと共に共沸により追い出した。
生成したポリイミド溶液の不揮発分は12.5％であ
つた。Adhesive manufacturing method 4,
4'-di(m-aminophenoxy)diphenylsulfone 16.2g, 3,3',4,4'-benzophenonetetracarboxylic dianhydride 12.075g, cresol
200g of toluene and 40g of toluene were added and reacted at 170°C for 5 hours, and water was expelled with toluene by azeotropy.
The nonvolatile content of the polyimide solution produced was 12.5%.
実施例 １
厚さ0.05mmのポリイミドフイルム（デユポン社
製カプトンフイルム）に上記により製造したワニ
スを塗布し、250℃で30分乾燥した。これと、
0.035mmの厚さの圧延銅箔を合せ、40Kg／cm2の圧
力で280℃、30分プレスした。作成したフレキシ
ブル基板のピール強度は1.6Kg／cmでポリイミド
基板が破断した。これを180℃で48時間熱劣化し
たもののピールは1.1Kg／cmであつた。また、350
℃、10分処理してもふくれの発生はなかつた。40
℃、湿度90％に24時間放置後の表面抵抗は３×
1012Ωであつた。Example 1 The varnish prepared above was applied to a polyimide film (Kapton Film, manufactured by DuPont) with a thickness of 0.05 mm, and dried at 250° C. for 30 minutes. This and
Rolled copper foils with a thickness of 0.035 mm were combined and pressed at 280° C. for 30 minutes at a pressure of 40 Kg/cm 2 . The peel strength of the created flexible substrate was 1.6 kg/cm, and the polyimide substrate broke. When this was heat aged at 180°C for 48 hours, the peel strength was 1.1 kg/cm. Also, 350
No blistering occurred even after treatment at ℃ for 10 minutes. 40
The surface resistance after being left at ℃ and 90% humidity for 24 hours is 3×
It was 10 12 Ω.
実施例 ２
実施例１で用いたワニスをガラス板上に流延
し、250℃、30分乾燥して厚さ25μのフイルムを
作成した。フイルムは可撓性のある丈夫なもので
あつた。Example 2 The varnish used in Example 1 was cast onto a glass plate and dried at 250°C for 30 minutes to form a film with a thickness of 25 μm. The film was flexible and strong.
このフイルムを35μの銅箔と50μのカプトンフ
イルムの間にはさみ、280℃、30分間プレスして
接着した。ピール強度は1.6Kg／cm以上であり、
耐熱性は350℃、10分でもふくれの発生はなかつ
た。 This film was sandwiched between a 35μ copper foil and a 50μ Kapton film and pressed at 280°C for 30 minutes to bond them together. Peel strength is 1.6Kg/cm or more,
Heat resistance was 350℃ and no blistering occurred even after 10 minutes.
実施例 ３
温度計、撹拌棒、リービツヒ冷却器および窒素
ガス導入管を備えた１の四口フラスコに４，
4′−ジ（ｍ−アミノフエノキシ）ジフエニルスル
ホン48.6ｇ、４，4′−ジアミノジフエニルエーテ
ル7.5ｇ、３，3′，４，4′−ベンゾフエノンテトラ
カルボン酸ジ無水物48.3ｇ、トリクレゾール750
ｇ、トルエン150ｇを入れ、窒素ガスを通じ、内
容物を撹拌しながら150℃で５時間反応させて均
一な溶液を得た。Example 3 4,
48.6 g of 4'-di(m-aminophenoxy) diphenyl sulfone, 7.5 g of 4,4'-diaminodiphenyl ether, 48.3 g of 3,3',4,4'-benzophenonetetracarboxylic dianhydride, cresol 750
150 g of toluene were added, nitrogen gas was passed through the solution, and the contents were reacted at 150° C. for 5 hours with stirring to obtain a homogeneous solution.
得られた溶液をカプトンフイルムに塗布し、
250℃で30分乾燥し、35μの厚さの銅箔を重ね、
300℃で30分プレスして接着した。得られたフレ
キシブル基板のピール強度は1.6Kg／cm以上であ
つた。また、350℃の半田に10分間浸漬してもふ
くれが生じなかつた。 Apply the resulting solution to Kapton film,
Dry at 250℃ for 30 minutes, layer with 35μ thick copper foil,
It was bonded by pressing at 300℃ for 30 minutes. The peel strength of the obtained flexible substrate was 1.6 kg/cm or more. In addition, no blistering occurred even when immersed in solder at 350°C for 10 minutes.
実施例 ４
温度計、撹拌棒、リービツヒ冷却器、窒素導入
管を備えた１の四口フラスコに、４，4′−ジ
（ｍ−アミノフエノキシ）ベンゾフエノン59.4ｇ、
３，3′，４，4′−ジフエニルエーテルテトラカル
ボン酸ジ無水物46.5ｇ、トリクレゾール750ｇ、
トルエン150ｇを入れて窒素ガスを通じながら、
150℃、５時間撹拌し、均一な溶液を得た。Example 4 59.4 g of 4,4'-di(m-aminophenoxy)benzophenone was placed in a four-necked flask equipped with a thermometer, stirring bar, Liebig condenser, and nitrogen inlet tube.
3,3',4,4'-diphenyl ether tetracarboxylic dianhydride 46.5g, tricresol 750g,
Add 150g of toluene and pass nitrogen gas through it.
Stirring was carried out at 150°C for 5 hours to obtain a homogeneous solution.
この溶液をカプトンフイルムに塗布し、250℃、
30分乾燥し、次に銅箔を重ねて280℃、30分プレ
スして接着させた。フレキシブル基板のピール強
度は1.6Kg／cm以上であつた。この基板は350℃の
半田に５分間浸漬してもふくれの発生はなかつ
た。 Apply this solution to Kapton film and heat at 250℃.
After drying for 30 minutes, copper foil was layered and pressed at 280°C for 30 minutes to adhere. The peel strength of the flexible substrate was 1.6 kg/cm or more. Even when this board was immersed in solder at 350°C for 5 minutes, no blistering occurred.
実施料 ５
実施例４と同様な装置に４，4′−ジ（ｍ−アミ
ノフエノキシ）ベンゾフエノン29.7ｇ、１，３−
ジ（ｍ−アミノフエノキシ）ベンゼン21.9ｇ、
４，4′−ヘキサフルオロイソプロピリデンビス
（フタル酸無水物）66.6ｇ、トリクレゾール750
ｇ、トルエン150ｇを入れ、窒素ガスを通じなが
ら150℃、５時間撹拌し、均一な溶液を得た。得
られた溶液をカプトンフイルムに塗布し、250℃、
30分乾燥し、次いで銅箔を重ね、280℃で30分間
プレスして接着させた。フレキシブル基板のピー
ル強度は1.6Kg／cm以上であり、350℃の半田浴に
５分間浸漬してもふくれの発生はなかつた。Practical material 5 Into the same apparatus as in Example 4, 29.7 g of 4,4'-di(m-aminophenoxy)benzophenone, 1,3-
21.9 g of di(m-aminophenoxy)benzene,
4,4'-hexafluoroisopropylidene bis(phthalic anhydride) 66.6g, tricresol 750
g, and 150 g of toluene were added thereto, and stirred at 150° C. for 5 hours while passing nitrogen gas to obtain a homogeneous solution. The obtained solution was applied to Kapton film and heated at 250℃.
After drying for 30 minutes, copper foil was layered and pressed at 280°C for 30 minutes to bond. The peel strength of the flexible substrate was 1.6 kg/cm or more, and no blistering occurred even after being immersed in a 350°C solder bath for 5 minutes.
Claims (1)
（CH3）2及びＣ（CF3）2からなる群から選ばれる二
価の基であり、それぞれのＸは同じであつても異
なつていてもよく、R1及びR3はテトラカルボン
酸残基、R2はジアミンの残基、ｘ＋ｙ＝１とす
るとｘは１〜0.2及びｙは０〜0.8であり、ｎは正
数であり、４個のベンゼン環に結合している３個
のＸ、Ｎ及び結合は互いにメタ−位又はパラ−位
の位置にある）で表わされるポリイミドを金属箔
とポリイミドフイルムの接着に用いることを特徴
とするフレキシブル印刷回路用基板の製造法。[Claims] 1. The following general formula as an adhesive: (Here, X is O, SO 2 , CO, S, CH 2 , C
A divalent group selected from the group consisting of (CH 3 ) 2 and C(CF 3 ) 2 , each X may be the same or different, and R 1 and R 3 are tetracarboxylic acid residue, R 2 is a diamine residue, x + y = 1, x is 1 to 0.2, y is 0 to 0.8, n is a positive number, and the three atoms bonded to the four benzene rings are 1. A method for manufacturing a flexible printed circuit board, characterized in that polyimide represented by X, N, and bonds are at meta- or para-positions) is used for bonding a metal foil and a polyimide film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3992182A JPS58157190A (en) | 1982-03-12 | 1982-03-12 | Method of producing substrate for flexible printed circuit |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3992182A JPS58157190A (en) | 1982-03-12 | 1982-03-12 | Method of producing substrate for flexible printed circuit |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58157190A JPS58157190A (en) | 1983-09-19 |
| JPH0231516B2 true JPH0231516B2 (en) | 1990-07-13 |
Family
ID=12566395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3992182A Granted JPS58157190A (en) | 1982-03-12 | 1982-03-12 | Method of producing substrate for flexible printed circuit |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58157190A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60243120A (en) * | 1984-05-18 | 1985-12-03 | Hitachi Ltd | Flexible printed base board and production thereof |
| JP2615002B2 (en) * | 1984-10-15 | 1997-05-28 | 三井東圧化学株式会社 | Heat resistant adhesive made of polyimide film |
| JP2610804B2 (en) * | 1984-10-15 | 1997-05-14 | 三井東圧化学株式会社 | Heat resistant adhesive made of polyimide film |
| JP2533841B2 (en) * | 1984-12-18 | 1996-09-11 | 三井東圧化学株式会社 | Heat resistant adhesive |
| US4883718A (en) * | 1985-02-12 | 1989-11-28 | Mitsui Toatsu Chemicals, Inc. | Flexible copper-clad circuit substrate |
| JPS627733A (en) * | 1985-03-10 | 1987-01-14 | Nitto Electric Ind Co Ltd | Colorless clear polyimide formed body and its production |
| US4725642A (en) * | 1985-04-29 | 1988-02-16 | E. I. Du Pont De Nemours And Company | Melt-fusible co-polyimide from diamine mixture |
| JPS61291669A (en) * | 1985-06-18 | 1986-12-22 | Mitsui Toatsu Chem Inc | Heat-resistant adhesive |
| JPH0678431B2 (en) * | 1985-07-15 | 1994-10-05 | 三菱油化株式会社 | Aromatic thioetherimide polymer |
| JP2587810B2 (en) * | 1985-10-11 | 1997-03-05 | 三井東圧化学株式会社 | Heat resistant adhesive made of polyimide |
| JPS6248782A (en) * | 1985-08-27 | 1987-03-03 | Mitsui Toatsu Chem Inc | Heat-resistant adhesive |
| EP0729995A1 (en) * | 1985-08-27 | 1996-09-04 | MITSUI TOATSU CHEMICALS, Inc. | Polyimide and high-temperature adhesive of polyimide |
| US5278276A (en) * | 1985-08-27 | 1994-01-11 | Mitsui Toatsu Chemicals, Incorporated | Polyimide and high-temperature adhesive of polyimide |
| US4716216A (en) * | 1985-08-30 | 1987-12-29 | General Electric Company | Crystalline polyimides containing cumulative phenylene sulfide units |
| EP0213573B1 (en) * | 1985-08-30 | 1991-11-21 | General Electric Company | Crystalline polyimides containing cumulative phenylene sulfide units |
| JPS6253388A (en) * | 1985-09-03 | 1987-03-09 | Mitsui Toatsu Chem Inc | Heat-resistant adhesive |
| JP2567375B2 (en) * | 1986-02-13 | 1996-12-25 | 三井東圧化学株式会社 | Colorless polyimide film |
| EP0234882B1 (en) * | 1986-02-25 | 1993-01-13 | MITSUI TOATSU CHEMICALS, Inc. | High-temperature adhesive of polyimide |
| JP2585552B2 (en) * | 1986-11-19 | 1997-02-26 | 三井東圧化学株式会社 | Polyimide |
| JPS63130633A (en) * | 1986-11-20 | 1988-06-02 | Kanegafuchi Chem Ind Co Ltd | Novel polyamic acid and production of polyimide |
| JP2519228B2 (en) * | 1987-01-08 | 1996-07-31 | 日東電工株式会社 | Colorless and transparent polyimide molding and method for producing the same |
| JPS64121A (en) * | 1987-02-13 | 1989-01-05 | New Japan Chem Co Ltd | Polyimide resin composition and its production |
| JPH0195155A (en) * | 1987-10-05 | 1989-04-13 | Mitsubishi Kasei Corp | Polyimide resin composition |
| JP2553110B2 (en) * | 1987-11-16 | 1996-11-13 | 三井東圧化学株式会社 | Method for producing polyimide with good moldability |
| JP2866654B2 (en) * | 1988-04-20 | 1999-03-08 | 日立化成工業株式会社 | Hot melt adhesive, polyimide film with hot melt adhesive layer, and printed circuit board |
| JPH0721442B2 (en) * | 1989-03-27 | 1995-03-08 | 日本電信電話株式会社 | Electron microscope sample preparation method and electron microscope sample preparation instrument |
| JP2890408B2 (en) * | 1988-05-10 | 1999-05-17 | 日立化成工業株式会社 | Hot melt adhesive, polyimide film with hot melt adhesive layer, and printed circuit board |
| KR910000832A (en) * | 1988-06-28 | 1991-01-30 | 랄프 챨스 메더스트 | Low dielectric constant and low moisture absorption polyimide and copolyimide for interlevel dielectric and substrate coatings |
| JP2536620B2 (en) * | 1989-05-31 | 1996-09-18 | 信越化学工業株式会社 | Method for producing polyimide resin |
| JP2536628B2 (en) * | 1989-08-02 | 1996-09-18 | 信越化学工業株式会社 | Composition for semiconductor device protection |
| JP2785394B2 (en) * | 1989-11-24 | 1998-08-13 | 宇部興産株式会社 | Thermoplastic aromatic polyimide |
| US5326643A (en) * | 1991-10-07 | 1994-07-05 | International Business Machines Corporation | Adhesive layer in multi-level packaging and organic material as a metal diffusion barrier |
| JPH05117596A (en) * | 1991-10-29 | 1993-05-14 | Sumitomo Bakelite Co Ltd | Film adhesive having high thermal conductivity and bondable by hot melt bonding |
| JPH05125332A (en) * | 1991-11-01 | 1993-05-21 | Sumitomo Bakelite Co Ltd | Hot melt bonding electrically conductive filmy adhesive |
| JPH05331424A (en) * | 1992-06-04 | 1993-12-14 | Sumitomo Bakelite Co Ltd | Film adhesive |
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| JP2672477B2 (en) * | 1995-03-20 | 1997-11-05 | 三井東圧化学株式会社 | Composition for polyimide resin |
| JP2593635B2 (en) * | 1995-03-20 | 1997-03-26 | 三井東圧化学株式会社 | Polyimide resin composition |
| JP2593634B2 (en) * | 1995-03-20 | 1997-03-26 | 三井東圧化学株式会社 | New polyimide resin composition |
| JP2593636B2 (en) * | 1995-04-17 | 1997-03-26 | 三井東圧化学株式会社 | Polyimide resin composition |
| JPH08225645A (en) * | 1995-12-18 | 1996-09-03 | Nitto Denko Corp | Colorless clear polyimide molding and production thereof |
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| JPS52153948A (en) * | 1976-06-15 | 1977-12-21 | Ciba Geigy Ag | Aromatic diamine polyamide compound consisting of said diamine and process for preparing same |
| JPS5518426A (en) * | 1978-07-27 | 1980-02-08 | Asahi Chem Ind Co Ltd | Heat-resistant flexible electronic parts |
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1982
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52153948A (en) * | 1976-06-15 | 1977-12-21 | Ciba Geigy Ag | Aromatic diamine polyamide compound consisting of said diamine and process for preparing same |
| JPS5518426A (en) * | 1978-07-27 | 1980-02-08 | Asahi Chem Ind Co Ltd | Heat-resistant flexible electronic parts |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58157190A (en) | 1983-09-19 |
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