JPH0316376B2 - - Google Patents

Info

Publication number: JPH0316376B2
Authority: JP; Japan
Prior art keywords: formula; mmol; palladium; triphenylphosphine; aromatic
Prior art date: 1987-11-09
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

Application number

JP28107787A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01123823A (ja

Inventor

Yoshio Imai

Masaaki Kakimoto

Masaru Yoneyama

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

TOKYO KOGYO DAIGAKUCHO

Original Assignee

TOKYO KOGYO DAIGAKUCHO

Priority date (The priority date 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 date listed.)

1987-11-09

Filing date

1987-11-09

Publication date

1991-03-05

1987-11-09 Application filed by TOKYO KOGYO DAIGAKUCHO filed Critical TOKYO KOGYO DAIGAKUCHO

1987-11-09 Priority to JP28107787A priority Critical patent/JPH01123823A/ja

1989-05-16 Publication of JPH01123823A publication Critical patent/JPH01123823A/ja

1991-03-05 Publication of JPH0316376B2 publication Critical patent/JPH0316376B2/ja

Status Granted legal-status Critical Current

Links

KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 46
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 26
229910002091 carbon monoxide Inorganic materials 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 24
229910052763 palladium Inorganic materials 0.000 claims description 24
239000004760 aramid Substances 0.000 claims description 12
229920003235 aromatic polyamide Polymers 0.000 claims description 12
239000011347 resin Substances 0.000 claims description 12
229920005989 resin Polymers 0.000 claims description 12
150000004984 aromatic diamines Chemical class 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
150000007530 organic bases Chemical class 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
-1 palladium halides Chemical class 0.000 claims description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 3
150000002941 palladium compounds Chemical class 0.000 claims description 2
150000003003 phosphines Chemical class 0.000 claims description 2
229920006122 polyamide resin Polymers 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical group C(CCC)N(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 58
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 21
239000004952 Polyamide Substances 0.000 description 20
238000000862 absorption spectrum Methods 0.000 description 20
229920002647 polyamide Polymers 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 17
239000000203 mixture Substances 0.000 description 13
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 6
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 6
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 6
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 6
YAWIAFUBXXPJMQ-UHFFFAOYSA-N 1-bromo-4-(4-bromophenoxy)benzene Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(Br)C=C1 YAWIAFUBXXPJMQ-UHFFFAOYSA-N 0.000 description 5
JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 4
PSHMTKQTHXXOKM-UHFFFAOYSA-N 2,5-bis(4-bromophenyl)-3,4-diphenylthiophene Chemical compound C1=CC(Br)=CC=C1C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC(Br)=CC=2)S1 PSHMTKQTHXXOKM-UHFFFAOYSA-N 0.000 description 4
KBVDUUXRXJTAJC-UHFFFAOYSA-N 2,5-dibromothiophene Chemical compound BrC1=CC=C(Br)S1 KBVDUUXRXJTAJC-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ALSVFJIXSNRBLE-UHFFFAOYSA-N 1-bromo-3-(3-bromophenoxy)benzene Chemical compound BrC1=CC=CC(OC=2C=C(Br)C=CC=2)=C1 ALSVFJIXSNRBLE-UHFFFAOYSA-N 0.000 description 1
BGPOVBPKODCMMN-UHFFFAOYSA-N 1-bromo-3-(4-bromophenoxy)benzene Chemical compound C1=CC(Br)=CC=C1OC1=CC=CC(Br)=C1 BGPOVBPKODCMMN-UHFFFAOYSA-N 0.000 description 1
IYOYOEKCRDEIPQ-UHFFFAOYSA-N 1-bromo-4-[(4-bromophenyl)methyl]benzene Chemical compound C1=CC(Br)=CC=C1CC1=CC=C(Br)C=C1 IYOYOEKCRDEIPQ-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
RZFOAVRHEGQZRV-UHFFFAOYSA-N 2,3-diphenylthiophene Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RZFOAVRHEGQZRV-UHFFFAOYSA-N 0.000 description 1
ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000004210 ether based solvent 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012770 industrial material Substances 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Polyamides (AREA)

JP28107787A 1987-11-09 1987-11-09 芳香族ポリアミド樹脂の製造方法 Granted JPH01123823A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP28107787A JPH01123823A (ja)	1987-11-09	1987-11-09	芳香族ポリアミド樹脂の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP28107787A JPH01123823A (ja)	1987-11-09	1987-11-09	芳香族ポリアミド樹脂の製造方法

Publications (2)

Publication Number	Publication Date
JPH01123823A JPH01123823A (ja)	1989-05-16
JPH0316376B2 true JPH0316376B2 (fr)	1991-03-05

Family

ID=17634002

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP28107787A Granted JPH01123823A (ja)	1987-11-09	1987-11-09	芳香族ポリアミド樹脂の製造方法

Country Status (1)

Country	Link
JP (1)	JPH01123823A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5210175A (en) *	1992-02-25	1993-05-11	Eastman Kodak Company	Preparation of aromatic polyamides from CO, aromatic, diamine and di(trifluoromethane sulfonate)
FR2847582B1 (fr) *	2002-11-22	2004-12-24	Rhodia Polyamide Intermediates	Procede de preparation de polyamide par carbonylation en presence d'un catalyseur
JP4557794B2 (ja) *	2005-05-16	2010-10-06	山本化成株式会社	チオフェンを主鎖に含む高分子化合物、および該化合物を含有する有機電界発光素子

1987
- 1987-11-09 JP JP28107787A patent/JPH01123823A/ja active Granted

Also Published As

Publication number	Publication date
JPH01123823A (ja)	1989-05-16

Legal Events

Date	Code	Title	Description
2004-08-02	S111	Request for change of ownership or part of ownership	Free format text: JAPANESE INTERMEDIATE CODE: R313111
2004-08-10	R350	Written notification of registration of transfer	Free format text: JAPANESE INTERMEDIATE CODE: R350
2007-11-09	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US4713438A (en)	1987-12-15	Amide and/or imide containing polymers and monomers for the preparation thereof
JP2638981B2 (ja)	1997-08-06	芳香族ポリエステル樹脂の製造方法
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JP2759796B2 (ja)	1998-05-28	新規なビス（マレイミド）シロキサンおよびその製造方法
US5243010A (en)	1993-09-07	Aromatic polyamide containing pendant silyl groups
JPH0316376B2 (fr)	1991-03-05
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Ueda et al.	1994	Synthesis of poly (amide-imide) s by palladium-catalysed polycondensation of aromatic dibromides contáining imide
Ueda et al.	1995	Synthesis and characterization of aramids containing a-terthienylene units by palladium-catalysed polycondensation of dibromo-a-terthiophene, aromatic diamines and carbon monoxide
JPH0315930B2 (fr)	1991-03-04
JPS63156828A (ja)	1988-06-29	新規な重縮合物
JPS6254813B2 (fr)	1987-11-17
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