CH623837A5 - - Google Patents
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- Publication number
- CH623837A5 CH623837A5 CH554675A CH554675A CH623837A5 CH 623837 A5 CH623837 A5 CH 623837A5 CH 554675 A CH554675 A CH 554675A CH 554675 A CH554675 A CH 554675A CH 623837 A5 CH623837 A5 CH 623837A5
- Authority
- CH
- Switzerland
- Prior art keywords
- solvent
- solution
- dianhydride
- polyimide
- ester
- Prior art date
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- 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 claims description 37
- -1 cyclic tricarboxylic acid Chemical class 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 229920001721 polyimide Polymers 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 29
- 239000004642 Polyimide Substances 0.000 claims description 28
- 239000002243 precursor Substances 0.000 claims description 24
- 125000005442 diisocyanate group Chemical group 0.000 claims description 22
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- 239000000047 product Substances 0.000 claims description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 150000005690 diesters Chemical class 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 3
- 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 2
- 239000007858 starting material Substances 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000004922 lacquer Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920005575 poly(amic acid) Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 5
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 125000006159 dianhydride group Chemical group 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- DVSOAVWCFVGQLO-UHFFFAOYSA-N bicyclo[2.2.2]oct-3-ene Chemical compound C1C(CC2)CCC2=C1 DVSOAVWCFVGQLO-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- KWNVKZXKQSYQLL-UHFFFAOYSA-N 1,3-dioxobenzo[e][2]benzofuran-6-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CC=CC2=C2C(=O)OC(=O)C2=C1 KWNVKZXKQSYQLL-UHFFFAOYSA-N 0.000 description 1
- XNFGDDFDPXGEGL-UHFFFAOYSA-N 1,3-dioxobenzo[f][2]benzofuran-6-carboxylic acid Chemical compound C1=C2C(=O)OC(=O)C2=CC2=CC(C(=O)O)=CC=C21 XNFGDDFDPXGEGL-UHFFFAOYSA-N 0.000 description 1
- KDLIYVDINLSKGR-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenoxy)benzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=C(N=C=O)C=C1 KDLIYVDINLSKGR-UHFFFAOYSA-N 0.000 description 1
- KCKWVNICLITNNZ-UHFFFAOYSA-N 15,17-dioxo-16-oxahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-5-carboxylic acid Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)O KCKWVNICLITNNZ-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- ZOUJXLSGXHKYOW-UHFFFAOYSA-N 2-(3,4-dicarboxyphenyl)-1,3-benzothiazole-5,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=NC2=CC(C(O)=O)=C(C(O)=O)C=C2S1 ZOUJXLSGXHKYOW-UHFFFAOYSA-N 0.000 description 1
- AZQIDBBXDFDNFG-UHFFFAOYSA-N 2-(3,4-dicarboxyphenyl)-1h-benzimidazole-5,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=NC2=CC(C(O)=O)=C(C(O)=O)C=C2N1 AZQIDBBXDFDNFG-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
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- DEFDRVWJULARRO-UHFFFAOYSA-N 4-(5-carboxy-1,3-benzothiazol-2-yl)phthalic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2SC=1C1=CC=C(C(O)=O)C(C(O)=O)=C1 DEFDRVWJULARRO-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AYOCQODSVOEOHO-UHFFFAOYSA-N carbamoyl carbamate Chemical class NC(=O)OC(N)=O AYOCQODSVOEOHO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- TWTZKRHWPGZFRW-UHFFFAOYSA-N cyclopenta-2,4-diene-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC1(C(O)=O)C(O)=O TWTZKRHWPGZFRW-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
- 230000000593 degrading effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- AIJZIRPGCQPZSL-UHFFFAOYSA-N ethylenetetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)=C(C(O)=O)C(O)=O AIJZIRPGCQPZSL-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/294—Coated or with bond, impregnation or core including metal or compound thereof [excluding glass, ceramic and asbestos]
- Y10T428/2942—Plural coatings
- Y10T428/2949—Glass, ceramic or metal oxide in coating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31681—Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46674474A | 1974-05-03 | 1974-05-03 | |
| US05/517,282 US3952084A (en) | 1974-05-03 | 1974-10-22 | Polyimide and polyamide-imide precursors prepared from esters, dianhydrides, and diisocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623837A5 true CH623837A5 (no) | 1981-06-30 |
Family
ID=27041768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH554675A CH623837A5 (no) | 1974-05-03 | 1975-04-30 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3952084A (no) |
| JP (1) | JPS5214274B2 (no) |
| CA (1) | CA1032697A (no) |
| CH (1) | CH623837A5 (no) |
| DE (1) | DE2518099A1 (no) |
| ES (1) | ES437122A1 (no) |
| FR (1) | FR2269557B1 (no) |
| GB (1) | GB1498049A (no) |
| IT (1) | IT1029289B (no) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208464A (en) * | 1974-09-26 | 1980-06-17 | Nitto Electric Industrial Co., Ltd. | Article coated with baked layer of water-soluble heat-resistant insulating varnish |
| DE2552350A1 (de) * | 1975-11-21 | 1977-05-26 | Bayer Ag | Lagerstabile, carbodiimidgruppen enthaltende polyisocyanate |
| US4107355A (en) * | 1976-03-25 | 1978-08-15 | Dr. Kurt Herberts & Co. Gesellschaft Mit Mit Beschrankter Haftung Vorm. Otto Louis Becker | Process for the production of highly heat-resistant insulating coatings on electrical conductors |
| US4294952A (en) * | 1978-11-30 | 1981-10-13 | Hitachi Chemical Company, Ltd. | Polyamide-imide resin and its production |
| FR2568258B1 (fr) * | 1984-07-25 | 1987-02-13 | Inst Francais Du Petrole | Compositions de precurseurs de polyimides, leur preparation, les polyimides en derivant et leurs utilisations, notamment dans la fabrication de vernis d'emaillage pour conducteurs electriques |
| US4670342A (en) * | 1985-04-08 | 1987-06-02 | General Electric Company | Method of making electrical inductive devices for use in hermetic refrigerant atmospheres |
| US4742153A (en) * | 1986-04-16 | 1988-05-03 | E. I. Du Pont De Nemours And Company | Process for preparing polyimides |
| US5470936A (en) * | 1993-05-28 | 1995-11-28 | Industrial Technology Research Institute | Process for preparing high-adhesion and high-solubility poly (amide-imide-ester) |
| KR101492894B1 (ko) * | 2012-06-12 | 2015-02-12 | 가부시키가이샤 나까타 코팅 | 이미도기 함유 화합물, 이미도기 함유 화합물 용액, 및 이미도기 함유 화합물의 제조 방법 |
| JP6024490B2 (ja) * | 2013-01-31 | 2016-11-16 | 日立金属株式会社 | ポリアミドイミド塗料及びそれを用いた絶縁電線 |
| US20160060483A1 (en) * | 2013-11-27 | 2016-03-03 | Nakata Coating Co., Ltd. | Imide group-containing compound solution and method for producing polyimide film derived from imide group-containing compound solution |
| US11753517B2 (en) | 2019-12-12 | 2023-09-12 | Raytheon Company | Dispensable polyimide aerogel prepolymer, method of making the same, method of using the same, and substrate comprising patterned polyimide aerogel |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL280333A (no) * | 1961-06-30 | |||
| DE1495823B2 (de) * | 1964-07-21 | 1976-09-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyesterimiden und deren verwendung fuer lacke |
| CH466924A (fr) * | 1965-07-02 | 1968-12-31 | Rhodiaceta | Procédé de fabrication de polyimides |
| GB1160097A (en) * | 1965-11-08 | 1969-07-30 | Mobil Oil Corp | Polyamide/Imide Polymers and the Enameling of Wire therewith |
| NL6601893A (no) * | 1966-02-15 | 1967-08-16 | ||
| US3489696A (en) * | 1966-10-06 | 1970-01-13 | Mobay Chemical Corp | Process of preparing polyimides from isocyanates and polycarboxylic acids |
| US3551383A (en) * | 1967-06-30 | 1970-12-29 | Du Pont | Aromatic polyamide-esters and a process for preparing them |
| US3708458A (en) * | 1971-03-16 | 1973-01-02 | Upjohn Co | Copolyimides of benzophenone tetracarboxylic acid dianhydride and mixture of diisocyanates |
| US3853813A (en) * | 1973-05-24 | 1974-12-10 | Westinghouse Electric Corp | Polyimide precursor and method and composition for preparing it |
-
1974
- 1974-10-22 US US05/517,282 patent/US3952084A/en not_active Expired - Lifetime
-
1975
- 1975-04-11 GB GB1489475A patent/GB1498049A/en not_active Expired
- 1975-04-14 CA CA224,515A patent/CA1032697A/en not_active Expired
- 1975-04-23 DE DE19752518099 patent/DE2518099A1/de not_active Ceased
- 1975-04-28 ES ES437122A patent/ES437122A1/es not_active Expired
- 1975-04-30 CH CH554675A patent/CH623837A5/de not_active IP Right Cessation
- 1975-05-02 IT IT4160375A patent/IT1029289B/it active
- 1975-05-02 JP JP5259875A patent/JPS5214274B2/ja not_active Expired
- 1975-05-05 FR FR7513979A patent/FR2269557B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50149796A (no) | 1975-12-01 |
| DE2518099A1 (de) | 1975-11-20 |
| GB1498049A (en) | 1978-01-18 |
| US3952084A (en) | 1976-04-20 |
| FR2269557A1 (no) | 1975-11-28 |
| CA1032697A (en) | 1978-06-06 |
| ES437122A1 (es) | 1977-07-01 |
| AU8069475A (en) | 1976-11-04 |
| FR2269557B1 (no) | 1981-07-24 |
| IT1029289B (it) | 1979-03-10 |
| JPS5214274B2 (no) | 1977-04-20 |
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased |