GB1076722A - Improvements in silylated polyamide acid resins and polyimides derived therefrom - Google Patents
Improvements in silylated polyamide acid resins and polyimides derived therefromInfo
- Publication number
- GB1076722A GB1076722A GB1599065A GB1599065A GB1076722A GB 1076722 A GB1076722 A GB 1076722A GB 1599065 A GB1599065 A GB 1599065A GB 1599065 A GB1599065 A GB 1599065A GB 1076722 A GB1076722 A GB 1076722A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- formula
- silylated
- radical
- polyamide acid
- 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
Links
- 239000004952 Polyamide Substances 0.000 title abstract 5
- 239000002253 acid Substances 0.000 title abstract 5
- 229920002647 polyamide Polymers 0.000 title abstract 5
- 239000011347 resin Substances 0.000 title abstract 5
- 229920005989 resin Polymers 0.000 title abstract 5
- 229920001721 polyimide Polymers 0.000 title abstract 3
- 239000004642 Polyimide Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 150000004985 diamines Chemical class 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical class CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 239000004020 conductor Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000009719 polyimide resin Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 abstract 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000006159 dianhydride group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/302—Polyurethanes or polythiourethanes; Polyurea or polythiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- 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
-
- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/303—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 H01B3/38 or H01B3/302
- H01B3/306—Polyimides or polyesterimides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/307—Other macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A polymer composed of the recurring unit <FORM:1076722/C3/1> is prepared by reacting, in a solvent for at least one of the reactants and for the silylated polyamide acid resin thereby obtained, a silylated diamine of the formula <FORM:1076722/C3/2> with at least one tetracarboxylic acid dianhydride of the formula <FORM:1076722/C3/3> wherein Z is a monovalent hydrocarbon radical, R is a tetravalent radical containing at least 6 carbon atoms in a ring having benzenoid unsaturation, the four carbonyl groups being attached to separate carbon atoms in the ring, and each pair of -NH-CO- and -CO2SiZ3 substituents shown in the first formula on the right and left of R respectively being attached to adjacent carbon atoms in the R radical, R1 is a divalent aromatic radical of at least 6 carbon atoms and X is an integer greater than 1. Preferred solvents are dioxane, tetrahydrofuran, tetrahydropyran or a mixture of N-methylpyrrolidone with any one of the above solvents or with a mixture of alkylated benzenes, toluene and acetonitrile. Dianhydrides exemplified are pyromellitic dianhydride and benzophenone tetracarboxylic acid dianhydride, but many others are specified. Suitable silylated diamines are N,N1-bis(trimethylsilyl)-p,p1-diaminodiphenyl ether, N,N1-bis(trimethylsilyl)-m - phenylene diamine, N,N1 - bis(trimethylsilyl) - p - phenylenediamine and N,N1 - bis (trimethylsilyl) - p,p1 - diaminodiphenylmethane. The silylated polyamide acid resins on heating split off the triorganosiloxy group as either the triorganosilanol or the hexaorganosiloxane, with the concurrent formation of the polyimide resin. The triorganosilyl diamines can be prepared by reacting a diamine of the formula H2N-R1-NH2 with a triorganosilane of the formula Z3SiX, where R1 and Z have the meanings given above and X is a halogen atom. At least 2 and up to 6 moles of the silane may be reacted with 1 mol. of the diamine preferably in the presence of a solvent such as benzene, toluene, xylene or dioxane and a hydrohalide acceptor such as pyridine, triethylamine or other tertiary amine. Preparations of the silylated diamines specified in the paragraph above are exemplified.ALSO:Electrical conductors e.g. copper and aluminium may be coated with a solution in a suitable solvent of a polyamide acid resin having recurring units of the formula: <FORM:1076722/B1-B2/1> wherein Z is a monovalent hydrocarbon radical, R is a tetravalent radical containing at least 6 carbon atoms in a ring having benzenoid unsaturation, the four carbonyl groups being attached to separate carbon atoms in the ring, and each pair of -NHCO- and -CO2 SiZ3 substituents shown in the formula on the right and left of R respectively being attached to adjacent carbon atoms in the R radical, R1 is a divalent aromatic radical of at least 6 carbon atoms, and X is an integer greater than 1. The coated conductor may then be passed through a heated tower at 150 DEG C to 350 DEG C to convert the silylated polyamide acid resin to the corresponding polyimide resin with volatilization of the solvent and the triorganosilanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US359928A US3303157A (en) | 1964-04-15 | 1964-04-15 | Silylated polyamide-acids and compositions thereof |
| US36010564 US3172874A (en) | 1964-04-15 | 1964-04-15 | Xnxz xnx xnx |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1076722A true GB1076722A (en) | 1967-07-19 |
Family
ID=27000676
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1598965A Expired GB1076721A (en) | 1964-04-15 | 1965-04-14 | Improvements in organosilicon compositions and methods for preparing the same |
| GB1599065A Expired GB1076722A (en) | 1964-04-15 | 1965-04-14 | Improvements in silylated polyamide acid resins and polyimides derived therefrom |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1598965A Expired GB1076721A (en) | 1964-04-15 | 1965-04-14 | Improvements in organosilicon compositions and methods for preparing the same |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE1570659A1 (en) |
| GB (2) | GB1076721A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2189788A (en) * | 1986-03-27 | 1987-11-04 | Central Glass Co Ltd | Aromatic diamines suitable as polymer material and method of preparing same |
| EP0361461A2 (en) * | 1988-09-30 | 1990-04-04 | Hitachi, Ltd. | Process for producing metal-polyimide composite article |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460308A1 (en) * | 1979-07-03 | 1981-01-23 | Rhone Poulenc Ind | PROCESS FOR THE PREPARATION OF POLYMERS WITH IMIDE MODIFIED BY SILICON |
| FR2755694B1 (en) * | 1996-11-13 | 1999-02-05 | Emfi Sa | PROCESS FOR THE TEMPORARY DEACTIVATION OF AN ACTIVE HYDROGEN CHEMICAL COMPOUND AND CHEMICAL COMPOSITION OBTAINED |
-
1965
- 1965-04-13 DE DE1965G0043332 patent/DE1570659A1/en active Pending
- 1965-04-13 DE DE1965G0043333 patent/DE1570660A1/en active Pending
- 1965-04-14 GB GB1598965A patent/GB1076721A/en not_active Expired
- 1965-04-14 GB GB1599065A patent/GB1076722A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2189788A (en) * | 1986-03-27 | 1987-11-04 | Central Glass Co Ltd | Aromatic diamines suitable as polymer material and method of preparing same |
| FR2601018A1 (en) * | 1986-03-27 | 1988-01-08 | Central Glass Co Ltd | AROMATIC DIAMINES APPROPRIATED AS POLYBENZOXAZOLE POLYMER MATERIAL AND PROCESS FOR THEIR PREPARATION |
| EP0361461A2 (en) * | 1988-09-30 | 1990-04-04 | Hitachi, Ltd. | Process for producing metal-polyimide composite article |
| EP0361461A3 (en) * | 1988-09-30 | 1990-12-19 | Hitachi, Ltd. | Process for producing metal-polyimide composite article |
| US5133989A (en) * | 1988-09-30 | 1992-07-28 | Hitachi, Ltd. | Process for producing metal-polyimide composite article |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1570659A1 (en) | 1970-01-22 |
| DE1570660A1 (en) | 1970-03-19 |
| GB1076721A (en) | 1967-07-19 |
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