WO1993011189A1 - Oxidation inhibited arylcyclobutene polymers - Google Patents
Oxidation inhibited arylcyclobutene polymers Download PDFInfo
- Publication number
- WO1993011189A1 WO1993011189A1 PCT/US1992/010173 US9210173W WO9311189A1 WO 1993011189 A1 WO1993011189 A1 WO 1993011189A1 US 9210173 W US9210173 W US 9210173W WO 9311189 A1 WO9311189 A1 WO 9311189A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antioxidant
- compound
- group
- hydrogen
- arylcyclobutene
- Prior art date
Links
- 0 *c1cc(*)c(*)c(N)c1 Chemical compound *c1cc(*)c(*)c(N)c1 0.000 description 7
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
Definitions
- DVS 3-bis(2-bicyclo[4.2.0]octa-1 , 3, 5-trien-3-ylethenyl)- 1 , 1 , 3, 3-tetramethyldisiloxane
- DVS 3-bis(2-bicyclo[4.2.0]octa-1 , 3, 5-trien-3-ylethenyl)- 1 , 1 , 3, 3-tetramethyldisiloxane
- Cyclotene 3022 ® hereinafter partially thermally polymerized DVS or DVS • prepolymer
- the partially thermally polymerized DVS may be applied by spin coating a solution of a prepolymer onto a substrate, evaporating the solvent and then polymerizing by heating to 250°C for one hour in nitrogen.
- the invention is a method for inhibiting oxidation of a polymer formed by the side ring opening of compounds containing one or more arylcyclobutene moieties by adding to the monomer compound, the prepolymer or polymer of the compound, an amount of said antioxidant sufficient to inhibit oxidation of the polymer.
- the invention is an article containing a component which is a polymer formed by the side ring opening of an arylcyclobutene moiety and an amount of said antioxidant sufficient to inhibit oxidation of the polymer.
- the 'side ring' of an arylcyclobutene contains two carbon atoms not in the aromatic ring that are connected to adjacent carbon atoms on the same aryl ring, the bond between said carbon atoms and the two bonds between the carbon atoms and the aryl ring.
- Arylcyclobutenes are thought to react bythe opening of this ring between the two carbon atoms which can produce an orthoxylylene moiety as a reactive intermediate.
- the orthoxylylene moiety is a diene which may react with dienophiles and with other orthoxylylene moieties.
- the orthoxylylene moiety may also participate in free radical reactions.
- Suitable electron-withdrawing moieties include -N02, -CN, Br, I, Cl, F,
- the most preferred bisbenzocyclobutene monomer can be prepared by reacting about 2 moles of bromobenzocyclobutene with about one mole of 1,3-divinyl-1,1,3,3-tetramethyl-disiloxane in the presence of a catalytic amount of palladium acetate and tri(ortho-tolyl)phosphine, in addition to triethylamine, which acts as an acid scavenger.
- the prepolymer contains both reacted and unreacted polymerization sites. It may contain completely unreacted arylcyclobutene compound, oligomers and cured polymer as well as other unreacted materials included in the arylcyclobutene compound.
- Tinuvin ® 622 which is available as Tinuvin ® 622 from Ciba-Geigy;
- Tinuvin ® 622 which is available as Tinuvin ® 622 as a polymer from Ciba-Geigy;
- a 25-cm 3 flask equipped with a reflux condenser, nitrogen inletand magnetic stirring bar is charged with 4-bromobenzocyclobutene (1.5 g, 8 x 10 "3 moles), the diterminal olefin from part A (1.34 g, 4 x 10 '3 moles), tri-n-butylam ⁇ ne (1.8 g, 9.7 x 10 '3 moles), tri-o- tolylphosphine (62 mg, 4.0 x 10 "4 moles), palladium II acetate (18 mg, 8.0 x 10 "5 moles) and acetonitrile (5 cm 3 )- The reaction mixture is heated to reflux under nitrogen for 4 hours.
- the solvent is evaporated and the film isthermally cured at250°C for one hour under a nitrogen atmosphere, preferably containing less than 100 ppm oxygen-
- the cured-polymer coated wafers are then placed in air purged ovens at the temperatures noted and are withdrawn periodically to obtain FT-IR spectral absorbance measurements. Lifetimes of the films are based on the time it takes the absorbance at 1500 cm "1 to reach 80 percent of its initial value. This band indicates the presence of tetralfn which contains the benzylic hydrogens. Comparisons have shown that this corresponds to about a 10 percent increase in the dielectric constant which is the real indicator of interest in thin film dielectrics.
- the use of silicon wafers permits the taking of the absorbance spectral measurements through the transparent wafer and polymerfilm without degrading the film. Absorbance measurements in this context refer to the definition given by:
- the absorbance band at 1500 cm "1 typically does not have a local baseline at zero absorbance. Therefore, the absorbance at 1500 cm '1 is measured relative to a line connecting two points taken as the local spectral baseline. 1520 cm '1 and 1470 cm “1 may advantageously be used to define the local baseline.
- the solvent is evaporated and the film is thermally cured at 250°C for one hour under a nitrogen atmosphere, preferably containing less than 100 ppm oxygen.
- the cured-polymer coated wafers are then placed in air purged ovens at 170°C and are withdrawn periodically to obtain FT-IR spectral absorbance measurements.
- Agerite ® MA is tested as an antioxidant for the Cyclotene 3022® prepolymer at the weight percents indicated in TABLE IV based on the weight of the prepolymer.
- the solutions are spin coated onto oxide free silicon wafers atthicknesses resulting in polymer coatings of about ten microns. After spin coating a film, the solvent is evaporated and the film is partially cured using E-beam at the doses stated in the TABLE IV. After the stated E-beam dose is administered the film is cured at 250°C for one 5 hour under a nitrogen atmosphere, preferably containing less than 100 ppm oxygen. The cured-polymer coated wafers are then placed in air purged ovens at 150°C and are withdrawn periodically to obtain FT-IR spectral absorbance measurements.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69229558T DE69229558T2 (en) | 1991-11-27 | 1992-11-23 | ARYLCYCLOBUTANE POLYMERS PROTECTED FROM OXYDATION |
KR1019940701768A KR100249583B1 (en) | 1991-11-27 | 1992-11-23 | Oxidation inhibited arylcyclobutene polymers |
EP93900651A EP0614474B1 (en) | 1991-11-27 | 1992-11-23 | Oxidation inhibited arylcyclobutene polymers |
JP51023493A JP3213000B2 (en) | 1991-11-27 | 1992-11-23 | Antioxidant arylcyclobutene polymer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/800,787 | 1991-11-27 | ||
US07/800,787 US5185391A (en) | 1991-11-27 | 1991-11-27 | Oxidation inhibited arylcyclobutene polymers |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993011189A1 true WO1993011189A1 (en) | 1993-06-10 |
Family
ID=25179359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1992/010173 WO1993011189A1 (en) | 1991-11-27 | 1992-11-23 | Oxidation inhibited arylcyclobutene polymers |
Country Status (10)
Country | Link |
---|---|
US (1) | US5185391A (en) |
EP (1) | EP0614474B1 (en) |
JP (1) | JP3213000B2 (en) |
KR (1) | KR100249583B1 (en) |
CA (1) | CA2121051A1 (en) |
DE (1) | DE69229558T2 (en) |
MY (1) | MY110821A (en) |
SG (1) | SG44646A1 (en) |
TW (1) | TW221702B (en) |
WO (1) | WO1993011189A1 (en) |
Cited By (1)
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US9752051B2 (en) | 2015-04-06 | 2017-09-05 | Rohm And Haas Electronic Materials Llc | Polyarylene polymers |
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US5411969A (en) * | 1993-04-16 | 1995-05-02 | Bristol-Myers Squibb Company | Antihyperlipidemic/antioxidant dihydroquinolines |
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US5668210A (en) * | 1994-10-24 | 1997-09-16 | The Dow Chemical Company | Adhesion promoter and self-priming arylcyclobutene resin compositions |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US3991139A (en) * | 1974-04-23 | 1976-11-09 | Showa Denko Kabushiki Kaisha | High heat stability composition of ring-opening polymerization product |
US4540763A (en) * | 1984-09-14 | 1985-09-10 | The Dow Chemical Company | Polymers derived from poly(arylcyclobutenes) |
US4622375A (en) * | 1986-03-28 | 1986-11-11 | Shell Oil Company | Amorphous ethylene/propylene polymers |
US4642329A (en) * | 1984-08-27 | 1987-02-10 | The Dow Chemical Company | Prepolymer processing of arylcyclobutene monomeric compositions |
US4783514A (en) * | 1986-02-28 | 1988-11-08 | The Dow Chemical Company | Polymeric monoarylcyclobutane compositions |
US4822839A (en) * | 1987-11-25 | 1989-04-18 | Hercules Incorporated | Polyunsaturated hydrocarbon polymer-compatible antioxidant compositions |
US4960593A (en) * | 1985-01-30 | 1990-10-02 | Hilmont Incorporated | Process for preparing thermally stable olefinic polymers |
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JP2579937B2 (en) * | 1987-04-15 | 1997-02-12 | 株式会社東芝 | Electronic circuit device and method of manufacturing the same |
US4812588A (en) * | 1987-12-14 | 1989-03-14 | The Dow Chemical Company | Polyorganosiloxane-bridged bisbenzocyclobutene monomers |
JPH02165662A (en) * | 1988-12-20 | 1990-06-26 | Dainippon Printing Co Ltd | Mounting method for semiconductor integrated circuit |
-
1991
- 1991-11-27 US US07/800,787 patent/US5185391A/en not_active Expired - Lifetime
-
1992
- 1992-11-23 JP JP51023493A patent/JP3213000B2/en not_active Expired - Lifetime
- 1992-11-23 KR KR1019940701768A patent/KR100249583B1/en not_active IP Right Cessation
- 1992-11-23 DE DE69229558T patent/DE69229558T2/en not_active Expired - Lifetime
- 1992-11-23 CA CA002121051A patent/CA2121051A1/en not_active Abandoned
- 1992-11-23 WO PCT/US1992/010173 patent/WO1993011189A1/en active IP Right Grant
- 1992-11-23 SG SG1996004922A patent/SG44646A1/en unknown
- 1992-11-23 EP EP93900651A patent/EP0614474B1/en not_active Expired - Lifetime
- 1992-11-27 MY MYPI92002181A patent/MY110821A/en unknown
- 1992-12-02 TW TW081109651A patent/TW221702B/zh not_active IP Right Cessation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3991139A (en) * | 1974-04-23 | 1976-11-09 | Showa Denko Kabushiki Kaisha | High heat stability composition of ring-opening polymerization product |
US4642329A (en) * | 1984-08-27 | 1987-02-10 | The Dow Chemical Company | Prepolymer processing of arylcyclobutene monomeric compositions |
US4540763A (en) * | 1984-09-14 | 1985-09-10 | The Dow Chemical Company | Polymers derived from poly(arylcyclobutenes) |
US4960593A (en) * | 1985-01-30 | 1990-10-02 | Hilmont Incorporated | Process for preparing thermally stable olefinic polymers |
US4783514A (en) * | 1986-02-28 | 1988-11-08 | The Dow Chemical Company | Polymeric monoarylcyclobutane compositions |
US4622375A (en) * | 1986-03-28 | 1986-11-11 | Shell Oil Company | Amorphous ethylene/propylene polymers |
US4822839A (en) * | 1987-11-25 | 1989-04-18 | Hercules Incorporated | Polyunsaturated hydrocarbon polymer-compatible antioxidant compositions |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9752051B2 (en) | 2015-04-06 | 2017-09-05 | Rohm And Haas Electronic Materials Llc | Polyarylene polymers |
Also Published As
Publication number | Publication date |
---|---|
DE69229558T2 (en) | 2000-03-30 |
EP0614474A1 (en) | 1994-09-14 |
KR100249583B1 (en) | 2000-03-15 |
EP0614474B1 (en) | 1999-07-07 |
DE69229558D1 (en) | 1999-08-12 |
US5185391A (en) | 1993-02-09 |
SG44646A1 (en) | 1997-12-19 |
TW221702B (en) | 1994-03-11 |
EP0614474A4 (en) | 1995-06-28 |
MY110821A (en) | 1999-05-31 |
JP3213000B2 (en) | 2001-09-25 |
JPH07501572A (en) | 1995-02-16 |
CA2121051A1 (en) | 1993-06-10 |
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