CA1281873C - Biaxially oriented paraphenylene sulfide block copolymer film and process for producing the same - Google Patents
Biaxially oriented paraphenylene sulfide block copolymer film and process for producing the sameInfo
- Publication number
- CA1281873C CA1281873C CA000525954A CA525954A CA1281873C CA 1281873 C CA1281873 C CA 1281873C CA 000525954 A CA000525954 A CA 000525954A CA 525954 A CA525954 A CA 525954A CA 1281873 C CA1281873 C CA 1281873C
- Authority
- CA
- Canada
- Prior art keywords
- film
- heat
- block copolymer
- recurring units
- measured
- 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 - Fee Related
Links
- XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002425 crystallisation Methods 0.000 claims abstract description 29
- 230000008025 crystallization Effects 0.000 claims abstract description 29
- 239000000155 melt Substances 0.000 claims abstract description 28
- 238000002844 melting Methods 0.000 claims abstract description 25
- 230000008018 melting Effects 0.000 claims abstract description 25
- 230000009477 glass transition Effects 0.000 claims abstract description 15
- 229920006254 polymer film Polymers 0.000 claims abstract description 13
- 238000009998 heat setting Methods 0.000 claims description 29
- 238000001816 cooling Methods 0.000 claims description 11
- 238000000465 moulding Methods 0.000 claims description 10
- 239000010408 film Substances 0.000 description 137
- 239000000203 mixture Substances 0.000 description 30
- 238000006116 polymerization reaction Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 24
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- 230000005291 magnetic effect Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000001491 aromatic compounds Chemical class 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 7
- 229910052976 metal sulfide Inorganic materials 0.000 description 7
- 229910052979 sodium sulfide Inorganic materials 0.000 description 7
- SOHCOYTZIXDCCO-UHFFFAOYSA-N 6-thiabicyclo[3.1.1]hepta-1(7),2,4-triene Chemical compound C=1C2=CC=CC=1S2 SOHCOYTZIXDCCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000001465 metallisation Methods 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- -1 arylene sulfide Chemical compound 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000005294 ferromagnetic effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229910000859 α-Fe Inorganic materials 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 235000010893 Bischofia javanica Nutrition 0.000 description 1
- 240000005220 Bischofia javanica Species 0.000 description 1
- IBNQSWKJEBUSIE-UHFFFAOYSA-N CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O Chemical compound CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O.CNP(NC)(NC)=O IBNQSWKJEBUSIE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 229910004874 Na2S 9H2O Inorganic materials 0.000 description 1
- 244000166490 Tetrameles nudiflora Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C55/00—Shaping by stretching, e.g. drawing through a die; Apparatus therefor
- B29C55/02—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets
- B29C55/10—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets multiaxial
- B29C55/12—Shaping by stretching, e.g. drawing through a die; Apparatus therefor of plates or sheets multiaxial biaxial
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0209—Polyarylenethioethers derived from monomers containing one aromatic ring
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0245—Block or graft polymers
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0286—Chemical after-treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2381/02—Polythioethers; Polythioether-ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60294681A JPH066339B2 (ja) | 1985-12-27 | 1985-12-27 | パラフエニレンスルフイドブロツクコポリマ−２軸延伸フイルム及びその製造法 |
| JP294681/85 | 1985-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1281873C true CA1281873C (en) | 1991-03-26 |
Family
ID=17810927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000525954A Expired - Fee Related CA1281873C (en) | 1985-12-27 | 1986-12-22 | Biaxially oriented paraphenylene sulfide block copolymer film and process for producing the same |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH066339B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1281873C (enrdf_load_stackoverflow) |
| DE (1) | DE3644365A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2592384B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2184978B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62242517A (ja) * | 1986-04-14 | 1987-10-23 | Kureha Chem Ind Co Ltd | ポリパラフェニレンスルフィド２軸延伸フィルム及びその製造方法 |
| JPS6333427A (ja) * | 1986-07-25 | 1988-02-13 | Diafoil Co Ltd | ポリフエニレンスルフイドフイルム |
| US4960806A (en) * | 1988-10-25 | 1990-10-02 | Kureha Kagaku Kagyo K.K. | Stretched poly(arylene thioether) block copolymer films and production process thereof |
| US5155207A (en) * | 1988-12-29 | 1992-10-13 | Phillips Petroleum Company | Arylene sulfide polymers and articles of manufacture |
| CN102548704B (zh) * | 2009-09-16 | 2015-01-28 | 新日铁住金株式会社 | 电焊管焊接装置 |
| JP4741717B2 (ja) | 2009-09-16 | 2011-08-10 | 新日本製鐵株式会社 | 電縫管溶接装置 |
| JP2014001363A (ja) * | 2012-05-21 | 2014-01-09 | Toray Ind Inc | 金属接着用二軸延伸ポリアリーレンスルフィドフィルム |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286018A (en) * | 1978-04-28 | 1981-08-25 | Toray Industries, Incorporated | Biaxially oriented poly-p-phenylene sulfide films |
| US4629778A (en) * | 1982-05-20 | 1986-12-16 | Dainippon Ink And Chemicals, Inc. | Poly(p-phenylene sulfide) film and process for production thereof |
| JPS6096439A (ja) * | 1983-10-31 | 1985-05-30 | Sumitomo Chem Co Ltd | 垂直磁化用ポリｐ−フエニレンスルフイドフイルム |
| CA1260174A (en) * | 1984-06-29 | 1989-09-26 | Kureha Chemical Ind Co Ltd | PARA-PHENYLENE SULPHIDE COPOLYMERS; METHOD OF PREPARATION AND USE |
| EP0171021B1 (de) * | 1984-08-07 | 1993-07-21 | Bayer Ag | Polyphenylensulfide, Verfahren zur Herstellung der Polyphenylensulfide und deren Verwendung |
-
1985
- 1985-12-27 JP JP60294681A patent/JPH066339B2/ja not_active Expired - Lifetime
-
1986
- 1986-12-22 CA CA000525954A patent/CA1281873C/en not_active Expired - Fee Related
- 1986-12-23 GB GB8630779A patent/GB2184978B/en not_active Expired
- 1986-12-24 DE DE19863644365 patent/DE3644365A1/de active Granted
- 1986-12-24 FR FR868618153A patent/FR2592384B1/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB8630779D0 (en) | 1987-02-04 |
| FR2592384B1 (fr) | 1992-05-15 |
| JPH066339B2 (ja) | 1994-01-26 |
| JPS62152828A (ja) | 1987-07-07 |
| GB2184978A (en) | 1987-07-08 |
| DE3644365C2 (enrdf_load_stackoverflow) | 1991-01-17 |
| DE3644365A1 (de) | 1987-07-02 |
| GB2184978B (en) | 1989-10-18 |
| FR2592384A1 (fr) | 1987-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |