JPH0476077A - Aromatic polyether ketone-based resin varnish and its preparation - Google Patents
Aromatic polyether ketone-based resin varnish and its preparationInfo
- Publication number
- JPH0476077A JPH0476077A JP18788490A JP18788490A JPH0476077A JP H0476077 A JPH0476077 A JP H0476077A JP 18788490 A JP18788490 A JP 18788490A JP 18788490 A JP18788490 A JP 18788490A JP H0476077 A JPH0476077 A JP H0476077A
- Authority
- JP
- Japan
- Prior art keywords
- varnish
- polyether ketone
- aromatic polyether
- aromatic polyetherketone
- aromatic
- 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.)
- Pending
Links
- 239000011347 resin Substances 0.000 title claims abstract description 33
- 229920005989 resin Polymers 0.000 title claims abstract description 33
- 239000002966 varnish Substances 0.000 title claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 26
- 229920001643 poly(ether ketone) Polymers 0.000 title claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- -1 ether ketone Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000011248 coating agent Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
本発明は、芳香族ポリエーテルケトン系樹脂を含む、ワ
ニス、及びその製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a varnish containing an aromatic polyetherketone resin and a method for producing the same.
芳香族ポリエーテルケトン系樹脂は耐熱性、機械的性質
、電気的性質、寸法安定性等に優れており、吸水率が低
く、物性的に良好なポリマーであることがよく知られて
いる。又、特に耐薬品性に優れており、濃硫酸以外の薬
品には溶解されず、高温時の耐酸性、耐アルカリ性にも
侯れたポリマーである。It is well known that aromatic polyetherketone resins are polymers with excellent heat resistance, mechanical properties, electrical properties, dimensional stability, etc., low water absorption, and good physical properties. In addition, it is a polymer that has particularly excellent chemical resistance, is not dissolved in chemicals other than concentrated sulfuric acid, and has excellent acid resistance and alkali resistance at high temperatures.
このような芳香族ポリエーテルケトン系樹脂の良好な耐
薬品性は、成形物としての使用、例えば電気・電子部品
等の精密成形品、フィルム等としては非常に都合が良い
が、ワニスとしての使用が不可能であった。唯一、芳香
族ポリエーテルケトン系樹脂を溶解することが出来ると
いわれている濃硫酸の場合には、−旦溶解すると、スル
ボン化が進み、やがてはポリマーの分解を生じ、その安
定性は極めて悪い。以上の様に芳香族ポリエーテルケＩ
・ン系樹脂のワニスば、樹脂を溶解する溶媒が知られて
いなかったため、これ迄世の中には存在せず、塗料、接
着ワニス、コーティング剤、シル材用途としての応用は
全く知られていない。The good chemical resistance of aromatic polyetherketone resins is very convenient for use as molded products, such as precision molded products such as electrical and electronic parts, films, etc., but it is also very convenient for use as varnishes. was not possible. In the case of concentrated sulfuric acid, which is said to be the only solution capable of dissolving aromatic polyetherketone-based resins, - once dissolved, sulfonation progresses, eventually causing decomposition of the polymer, and its stability is extremely poor. . As mentioned above, aromatic polyether
-N-based resin varnishes have not existed in the world until now because there were no known solvents that could dissolve the resins, and their application as paints, adhesive varnishes, coating agents, and seal materials was completely unknown.
本発明の目的は、芳香族ポリエーテルケトン系樹脂のイ
■れた物性に加え、優れた加工性を有し、多口的用途に
使用可能な芳香族ポリエーテルケＩ・ン系樹脂ワニスを
得ることにある。The purpose of the present invention is to obtain an aromatic polyetherketone resin varnish that has excellent processability in addition to the excellent physical properties of aromatic polyetherketone resin and can be used for multiple purposes. It is in.
本発明者ろは前記目的を達成ずろために鋭意検討した結
果、芳香族ポリエーテルリドン系樹脂をワニスとして実
用可能な濃度で溶解する溶媒を見出し、芳香族ポリエー
テルケトン系樹脂ワニスを見出した。As a result of intensive studies aimed at achieving the above object, the present inventors found a solvent that dissolves aromatic polyetherridone resin at a concentration that is practical for use as a varnish, and thus discovered an aromatic polyetherketone resin varnish.
即し本発明は、
（１）下記の一般式（１）〜（Ｖ）に示される繰り返し
単位を有する芳香族ポリエーテルケトン系樹脂から選ば
れた１種または２種以上の混合物０．０１重量％〜３０
重量％を含む芳香族ポリエーテルケ１−ン系樹脂ワニス
、
（２）ワニスの）容媒が、フェノール系溶媒であること
を特徴とする請求項１記載のワニス、
（３）請求項（１）記載の芳香族ポリエーテルケトン系
樹脂から選ばれた１種または２種以上の混合物０，０１
重量％〜３０重景％を含む芳香族ポリエーテルケトン系
樹脂を、フェノール系溶媒を用い、２０℃〜３００℃の
温度で溶解して製造することを特徴とする芳香族ポリエ
ーテルケトン系樹脂ワニスの製造方法、
である。Therefore, the present invention provides: (1) 0.01 weight of one type or a mixture of two or more types selected from aromatic polyetherketone resins having repeating units represented by the following general formulas (1) to (V); %~30
(2) the varnish according to claim 1, wherein the carrier (of the varnish) is a phenolic solvent; (3) the varnish according to claim (1); One or more mixtures of aromatic polyetherketone resins selected from aromatic polyetherketone resins 0.01
An aromatic polyetherketone resin varnish produced by dissolving an aromatic polyetherketone resin containing % by weight to 30% by weight using a phenolic solvent at a temperature of 20°C to 300°C. The manufacturing method is as follows.
前述の様に芳香族ポリエーテルケトン系樹脂を完全に溶
解するものとしては、票硫酸しか知られていなかった。As mentioned above, only sulfuric acid was known to completely dissolve aromatic polyetherketone resins.
本発明者等は各種溶媒を検潤した結果、フェノール系）
容剤が、前記目的に最適であることを見出し、本発明に
至ったものである。As a result of testing various solvents, the inventors found that
The inventors have discovered that the container is optimal for the above purpose, leading to the present invention.
本発明に用いられるフェノール系溶媒としては、フェノ
ール、パラ−クレゾール、ｍ−クレゾール、０−クレゾ
ール、パラ−クロルフェノール、メタクロルフェノール
、オルソ−りロルフェノール、キンレン、ジクロロフェ
ノール トリクロＩコフエノール、デＩ・ラクロロフ丁
、ノール、ペンククロロフェノール等が挙げられ、これ
らは単独或いは２種以上混合して用いられる。特に凝固
点の高い溶媒の場合は固化を防くため、２種以上混合し
て用いることが特に好ましい。The phenolic solvents used in the present invention include phenol, para-cresol, m-cresol, 0-cresol, para-chlorophenol, methachlorophenol, ortho-chlorophenol, quinolene, dichlorophenol, trichloro-I cophenol, de-I - Examples include laclorofphenol, nol, pencchlorophenol, etc., and these may be used alone or in a mixture of two or more. In particular, in the case of a solvent with a high freezing point, it is particularly preferable to use a mixture of two or more to prevent solidification.
ワニス中のポリマー重量に特に制限は無い、余りに少な
いと、使用に際して溶媒の揮散に時間がかかったり、厚
いフィルムの製造や、厚くコートすることが難しくなる
ので、０．０１重量％以上が好ましい。又、余りに樹脂
の重量が多いとワニスの粘度が高くなり、取り扱いが困
難となるので、その上限は３０％程度が好ましい。There is no particular restriction on the weight of the polymer in the varnish; if it is too small, it will take time to volatilize the solvent during use, and it will be difficult to manufacture a thick film or coat thickly, so it is preferably 0.01% by weight or more. Furthermore, if the weight of the resin is too large, the viscosity of the varnish will become high, making it difficult to handle, so the upper limit is preferably about 30%.
ワニスの調整は通常２０℃から３００“Ｃの間で調整さ
れるが、溶解を速めるためには加熱するのが好ましく、
通常は５０℃から３００℃１更に好ましくは１００ ’
Ｃ以上に加熱して）容解する。The varnish is usually adjusted between 20°C and 300"C, but it is preferable to heat it to speed up the dissolution.
Usually 50℃ to 300℃1 more preferably 100'
Heat to above C) to dissolve.
溶解に際してポリエーテルケトン系樹脂はパウダ、ペレ
ット、フィルム、成形物など、いずれの携帯でもよいが
、ペレット、成形物の場合は、溶解速度を速めるため、
粉砕して用いるのが特に好ましい。ポリエーテルケトン
系樹脂の種類には特に制限は無く、市場で入手可能なも
のが自由に選ばれるが、前記−形式（１）〜（Ｖ）で示
されるものが特に好ましく、これらは単独でも２種以上
混合しても使える。When dissolving the polyetherketone resin, it can be used in any form such as powder, pellets, film, or molded products, but in the case of pellets or molded products, in order to accelerate the dissolution rate,
It is particularly preferable to use it after pulverization. There is no particular restriction on the type of polyetherketone resin, and those available on the market can be freely selected, but those shown in the above-mentioned formats (1) to (V) are particularly preferred, and these alone can also be used as You can also use a mixture of more than one species.
以下、実施例により本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例−１
還流冷却器、かきまぜ機を備えた容器に、Ｐクロロフェ
ノールとフェノールの？Ｒ合？８ 媒（ｐクロフェノー
ル−フェノール−９０・１０重量比）２０００ｍＲにＩ
ＣＩ社製ＰＥＥＫ
４５０ｐパウダー５０ｇを懸濁し７た。かきまぜながら
徐々に昇温し、１８０℃で３０分間保持したところ、完
全に７容解した。Example-1 P-chlorophenol and phenol were placed in a container equipped with a reflux condenser and a stirrer. R match? 8 Medium (p-chlorophenol-phenol-90/10 weight ratio) 2000 mR
50 g of PEEK 450p powder manufactured by CI was suspended. The temperature was gradually raised while stirring and held at 180°C for 30 minutes, resulting in a complete dissolution of 7 ml.
このワニスの一部を取り、上記Ｐ−クロロフェノール：
フェノール混合溶液を加え、樹脂分０．５ｇ／１００ｍ
！２となるようにン容ン夜を３周整し、対数粘度を測定
したところ、０．９５ａ／ｇであった。上記ワニスを室
温にて放置し、ポリマーの安定性を調べたところ、３日
後で０．９５社／ｇｉｏ日後も０．９５准／ｇと、非常
に安定であった。Take a part of this varnish and prepare the above P-chlorophenol:
Add phenol mixed solution, resin content 0.5g/100m
! The logarithmic viscosity was measured three times to obtain a viscosity of 0.95 a/g. When the above varnish was left at room temperature and the stability of the polymer was examined, it was found to be extremely stable, with a value of 0.95 min/g after 3 days/0.95 min/g after 3 days.
実施例−２
実施例−１と同様の容器に、ｐ−クロロフエノル２００
０ｍＲと、ＴＣ１社製ＰＥＥＫ ４５０Ｇ （ベレ・＞
ト）６０ｇを分散し、かきまぜながら徐々に昇温し、２
１７℃で１時間保持したところ、完全に溶解した。この
ワニスの一部をとり、Ｐ−クロロフェノールで希釈して
樹脂分０．５ ｇ ／ １００ ｍｌとなるように溶液
を調整し、対数粘度を測定したところ、０．９３准／ｇ
であった。Example-2 In a container similar to Example-1, 200 p-chlorophenol was added.
0mR and PEEK 450G manufactured by TC1 (Bere)
g) Disperse 60g and gradually raise the temperature while stirring.
When the mixture was kept at 17°C for 1 hour, it was completely dissolved. A portion of this varnish was taken and diluted with P-chlorophenol to prepare a solution with a resin content of 0.5 g/100 ml.The logarithmic viscosity was measured and found to be 0.93 s/g.
Met.
実施例−３
実施例−１と同様の容器にｍ−クロロフェノール２００
０ｍＲと、ＩＣ１社製ＰＥＫ
２Ｏ０ｐ （パウダー）６０ｇを分散し、かきまぜなが
ら２１０℃に３０分間保持したところ完全に溶解し、Ｐ
Ｅ Ｈのワニスが得られた。このワニスの一部をとり
ｍ−クロロフェノールで希釈し、樹脂分０．５ｇ／１０
０ｄとなるように溶液を調整し、対数粘度を測定したと
ごろ０．８５ａ／ｇであった。Example-3 200 m-chlorophenol in the same container as Example-1
When 0 mR and 60 g of PEK 2O0p (powder) manufactured by IC1 were dispersed and kept at 210°C for 30 minutes while stirring, the P
A varnish of EH was obtained. A portion of this varnish was diluted with m-chlorophenol, and the resin content was 0.5g/10.
The solution was adjusted so that the viscosity was 0d, and the logarithmic viscosity was measured and found to be 0.85a/g.
本発明によると、芳香族ポリエーテルケトン系樹脂の有
機溶剤ワニスを製造することが出来、塗料、接着ワニス
、コーティング剤、シール材としての用途等に巾広く展
開できる。According to the present invention, it is possible to produce an organic solvent varnish made of aromatic polyetherketone resin, which can be used in a wide range of applications such as paints, adhesive varnishes, coating agents, and sealing materials.
特許出願人 三井東圧化学株式会社
手続補正書（自発）
平成３年２月８日
特許庁長官 植 １） 敏 殿
■、事件の表示
平成０２年特許願第１８７８８４ 号２、発明の名称
芳香族ポリエーテルケトン系樹脂ワニスおよびその製造
方法
３、補正をする者
事件との関係 特許出願人
住所 東京都千代田区霞が関三丁目２番５号４、補正に
より増加する発明の数 零５、補正の対象
明細書の発明の詳細な説明の欄
６、補正の内容
（１）明細書第８頁下から第４行目に
とあるのを
と訂正する。Patent applicant Mitsui Toatsu Kagaku Co., Ltd. Procedural amendment (voluntary) February 8, 1991 Commissioner of the Patent Office Ue 1) Mr. Satoshi■, Case description 1990 Patent Application No. 187884 2, Name of invention Aromatic Polyetherketone resin varnish and its manufacturing method 3, relationship with the case of the person making the amendment Patent applicant address 3-2-5-4 Kasumigaseki, Chiyoda-ku, Tokyo Number of inventions increased by the amendment 0 5 Subject of the amendment Column 6 of Detailed Description of the Invention of the Specification, Contents of Amendment (1) The statement in the fourth line from the bottom of page 8 of the specification is corrected as follows.
」”
Claims (2)
し単位を有する芳香族ポリエーテルケトン系樹脂から選
ばれた１種または２種以上の混合物０．０１重量％〜３
０重量％を含む芳香族ポリエーテルケトン系樹脂ワニス ▲数式、化学式、表等があります▼（ I ） ▲数式、化学式、表等があります▼（II） ▲数式、化学式、表等があります▼（III） ▲数式、化学式、表等があります▼（IV） ▲数式、化学式、表等があります▼（Ｖ）(1) 0.01% to 3% by weight of one or a mixture of two or more aromatic polyetherketone resins having repeating units represented by the following general formulas (I) to (V)
Aromatic polyetherketone resin varnish containing 0% by weight III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V)
特徴とする請求項１記載のワニス（３）請求項（１）記
載の芳香族ポリエーテルケトン系樹脂から選ばれた１種
または２種以上の混合物０．０１重量％〜３０重量％を
含む芳香族ポリエーテルケトン系樹脂を、フェノール系
溶媒を用い、２０℃〜３００℃の温度で溶解して製造す
ることを特徴とする芳香族ポリエーテルケトン系樹脂ワ
ニスの製造方法。(2) The varnish according to claim 1, wherein the solvent of the varnish is a phenolic solvent. (3) One or two selected from the aromatic polyetherketone resins according to claim (1). An aromatic polyester is produced by dissolving an aromatic polyetherketone resin containing 0.01% to 30% by weight of the above mixture in a phenolic solvent at a temperature of 20°C to 300°C. A method for producing an ether ketone resin varnish.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18788490A JPH0476077A (en) | 1990-07-18 | 1990-07-18 | Aromatic polyether ketone-based resin varnish and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18788490A JPH0476077A (en) | 1990-07-18 | 1990-07-18 | Aromatic polyether ketone-based resin varnish and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0476077A true JPH0476077A (en) | 1992-03-10 |
Family
ID=16213887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18788490A Pending JPH0476077A (en) | 1990-07-18 | 1990-07-18 | Aromatic polyether ketone-based resin varnish and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0476077A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6869157B2 (en) | 2001-03-26 | 2005-03-22 | Canon Kabushiki Kaisha | Method of driving and controlling ink jet print head, ink jet print head, and ink jet printer |
| CN113583426A (en) * | 2021-09-09 | 2021-11-02 | 东华大学 | Preparation method of carbon fiber/polyether ketone composite material |
-
1990
- 1990-07-18 JP JP18788490A patent/JPH0476077A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6869157B2 (en) | 2001-03-26 | 2005-03-22 | Canon Kabushiki Kaisha | Method of driving and controlling ink jet print head, ink jet print head, and ink jet printer |
| CN113583426A (en) * | 2021-09-09 | 2021-11-02 | 东华大学 | Preparation method of carbon fiber/polyether ketone composite material |
| CN113583426B (en) * | 2021-09-09 | 2022-10-14 | 东华大学 | Preparation method of carbon fiber/polyether ketone composite material |
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