JPS6114164B2 - - Google Patents
Info
- Publication number
- JPS6114164B2 JPS6114164B2 JP14607276A JP14607276A JPS6114164B2 JP S6114164 B2 JPS6114164 B2 JP S6114164B2 JP 14607276 A JP14607276 A JP 14607276A JP 14607276 A JP14607276 A JP 14607276A JP S6114164 B2 JPS6114164 B2 JP S6114164B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polyester
- glycol
- soft
- mol
- 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
- 229920000728 polyester Polymers 0.000 claims description 21
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 14
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 230000005540 biological transmission Effects 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- -1 polytetramethylene Polymers 0.000 description 9
- 238000000034 method Methods 0.000 description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Gear Transmission (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
【発明の詳細な説明】
本発明は軟質ポリエステル動力伝達部品に関す
る。更に詳しくはテレフタル酸成分、デカンジカ
ルボン酸成分及びテトラメチレングリコール成分
からなるランダム共重合ポリエステルの動力伝達
部品に関する。
近年、射出成形等の溶融成形法によつて成形可
能な軟質樹脂が脚光を浴び、例えばテレフタル酸
とテトラメチレングリコール及びポリテトラメチ
レングリコールとから得られるブロツクポリエー
テルエステルが注目されている。しかしながら、
現在使用されている熱可塑性の軟質樹脂は一般的
に耐熱性が低く、あるものは100℃で軟化し、又
あるものは耐熱安定剤を多量使用する必要があ
る。
本発明者らは、かかる欠点のない軟質樹脂を見
出すべく検討を重ねた結果、デカンジカルボン酸
を特定量ランダム共重合せしめたポリブチレンテ
レフタレートは軟質で且つ耐熱性が高く、しかも
成形しやすく、これから得られる動力伝達部品は
高温雰囲気下で使用されても安定であり、音の発
生が少なく、機械的物性にすぐれることを見出し
本発明に至つたものである。
すなわち、本発明はテレフタル酸及びデカンジ
カルボン酸を酸成分とし、テトラメチレングリコ
ールをグリコール成分とするランダム共重合ポリ
エステルであつてデカンジカルボン酸成分が全ジ
カルボン酸成分当り、10〜50モル%含有されてお
り、且つ還元粘度(1.2g/100mlの濃度で35℃オ
ルクロルフエノール中で測定)が1.0以上である
ポリエステルを溶融成形してなる軟質ポリエステ
ル動力伝達部品に関する。
本発明で云う軟質ポリエステルは、テレフタル
酸,テトラメチレングリコール及びデカンジカル
ボン酸を構成成分とするポリエステルであるが、
このポリエステルは他の成分、例えばイソフタル
酸,フタル酸,ナフタレンジカルボン酸類,ジフ
エノキシエタンジカルボン酸類,ジフエニルジカ
ルボン酸類等の如き芳香族ジカルボン酸;アジピ
ン酸,セバチン酸,アゼライン酸,シクロヘキサ
ンジカルボン酸等の如き脂肪族又は脂環族ジカル
ボン酸;エチレングリコール,トリメチレングリ
コール,ヘキサメチレングリコール等の如き脂肪
族ジオール;ハイドロキノン,ビスフエノール類
及びこれらのグリコール付加物等の如き芳香族ジ
オール;オキシカプロン酸,オキシ安息香酸等の
如きオキシカルボン酸などを20モル%以下、好ま
しくは10モル%以下の量共重合したものであつて
もよい。
これらのポリエステルは、通常の、例えば溶融
重合法によつて製造されうる。例えばテレフタル
酸又はその低級アルキルエステルとデカンジカル
ボン酸又はその低級アルキルエステルとテトラメ
チレングリコールとをエステル化又はエステル交
換反応せしめ、しかる後反応生成物を減圧下に溶
融重合する方法、或いは上述の溶融重合を行なつ
た後に、更に固相重合する方法等によつて製造す
る事ができる。
上記軟質ポリエステルにはデカンジカルボン酸
が10〜50モル%、好ましくは20〜40モル%共重合
されている必要がある。デカンジカルボン酸以外
の成分、例えばアゼライン酸,セバチン酸等の脂
肪族ジカルボン酸を共重合しても軟質のポリエス
テルを得ることはできるが、この場合本発明の目
的を達成せんとすれば軟化点の低下が顕著となり
好ましくない。またデカンジカルボン酸の共重合
割合を10モル%未満にするとポリマーを軟質にす
る事が不充分であり、一方50モル%を越える割合
にすると成形の際結晶化速度が遅く又軟化点も低
くなるので好ましくない。
本発明の軟質ポリエステルは還元粘度が1.0以
上、好ましくは1.0〜3.0とする事が好ましい。こ
れより低い還元粘度の場合、成形品の引張強度等
機械的物性が低く、また耐熱性も低くなるので好
ましくない。
本発明においては、かかる軟質ポリエステルを
溶融成形して動力伝達部品とするのであるが、こ
の成形法は射出成形を使用することができる。こ
れらの成形条件は例えば溶融ゾーンのシリンダー
部温度が170〜240℃であり、金型等の冷却温度が
常温〜120℃とする条件をとることができる。又
溶融成形する前にポリエステルを乾燥する事は重
要であり、ポリエステル中の水分濃度を0.1wt%
以下とする事が好ましい。
かくして成形される軟質ポリエステル動力伝達
部品は、例えばギヤ,ジヨイント,カムである。
これらの成形素材として本発明の軟質ポリエステ
ルは極めて有用であり、該ポリエステルから成形
された動力伝達部品は次の如き特長を有する。
(a) 軟質であり、音の発生が少なく、又上述のポ
リエーテルエステルに比して表面硬度が同じ場
合に弾性率が高いので変形が少ない。
(b) 低温でも柔軟である。
(c) 耐熱性が高い。
(d) ガソリン,潤滑油,グリース等に対し耐性が
高い。
(e) 耐光性が良好である。
以下実施例により本発明を詳述する。尚、実施
例中の「部」は「重量部」である。
実施例 1
テレフタル酸136部,デカンジカルボン酸69部
(30モル%),テトラメチレングリコール190部及
び触媒量のチタニワムテトラブトキシサイドを反
応器に仕込み、240℃の温度でエステル化反応を
行なわせて、水を約70部留去せしめた後、240℃
で反応器を徐々に減圧にし、最終的に0.2mmHgと
して3時間重縮合せしめ、還元粘度1.35のポリエ
ステルを得た。
このポリエステルを140℃で4時間乾燥し、水
分率0.02%の乾燥チツプを得た。
この乾燥チツプを用い、シリンダー温度200
℃,金型温度60℃で射出成形を行なつて下記の成
形体を得た。
(1) 引張り試験用JIS3号ダンベル。
(2) 曲げ試験用1/4インチ厚の棒。
(3) 直径1cm,厚み1.5mmのギヤ。
これらの成形体を用いて行なつたテストの結果
を下表に示す。またポリテトラメチレングリコー
ル30重量%共重合したポリテトラメチレンテレフ
タレートを比較例として表に併記した。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to flexible polyester power transmission components. More specifically, the present invention relates to a power transmission part made of a random copolyester comprising a terephthalic acid component, a decanedicarboxylic acid component, and a tetramethylene glycol component. In recent years, soft resins that can be molded by melt molding methods such as injection molding have been in the spotlight, and for example, block polyether esters obtained from terephthalic acid, tetramethylene glycol, and polytetramethylene glycol have been attracting attention. however,
The thermoplastic soft resins currently in use generally have low heat resistance; some soften at 100°C, and others require the use of large amounts of heat stabilizers. As a result of repeated studies to find a soft resin that does not have these drawbacks, the present inventors found that polybutylene terephthalate, which is made by randomly copolymerizing a specific amount of decanedicarboxylic acid, is soft, has high heat resistance, and is easy to mold. The present invention was based on the discovery that the resulting power transmission component is stable even when used in a high-temperature atmosphere, generates little noise, and has excellent mechanical properties. That is, the present invention is a random copolymerized polyester containing terephthalic acid and decanedicarboxylic acid as acid components and tetramethylene glycol as a glycol component, in which the decanedicarboxylic acid component is contained in an amount of 10 to 50 mol% based on the total dicarboxylic acid component. The present invention relates to a soft polyester power transmission part made by melt-molding a polyester having a reduced viscosity (measured in ochlorophenol at 35° C. at a concentration of 1.2 g/100 ml) of 1.0 or more. The soft polyester referred to in the present invention is a polyester whose constituent components are terephthalic acid, tetramethylene glycol, and decanedicarboxylic acid.
This polyester may contain other components such as aromatic dicarboxylic acids such as isophthalic acid, phthalic acid, naphthalenedicarboxylic acids, diphenoxyethanedicarboxylic acids, diphenyldicarboxylic acids, etc.; adipic acid, sebacic acid, azelaic acid, cyclohexanedicarboxylic acid, etc. Aliphatic or alicyclic dicarboxylic acids such as; aliphatic diols such as ethylene glycol, trimethylene glycol, hexamethylene glycol, etc.; aromatic diols such as hydroquinone, bisphenols and their glycol adducts; oxycaproic acid, It may be copolymerized with oxycarboxylic acid such as oxybenzoic acid in an amount of 20 mol% or less, preferably 10 mol% or less. These polyesters can be produced by conventional methods, for example melt polymerization methods. For example, a method in which terephthalic acid or a lower alkyl ester thereof, decanedicarboxylic acid or a lower alkyl ester thereof, and tetramethylene glycol are subjected to an esterification or transesterification reaction, and then the reaction product is melt-polymerized under reduced pressure, or the above-mentioned melt polymerization After carrying out this process, it can be produced by further solid phase polymerization. The above-mentioned soft polyester needs to be copolymerized with decanedicarboxylic acid in an amount of 10 to 50 mol%, preferably 20 to 40 mol%. Although it is possible to obtain a soft polyester by copolymerizing components other than decanedicarboxylic acid, for example aliphatic dicarboxylic acids such as azelaic acid and sebacic acid, in this case, if the object of the present invention is not achieved, the softening point The decrease becomes significant, which is not preferable. Furthermore, if the copolymerization ratio of decanedicarboxylic acid is less than 10 mol%, it is insufficient to make the polymer soft, while if the ratio exceeds 50 mol%, the crystallization rate during molding will be slow and the softening point will be low. So I don't like it. The soft polyester of the present invention preferably has a reduced viscosity of 1.0 or more, preferably 1.0 to 3.0. If the reduced viscosity is lower than this, the mechanical properties such as tensile strength of the molded article will be low, and the heat resistance will also be low, which is not preferable. In the present invention, such a soft polyester is melt-molded to form a power transmission part, and injection molding can be used as the molding method. These molding conditions may be, for example, that the temperature of the cylinder part of the melting zone is 170 to 240°C, and the cooling temperature of the mold etc. is room temperature to 120°C. It is also important to dry the polyester before melt molding, and the moisture concentration in the polyester should be reduced to 0.1wt%.
It is preferable to do the following. The soft polyester power transmission parts molded in this manner are, for example, gears, joints, and cams.
The soft polyester of the present invention is extremely useful as a molding material for these materials, and power transmission parts molded from the polyester have the following features. (a) It is soft, generates less noise, and has a higher elastic modulus than the above-mentioned polyether ester when the surface hardness is the same, so it deforms less. (b) It is flexible even at low temperatures. (c) High heat resistance. (d) Highly resistant to gasoline, lubricating oil, grease, etc. (e) Good light resistance. The present invention will be explained in detail with reference to Examples below. Note that "parts" in the examples are "parts by weight." Example 1 136 parts of terephthalic acid, 69 parts of decanedicarboxylic acid (30 mol%), 190 parts of tetramethylene glycol, and a catalytic amount of titanium tetrabutoxide were charged into a reactor, and an esterification reaction was carried out at a temperature of 240°C. After distilling off about 70 parts of water, heat at 240°C.
The pressure in the reactor was gradually reduced to 0.2 mmHg and polycondensation was carried out for 3 hours to obtain a polyester with a reduced viscosity of 1.35. This polyester was dried at 140°C for 4 hours to obtain dry chips with a moisture content of 0.02%. Using this dry chip, the cylinder temperature is 200.
The following molded product was obtained by injection molding at a mold temperature of 60°C. (1) JIS No. 3 dumbbell for tensile testing. (2) 1/4 inch thick bar for bending test. (3) Gear with a diameter of 1cm and a thickness of 1.5mm. The results of tests conducted using these molded bodies are shown in the table below. Polytetramethylene terephthalate copolymerized with 30% by weight of polytetramethylene glycol is also listed in the table as a comparative example. 【table】
Claims (1)
分とし、テトラメチレングリコールをグリコール
成分とするランダム共重合ポリエステルであつ
て、該デカンジカルボン酸成分が全酸成分当り10
〜50モル%含有されており、且つ還元粘度(1.2
g/100mlの濃度で35℃、オルクロルフエノール
中で測定)が1.0以上であるポリエステルを溶融
成形してなる動力伝達部品。1 A random copolymerized polyester containing terephthalic acid and decanedicarboxylic acid as acid components and tetramethylene glycol as a glycol component, wherein the decanedicarboxylic acid component is 10% per total acid component.
It contains ~50 mol% and has a reduced viscosity (1.2
A power transmission part made by melt-molding polyester having a value of 1.0 or more (measured in ochlorophenol at 35°C at a concentration of g/100ml).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14607276A JPS5371195A (en) | 1976-12-07 | 1976-12-07 | Elastomeric polyester molded articles |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14607276A JPS5371195A (en) | 1976-12-07 | 1976-12-07 | Elastomeric polyester molded articles |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5371195A JPS5371195A (en) | 1978-06-24 |
JPS6114164B2 true JPS6114164B2 (en) | 1986-04-17 |
Family
ID=15399450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14607276A Granted JPS5371195A (en) | 1976-12-07 | 1976-12-07 | Elastomeric polyester molded articles |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5371195A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0632700U (en) * | 1992-10-05 | 1994-04-28 | 株式会社アイビス | Stepladder |
-
1976
- 1976-12-07 JP JP14607276A patent/JPS5371195A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0632700U (en) * | 1992-10-05 | 1994-04-28 | 株式会社アイビス | Stepladder |
Also Published As
Publication number | Publication date |
---|---|
JPS5371195A (en) | 1978-06-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3975487A (en) | Process for spinning high modulus oxybenzoyl copolyester fibers | |
JPH08508303A (en) | Copolymerization of dicarboxylic acids and dialkyl esters of dicarboxylic acids to form polyesters | |
EP0204528A1 (en) | Copolyester film and its production | |
EP0012763B1 (en) | Liquid crystal copolyesters | |
JPH0629316B2 (en) | Copolyetherester based on poly (propylene oxide) glycol blocked with ethylene oxide | |
US4201856A (en) | Liquid crystal copolyesters containing terephthalic acid, 2,6-naphthalenedicarboxylic acid, hydroquinone and resorcinol | |
US3592876A (en) | Thermoplastic polyester moulding compositions | |
JPS6114164B2 (en) | ||
JP4402232B2 (en) | Heat shrinkable polyester film | |
JP4662633B2 (en) | Blend of poly (1,3-propylene 2,6-naphthalate) | |
KR100658228B1 (en) | Biaxially oriented polyester film and preparation thereof | |
CA2489795A1 (en) | Copolymerization of cyclic ester oligomers | |
JPH06279579A (en) | Production of polyester and molded polyester object | |
JP4747444B2 (en) | Polyester film for metal lamination and metal laminate | |
JP2732481B2 (en) | Stretched polyester resin molded article, preform for stretched hollow molded article, and stretched hollow molded article | |
JP3080311B2 (en) | Polyester film | |
JPH05200864A (en) | Shape memory polyester molded article having heat generation properties | |
JP3303339B2 (en) | Modified polyester and method for producing the same | |
JPS60217234A (en) | Production of copolymerized polyester | |
JP3452401B2 (en) | Polyester film for food packaging | |
JP4570915B2 (en) | Polyester resin composition and molded product comprising the same | |
JPH06320621A (en) | Shrink film | |
JPH0245644B2 (en) | ||
JPS6038579B2 (en) | polyester gear | |
JPH0245645B2 (en) |