JPS5810422B2 - How to use the technology - Google Patents
How to use the technologyInfo
- Publication number
- JPS5810422B2 JPS5810422B2 JP11535575A JP11535575A JPS5810422B2 JP S5810422 B2 JPS5810422 B2 JP S5810422B2 JP 11535575 A JP11535575 A JP 11535575A JP 11535575 A JP11535575 A JP 11535575A JP S5810422 B2 JPS5810422 B2 JP S5810422B2
- Authority
- JP
- Japan
- Prior art keywords
- aging agent
- aqueous solution
- polymeric anti
- product
- spherical
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 230000003712 anti-aging effect Effects 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012768 molten material Substances 0.000 description 2
- -1 polyoxyethylene lauryl ether Polymers 0.000 description 2
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VORLTHPZWVELIX-UHFFFAOYSA-N 1-methyl-2h-quinoline Chemical compound C1=CC=C2N(C)CC=CC2=C1 VORLTHPZWVELIX-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PVMNBWXRCLEDCL-UHFFFAOYSA-N acetaldehyde;aniline Chemical compound CC=O.NC1=CC=CC=C1 PVMNBWXRCLEDCL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Glanulating (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
【発明の詳細な説明】
本発明はゴム用の重合系老化防止剤の球状製品の製造法
に関し、更に詳しくは溶融した重合系老化防止剤を、界
面活性剤を含む水溶液中に添加、分散させ、急冷固化せ
しめることからなる重合系老化防止剤の球状製品の製造
法であって、その目的とするところは流動性にすぐれ、
かつ崩壊性の少ない球状品を得んとするところにある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a spherical product of a polymeric anti-aging agent for rubber, and more specifically, a method for producing a spherical product of a polymeric anti-aging agent for rubber, and more specifically, a process in which a molten polymeric anti-aging agent is added and dispersed in an aqueous solution containing a surfactant. , a method for producing a spherical product of a polymeric anti-aging agent, which consists of rapid cooling and solidification, the purpose of which is to have excellent fluidity,
The aim is to obtain a spherical product with low disintegration.
ゴム用の耐熱性老化防止剤として広く使用されているア
セトアルデヒド−アニリンの反応物、フェノール−アル
デヒド−アミンの縮合物、２，２゜４−トリメチル−１
，２−ジヒドロキノリン重合物、フェニル−β−ナフチ
ルアミンとアセトンの反応物、フェノール縮合物等の常
温で固体の重合系老化防止剤は粉末品、フレーク品等の
製品形態で市販されているが、粉末品では使用時に粉塵
が飛散したりして作業環境を著しく汚染し、またフレー
ク品でもそれが非常に崩壊し易いためにたとえば輸送途
中で粉末化して前記と同様の作業環境の悪化が問題とな
っている。Acetaldehyde-aniline reaction product, phenol-aldehyde-amine condensate, 2,2゜4-trimethyl-1, which is widely used as a heat-resistant anti-aging agent for rubber.
, 2-dihydroquinoline polymers, reaction products of phenyl-β-naphthylamine and acetone, and phenol condensates, polymeric anti-aging agents that are solid at room temperature are commercially available in product forms such as powders and flakes. Powder products scatter dust during use, contaminating the working environment significantly, and flake products also disintegrate very easily, causing the same problem of deterioration of the working environment as described above if they turn into powder during transportation. It has become.
また近年タイヤの製造その他ゴム工業においてオートメ
ーション化が普及して配合過程における自動化が進み、
これにともなって老化防止剤を連続的かつ一定量づつ計
量供給する必要性が生じた。In addition, automation has become widespread in tire manufacturing and other rubber industries in recent years, and automation in the compounding process has progressed.
This has created a need to continuously and meteredly supply anti-aging agents in fixed amounts.
しかし粉末品、フレーク品は共に流動性に乏しく連続的
且つ一定量づつ計量供給するのは困難であり流動性が優
れ且つ粉塵の生じない球状の製品に対する必要性が高ま
った。However, both powder products and flake products have poor fluidity and are difficult to meter and supply continuously and in fixed amounts.Therefore, there has been a growing need for spherical products that have excellent fluidity and do not generate dust.
老化防止剤を球状にする方法としては造粒機を使用する
方法、成型機を使用する方法が考えられる。Possible methods for making the anti-aging agent into spheres include using a granulator and using a molding machine.
しかしこれらの方法は特殊な機械を必要とし又生産能力
を高めるためには莫大な設備投資を必要とする。However, these methods require special machinery and require huge capital investment to increase production capacity.
また親水性高分子を含む水溶液中に溶融させたアミン系
老化防止剤を混合攪拌して分散粒子を作り、これを攪拌
しながら冷却して固化させる方法（特公昭４８−３２１
０号）も知られているが、該方法はたとえばＮ−フェニ
ル−α（もしくは−β）−ナフチルアミンやＮ−インプ
ロピル−Ｎ’−フェニル−ｐ−フェニレンジアミンのよ
うないわゆる単量体構造からなる比較的低分子量の化合
物には適用し得ても、前記したような常温で固型の重合
系老化防止剤に適用した場合には、これらの化合物が一
般に軟化点（もしくは凝固点）の幅が広いこともあって
冷却するに伴って分散粒子の粘度が高くなって機械的な
攪拌などで一定の粒子形が保てず、糸状あるいは帯状に
なり、更に冷却すると全体が固化してしまうなどして、
球状の製品を得ることは極めて困難である。Alternatively, an amine antioxidant dissolved in an aqueous solution containing a hydrophilic polymer is mixed and stirred to form dispersed particles, which are then cooled and solidified while stirring (Japanese Patent Publication No. 48-321
No. 0) is also known, but this method can be used to prepare monomeric structures such as N-phenyl-α (or -β)-naphthylamine and N-impropyl-N'-phenyl-p-phenylenediamine. However, when applied to the above-mentioned polymeric anti-aging agents that are solid at room temperature, these compounds generally have a wide range of softening points (or freezing points). Because the particles are wide, the viscosity of the dispersed particles increases as they cool, making it impossible to maintain a constant particle shape with mechanical stirring, resulting in string-like or band-like shapes, and when cooled further, they solidify as a whole. hand,
It is extremely difficult to obtain spherical products.
このようなことから本発明者らは従来球状化しにくいと
されていた常温で固体状の重合系老化防止剤を安価に、
容易に球状化する方法について鋭意検討した結果、本発
明を完成するに至った。For these reasons, the present inventors have developed an inexpensive polymeric anti-aging agent that is solid at room temperature, which was previously thought to be difficult to form into spheres.
As a result of intensive research into a method for easily spheroidizing, the present invention has been completed.
すなわち本発明は溶融した重合系老化防止剤を界面活性
剤を含む水溶液中に添加、分散させ、急冷固化せしめる
ことからなる重合系老化防止剤の球状製品の製造方法で
ある。That is, the present invention is a method for producing a spherical product of a polymeric anti-aging agent, which comprises adding and dispersing a molten polymeric anti-aging agent in an aqueous solution containing a surfactant, and rapidly cooling and solidifying the solution.
本発明に適用される重合系老化防止剤とは前述したよう
な常温で固体の重合系の化合物であるが、特に２，２．
４−トリメチル−１，２−ジヒドロキノリン重合物、フ
ェニル−β−ナフチルアミンとアセトンの反応物が本発
明に有効に適用される。The polymeric anti-aging agent applied to the present invention is a polymeric compound that is solid at room temperature as described above, and in particular, 2, 2.
A 4-trimethyl-1,2-dihydroquinoline polymer, a reaction product of phenyl-β-naphthylamine and acetone are effectively applied to the present invention.
また本発明に用いる界面活性剤としては特に制限はなく
、非イオン性、陰イオン性、陽イオン性の従来公知の各
種界面活性剤が使用でき、たとえはポリオキシエチレン
ラウリルエーテル、ドデシルベンゼンスルホン酸ナトリ
ウム、ラウリルアミンアセテート等が例示される。The surfactant used in the present invention is not particularly limited, and various conventionally known nonionic, anionic, and cationic surfactants can be used, such as polyoxyethylene lauryl ether, dodecylbenzenesulfonic acid, etc. Examples include sodium and laurylamine acetate.
この界面活性剤の使用量には特に制限はないが、その量
があまりに少ない場合にはその効果が充分に得られず、
溶融した重合系老化防止剤（以下単に溶融物と呼ぶこと
もある。There is no particular limit to the amount of this surfactant used, but if the amount is too small, the effect will not be sufficiently obtained.
Melted polymeric anti-aging agent (hereinafter sometimes simply referred to as melt).
）がうまく分散されずに水溶液表面で広がって製品が板
状になったり、柱状になったりして球状品が得られなく
なる恐れがあり、またあまり多量に用いては不経済でも
あり、一般には水溶液中に０．０１〜２重量係景気とな
るように添加される。) may not be well dispersed and spread on the surface of the aqueous solution, resulting in the product becoming plate-like or columnar, making it impossible to obtain a spherical product.It is also uneconomical to use too large a quantity; It is added to the aqueous solution in an amount of 0.01 to 2 weight percent.
本発明における前記界面活性剤を含む水溶液は溶融物を
水溶液中で同時に急冷固化する働きをも兼ねることから
、その温度は適用される重合系老化防止剤の凝固点以下
、好ましくは５０℃以下に保持することが必要である。Since the aqueous solution containing the surfactant in the present invention also has the function of rapidly solidifying the molten material in the aqueous solution, the temperature thereof is maintained below the freezing point of the applied polymeric anti-aging agent, preferably below 50°C. It is necessary to.
溶融物を水溶液中に添加する方法には特に制限はなく任
意であるが、ノズルの形式と注入する圧力を選択するこ
とにより製品の直通がコントロールできるという利点か
ら、ノズルにより液中に直接注入するか、滴下する方法
が好ましい。There are no particular restrictions on the method of adding the molten material into the aqueous solution, and it is arbitrary; however, direct injection into the liquid through a nozzle has the advantage of controlling the direct flow of the product by selecting the nozzle type and injection pressure. Or dropwise method is preferable.
本発明を実施するにあたっては界面活性剤を含む水溶液
に機械的攪拌を与えることは非常に有効であり、また流
水法などにより分散急冷固化せしめると共に連続的に製
品を排出する方法もまた有効である。In carrying out the present invention, it is very effective to provide mechanical agitation to the aqueous solution containing the surfactant, and it is also effective to disperse and rapidly solidify the solution using a water flow method, etc., and to continuously discharge the product. .
本発明の方法によれは溶融した重合系老化防止剤は水溶
液中で分散されると共に急冷固化するために分散物同志
の再付着現象もなく、従って再付着を防止するための別
種の薬剤を何ら必要とすることなく粒状化が可能となり
、かくして得られた粒状物を水溶液から分離したのち洗
浄、乾燥すれば直径約０５〜５ｍｍ程度の流動性にすぐ
れ、かつ崩壊性の非常に少ない球状製品が得られる。According to the method of the present invention, since the molten polymeric anti-aging agent is dispersed in an aqueous solution and solidified by rapid cooling, there is no redeposition phenomenon between the dispersions, and therefore no other type of agent is used to prevent redeposition. By separating the granules thus obtained from the aqueous solution, washing and drying, a spherical product with a diameter of about 0.5 to 5 mm, excellent fluidity, and very low disintegration can be obtained. can get.
以下に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
ドデシルベンゼンスルホン酸ソーダを０．０５重景気含
有する水溶液５００ｇを攪拌しながら５０℃以下に冷却
し、溶融した２、２．４−トリメチル−１，２−ジヒド
ロキノリン重合物１００ｇを滴下した。Example 1 500 g of an aqueous solution containing 0.05 g of sodium dodecylbenzenesulfonate was cooled to below 50°C with stirring, and 100 g of molten 2,2,4-trimethyl-1,2-dihydroquinoline polymer was added dropwise. did.
滴下終了後直ちに球状物をろ過、水洗、乾燥すると流動
性にすぐれ崩壊性の少ない直径０．８〜４ｍｍの大きさ
の球状品９８ｇが得られた。Immediately after the completion of the dropwise addition, the spherical product was filtered, washed with water, and dried to obtain 98 g of a spherical product with a diameter of 0.8 to 4 mm and excellent fluidity and low disintegrability.
実施例 ２
５００１ビーカーの底部送入口からポリオキシエチレン
ラウリルエーテル０．０５％含有する水溶液を２００
ｌ ／ｍの流速で連続的に流入しビーカーの一端からオ
ーバーフローするようになってから溶融した２、 ２．
４−トＩＪメチルー１，２−ジヒドロキノリン重合物を
ビーカー上部から５ Ｋｇ／ｍｉｎの速度で連続的に滴
下した。Example 2 An aqueous solution containing 0.05% polyoxyethylene lauryl ether was poured into a 5001 beaker from the bottom inlet.
2. It flowed continuously at a flow rate of l/m and melted after overflowing from one end of the beaker.2.
The 4-toIJ methyl-1,2-dihydroquinoline polymer was continuously added dropwise from the top of the beaker at a rate of 5 kg/min.
生成した粒状物はオーバフローする水溶液と共に排出さ
れるのでこれをろ過して粒状物を分離し、水洗、乾燥す
ると直径０．８ｍｍから３．３ｍｍの大きさの流動性に
すぐれ、崩壊性の少ない球状品が得られた。The generated granules are discharged together with the overflowing aqueous solution, so they are filtered to separate the granules, washed with water, and dried to form spherical particles with diameters ranging from 0.8 mm to 3.3 mm with excellent fluidity and low collapsibility. Goods were obtained.
実施例 ３
重合系老化防止剤としてフェニル−β−ナフチルアミン
とアセトンとの反応物を用いる以外は実施例１と全く同
様にして粒状化を行ったところ、流動性にすぐれ、崩壊
性の少ない直径０．８〜３ｗ／ｌの球状品９８ｇが得ら
れた。Example 3 Particles were granulated in the same manner as in Example 1 except that a reaction product of phenyl-β-naphthylamine and acetone was used as a polymeric anti-aging agent. 98 g of spherical articles of .8-3 w/l were obtained.
Claims (1)
溶液中に添加、分散させ、急冷固化せしめることを特徴
とする重合系老化防止剤の球状製品の製造法。1. A method for producing a spherical product of a polymeric anti-aging agent, which comprises adding and dispersing a molten polymeric anti-aging agent in an aqueous solution containing a surfactant, and rapidly solidifying the polymeric anti-aging agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11535575A JPS5810422B2 (en) | 1975-09-23 | 1975-09-23 | How to use the technology |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11535575A JPS5810422B2 (en) | 1975-09-23 | 1975-09-23 | How to use the technology |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5239738A JPS5239738A (en) | 1977-03-28 |
| JPS5810422B2 true JPS5810422B2 (en) | 1983-02-25 |
Family
ID=14660465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11535575A Expired JPS5810422B2 (en) | 1975-09-23 | 1975-09-23 | How to use the technology |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5810422B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6012317Y2 (en) * | 1980-09-26 | 1985-04-20 | 安立電気株式会社 | Panel mounting structure |
| US5171938A (en) * | 1990-04-20 | 1992-12-15 | Yazaki Corporation | Electromagnetic wave fault prevention cable |
| JP5330904B2 (en) * | 2009-06-12 | 2013-10-30 | 住友化学株式会社 | Method for producing granular material |
-
1975
- 1975-09-23 JP JP11535575A patent/JPS5810422B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5239738A (en) | 1977-03-28 |
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