JPH04103667A - Saturated fatty acid glyceride composition - Google Patents

Saturated fatty acid glyceride composition

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Publication number
JPH04103667A
JPH04103667A JP22121890A JP22121890A JPH04103667A JP H04103667 A JPH04103667 A JP H04103667A JP 22121890 A JP22121890 A JP 22121890A JP 22121890 A JP22121890 A JP 22121890A JP H04103667 A JPH04103667 A JP H04103667A
Authority
JP
Japan
Prior art keywords
fatty acid
saturated fatty
acid glyceride
butyl
monoglyceride
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
Application number
JP22121890A
Other languages
Japanese (ja)
Inventor
Eiji Kamiryo
英二 上領
Hisashi Omoya
母家 寿
Kiyoshi Shinohara
清 篠原
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Riken Vitamin Co Ltd
Original Assignee
Riken Vitamin Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Riken Vitamin Co Ltd filed Critical Riken Vitamin Co Ltd
Priority to JP22121890A priority Critical patent/JPH04103667A/en
Publication of JPH04103667A publication Critical patent/JPH04103667A/en
Pending legal-status Critical Current

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  • Moulds For Moulding Plastics Or The Like (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

PURPOSE:To obtain the title resin having low volatility, exhibiting effects as lubricant, mold release agent, antistatic agent, etc., not causing mold stain and environmental pollution by uniformly blending a saturated fatty acid glyceride with a hindered phenolic compound in a molten state. CONSTITUTION:(A) 12-22C saturated fatty acid glyceride (e.g. stearic acid mono- or diglyceride; behenic acid monoglyceride) having preferably 50-100% monoglyceride content is blended in a molten state with (B) 0.05-2% hindered phenolic compound, an alkylphenol containing a substituent group (e.g tert.butyl group) having steric hindrance action at the ortho position, preferably triethylene glycol-bis[3-(3-tert.butyl-5-methyl-4-hydroxyphenyl)propionate] and optionally a phosphorus-based compound for preventing discoloration to give a saturated fatty acid glyceride.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は、主としてプラスチックの滑剤、離型剤、帯電
防止剤あるいは流滴剤として用いられる飽和脂肪酸グリ
セリド組成物に関するものである。
DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a saturated fatty acid glyceride composition used primarily as a lubricant, mold release agent, antistatic agent or droplet agent for plastics.

(従来の技術および発明の課題) プラスチックの滑剤、離型剤、帯電防止剤あるいは流滴
剤として用いられる飽和脂肪酸グリセリドは、他の配合
剤とともに加工前あるいは加工時にブレンドされ、押出
機、カレンダーロール、射出成型機等を使って成型され
る。しかし一般に加工温度が高いために、加工中に飽和
脂肪酸グリセリドが揮発し、効果不良を起こしたり、金
型汚染や環境汚染を生じたりして種々問題となっている
(Prior art and problems to be solved by the invention) Saturated fatty acid glycerides used as lubricants, mold release agents, antistatic agents, or droplet agents for plastics are blended with other ingredients before or during processing, and are used in extruders, calender rolls, etc. , molded using an injection molding machine, etc. However, because the processing temperature is generally high, saturated fatty acid glycerides volatilize during processing, causing various problems such as poor effectiveness, mold contamination, and environmental pollution.

本発明は、上記の問題に鑑みてなされたものであり、そ
の目的は揮発性が低く滑剤、離型剤、帯電防止剤等とし
ての効果が発揮され、かつ金型汚染や環境汚染を生じな
い飽和脂肪酸グリセリド組成物を提供することでる。
The present invention was made in view of the above-mentioned problems, and its purpose is to have low volatility, be effective as a lubricant, mold release agent, antistatic agent, etc., and not cause mold contamination or environmental pollution. A saturated fatty acid glyceride composition is provided.

(課題を解決するための手段および作用)従来から、不
飽和脂肪酸グリセリドにヒンダードフェノール系化合物
を添加することは、不飽和部位(二重結合)の自動酸化
防止あるいは加熱劣化防止の目的でよ〈実施されている
が、飽和脂肪酸グリセリドに揮発防止の目的でヒンダー
ドフェノール系化合物を添加する前例はない0本発明者
らは、プラスッチクの高温加工中の飽和脂肪酸グリセリ
ドが揮発することを防止する手段について。
(Means and effects for solving the problem) Adding hindered phenol compounds to unsaturated fatty acid glycerides has traditionally been used for the purpose of preventing autooxidation or heat deterioration of unsaturated sites (double bonds). (Although this has been done, there is no precedent for adding hindered phenol compounds to saturated fatty acid glycerides for the purpose of preventing volatilization.) The present inventors have attempted to prevent saturated fatty acid glycerides from volatilizing during high-temperature processing of plastics. About the means.

鋭意検討したところ、飽和脂肪酸グリセリドにヒンダー
ドフェノール系化合物を均一に溶融混合したものがその
目的に適う組成物であることを見比し1本発明を完成す
るに至った。
As a result of extensive research, it was determined that a composition in which a hindered phenol compound is uniformly melt-mixed with saturated fatty acid glyceride is a composition suitable for the purpose, and the present invention was completed.

即ち、本発明の要旨は「飽和脂肪酸グリセリドにヒンダ
ードフェノール系化合物を含有することを特徴とする飽
和脂肪酸グリセリド組成物」である。
That is, the gist of the present invention is "a saturated fatty acid glyceride composition characterized by containing a hindered phenol compound in a saturated fatty acid glyceride."

本発明に用いる飽和脂肪酸グリセリドは炭素数12〜2
2の飽和脂肪酸グリセリドである。即ちラウリン酸、ミ
リスチン酸、バルミチン酸、ステアリン酸、イソステア
リン酸、アラキシン酸、ベヘニン酸及び12−ヒドロキ
システアリン酸のそれぞれ単独あるいは混合物をグリセ
リンとエステル化するか、もしくはこれらの脂肪酸から
なる油脂またはメチルエステルをグリセリンとエステル
交換し、さらに必要ならば、これらの反応物を高真空蒸
溜してモノグリセリドだけを採取することによって得ら
れる。そして、これらの飽和脂肪酸グリセリド中のモノ
グリセリドの含量は、50〜100%の範囲のものが好
ましい。50%より低いと本来の機能である滑性、離型
性、帯電防止性あるいは流滴性が乏しくなって好ましく
ない、またモノグリセリド含量が50%より低くなるこ
とは、不揮発性化合物のジグリセリド、トリグリセリド
の含量が多くなることにつながり、揮発防止効果の度合
が低くなり好ましくない。
The saturated fatty acid glyceride used in the present invention has 12 to 2 carbon atoms.
2 saturated fatty acid glyceride. That is, lauric acid, myristic acid, valmitic acid, stearic acid, isostearic acid, araxic acid, behenic acid, and 12-hydroxystearic acid, each singly or as a mixture, are esterified with glycerin, or oils and fats or methyl esters made of these fatty acids are esterified with glycerin. is obtained by transesterifying with glycerin and, if necessary, distilling these reactants under high vacuum to collect only the monoglyceride. The monoglyceride content in these saturated fatty acid glycerides is preferably in the range of 50 to 100%. If the content is less than 50%, the original functions such as lubricity, mold release properties, antistatic properties, or droplet properties will become poor, which is undesirable.Moreover, if the monoglyceride content is less than 50%, it is not preferable that the monoglyceride content is less than 50%, which is due to the non-volatile compounds diglyceride and triglyceride. This leads to an increase in the content of , which is undesirable as it lowers the degree of volatilization prevention effect.

つぎに本発明に用いるヒンダードフェノール系化合物は
、オルト位に立体障害作用のある置換基(例えばter
t−ブチル基)をもったアルキルフェノールであり、特
に限定されるものではないが具体的にはトリエチレング
リコール−ビス[3−(3−t−ブチル−5−メチル−
4−ヒドロキシフェニル)プロピオネ−トコ、オクタデ
シル−3−(3,5−ジ−t−ブチル−4−ヒドロキシ
フェニル)プロピオネートあるいは3.5−ジ−t−ブ
チル−4−ヒドロキシベンジルフォスフォネート−ジエ
チルエステル等が好ましい、そしてヒンダードフェノー
ル系化合物の添加量は、飽和脂肪酸グリセリドに対して
0.05〜2.0%の範囲が好ましい、0.05%より
少ないと揮発防止効果が乏しくなる。また2、0%より
多く使用しても、揮発防止効果は1.5%〜2.0%の
ものと大差なく、むしろ着色したり、配合コストを上昇
させたりするので好ましくない。
Next, the hindered phenol compound used in the present invention has a substituent having a steric hindrance effect at the ortho position (for example, ter
It is an alkylphenol having a t-butyl group), and is not particularly limited, but specifically, triethylene glycol-bis[3-(3-t-butyl-5-methyl-
4-hydroxyphenyl)propionate, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate or 3,5-di-t-butyl-4-hydroxybenzylphosphonate-diethyl Ester and the like are preferred, and the amount of the hindered phenol compound added is preferably in the range of 0.05 to 2.0% based on the saturated fatty acid glyceride.If it is less than 0.05%, the volatilization prevention effect will be poor. Moreover, even if it is used in an amount of more than 2.0%, the volatilization prevention effect is not much different from that of 1.5% to 2.0%, but rather it causes coloring and increases the formulation cost, which is not preferable.

なお飽和脂肪酸グリセリドとヒンダードフェノール系化
合物との組み合わせによっては、強く着色する場合があ
り、このような時にはリン系化合物(例えばトリス(ノ
ニルフェニル)ホスファイト)を併用すれば着色は防止
できる。
Note that depending on the combination of saturated fatty acid glyceride and hindered phenol compound, strong coloring may occur, and in such cases, coloring can be prevented by using a phosphorus compound (for example, tris(nonylphenyl) phosphite) in combination.

以下実施例に基づいて本発明を説明を説明する。The present invention will be explained below based on Examples.

(実施例) (1)第1表に示す組成のものを100℃で10分間加
熱撹拌し、その後固化させたものを試験用サンプルとし
た。
(Example) (1) The composition shown in Table 1 was heated and stirred at 100° C. for 10 minutes, and then solidified to be used as a test sample.

第1表において飽和脂肪酸グリセリドは次のとおりであ
る。
In Table 1, the saturated fatty acid glycerides are as follows.

Aニステアリン酸モノグリセリド(モノグリセリド純度
=96%) Bニステアリン酸モノ、ジグリセリド(モノグリセリド
純度=52%) C:ベヘニン酸モノグリセリド(モノグリセリド純度=
93% D:12ヒドロキシステアリン酸モノグリセリド(モノ
グリセリド純度=93%) 第1表においてヒンダードフェノール系化合物は次のと
おりである。
A: Nystearic acid monoglyceride (monoglyceride purity = 96%) B: Nystearic acid mono-, diglyceride (monoglyceride purity = 52%) C: Behenic acid monoglyceride (monoglyceride purity =
93% D: 12-hydroxystearic acid monoglyceride (monoglyceride purity = 93%) In Table 1, the hindered phenol compounds are as follows.

aニトリエチレングリコール−ビス[3−(3−t−ブ
チル−5−メチル−4−ヒドロキシフェニル)プロピオ
ネート] b=ニオフタデシル3−(3,5〜ジーt−ブチル−4
−ヒドロキシフェニル)プロピオネート C:3.5−ジー上ブチル−4−ヒドロキシベンジルフ
オスフオネートージエチルエステル であり、同表のその他はトリスノニルフェニルフォスフ
ェートである。
a Nitriethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate] b = Niophtadecyl 3-(3,5-di-t-butyl-4
-Hydroxyphenyl)propionate C: 3.5-di-butyl-4-hydroxybenzyl phosphonate diethyl ester; others in the same table are trisnonylphenyl phosphate.

(2)第1表の各サンプル30gを、内径5cm高さ7
■のビーカーに精秤し、イーヤ−オーブン中で、180
℃および230℃で、30分および60分間加熱し、各
サンプルの揮発減量、着色度並びにモノグリセリド純度
を測定した。その結果を第2表に示す。
(2) Take 30g of each sample in Table 1 and
Weigh it accurately in a beaker and place it in an oven at 180℃.
The samples were heated at 230°C and 230°C for 30 and 60 minutes, and the loss of volatile matter, degree of coloration, and monoglyceride purity of each sample were measured. The results are shown in Table 2.

(3)ポリプロピレン(pp)樹脂(三井石油化学製ハ
イボールJ−300)に、第1表に示した各サンプルを
、樹脂100部に対し5部の割合で添加し、ラボプラス
トミルT台押出機(成型温度二Tl/T2/T3/ダイ
ス−150℃/170℃7200℃7230℃)を使用
して、厚さ0.02〜0.03nnのフィルムを作成し
た。
(3) Add each sample shown in Table 1 to polypropylene (PP) resin (Mitsui Petrochemical Highball J-300) at a ratio of 5 parts to 100 parts of the resin, and extrude it on the Labo Plastomill T-stand. A film having a thickness of 0.02 to 0.03 nn was produced using a molding machine (molding temperature: 2 Tl/T2/T3/Dice: 150°C/170°C, 7200°C, 7230°C).

1検体につき60分間連続運転し、ダイス出口近傍上側
に取付けた鏡面の汚れ度合並びにフィルムの着色度を観
察した。その結果を第3表に示す。
Each sample was operated continuously for 60 minutes, and the degree of dirt on the mirror surface attached above the die exit and the degree of coloration of the film were observed. The results are shown in Table 3.

本発明品1〜3と比較量1〜2、本発明品4と比較量3
、本発明品5と比較量4および本発明品6と比較量5の
対比において、第2表の180℃および230℃におけ
る揮発減量は、いずれも本発明品の方が半量以下と低く
なっている。また第3表のPPの加工試験においても、
いずれも本発明品の方が鏡面の汚れが少なくなっている
ことが明らかである。
Inventive products 1 to 3 and comparative amounts 1 to 2, inventive products 4 and comparative amount 3
Comparing Inventive Product 5 with Comparative Amount 4 and Inventive Product 6 with Comparative Amount 5, the volatilization loss at 180°C and 230°C in Table 2 was lower for the Inventive Product at less than half the amount. There is. Also, in the PP processing test shown in Table 3,
In both cases, it is clear that the product of the present invention has less dirt on the mirror surface.

(発明の効果) 本発明によれば、飽和脂肪酸グリセリドの揮発減量が少
なく、滑剤、離型剤、帯電防止剤あるいは流滴剤として
の効果が発揮され、かつ金型汚染や環境汚染を生じない
ので、その実用上の価値は大なるものがある。
(Effects of the Invention) According to the present invention, the volatilization loss of saturated fatty acid glyceride is small, and the effect as a lubricant, mold release agent, antistatic agent, or droplet agent is exhibited, and no mold contamination or environmental pollution occurs. Therefore, its practical value is great.

Claims (4)

【特許請求の範囲】[Claims] (1)飽和脂肪酸グリセリドにヒンダードフェノール系
化合物を含有することを特徴とする飽和脂肪酸グリセリ
ド組成物。
(1) A saturated fatty acid glyceride composition characterized by containing a hindered phenol compound in the saturated fatty acid glyceride.
(2)飽和脂肪酸グリセリド中のモノグリセリド含有が
、50〜100%である請求項(1)記載の飽和脂肪酸
グリセリド組成物。
(2) The saturated fatty acid glyceride composition according to claim 1, wherein the monoglyceride content in the saturated fatty acid glyceride is 50 to 100%.
(3)ヒンダードフェノール系化合物がトリエチレング
リコール−ビス[3−(3−t−ブチル−5−メチル−
4−ヒドロキシフェニル)プロピオネート]、オクタデ
シル−3−(3、5−ジ−t−ブチル−4−ヒドロキシ
フェニル)プロピオネート、3、5−ジ−t−ブチル−
4−ヒドロキシベンジルフォスフォネート−ジエチルエ
ステルのうち何れか一つ以上である請求項(1)記載の
飽和脂肪酸グリセリド組成物。
(3) The hindered phenol compound is triethylene glycol-bis[3-(3-t-butyl-5-methyl-
4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 3,5-di-t-butyl-
The saturated fatty acid glyceride composition according to claim 1, which is any one or more of 4-hydroxybenzylphosphonate-diethyl ester.
(4)ヒンダードフェノール系化合物が飽和脂肪酸グリ
セリドに対して0.05〜2.0%の割合で含有する請
求項(1)記載の飽和脂肪酸グリセリド組成物。
(4) The saturated fatty acid glyceride composition according to claim 1, wherein the hindered phenol compound is contained in a proportion of 0.05 to 2.0% based on the saturated fatty acid glyceride.
JP22121890A 1990-08-24 1990-08-24 Saturated fatty acid glyceride composition Pending JPH04103667A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP22121890A JPH04103667A (en) 1990-08-24 1990-08-24 Saturated fatty acid glyceride composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22121890A JPH04103667A (en) 1990-08-24 1990-08-24 Saturated fatty acid glyceride composition

Publications (1)

Publication Number Publication Date
JPH04103667A true JPH04103667A (en) 1992-04-06

Family

ID=16763317

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22121890A Pending JPH04103667A (en) 1990-08-24 1990-08-24 Saturated fatty acid glyceride composition

Country Status (1)

Country Link
JP (1) JPH04103667A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6117922A (en) * 1997-03-21 2000-09-12 Clariant Gmbh Solid, storage-stable antistat mixtures and process for their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6117922A (en) * 1997-03-21 2000-09-12 Clariant Gmbh Solid, storage-stable antistat mixtures and process for their preparation

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