JP2010001384A - Additive for resin, and masterbatch or resin composition containing same, and molded article - Google Patents

Additive for resin, and masterbatch or resin composition containing same, and molded article Download PDF

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JP2010001384A
JP2010001384A JP2008161573A JP2008161573A JP2010001384A JP 2010001384 A JP2010001384 A JP 2010001384A JP 2008161573 A JP2008161573 A JP 2008161573A JP 2008161573 A JP2008161573 A JP 2008161573A JP 2010001384 A JP2010001384 A JP 2010001384A
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resin
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JP5208592B2 (en
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Soichiro Kamiya
宗一郎 神谷
Hitoshi Matsui
仁司 松井
Kimio Yoshikawa
公夫 吉川
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Riken Vitamin Co Ltd
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an additive for resin to improve antistatic property, anti-fogging property, and filler dispersibility. <P>SOLUTION: The present invention is an additive for resin which is characterized in that (1) the additive used by being added to the resin contains a polyglycerine alkyl ether compound having a particular structure; (2) the additive further contains an anionic surfactant; (3) the resin is at least one selected from polyethylene, polypropylene, ethylene-vinyl acetate copolymer, vinyl chloride, and polylactic acid. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

本発明は帯電防止性、防曇性、フィラーの分散性改善に優れ且つ加工時の安定性に優れた樹脂用添加剤及びこれを含むマスターバッチ又は樹脂組成物並びに成形品に関する。   The present invention relates to an additive for resins excellent in antistatic properties, antifogging properties, filler dispersibility improvement and stability during processing, and a masterbatch or resin composition containing the same, and a molded article.

一般に使用されているプラスチックの多くは極性が低く、通常の室温、湿度条件下で容易に帯電したり、結露を生じたりしやすい。プラスチックが帯電すると、生産工程上の障害となったり、製品に汚れが付着したり、印刷不良が起きたりする。また、ラップフィルム等の食品包装材料では結露が生じるとフィルム表面が結露により曇り内容物が確認できないなどの問題が生じる。農業用フィルムでは結露が生じると日光の透過率が低下し作物の生育が悪くなったり、水滴が作物に落下し病虫害が発生したりする問題が生じる。また、樹脂(プラスチック)の剛性や耐衝撃、耐熱性などの向上の目的で炭酸カルシウム、タルクやガラスファイバーなどのフィラーを充填することが一般的に行われるが、これらのフィラーはプラスチックとの相溶性が悪い事が多く、樹脂中に十分に分散されずに満足できる効果が得られなかったり、加工時にフィラーの分散不良により、ムラが出来たりして不良が発生する事がある。   Many commonly used plastics have low polarity, and are easily charged or dewed easily under normal room temperature and humidity conditions. If the plastic is charged, it may be an obstacle to the production process, dirt may be attached to the product, and printing defects may occur. In addition, when a food packaging material such as a wrap film has dew condensation, there is a problem that the film surface cannot be clouded due to dew condensation. In the film for agriculture, when dew condensation occurs, there is a problem that the transmittance of sunlight is lowered and the growth of the crop is deteriorated, or water drops fall on the crop to cause pest damage. In addition, fillers such as calcium carbonate, talc, and glass fiber are generally filled for the purpose of improving the rigidity, impact resistance, and heat resistance of the resin (plastic). These fillers are compatible with plastics. In many cases, the solubility is poor and a satisfactory effect cannot be obtained without being sufficiently dispersed in the resin, or unevenness may occur due to poor dispersion of the filler during processing, resulting in failure.

これらの問題を解決するために一般に帯電防止剤や防曇剤、分散剤といった樹脂用添加剤を樹脂中に含有せしめて、樹脂表面を親水化したり樹脂とフィラーの界面を相溶化することが行われる。このような樹脂用添加剤としては低分子の界面活性剤が常用されている。   In order to solve these problems, resin additives such as antistatic agents, antifogging agents, and dispersing agents are generally included in the resin to make the resin surface hydrophilic or to make the interface between the resin and filler compatible. Is called. As such a resin additive, a low molecular surfactant is commonly used.

樹脂用添加剤として用いられる界面活性剤をイオン性別に分類するとアニオン系、カチオン系、ノニオン系、両性系に分けられる。これらの内、アニオン系は表面親水化効果があまり大きくない。カチオン系、両性系のものは表面親水化効果は大きいものの耐熱性が低く、着色などの問題が起きやすい。ノニオン系のものも表面親水化効果はあまり大きくないが、分子構造上、親水基の付加モル数や疎水基の鎖長の調整により親水性・疎水性バランスの調整がしやすく、様々な樹脂に適用しやすいこと、着色などの問題も起きにくいことから、樹脂用添加剤として単独でまた、アニオン系やカチオン系との併用により用いられている。
ポリエステル樹脂の耐熱性改善の目的で、ポリオキシエチレンアルキルエーテル又はポリグリセリン脂肪酸エステルを用いる方法(例えば、特許文献1参照)、及びポリエステル樹脂の帯電防止剤としてポリグリセリン脂肪酸エステルを用いる方法(例えば、特許文献2参照)が開示されているが、その効果の持続性の面では十分とはいえない。
Surfactants used as additives for resins are classified into anionic, cationic, nonionic, and amphoteric types when classified according to ionicity. Among these, the anionic system does not have a significant surface hydrophilizing effect. Cationic and amphoteric ones have a large surface hydrophilizing effect but have low heat resistance and are susceptible to problems such as coloring. Nonionic type also has a surface hydrophilization effect that is not so great, but due to the molecular structure, it is easy to adjust the hydrophilic / hydrophobic balance by adjusting the number of moles of hydrophilic groups added and the chain length of hydrophobic groups. Since it is easy to apply and problems such as coloring do not easily occur, it is used alone as a resin additive or in combination with an anionic or cationic one.
For the purpose of improving the heat resistance of the polyester resin, a method using a polyoxyethylene alkyl ether or a polyglycerol fatty acid ester (for example, see Patent Document 1), and a method using a polyglycerol fatty acid ester as an antistatic agent for a polyester resin (for example, Patent Document 2) is disclosed, but it is not sufficient in terms of sustainability of the effect.

ノニオン系界面活性剤としてはアルキルアミンのエチレンオキサイド付加物やアルキルアミドのエチレンオキサイド付加物が効果の高いものとして用いられるが、分子内に窒素原子を含有しており、樹脂の黄変を発生しやすい。また、高級アルコールやグリセリン脂肪酸エステル、ソルビタン脂肪酸エステルなどのエチレンオキサイド付加物も樹脂用添加剤として用いる事ができるが、樹脂によっては十分な効果が見られなかったり、効果の持続性が劣る場合がある。その他にもノニオン系界面活性剤としてはステアリン酸モノグリセライドが常用されているが、ステアリン酸モノグリセライドはアニオン系、カチオン系、窒素含有ノニオン系などの界面活性剤との併用時に分解し、不都合が生じる。
特開2007−246623号公報 特開2007−126500号公報
As nonionic surfactants, ethylene oxide adducts of alkylamines and ethylene oxide adducts of alkylamides are used as highly effective substances, but they contain nitrogen atoms in the molecule and cause yellowing of the resin. Cheap. Also, ethylene oxide adducts such as higher alcohols, glycerin fatty acid esters, and sorbitan fatty acid esters can be used as additives for resins, but depending on the resin, sufficient effects may not be seen or the sustainability of the effects may be poor. is there. In addition, stearic acid monoglyceride is commonly used as a nonionic surfactant, but stearic acid monoglyceride is decomposed when used in combination with anionic, cationic, or nitrogen-containing nonionic surfactants, resulting in inconvenience.
JP 2007-246623 A JP 2007-126500 A

本発明の目的は、帯電防止性、防曇性、フィラーの分散性改善に優れ且つ加工時の安定性に優れた樹脂用添加剤及びこれを含むマスターバッチ又は樹脂組成物並びに成形品を提供することにある。   An object of the present invention is to provide an additive for a resin that is excellent in antistatic properties, antifogging properties, improved dispersibility of fillers, and has excellent stability during processing, and a masterbatch or a resin composition containing the same, and a molded article. There is.

本発明者らは、上記課題について鋭意研究を重ねた結果、特定の構造を持つ化合物を含有する樹脂用添加剤を樹脂に配合した場合に、優れた表面親水化効果をもつことを突き止め、また、同樹脂用添加剤が安定性、加工性において優れた特性を有する事を見出し、本発明を完成するに至った。
即ち、本発明は以下の構成を有する。
1.樹脂に添加されて用いられる樹脂用添加剤において、下記式(1)で表される化合物を含有することを特徴とする樹脂用添加剤。
RO−(A)n−H (1)
(式中、Rは炭素数8〜22のアルキル基、nは平均値が1〜20、Aは−CHCHOHCHO−、−CHCH(CHOH)O−で示されるいずれかの基を表す。)
2.アニオン系界面活性剤を併せ含有することを特徴とする前記1に記載の樹脂用添加剤。
3.樹脂が、ポリエチレン、ポリプロピレン、エチレン酢酸ビニル共重合体、塩化ビニル、ポリ乳酸から選ばれる少なくとも1つであることを特徴とする前記1又は2に記載の樹脂用添加剤。
4.式(1)で表される化合物を5〜20質量%含む前記1〜3のいずれかに記載の樹脂用添加剤を含有することを特徴とするマスターバッチ。
5.式(1)で表される化合物を0.1〜20質量%含む前記1〜3のいずれかに記載の樹脂用添加剤を含有することを特徴とする樹脂組成物。
6.前記5に記載の樹脂組成物を成形してなる成形品。
As a result of intensive research on the above problems, the present inventors have found that when a resin additive containing a compound having a specific structure is blended with a resin, it has an excellent surface hydrophilizing effect, The present inventors have found that the resin additive has excellent characteristics in stability and processability, and have completed the present invention.
That is, the present invention has the following configuration.
1. The additive for resin containing the compound represented by following formula (1) in the additive for resin used by adding to resin.
RO- (A) n-H (1)
(In the formula, R is an alkyl group having 8 to 22 carbon atoms, n is an average value of 1 to 20, and A is any one of —CH 2 CHOHCH 2 O— and —CH 2 CH (CH 2 OH) O—. Represents a group of
2. 2. The additive for resin as described in 1 above, which further contains an anionic surfactant.
3. 3. The resin additive as described in 1 or 2 above, wherein the resin is at least one selected from polyethylene, polypropylene, ethylene vinyl acetate copolymer, vinyl chloride, and polylactic acid.
4). The masterbatch characterized by containing the additive for resin in any one of said 1-3 which contains 5-20 mass% of compounds represented by Formula (1).
5). A resin composition comprising the resin additive as described in any one of 1 to 3 above, containing 0.1 to 20% by mass of the compound represented by the formula (1).
6). 6. A molded product obtained by molding the resin composition as described in 5 above.

上記の説明から明らかなように、本発明により表面親水化効果が高く、且つ加工性、安定性に優れ、機械物性の低下や加工時の分解も少なく着色を抑制できる樹脂用添加剤及びこれを含むマスターバッチ又は樹脂組成物並びに成形品を得ることができる。   As is apparent from the above description, the present invention provides an additive for resins that has a high surface hydrophilizing effect, is excellent in processability and stability, has little deterioration in mechanical properties and has no degradation during processing, and can suppress coloring. A master batch or a resin composition including the molded product can be obtained.

本発明について、さらに詳しく説明する。なお、以下、「式(1)で表される化合物」を本発明の化合物と称することもある。
本発明に係る樹脂用添加剤に含まれる本発明の化合物は式(1)により示される。
RO−(A)n−H (1)
式(1)においてRは炭素数8〜22のアルキル基を示す。アルキル基は直鎖状、または分岐鎖状であっても良いし、飽和アルキル基でも、不飽和アルキル基でも良い。本発明に用いる事のできるアルキル基としてはn−オクチル、n−ノニル、n−デシル、n−ウンデシル、n−ドデシル、n−トリデシル、n−テトラデシル、n−ペンタデシル、n−ヘキサデシル、n−ヘプタデシル、n−オクタデシル、ベヘニル、1−メチルヘプチル、1−ブチルヘキシル、イソステアリル、2−オクテニル、4−テトラデセニル、オレイルなどがある。
The present invention will be described in more detail. Hereinafter, the “compound represented by the formula (1)” may be referred to as the compound of the present invention.
The compound of the present invention contained in the resin additive according to the present invention is represented by the formula (1).
RO- (A) n-H (1)
In the formula (1), R represents an alkyl group having 8 to 22 carbon atoms. The alkyl group may be linear or branched, and may be a saturated alkyl group or an unsaturated alkyl group. Examples of the alkyl group that can be used in the present invention include n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, and n-heptadecyl. N-octadecyl, behenyl, 1-methylheptyl, 1-butylhexyl, isostearyl, 2-octenyl, 4-tetradecenyl, oleyl and the like.

式(1)においてnは平均の重合度であり、式(1)で表される化合物の製法にもよるが、nは一般に単分散ではなく、分布がある数値である。nは水酸基価に基づいて、下記式(2)により計算できる。   In the formula (1), n is an average degree of polymerization, and although it depends on the production method of the compound represented by the formula (1), n is generally not monodispersed but a value having a distribution. n can be calculated by the following formula (2) based on the hydroxyl value.

Figure 2010001384
Figure 2010001384

式(2)中、MWalはアルキルアルコールの平均分子量を表す。   In formula (2), MWal represents the average molecular weight of the alkyl alcohol.

式(1)においてアルキル基の炭素数とnの値は、本発明の化合物の対象樹脂や求められる性能により決定される。本発明の化合物は対象樹脂種の極性に応じた親水性、疎水性を持つ必要があるがアルキル基の炭素数が増すと疎水性が増し、炭素数が減ると親水性が増す。
そして、nの値が増すと、親水性が増し、nの値が減ると、疎水性が増す。また、アルキル基の炭素数とnの値の和により決定される分子量も重要であり、分子量が小さい場合、初期の表面親水性が良好になるが経時での持続性が悪くなる。また、本発明の化合物が揮発しやすくなるデメリットもある。分子量が大きい場合、初期の表面親水性の発現性が悪くなるが、持続性が向上し、樹脂の物性低下などの影響も小さくなる。アルキル基の炭素数とnの値はこれらの傾向からバランス良く選ぶ必要があるが、アルキル基としては炭素数が8から22の範囲にあることが好ましく、オクチル基やラウリル基、ミリスチル基、ステアリル基が好ましい。アルキル基の炭素数は単一であっても良いし、複数の混合物であっても良い。
nの値はその数平均において1から20であり、好ましくは2〜20であり、さらに好ましくは4〜10である。
In formula (1), the number of carbon atoms of the alkyl group and the value of n are determined by the target resin of the compound of the present invention and the required performance. The compound of the present invention needs to have hydrophilicity and hydrophobicity according to the polarity of the target resin species, but the hydrophobicity increases as the carbon number of the alkyl group increases, and the hydrophilicity increases as the carbon number decreases.
And when the value of n increases, hydrophilicity increases, and when the value of n decreases, hydrophobicity increases. Further, the molecular weight determined by the sum of the carbon number of the alkyl group and the value of n is also important. When the molecular weight is small, the initial surface hydrophilicity is improved, but the sustainability with time is deteriorated. In addition, there is a demerit that the compound of the present invention easily volatilizes. When the molecular weight is large, the initial surface hydrophilicity is deteriorated, but the sustainability is improved, and the influence of a decrease in physical properties of the resin is reduced. The carbon number of the alkyl group and the value of n need to be selected in a balanced manner from these tendencies, but the alkyl group preferably has a carbon number in the range of 8 to 22, and octyl group, lauryl group, myristyl group, stearyl. Groups are preferred. The alkyl group may have a single carbon number or a mixture of a plurality of carbon atoms.
The value of n is 1 to 20 in the number average, preferably 2 to 20, and more preferably 4 to 10.

式(1)で表される化合物は公知の方法で得られる。例えば、アルキルアルコールと、該アルキルアルコールに対し3〜5倍当量のグリシドールとをアルカリ触媒下、50〜100℃で反応させ、減圧下、130〜200℃で未反応のアルキルアルコール及び遊離ポリグリセロールを留去する方法で得られる。   The compound represented by formula (1) can be obtained by a known method. For example, an alkyl alcohol and 3 to 5 equivalents of glycidol with respect to the alkyl alcohol are reacted at 50 to 100 ° C. under an alkali catalyst, and unreacted alkyl alcohol and free polyglycerol are reacted at 130 to 200 ° C. under reduced pressure. Obtained by distilling off.

本発明に係る樹脂用添加剤は式(1)で表される化合物の他に、樹脂や用途に適した表面親水化性能を発揮する目的等でその他の界面活性剤を包含する樹脂用添加剤を含有することができる。界面活性剤としては、アニオン系、カチオン系、ノニオン系、両性系界面活性剤が挙げられるが、これらの内、特にアニオン系界面活性剤との併用が好ましい。このアニオン系界面活性剤は、式(1)で表される化合物に対して1〜50質量%の範囲で用いることが好ましい。本発明に係る樹脂用添加剤は、本発明の化合物及び上記界面活性剤の他に、公知の樹脂用添加剤を含有していても良い。   In addition to the compound represented by the formula (1), the resin additive according to the present invention includes other surfactants for the purpose of exhibiting surface hydrophilization performance suitable for the resin and application. Can be contained. Examples of the surfactant include an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant. Of these, the combined use with an anionic surfactant is particularly preferable. This anionic surfactant is preferably used in the range of 1 to 50% by mass with respect to the compound represented by the formula (1). The resin additive according to the present invention may contain a known resin additive in addition to the compound of the present invention and the surfactant.

〔アニオン系界面活性剤〕
アニオン系界面活性剤としてはアルキル硫酸エステル、ポリオキシエチレンアルキル硫酸エステル、α−スルホ脂肪酸エステル、α−オレフィンスルホン酸、アルキルスルホン酸、アルキルベンゼンスルホン酸、アルキル又はヒドロキシアルキルエーテルカルボン酸、N−アシルタウリン、N−アシルメチルタウリン、N−アシルグリシン、N−アシルアスパラギン酸、N−アシルザルコシン、N−アシルグルタミン酸、モノアルキルリン酸エステル、アルキルアミドエーテル硫酸エステル、脂肪酸モノグリセライド硫酸エステル、脂肪酸ポリグリセリン硫酸エステル、アルキルイミノジカルボン酸、ジアルキルスルホコハク酸、アルキルグリセリルエーテル硫酸エステル、アルキルポリグリセリルエーテル硫酸エステル、二級アミド型N−アシルアミノ酸塩、酒石酸アルキルアミド、リンゴ酸アルキルアミド、クエン酸アルキルアミド及びこれらの塩などが挙げられる。
[Anionic surfactant]
Anionic surfactants include alkyl sulfates, polyoxyethylene alkyl sulfates, α-sulfo fatty acid esters, α-olefin sulfonic acids, alkyl sulfonic acids, alkyl benzene sulfonic acids, alkyl or hydroxyalkyl ether carboxylic acids, N-acyl taurines. N-acylmethyl taurine, N-acyl glycine, N-acyl aspartic acid, N-acyl sarcosine, N-acyl glutamic acid, monoalkyl phosphate ester, alkylamide ether sulfate ester, fatty acid monoglyceride sulfate ester, fatty acid polyglycerol sulfate ester, Alkyliminodicarboxylic acid, dialkylsulfosuccinic acid, alkyl glyceryl ether sulfate, alkyl polyglyceryl ether sulfate, secondary amide type N-a Examples include silamino acid salts, tartaric acid alkylamides, malic acid alkylamides, citric acid alkylamides, and salts thereof.

〔カチオン系界面活性剤〕
カチオン系界面活性剤としては、アルキル四級アンモニウム塩、エーテル基又はエステル基を有するアルキル四級アンモニウム塩、テトラアルキルホスホニウム塩あるいはそれらの塩酸塩、硫酸塩、硝酸塩、有機酸塩などが挙げられる。
[Cationic surfactant]
Examples of the cationic surfactant include alkyl quaternary ammonium salts, alkyl quaternary ammonium salts having an ether group or an ester group, tetraalkylphosphonium salts or their hydrochlorides, sulfates, nitrates, and organic acid salts.

〔ノニオン系界面活性剤〕
ノニオン系界面活性剤としては、本発明以外のアルキル多価アルコールエーテル、ヒドロキシアルキル多価アルコールエーテル、高級アルコールエトキシレート、高級アルコールエトキシプロポキシレート、ノニルフェノールエトキシレート、ポリオキシエチレンアルキルアミン、脂肪酸アルカノールアミド、ショ糖脂肪酸エステル、アルキル(ポリ)グリコシド、ソルビタン脂肪酸エステル、グリセロール脂肪酸エステル、ポリグリセロール脂肪酸エステル、これらの脂肪酸エステルのエトキシレート、脂肪酸2,3−ジヒドロキシプロピルアミド、脂肪酸ポリオキシエチレンアミド、アルキルアミンオキシド、アルキルアミドアミンオキシド、ポリオキシエチレン脂肪酸エステル、メチルあるいはエチルグリコシド、脂肪酸エステル、脂肪酸、高級アルコール、ポリオキシエチレン、ポリオキシエチレンポリオキシプロピレンブロック共重合体、アシルグルカミドなどが挙げられる。
[Nonionic surfactant]
Nonionic surfactants include alkyl polyhydric alcohol ethers other than the present invention, hydroxyalkyl polyhydric alcohol ethers, higher alcohol ethoxylates, higher alcohol ethoxypropoxylates, nonylphenol ethoxylates, polyoxyethylene alkylamines, fatty acid alkanolamides, Sucrose fatty acid ester, alkyl (poly) glycoside, sorbitan fatty acid ester, glycerol fatty acid ester, polyglycerol fatty acid ester, ethoxylate of these fatty acid esters, fatty acid 2,3-dihydroxypropylamide, fatty acid polyoxyethyleneamide, alkylamine oxide , Alkylamidoamine oxide, polyoxyethylene fatty acid ester, methyl or ethyl glycoside, fatty acid ester, fat Acid, higher alcohol, polyoxyethylene, polyoxyethylene polyoxypropylene block copolymers, and the like Ashirugurukamido.

〔両性系界面活性剤〕
両性系界面活性剤としては、トリアルキルカルボキシメチルベタイン、スルホベタイン、アミドプロピルベタイン、イミダゾリウムベタイン、カルボキシベタイン、ホスホベタインなどが挙げられる。
[Amphoteric surfactant]
Examples of amphoteric surfactants include trialkylcarboxymethyl betaine, sulfobetaine, amidopropyl betaine, imidazolium betaine, carboxybetaine, and phosphobetaine.

本発明に係る樹脂用添加剤は式(1)で表される化合物とその他の樹脂用添加剤を目的に応じて、式(1)で表される化合物が20質量%以上、より好ましくは主成分(質量比で50%を超える量。)である範囲内で、任意の比率を以って混合して用いて良い。併用する樹脂用添加剤は1種類であっても良いし、数種類の混合物であっても良い。この併用する事ができる樹脂用添加剤には可塑剤、安定剤、滑剤、加工性改良剤、酸化防止剤、加水分解防止剤、スリップ剤、顔料、フィラー、難燃剤などが挙げられる。複数の樹脂用添加剤を混合して用いる場合はあらかじめ複数の樹脂用添加剤を混合しておいて、樹脂に添加しても良いし、樹脂の成形加工中に複数の樹脂用添加剤を別々に添加して混合しても良い。 According to the purpose of the resin additive according to the present invention, the compound represented by the formula (1) and other resin additives, the compound represented by the formula (1) is 20% by mass or more, more preferably It may be used by mixing at an arbitrary ratio within the range of components (amount exceeding 50% by mass). The resin additive used in combination may be one type or a mixture of several types. Examples of the resin additives that can be used in combination include plasticizers, stabilizers, lubricants, processability improvers, antioxidants, hydrolysis inhibitors, slip agents, pigments, fillers, flame retardants, and the like. When a plurality of resin additives are used in combination, a plurality of resin additives may be mixed in advance and added to the resin, or a plurality of resin additives may be separately added during resin molding. It may be added to and mixed.

本発明に係る樹脂用添加剤は樹脂に添加してその効果を発揮する。本発明に係る樹脂用添加剤を適用できる樹脂(対象樹脂)としては特に限定なく任意の樹脂を用いることができる。対象樹脂としては例えば、ポリエチレン、ポリプロピレン、ポリスチレン、AS樹脂、ABS樹脂、ポリメチルメタクリレート、ポリ酢酸ビニル、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリビニルアルコール、ポリカーボネート、ポリアミド、ポリアセタール、変性ポリフェニレンエーテル、ポリフェニレンスルフィド、酢酸セルロース、ポリエチレンテレフタレート、ポリブチレンテレフタレート、脂肪族ポリエステルなどの熱可塑性樹脂やフェノール樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、ジアリルフタレート樹脂、エポキシ樹脂、珪素樹脂、ポリウレタン、ポリイミドなどの熱硬化性樹脂がある。また、ポリオレフィン系、ポリ塩化ビニル系、ポリウレタン系、ポリエステル系、ポリアミド系などの熱可塑性エラストマーや天然ゴム、スチレンブタジエンゴム、アクリロニトリル・ブタジエンゴム、エチレン・プロピレンゴム、クロロプレンゴム、イソプレンゴム、ブチルゴム、ブタジエンゴムなどの合成ゴムも用いる事ができる。これらの中、ポリエチレン、ポリプロピレン、エチレン酢酸ビニル共重合体、塩化ビニル、ポリ乳酸から選ばれる少なくとも1つが好ましい対象樹脂である。   The additive for resin according to the present invention is added to the resin and exhibits its effect. As resin (target resin) to which the additive for resin according to the present invention can be applied, any resin can be used without any particular limitation. Examples of the target resin include polyethylene, polypropylene, polystyrene, AS resin, ABS resin, polymethyl methacrylate, polyvinyl acetate, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polycarbonate, polyamide, polyacetal, modified polyphenylene ether, polyphenylene sulfide, Thermosetting of thermoplastic resin such as cellulose acetate, polyethylene terephthalate, polybutylene terephthalate, aliphatic polyester, phenol resin, urea resin, melamine resin, unsaturated polyester resin, diallyl phthalate resin, epoxy resin, silicon resin, polyurethane, polyimide, etc. There is a functional resin. Also, thermoplastic elastomers such as polyolefin, polyvinyl chloride, polyurethane, polyester and polyamide, natural rubber, styrene butadiene rubber, acrylonitrile butadiene rubber, ethylene propylene rubber, chloroprene rubber, isoprene rubber, butyl rubber, butadiene Synthetic rubber such as rubber can also be used. Among these, at least one selected from polyethylene, polypropylene, ethylene vinyl acetate copolymer, vinyl chloride, and polylactic acid is a preferable target resin.

本発明における樹脂組成物は通常のプラスチックの成型に用いられる押出機、射出成形機、カレンダー成形機、圧縮成形機、ブロー成形機などを用いて押出、射出、圧縮、ブロー等の熱成形が可能である。樹脂と樹脂用添加剤は別々に添加して、成形機中で混練しても良いし、あらかじめ、混合しておいても良い。ポリマーブレンドを行う場合には二軸押出機の方が好ましい。しかし、加工機の種類によっては、樹脂用添加剤の添加量が高い場合、樹脂の喰い込みが悪く加工できなかったり、加工できても充分混錬できず分散不良が生じたりする場合がある。このため、あらかじめ樹脂に対し樹脂用添加剤を高濃度に含有させたマスターバッチを二軸押出機やバンバリーミキサーにより作製し、これを所定の樹脂用添加剤濃度になるように樹脂と混合して成形することが好ましい。この場合マスターバッチの樹脂用添加剤の濃度はマスターバッチ中の式(1)で表される化合物の量が、5質量%以上20質量%以下となる量が好ましい。
本発明に係るマスターバッチの作製については、従来公知の技術を特別の制限なく採用できる。
The resin composition in the present invention can be subjected to thermoforming such as extrusion, injection, compression, and blow using an extruder, an injection molding machine, a calendar molding machine, a compression molding machine, a blow molding machine, etc. that are used for molding ordinary plastics. It is. The resin and the resin additive may be added separately and kneaded in a molding machine, or may be mixed in advance. In the case of polymer blending, a twin screw extruder is preferred. However, depending on the type of processing machine, when the additive amount of the resin additive is high, the resin bite may be poor and cannot be processed, or even if processed, it may not be kneaded sufficiently, resulting in poor dispersion. For this reason, a master batch containing a resin additive in a high concentration with respect to the resin in advance is prepared by a twin screw extruder or a Banbury mixer, and this is mixed with the resin so as to have a predetermined resin additive concentration. It is preferable to mold. In this case, the concentration of the resin additive in the master batch is preferably such that the amount of the compound represented by the formula (1) in the master batch is 5% by mass or more and 20% by mass or less.
For the production of the master batch according to the present invention, a conventionally known technique can be employed without any particular limitation.

また、本発明に係る樹脂用添加剤をフィラーとともに用い、主としてフィラーの分散性向上で用いる場合には、あらかじめフィラーに樹脂用添加剤を吸着させてから、樹脂と混練して用いる事が好ましい。例えば、リボンブレンダーを用いフィラーを撹拌しながら、融点以上に熱して融解した樹脂用添加剤をスプレーして振りかけることにより、フィラーに対し、樹脂用添加剤を吸着させる事ができる。この場合、フィラーに対する本発明に係る樹脂用添加剤の使用量は質量比で1%〜100%が好ましい。   Further, when the resin additive according to the present invention is used together with a filler and mainly used for improving the dispersibility of the filler, it is preferable that the resin additive is adsorbed on the filler in advance and then kneaded with the resin. For example, the resin additive can be adsorbed to the filler by spraying and sprinkling the melted resin additive while stirring the filler using a ribbon blender. In this case, the use amount of the resin additive according to the present invention relative to the filler is preferably 1% to 100% by mass ratio.

用いることができるフィラーとしては、例えば、炭酸カルシウム、炭酸マグネシウム、シリカ、ケイ酸カルシウム、カーボンブラック、カーボン繊維、ガラス繊維、金属繊維、酸化チタン、クレー、マイカ、タルク 、水酸化マグネシウム、水酸化アルミニウム、酸化亜鉛、各種有機繊維、木粉、クルミ殻粉、ジュート、ケナフ、セルロース、リグニンなどが挙げられる。   Examples of the filler that can be used include calcium carbonate, magnesium carbonate, silica, calcium silicate, carbon black, carbon fiber, glass fiber, metal fiber, titanium oxide, clay, mica, talc, magnesium hydroxide, and aluminum hydroxide. Zinc oxide, various organic fibers, wood flour, walnut shell flour, jute, kenaf, cellulose, lignin and the like.

本発明の樹脂組成物において、樹脂用添加剤の樹脂に対する添加量は、樹脂組成物中の式(1)で表される化合物量が0.1〜20質量%となる量が好ましく、特に0.1〜5質量%となる量が好ましい。樹脂用添加剤の添加量がかかる範囲より少ない場合は充分な表面親水化効果や分散性向上効果が得られないし、かかる範囲より多い場合には、樹脂の透明性や機械物性が低下したり、樹脂からブリードアウトしたりする。   In the resin composition of the present invention, the amount of the resin additive added to the resin is preferably such that the amount of the compound represented by the formula (1) in the resin composition is 0.1 to 20% by mass, particularly 0. An amount of 1 to 5% by mass is preferable. When the amount of the additive for the resin is less than the range, sufficient surface hydrophilizing effect and dispersibility improvement effect cannot be obtained, and when it is more than the range, the transparency and mechanical properties of the resin are lowered, Bleed out from the resin.

本発明の樹脂組成物はTダイ、インフレーション、カレンダーなどによりシート或いはフィルムへ成形することができる。フィルムについては延伸、無延伸のいずれのものでも構わない。また、射出成形機、圧縮成形機などを用いて成形品を得ることもできる。例えば、ブロー成形によりボトルなどを成形する事ができる。   The resin composition of the present invention can be formed into a sheet or film by T-die, inflation, calender and the like. The film may be either stretched or unstretched. In addition, a molded product can be obtained using an injection molding machine, a compression molding machine or the like. For example, a bottle or the like can be formed by blow molding.

以下に実施例を挙げて本発明を詳細に説明するが、本発明の態様はこれに限定されない。   Hereinafter, the present invention will be described in detail with reference to examples, but the embodiment of the present invention is not limited thereto.

製造例1 [ポリグリセロールモノラウリルエーテル]
ラウリルアルコール175g(0.9392mol)とグリシドール200g(2.700mol)に水酸化ナトリウム5.746g(0.144mol)を触媒に用いた。反応はラウリルアルコールと水酸化ナトリウムを反応させ、アルコキシドとした後、トルエン200mlを加えて、反応温度90℃にてグリシドールを約0.8ml/minの速度で滴下した。滴下終了後さらに6時間90℃にて熟成させた。反応は、不活性ガス雰囲気下で行った。反応終了後、触媒は当量のリン酸で中和、中和塩と分離したポリグリセロールを濾別し、トルエンを留去して粗ポリグリセロールモノラウリルエーテル370gを得た。さらに未反応のラウリルアルコールを減圧蒸留で留去し(0.92kPa、150〜180℃、対仕込み14.5%カット)、ポリグリセロールモノラウリルエーテル[化合物(1)]を314g得た。この化合物(1)の水酸基価は589.2mgKOH/ml、水酸基価から求めた平均重合度は4.3であった。
Production Example 1 [polyglycerol monolauryl ether]
Sodium hydroxide (5.746 g, 0.144 mol) was used as a catalyst for 175 g (0.9392 mol) of lauryl alcohol and 200 g (2.700 mol) of glycidol. In the reaction, lauryl alcohol and sodium hydroxide were reacted to form an alkoxide, 200 ml of toluene was added, and glycidol was added dropwise at a reaction temperature of 90 ° C. at a rate of about 0.8 ml / min. After completion of dropping, the mixture was further aged at 90 ° C. for 6 hours. The reaction was carried out under an inert gas atmosphere. After completion of the reaction, the catalyst was neutralized with an equivalent amount of phosphoric acid, the polyglycerol separated from the neutralized salt was filtered off, and toluene was distilled off to obtain 370 g of crude polyglycerol monolauryl ether. Further, unreacted lauryl alcohol was distilled off by distillation under reduced pressure (0.92 kPa, 150 to 180 ° C., 14.5% cut in charge) to obtain 314 g of polyglycerol monolauryl ether [compound (1)]. The hydroxyl value of this compound (1) was 589.2 mgKOH / ml, and the average degree of polymerization determined from the hydroxyl value was 4.3.

製造例2 [グリセロールモノラウリルエーテル]
上記で製造した化合物(1)5000gを分子蒸留機(アルバック社製、CEH−300II)を用い、0.4Pa下、100℃、110℃、120℃で3回蒸留した。120℃の蒸留操作でグリセロールモノラウリルエーテル[化合物(2)]を267gを得た。この化合物(2)の水酸基価は431.3、水酸基価から求めた平均重合度は1.0であった。
Production Example 2 [Glycerol monolauryl ether]
5000 g of the compound (1) produced above was distilled three times at 0.4 ° C., 100 ° C., 110 ° C., and 120 ° C. using a molecular distillation machine (manufactured by ULVAC, CEH-300II). By distillation at 120 ° C., 267 g of glycerol monolauryl ether [compound (2)] was obtained. The hydroxyl value of this compound (2) was 431.3, and the average degree of polymerization determined from the hydroxyl value was 1.0.

製造例3 [ポリグリセロールモノイソステアリルエーテル]
イソステアリルアルコール250g(0.925mol)とグリシドール200g(2.700mol)に水酸化ナトリウム5.71g(0.143mol)を触媒に用いた。反応はイソステアリルアルコールと水酸化ナトリウムを反応させ、アルコキシドとした後、トルエン200mlを加えて、反応温度90℃にてグリシドールを約0.8ml/minの速度で滴下した。滴下終了後さらに6時間90℃にて熟成させた。反応は、不活性ガス雰囲気下で行った。反応終了後、触媒は当量のリン酸で中和、中和塩と分離したポリグリセロールを濾別し、トルエンを留去して粗ポリグリセロールモノイソステアリルエーテル436gを得た。さらに未反応のイソステアリルアルコールを減圧蒸留で留去し(0.9kPa、160〜200℃、対仕込み13.8%カット)、ポリグリセロールモノイソステアリルエーテル[化合物(3)]を376g得た。この化合物(3)の水酸基価は511.2mgKOH/ml、水酸基価から求めた平均重合度は4.5であった。
Production Example 3 [polyglycerol monoisostearyl ether]
Sodium hydroxide (5.71 g, 0.143 mol) was used as a catalyst for isostearyl alcohol (250 g, 0.925 mol) and glycidol (200 g, 2.700 mol). In the reaction, isostearyl alcohol and sodium hydroxide were reacted to form an alkoxide, 200 ml of toluene was added, and glycidol was added dropwise at a reaction temperature of 90 ° C. at a rate of about 0.8 ml / min. After completion of dropping, the mixture was further aged at 90 ° C. for 6 hours. The reaction was carried out under an inert gas atmosphere. After completion of the reaction, the catalyst was neutralized with an equivalent amount of phosphoric acid, and the polyglycerol separated from the neutralized salt was filtered off, and toluene was distilled off to obtain 436 g of crude polyglycerol monoisostearyl ether. Further, unreacted isostearyl alcohol was distilled off under reduced pressure (0.9 kPa, 160 to 200 ° C., charged to 13.8% cut) to obtain 376 g of polyglycerol monoisostearyl ether [compound (3)]. The hydroxyl value of this compound (3) was 511.2 mgKOH / ml, and the average degree of polymerization determined from the hydroxyl value was 4.5.

製造例4 [ポリグリセロールモノヘキサデシルエーテル]
ヘキサデシルアルコール250g(1.032mol)とグリシドール200g(2.700mol)に水酸化ナトリウム5.99g(0.150mol)を触媒に用いた。反応はヘキサデシルアルコールと水酸化ナトリウムを反応させ、アルコキシドとした後、トルエン200mlを加えて、反応温度90℃にてグリシドールを約0.8ml/minの速度で滴下した。滴下終了後さらに6時間90℃にて熟成させた。反応は、不活性ガス雰囲気下で行った。反応終了後、触媒は当量のリン酸で中和、中和塩と分離したポリグリセロールを濾別し、トルエンを留去して粗ポリグリセロールモノヘキサデシルエーテル432gを得た。さらに未反応のヘキサデシルアルコールを減圧蒸留で留去し(0.9kPa、160〜200℃、対仕込み15.2%カット)、ポリグリセロールモノヘキサデシルエーテル[化合物(4)]を366g得た。この化合物(4)の水酸基価は499.6mgKOH/ml、水酸基価から求めた平均重合度は3.4であった。
Production Example 4 [polyglycerol monohexadecyl ether]
Sodium hydroxide 5.99 g (0.150 mol) was used as a catalyst for 250 g (1.032 mol) of hexadecyl alcohol and 200 g (2.700 mol) of glycidol. In the reaction, hexadecyl alcohol and sodium hydroxide were reacted to form an alkoxide, 200 ml of toluene was added, and glycidol was added dropwise at a reaction temperature of 90 ° C. at a rate of about 0.8 ml / min. After completion of dropping, the mixture was further aged at 90 ° C. for 6 hours. The reaction was carried out under an inert gas atmosphere. After completion of the reaction, the catalyst was neutralized with an equivalent amount of phosphoric acid, and the polyglycerol separated from the neutralized salt was filtered off, and toluene was distilled off to obtain 432 g of crude polyglycerol monohexadecyl ether. Further, unreacted hexadecyl alcohol was distilled off by distillation under reduced pressure (0.9 kPa, 160 to 200 ° C., charge 15.2% cut) to obtain 366 g of polyglycerol monohexadecyl ether [compound (4)]. The hydroxyl value of this compound (4) was 499.6 mgKOH / ml, and the average degree of polymerization determined from the hydroxyl value was 3.4.

樹脂(1):ポリエチレン(ノバテックLD LF440HB:日本ポリエチレン社製)
樹脂(2):ポリプロピレン(ノバテックPP BC03C:日本ポリプロ社製)
樹脂(3):ポリ乳酸(レイシアH−100:三井化学社製)
樹脂(4):ポリ塩化ビニル(TH700:大洋塩ビ社製)
樹脂(5):ポリエチレン酢酸ビニル共重合体(NUC3758:日本ユニカー社製)
Resin (1): Polyethylene (Novatech LD LF440HB: manufactured by Nippon Polyethylene)
Resin (2): Polypropylene (Novatech PP BC03C: manufactured by Nippon Polypro Co., Ltd.)
Resin (3): Polylactic acid (Lacia H-100, manufactured by Mitsui Chemicals)
Resin (4): Polyvinyl chloride (TH700: manufactured by Taiyo PVC Co.)
Resin (5): Polyethylene vinyl acetate copolymer (NUC3758: manufactured by Nihon Unicar)

試験方法は以下による。
[試験−1]帯電防止性
試験片は100×100mm、厚さ2mmのものを使用した。室温20℃、湿度65%RHで1週間エージングした試験片を、同条件で極超絶縁計SEM−10型(東亜電波工業社製)により表面固有抵抗を測定した。印加電圧は500Vで1分後の値を読み取った。樹脂の表面固有抵抗は通常1016Ω以上であるが、樹脂用添加剤を加えると10〜1014Ω程度に低下する。抵抗値が低いほど帯電防止性が良くなる。
The test method is as follows.
[Test-1] Antistatic property A test piece having a size of 100 × 100 mm and a thickness of 2 mm was used. The surface resistivity of a test piece aged at room temperature of 20 ° C. and humidity of 65% RH for 1 week was measured with a super insulation meter SEM-10 (manufactured by Toa Denpa Kogyo Co., Ltd.) under the same conditions. The applied voltage was 500 V and the value after 1 minute was read. The surface specific resistance of the resin is usually 10 16 Ω or more, but when the resin additive is added, it decreases to about 10 9 to 10 14 Ω. The lower the resistance value, the better the antistatic property.

[試験−2]防曇性
試験フィルムは100×100mm、厚さ50μmのものを使用した。試験フィルムは成形後、室温20℃、湿度65%RHで1週間エージングして試験に供した。300mlビーカーに200mlの常温の蒸留水を入れ、試験フィルムをかぶせ、密着させた。水を入れフィルムで覆ったビーカーを5℃の冷蔵庫中に入れ、フィルムに付着する水滴を観察した。冷蔵庫に入れて1時間後のフィルムが曇っている場合を×、曇ってなくビーカーの中身がはっきり見える場合を○とした。
[Test-2] Antifogging test film having a size of 100 × 100 mm and a thickness of 50 μm was used. A test film was aged at room temperature of 20 ° C. and a humidity of 65% RH for 1 week after molding, and was subjected to the test. 200 ml of room temperature distilled water was put into a 300 ml beaker, and a test film was placed on the beaker so as to adhere. A beaker filled with water and covered with a film was placed in a refrigerator at 5 ° C., and water droplets adhering to the film were observed. The case where the film after 1 hour was put in the refrigerator was cloudy was rated as x, and the case where the content of the beaker was clearly visible without being clouded was marked as ◯.

[試験−3]ビカット軟化点測定試験
試験片は25×20mm、厚さ2mmのものを使用した。東洋精機社製HDT TESTER により、ビカット軟化点(JIS K7206)を測定した。負荷は50N、昇温速度は50℃/hである。
[Test-3] Vicat softening point measurement test A test piece of 25 × 20 mm and a thickness of 2 mm was used. The Vicat softening point (JIS K7206) was measured by HDT TESTER manufactured by Toyo Seiki Co., Ltd. The load is 50 N, and the heating rate is 50 ° C./h.

実施例1〜10、比較例1〜3
樹脂(1)〜(3)の帯電防止性の比較
表1に示す配合で樹脂、本発明の化合物を混合し、ラボプラストミル(東洋精機社製)にて180℃15min溶融混練し、小型プレス機にて180℃でプレスし2mm厚の板状に成形した。試験片を100×100mmに切り出し、試験−1に供した。結果を表1に示した。
Examples 1-10, Comparative Examples 1-3
Comparison of antistatic properties of resins (1) to (3) Resin and the compound of the present invention were mixed in the formulation shown in Table 1, and melt-kneaded at 180 ° C. for 15 minutes in a laboratory plast mill (manufactured by Toyo Seiki Co., Ltd.). It was pressed at 180 ° C. with a machine and formed into a 2 mm thick plate. A test piece was cut out to 100 × 100 mm and subjected to Test-1. The results are shown in Table 1.

Figure 2010001384
Figure 2010001384

実施例11、比較例4
樹脂(4)の帯電防止性の比較
表2に示す配合でヘンシェルミキサーにて120℃5min混合した。続いて、ラボプラストミル(東洋精機社製)にて170℃10min溶融混練し、小型プレス機にて170℃でプレスし2mm厚の板状に成形した。試験片を100×100mmに切り出し、試験−1に供した。結果を表2に示した。
Example 11, Comparative Example 4
Comparison of antistatic property of resin (4) The mixture shown in Table 2 was mixed at 120 ° C. for 5 minutes with a Henschel mixer. Subsequently, the mixture was melt-kneaded at 170 ° C. for 10 minutes with a Laboplast mill (manufactured by Toyo Seiki Co., Ltd.) and pressed at 170 ° C. with a small press to form a 2 mm thick plate. A test piece was cut out to 100 × 100 mm and subjected to Test-1. The results are shown in Table 2.

Figure 2010001384
Figure 2010001384

注1:エポキシ化大豆油;ダイセル化学社製 エポキシ化大豆油
注2:錫系安定剤;日東化成社製 #8831
Note 1: Epoxidized soybean oil; Daicel Chemical Industries Epoxidized soybean oil Note 2: Tin-based stabilizer; Nitto Kasei Co., Ltd. # 8831

実施例12、比較例5
樹脂(5)の防曇性の比較
樹脂(5)90質量%に対し化合物(1)が10質量%になるように流量を調整し、ストランドダイを備えた小型異方向二軸押出機により190℃にて溶融混練し、ストランドを水冷して切断し、マスターバッチペレットを作製した。作製したマスターバッチペレットを80℃、12時間乾燥させた。続いて、表3に示す配合で混合しインフレーション成形機にて180℃で厚さ50μmのフィルムに成形した。成形したフィルムを試験−2に供した。結果を表3に示す。
Example 12, Comparative Example 5
Comparison of anti-fogging property of resin (5) The flow rate was adjusted so that the compound (1) was 10% by mass with respect to 90% by mass of the resin (5), and the resin was rotated 190 by a small-sized bi-directional extruder equipped with a strand die. The strand was melt-kneaded at 0 ° C., the strand was cooled with water and cut to prepare a master batch pellet. The produced master batch pellet was dried at 80 ° C. for 12 hours. Then, it mixed by the mixing | blending shown in Table 3, and shape | molded in the 50-micrometer-thick film at 180 degreeC with the inflation molding machine. The formed film was subjected to Test-2. The results are shown in Table 3.

Figure 2010001384
Figure 2010001384

実施例13−15、比較例6、7
アニオン系界面活性剤との併用での帯電防止性の比較
表4に示す配合で混合し、ストランドダイを備えた小型異方向二軸押出機により190℃にて溶融混練し、ストランドを水冷して切断し、ペレットを作成した。作成したペレットを100℃、5時間乾燥させた。続いて、ペレットを射出成形機にて190℃で10×10×2mmの板状に成形し、試験−1に供した。結果を表4に示した。尚、注3に示すアニオン系界面活性剤に限らず、前記〔アニオン系界面活性剤〕の例示化合物の全てについて同様の効果がみられた。
Examples 13-15, Comparative Examples 6, 7
Comparison of antistatic properties when used in combination with an anionic surfactant Mixtures shown in Table 4 were mixed, melt-kneaded at 190 ° C by a small-sized bi-directional extruder equipped with a strand die, and the strands were cooled with water. Cutting and making pellets. The prepared pellets were dried at 100 ° C. for 5 hours. Subsequently, the pellets were molded into a plate shape of 10 × 10 × 2 mm at 190 ° C. with an injection molding machine and subjected to Test-1. The results are shown in Table 4. In addition, the same effect was seen not only about the anionic surfactant shown in Note 3, but about all the exemplary compounds of said [anionic surfactant].

Figure 2010001384
Figure 2010001384

注3:アニオン系界面活性剤:松本油脂社製 TB−160(アルキルスルホン酸ナトリウム)   Note 3: Anionic surfactant: Matsumoto Yushi Co., Ltd. TB-160 (sodium alkyl sulfonate)

実施例16−18、比較例8
フィラーの分散性の比較
タルク(ハイトロンA、竹原化学社製)100gに対し、表5に示す本発明の化合物100gを加え、ヘンシェルミキサーにて100℃ 10min撹拌し吸着させた。樹脂、本発明の化合物、タルクの比率が表5に記載の濃度になるように本発明の化合物を吸着したタルクと樹脂を混合し、ストランドダイを備えた小型異方向二軸押出機により190℃にて溶融混練し、ストランドを水冷して切断し、ペレットを作成した。作成したペレットを100℃、5時間乾燥させた。続いて、ペレットを射出成形機にて190℃で金型温度105℃、冷却時間60秒にて、厚さ2mmの試験片に成形し、適宜切り出し試験−3に供した。結果を表5に示した。
Examples 16-18, Comparative Example 8
Comparison of Dispersibility of Filler 100 g of the compound of the present invention shown in Table 5 was added to 100 g of talc (Hytron A, manufactured by Takehara Chemical Co., Ltd.), and the mixture was adsorbed by stirring at 100 ° C. for 10 minutes with a Henschel mixer. The resin, the compound of the present invention, and the talc adsorbed with the compound of the present invention are mixed so that the ratio of talc is as shown in Table 5 and the resin is mixed. The strand was melt-kneaded and cut by water cooling to produce pellets. The prepared pellets were dried at 100 ° C. for 5 hours. Subsequently, the pellet was molded into a test piece having a thickness of 2 mm at 190 ° C., a mold temperature of 105 ° C., and a cooling time of 60 seconds using an injection molding machine. The results are shown in Table 5.

Figure 2010001384
Figure 2010001384

表5から、タルクは樹脂に添加することにより耐熱性が向上するが、タルクは樹脂中に
十分な分散性を持たないことが分かり、一方、本発明の化合物をタルクに吸着させる事により、タルクの分散性が向上し、樹脂組成物の耐熱性が向上していることが分かる。
From Table 5, it can be seen that heat resistance is improved by adding talc to the resin, but talc does not have sufficient dispersibility in the resin. On the other hand, by adsorbing the compound of the present invention to talc, It can be seen that the dispersibility of the resin composition is improved and the heat resistance of the resin composition is improved.

Claims (6)

樹脂に添加されて用いられる樹脂用添加剤において、下記式(1)で表される化合物を含有することを特徴とする樹脂用添加剤。
RO−(A)n−H (1)
(式中、Rは炭素数8〜22のアルキル基、nは平均値が1〜20、Aは−CHCHOHCHO−、−CHCH(CHOH)O−で示されるいずれかの基を表す。)
The additive for resin containing the compound represented by following formula (1) in the additive for resin used by adding to resin.
RO- (A) n-H (1)
(In the formula, R is an alkyl group having 8 to 22 carbon atoms, n is an average value of 1 to 20, and A is any one of —CH 2 CHOHCH 2 O— and —CH 2 CH (CH 2 OH) O—. Represents a group of
アニオン系界面活性剤を併せ含有することを特徴とする請求項1に記載の樹脂用添加剤。 The additive for resin according to claim 1, further comprising an anionic surfactant. 樹脂が、ポリエチレン、ポリプロピレン、エチレン酢酸ビニル共重合体、塩化ビニル、ポリ乳酸から選ばれる少なくとも1つであることを特徴とする請求項1又は2に記載の樹脂用添加剤。 The resin additive according to claim 1 or 2, wherein the resin is at least one selected from polyethylene, polypropylene, ethylene vinyl acetate copolymer, vinyl chloride, and polylactic acid. 式(1)で表される化合物を5〜20質量%含む請求項1〜3のいずれかに記載の樹脂用添加剤を含有することを特徴とするマスターバッチ。 A masterbatch comprising the resin additive according to any one of claims 1 to 3, comprising 5 to 20% by mass of the compound represented by the formula (1). 式(1)で表される化合物を0.1〜20質量%含む請求項1〜3のいずれかに記載の樹脂用添加剤を含有することを特徴とする樹脂組成物。 The resin composition containing the additive for resin in any one of Claims 1-3 containing 0.1-20 mass% of compounds represented by Formula (1). 請求項5に記載の樹脂組成物を成形してなる成形品。 A molded product obtained by molding the resin composition according to claim 5.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11273627B2 (en) 2017-01-11 2022-03-15 Bostik, Inc. Extrudable antifog copolyester heat seal resins
JP7487467B2 (en) 2019-12-02 2024-05-21 東洋製罐グループホールディングス株式会社 Propylene resin masterbatch

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4824016B1 (en) * 1969-06-23 1973-07-18
JPS564638A (en) * 1979-06-26 1981-01-19 Lion Corp Antistatic resin composition
JPH01197552A (en) * 1988-02-01 1989-08-09 Kao Corp Acrylic resin composition
JPH0649321A (en) * 1992-07-28 1994-02-22 Polyplastics Co Polyoxymethylene composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4824016B1 (en) * 1969-06-23 1973-07-18
JPS564638A (en) * 1979-06-26 1981-01-19 Lion Corp Antistatic resin composition
JPH01197552A (en) * 1988-02-01 1989-08-09 Kao Corp Acrylic resin composition
JPH0649321A (en) * 1992-07-28 1994-02-22 Polyplastics Co Polyoxymethylene composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11273627B2 (en) 2017-01-11 2022-03-15 Bostik, Inc. Extrudable antifog copolyester heat seal resins
US11806971B2 (en) 2017-01-11 2023-11-07 Bostik, Inc. Extrudable antifog copolyester heat seal resins
JP7487467B2 (en) 2019-12-02 2024-05-21 東洋製罐グループホールディングス株式会社 Propylene resin masterbatch

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