JP2004309436A - Bis-amide quantitative method - Google Patents
Bis-amide quantitative method Download PDFInfo
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- JP2004309436A JP2004309436A JP2003106806A JP2003106806A JP2004309436A JP 2004309436 A JP2004309436 A JP 2004309436A JP 2003106806 A JP2003106806 A JP 2003106806A JP 2003106806 A JP2003106806 A JP 2003106806A JP 2004309436 A JP2004309436 A JP 2004309436A
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- Prior art keywords
- bisamide
- resin
- amide
- bis
- solvent
- 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.)
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- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000004445 quantitative analysis Methods 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000011088 calibration curve Methods 0.000 claims abstract description 9
- ZJOLCKGSXLIVAA-UHFFFAOYSA-N ethene;octadecanamide Chemical group C=C.CCCCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCCCC(N)=O ZJOLCKGSXLIVAA-UHFFFAOYSA-N 0.000 claims description 13
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 11
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 8
- 239000011342 resin composition Substances 0.000 claims description 7
- 229920006122 polyamide resin Polymers 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- 229930182556 Polyacetal Natural products 0.000 claims description 3
- 239000000956 alloy Substances 0.000 claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 3
- 229920005668 polycarbonate resin Polymers 0.000 claims description 3
- 239000004431 polycarbonate resin Substances 0.000 claims description 3
- 229920001225 polyester resin Polymers 0.000 claims description 3
- 239000004645 polyester resin Substances 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 abstract description 4
- 238000004458 analytical method Methods 0.000 abstract description 3
- 238000004817 gas chromatography Methods 0.000 abstract 1
- WGOROJDSDNILMB-UHFFFAOYSA-N octatriacontanediamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(N)=O WGOROJDSDNILMB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- MXJJJAKXVVAHKI-WRBBJXAJSA-N (9z,29z)-octatriaconta-9,29-dienediamide Chemical compound NC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCCCCCC\C=C/CCCCCCCC(N)=O MXJJJAKXVVAHKI-WRBBJXAJSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WCZVSEOBNBZLEY-UHFFFAOYSA-N ethene;hexadecanamide Chemical compound C=C.CCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCC(N)=O WCZVSEOBNBZLEY-UHFFFAOYSA-N 0.000 description 1
- -1 ethylene palmitic acid stearic acid amide Chemical compound 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- FEEPBTVZSYQUDP-UHFFFAOYSA-N heptatriacontanediamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(N)=O FEEPBTVZSYQUDP-UHFFFAOYSA-N 0.000 description 1
- RKVQXYMNVZNJHZ-UHFFFAOYSA-N hexacosanediamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC(N)=O RKVQXYMNVZNJHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Landscapes
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、樹脂中に滑剤として含有されているビスアミドの定量方法に関するものである。
【０００２】
【従来の技術】
従来、樹脂中のエチレンビスステアリン酸アミドを定量する場合、熱クロロホルムなどを用いて抽出する方法がある。しかし、この方法によれば、ビスアミドを溶解するが樹脂は溶解しないため、樹脂を微粉砕し、抽出および抽出液の濃縮に長時間を要する。また、再現性についても疑問が生じる。（例えば、非特許文献１参照）
その他の方法としては、窒素量を定量しエチレンビスステアリン酸アミドに換算して試料に含まれるエチレンビスステアリン酸アミド量を算出する方法がある。しかし、樹脂の構造に窒素元素が存在する場合や窒素元素をもつ添加剤が共存している場合においてはこの方法は使えない。
【０００３】
【非特許文献１】
「高分子分析ハンドブック」（１９８５年発行、株式会社 朝倉書店）
【０００４】
【発明が解決しようとする課題】
本発明は、樹脂中に滑剤として含有されているビスアミド量を抽出／濃縮に時間を要することなく、短時間に分析できる方法を提供することを課題とする。
【０００５】
【課題を解決するための手段】
すなわち、本発明は、次のようである。
１．ビスアミドを含有する樹脂組成物中のビスアミドを定量分析する方法であって、（１）該樹脂とビスアミドを溶解する溶剤に該樹脂組成物を溶解し、該溶液をガスクロマトグラフィ／質量分析に付して該溶液中のビスアミドとビスアミド標準品の既知量とピーク面積を比較し、その後、（２）該溶液中のビスアミドが、溶剤に安定して溶解する濃度となるように再調整し、ついで、（３）ガスクロマトグラフィ／質量分析に付して分離・検出することを特徴とするビスアミドの絶対検量線法を用いる定量方法。
【０００６】
２．再調整したポリマー溶液中のビスアミドの濃度が、５００ｐｐｍ以下であることを特徴とする上記１に記載の定量方法。
３．該溶剤が、ヘキサフルオロイソプロパノールであることを特徴とする上記１または２に記載の定量方法。
４．ヘキサフルオロイソプロパノールの純度が、９９．５％以上であることを特徴とする上記１〜３のいずれかに記載の定量方法。
５．ビスアミドが、エチレンビスステアリン酸アミドである上記１〜４のいずれかに記載の定量方法。
６．該樹脂が、ポリアミド樹脂、ポリアセタール樹脂、ポリエステル樹脂、アクリル樹脂、ポリカーボネート樹脂、またこれら樹脂のアロイから選ばれる樹脂を対象とする上記１〜５のいずれかに記載の定量方法。
以下に、本発明を説明する。
【０００７】
本発明は、ビスアミドを滑剤として含有する樹脂組成物を溶解し、この該溶液をガスクロマトグラフィ／質量分析に付して溶液中のビスアミドとビスアミド標準品の既知量とピーク面積を比較し、ポリマー溶液中のビスアミドが該溶剤に安定して溶解する濃度以下になるように再調整し定量用試料とする。この定量用試料をガスクロマトグラフィ／質量分析に付して分離・検出することを特徴とするビスアミドの絶対検量線法を用いた定量方法である。
【０００８】
本発明の分析対象となるのは、ビスアミドを含有する樹脂組成物である。
本発明の溶剤は樹脂組成物、すなわち樹脂とビスアミドをともに溶解する溶剤が用いられる。ギ酸、酢酸の酸類、ヘキサフルオロイソプロパノールである。
本発明の樹脂は熱可塑性樹脂であり、ポリアミド樹脂、ポリアセタール樹脂、ポリエステル樹脂、アクリル樹脂、ポリカーボネート樹脂、またこれら樹脂のアロイである。特に、ポリアミド樹脂を用いた場合には、溶剤としてヘキサフルオロイソプロパノール（以下、ＨＦＩと略することもある）が好ましく用いられる。
【０００９】
本発明のビスアミドとしては、メチレンビスステアリン酸アミド、エチレンビスラウリン酸アミド、エチレンビスステアリン酸アミド、エチレンビスオレイン酸アミドが挙げられる。本発明は特にエチレンビスステアリン酸アミドに有効である。
また、エチレンビスステアリン酸アミドは不純物としてエチレンビスパルミチン酸アミドやエチレンパルミチン酸ステアリン酸アミドを含んでおり、以下の説明においてはこれらを総称してエチレンビスステアリン酸アミドと呼ぶ事にする。
エチレンビスステアリン酸アミドがヘキサフルオロイソプロパノールに安定して溶解する濃度は５００ｐｐｍ以下が好ましく、検量線用試料はエチレンビスステアリン酸アミド標準品をヘキサフルオロイソプロパノールに溶解させ、５００ｐｐｍ以下の濃度３点を用いる。
【００１０】
【発明の実施の形態】
以下、実施例に基いて具体的に説明する。
【００１１】
【実施例１】
エチレンビスステアリン酸アミドを１％含有させたポリアミド６を試作した。上記ペレット約５００ｍｇをヘキサフルオロイソプロパノール２０ｍｌに溶解させる。このポリマー溶液中のエチレンビスステアリン酸アミドの濃度は約２５０ｐｐｍである。
この定量用試料をガスクロマトグラフィ／質量分析「ヒューレットパッカード社製 ６８９０」／「ヒューレットパッカード社製 ５９７３」に付してエチレンビスステアリン酸アミドを定量した。検量線用試料はエチレンビスステアリン酸アミド標準品をヘキサフルオロイソプロパノールに溶解させ５００ｐｐｍ以下の濃度３点を用いた。
絶対検量線法より求めたエチレンビスステアリン酸アミド量は０．８７％であった。すなわち、本発明の方法は、簡便であって、精度も優れていることがわかる。
【００１２】
【実施例２】
エチレンビスステアリン酸アミドを１％含有するポリアミド６を試料とした。
上記ペレット約１００ｍｇをＨＦＩＰ２０ｍｌに溶解させる。このポリマー溶液中のエチレンビスステアリン酸アミドの濃度は約５０ｐｐｍである。
この定量用試料をガスクロマトグラフィ／質量分析「ヒューレットパッカード社製 ６８９０」／「ヒューレットパッカード社製 ５９７３」に付してエチレンビスステアリン酸アミドを定量した。検量線用試料はエチレンビスステアリン酸アミド標品をヘキサフルオロイソプロパノールに溶解させ５００ｐｐｍ以下の濃度３点を用いた。
絶対検量線法より求めたエチレンビスステアリン酸アミド量は０．８５％であった。
【００１３】
【比較例１】
エチレンビスステアリン酸アミドを約１％含有するポリアミド６を試料とした。具体的にはペレット約２０００ｍｇをＨＦＩＰ２０ｍｌに溶解させたところ、完全に溶解しなかったので定量分析を中止した。
【００１４】
【発明の効果】
樹脂中のビスアミドを、簡単、短時間で再現性良く定量分析する方法であることが、明らかである。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a method for determining bisamide contained as a lubricant in a resin.
[0002]
[Prior art]
Conventionally, when quantifying ethylene bisstearic acid amide in a resin, there is a method of extracting with hot chloroform or the like. However, according to this method, the bisamide is dissolved but the resin is not dissolved, so that it takes a long time to pulverize the resin, extract and concentrate the extract. There is also a question about reproducibility. (For example, see Non-Patent Document 1)
As another method, there is a method in which the amount of nitrogen is quantified and converted into ethylenebisstearic acid amide to calculate the amount of ethylenebisstearic acid amide contained in the sample. However, this method cannot be used when a nitrogen element is present in the resin structure or when an additive having a nitrogen element coexists.
[0003]
[Non-patent document 1]
"Polymer Analysis Handbook" (issued in 1985, Asakura Shoten Co., Ltd.)
[0004]
[Problems to be solved by the invention]
An object of the present invention is to provide a method for analyzing the amount of bisamide contained as a lubricant in a resin in a short time without requiring time for extraction / concentration.
[0005]
[Means for Solving the Problems]
That is, the present invention is as follows.
1. A method for quantitatively analyzing a bisamide in a resin composition containing a bisamide, comprising the steps of (1) dissolving the resin composition in a solvent that dissolves the resin and the bisamide, and subjecting the solution to gas chromatography / mass spectrometry. Then, the peak area is compared with the known amount of the bisamide and the bisamide standard in the solution, and then (2) the bisamide in the solution is readjusted to a concentration at which the bisamide is stably dissolved in the solvent. (3) A method for quantifying bisamide using an absolute calibration curve method, wherein the bisamide is separated and detected by gas chromatography / mass spectrometry.
[0006]
2. 2. The method according to the above item 1, wherein the concentration of the bisamide in the reconditioned polymer solution is 500 ppm or less.
3. 3. The method according to 1 or 2, wherein the solvent is hexafluoroisopropanol.
4. The method according to any one of the above items 1 to 3, wherein the purity of hexafluoroisopropanol is 99.5% or more.
5. The method according to any one of the above items 1 to 4, wherein the bisamide is ethylene bisstearic acid amide.
6. 6. The method according to any one of the above items 1 to 5, wherein the resin is a resin selected from a polyamide resin, a polyacetal resin, a polyester resin, an acrylic resin, a polycarbonate resin, and an alloy of these resins.
Hereinafter, the present invention will be described.
[0007]
According to the present invention, a resin composition containing a bisamide as a lubricant is dissolved, and the solution is subjected to gas chromatography / mass spectrometry to compare the peak area and the known amount of a bisamide and a bisamide standard in the solution. It is readjusted so that the concentration of bisamide in the solvent is not more than the concentration at which the bisamide is stably dissolved in the solvent, and used as a sample for quantitative determination. This is a quantification method using an absolute calibration curve method for bisamide, characterized in that this quantification sample is subjected to gas chromatography / mass spectrometry to separate and detect.
[0008]
The analysis target of the present invention is a resin composition containing a bisamide.
As the solvent of the present invention, a resin composition, that is, a solvent that dissolves both the resin and the bisamide is used. Formic acid, acetic acid, hexafluoroisopropanol.
The resin of the present invention is a thermoplastic resin, and is a polyamide resin, a polyacetal resin, a polyester resin, an acrylic resin, a polycarbonate resin, or an alloy of these resins. In particular, when a polyamide resin is used, hexafluoroisopropanol (hereinafter sometimes abbreviated as HFI) is preferably used as a solvent.
[0009]
Examples of the bisamide of the present invention include methylenebisstearic acid amide, ethylenebislauric acid amide, ethylenebisstearic acid amide, and ethylenebisoleic acid amide. The present invention is particularly effective for ethylene bisstearic acid amide.
In addition, ethylene bisstearic acid amide contains ethylene bispalmitic acid amide and ethylene palmitic acid stearic acid amide as impurities, and these are collectively referred to as ethylene bisstearic acid amide in the following description.
The concentration at which ethylenebisstearic acid amide is stably dissolved in hexafluoroisopropanol is preferably 500 ppm or less. For the calibration curve sample, ethylenebisstearic acid amide standard was dissolved in hexafluoroisopropanol, and three concentrations of 500 ppm or less were used. .
[0010]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, a specific description will be given based on examples.
[0011]
Embodiment 1
Polyamide 6 containing 1% ethylenebisstearic acid amide was produced as a trial. About 500 mg of the above pellets are dissolved in 20 ml of hexafluoroisopropanol. The concentration of ethylene bisstearic acid amide in the polymer solution is about 250 ppm.
The sample for quantitative determination was subjected to gas chromatography / mass spectrometry "6890" manufactured by Hewlett-Packard Company / "5973" manufactured by Hewlett-Packard Company to quantify ethylenebisstearic acid amide. Samples for the calibration curve were prepared by dissolving a standard ethylene bisstearic acid amide in hexafluoroisopropanol and using three concentrations of 500 ppm or less.
The amount of ethylene bisstearic acid amide determined by the absolute calibration curve method was 0.87%. That is, it is understood that the method of the present invention is simple and has excellent accuracy.
[0012]
Embodiment 2
Polyamide 6 containing 1% ethylene bisstearic acid amide was used as a sample.
About 100 mg of the above pellet is dissolved in 20 ml of HFIP. The concentration of ethylene bisstearic acid amide in the polymer solution is about 50 ppm.
The sample for quantitative determination was subjected to gas chromatography / mass spectrometry "6890" manufactured by Hewlett-Packard Company / "5973" manufactured by Hewlett-Packard Company to quantify ethylenebisstearic acid amide. Samples for the calibration curve were prepared by dissolving a sample of ethylenebisstearic acid amide in hexafluoroisopropanol and using three concentrations of 500 ppm or less.
The amount of ethylene bisstearic acid amide determined by the absolute calibration curve method was 0.85%.
[0013]
[Comparative Example 1]
Polyamide 6 containing about 1% ethylene bisstearic acid amide was used as a sample. Specifically, when about 2000 mg of the pellet was dissolved in 20 ml of HFIP, it was not completely dissolved, so the quantitative analysis was stopped.
[0014]
【The invention's effect】
It is clear that this is a method for simply and reproducibly quantitatively analyzing a bisamide in a resin in a short time.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003106806A JP2004309436A (en) | 2003-04-10 | 2003-04-10 | Bis-amide quantitative method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003106806A JP2004309436A (en) | 2003-04-10 | 2003-04-10 | Bis-amide quantitative method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2004309436A true JP2004309436A (en) | 2004-11-04 |
Family
ID=33468880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003106806A Pending JP2004309436A (en) | 2003-04-10 | 2003-04-10 | Bis-amide quantitative method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2004309436A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010161234A (en) * | 2009-01-08 | 2010-07-22 | Showa Denko Kk | Method of manufacturing light-emitting device, light-emitting device, and lighting system |
| CN109313204A (en) * | 2016-06-15 | 2019-02-05 | 豪夫迈·罗氏有限公司 | Improved D dimer assay calibration |
| CN114965778A (en) * | 2022-05-30 | 2022-08-30 | 江西威科油脂化学有限公司 | Method for determining palmitamide and stearamide in stearamide product |
-
2003
- 2003-04-10 JP JP2003106806A patent/JP2004309436A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010161234A (en) * | 2009-01-08 | 2010-07-22 | Showa Denko Kk | Method of manufacturing light-emitting device, light-emitting device, and lighting system |
| CN109313204A (en) * | 2016-06-15 | 2019-02-05 | 豪夫迈·罗氏有限公司 | Improved D dimer assay calibration |
| CN114965778A (en) * | 2022-05-30 | 2022-08-30 | 江西威科油脂化学有限公司 | Method for determining palmitamide and stearamide in stearamide product |
| CN114965778B (en) * | 2022-05-30 | 2023-11-17 | 江西威科油脂化学有限公司 | Determination method of palmitoyl acid amide and stearic acid amide in stearic acid amide product |
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