JPH0116266B2 - - Google Patents
Info
- Publication number
- JPH0116266B2 JPH0116266B2 JP57080280A JP8028082A JPH0116266B2 JP H0116266 B2 JPH0116266 B2 JP H0116266B2 JP 57080280 A JP57080280 A JP 57080280A JP 8028082 A JP8028082 A JP 8028082A JP H0116266 B2 JPH0116266 B2 JP H0116266B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl acetate
- acetic acid
- ethylene
- acetate copolymer
- weight
- 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
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- -1 alkaline earth metal salt Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001354 calcium citrate Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004868 gas analysis Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 101100293276 Caenorhabditis elegans cra-1 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- GUPPESBEIQALOS-UHFFFAOYSA-L calcium tartrate Chemical compound [Ca+2].[O-]C(=O)C(O)C(O)C([O-])=O GUPPESBEIQALOS-UHFFFAOYSA-L 0.000 description 1
- 239000001427 calcium tartrate Substances 0.000 description 1
- 235000011035 calcium tartrate Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WPUMTJGUQUYPIV-JIZZDEOASA-L disodium (S)-malate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)CC([O-])=O WPUMTJGUQUYPIV-JIZZDEOASA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- OWFJMGQSOHDIPP-UHFFFAOYSA-L monocalcium citrate Chemical compound [Ca+2].OC(=O)CC(O)(C(O)=O)CC([O-])=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O OWFJMGQSOHDIPP-UHFFFAOYSA-L 0.000 description 1
- 235000012663 monocalcium citrate Nutrition 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 229940086065 potassium hydrogentartrate Drugs 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- NKAAEMMYHLFEFN-ZVGUSBNCSA-M sodium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound [Na+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O NKAAEMMYHLFEFN-ZVGUSBNCSA-M 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、エチレン−酢酸ビニル共重合体の低
酢酸臭化法に関するものである。
エチレン−酢酸ビニル共重合体は、フイルム、
成形品、接着剤、高分子改質材等の広い分野で使
用されているが、原料の酢酸ビニル単量体の臭い
と、成形加工時に発生する酢酸の臭いの為に、製
品から臭いが発生し、嫌われる場合がある。この
うち、酢酸ビニル単量体臭は、共重合体製造時
に、物理的にそのほとんどを除去することができ
るが、成形時に発生する酢酸臭は、物理的に除去
することが困難であり、従来より、酸化カルシウ
ム（特公昭37−6626号）、有機金属塩と脂肪族多
価アルコール（特公昭47−13855号）、高級脂肪族
金属化合物（特公昭47−31690号）、、又は
族の金属水酸化物、酸化物、炭酸塩又はアルコラ
ート（特開昭46−12338号）、金属石けんと有機亜
燐酸エステル等（特開昭49−37116号）、活性炭
（特開昭49−99545号）、有機アミン類（特開昭49
−99550号）、油溶性アルキルアリルスルホン酸塩
（特開昭50−55646号）等を添加して、高温加工時
の遊離酢酸の発生を抑える方法が提出されてい
る。しかるに、これらの添加物のほとんどは製品
の透明性を阻害したり、着色したり、異臭を発生
したり、また成形機内面を腐蝕させる危険性があ
り、好ましいとは言えない。
しかして、本発明者は、エチレン−酢酸ビニル
共重合体に対して炭素数６以上のオキシ酸のアル
カリ又はアルカリ土金属塩を添加することによ
り、上記の各種の公知方法に比べて効果的に高温
成形時の遊離酢酸の発生を抑え、製品の透明性を
阻害せず、食品包装用基材として使用した場合で
も、人体に悪影響を与えない。エチレン−酢酸ビ
ニル共重合体の低酢酸臭化法を見出し、本発明を
完成した。
本発明に使用する炭素数６以下のオキシ酸のア
ルカリ又はアルカリ土金属塩は、グリコール酸ナ
トリウム、乳酸カルシウム、Ｌ−またはDL−リ
ンゴ酸ナトリウム、酒石酸カリウム、酒石酸ナト
リウム、酒石酸カルシウム、酒石酸ナトリウムカ
リウム、酒石酸水素ナトリウム、酒石酸水素カリ
ウム、クエン酸カリウム、クエン酸ナトリウム、
クエン酸カルシウム、クエン酸一カルシウム等か
ら選ばれた化合物である。
上記塩類が遊離酢酸の発生を抑える理由は必ら
ずしも明らかではないが、上記塩類の原料と考え
られるオキシ酸の25℃での電離定数がいずれも酢
酸のそれよりも大きいことから、オキシ酸塩が遊
離酢酸と反応して、遊離酢酸発生の連鎖反応を抑
える為であると推定される。本発明において、エ
チレン−酢酸ビニル共重合体とは、エチレンと酢
酸ビニルから成る共重合体であり、添加するオキ
シ酸のアルカリ又はアルカリ土金属塩の適量は、
共重合体の組成によつて異なるが、いずれも0.2
〜５重量部の範囲の添加により、共重合体を低酢
酸臭化できる。
本発明において、酸化防止剤、スリツプ剤、ア
ンチブロツク剤、紫外線防止剤、顔料、無機充て
ん剤等、通常エチレン酢酸ビニル共重合体に添加
する添加剤を併用しても何らさしつかえない。
実施例 １
メルトインデツクス3.0、酢酸ビニル含量18重
量％のエチレン酢酸ビニル共重合体50ｇに対し、
各種化合物を0.5ｇ添加し、ブラベンダープラス
グラフで150℃で５分間混練した。この混合物を
150℃で５分間プレスしてシート化し、ペレツト
化した。このペレツトを、Ｆ−45ヘツドスペース
アナライザー（パーキンエルマー製）によりガス
分析した。方法は、５ｇのペレツトを入れた容量
20mlのバイヤルを100℃で２時間保持し、1.5バー
ルのヘリウムで３秒間、、バイヤルのヘツドスペ
ース部のガスを100℃のカラム（PEG−1500）に
導入し、感度１×４でRT（保持時間）1.6分に現
われた酢酸のピークをクロマトパツクCRA−１
（島津製作所製）で記録した。
次に、混合物をプレス成形により100μのフイ
ルムとし、曇り度の測定をNDH−2D（日本電色
工業製）で測定した。
結果を表１に示した。
The present invention relates to a method for reducing acetic acid bromination of ethylene-vinyl acetate copolymers. Ethylene-vinyl acetate copolymer can be used as a film,
It is used in a wide range of fields such as molded products, adhesives, and polymer modifiers, but the product produces an odor due to the odor of the raw material vinyl acetate monomer and the odor of acetic acid generated during the molding process. and may be disliked. Of these, most of the vinyl acetate monomer odor can be physically removed during copolymer production, but the acetic acid odor generated during molding is difficult to physically remove, and compared to conventional methods. , calcium oxide (Japanese Patent Publication No. 37-6626), organometallic salts and aliphatic polyhydric alcohols (Japanese Patent Publication No. 47-13855), higher aliphatic metal compounds (Japanese Patent Publication No. 47-31690), or group metal water Oxides, oxides, carbonates or alcoholates (JP-A-46-12338), metal soaps and organic phosphites, etc. (JP-A-49-37116), activated carbon (JP-A-49-99545), organic Amines (Unexamined Japanese Patent Publication No. 1973)
A method of suppressing the generation of free acetic acid during high-temperature processing has been proposed by adding an oil-soluble alkylaryl sulfonate (Japanese Patent Application Laid-open No. 50-55646). However, most of these additives are undesirable because they impair the transparency of the product, cause coloring, generate a strange odor, and have the risk of corroding the inner surface of the molding machine. Therefore, the present inventor has discovered that by adding an alkali or alkaline earth metal salt of an oxyacid having 6 or more carbon atoms to an ethylene-vinyl acetate copolymer, the method can be more effectively used than the various known methods described above. It suppresses the generation of free acetic acid during high-temperature molding, does not impair product transparency, and does not have any adverse effects on the human body even when used as a base material for food packaging. The present invention was completed by discovering a low acetic acid bromination method for ethylene-vinyl acetate copolymer. The alkali or alkaline earth metal salts of oxyacids having 6 or less carbon atoms used in the present invention include sodium glycolate, calcium lactate, sodium L- or DL-malate, potassium tartrate, sodium tartrate, calcium tartrate, potassium sodium tartrate, Sodium hydrogen tartrate, potassium hydrogen tartrate, potassium citrate, sodium citrate,
It is a compound selected from calcium citrate, monocalcium citrate, etc. The reason why the above salts suppress the generation of free acetic acid is not necessarily clear, but since the ionization constants at 25°C of the oxyacids considered to be the raw materials for the above salts are all larger than that of acetic acid, It is presumed that this is because the acid salt reacts with free acetic acid and suppresses the chain reaction of generating free acetic acid. In the present invention, the ethylene-vinyl acetate copolymer is a copolymer consisting of ethylene and vinyl acetate, and the appropriate amount of the alkali or alkaline earth metal salt of oxyacid to be added is as follows:
It varies depending on the composition of the copolymer, but in all cases it is 0.2
By adding in an amount of 5 parts by weight, the copolymer can be reduced in acetic acid bromination. In the present invention, there is no problem in using additives normally added to ethylene-vinyl acetate copolymers, such as antioxidants, slip agents, anti-blocking agents, ultraviolet inhibitors, pigments, and inorganic fillers. Example 1 For 50 g of ethylene vinyl acetate copolymer with a melt index of 3.0 and a vinyl acetate content of 18% by weight,
0.5g of various compounds were added and kneaded at 150°C for 5 minutes using a Brabender Plus graph. this mixture
The mixture was pressed at 150°C for 5 minutes to form a sheet and pelletize. This pellet was subjected to gas analysis using an F-45 head space analyzer (manufactured by PerkinElmer). The method is to use a capacity containing 5g of pellets.
A 20 ml vial was kept at 100°C for 2 hours, then heated with helium at 1.5 bar for 3 seconds. Chromatopack CRA-1 to detect the acetic acid peak that appeared at 1.6 minutes (time).
(manufactured by Shimadzu Corporation). Next, the mixture was formed into a 100 μm film by press molding, and the degree of haze was measured using NDH-2D (manufactured by Nippon Denshoku Kogyo). The results are shown in Table 1.
【表】【table】
【表】
実施例 ２
メルトインデツクス0.5、酢酸ビニル含量18重
量％のエチレン−酢酸ビニル共重合体50ｇに対
し、各種塩類を0.1ｇ添加し、ブラベンダープラ
スグラフで150℃で５分間混練した。
この混合物を実施例１と同様に、酢酸ガス分析
および曇り度を測定した。
結果を表２に示した。[Table] Example 2 To 50 g of an ethylene-vinyl acetate copolymer having a melt index of 0.5 and a vinyl acetate content of 18% by weight, 0.1 g of various salts were added and kneaded at 150° C. for 5 minutes using a Brabender Plus graph. This mixture was subjected to acetic acid gas analysis and haze measurement in the same manner as in Example 1. The results are shown in Table 2.
Claims (1)
対し、炭素数６以下のオキシ酸のアルカリ又はア
ルカリ土金属塩を0.2〜５重量部添加することを
特徴とするエチレン−酢酸ビニル共重合体の低酢
酸臭化法。1. A low-density ethylene-vinyl acetate copolymer characterized by adding 0.2 to 5 parts by weight of an alkali or alkaline earth metal salt of an oxyacid having 6 or less carbon atoms to 100 parts by weight of the ethylene-vinyl acetate copolymer. Acetic acid bromide method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8028082A JPS58198554A (en) | 1982-05-14 | 1982-05-14 | Method for reducing acetic acid odor of ethylene/vinyl acetate copolymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8028082A JPS58198554A (en) | 1982-05-14 | 1982-05-14 | Method for reducing acetic acid odor of ethylene/vinyl acetate copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58198554A JPS58198554A (en) | 1983-11-18 |
| JPH0116266B2 true JPH0116266B2 (en) | 1989-03-23 |
Family
ID=13713856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8028082A Granted JPS58198554A (en) | 1982-05-14 | 1982-05-14 | Method for reducing acetic acid odor of ethylene/vinyl acetate copolymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58198554A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4761437A (en) * | 1987-01-09 | 1988-08-02 | Christie Sharon K | Process for preparing fragrance chips |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56120740A (en) * | 1980-02-27 | 1981-09-22 | Sumitomo Chem Co Ltd | Crosslinkable polyethylene resin composition having no discoloration effect to copper |
-
1982
- 1982-05-14 JP JP8028082A patent/JPS58198554A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56120740A (en) * | 1980-02-27 | 1981-09-22 | Sumitomo Chem Co Ltd | Crosslinkable polyethylene resin composition having no discoloration effect to copper |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58198554A (en) | 1983-11-18 |
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