JPH01221445A - Polyethylene composition - Google Patents
Polyethylene compositionInfo
- Publication number
- JPH01221445A JPH01221445A JP33012688A JP33012688A JPH01221445A JP H01221445 A JPH01221445 A JP H01221445A JP 33012688 A JP33012688 A JP 33012688A JP 33012688 A JP33012688 A JP 33012688A JP H01221445 A JPH01221445 A JP H01221445A
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- reacting
- phosphite compound
- phosphite
- 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.)
- Granted
Links
- -1 Polyethylene Polymers 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 239000004698 Polyethylene Substances 0.000 title claims description 8
- 229920000573 polyethylene Polymers 0.000 title claims description 8
- 239000000126 substance Substances 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract description 2
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 238000011105 stabilization Methods 0.000 abstract description 2
- XHLCCKLLXUAKCM-UHFFFAOYSA-N octadecyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XHLCCKLLXUAKCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- 206010068188 Heat illness Diseases 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- XOWXZNFZAZBNST-UHFFFAOYSA-N OP(O)OP(O)O.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 Chemical compound OP(O)OP(O)O.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XOWXZNFZAZBNST-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JLXPQFBAFJZAQZ-UHFFFAOYSA-N o-[3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2,2,3-tridodecylpentadecanethioate Chemical compound CCCCCCCCCCCCC(CCCCCCCCCCCC)C(CCCCCCCCCCCC)(CCCCCCCCCCCC)C(=S)OCC(CO)(CO)CO JLXPQFBAFJZAQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本願発明はポリエチレン組成物に関し、詳しくは、特定
のフェノール系抗酸化剤及び特定のホスファイト化合物
を添加することによって、熱及び光の作用による劣化に
対して長期にわたって安定化されたポリエチレン組成物
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a polyethylene composition, and more particularly, the present invention relates to a polyethylene composition that is stable for a long period of time against deterioration due to the effects of heat and light by adding a specific phenolic antioxidant and a specific phosphite compound. The present invention relates to polyethylene compositions.
ポリエチレンは熱及び光の作用により劣化し、着色した
り、機械的強度が低下し使用に耐えなくなることが知ら
れている。かかる合成樹脂の劣化を防ぐ為にこれまで多
くの添加剤が単独であるいは種々組み合わせて用いられ
てきた。これらの添加剤の中でもホスファイト系の化合
物は合成樹脂に対して耐熱性、耐光性を付与し、しかも
合成樹脂の着色を抑制するという利点があり広く用いら
れてきた。これらのホスファイト化合物の中でも、トリ
ス（ノニルフェニル）ホスファイト、ジフェニルイソデ
シルホスファイト、ジステアリルペンタエリスリトール
ジホスファイト、テトラアルキルビスフェノールＡジホ
スファイト等は比較的その効果が大きく賞用されていた
。It is known that polyethylene deteriorates due to the action of heat and light, becoming discolored and having a reduced mechanical strength, making it unusable. In order to prevent such deterioration of synthetic resins, many additives have been used singly or in various combinations. Among these additives, phosphite-based compounds have been widely used because they have the advantage of imparting heat resistance and light resistance to synthetic resins and suppressing discoloration of synthetic resins. Among these phosphite compounds, tris(nonylphenyl) phosphite, diphenylisodecyl phosphite, distearylpentaerythritol diphosphite, tetraalkyl bisphenol A diphosphite, and the like have been used for their relatively large effects.
しかしながら、従来用いられていたホスファイト化合物
はその効果が比較的短時間で失なわれることが多く、特
に屋外あるいは湿潤雰囲気で使用するとその効果が急速
に失なわれることが多かった。また、従来用いられてき
たホスファイト化合物の高温での安定化効果は一時的な
ものにすぎず、長期的な安定化効果は小さく実用上まだ
まだ不満足なものであった。However, conventionally used phosphite compounds often lose their effectiveness in a relatively short time, especially when used outdoors or in a humid atmosphere. Furthermore, the stabilizing effect of conventionally used phosphite compounds at high temperatures is only temporary, and the long-term stabilizing effect is small and still unsatisfactory in practical terms.
本発明者等はかかる現状に鑑み鋭意検討を重ねた結果、
ポリエチレン１００重量部に、（ａ）ステアリル−３，
５−ジ第三ブチル−４−ヒドロキシフェニルプロピオネ
ート０．００１〜５重量部および（１））次の式（Ｉ）
で示される有機ホスファイト化合物０．００１〜５重量
部を併用添加することにより、長期に渡って安定化され
ることを見い出し、発明に到達した。In view of the current situation, the inventors of the present invention have conducted extensive studies, and have found that
To 100 parts by weight of polyethylene, (a) stearyl-3,
0.001 to 5 parts by weight of 5-di-tert-butyl-4-hydroxyphenylpropionate and (1)) the following formula (I)
The inventors have discovered that by adding 0.001 to 5 parts by weight of an organic phosphite compound represented by the formula above, stabilization can be achieved over a long period of time, and the invention has been achieved.
以下、上記要旨をもってなる本発明について詳述する。Hereinafter, the present invention having the above-mentioned summary will be explained in detail.
本発明で用いられる前記式（１）で示される有機ホスフ
ァイト化合物は、例えば、２，６−ジ第三ブチル−４−
メチルフェノールと三塩化リンとを反応させ、次いでペ
ンタエリスリトールと反応させるか、または三塩化リン
に代えてトリフェニルホスファイトまたはトリメチルホ
スファイトを反応させることによって製造することがで
きる。The organic phosphite compound represented by the formula (1) used in the present invention is, for example, 2,6-di-tert-butyl-4-
It can be produced by reacting methylphenol and phosphorus trichloride and then reacting with pentaerythritol, or by reacting triphenyl phosphite or trimethyl phosphite in place of phosphorus trichloride.
また、ジクロロ（またはシメチノペジフェニル）ペンク
エリスリトールジホスファイトと２．６−ジ第三ブチル
−４−メチルフェノールとを反応させることによっても
製造することができる。It can also be produced by reacting dichloro (or cimetinopediphenyl) penquerythritol diphosphite with 2,6-di-tert-butyl-4-methylphenol.
次にホスファイト化合物の具体的な合成例を示す。Next, a specific example of synthesis of a phosphite compound will be shown.
合成例１
ビス（２，６−ジ第三ブチル４−メチルフェニル）ペン
クエリスリトールジホスファイトの合成２．６−ジ第三
ブチル−４−メチルフェノール１１．０２ｇ （０，０
５モル）とトリエチルアミン６．１０ｇ （０，０６モ
ル）をクロロホルム５Ｑｍｆｆｉに溶解した。この溶液
に室温で三塩化リンＥ＋、８８ｇ （０，０５モル）を
滴下後、Ｎ２気流下５０℃で９時間反応した。次いてペ
ンクエリスリトール３．４１ｇ （０，０２５モル）と
トリエチルアミン１６．２０ｇ （０，１２モル）を加
え、Ｎ２気流下５５〜８０℃で９時間反応した。反応後
クロスホルムを留去し、これをベンゼンに溶解して、Ｎ
（Ｃ２Ｈ５）３・ＨＣＩを除去、次いでベンゼンによる
再結晶により融点２４４℃の固体を得た。Synthesis Example 1 Synthesis of bis(2,6-di-tert-butyl-4-methylphenyl) penquerythritol diphosphite 2.6-di-tert-butyl-4-methylphenol 11.02 g (0,0
5 mol) and 6.10 g (0.06 mol) of triethylamine were dissolved in chloroform 5Qmffi. After 88 g (0.05 mol) of phosphorus trichloride E+ was added dropwise to this solution at room temperature, the mixture was reacted at 50° C. for 9 hours under a N 2 stream. Next, 3.41 g (0.025 mol) of penquerythritol and 16.20 g (0.12 mol) of triethylamine were added, and the mixture was reacted for 9 hours at 55-80° C. under a N2 stream. After the reaction, crossform was distilled off, dissolved in benzene, and N
(C2H5)3.HCI was removed and then recrystallized with benzene to obtain a solid with a melting point of 244°C.
本発明の組成物に光安定剤を添加するならば光安定性を
向上させ得るので、使用目的に応じて適宜これらを選択
して使用することが可能である。If a photostabilizer is added to the composition of the present invention, the photostability can be improved, so it is possible to appropriately select and use these depending on the purpose of use.
これらにはベンゾフェノン系、ベンゾトリアソール系、
サリシレート系、置換アクリロニトリル系、ピペリジン
系、各種の金属願塩又は金属キレート、特にニッケル又
はクロムの塩又はキレート類、トリアジン系などが包有
される。These include benzophenone, benzotriazole,
Included are salicylates, substituted acrylonitriles, piperidine, various metal salts or metal chelates, especially nickel or chromium salts or chelates, triazine, and the like.
本発明の組成物に硫黄系抗酸化剤を含有させることもで
きる。硫黄系抗酸化剤としては、たとえば、ジステアリ
ルチオジプロピオネート、ジラウリルチオジプロピオネ
ート、ペンタエリスリトールテトララウリルチオプロピ
オネートなどがあげられる。The composition of the present invention may also contain a sulfur-based antioxidant. Examples of the sulfur-based antioxidant include distearylthiodipropionate, dilaurylthiodipropionate, pentaerythritol tetralaurylthiopropionate, and the like.
その他必要に応じて、例えば有機酸金属塩、エポキシ化
合物、顔料、充填剤、発泡剤、アミン系抗酸化剤、帯電
防止剤、防曇剤、プレートアウト防止剤、表面処理剤、
滑剤、難燃剤、蛍光剤、防黴剤、殺菌剤、金属不活性化
剤、光劣化剤、赤外線吸収剤、加工助剤、離型剤、補強
剤などを包有させることができる。In addition, as necessary, for example, organic acid metal salts, epoxy compounds, pigments, fillers, foaming agents, amine antioxidants, antistatic agents, antifogging agents, plate-out prevention agents, surface treatment agents,
It can contain lubricants, flame retardants, fluorescent agents, antifungal agents, bactericidal agents, metal deactivators, photodegradants, infrared absorbers, processing aids, mold release agents, reinforcing agents, and the like.
次に示す実施例は本発明による組成物の効果を示すもの
であるが、本発明はこれらの実施例によって限定される
ものではない。The following examples illustrate the effects of the composition according to the present invention, but the present invention is not limited by these examples.
実施例１
次の配合物を１５０℃で５分間ミキシングロールで混練
し、次いで１５０℃、１８０ｋｇ／ｃｎｉの条件で５分
間圧縮成型を行い、厚さ０．１ｍｍのシートを作成した
。Example 1 The following formulation was kneaded with a mixing roll at 150°C for 5 minutes, and then compression molded at 150°C and 180 kg/cni for 5 minutes to create a sheet with a thickness of 0.1 mm.
このシートを１０１０Ｘ２０の試験片として、アルミ箔
よ、１５０℃のギヤーオーブン中で熱安定性試験を行っ
た。結果を表−１に示す。This sheet was used as a 1010 x 20 test piece, and a thermal stability test was conducted using aluminum foil in a gear oven at 150°C. The results are shown in Table-1.
〈配 合〉
ジステアリルチオジプロピオネート０．３ホスファイト
化合物（表−１） ０． １表−１
出願人代理人 古 谷 馨<Formulation> Distearylthiodipropionate 0.3 Phosphite compound (Table-1) 0. Table 1-1 Applicant's agent Kaoru Furuya
Claims (1)
５−ジ第三ブチル−４−ヒドロキシフェニルプロピオネ
ート０．００１〜５重量部および（ｂ）次の式（ I ）
で示される有機ホスファイト化合物０．００１〜５重量
部を添加して成る安定化されたポリエチレン組成物。 ▲数式、化学式、表等があります▼（ I ）[Claims] To 100 parts by weight of polyethylene, (a) stearyl-3,
0.001 to 5 parts by weight of 5-di-tert-butyl-4-hydroxyphenylpropionate and (b) the following formula (I)
A stabilized polyethylene composition comprising 0.001 to 5 parts by weight of an organic phosphite compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33012688A JPH01221445A (en) | 1988-12-27 | 1988-12-27 | Polyethylene composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33012688A JPH01221445A (en) | 1988-12-27 | 1988-12-27 | Polyethylene composition |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5659480A Division JPS56152863A (en) | 1980-04-28 | 1980-04-28 | Synthetic resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01221445A true JPH01221445A (en) | 1989-09-04 |
| JPH0346494B2 JPH0346494B2 (en) | 1991-07-16 |
Family
ID=18229097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33012688A Granted JPH01221445A (en) | 1988-12-27 | 1988-12-27 | Polyethylene composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01221445A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7851002B2 (en) | 2002-06-07 | 2010-12-14 | Mantrose-Haeuser Company, Inc. | Methods for preserving fresh produce |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5425951A (en) * | 1977-07-29 | 1979-02-27 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
| JPS5443952A (en) * | 1977-09-14 | 1979-04-06 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
-
1988
- 1988-12-27 JP JP33012688A patent/JPH01221445A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5425951A (en) * | 1977-07-29 | 1979-02-27 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
| JPS5443952A (en) * | 1977-09-14 | 1979-04-06 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7851002B2 (en) | 2002-06-07 | 2010-12-14 | Mantrose-Haeuser Company, Inc. | Methods for preserving fresh produce |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0346494B2 (en) | 1991-07-16 |
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