JP6150180B2 - 酸素吸収剤組成物及び酸素吸収剤包装体 - Google Patents
酸素吸収剤組成物及び酸素吸収剤包装体 Download PDFInfo
- Publication number
- JP6150180B2 JP6150180B2 JP2014533091A JP2014533091A JP6150180B2 JP 6150180 B2 JP6150180 B2 JP 6150180B2 JP 2014533091 A JP2014533091 A JP 2014533091A JP 2014533091 A JP2014533091 A JP 2014533091A JP 6150180 B2 JP6150180 B2 JP 6150180B2
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- Prior art keywords
- group
- oxygen
- oxygen absorbent
- compound
- absorbent composition
- Prior art date
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D81/00—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents
- B65D81/24—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants
- B65D81/26—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators
- B65D81/266—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators for absorbing gases, e.g. oxygen absorbers or desiccants
- B65D81/268—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators for absorbing gases, e.g. oxygen absorbers or desiccants the absorber being enclosed in a small pack, e.g. bag, included in the package
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- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
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- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3409—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of gases, e.g. fumigation; Compositions or apparatus therefor
- A23L3/3418—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of gases, e.g. fumigation; Compositions or apparatus therefor in a controlled atmosphere, e.g. partial vacuum, comprising only CO2, N2, O2 or H2O
- A23L3/3427—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of gases, e.g. fumigation; Compositions or apparatus therefor in a controlled atmosphere, e.g. partial vacuum, comprising only CO2, N2, O2 or H2O in which an absorbent is placed or used
- A23L3/3436—Oxygen absorbent
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Description
〔1〕
テトラリン環を2つ以上有する化合物(A)、及び遷移金属触媒を含有し、
前記化合物(A)が、下記一般式(1)〜(6)からなる群より選ばれる少なくともいずれかにより表される化合物である、酸素吸収剤組成物。
(式中、Rは、それぞれ独立して、1価の置換基を表し、前記1価の置換基は、ハロゲン原子、アルキル基、アルケニル基、アルキニル基、アリール基、複素環基、シアノ基、ヒドロキシ基、カルボキシル基、エステル基、アミド基、ニトロ基、アルコキシ基、アリールオキシ基、アシル基、アミノ基、チオール基、アルキルチオ基、アリールチオ基、複素環チオ基、及びイミド基からなる群より選ばれる少なくとも1種であり、Rは、置換基を更に有していてもよい。少なくとも1つのテトラリン環のベンジル位には1つ以上の水素原子が結合している。Xは、芳香族炭化水素基、飽和若しくは不飽和の脂環式炭化水素基、直鎖状若しくは分岐状の飽和若しくは不飽和の脂肪族炭化水素基、及び複素環基からなる群より選ばれる少なくとも1つの基を含有する2価の基を表す。Yは、エステル基又はアミド基を表す。mは0〜7の整数を表し、nは0〜3の整数を表し、pは0〜4の整数を表し、qは0〜6の整数を表し、tは0〜6の整数を表す。)
〔2〕
前記化合物(A)の分子量は、276〜1000である、〔1〕に記載の酸素吸収剤組成物。
〔3〕
担体物質を更に含有する、〔1〕又は〔2〕に記載の酸素吸収剤組成物。
〔4〕
前記担体物質が、合成ケイ酸カルシウム、珪藻土、シリカ、及び活性炭からなる群より選ばれる少なくとも1種である、〔3〕に記載の酸素吸収剤組成物。
〔5〕
前記化合物(A)100質量部に対して、前記担体物質を10〜1000質量部含む、〔3〕又は〔4〕に記載の酸素吸収剤組成物。
〔6〕
前記遷移金属触媒が、マンガン、鉄、コバルト、ニッケル、及び銅からなる群より選ばれる少なくとも1種の遷移金属を含む、〔1〕〜〔5〕のいずれか一項に記載の酸素吸収剤組成物。
〔7〕
前記遷移金属触媒を、前記化合物(A)100質量部に対して、遷移金属量として0.001〜10質量部含む、〔1〕〜〔6〕のいずれか一項に記載の酸素吸収剤組成物。
〔8〕
〔1〕〜〔7〕のいずれか一項に記載の酸素吸収剤組成物と、
前記酸素吸収剤組成物を包装する通気性包装材料と、
を備える、酸素吸収剤包装体。
本実施形態の酸素吸収剤組成物は、テトラリン環を2つ以上有する化合物(A)、及び遷移金属触媒を含有する。本実施形態の酸素吸収剤組成物は、高湿度下であっても、低湿度下であっても優れた酸素吸収能を発揮することができる。そして、臭気を抑制することもできる。さらには、本実施形態の酸素吸収剤組成物は、酸素吸収のための鉄を用いなくてもよいため、非鉄系酸素吸収剤組成物(鉄を実質的に含まない)とすることができる。
本実施形態の酸素吸収剤組成物は、熱可塑性樹脂等の樹脂を更に含有してもよい(以下、樹脂を含有するものを「酸素吸収性樹脂組成物」という場合がある。)。酸素吸収性樹脂組成物とする方法としては、例えば、上記した酸素吸収剤組成物と熱可塑性樹脂を押出機によって混練する方法等が挙げられる。混練条件についても、使用する原料の諸物性等を考慮して適宜選択することができる。
上記した酸素吸収剤組成物又は酸素吸収性樹脂組成物は、通気性包装材料で包装することで、酸素吸収剤包装体として用いることができる。すなわち、本実施形態の酸素吸収剤包装体としては、上記した酸素吸収剤組成物(あるいはこれを含む酸素吸収性樹脂組成物)と、これを包装する通気性包装材料と、を備える酸素吸収剤包装体が挙げられる。本実施形態の酸素吸収剤包装体は、上記したような樹脂を含まない酸素吸収剤組成物を使用してもよいし、樹脂を配合した酸素吸収性樹脂組成物を使用してもよく、用途等を考慮して、選択することができる。
温度計、分縮器、全縮器、及び撹拌装置を備えた300mL反応器に、アジピン酸ジメチル10.8g(62mmol)、テトラリンメタノール30.0g(185mmol)を仕込み、130℃まで昇温した。チタンテトラブトキシドモノマー58mg(Ti換算で200ppm)を添加した後に、200℃まで昇温し、生成するメタノールを系外へ除きながら反応を行った。メタノールの生成が止まった後、室温まで冷却し、未反応のテトラリンメタノールを減圧除去した後に、再結晶により、ジエステル化合物Aを得た。示差熱・熱重量同時測定装置(島津製作所社製、商品名「DTG−60」)を用いて、得られた化合物の3%重量減少温度を測定した。3%重量減少温度の測定は、10℃/分の昇温速度で500℃まで昇温して行った。得られた化合物の構造式及び3%重量減少温度を表1に示す。一例として、NMRの分析結果を以下に示す。1H‐NMR(500MHz CDCl3)δ7.02−7.09(6H m)、5.52(4H s)、2.68−2.78(8H m)、2.27−2.39(4H m)、1.73−1.84(8H m)、1.60−1.69(4H m)。以下の合成例についても、特に断りがない限り、同様の手法によって化合物の構造を確認した。
アジピン酸ジメチルに代え、セバシン酸ジメチルを用い、その重量を14.3g(62mmol)とした他は、合成例1と同様の操作を行い、ジエステル化合物Bを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。一例として、NMRの分析結果を以下に示す。1H‐NMR(500MHz CDCl3)δ7.03−7.10(6H m)、5.50(4H s)、2.68−2.79(8H m)、2.26−2.39(4H m)、1.73−1.84(8H m)、1.60−1.69(4H m)、1.25−1.34(8H m)。
アジピン酸ジメチルに代え、コハク酸ジメチルを用い、その重量を9.1g(62mmol)とした他は、合成例1と同様の操作を行い、ジエステル化合物Cを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。
アジピン酸ジメチルに代え、フタル酸ジメチルを用い、その重量を12.0g(62mmol)とした他は、合成例1と同様の操作を行い、ジエステル化合物Dを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。
アジピン酸ジメチルに代え、イソフタル酸ジメチルを用い、その重量を12.0g(62mmol)とした他は、合成例1と同様の操作を行い、ジエステル化合物Eを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。
アジピン酸ジメチルに代え、テレフタル酸ジメチルを用い、その重量を12.0g(62mmol)とした他は、合成例1と同様の操作を行い、ジエステル化合物Fを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。なお、一例として、NMRの分析結果を以下に示す。1H‐NMR(500MHz CDCl3)δ8.06−8.14(4H m)、7.04−7.22(6H m)、5.30(4H s)、2.70−2.87(8H m)、1.74−1.87(8H m)。
温度計、撹拌装置を備えた500mL反応容器にテトラリン118.98g(900mmol)、メタンスルホン酸17.3g(180mmol)を仕込み、窒素置換した。室温にて滴下ろうとからホルマリン37%水溶液14.6g(ホルムアルデヒド換算で180mmol)を45分かけて滴下した。そのまま2時間攪拌した後に、ヘキサンで希釈後、NaHCO3水を滴下し反応を終了した。ヘキサンで抽出後、硫酸マグネシウムで乾燥し、濾過した。そして、溶媒留去を行い粗生成物を得た。得られた粗生成物からバス温度150℃、圧力:0torrにてテトラリンを除去した後、シリカゲルカラムクロマトグラフィーにより不飽和炭化水素Gを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。
ホルマリン水溶液に代え、アセトアルデヒド90%水溶液を用い、その重量を8.8g(アセトアルデヒド換算で180mmol)とした他は、合成例7の合成と同様の操作を行い、不飽和炭化水素Hを得た。得られた化合物の構造式及び3%重量減少温度を表1に示す。
ジエステル化合物A100質量部に、シリカゾル(商品名「MEK−ST 40D」、日産化学工業社製、メチルエチルケトン60質量%含有)750質量部と、コバルト量が0.4質量部となるように2−エチルヘキサン酸コバルトを加えて、窒素雰囲気下で、70℃で1時間撹拌した後、メチルエチルケトンを減圧留去、粉末化し、粒状物(粒状酸素吸収剤)を作製した。
次に、アルミ箔積層フィルムからなるガスバリア袋を2つ用意した。そして、得られた粒状酸素吸収剤1gを、空気500ccとともにガスバリア袋内にそれぞれ充填した。そして、一方の袋内の相対湿度を100%に調整し、他方の袋内の相対湿度を30%に調整した後、それぞれ密封した。このようにして得られた密封体の袋内酸素濃度を測定した。そして、この密封体を23℃で14日間保管して、保管後の袋内酸素濃度を測定した。これらの濃度から、14日間に酸素吸収剤が吸収した酸素の総量を算出した。算出した酸素の総量から、酸素吸収剤1g当たりの酸素吸収量(「cc/g−剤」)及び各化合物1g当たりの酸素吸収量(「cc/g−化合物」)をそれぞれ算出した。また、以下の評価基準に基づき、酸素吸収前後の臭気を官能評価した。これらの測定結果を表2に示した。
◎ 化合物自体に臭気がなく、酸素吸収前後ともに臭気なし
○ 化合物自体に若干臭気があるものの、酸素吸収前後で臭気の変化なし
× 酸素吸収後に臭気が増大
ジエステル化合物Aをジエステル化合物Bに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
ジエステル化合物Aをジエステル化合物Cに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
ジエステル化合物Aをジエステル化合物Dに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
ジエステル化合物Aをジエステル化合物Eに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
ジエステル化合物Aをジエステル化合物Fに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
不飽和炭化水素G100質量部に対して、コバルト量が0.1質量部となるように2−エチルヘキサン酸コバルトを加えて攪拌し溶液を調製した。この溶液を珪藻土(商品名「RC417」、昭和化学工業社製)133質量部に含侵させて、粒状物(粒状酸素吸収剤)を作製した。粒状酸素吸収剤の充填量を0.5gに変更した以外は、実施例1と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
不飽和炭化水素Gを不飽和炭化水素Hに変更した以外は、実施例7と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
不飽和炭化水素Gを1,5−ジメチルテトラリンに変更した以外は、実施例7と同様にして酸素吸収量の測定及び酸素吸収前後の臭気の官能評価を行った。これらの結果を表2に示した。
Claims (8)
- テトラリン環を2つ以上有する化合物(A)、及び遷移金属触媒を含有し、
前記化合物(A)が、下記一般式(1)〜(6)からなる群より選ばれる少なくともいずれかにより表される化合物である、酸素吸収剤組成物。
(式中、Rは、それぞれ独立して、1価の置換基を表し、前記1価の置換基は、ハロゲン原子、アルキル基、アルケニル基、アルキニル基、アリール基、複素環基、シアノ基、ヒドロキシ基、カルボキシル基、エステル基、アミド基、ニトロ基、アルコキシ基、アリールオキシ基、アシル基、アミノ基、チオール基、アルキルチオ基、アリールチオ基、複素環チオ基、及びイミド基からなる群より選ばれる少なくとも1種であり、Rは、置換基を更に有していてもよい。少なくとも1つのテトラリン環のベンジル位には1つ以上の水素原子が結合している。Xは、芳香族炭化水素基、飽和若しくは不飽和の脂環式炭化水素基、直鎖状若しくは分岐状の飽和若しくは不飽和の脂肪族炭化水素基、及び複素環基からなる群より選ばれる少なくとも1つの基を含有する2価の基を表す。Yは、エステル基又はアミド基を表す。mは0〜7の整数を表し、nは0〜3の整数を表し、pは0〜4の整数を表し、qは0〜6の整数を表し、tは0〜6の整数を表す。) - 前記化合物(A)の分子量は、276〜1000である、請求項1に記載の酸素吸収剤組成物。
- 担体物質を更に含有する、請求項1又は2に記載の酸素吸収剤組成物。
- 前記担体物質が、合成ケイ酸カルシウム、珪藻土、シリカ、及び活性炭からなる群より選ばれる少なくとも1種である、請求項3に記載の酸素吸収剤組成物。
- 前記化合物(A)100質量部に対して、前記担体物質を10〜1000質量部含む、請求項3又は4に記載の酸素吸収剤組成物。
- 前記遷移金属触媒が、マンガン、鉄、コバルト、ニッケル、及び銅からなる群より選ばれる少なくとも1種の遷移金属を含む、請求項1〜5のいずれか一項に記載の酸素吸収剤組成物。
- 前記遷移金属触媒を、前記化合物(A)100質量部に対して、遷移金属量として0.001〜10質量部含む、請求項1〜6のいずれか一項に記載の酸素吸収剤組成物。
- 請求項1〜7のいずれか一項に記載の酸素吸収剤組成物と、
前記酸素吸収剤組成物を包装する通気性包装材料と、
を備える、酸素吸収剤包装体。
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CN104582831A (zh) | 2015-04-29 |
CN104582831B (zh) | 2017-07-14 |
US20150232251A1 (en) | 2015-08-20 |
TWI584875B (zh) | 2017-06-01 |
JPWO2014034800A1 (ja) | 2016-08-08 |
EP2891519A4 (en) | 2016-06-15 |
EP2891519A1 (en) | 2015-07-08 |
US9868579B2 (en) | 2018-01-16 |
KR20150046297A (ko) | 2015-04-29 |
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