JPH07258526A - Composition and method for packaging water-containing food - Google Patents

Composition and method for packaging water-containing food

Info

Publication number
JPH07258526A
JPH07258526A JP3511795A JP3511795A JPH07258526A JP H07258526 A JPH07258526 A JP H07258526A JP 3511795 A JP3511795 A JP 3511795A JP 3511795 A JP3511795 A JP 3511795A JP H07258526 A JPH07258526 A JP H07258526A
Authority
JP
Japan
Prior art keywords
lactic acid
composition
water
polymer
food product
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.)
Pending
Application number
JP3511795A
Other languages
Japanese (ja)
Inventor
Thomas M Ford
トマス・マイケル・フオード
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ECOLOGICAL CHEM PROD
ECOLOGICAL CHEM PROD CO
Original Assignee
ECOLOGICAL CHEM PROD
ECOLOGICAL CHEM PROD CO
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by ECOLOGICAL CHEM PROD, ECOLOGICAL CHEM PROD CO filed Critical ECOLOGICAL CHEM PROD
Publication of JPH07258526A publication Critical patent/JPH07258526A/en
Pending legal-status Critical Current

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/10—Coating with a protective layer; Compositions or apparatus therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/12—Preserving with acids; Acid fermentation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/20—Organic compounds; Microorganisms; Enzymes
    • 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
    • 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
    • A23L3/3454—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 liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3499—Organic compounds containing oxygen with doubly-bound oxygen
    • 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
    • A23L3/3454—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 liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • 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
    • B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
    • B65D65/38—Packaging materials of special type or form
    • 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
    • B65D81/18—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 providing specific environment for contents, e.g. temperature above or below ambient
    • B65D81/20—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 providing specific environment for contents, e.g. temperature above or below ambient under vacuum or superatmospheric pressure, or in a special atmosphere, e.g. of inert gas
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
    • Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Mechanical Engineering (AREA)
  • Nutrition Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

PURPOSE: To extend the shelf life of foodstuff by packaging moisture-containing foodstuff with a composition wherein a lactic acid-based compound and a liquid organic plasticizer are dispersed in a lactic acid copolymer or a mixture thereof.
CONSTITUTION: A solid solution containing (A) from 5 to 30 wt.% lactic acid- based compound chosen from a lactide, a lactic acid oligomer (wherein n is from 2 to 10) and a mixture thereof, (B) from 5 to 20 wt.% liquid organic plasticizer (e.g. diisobutyl adipate) which is recognized to be safe as an indirect additive for moisture-containing food and has an atmospheric boiling point of at least 170°C and (C) from 50 to 90 wt.% polymer with a number average molecular weight of from 3,000 to 200,000 comprising polylactic acid, a lactic acid copolymer containing 50 mol.% or more lactic acid units or a mixture thereof, is used. When using this solid solution as a self-supporting film, the number average molecular weight of the polymer is 25,000 or larger, while when the composition is used as a coating, the polymer has a low molecular weight such as 3,000.
COPYRIGHT: (C)1995,JPO

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【発明の分野】本発明は水分含有食品を包装するための
組成物及び方法に関する。詳しくは、本発明は乳酸源と
して乳酸ベースの化合物を使用して、包装の中にある食
品の保存寿命を延ばす仕方で水分含有食品を包装する方
法に関する。FIELD OF THE INVENTION The present invention relates to compositions and methods for packaging moisture-containing food products. In particular, the present invention relates to a method of packaging a moisture-containing food product in a manner that uses a lactic acid-based compound as a lactic acid source and extends the shelf life of the food product in the package.

【０００２】[0002]

【発明の背景】多くの水分含有食品生産物例えば食肉は
貯蔵の間、特にそれが凍結されていない場合、酸化によ
る芳香の悪化及び微生物の増殖を起こし易い。微生物の
増殖を抑え、それにより保存寿命を延ばすためしばしば
添加剤が食品に添加され又は食品表面にコートされる。BACKGROUND OF THE INVENTION Many water-containing food products, such as meat, are prone to oxidative aroma deterioration and microbial growth during storage, especially when it is not frozen. Additives are often added to or coated on foods to control microbial growth and thereby extend shelf life.

【０００３】乳酸は食品の添加剤として安全であること
から、微生物増殖を抑制する薬剤としてしばしば提唱さ
れてきた物質である。この目的のため乳酸は加工した低
脂肪食肉製品、家禽及び魚介製品を含む食肉における微
生物増殖を抑制するために有効であることが見出され
た。より特定すると、乳酸及びその塩がイー・コリ
（E．coli）、リステリア・モノシトゲネス（Listeria
monocytogenes）、ペニシリウム・エキスパンスム（Pen
icillium expansum）、サッカロミセス・セレビシエー
（Saccharomyces cerevisiae）、シュードモナス・フル
オレッセンス（Pseudomonas fluorescens）及びスタフ
ィロコッカス・オーレウス（Staphylococcus aureus）
の増殖を抑制する点で実質的な効果を持つことが見出さ
れた。Since lactic acid is safe as an additive for foods, lactic acid is a substance often advocated as a drug for suppressing microbial growth. To this end, lactic acid has been found to be effective in inhibiting microbial growth in meat, including processed low-fat meat products, poultry and seafood products. More specifically, lactic acid and its salts are listed in E. coli, Listeria monocytogenes (Listeria
monocytogenes), Penicillium expandus (Pen
icillium expansum), Saccharomyces cerevisiae, Pseudomonas fluorescens and Staphylococcus aureus
It has been found that it has a substantial effect in suppressing the growth of A.

【０００４】乳酸及びその誘導体は抗菌剤として詳細に
わたって評価されてきたが、これまでの所、広い範囲で
使用されるには至っていない。その理由の一部は、乳酸
をそれを含む製品にかなりの費用をかけないで用いるこ
とができる信頼性のあるそして経済的な供給システムが
なかったことによる。Lactic acid and its derivatives have been evaluated in detail as antibacterial agents, but so far they have not been used in a wide range. Part of the reason is that there was no reliable and economical supply system in which lactic acid could be used for products containing it at a reasonable cost.

【０００５】[0005]

【発明の要約】従って、本発明はその第一の態様におい
て、 ａ) ラクチド、乳酸オリゴマー、（ＬＡ)n（ｎは少なく
とも２である）及びそれらの混合物からなる群より選ば
れる乳酸ベースの化合物５〜３０重量％、 ｂ) 水分含有食品への間接的添加剤として安全であるこ
とが認められ、そして少なくとも１７０℃の大気中沸点
を持つ有機液体可塑剤５〜２０重量％、及び ｃ) ３,０００〜２００,０００の数平均分子量を持つポ
リ（乳酸）、及び少なくとも５０モル％の乳酸ユニット
を含む乳酸のコポリマー並びにそれらの混合物からなる
群より選ばれるポリマー５０〜９０重量％の均質な固溶
体からなる、実質的に水及び乳酸を含まない抗菌組成物
に関する。SUMMARY OF THE INVENTION Accordingly, the present invention in a first aspect thereof is a lactic acid-based compound selected from the group consisting of: a) lactides, lactic acid oligomers, (LA) n (n is at least 2) and mixtures thereof. 5 to 30% by weight, b) 5 to 20% by weight of an organic liquid plasticizer found to be safe as an indirect additive to water-containing foodstuffs and having an atmospheric boiling point of at least 170 ° C., and c) 3. 50% to 90% by weight of a solid solid solution of a polymer selected from the group consisting of poly (lactic acid) having a number average molecular weight of 1,000 to 200,000, and a copolymer of lactic acid containing at least 50 mol% lactic acid units, and mixtures thereof. Which is substantially free of water and lactic acid.

【０００６】第二の態様においては、本発明は少なくと
も５マイクロメートルの厚さを持つ上述の抗菌組成物の
固体層がコートされたポリマー基材からなる、それに接
触している水分含有食品の保存寿命を延ばすのに適する
包装材料に関する。In a second aspect, the invention relates to the preservation of a water-containing food product which is in contact with a polymeric substrate coated with a solid layer of the above-mentioned antimicrobial composition having a thickness of at least 5 micrometers. It relates to a packaging material suitable for extending the life.

【０００７】第三の態様においては、本発明は水分含有
食品に水の薄いコーティングを適用し、食品を上述の抗
菌組成物と接触させて包装し、そして乳酸の（加水分解
による）生成及びその水分含有食品中への拡散が行われ
るのに十分な時間、食品を包装中に保つことからなる、
食品上の細菌の増殖を抑制することによる水分含有食品
の保存寿命を延ばす方法に関する。水コーティングを代
わりに抗菌組成物の接触する側に適用してもよい。In a third aspect, the present invention applies a thin coating of water to a water-containing food product, packages the food product in contact with the antimicrobial composition described above, and produces (by hydrolysis) lactic acid and its formation. Consisting in keeping the food in the package for a sufficient time for diffusion into the water-containing food to take place,
The present invention relates to a method of extending the shelf life of a water-containing food by suppressing the growth of bacteria on the food. A water coating may instead be applied to the contacting side of the antimicrobial composition.

【０００８】[0008]

【発明の詳述】Detailed description of the invention

一般事項 本発明は、広くは水分含有食品例えば食肉をポリ（乳
酸）及びラクチド含有組成物のフィルムで包むことによ
り、フィルムが食品の湿潤表面に乳酸を供給し、食品上
の細菌増殖を抑制し、その結果、食品の保存寿命を延ば
す、水分含有食品の保存寿命を延ばす方法に関する。こ
の組成物は、ポリ（乳酸）ポリマー又はコポリマー、加
水分解して乳酸を生成することが可能な乳酸ベースの化
合物、及び組成物から食品表面への乳酸又は乳酸ベース
の化合物の拡散を容易にする少量の有機可塑剤からな
る。General The present invention broadly relates to the inclusion of a water-containing food, such as meat, with a film of a poly (lactic acid) and lactide-containing composition so that the film supplies lactic acid to the wet surface of the food and suppresses bacterial growth on the food. As a result, the present invention relates to a method for extending the shelf life of foods and extending the shelf life of water-containing foods. This composition facilitates the diffusion of lactic acid or lactic acid-based compounds from the composition to a food surface, as well as poly (lactic acid) polymers or copolymers, lactic acid-based compounds that can be hydrolyzed to produce lactic acid. It consists of a small amount of organic plasticizer.

【０００９】乳酸ポリマー 本発明の使用に適するポリマーは、３,０００〜２０,０
００の数平均分子量を持つポリ（乳酸）ホモポリマー及
び少なくとも５０モル％の乳酸ユニットを含むコポリマ
ー並びにそれらの混合物である。ラクチド及び／又はオ
リゴマーの移動度を過度に高く制限しないようにポリマ
ーの分子量は１００,０００を超えないのが好ましい。Lactic acid polymers Polymers suitable for use in the present invention range from 3,000 to 20,0.
Poly (lactic acid) homopolymers having a number average molecular weight of 00 and copolymers containing at least 50 mol% lactic acid units and mixtures thereof. The molecular weight of the polymer preferably does not exceed 100,000 so as not to limit the mobility of the lactide and / or the oligomer to too high.

【００１０】ポリ（乳酸）のようなポリ（ヒドロキシ）
酸は、典型的にはモノマーの環状エステル（ラクトン）
又は二量体環状エステルの接触開環重合により製造され
る。コポリマーは典型的には２つ以上の環状エステル及
び／又は二量体環状エステルの接触重合により製造され
る。典型的なコモノマーはグリコリド（１,４−ジオキ
サン−２,５−ジオン）、グリコール酸の二量体環状エ
ステル；乳酸の二量体環状エステル；β−プロピオラク
トン、３−ヒドロキシプロパン酸の環状エステル；α,
α−ジメチル−β−プロピオラクトン、２,２−ジメチ
ル−３−ヒドロキシプロパン酸の環状エステル；β−ブ
チロラクトン、３−ヒドロキシ酪酸の環状エステル；δ
−バレロラクトン、５−ヒドロキシペンタン酸の環状エ
ステル；ε−カプロラクトン、６−ヒドロキシヘキサン
酸の環状エステル、及びそのメチル置換誘導体、例えば
２−メチル−６−ヒドロキシヘキサン酸、３−メチル−
６−ヒドロキシヘキサン酸、４−メチル−６−ヒドロキ
シヘキサン酸、３,３,５−トリメチル−６−ヒドロキシ
ヘキサン酸などのラクトン類；ドデカラクトン、２−
（２−ヒドロキシエチル）−グリコール酸の環状エステ
ルである。Poly (hydroxy) such as poly (lactic acid)
Acids are typically cyclic esters (lactones) of monomers
Alternatively, it is produced by catalytic ring-opening polymerization of a dimeric cyclic ester. Copolymers are typically made by catalytic polymerization of two or more cyclic esters and / or dimeric cyclic esters. Typical comonomers are glycolide (1,4-dioxane-2,5-dione), dimeric cyclic ester of glycolic acid; dimeric cyclic ester of lactic acid; β-propiolactone, cyclic of 3-hydroxypropanoic acid Ester; α,
α-Dimethyl-β-propiolactone, cyclic ester of 2,2-dimethyl-3-hydroxypropanoic acid; β-butyrolactone, cyclic ester of 3-hydroxybutyric acid; δ
Valerolactone, a cyclic ester of 5-hydroxypentanoic acid; ε-caprolactone, a cyclic ester of 6-hydroxyhexanoic acid, and its methyl-substituted derivatives such as 2-methyl-6-hydroxyhexanoic acid, 3-methyl-
Lactones such as 6-hydroxyhexanoic acid, 4-methyl-6-hydroxyhexanoic acid, 3,3,5-trimethyl-6-hydroxyhexanoic acid; dodecalactone, 2-
It is a cyclic ester of (2-hydroxyethyl) -glycolic acid.

【００１１】その製造方法のために、ポリ（乳酸）は時
にはポリ（ラクチド）と称する。本明細書で使用する用
語「ポリ乳酸」及び「ポリラクチド」は相互に置き換え
ることが可能である。ラクチドは（１）乳酸を重合させ
てオリゴマー、すなわち比較的低分子のポリ（乳酸）を
生成させ；（２）一般に触媒の存在下でオリゴマーを加
熱してラクチドに解重合させ；そして（３）ラクチドを
回収し精製することより製造される。例えば、Lowe, 米
国特許2,668,162；Bhatia, 米国特許4,835,293及び5,02
3,349；DeVries, 米国特許4,797,468；及びMuller, 米
国特許5,053,522が参照される。ラクチドは４つの形
態；Ｄ,Ｄ体としても知られるＤ体；Ｌ,Ｌ体としても知
られるＬ体；Ｄ,Ｌ体；及びメソ体のいずれかで存在す
ることができる。Because of its method of manufacture, poly (lactic acid) is sometimes referred to as poly (lactide). The terms "polylactic acid" and "polylactide" used herein are interchangeable. Lactide (1) polymerizes lactic acid to form an oligomer, that is, a relatively low molecular weight poly (lactic acid); (2) generally heats the oligomer in the presence of a catalyst to depolymerize it to lactide; and (3) It is produced by recovering and purifying lactide. For example, Lowe, U.S. Patent 2,668,162; Bhatia, U.S. Patents 4,835,293 and 5,02.
3,349; DeVries, U.S. Patent 4,797,468; and Muller, U.S. Patent 5,053,522. Lactide can exist in any of four forms; the D form, also known as the D, D form; the L form, also known as the L, L form; the D, L form; and the meso form.

【００１２】スズ化合物により触媒される環状エステル
及び二量体環状エステルの重合は、Young, 米国特許2,8
90,208；Blood, 米国特許3,645,941；及びVersfelt, 米
国特許3,839,297に開示されている。２−エチルヘキサ
ン酸スズ（II）（オクタン酸スズ）及びスズ（II）の炭
素原子１８までのカルボン酸とその他エステル並びにテ
トラフェニルスズのようなスズ化合物はよく知られたラ
クチド重合触媒である。酸化スズを使用する重合はH.
R. Kricheldorf及びA. Serra, Polymer Bulletin, 14
巻, 497〜502ページ, 1985年に記述されている。２−エ
チルヘキサン酸スズ（II）を使用するラクチドの重合は
J. W. Leenslag及びA. J. Pennings, Makromol. Chem.
188巻, 1809〜1814ページ（1987年）に記述されてい
る。典型的には約０.０１〜１重量％のスズ触媒を使用
する。Polymerization of cyclic and dimeric cyclic esters catalyzed by tin compounds is described in Young, US Pat.
90,208; Blood, U.S. Patent 3,645,941; and Versfelt, U.S. Patent 3,839,297. Tin (II) 2-ethylhexanoate (tin octoate) and carboxylic acids of tin (II) up to 18 carbon atoms and other esters and tin compounds such as tetraphenyltin are well known lactide polymerization catalysts. Polymerization using tin oxide is H.
R. Kricheldorf and A. Serra, Polymer Bulletin, 14
Volume, pp. 497-502, 1985. Polymerization of lactide using tin (II) 2-ethylhexanoate
JW Leenslag and AJ Pennings, Makromol. Chem.
188, pp. 1809-1814 (1987). Typically about 0.01 to 1 wt% tin catalyst is used.

【００１３】イットリウム化合物及び希土類化合物によ
る重合も記述されている。イットリウム・トリス（メチ
ル−Ｓ−ラクテート）及びサマリウム・トリス（２−
Ｎ,Ｎ−ジメチルアミノエトキシド）のような触媒を使
用するラクチドの重合はMcLain, 米国特許5,028,667に
記述されている。ランタン・ビス（２,２,６,６−テト
ラメチルヘプタン−３,５−ジオナト）−ｉ−プロポキ
シドを使用するラクチドの重合はFord, 米国特許5,208,
297に記述されている。Polymerization with yttrium and rare earth compounds has also been described. Yttrium tris (methyl-S-lactate) and samarium tris (2-
Polymerization of lactide using a catalyst such as N, N-dimethylaminoethoxide) is described in McLain, US Pat. No. 5,028,667. Polymerization of lactide using lanthanum bis (2,2,6,6-tetramethylheptane-3,5-dionato) -i-propoxide is described in Ford, US Pat.
297.

【００１４】エーテル錯体例えばランタン・トリス
（２,２,６,６−テトラメチルヘプタンジオネート）・
ジエチレングリコールジエチルエーテル錯体を使用する
ラクチドの重合はFord, ＰＣＴ出願 PCT／US92／11309
に記述されている。Ether complexes such as lanthanum tris (2,2,6,6-tetramethylheptanedionate).
Polymerization of lactide using diethylene glycol diethyl ether complex is Ford, PCT application PCT / US92 / 11309
It is described in.

【００１５】乳酸のコポリマーを本発明に使用する場
合、それらは少なくとも５０モル％の乳酸ユニットを含
むのが好ましい。そのようなコポリマーは少なくとも７
０モル％の乳酸ユニットを含むのがより一層好ましい。When copolymers of lactic acid are used in the present invention, they preferably contain at least 50 mol% lactic acid units. At least 7 such copolymers
It is even more preferred to contain 0 mol% lactic acid units.

【００１６】本発明の組成物が基材を使用しない自己支
持性フィルムとして適用される場合は、ポリマーの数平
均分子量（ゲル透過クロマトグラフィーにより測定）が
少なくとも２５,０００であるのが好ましい。一方、組
成物を基材例えば板紙、ポリエステル又はポリ塩化（ビ
ニリデン）に適用する場合、コーティングは３,０００
のような低い分子量でよい。When the composition of the present invention is applied as a substrate-free self-supporting film, it is preferred that the polymer have a number average molecular weight (measured by gel permeation chromatography) of at least 25,000. On the other hand, if the composition is applied to a substrate such as paperboard, polyester or poly (vinylidene) chloride, the coating is 3,000.
A low molecular weight such as

【００１７】組成物を基材に適用して本発明の包装材料
を製造する場合、耐酸素性又は耐湿性のいずれか、そし
て好ましくは両方に耐性であるポリマー材料を使用する
のが好ましい。適当な基材はコートした板紙、ポリエス
テル、ポリ（塩化ビニリデン）、エチレン−ビニルアル
コールコポリマーなどを含む。ポリオレフィンは本発明
の組成物のための基材として使用することができるが、
それらは酸素を十分に排除しない。When the composition is applied to a substrate to make the packaging material of the present invention, it is preferred to use polymeric materials that are resistant to either oxygen or moisture resistance, and preferably both. Suitable substrates include coated paperboard, polyester, poly (vinylidene chloride), ethylene-vinyl alcohol copolymer and the like. Polyolefins can be used as substrates for the compositions of the present invention,
They do not remove oxygen well.

【００１８】乳酸ベースの化合物 本発明の使用に適する乳酸ベースの化合物は加水分解し
て液体乳酸を生成し、ポリマーマトリックスを通過して
水分含有食品例えば生食肉の表面に拡散できるものでな
ければならない。特に好適な化合物はラクチド及び乳酸
の低分子オリゴマー、すなわちモノマーユニットの平均
の数（ｎ）が少なくとも２であり、例えばｎは２〜１０
であるオリゴマーである。上記で検討したように、その
ようなオリゴマーは通常乳酸の脱水により製造され、そ
してラクチドは通常オリゴマーの熱分解により相当する
環状ジエステル（ラクチド）を生成させることにより製
造される。そのため、ｎが２よりもっと大きいオリゴマ
ーを使用するのが好ましく、これらは水を多く含まない
からである。包装材料の加水分解性成分としてはラクチ
ドを使用するのが好ましく、それはこの物質がより容易
に加水分解し、従って所定の濃度水準においてより有効
であることによる。それでもなお、低分子乳酸オリゴマ
ー及びその乳酸との混合物は適切に組成を変えて使用す
ることができる。Lactic Acid-Based Compounds Lactic acid-based compounds suitable for use in the present invention must be capable of hydrolyzing to produce liquid lactic acid and diffusing through the polymer matrix to the surface of moisture-containing food products such as raw meat. . Particularly preferred compounds are low molecular weight oligomers of lactide and lactic acid, i.e. the average number (n) of monomer units is at least 2, e.g.
Is an oligomer. As discussed above, such oligomers are usually prepared by dehydration of lactic acid, and lactides are usually prepared by thermal decomposition of the oligomers to form the corresponding cyclic diesters (lactides). Therefore, it is preferable to use oligomers in which n is greater than 2, as these do not contain much water. It is preferred to use lactide as the hydrolyzable component of the packaging material, since this substance hydrolyzes more easily and is therefore more effective at the given concentration level. Nevertheless, the low-molecular-weight lactic acid oligomer and its mixture with lactic acid can be used by appropriately changing the composition.

【００１９】可塑剤 本発明における使用に適する可塑剤は常温で液体であ
り、少なくとも１７０℃の大気中沸点を持ち、水分含有
食品に対する間接的食品添加剤としての使用が認められ
ているものである。そのような物質は合衆国食品医薬品
局により法律３７ＣＦＲ２１のセクション１７５.３０
０及び１８１.２７に記載された可塑剤、すなわちクエ
ン酸アセチルトリブチル、クエン酸アセチルトリエチ
ル、サリチル酸ｐ−第三ブチルフェニル、ステアリン酸
ブチル、ブチルグリコール酸ブチルフタリル、ステアリ
ン酸ブチル、セバチン酸ジブチル、フタル酸ジ−（２−
エチルヘキシル）、フタル酸ジエチル、アジピン酸ジイ
ソブチル、フタル酸ジイソオクチル、リン酸ジフェニル
−２−エチルヘキシル、エポキシド化大豆油、エチルグ
リコール酸エチルフタリル、グリセロール、グリセリル
モノオレエート、グリセリルトリアセテート、クエン酸
モノイソプロピル、クエン酸モノ、ジ及びトリステアリ
ル、プロピレングリコール、ソルビトール、トリアセチ
ン（グリセロールトリアセテート）、クエン酸トリエチ
ル及びトリエチレングリコールを含む。Plasticizers Plasticizers suitable for use in the present invention are liquid at room temperature, have an atmospheric boiling point of at least 170 ° C., and are approved for use as indirect food additives for water-containing foods. . Such substances are classified by the US Food and Drug Administration in section 175.30 of Act 37CFR21.
0 and 181.27, namely acetyltributyl citrate, acetyltriethyl citrate, p-tert-butylphenyl salicylate, butyl stearate, butylphthalyl butylglycolate, butyl stearate, dibutyl sebacate, phthalic acid. Di- (2-
Ethylhexyl), diethyl phthalate, diisobutyl adipate, diisooctyl phthalate, diphenyl-2-ethylhexyl phosphate, epoxidized soybean oil, ethylphthalyl ethyl glycolate, glycerol, glyceryl monooleate, glyceryl triacetate, monoisopropyl citrate, citric acid Includes mono, di and tristearyl, propylene glycol, sorbitol, triacetin (glycerol triacetate), triethyl citrate and triethylene glycol.

【００２０】乳酸又は乳酸前駆物質が抗菌的有効性を示
すに十分な量で食品表面への適切な拡散を得るために
は、組成物中に少なくとも５重量％の可塑剤を必要とす
る。一方、フィルムの物理的性質が損なわれないように
するためには、約２０重量％以下の可塑剤を使用すべき
である。最適な結果を得るには、可塑剤が８〜１５重量
％の量存在するのが好ましい。しかしながら、最適量は
ラクチドポリマー、乳酸ベースの化合物及び可塑剤の物
理的性質により大きく変動し得ることが認められるであ
ろう。可塑剤はポリマー巾で均質に分散しなければなら
ないので、室温でポリマーの存在下で結晶してはならな
い。それにもかかわらず、ポリマー加工の間の過度の蒸
発損失を防ぐため、可塑剤の大気中沸点は好ましくは約
１７０℃を超えるがもっと高くてもよい。従って、可塑
剤の沸点は少なくとも２００℃又はそれ以上であるのが
いっそう好ましい。可塑剤の分解温度はもちろん、ポリ
マーの最高の加工温度より高くなければならない。In order for the lactic acid or lactic acid precursor to obtain adequate diffusion to the food surface in an amount sufficient to exhibit antimicrobial efficacy, at least 5% by weight of the plasticizer in the composition is required. On the other hand, no more than about 20% by weight of plasticizer should be used so that the physical properties of the film are not compromised. For optimum results, it is preferred that the plasticizer be present in an amount of 8-15% by weight. However, it will be appreciated that the optimum amount can vary widely depending on the physical properties of the lactide polymer, the lactic acid based compound and the plasticizer. The plasticizer must disperse homogeneously in the polymer width and therefore should not crystallize in the presence of the polymer at room temperature. Nevertheless, the atmospheric boiling point of the plasticizer is preferably above about 170 ° C., but may be higher, to prevent excessive evaporation loss during polymer processing. Therefore, it is more preferred that the boiling point of the plasticizer is at least 200 ° C or higher. The decomposition temperature of the plasticizer must, of course, be above the maximum processing temperature of the polymer.

【００２１】配合 本発明の組成物はポリマーを溶融し、そして無水条件下
で液体可塑剤及び加水分解性乳酸ベースの化合物に混合
することにより容易に製造することができる。組成物及
び成分は実質的に乾燥していることが肝要であり、なぜ
なら少しでも水が存在すると乳酸前駆物質（ラクチド）
の早期加水分解が起こり、そして乳酸ポリマーの加水分
解も同様に起こることがあるからである。成分は実質的
に可溶性であり、従って低いエネルギー入力で均質に混
合することが容易である。ポリ（乳酸）は周辺大気中に
置くと空気中の水分を吸収することができ、これが次に
ラクチド又はポリマーの加水分解により乳酸を生成す
る。従って、早期ラクチドの加水分解を防ぐことが好ま
しい。この理由から、組成物は１重量％以下の水又は乳
酸を含むべきである。この組成物は、０.０１％以下の
水及び０.１％以下の乳酸を含むのがよりいっそう好ま
しい。Formulation The composition of the present invention can be readily prepared by melting the polymer and mixing under anhydrous conditions with the liquid plasticizer and the hydrolyzable lactic acid based compound. It is essential that the composition and ingredients be substantially dry because lactic acid precursor (lactide) is present in the presence of any water.
Because premature hydrolysis of the lactic acid polymer can occur and hydrolysis of the lactic acid polymer can occur as well. The components are substantially soluble and therefore easy to mix homogeneously with low energy input. When placed in ambient air, poly (lactic acid) can absorb moisture in the air, which in turn produces lactic acid by hydrolysis of the lactide or polymer. Therefore, it is preferable to prevent early hydrolysis of lactide. For this reason, the composition should contain no more than 1% by weight of water or lactic acid. Even more preferably, the composition comprises 0.01% or less water and 0.1% or less lactic acid.

【００２２】適用 上述の抗菌組成物は室温で固体であるが、保護する食品
生産物に対して種々の方法で適用することができる。そ
れは食品を包むための自己支持性フィルムに成形するこ
とができる。それは適当なポリマー基材、例えば板紙、
ポリエステル又はポリオレフィンにコートし、次にこれ
を包装紙として使用するか又は食品用コンテナーに成形
することもできる。適用方法の如何にかかわらず、食品
に接触する組成物の層は厚さが少なくとも５マイクロメ
ートル（０.２ミル）そして好ましくは１０マイクロメ
ートル（０.４ミル）以上である。コーティングの厚さ
は通常組成物の物理的性質及び乳酸ベースの化合物の配
合されたコーティングから食品表面への拡散性を考慮し
て調節することができる。より厚い層を使用することが
できるが、約５０マイクロメートル（２ミル）を超える
フィルムの厚さにしても得られる利点はほとんどない。
ラクチド又はオリゴマーの拡散作用を容易にするため、
水分含有食品はフィルムコーティングを適用するか又は
食品を本発明の組成物の容器に入れる前、水の薄層をコ
ートするのが好ましい。別法として、フィルムを食品に
適用する前又は食品を本発明の組成物の容器に入れる
前、フィルムに水の薄い塗膜を適用することにより同じ
結果を得ることができる。Application Although the antimicrobial composition described above is solid at room temperature, it can be applied in various ways to the food product it protects. It can be formed into a self-supporting film for wrapping food products. It is a suitable polymer substrate such as paperboard,
It is also possible to coat polyester or polyolefin which is then used as wrapping paper or molded into food containers. Regardless of the method of application, the layer of food contact composition is at least 5 micrometers (0.2 mils) and preferably 10 micrometers (0.4 mils) or more. The thickness of the coating can usually be adjusted taking into account the physical properties of the composition and the diffusivity of the lactic acid-based compound from the compounded coating to the food surface. Thicker layers can be used, but there is little benefit obtained with film thicknesses greater than about 50 micrometers (2 mils).
In order to facilitate the diffusion action of lactide or oligomer,
Moisture-containing foods are preferably coated with a film coating or coated with a thin layer of water prior to placing the food in a container of the composition of the invention. Alternatively, the same result can be obtained by applying a thin coat of water to the film before applying the film to the food product or before placing the food product in a container of the composition of the present invention.

【００２３】[0023]

【実施例】【Example】

実施例１〜４ 乳酸源を供給する本発明の組成物の有効性を、種々のポ
リラクチド組成物を一塩基性リン酸カリウムの水溶液に
浸漬して、浸出させて測定する一連の４回の実験を行っ
た。詳しく説明すると、各組の試料を０.６ｇの小片に
切断し、栓をほどこした小さなガラス瓶の中の６mlの
０.２Ｍの一塩基性リン酸カリウムの中に入れた。各溶
液のpHを２ＮのＮａＯＨで調節した。各試料からの浸出
液を含む液体の試料を１週間間隔で７週間にわたって採
取し、その中の乳酸の量を逆相高速液体クロマトグラフ
ィーにより測定した。これらのデータを時間の関数とし
てプロットした。その結果を図１〜７に示す。試験した
材料の組成及び試験条件を下の表１及び２に示す。Examples 1 to 4 A series of four experiments was conducted to determine the efficacy of compositions of the present invention supplying a lactic acid source by leaching various polylactide compositions in an aqueous solution of potassium phosphate monobasic and leaching. I went. In detail, each set of samples was cut into 0.6 g pieces and placed in 6 ml of 0.2 M monobasic potassium phosphate in a small, capped glass bottle. The pH of each solution was adjusted with 2N NaOH. Liquid samples containing leachate from each sample were taken at weekly intervals for 7 weeks and the amount of lactic acid therein was measured by reverse phase high performance liquid chromatography. These data were plotted as a function of time. The results are shown in FIGS. The composition of the materials tested and the test conditions are shown in Tables 1 and 2 below.

【００２４】[0024]

【表１】 [Table 1]

【００２５】[0025]

【表２】 [Table 2]

【００２６】図１は可塑剤を含まないＰＬＡ／ラクチド
組成物(Ｘ)が実施例１の条件下ではほとんど乳酸を生成
しないことを示している。一方、可塑剤を含む組成物
（Ｙ及びＺ）は７週間の試験期間を通じてかなりの乳酸
の浸出を示している。同様に、図２は可塑剤を含まない
組成物(Ｘ)が実施例２のより高いpH条件下でもほとんど
乳酸を生成しないことを示している。再び、可塑剤を含
む組成物（Ｙ及びＺ）は７週間の試験期間を通じてかな
りの浸出を示している。しかしながら、実施例３及び４
のより高温の条件においては図３及び４に示すように、
いくらかの乳酸の浸出が可塑剤を含まない材料(Ｘ)であ
ったことを示している。しかしながら、その量は可塑剤
を含む材料（Ｙ及びＺ）からの量より著しく少ない。FIG. 1 shows that the plasticizer-free PLA / lactide composition (X) produces little lactic acid under the conditions of Example 1. On the other hand, the compositions containing plasticizers (Y and Z) show significant lactic acid leaching throughout the 7 week test period. Similarly, FIG. 2 shows that the composition without plasticizer (X) produces little lactic acid even under the higher pH conditions of Example 2. Again, the plasticizer containing compositions (Y and Z) show significant leaching throughout the 7 week test period. However, Examples 3 and 4
As shown in FIGS. 3 and 4, in the higher temperature condition of
It shows that some lactic acid leaching was material (X) without plasticizer. However, its amount is significantly less than that from the plasticizer containing materials (Y and Z).

【００２７】図５は実施例１及び２の条件下で可塑剤を
含まない組成物(Ｘ)からの乳酸の抽出が無視し得ること
をグラフで示している。一方、実施例３及び４の高温条
件下では著しい量の抽出が起こっている。図６及び７は
可塑剤を含む組成物がすべての試験条件（実施例１〜
４）で乳酸放出の点で有効であったことを示している。FIG. 5 graphically shows that under the conditions of Examples 1 and 2, the extraction of lactic acid from the plasticizer-free composition (X) is negligible. On the other hand, a significant amount of extraction occurs under the high temperature conditions of Examples 3 and 4. 6 and 7 show that the composition containing the plasticizer was tested under all test conditions (Examples 1 to 1).
4) shows that it was effective in terms of lactic acid release.

【００２８】要約すると、これらのデータはポリマー／
ラクチド組成物が追加の可塑剤を含まない場合乳酸の生
成と移動は極めて少ないことを示している。一方可塑剤
が存在すると、極めて著しい量の乳酸の生成と周辺液体
への移動が起こる。すべての場合で高い温度とpHにより
周囲の液体中に生成する乳酸の量は増加する。その上、
すべてのpH及び温度水準において、より高分子のポリマ
ー（４０,０００対２０,０００）の使用は周辺液体にお
けるより高い乳酸量を与える。In summary, these data are polymer /
It shows that lactic acid production and migration is very low when the lactide composition contains no additional plasticizer. On the other hand, the presence of the plasticizer causes the production of a very significant amount of lactic acid and its transfer to the surrounding liquid. In all cases, elevated temperature and pH increase the amount of lactic acid produced in the surrounding liquid. Moreover,
At all pH and temperature levels, the use of higher polymer (40,000 vs. 20,000) gives higher lactic acid content in the surrounding liquid.

【図面の簡単な説明】[Brief description of drawings]

【図１】試験条件１（pH＝５.３、温度＝３５°Ｆ）に
おける各試料Ｘ、Ｙ及びＺからの乳酸の抽出濃度対抽出
時間曲線を示す図である。FIG. 1 is a diagram showing an extraction concentration versus extraction time curve of lactic acid from each sample X, Y and Z under test condition 1 (pH = 5.3, temperature = 35 ° F.).

【図２】試験条件２（pH＝６.５、温度＝３５°Ｆ）に
おける各試料Ｘ、Ｙ及びＺからの乳酸の抽出濃度対抽出
時間曲線を示す図である。FIG. 2 is a diagram showing an extraction concentration vs. extraction time curve of lactic acid from each sample X, Y and Z under test condition 2 (pH = 6.5, temperature = 35 ° F.).

【図３】試験条件３（pH＝５.３、温度＝５０°Ｆ）に
おける各試料Ｘ、Ｙ及びＺからの乳酸の抽出濃度対抽出
時間曲線を示す図である。FIG. 3 is a diagram showing an extraction concentration-extraction time curve of lactic acid from each sample X, Y and Z under test condition 3 (pH = 5.3, temperature = 50 ° F.).

【図４】試験条件４（pH＝６.５、温度＝５０°Ｆ）に
おける各試料Ｘ、Ｙ及びＺからの乳酸の抽出濃度対抽出
時間曲線を示す図である。FIG. 4 is a diagram showing an extraction concentration versus extraction time curve of lactic acid from each sample X, Y and Z under test condition 4 (pH = 6.5, temperature = 50 ° F.).

【図５】各試験条件（１、２、３及び４）における試料
Ｘからの乳酸の抽出濃度対抽出時間曲線を示す図であ
る。FIG. 5 is a diagram showing an extraction concentration vs. extraction time curve of lactic acid from Sample X under each test condition (1, 2, 3 and 4).

【図６】各試験条件（１、２、３及び４）における試料
Ｙからの乳酸の抽出濃度対抽出時間曲線を示す図であ
る。FIG. 6 is a diagram showing an extraction concentration vs. extraction time curve of lactic acid from Sample Y under each test condition (1, 2, 3 and 4).

【図７】各試験条件（１、２、３及び４）における試料
Ｚからの乳酸の抽出濃度対抽出時間曲線を示す図であ
る。FIG. 7 is a diagram showing an extraction concentration vs. extraction time curve of lactic acid from Sample Z under each test condition (1, 2, 3 and 4).

Claims (10)

【特許請求の範囲】[Claims] 【請求項１】 ａ) ラクチド、乳酸オリゴマー、（Ｌ
Ａ)n（ｎ＝２〜１０）及びそれらの混合物からなる群よ
り選ばれる乳酸ベースの化合物５〜３０重量％、及び ｂ) 水分含有食品への間接的添加剤として安全であるこ
とが認められている有機液体可塑剤５〜２０重量％を含
み、成分ａ)及びｂ)はいずれも ｃ) ３,０００〜２００,０００の数平均分子量を持つポ
リ（乳酸）、少なくとも５０モル％の乳酸ユニットを含
む乳酸のコポリマー及びそれらの混合物からなる群より
選ばれる５０〜９０重量％の固体ポリマーの固体マトリ
ックス中に分散させた均質な固溶体からなる、実質的に
水及び乳酸を含まない抗菌組成物。1. A) lactide, lactic acid oligomer, (L
A) 5 to 30% by weight of a lactic acid-based compound selected from the group consisting of n (n = 2 to 10) and mixtures thereof, and b) recognized as safe as an indirect additive to water-containing foods. 5 to 20% by weight of the organic liquid plasticizer, and the components a) and b) are both c) poly (lactic acid) having a number average molecular weight of 3,000 to 200,000, at least 50 mol% of lactic acid units. A substantially water- and lactic acid-free antibacterial composition consisting of a homogeneous solid solution dispersed in a solid matrix of 50-90% by weight of a solid polymer selected from the group consisting of copolymers of lactic acid containing and a mixture thereof. 【請求項２】 可塑剤がアジピン酸ジイソブチルである
請求項１記載の組成物。2. A composition according to claim 1, wherein the plasticizer is diisobutyl adipate. 【請求項３】 ポリマーが３,０００〜２００,０００の
分子量を持ち、基材コーティング用に特に適合させた請
求項１記載の組成物。3. A composition according to claim 1, wherein the polymer has a molecular weight of 3,000 to 200,000 and is particularly adapted for substrate coatings. 【請求項４】 ポリマーが３,０００〜２００,０００の
分子量を持ち、自己支持性フィルム形成用に特に適合さ
せた請求項１記載の組成物。4. A composition according to claim 1, wherein the polymer has a molecular weight of 3,000 to 200,000 and is particularly adapted for self-supporting film formation. 【請求項５】 少なくとも５マイクロメートルの厚さを
持つ請求項３記載の組成物の固体層がコートされたポリ
マー基材からなる、それに接触している水分含有食品の
保存寿命を延ばすのに適する包装材料。5. A solid layer of the composition of claim 3 having a thickness of at least 5 micrometers, which is suitable for extending the shelf life of a water-containing food product in contact therewith comprising a coated polymeric substrate. Packaging material. 【請求項６】 基材が板紙である請求項５記載の包装材
料。6. The packaging material according to claim 5, wherein the base material is paperboard. 【請求項７】 少なくとも５マイクロメートルの厚さを
持つ請求項４記載の組成物の軟質フィルムからなる、そ
れに接触している水分含有食品の保存寿命を延ばすのに
適する包装材料。7. A packaging material comprising a soft film of the composition of claim 4 having a thickness of at least 5 micrometers and suitable for extending the shelf life of a water-containing food product in contact therewith. 【請求項８】 請求項１記載の組成物と接触させて水分
含有食品を包装し、そして食品中の水分との接触により
乳酸ベースの化合物を加水分解するに十分な時間食品を
包装中に保持し、乳酸を生成させそして乳酸を水分含有
食品中に拡散させることからなる、食品中の細菌増殖を
抑制して水分含有食品の保存寿命を延ばす方法。8. A moisture-containing food product is packaged by contacting it with the composition of claim 1 and holding the food product in the package for a time sufficient to hydrolyze the lactic acid-based compound by contacting the moisture in the food product. Then, lactic acid is produced and the lactic acid is diffused in the water-containing food, thereby suppressing bacterial growth in the food and extending the shelf life of the water-containing food. 【請求項９】 食品を組成物の適用前に水の薄層でコー
トする請求項８記載の方法。9. The method of claim 8 wherein the food product is coated with a thin layer of water prior to application of the composition. 【請求項１０】 組成物をその適用前に水の薄層でコー
トする請求項８記載の方法。10. The method of claim 8 wherein the composition is coated with a thin layer of water prior to its application.
JP3511795A 1994-02-24 1995-02-23 Composition and method for packaging water-containing food Pending JPH07258526A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US20149694A 1994-02-24 1994-02-24
US201496 1994-02-24

Publications (1)

Publication Number Publication Date
JPH07258526A true JPH07258526A (en) 1995-10-09

Family

ID=22746051

Family Applications (1)

Application Number Title Priority Date Filing Date
JP3511795A Pending JPH07258526A (en) 1994-02-24 1995-02-23 Composition and method for packaging water-containing food

Country Status (3)

Country Link
JP (1) JPH07258526A (en)
DE (1) DE19506395A1 (en)
GB (1) GB9503669D0 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006515175A (en) * 2002-12-20 2006-05-25 プラク・ビオヘム・ベー・ブイ Controlled acidification of foods using lactic acid or glycolic acid oligomers / derivatives
JP2010512408A (en) * 2006-12-11 2010-04-22 スリーエム イノベイティブ プロパティズ カンパニー Biocompatible antimicrobial composition
JP2010150239A (en) * 2008-11-18 2010-07-08 Koken Ltd Antimicrobial composition, and method for producing the same and utilization thereof
JP2011105817A (en) * 2009-11-14 2011-06-02 Kitakyushu Foundation For The Advancement Of Industry Science & Technology Lactic acid oligomer and molded product of the same
JP2014012675A (en) * 2007-03-30 2014-01-23 Laccure Ab Use of oligomer of lactic acid in treatment of gynecological disorder
CN109486121A (en) * 2018-09-30 2019-03-19 江苏宏远新材料科技有限公司 A kind of preparation method of transparent antibacterial polyester film

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5639466A (en) * 1994-02-24 1997-06-17 Chronopol, Inc. Method for packaging foodstuffs
JP3517855B2 (en) * 1995-10-03 2004-04-12 トヨタ自動車株式会社 Polylactic acid based resin composition
EP1260453B1 (en) * 2000-01-06 2009-09-02 Yamanaka Industry Co., Ltd. Antibacterial/biodegradable extraction vessel
GB0414333D0 (en) 2004-06-25 2004-07-28 Dupont Teijin Films Us Ltd Polymeric film

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006515175A (en) * 2002-12-20 2006-05-25 プラク・ビオヘム・ベー・ブイ Controlled acidification of foods using lactic acid or glycolic acid oligomers / derivatives
JP2010512408A (en) * 2006-12-11 2010-04-22 スリーエム イノベイティブ プロパティズ カンパニー Biocompatible antimicrobial composition
JP2014012675A (en) * 2007-03-30 2014-01-23 Laccure Ab Use of oligomer of lactic acid in treatment of gynecological disorder
US8912232B2 (en) 2007-03-30 2014-12-16 Laccure Ab Use of oligomers of lactic acid in the treatment of gynaecological disorders
JP2010150239A (en) * 2008-11-18 2010-07-08 Koken Ltd Antimicrobial composition, and method for producing the same and utilization thereof
US8349346B2 (en) 2008-11-18 2013-01-08 Koken Ltd. Antimicrobial composition, process for preparing the same, and utilization thereof
JP2011105817A (en) * 2009-11-14 2011-06-02 Kitakyushu Foundation For The Advancement Of Industry Science & Technology Lactic acid oligomer and molded product of the same
CN109486121A (en) * 2018-09-30 2019-03-19 江苏宏远新材料科技有限公司 A kind of preparation method of transparent antibacterial polyester film

Also Published As

Publication number Publication date
DE19506395A1 (en) 1995-08-31
GB9503669D0 (en) 1995-04-12

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