WO2004101668A2 - Composition thermoplastique contenant un materiau liberant un inhibiteur de reponse ethylene - Google Patents

Composition thermoplastique contenant un materiau liberant un inhibiteur de reponse ethylene Download PDF

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Publication number
WO2004101668A2
WO2004101668A2 PCT/US2004/014611 US2004014611W WO2004101668A2 WO 2004101668 A2 WO2004101668 A2 WO 2004101668A2 US 2004014611 W US2004014611 W US 2004014611W WO 2004101668 A2 WO2004101668 A2 WO 2004101668A2
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WO
WIPO (PCT)
Prior art keywords
ethylene response
inhibitor releasing
response inhibitor
composition
ethylene
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.)
Ceased
Application number
PCT/US2004/014611
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English (en)
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WO2004101668A3 (fr
Inventor
Jonathan R. Freedman
William Spano
Ihab M. Hekal
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CSP Technologies Inc
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CSP Technologies Inc
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Publication date
Application filed by CSP Technologies Inc filed Critical CSP Technologies Inc
Publication of WO2004101668A2 publication Critical patent/WO2004101668A2/fr
Publication of WO2004101668A3 publication Critical patent/WO2004101668A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds

Definitions

  • the present invention relates to an ethylene response inhibitor releasing composition
  • an ethylene response inhibitor releasing composition comprising a combination of an ethylene response inhibitor releasing material that is incorporated within a thermoplastic.
  • the ethylene response inhibitor releasing material reacts to release a gas, which is composed of an ethylene response inhibitor compound, through the thermoplastic into the surrounding environment.
  • thermoplastic materials include, but are not limited to, polyolefins such as polypropylene and polyethylene (linear low density), polycarbonates, polyamides, ethylene- vinyl acetate copolymers, ethylene-methacrylate copolymer, polyacrylianitrile, polysulfones, polyacrylic ester, acrylic, polyurethane and polyacetal, or copolymers or mixtures thereof.
  • polyolefins such as polypropylene and polyethylene (linear low density)
  • polycarbonates such as polypropylene and polyethylene (linear low density)
  • polyamides such as polypropylene and polyethylene (linear low density)
  • ethylene- vinyl acetate copolymers such as polyethylene-methacrylate copolymer
  • polyacrylianitrile polysulfones
  • polyacrylic ester acrylic, polyurethane and polyacetal, or copolymers or mixtures thereof.
  • the desired thennoplastic is selected based on the end-use.
  • suitable ethylene response inhibitor releasing compounds include, but are not limited to, cyclopropene derivatives, 1-methylcyclopropene, and 1.1.1 propellane or derivatives therof .
  • mixtures of ethylene response inhibitor releasing compounds may be combined.
  • the ethylene response inhibiting compounds may be produced by one or more of the methods that are disclosed in U.S. Patent Nos. 5,518,988; 6,194,350; or 6,365,549, incorporated by reference herein.
  • the ethylene response inhibiting compound is selected from the group consisting of 3,3-dipentyl- cyclopropene, 1 -pent-2-enyl-2-pentyl-cyclopropene, 1 -pent-2-enyl-3 ,3 -dipentyl- cyclopropene, 4-(l-cyclopropenyl)-2-methylbutan-2-ol, l-(n-amyl)-cyclopropene, 1 -(5,5,5- trifluoropentyl)-cyclopropene, and 1,2-dipentyl-cyclopropene.
  • the ethylene response inhibitor releasing compound loading level can range from about 0.5% to about 15%, more specifically about 5% to about 10%, more specifically about .5% to about 1%, more specifically about 0.5% to about 2%, more specifically about 1% to about 3% more specifically about .5% to about 5% by weight with respect to the overall composition.
  • the operating temperature is between about 3C to about 40C, in a further the range is about 3C to about 7C.
  • the ethylene response inhibitor releasing compound is in its solid granular form and/or in its salt form and is substantially free of moisture.
  • Ethylene responses may be initiated by either exogenous or endogenous,sources of ethylene.
  • ethylene responses include, for example, the ripening and/or senescence of flowers, fruits and vegetables, abscission of foliage, flowers and fruit, the shortening of life of ornamentals such as potted plants, cut flowers, shrubbery, seeds, and dormant seedlings, in some plants (e.g., pea) the inhibition of growth, and in other plants (e.g., rice) the stimulation of growth.
  • Additional ethylene responses or ethylene-type responses that may be inhibited by active compounds of the present invention include, but are not limited to, auxin activity, inhibition of terminal growth, control of apical dominance, increase in branching, increase in tillering, changing bio-chemical compositions of plants (such as increasing leaf area relative to stem area), abortion or inhibition of flowering and seed development, lodging effects, stimulation of seed germination and breaking of dormancy, and hormone or epinasty effects.
  • methods according to embodiments of the present invention inhibit the ripening and/or senescence of vegetables.
  • vegetable ripening includes the ripening of the vegetable while still on the vegetable-bearing plant and the ripening of the vegetable after having been harvested from the vegetable-bearing plant.
  • Vegetables which may be treated by the method of the present invention to inhibit ripening and/or senescence include leafy green vegetables such as lettuce (e.g., Lactuea saliva), spinach (Spinaca oleracea), and cabbage (Brassica oleracea), various roots, such as potatoes (Solanum tuberosum) and carrots (Daucus), bulbs, such as onions (Allium sp.), herbs, such as basil (Ocimum basilicum), oregano (Origanum vulgare), dill (Anethu graveolens), as well as soybean (Glycine max), lima beans (Phaseolus limensis), peas (Lathyrus spp.), corn (Zea mays), broccoli (Brassica oleracea italica), cauliflower (Brassica oleracea botrytis), and asparagus (Asparagus officinalis).
  • lettuce e.g., Lactuea saliva
  • methods according to embodiments of the present invention inhibit the ripening of fruits.
  • fruit ripening includes the ripening of fruit while still on the fruit-bearing plant as well as the ripening of fruit after having been harvested from the fruit-bearing plant.
  • Fruits which may be treated by the method of the present invention to inhibit ripening include tomatoes (Lycopersicon esculentum), apples (Malus domestica), bananas (Musa sapientum), pears (Pyrus communis), papaya (Carica papaya), mangoes (Mangifera indica), peaches (Prunus persica), apricots (Prunus armeniaca), nectarines (Prunus persica nectarina), oranges (Citrus sp.), lemons (Citrus limonia), limes (Citrus aurantifolia), grapefruit (Citrus paradisi), tangerines (Citrus nobilis deliciosa), kiwi (Actinidia chinenus), melons such as cantaloupe (C.
  • cantalupensis and musk melon (C. melo), pineapple (Aranas comosus), persimmon (Diospyros sp.), various small fruits including berries such as strawberries (Fragaria), blueberries (Vaccinium sp.) and raspberries (e.g., Rubus ursinus), green beans (Phaseolus vulgaris), members of the genus Cucumis such as cucumber (C. sativus), and avocados (Persea americana).
  • ornamental plants which may be treated by the method of the present invention to inhibit senescence and/or to prolong flower life and appearance (e.g., delay wilting), include potted ornamentals, and cut flowers.
  • Potted ornamentals and cut flowers which may be treated with the present invention include azalea (Rhododendron spp.), hydrangea (Macrophylla hydrangea), hybiscus (Hibiscus rosasanensis), snapdragons (Antirrhinum sp.), poinsettia (Euphorbia pulcherima), cactus (e.g.
  • plants which may be treated by the method of the present invention to inhibit abscission of foliage, flowers and fruit include cotton (Gossypium spp.), apples, pears, cherries (Prunus avium), pecans (Carva illinoensis), grapes (Vitis vinifera), olives (e.g. Vitis vinifera and Olea europaea), coffee (Coffea arabica), snapbeans (Phaseolus vulgaris), and weeping fig (ficus benjamina), as well as dormant seedlings such as various fruit trees including apple, ornamental plants, shrubbery, and tree seedlings.
  • shrubbery which may be treated according to the present invention to inhibit abscission of foliage include privet (Ligustrum sp.), photinea (Photinia sp.), holly (Ilex sp.), ferns of the family Polypodiaceae, schefflera (Schefflera sp.), aglaonema (Aglaonema sp.), Laceaster (Cotoneaster sp.), barberry (Berberis sp.), waxmyrfle (Myrica sp.), abelia (Abelia sp.), acacia (Acacia sp.) and bromeliades of the family Bromeliaceae.
  • privet Ligustrum sp.
  • photinea Pierhotinia sp.
  • holly Ilex sp.
  • ferns of the family Polypodiaceae schefflera (Schefflera sp.), agla
  • the desired article may be produced by any conventional process of making a plastic article that includes, but is not limited to, extrusion, melt inflation (e.g. blown film, blow moulding, thermoforming) and/or injection molding.
  • melt inflation e.g. blown film, blow moulding, thermoforming
  • injection molding e.g. blown film, blow moulding, thermoforming
  • the ethylene response inhibitor releasing material is blended with the thermoplastic and the resulting blend is subsequently processed into the desired shape article.
  • the ethylene response inhibitor releasing material is sensitive to high temperatures
  • the ethylene response inhibitor releasing material is blended at a downstream location (e.g. at a downstream point in the extruder) so the ethylene response inhibitor releasing material is subjected to a minimum amount of high temperature processing.
  • the plastic film composition is based on the particular requirements of the fruit and/or vegetable packaged.
  • the loading of active agent can range from 0.5 - 10% by weight of the total, more specifically 1-5%%.
  • the film thickness may be in the range of 0.2 mm - 1.4 mm, more specifically, 0.4 - 0.6 mm.
  • the film can be placed in a sealed container either.
  • the activation relative humidity is controlled by at least the moisture vapor transmission of the composition (e.g. the thermoplastic blend) and the ability of the composition to direct moisture effectively to the active agent.
  • the release rate of the active agent in the film is controlled by at least the following: (1) the loading of active agent in the plastic, (2) the thickness of the plastic, and (3) moisture vapor transmission properties of the thermoplastic.
  • the film may be manufactured in any conventional method.
  • the film is manufactured in an extrusion process packaged in a continuous master roll.
  • Multi-layer film constructions are possible.
  • An adhesive layer with a release liner may be applied to one side of the film.
  • a gas barrier layer may be applied to one side of the film.
  • the formulation of the ethylene response inhibitor releasing composition of the present invention is designed based on one or more of the following considerations: the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition should not release below a specified relative humidity (i.e. shelf stability); the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition should release above a specified relative humidity; the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition should release over a specified time (e.g.
  • the amount of ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition should result in substantially no the ethylene response inhibitor releasing material after the release; the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition should be designed to withstand processing conditions during the forming of the composition (e.g. 100 C).
  • the ethylene response inhibitor releasing composition comprises one more moisture transmitting materials that are capable of surrounding (e.g. have a preferential affinity towards) the ethylene response inhibitor releasing material when incorporated within the thermoplastic.
  • these moisture transmitting materials act as an osmotic regulator (e.g. controls the Rh that the ethylene response inhibitor releasing material is exposed to) surrounding the ethylene response inhibitor releasing material.
  • PEG polyethylene glycol
  • moisture transmitting materials similar to PEG, have the ability to substantially surround the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition and to transmit, rather than absorbs moisture.
  • suitable materials may include, but are not limited to,: (1) polyethylene oxide, (2) polyvinylpyrilodone, vinyl-acetate (“PVP-VA”), (3) Pluronic, PEBAX and (4) EVA-copolymer (with higher VA content).
  • a film was composed of a thermoplastic blend having an active agent of the ethylene response inhibitor releasing material.
  • Two active films were manufactured with different concentrations of the ethylene response inhibitor releasing material (e.g. SmartFresh 1-MCP complex): (1) a 1% concentration and (2) a 5% concentration.
  • the film formulations had the following compositions: Sample 1:
  • Sorbitol 10% where Elvax 3174 is an ethylene vinyl-acetate manufactured by Dupont (E.I.) de Nemours; "SmartFresh” is 1-methylcyclopropene (MCP) manufactured by AgroFresh, a division of Rohm & Haas; and Carbowax 1000 is a polyethylene glycol (PEG), manufactured by The Dow Chemical Company.
  • Elvax 3174 is an ethylene vinyl-acetate manufactured by Dupont (E.I.) de Nemours
  • SmartFresh is 1-methylcyclopropene (MCP) manufactured by AgroFresh, a division of Rohm & Haas
  • Carbowax 1000 is a polyethylene glycol (PEG), manufactured by The Dow Chemical Company.
  • Each sample was produced by the following process. First, Carbowax 1000 was heated above its melt temperature ⁇ 60C into a liquid form. Second, the Smart Fresh Complex was mixed into the Carbowax, using the proper weight ratio for the sample type. Finally, the calcium carbonate was added to the Carbowax/SmartFresh blend and hand mixed. The blended mixture was allowed to cool so that the material solidified. The resultant mixture was in a powdered form.
  • the resultant mixture was then formed into a film using a Leistriz twin screw extruder.
  • the extruder had 11 -independently controlled temperature zones.
  • the Elvax 3174 was loaded into a K-Tron material feeder and side stuffed into the Leistriz extruder at the most upstream feed location.
  • the blended powder of Carbowax/SmartFresh/Calcium Carbonate was fed into the extruder in the most downstream feed location.
  • the blended powder was then mixed with the Elvax in the extruder.
  • the highest temperature recorded by the thermoplastic compositions was 92 C.
  • the extruded material was fed into a three roll calendaring stack. The three roll stack was used to both form the film to its final thickness and to cool the molten material into a solid form.
  • the material was passed through a nip between two rolls; traveled over the surface of the center roll, passed through a second nip, traveled under the bottom roll and then transported towards the winder.
  • the nip pressures and the temperatures of each of the rolls were controlled independently.
  • the film was then passed through an NDC thickness gauge. This gauge had a traversing head, which emitted and measured gamma rays, which were passed through the film. Cross machine direction and machine direction data were gathered and displayed on a touch screen.
  • the film was then slit to the desired width and wound onto a core using a single shaft center drive winder.
  • the resulting film was about 0.4 mm thick and was cut into rectangular shapes.
  • the films were exposed to a moisture environment at 25C in a closed container.
  • the headspace was sampled at regular intervals to determine the concentration of 1-MCP in the headspace.
  • the headspace was sampled until all the 1-MCP had been released.
  • Carbowax polyethylene glycol
  • sorbitol may acts as a competitor for moisture to the ethylene response inhibitor releasing material within the ethylene response inhibitor releasing composition - thus have an undesirable effect.
  • the release rate of the film can be controlled by at least one or more of the following: (1) the selection of the type of thermoplastic based on its specific gas transmission properties (specifically MVTR), (2) the amount of moisture concentrating thermoplastic, and (3) the geometry of the film (surface area to thickness ratio). It is further believed that, in another embodiment, the calcium carbonate filler particle may assist in providing microscopic pathways throughout the thermoplastic composition.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un procédé d'inhibition de la réponse éthylène dans des fleurs, des fruits, des légumes et des plantes. Ce procédé consiste à appliquer sur le végétal une quantité efficace d'une composition libérant un inhibiteur de réponse éthylène. Ladite composition contient : une base thermoplastique, une charge, un matériau libérant un inhibiteur de réponse éthylène et un matériau transmettant de l'humidité, ledit matériau concentrant l'humidité sur le matériau libérant un inhibiteur de réponse éthylène. Le procédé selon l'invention consiste ensuite à activer la composition à une humidité d'au moins environ 80 % Rh à 5 °C.
PCT/US2004/014611 2003-05-09 2004-05-10 Composition thermoplastique contenant un materiau liberant un inhibiteur de reponse ethylene Ceased WO2004101668A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46943003P 2003-05-09 2003-05-09
US60/469,430 2003-05-09

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WO2004101668A2 true WO2004101668A2 (fr) 2004-11-25
WO2004101668A3 WO2004101668A3 (fr) 2005-09-29

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1597967A1 (fr) * 2004-05-19 2005-11-23 Rohm And Haas Company Compositions comprenant des cyclopropènes et des agents complexant les métaux
CN102440238A (zh) * 2010-07-02 2012-05-09 罗门哈斯公司 包覆的粉状颗粒
WO2012062000A1 (fr) * 2010-11-14 2012-05-18 中国科学院华南植物园 Procédé pour garder frais des agrumes de shatang pourvus de feuilles
US8603524B2 (en) 2007-01-17 2013-12-10 Dow Agrosciences Llc Delivery of ethylene blocking and/or promoting agents
WO2014124124A1 (fr) * 2013-02-08 2014-08-14 Agrofresh Inc. Processus de revêtement à fusion sèche et formulation pour composés volatils
US10647834B2 (en) 2018-04-27 2020-05-12 Fresh Inset S.A. Compositions and articles comprising complexes of 1-methylcycloproprene and alpha-cyclodextrin
WO2023101935A1 (fr) * 2021-11-30 2023-06-08 Verdant Technologies, Llc Poches actives et procédés d'utilisation
US11730166B2 (en) 2020-02-03 2023-08-22 Fresh Inset S.A. Stable 1-methylcyclopropene compositions and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6017849A (en) * 1998-08-20 2000-01-25 Biotechnologies For Horticulture, Inc. Synthesis methods, complexes and delivery methods for the safe and convenient storage, transport and application of compounds for inhibiting the ethylene response in plants
NZ519036A (en) * 1999-11-23 2004-02-27 Univ North Carolina State Methods of blocking an ethylene response in plants using cyclopropene derivatives

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8541344B2 (en) 2004-05-19 2013-09-24 Rohm And Haas Company Compositions with cyclopropenes and metal-complexing agents
EP1597967A1 (fr) * 2004-05-19 2005-11-23 Rohm And Haas Company Compositions comprenant des cyclopropènes et des agents complexant les métaux
US8603524B2 (en) 2007-01-17 2013-12-10 Dow Agrosciences Llc Delivery of ethylene blocking and/or promoting agents
CN102440238B (zh) * 2010-07-02 2014-06-04 罗门哈斯公司 包覆的粉状颗粒
EP2401917A3 (fr) * 2010-07-02 2012-05-30 Rohm and Haas Company Particules de poudre revêtue
CN102440238A (zh) * 2010-07-02 2012-05-09 罗门哈斯公司 包覆的粉状颗粒
US9730440B2 (en) 2010-07-02 2017-08-15 Agrofresh Inc. Coated powder particles
US10091993B2 (en) 2010-07-02 2018-10-09 Agrofresh Inc. Coated powder particles
WO2012062000A1 (fr) * 2010-11-14 2012-05-18 中国科学院华南植物园 Procédé pour garder frais des agrumes de shatang pourvus de feuilles
WO2014124124A1 (fr) * 2013-02-08 2014-08-14 Agrofresh Inc. Processus de revêtement à fusion sèche et formulation pour composés volatils
US10647834B2 (en) 2018-04-27 2020-05-12 Fresh Inset S.A. Compositions and articles comprising complexes of 1-methylcycloproprene and alpha-cyclodextrin
US11248109B2 (en) 2018-04-27 2022-02-15 Fresh Inset S.A. Compositions and articles comprising complexes of 1-methylcycloproprene and alpha-cyclodextrin
US12043733B2 (en) 2018-04-27 2024-07-23 Fresh Inset S.A. Compositions and articles comprising complexes of 1-methylcyclopropene and α-cyclodextrin
US11730166B2 (en) 2020-02-03 2023-08-22 Fresh Inset S.A. Stable 1-methylcyclopropene compositions and uses thereof
WO2023101935A1 (fr) * 2021-11-30 2023-06-08 Verdant Technologies, Llc Poches actives et procédés d'utilisation

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