WO2016062684A1 - Polyolefin-containing composition with anti-fog properties - Google Patents

Polyolefin-containing composition with anti-fog properties Download PDF

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Publication number
WO2016062684A1
WO2016062684A1 PCT/EP2015/074207 EP2015074207W WO2016062684A1 WO 2016062684 A1 WO2016062684 A1 WO 2016062684A1 EP 2015074207 W EP2015074207 W EP 2015074207W WO 2016062684 A1 WO2016062684 A1 WO 2016062684A1
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WO
WIPO (PCT)
Prior art keywords
polyolefin
glycerol
ethoxylated
agricultural film
film according
Prior art date
Application number
PCT/EP2015/074207
Other languages
English (en)
French (fr)
Inventor
Geesje Klasina Spijkerman
Ted Henri Wilfred Cornelius KAMPEN
Auke Gerardus Talma
Original Assignee
Akzo Nobel Chemicals International B.V.
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 Akzo Nobel Chemicals International B.V. filed Critical Akzo Nobel Chemicals International B.V.
Priority to CA2962831A priority Critical patent/CA2962831A1/en
Publication of WO2016062684A1 publication Critical patent/WO2016062684A1/en
Priority to IL251231A priority patent/IL251231A0/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A01G13/02—Protective coverings for plants; Coverings for the ground; Devices for laying-out or removing coverings
    • A01G13/0256—Ground coverings
    • A01G13/0268—Mats or sheets, e.g. nets or fabrics
    • A01G13/0275—Films
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G9/00—Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
    • A01G9/14—Greenhouses
    • A01G9/1407—Greenhouses of flexible synthetic material
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G9/00—Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
    • A01G9/14—Greenhouses
    • A01G9/1438—Covering materials therefor; Materials for protective coverings used for soil and plants, e.g. films, canopies, tunnels or cloches

Definitions

  • This invention relates to the prevention of fogging on the surface of agricultural films.
  • Polyolefins such as polyethylene, are used in various agricultural applications, such as greenhouse covers and energy screens. Polyolefins have a high resistance to moisture vapour transmission and high transparency, which is evidently essential for agricultural applications.
  • any water that evaporates from the soil or plants starts to condense on the inner surface of the polyolefin film.
  • the water droplets form a fogged surface, thereby reducing the visual transparency of the film. This effect is generally called “fogging” or “clouding”. Fogging leads to reduced light transmission, which negatively affects the growth of crops covered by said film.
  • antifog agents can be added to the polyolefin.
  • These antifog agents can be coated on the polyolefin film, or they can be incorporated in the polyolefin film. Incorporation in the film is generally preferred over coating on the film because of the lower processing costs, the lower environmental impact (i.e. no coating solvents required), and the absence of a separate layer that can be wiped or washed off the surface.
  • Examples of known antifog agents for incorporation in polyolefin films are monoglycerol esters of fatty acids, sorbitan esters of fatty acids, and combinations thereof.
  • the antifog action of the incorporated antifog agents is most likely due to the migration of the antifog agent to the film's surface, thereby enhancing the hydrophilicity of the surface and decreasing the surface tension of the water, which causes the water to form a continuous, visually clear film instead of a fogged surface comprising individual droplets of water.
  • Fogging may occur under relatively cold conditions (below ambient temperature, i.e. cold outside conditions) and relatively warm conditions (above ambient temperature, e.g. in warm humid outside conditions).
  • the first are called cold fog conditions; the second are called hot fog conditions.
  • WO 84/03296 discloses the use as antifog agent in low density polyethylene of a fatty acid ester alkoxylated with 10-55 ethylene oxide groups.
  • JP-A 62-04 240 discloses a polyethylene film with antifog properties which contains a surface active agent with a crystallization temperature of 23°C or more, a glycerol or sorbitan ester of an unsaturated fatty acid with a crystallization temperature of 23°C or less, and a plasticizer.
  • sorbitan or glycerol esters optionally alkoxylated with 0.5-5.0 ethylene oxide or propylene oxide groups are mentioned.
  • non- alkoxylated sorbitan sesquipalmitate and non-alkoxylated diglycerol distearate were used.
  • plasticizer di-2-ethylhexyl phthalate and tricresyl phosphate are indicated as preferred.
  • the plasticizer in this prior art composition is essential for obtaining sufficient antifog properties.
  • the plasticizer weakens the film to such an extent that its mechanical properties are insufficient for agricultural applications.
  • plasticizers such as phthalates and phosphates are known to be toxic to humans, but also exhibit phytotoxicity, and their presence in agricultural films is also undesired from that perspective. It is therefore an object of the present invention to provide an agricultural film that is not phytotoxic, has good hot fog behaviour, and a high mechanical strength. That is: a mechanical strength which allows the composition to be applicable for agricultural applications.
  • a polyolefin-containing composition comprising, as antifog agent, one or more ethoxyiated glycerol esters of saturated fatty acids.
  • the composition should be substantially deficient of plasticizer.
  • the ester(s) should have a molar average degree of ethoxylation in the range of 1 .0 to below 5.0.
  • the esters have an average degree of ethoxylation in the range 1 .0-4.0, more preferably 1 .0-3.0, and most preferably 2.0-3.0.
  • the present invention therefore relates to an agricultural film having a visible light transmission of at least 50%, said film comprising a polyolefin-containing composition that is essentially free of plasticizer and comprises a polyolefin having dispersed therein one or more glycerol esters of saturated fatty acid with 12-22 carbon atoms, said ester(s) having been ethoxyiated to an average degree of 1 .0 to below 5.0 moles of ethylene oxide groups per mole of glycerol ester.
  • the agricultural film according to the present invention should have a visible light transmission of at least 50%, more preferably 60%, even more preferably at least 75%, and most preferably at least 80%.
  • Visible light is defined as light with a wavelength in the range 380-770 nm.
  • the visible light transmission of the film is determined by spectrophotometry.
  • the glycerol ester that serves as antifog agent has been ethoxylated. Ethoxylation processes are well known to those skilled in the art and preferably involve the treatment of molten ester with ethylene oxide under high pressure and temperature in the presence of a base catalyst. During this process, initial mono-glycerol esters may react to form di- and tri-glycerol esters and glycerol. Likewise, di-glycerol esters may react to form mono- and tri-glycerol esters and glycerol, etc. Essentially all these components will be ethoxylated during the process.
  • the average degree of ethoxylation of the resulting material can be controlled by the amount ethylene oxide, as is also well known by the skilled person.
  • the one or more glycerol esters generally will consist of a mixture of glycerol esters, which mixture has been ethoxylated to an average degree of ethoxylation of 1 .0 to less than 5.0.
  • the average degree of ethoxylation of the glycerol ester(s) is in the range of 1 .0 to below 5.0, which means that the product obtained by the ethoxylation reaction contains, on average, 1 .0 to less than 5.0 mole of ethylene oxide per mole of initial glycerol ester.
  • This average degree of ethoxylation can be determined by determining the hydroxyl value of the material. This value can be determined by a titration method. According to this method, a solution of phthalic anhydride in pyridine is added to a sample of ethoxylated glycerol ester. Hydroxyl groups in the sample react under enhanced temperature with phthalic anhydride.
  • the reaction is catalysed by 4-dimethyl-aminopyridine.
  • the phthalic anhydride that has not been consumed by the sample and the acid that has formed are determined by titration with alkali. Also the total added amount of phthalic anhydride in a blank solution is determined in this way.
  • the results allow the calculation of free OH-functionalities in the sample, from which the number of moles of ethoxylated product can be calculated. With the sample weight one can calculate the average molecular weight and, hence, the average number of moles of ethylene oxide groups per mole of initial glycerol ester.
  • JP-A 02-163188 discloses the use of fatty acid esters alkoxylated with 3-8 ethylene oxide groups as antifog and antifrost agent in PVC.
  • PVC is much more polar than polyolefins.
  • the migration behaviour of the antifog agent in these polymers will greatly differ.
  • PVC and polyolefins also differ in crystallization behaviour; a property that also affects the migration of the antifog agent.
  • the fact that a particular compound is able to perform well as antifog agent in PVC does not predict its suitability in polyolefins.
  • the glycerol esters to be ethoxylated can be prepared by known procedures, such as the giycerolysis of natural oils or fats, which are generally mixtures of various fatty acid triglycerides. This process leads to a complex mixture of alpha- and beta-monoglycerides, diglycerides, traces of triglycerides, and free fatty acids. The components of such mixtures can be separated by suitable distillation procedures.
  • Suitable oils and fats are beef tallow, mutton tallow, butter fat, coconut oil, corn oil, cotton seed oil, lard oil, olive oil, peanut oil, palm oil, soy bean oil, sesame oil, sunflower oil, rapeseed oil, and their partial or fully hydrogenated derivatives.
  • Commercially available glycerol mono-esters generally contain traces of preservatives, free glycerol, free fatty acids, and glycerol di- and tri-esters.
  • the saturated fatty acid-originating part of the glycerol ester has 12 to 22 carbon atoms, preferably 14 to 20 carbon atoms, and most preferably 16 to 18 carbon atoms.
  • the fatty acid may be substituted by hydroxy groups.
  • saturated fatty acids with 12 to 22 carbon atoms are lauric acid (C12), myristic acid (C14), palmitic acid (C16), stearic acid (C18), hydrogenated ricinoleic acid (C18), arachidic acid (C20), and behenic acid (C22).
  • the glycerol esters to be ethoxyalated can be esters of monoglycerol, diglycerol, and polyglycerol. It may also be mixtures of glycerol esters of different saturated fatty acids, e.g. fatty acids with 16 and with 18 carbon atoms.
  • the glycerol esters to be ethoxyalated can be mono-esters, di-esters, tri-esters, and mixtures thereof.
  • a mixture of mono-esters, di- esters, and tri-esters is used, a large part - i.e. 20-90 wt%, more preferably 30- 80 wt%, even more preferably 40-70 wt%, and most preferably 40-60 wt% - of which consists of mono-esters.
  • the composition may contain ethoxylated unsaturated fatty acid esters.
  • ethoxylated unsaturated fatty acid esters An example thereof is ethoxylated glycerol mono-oleate.
  • ethoxylated unsaturated fatty acid ester is present in the polyolefin-containing composition, it is preferably present in an amount of less than 70 wt%, more preferably less than 60 wt%, and most preferably less than 50 wt%, meaning that at least 30 wt%, more preferably at least 40 wt%, and most preferably at least 50 wt% of the ethoxylated fatty acid esters in the composition consist of ethoxylated saturated fatty acid esters.
  • the polyolefin-containing composition is essentially free of plasticizer. "Essentially free” in this respect means: an amount that does not affect the mechanical properties of the resulting agricultural film. Most preferably, the composition is free of plasticizer.
  • plasticizers examples include phosphates and phthalates, such as tricresyl phosphate and di-2-ethylhexyl phthalate.
  • the polyolefin-containing composition is also free of lubricants.
  • Lubricants make the surface of the polymer more hydrophobic, due to their hydrophobic tail.
  • lubricants tend to form a double layer that migrates to the polymer's surface, sticking its apolar tails out of the polymer surface. This decreases the surface tension of the polymer and therefore counteracts the effect of antifog agents.
  • the ethoxylated glycerol ester can be incorporated in the polyolefin by mixing it into molten polyolefin using conventional techniques, such as extrusion, roll- milling or mixing it in a Banbury mixer.
  • the ester may be added to the polyolefin before or after said polyolefin has been melted.
  • the ethoxylated glycerol ester may be added as such, or in the form of a masterbatch in a polyolefin.
  • the resulting mixture is then solidified by cooling and then comminuted to a particle size satisfactory for further form shaping processes like blown film extrusion, cast film extrusion, hot melt extrusion, or equivalent heat-shaping operations.
  • compositions are also possible to incorporate this composition into a multi-layer system.
  • a multi-layer system will contain at least one layer made from this composition.
  • Other layers of such a multi-layer system may be based on, for instance, polyamide (e.g. nylon) and/or polyester (e.g. polyethylene terephthalate).
  • Multi-layer systems can be prepared by co-extrusion or lamination.
  • Suitable polyolefins for use in the present invention include polyethylene, polypropylene (PP), random- and block-copolymers of ethylene and propylene, ethylene vinyl acetate copolymer (EVA), and polymers obtained from ethylene or propylene copolymerized with minimal amounts of other mono-olefinic monomers such as butene, isobutylene, acrylic acids, esters of acrylic acids, styrene or combinations thereof.
  • Polyethylenes include high density polyethylene (HDPE; defined by a density of greater or equal to 0.941 g/cm 3 ), medium density polyethylene (MDPE; defined by a density range of 0.926-0.940 g/cm 3 ), linear low density polyethylene (LLDPE; defined by a density range of 0.915-0.925 g/cm 3 ), low density polyethylene (LDPE; defined by a density range of 0.910-0.940 g/cm 3 ), very low density polyethylene (VLDPE; defined by a density range of 0.880-0.915 g/cm 3 ), and blends thereof.
  • HDPE high density polyethylene
  • MDPE medium density polyethylene
  • LLDPE linear low density polyethylene
  • LDPE low density polyethylene
  • VLDPE very low density polyethylene
  • Preferred polyolefins are LDPE, EVA, and polymer blends containing LDPE and/or EVA.
  • the ethoxylated glycerol ester is incorporated in the polyolefin in an amount sufficient to impart fog resistance to the agricultural film. If an excess amount of antifog agent is incorporated in the polyolefin, the polyolefin tends to be tacky and has a greasy feel. The blocking and slip properties of the resulting agricultural film may also be adversely affected. Moreover, an excess of antifog agent in the film adversely affects the adhesion of inks thereto.
  • the ethoxylated glycerol ester is therefore incorporated in the polyolefin- containing composition in an amount of 0.2-6 wt%, more preferably 1 -5 wt%, and most preferably 2-4 wt%, based on the weight of the polyolefin-containing composition.
  • the polyolefin film may contain various conventional additives, such as anti-static agents, anti-oxidants, anti- ozonants, slip agents, anti-block agents, light stabilizers (e.g. HALS), UV stabilizers, colorants, tackifiers, and the like, if so desired.
  • the polyolefin-containing composition should, however, be essentially free of compounds that severely hinder the transmission of visible light through the resulting film.
  • examples of such compounds are carbon black and other carbon- based materials.
  • the agricultural film according to the present invention can be used for various agricultural applications, such as energy screens and greenhouse covers.
  • Beakers of 600 ml (high model, 150 mm, 80 mm ⁇ , without spout) were filled with 350 ml of tap water. Films prepared according to the Examples below were cut and placed on the beaker and fixed with a rubber band. The beakers were placed in a water bath at 40°C and fog was determined visually after 5, 10, 15 and 30 minutes and after 1 , 2 and 5 hours on the first day; and once a day thereafter.
  • the Fog Score is the best result obtained over time. It was scored according to the following system:
  • Hot fog durability is defined as the time until the film started to form droplets and the Fog Score dropped below D.
  • EVA ethylene-vinyl acetate copolymer
  • MFS glycerol monostearate
  • the so formed 5 wt% masterbatch was dry blended with the same EVA polymer as mentioned above to form a composition comprising a 1 wt% ethoxylated glycerol monostearate in EVA.
  • This composition was shaped to form a film using film blowing equipment. The visible light transmission of the resulting film more than 80%.
  • Example 1 was repeated, except that glycerol monostearate with an average degree of ethoxylation of 5.0 was used.
  • the antifog performance of this film is listed in Table 1 . Comparative Example B
  • Example 1 was repeated, except that glycerol monostearate with an average degree of ethoxylation of 10.0 was used.
  • the antifog performance of this film is listed in Table 1 . Comparative Example C
  • Example 1 was repeated, except that glycerol monostearate with an average degree of ethoxylation of 30.0 was used.
  • the antifog performance of this film is listed in Table 1 . Comparative Example D
  • Example 1 was repeated, except that propoxylated glycerol monostearate with an average degree of propoxylation of 2.5 was used.
  • Example 1 was repeated, except that ethoxylated glycerol mono-oleate (GMO) with an average degree of ethoxylation of 5.0 was used.
  • GMO ethoxylated glycerol mono-oleate
  • Example 1 was repeated, except that instead of 1 wt%, 1 .5 wt% of glycerol monostearate ethoxylated to an average degree of ethoxylation of 2.5 was present in the final film.
  • the antifog performance of this film is listed in Table 1 .
  • Example 2 was repeated, except that the film contained an additional amount of 1 .5 wt% of ethoxylated glycerol mono-oleate with an average degree of ethoxylation of 5.0.
  • the antifog performance of this film is listed in Table 1 .
  • Example 3 was repeated, except that the film contained an additional amount of 1 .5 wt% 2-ethyl-hexyl phthalate (a plasticizer).
  • the antifog performance of this film is listed in Table 1 .
  • Example 4 was repeated, except that glycerol monostearate with an average degree of ethoxylation of 10.0 was used.
  • the antifog performance of this film is listed in Table 3.
  • Example 4 was repeated, except that that glycerol monostearate with an average degree of ethoxylation of 30.0 was used.
  • the antifog performance of this film is listed in Table 3.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Soil Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Protection Of Plants (AREA)
  • Greenhouses (AREA)
PCT/EP2015/074207 2014-10-23 2015-10-20 Polyolefin-containing composition with anti-fog properties WO2016062684A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA2962831A CA2962831A1 (en) 2014-10-23 2015-10-20 Polyolefin-containing composition with anti-fog properties
IL251231A IL251231A0 (en) 2014-10-23 2017-03-16 A preparation containing polyolefin with anti-fog properties

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14190119 2014-10-23
EP14190119.9 2014-10-23

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WO2016062684A1 true WO2016062684A1 (en) 2016-04-28

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AR (1) AR102909A1 (zh)
CA (1) CA2962831A1 (zh)
IL (1) IL251231A0 (zh)
TW (1) TW201623563A (zh)
WO (1) WO2016062684A1 (zh)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3245864A1 (en) 2016-05-20 2017-11-22 Akzo Nobel Chemicals International B.V. Anti-fog agent
EP3428227A1 (en) 2017-07-14 2019-01-16 Akzo Nobel Chemicals International B.V. Anti-fog agent
EP3654756B1 (en) 2017-07-17 2021-10-06 AB Ludvig Svensson Greenhouse screen
CN115490940A (zh) * 2021-06-17 2022-12-20 万华化学集团股份有限公司 一种防雾透气耐老化的透明聚乙烯复合材料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111823532A (zh) * 2020-07-17 2020-10-27 甘肃福雨塑业有限责任公司 一种农用多功能水晶po转光大棚膜及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003296A1 (en) * 1983-02-28 1984-08-30 Dow Chemical Co Fog-resistant olefin polymer films
EP0524404A1 (en) * 1991-05-28 1993-01-27 Fuji Photo Film Co., Ltd. Resin composition and packaging material for packaging photosensitive materials
EP0933400A1 (en) * 1997-05-12 1999-08-04 Clariant International Ltd. Synthetic resin film for agricultural use excellent in antifog and antimist properties
JPH11335486A (ja) * 1998-05-27 1999-12-07 Kao Corp 合成樹脂用防曇剤組成物
US20030127625A1 (en) * 2001-03-01 2003-07-10 Hiroshi Nagasawa Antifogging agent composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003296A1 (en) * 1983-02-28 1984-08-30 Dow Chemical Co Fog-resistant olefin polymer films
EP0524404A1 (en) * 1991-05-28 1993-01-27 Fuji Photo Film Co., Ltd. Resin composition and packaging material for packaging photosensitive materials
EP0933400A1 (en) * 1997-05-12 1999-08-04 Clariant International Ltd. Synthetic resin film for agricultural use excellent in antifog and antimist properties
JPH11335486A (ja) * 1998-05-27 1999-12-07 Kao Corp 合成樹脂用防曇剤組成物
US20030127625A1 (en) * 2001-03-01 2003-07-10 Hiroshi Nagasawa Antifogging agent composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3245864A1 (en) 2016-05-20 2017-11-22 Akzo Nobel Chemicals International B.V. Anti-fog agent
EP3428227A1 (en) 2017-07-14 2019-01-16 Akzo Nobel Chemicals International B.V. Anti-fog agent
EP3654756B1 (en) 2017-07-17 2021-10-06 AB Ludvig Svensson Greenhouse screen
EP3654756B2 (en) † 2017-07-17 2024-06-12 AB Ludvig Svensson Greenhouse screen
CN115490940A (zh) * 2021-06-17 2022-12-20 万华化学集团股份有限公司 一种防雾透气耐老化的透明聚乙烯复合材料及其制备方法
CN115490940B (zh) * 2021-06-17 2024-02-02 万华化学集团股份有限公司 一种防雾透气耐老化的透明聚乙烯复合材料及其制备方法

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CA2962831A1 (en) 2016-04-28
IL251231A0 (en) 2017-05-29
AR102909A1 (es) 2017-04-05
TW201623563A (zh) 2016-07-01

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