WO2004052979A1 - Composition copolymere thermoplastique transformant la lumiere et servant a changer un rayonnement ultraviolet en zone spectrale rouge et procede de production associe - Google Patents

Composition copolymere thermoplastique transformant la lumiere et servant a changer un rayonnement ultraviolet en zone spectrale rouge et procede de production associe Download PDF

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WO2004052979A1
WO2004052979A1 PCT/IL2002/000993 IL0200993W WO2004052979A1 WO 2004052979 A1 WO2004052979 A1 WO 2004052979A1 IL 0200993 W IL0200993 W IL 0200993W WO 2004052979 A1 WO2004052979 A1 WO 2004052979A1
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Prior art keywords
transforming
copolymer composition
thermoplastic light
composition according
group
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PCT/IL2002/000993
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English (en)
Inventor
Edward Bormashenko
Benjamin Finkelshtein
Yuri Shmukler
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Polymaster Ltd.
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Priority to PCT/IL2002/000993 priority Critical patent/WO2004052979A1/fr
Priority to AU2002358954A priority patent/AU2002358954A1/en
Publication of WO2004052979A1 publication Critical patent/WO2004052979A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • C08K5/07—Aldehydes; Ketones
    • 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
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide

Definitions

  • the invention relates to a thermoplastic light-transforming copolymer composition useful for shifting of ultraviolet radiation of solar or other radiation by means of transforming said radiation into red spectral region providing improved film or glass for greenhouses, decorative elements, advertisement purposes and a method for producing the same.
  • Polycarbonate-based polymer compositions containing pyrazine derivatives as active additives, are known in the art. These compositions are applied in silicate glass and shifting ultraviolet radiation (hereafter denoted 'UV') into the radiation of blue spectrum (See for example Japan Patent No. 199,814).
  • 'UV' shifting ultraviolet radiation
  • the main drawback of those compositions is their limited application area. More specifically, these compositions are characterized as inappropriate for use in agriculture, because it provided only the blue range radiation whereas maximal crop yields and growth is at the red range radiation.
  • compositions for films are known in the art, and comprises ethylene and Europium compounds (hereafter denoted as ⁇ u') as an active admixture.
  • ethylene and Europium compounds hereafter denoted as ⁇ u'
  • Such compounds may generalized at the structure of: Eu(D) 3 (HC), where D denoted diketone and (HC) denoted bidentate nitrous heterocyclic compound, e.g., 1,10-phenanthroline (See for example USSR Cert, of Authorship No. 1,381,128).
  • a polymer composition with active admixture for the production of ethylene-(co-)polymer films is also known in the art.
  • This composition contains active admixture of europium oxide or europium organic or inorganic salt; one or more ⁇ -diketone class compounds; bidentate nitrous heterocyclic or trialkyl(aryl) phosphinoxide class compound, and a saturated range organic acid salt of alkali or alkaline-earth metal and/or ammonium, or free amine.
  • the main drawback of said composition is its relatively low light stability, restricting its service life.
  • thermoplastic light-transforming copolymer composition useful for shifting of ultraviolet radiation of solar or other ultraviolet radiation source into red spectral region, comprising 0.001 - 5 % (wt) of each of the following ingredient groups in a polymeric continuous matrix: (A) organic and/or inorganic salts comprising at least one of the elements europium and yttrium;(B) at least one ⁇ -diketone substance; (C) a substance selected from the group of heterocycles comprising nitrogen or oxygen, organic amines, phosphides, or sulfide oxides; (D)a substance selected from the group of salts of organic acid and alkali or alkaline-earth metals and/or ammonium and/or free amine.
  • A organic and/or inorganic salts comprising at least one of the elements europium and yttrium
  • B at least one ⁇ -diketone substance
  • C a substance selected from the group of heterocycles comprising nitrogen or oxygen, organic amines, phos
  • thermoplastic light-transforming copolymer as described above, wherein said polymeric continuous matrix is selected from the group of high pressure or low density polyethylene, polypropylene, ethylene-propylene copolymer, ethylene-vinyl acetate copolymer, cellulose acetobutyrate, polystyrene, polyvinyl chloride, polycarbonate, polyacrylates, polyamides or polyesters.
  • thermoplastic light-transforming copolymer as described above, wherein said organic and/or inorganic salts of europium and yttrium are selected from: formic acid or its homologues comprising C 2 to C 18 hydrocarbon chains; trifluoroacetic acid and perfluorated homologues of said acid, comprising C 2 to C hydrocarbon chains; mono, di, and trichloroacetic acids; naphtyl-, phenyl- and diphenyloacetic acids; benzoic acid and its substituted derivatives comprising one to five halogen atoms per molecule or from one to five alkyl or alkoxyl groups comprising C ⁇ to 8 hydrocarbon chains; phenyl or benzoyl group; aromatic hydroxy acids comprising benzene or naphthalene and one to three hydroxy groups; aliphatic saturated diacids comprising C 3 to C 10 hydrocarbon chains; aliphatic unsaturated monoacids and dicarbon acids
  • thermoplastic light-transforming copolymer as described above, wherein the ⁇ -diketone is defined by at least one compound comprising a compound of the generic of R 1 C(0)CH 2 C(O)R 2 , wherein R 1 and R 2 represents independently group selected from: Ci to C 18 linear or branched alkyl substances; Ci to C perfluoroalkyl substances; C_ to Ci8 unsubstituted phenyl substances comprising one to five halogen atoms and/or one to five alkyl or alkoxyl groups; C ⁇ to C 4 perfluoroalkyl substances; polynuclear aromatic compounds selected from the group of 1 -naphtyl, 2-naphtyl, 9-anthracenyl, 9-phenantrenyl, 2-thenoyl, wherein said polynuclear compounds comprising up to four substituted residues; at least one 4-acyl-3-methyl-l-phenyl-2-pyrazoline
  • 1,4,5,8-tetraazaphenantrene and their derivatives either unsubstituted or containing one or two halogen atoms, nitro, amino, hydroxy, methyl, metoxy, and/or phenyl groups.
  • thermoplastic light-transforming copolymer as described above, wherein said heterocycles comprising nitrogen and/or oxygenes is comprising any member of the group of macrocyclic crown-ether compounds or their nitrous analogs, 15-crown-5, benzo-15-crown-5, 18-crown-6, dibenzo-18-crown-6, dicyclohexano-18-crown-6, 2,2,1-cryptands and 2,2,2-cryptands, cyclene, cyclame, dioxycyclame, hexacyclene, either unsubstituted or containing 1 to 4 acetic acid residues at nitrogen or carbon atoms.
  • thermoplastic light-transforming copolymer as described above, comprising inorganic salts of europium and yttrium in the mass ratio of 0.5:1.5 to 1.5:0.5 (A), thinoyl trifluoroacetone (B), tri-r ⁇ -octyl phosphine oxide (C), and sodium palmitate (D) at a mass ratio of 1:1.82:2.11:2.29.
  • thermoplastic light-transforming copolymer comprising carboxylate salts europium and yttrium acetate in the mass ratio of 1:1 to 1:10 (A), at least one 4-acyl-3-methyl-l-phenyl-2-pyrazoline-5-ons derivative, comprising but not limited to 4-benzoyl-3 -methyl- l-phenyl-2-pyrazoline-5 -on (B), 1,10-phenanthroline (C), and 1,10-hexadecyl amine (D) at a mass ratio of 1 :2.53:0.55:2.2.
  • thermoplastic light-transforming copolymer as described above, comprising inorganic salts europium and yttrium acetates in the mass ratio of 1:25 to 1:75 (A), thenoyl trifluoroacetone (B), 2,2'-dipyridine (C), and calcium stearate (D) at a mass ratio of ingredients B, C, and D is 1:0.23:1.23.
  • thermoplastic light-transforming copolymer as described above, comprising inorganic salts europium and yttrium acetates in the mass ratio of 1:1 to 1:10 (A), dibenzoyl methane (B , thenoyl trifluoroacetone (B 2 ), 2,2'-dipyridine (Ci.), 1,10-phenanthroline (C 2 ), and tribenzyl amine (D) at a mass ratio of 1:0.91:0.92:0.21:0.25:2.35.
  • thermoplastic light-transforming copolymer as described above, comprising inorganic salts europium and yttrium acetates in the mass ratio of 1:1 to 1:25 (A), thenoyl trifluoroacetone (B), 2,2'-dipyridine (Ci , dibenzo-18-crown-6 (C 2 ), and N,N' -dimethyl octadecyl amine (D) at a mass ratio of 1:1.8:1.5:0.4:0.8:3.
  • thermoplastic light-transforming copolymer as described above, comprising carboxylate salts europium and yttrium acetate in the mass ratio of 1 :25 to 1 :75 (A), dibenzoyl methane (B), 1,10-phenanthroline N-oxide (C), ammonium stearate (D ), and dioctyl sulfoxide (D 2 ) at a mass ratio of 1 :2:0.6:4:0.5.
  • thermoplastic light-transforming copolymer composition useful for shifting of ultraviolet radiation of solar or other radiation into red spectral region as defined in claim 1 and in any of previous claims, wherein comprising; admixing an efficient amount of said ingredients; extruding and granulating the obtained concentrate, comprising up to 20 % of said admixture; and diluting obtained material with the initial thermoplastic polymer to an efficient concentration.
  • thermoplastic light-transforming copolymer composition useful for shifting of ultraviolet radiation of solar or other radiation into red spectral region, has been developed and proved effective to preserve mechanical and visible-light spectrum range characteristics comparing with the initial polymer material, to maintain high processibility, long service period, and to provide simplicity of production applicable for industrial and agriculture uses.
  • thermoplastic light-transforming copolymer composition useful for the shifting of ultraviolet radiation, comprising the following ingredients, each of which is in the range of 1*10 "3 - 5 % (wt): (a) organic and/or inorganic salts comprising elements europium and yttrium; (b) ⁇ -diketone substances; (c) a substance selected from the group of heterocycles comprising nitrogen or oxygen, organic amines, phosphides, or sulfide oxides; and lastly (d), salts of organic acid and alkali or alkaline-earth metals and/or ammonium and/or free amine.
  • thermoplastic copolymer comprising high pressure or low density polyethylene, polypropylene, ethylene - propylene copolymer, ethylene - vinyl acetate copolymer, cellulose acetobutyrate, polystyrene, polyvinyl chloride, polycarbonate, polyacrylates, polyamides and polyesters.
  • thermoplastic copolymer comprising a mixture of inorganic europium and yttrium salts, wherein the said composition may contain hydrated or anhydrous nitrates or halides.
  • thermoplastic copolymer comprising said mixture of organic europium and yttrium salts, wherein said organic and/or inorganic salts of europium and yttrium are selected from: (a) formic acid or its homologues comprising C 2 to C 18 hydrocarbon chains; (b) trifluoroacetic acid and perfluorated homologues of said acid, comprising C 2 to C hydrocarbon chains; (c) mono, di, and trichloroacetic acids; (d) naphtyl-, phenyl- and diphenyloacetic acids; (e) benzoic acid and its substituted derivatives comprising one to five halogen atoms per molecule or from one to five alkyl or alkoxyl groups comprising Ci to C ⁇ 8 hydrocarbon chains; (f) phenyl or benzoyl group; (g) aromatic hydroxy acids comprising benzene or naphthalene and one to three hydroxy groups; (h)
  • thermoplastic light-transforming copolymer composition as described above, wherein the ⁇ -diketone is defined by at least one compound comprising a compound of the generic of R 1 C(O)CH 2 C(0)R 2 , wherein R 1 and R 2 represents residues selected from: (a) linear or branched alkyl substances comprising Ci to C 18 hydrocarbon chains; (b) perfluoroalkyl substances comprising Ci to C 4 hydrocarbon chains; (c) unsubstituted phenyl substances comprising one to five halogen atoms and/or one to five alkyl or alkoxyl groups comprising C ⁇ to C 18 hydrocarbon chain; (d) perfluoroalkyl substances comprising Ci to C 4 hydrocarbon chains; (e) polynuclear aromatic compounds selected from the group of 1 -naphtyl, 2-naphtyl, 9-anthracenyl, 9-phenantrenyl, 2-thenoyl, wherein said
  • thermoplastic light-transforming copolymer composition as described above, wherein the heterocycles comprising nitrogen and selected from the group of pyrazoline, pyridine, quinoline, isoquinoline, quinoxaline, cinnoline, benzoquinoline, either unsubstituted or containing one to three methyl groups; a 2,2'- bipyridine or 4,4' -bipyridine, 2,2'-dipyrazoline, 2,2'-dypyrimidine, 3,3'-dipyridazine, 2,2'-diquinoline, 1,1'- diisoquinoline or 3,3'-diisoquinoline, 4,5-diazofluorene, 1,10-phenanthroline, 2,2':6',2"-terpyridine, 2,4,6-tri(2-pyridyl)-l,3,5-triazine, 1.8-naphtyridine,
  • 1,4,5,8-tetraazaphenantrene and their derivatives either unsubstituted or containing one or two halogen atoms, nitro, amino, hydroxy, methyl, metoxy, and/or phenyl groups.
  • thermoplastic light-transforming copolymer composition as described above, wherein said heterocycles comprising nitrogen and/or oxygenes is comprising any member of the group of macrocyclic crown-ether compounds or their nitrous analogs, 15-crown-5, benzo-15-crown-5, 18-crown-6, dibenzo-18-crown-6, dicyclohexano-18-crown-6, 2,2,1-cryptands and 2,2,2-cryptands, cyclene, cyclame, dioxycyclame, hexacyclene, either unsubstituted or containing 1 to 4 acetic acid residues at nitrogen or carbon atoms.
  • said heterocycles comprising nitrogen and/or oxygenes is comprising any member of the group of macrocyclic crown-ether compounds or their nitrous analogs, 15-crown-5, benzo-15-crown-5, 18-crown-6, dibenzo-18-crown-6, dicyclohexano-18-crown-6, 2,2,1
  • thermoplastic light-transforming copolymer composition as described above, wherein said organic amines, phosphides, or sulfide oxides comprising at least one of the group of pyridine N-oxide derivatives, either unsubstituted or containing one to three methyl groups; quinoline N-oxide, either unsubstituted or containing one to two methyl groups; benzoquinoline N-oxide, 2,2 '-bipyridine N-oxide, 1,10-phenanthroline N-oxide, 2,2' -bipyridine N,N' -oxide, 1,10-phenanthroline N,N'-oxide; a trialkyl(aryl)phosphine P-oxide series compound comprising C to C 8 alkyl chains and/or phenyl group, either unsubstituted or comprising Ci to C 4 , alkyl chains or substances comprising to C alkoxyl chains, or pentafluoropheny
  • thermoplastic light-transforming copolymer composition as described above, wherein said salts of organic acid and alkali or alkaline-earth metals and/or ammonium and/or free amine, comprising C 4 to C 18 carbohydrate chains, and organic acid salt of Li + , Na + , K + , Mg + , Ca 2+ , NH 4 + , R'NHS*, R 1 R 2 NH 2 + , R 1 R 2 R 3 NH , or R ! R 2 R 3 R 4 N + , wherein R 1 - R 4 are C 4 to C 18 alkyl chains or benzyl substances.
  • thermoplastic light-transforming copolymer composition as described above, wherein said free amine comprising at least one substances defined by at least one of the generic formulas RNH 2 + , R l R 2 NR or R ! R 2 R 3 N, wherein R 1 - R 3 are C to C 18 alkyl chains or benzyl substances.
  • thermoplastic copolymer in another preferred embodiment of the present patent is a method for the production of said thermoplastic copolymer, comprising (a) mechanically admixing sufficient amount of said ingredients at room temperature with thermoplastic polymer, preferably in form of granules or powder; (b) extruding said mixture or optionally (c) pressure die-casting of said mixture.
  • thermoplastic copolymer in another preferred embodiment of the present patent is a method for the production of said thermoplastic copolymer, comprising the following subsequent stages (a) admixing an efficient amount of said ingredients and (b) extruding and granulating the obtained concentrate, comprising up to 20 % of said admixture; (c) diluting obtained material with the initial thermoplastic polymer to an efficient concentration.
  • thermoplastic light-transforming copolymer composition presented in the present invention is preferably used as a light-transforming polymer composition that effectively prevent transmission of UV-radiation by means it shifting said UV radiation into red spectral region and exhibits luminescence predominantly in the red spectrum range.
  • Said composition is preferably used as a matrix-forming agent, comprising but not limited to a polymer, film, fiber, a glass-forming composition or a lacquer-forming or adhesive-forming for various purposes, comprising conservatories, hothouses, hotbeds, and greenhouses and other agriculture uses, in the form of roofing blocks for exhibition and recreation premises (e.g., dancing halls) in the form blocks or arbitrarily-shaped parts for the production of furniture, decorative articles, etc.
  • a matrix-forming agent comprising but not limited to a polymer, film, fiber, a glass-forming composition or a lacquer-forming or adhesive-forming for various purposes, comprising conservatories, hothouses, hotbeds, and greenhouses and other agriculture uses, in the form of roofing blocks for
  • the invention is illustrated by the following examples.
  • the light stability of materials produced was measured using results of accelerated tests performed on an Atlas (USA) Xenotest 150S instrument.
  • the relative light stability data of compositions produced are given in Table 1.
  • Active admixture components europium and yttrium chlorides hexahydrates in the concentration ratio of 1 :1 (A), thinoyl trifluoroacetone (B), tri- «-octyl phosphine oxide (C), and sodium palmitate (D) are taken in the mass ratio of 1:1.82:2.11:2.29 and mechanically mixed at room temperature with polyethylene granules, the total admixture weight content of the mixture being 0.3 %. This composition is extruded to produce a film 100 ⁇ m thick.
  • Active admixture components europium and yttrium acetates in the concentration ratio of 1:5 (A), 4-benzoyl-3 -methyl- 1 -phenyl -2-pyrazoline-5 -on (B), 1,10-phenanthroline (C), and 1,10-hexadecyl amine (D) are taken in the mass ratio of 1:2.53:0.55:2.2 and mechanically mixed with ethylene - vinyl acetate copolymer granules, the total admixture weight content of the mixture being 10 %.
  • This composition is extruded to produce concentrate which is diluted 100-fold with the initial copolymer and hot-rolled into sheets 500 ⁇ m thick.
  • Active admixture components thenoyl trifluoroacetone (B), 2,2'-dipyridine (C), and calcium stearate (D) are taken in the mass ratio of 1:0.23:1.23 and mechanically mixed with nylon- 12 granules, the total admixture weight content of the mixture being 6 %.
  • the composition produced is extruded into metal-free concentrate granules.
  • europium and yttrium nitrate hexahydrates in the concentration ratio of 1 : 50 (A) are mechanically mixed with metal-free concentrate and initial polymer granules, the concentrate to polymer mass ratio being 1 :20.
  • the europium and yttrium salts mixture (A) to thenoyl trifluoroacetone (B) mass ratio is 1:1.5.
  • the resulting composition is extruded through filament devices to produce polymer filament.
  • Active admixture components (B) and (C) taken in the same ratio as in example 3, but without calcium stearate (D), are extruded together with nylon- 12 granules into metal-free concentrate granules in the same manner as above and further processed along with component A and initial polymer granules into polymer filament, the mass ratio of components being the same as in example 3.
  • Active admixture components europium and yttrium chloride hexahydrates in the concentration ratio of 1:5 (A), dibenzoyl methane (Bi), thenoyl trifluoroacetone (B 2 ), 2,2'-dipyridine (CO, 1,10-phenanthroline (C 2 ), and tribenzyl amine (D) are taken in the mass ratio of 1:0.91:0.92:0.21:0.25:2.35 and mechanically mixed with polystyrene granules, the total admixture weight content of the mixture being 0.1 %. This composition is extruded to produce formed casts.
  • Active admixture components europium and yttrium nitrate pentahydrates in the concentration ratio of 1:10 (A), thenoyl trifluoroacetone (B), 2,2'-dipyridine (CO, dibenzo-18-crown-6 (C 2 ), and N,N' -dimethyl octadecyl amine (D) are taken in the mass ratio of 1 :1.8:1.5:0.4:0.8:3 and mechanically mixed at room temperature with polyethylene granules, the total admixture weight content of the mixture being 0.5 %. This composition is extruded to produce a film 150 ⁇ m thick.
  • Active admixture components europium and yttrium acetate hydrates in the concentration ratio of 1:50 (A), dibenzoyl methane (B), 1,10-phenanthroline N-oxide (C), ammonium stearate (DO, and dioctyl sulfoxide (D 2 ) are taken in the mass ratio of 1:2:0.6:4:0.5 and mechanically mixed with ethylene - propylene copolymer granules, the total admixture weight content of the mixture being 0.4 %.
  • This composition is processed by extrusion stretch-blow molding into film 50 ⁇ m thick.
  • Active admixture components (A), (B), (C), (DO, (D 2 ) taken in the same ratio as in example 6, but with europium acetate hydrate taken as component (A) are processed in the same way with ethylene - propylene copolymer granules into film 50 ⁇ m thick.

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Abstract

L'invention concerne une composition copolymère thermoplastique transformant la lumière et servant à changer un rayonnement ultraviolet de source solaire ou d'une autre source de rayonnement ultraviolet en zone spectrale rouge, cette composition comprenant 0.001 - 5 % (en poids) de chacun des groupes constitutifs suivants dans une matrice polymère continue: (a) des sels organiques et/ou inorganiques contenant au moins un élément europium ou yttrium; (b) au moins une substance bêta-dicétone; (c) une substance sélectionnée dans le groupe d'hétérocycles comprenant azote ou oxygène, amines organiques, phosphures ou sulfures-oxydes; (d) une substance sélectionnée dans le groupe constitué par des sels d'acide organique et de métaux alcalins ou alcalino-terreux et/ou d'ammonium et/ou d'amine libre. La présente invention porte également sur un procédé pour produire une composition copolymère thermoplastique transformant la lumière.
PCT/IL2002/000993 2002-12-10 2002-12-10 Composition copolymere thermoplastique transformant la lumiere et servant a changer un rayonnement ultraviolet en zone spectrale rouge et procede de production associe WO2004052979A1 (fr)

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PCT/IL2002/000993 WO2004052979A1 (fr) 2002-12-10 2002-12-10 Composition copolymere thermoplastique transformant la lumiere et servant a changer un rayonnement ultraviolet en zone spectrale rouge et procede de production associe
AU2002358954A AU2002358954A1 (en) 2002-12-10 2002-12-10 A thermoplastic light-transforming copolymer composition useful for shifting of ultraviolet radiation into red spectral region and a method for production thereof

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PCT/IL2002/000993 WO2004052979A1 (fr) 2002-12-10 2002-12-10 Composition copolymere thermoplastique transformant la lumiere et servant a changer un rayonnement ultraviolet en zone spectrale rouge et procede de production associe

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Cited By (4)

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WO2008148792A1 (fr) * 2007-06-06 2008-12-11 Institut National Des Sciences Appliquees De Rennes Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables
EP2080785A1 (fr) * 2006-10-18 2009-07-22 Sanvic Inc. Composition de résine fluorescente et module de batterie solaire utilisant ladite composition
KR100983602B1 (ko) 2008-09-05 2010-09-27 주식회사 엔비오 광 변환 농업용 그린하우스 필름을 제조하기 위한 고분자 조성물과 이를 이용한 그린하우스 필름의 제조방법과 그 그린하우스 필름
CN114516885A (zh) * 2021-12-23 2022-05-20 中国农业科学院农业环境与可持续发展研究所 一种用于转光膜的光转换剂及其制备方法

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DATABASE WPI Section Ch Week 199628, Derwent World Patents Index; Class A17, AN 1996-275880, XP002252560 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2080785A1 (fr) * 2006-10-18 2009-07-22 Sanvic Inc. Composition de résine fluorescente et module de batterie solaire utilisant ladite composition
EP2080785A4 (fr) * 2006-10-18 2009-09-30 Sanvic Inc Composition de résine fluorescente et module de batterie solaire utilisant ladite composition
US8222335B2 (en) 2006-10-18 2012-07-17 Sanvic Inc. Fluorescent resin composition and solar battery module using the same
WO2008148792A1 (fr) * 2007-06-06 2008-12-11 Institut National Des Sciences Appliquees De Rennes Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables
FR2917226A1 (fr) * 2007-06-06 2008-12-12 Inst Nat Sciences Appliq Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables
US9127139B2 (en) 2007-06-06 2015-09-08 Institut National Des Sciences Appliquees De Rennes Process for labeling materials based on organic thermoplastic or thermosetting polymer matrices
KR100983602B1 (ko) 2008-09-05 2010-09-27 주식회사 엔비오 광 변환 농업용 그린하우스 필름을 제조하기 위한 고분자 조성물과 이를 이용한 그린하우스 필름의 제조방법과 그 그린하우스 필름
CN114516885A (zh) * 2021-12-23 2022-05-20 中国农业科学院农业环境与可持续发展研究所 一种用于转光膜的光转换剂及其制备方法

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