WO2000061686A1 - Adjuvant pour resine synthetique - Google Patents

Adjuvant pour resine synthetique Download PDF

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Publication number
WO2000061686A1
WO2000061686A1 PCT/JP2000/002269 JP0002269W WO0061686A1 WO 2000061686 A1 WO2000061686 A1 WO 2000061686A1 JP 0002269 W JP0002269 W JP 0002269W WO 0061686 A1 WO0061686 A1 WO 0061686A1
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WO
WIPO (PCT)
Prior art keywords
group
fluorine
synthetic resin
carbon atoms
containing compound
Prior art date
Application number
PCT/JP2000/002269
Other languages
English (en)
Japanese (ja)
Inventor
Naoyuki Shimeno
Genichirou Enna
Hiroki Fukuda
Original Assignee
Asahi Glass Company, Limited
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 Asahi Glass Company, Limited filed Critical Asahi Glass Company, Limited
Publication of WO2000061686A1 publication Critical patent/WO2000061686A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • 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
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters

Definitions

  • the present invention relates to a synthetic resin additive. More specifically, when added to agricultural coverings made of synthetic resin film, it suppresses the fogging that occurs on the inner surface of the covering and reduces fog generation near the inner surface. It has the ability to suppress (this ability is called anti-fog property), and has the ability to exert an excellent anti-fog effect over a long period of time (this ability is an anti-fog property). (Referred to as cloudiness persistence)
  • Synthetic resins for example, vinyl chloride resins
  • an anti-fogging agent a type of surfactant. This promotes the flow of water droplets on the inner surface of the covering material (the surface facing the inside of the greenhouse; the same applies hereinafter), increasing the amount of sunlight incident. That is.
  • the present invention has an ability to suppress the occurrence of fog near the inner surface of a covering material when added to an agricultural covering material (fog resistance), and has an excellent anti-fog property.
  • the purpose is to provide a synthetic resin additive having a long-lasting haze.
  • the present invention provides a synthetic resin additive containing a fluorine-containing compound represented by the following formula 1.
  • Equation 1 the symbols in Equation 1 have the following meanings.
  • R a polyfluoroalkyl group having 1 to 22 carbon atoms.
  • Q Alkylene group having 1 to 5 carbon atoms.
  • n 1 to; an integer of L00.
  • A an alkylene group having 2 to 4 carbon atoms, or an aromatic hydrogen group in which at least one hydrogen atom of the alkylene group having 2 to 4 carbon atoms is a monovalent aromatic hydrocarbon group, A group that is substituted with a alkoxy group or a phenoxy group.
  • n is 2 to 100, A may be the same or different.
  • the present invention provides an agriculturally disturbed material comprising a synthetic resin film which contains the above-mentioned fluorine-containing compound and does not contain an antifogging agent.
  • BEST MODE FOR CARRYING OUT THE INVENTION The fluorine-containing compound according to the present invention is represented by the following formula 1.
  • R f in Formula 1 is a polyfluoroalkyl group (hereinafter, referred to as an R f group) having 1 to 22 carbon atoms.
  • the Rf group is a group in which two or more hydrogen atoms in an alkyl group have been replaced by fluorine atoms.
  • the Rf group has 1 to 22 carbon atoms, but preferably 1 to 16 and particularly preferably 6 to 14 carbon atoms.
  • R f number of full Tsu atom in groups, (R f off Tsu number atom groups) / (R f number of hydrogen atoms in A Le key Le group of the same number of carbon atoms that corresponds to the group) XI 0 When expressed as 0 (%), 60% or more is preferable, and 80% or more is particularly preferable.
  • the Rf group may have a straight-chain structure or a branched structure, and a straight-chain structure is particularly preferable. In the case of a branched structure, the branched portion is preferably a short chain having about 1 to 3 carbon atoms, and is preferably present at the terminal of the Rf group.
  • the R f group is a perfluoroalkyl group (hereinafter referred to as an “RF group”), and preferably has a linear structure.
  • the RF group is a group in which substantially all of the hydrogen atoms in the alkyl group have been replaced by fluorine atoms. That is, the R F group is preferably a group represented by F (CF 2 ) m — (m is an integer of 1 to 18). m is preferably from 4 to 16 and particularly preferably from 6 to 14.
  • the Rf group having a linear structure can be obtained by adding tetrafluoroethylene to C 2 F 5 I by a telomerization reaction.
  • the Rf group of the branched structure may be a fluorine-containing monomer such as tetrafluoroethylene or hexafluoropropylene, KF or C Catalysts such as s F It can be obtained by ori- gorization.
  • the fluorine-containing compound may be a mixture of two or more compounds having different numbers of carbon atoms in the Rf group.
  • the carbon number of the R f group is 6 to
  • a mixture mainly containing the fluorine-containing compound of No. 14 and having an average carbon number power of 8 to 10 of the Rf group is particularly preferable.
  • Q in the fluorine-containing compound is an alkylene group having 1, 2, 3, 4 or 5 carbon atoms.
  • the carbon number of Q is preferably 2, 3, or 4, particularly preferably 3 or 4.
  • Fluorine-containing compounds in which Q is an alkylene group having 3 or 4 carbon atoms can be found in various environments, particularly when used as a synthetic resin additive. Even so, it is a compound having excellent chemical stability and heat resistance.
  • Q represents an ethylene group, a trimethylene group, a tetramethylene group, a propylene group (one CH (CH 3) CH 2- ), a butylene group (- CH (CH 3) CH 2 CH 2 -, - CH 2 CH (CH 3) CH 2 -, one CH (CH 3) CH (CH 3) -) Hitoshigakyo up al is Ru.
  • R ′ ′ may be bonded to any of the bonds.
  • N in the fluorine-containing compound is an integer of 1 to 100, preferably an integer of 2 to 50. Even when the fluorine-containing compound of the present invention is a mixture of two or more compounds having different numbers of n, the average value of n is in the range of 1 to 50. Are preferred, especially those in the range of 2 to 30.
  • a in the fluorine-containing compound is a monovalent alkylene group having 2 to 4 carbon atoms or one or more hydrogen atoms of the alkylene group having 2 to 4 carbon atoms.
  • This is a group substituted by an aromatic hydrocarbon group, an alkoxy group or a phenoxy group.
  • One, - CH (CH 2 OR 1 ) CH 2 - such Dogakyo up al is Ru.
  • A has an asymmetric structure (for example, a propylene group), its directionality is not limited.
  • R 1 represents an alkyl group having 1 to 10 carbon atoms, and R 1 is preferably a methyl group, a butyl group, or a 2-ethylhexyl group. .
  • a in the fluorine-containing compound is preferably present in one or two kinds, particularly, in the ethylene group only, the propylene group only, or the ethylene group.
  • (A-O) tl is an oxyalkylene group or a polyoxyalkylene group obtained by subjecting a cyclic ether to a ring-opening addition reaction. is there .
  • cyclic ether a compound containing a 3- to 5-membered cyclic ether group having one oxygen atom in the ring is suitable, and has one 3-membered cyclic ether group.
  • Compounds (monoepoxides) are more preferred.
  • Particularly preferred are alkylenoxysides having 2, 3 or 4 carbon atoms.
  • Cyclic ethers include ethylenoxide, propylene oxide, 1,2—butylene oxide, 2,3—butylene oxide, Isobutylene Oxide, Oxetane, Methyloxenate, Phenyl Dali Syl ether, Tetrahydrofuran, Styrene Oxide And the Alkyl Glycidile Ether.
  • Alkyl glycol ethers include methyl glycidyl ether, butyl dexidyl ether, and 2-ethyl hexyl ether ether. Etc. are listed.
  • Preferred cyclic ethers are ethylenoxide, propylenoxide or tetrahydrofuran. A formed by ring opening of tetrahydrofuran is a tetramethylene group.
  • one or more cyclic ethers are used.
  • two or more cyclic ethers are used, a mixture of two or more cyclic ethers may be used for the reaction, or two or more cyclic ethers may be sequentially used for the reaction. Okay.
  • R in the fluorine-containing compound represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • R is an alkyl group having 1 to 18 carbon atoms
  • a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group are preferred.
  • R is an acyl group having 1 to 18 carbon atoms
  • an acyl group having 1 to 10 carbon atoms is preferable
  • an acyl group having 1 to 6 carbon atoms is particularly preferable.
  • the acyl group may have a functional group such as a carboxyl group.
  • a hydrogen atom or a methyl group is preferable, and particularly, a hydrogen atom is preferable.
  • fluorine-containing compound examples include, but are not limited to, the following compounds. No. It's was, and had us to the following formula compounds, the part you the contact with the R F group is rather good even if even if Tsu Oh straight structure Tsu Oh branched structure, a linear structure is not the good or.
  • the linkage is represented by a block. It can be random or random.
  • the (C 3 H 6 ⁇ ) portion indicates an oxypropylene group and is [CH (CH 3) CH 20 ] or [CH 2 CH (CH 3) ⁇ ].
  • the (C 4 H 8 O) portion indicates that it is a ring-opened product of tetrahydrofuran (CH., CH 2 CH., CH 90 ). ⁇
  • R F CH 2 CH and CH (OH) CH 3 which are isomers of the above compound having 4 carbon atoms
  • a method such as a method in which a predetermined radical initiator is added in a solvent and heated, and the mixture is heated and stirred, and then ethanol is added in response to the radical addition reaction to add ethanol. is there .
  • R F (CH 2) 5 OH synthesis methods Q having a carbon number of 5 to the R F I 4 - substituted hydrogen Chi was added to pen te down one 1 one-ol, iodine with a reducing agent There is a way to get it.
  • cyclic ethers When two or more cyclic ethers are subjected to a ring-opening addition reaction, they may be mixed and reacted, or may be reacted sequentially. When only one kind of cyclic ether is used, two or more kinds of cyclic ethers may be used in the reaction system at the same time or may be gradually added to the reaction system. .
  • Including full Tsu-containing compound is usually a cyclic ether and R f Q ⁇ H
  • a mild reaction such as a ternary catalyst of Na BHN a II 7 may result in a side reaction of HF removal under strong alkaline conditions. It is preferable to use a calcite catalyst or the above-mentioned acid catalyst or metal complex catalyst.
  • a calcite catalyst or the above-mentioned acid catalyst or metal complex catalyst.
  • an acid catalyst if the acidity of the catalyst is too strong, a hydrogen atom bonded to a carbon atom adjacent to the carbon atom to which the fluorine atom in the Rf group is bonded Since there is a possibility that HF is desorbed, a diluting solvent may be used as needed to suppress the HF reaction. Examples of the diluting solvent include ether-based solvents such as glyme, nglyme, triglyme, methyl 1-t-butyl ether, and the like.
  • the reaction temperature at which the ether is added is preferably from 120 to 180 ° C, particularly preferably 0: to 130 ° C.
  • the reaction is preferably performed at a temperature lower than the boiling point of the medium + 20).
  • various properties as a fluorine-containing compound can be adjusted by terminal modification such as esterification and alkylation.
  • Acetic acid, propionic acid, butanoic acid, 2-ethylhexanoic acid (octylic acid) is used as the organic carboxylic acid for esterification.
  • Monovalent carboxylic acids such as, 3,5,5-trimethylethylhexanoic acid (isononanoic acid), oleic acid, and stearic acid; Esters and acid anhydrides of these carboxylic acids and low-boiling alcohols are used.
  • divalent carboxylic acids such as oxalic acid, succinic acid, maleic acid, fumaric acid, and fluoric acid, and carboxylic acid esters, and other Acid anhydrides can also be used.
  • Esterification involves adding these carboxylic acids, carboxylic esters or anhydrides to the hydroxyl-terminated fluorine-containing polyalkylene compounds.
  • No catalyst or presence of trace acid catalysts such as paratoluenesulfonic acid or sulfuric acid, or catalysts such as sodium hydroxide or sodium hydroxide Stir while heating underneath. This is followed by dehydration, deacoll, or by distilling off unreacted acid.
  • Alkylation includes a method of reacting with monohaloalkyl under strong alkaline conditions and a method of using alkylsulfuric acid.
  • a reaction using an alkylating agent such as alkylsulfuric acid is preferred.
  • the fluorine-containing compound thus obtained may be subjected to an acid treatment using sulfuric acid, phosphoric acid, or the like, a synthetic magnesium, an activated clay, an activated carbon, if necessary. It is preferable to purify by adsorption treatment etc.
  • the volumetric efficiency it is preferable that the volume ratio after the addition of the cyclic ether is 80 to 95%, and the present invention is not particularly limited to this.
  • the amount of the fluorine-containing compound to be mixed with the synthetic resin is appropriately determined according to the type of the fluorine-containing compound to be compounded.
  • the compounding amount of the fluorine-containing compound is preferably 500 to 100 parts by mass per 100 parts by mass of the synthetic resin, and particularly preferably 70 to 99 parts by mass.
  • the agricultural covering material of the present invention is a synthetic resin film cap that contains the above-mentioned fluorine-containing compound and does not contain an anti-fogging agent.
  • the fluorine-containing compound of the present invention is added to synthetic resin, which is a material for agricultural covering materials, 100 parts by mass of synthetic resin (however, plasticizer is not included in the calculation) The same shall apply hereinafter.) 0.01 or more by mass is preferable.
  • the upper limit is not strictly limited, but if the amount is too large, bleeding or clouding may occur, so that the upper limit is usually 2.0 mass. Parts or less is sufficient.
  • the compounding amount of the fluorine-containing compound is from 0.02 to 1 per 100 parts by mass of the synthetic resin.
  • the synthetic resin which is the material of the synthetic resin and the agricultural covering material, is not only a thermosetting resin or a thermoplastic resin for mold molding, but also a film-forming thermoplastic synthetic resin. Resin is listed. Specifically, monomers such as vinyl chloride, ethylene, propylene, acrylate ester, and methyl acrylate ester alone may be used. Or copolymers of each other, or one or more of these monomers and another copolymerizable monomer (for example, vinyl acetate, vinyl chloride). Copolymers with styrene, etc.), fluorine-containing resins, polyesters, and polyamides. And those obtained by mixing these polymers.
  • monomers such as vinyl chloride, ethylene, propylene, acrylate ester, and methyl acrylate ester alone may be used. Or copolymers of each other, or one or more of these monomers and another copolymerizable monomer (for example, vinyl acetate, vinyl chloride). Copolymers with sty
  • vinyl chloride resin that is, polyvinyl chloride
  • Polymers containing 50% by mass or more of vinyl chloride polymerized units) and ethylene resins (ie, polyethylene and ethylene polymerized units of 50% by mass) % By mass) is preferred, and polyvinyl chloride is particularly preferred.
  • the synthetic resin of the present invention may contain ordinary various additives, for example, a plasticizer, a lubricant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment dye, a warming improver, and the like. Mix in quantity.
  • the plasticizers include, for example, dioctyl phthalate, bis-2-ethyl hexyl acrylate, dibenzyl phthalate, and diphenyl phthalate. Sodesirirata rate, Jidodesiryu evening rate, Jin
  • Phthalic acid derivatives such as 7 "silyl phthalate, etc., isophthalic acid derivatives such as dioctyl isocyanate, dibutyl radical, octyl phthalate, etc.
  • Adipic acid derivatives such as dibutyl, maleic acid derivatives such as dibutyl maleate, etc., citric acid derivatives such as tributyl citrate, monobutyl itaco Itaconic acid derivatives such as neat, o-an forms such as butylolate, etc., and other triglyceryl phosphates and triglyceryl phosphates And plasticized soybean oil, epoxy resin-based plasticizer and the like.
  • Examples of the above lubricants or heat stabilizers include poly (ethylene oxide), bis (amide), stearic acid, zinc stearate, and stainless steel. Examples include barium phosphate, calcium stearate, and ricinoleate.
  • UV absorber examples include benzotriazole, benzolate, benzophenone, cyanoacrylate, and the like.
  • UV absorbers such as UV-based and phenolic silicate-based UV absorbers .
  • pigments or dyes examples include titanium oxide, silica, ultramarine, fluoric acid and the like.
  • Examples of the above-mentioned warming improver include a hydrorotal site.
  • additives are contained in a usual content, for example, 5 parts by mass or less per 100 parts of the synthetic resin.
  • Synthetic resin used as material In order to mix the fluorinated compound of the present invention and, if necessary, various additives, ordinary compounding and mixing techniques can be used. For example, it can be mixed with a Ribbon Blender, Ban Remixer, Super Mixer, and other compounding machines. It is then filmed.
  • a known method for example, a melt extrusion method, a solution casting method, a calendar method, or the like may be used.
  • the thickness of the synthetic resin fisolem which is a coating material, is preferably from 0.01 to 0.5 mm, particularly preferably from 0.020.2 mm. If it is too thin, the strength will be insufficient, and if it is too thick, it will be used for filming and handling afterwards. Inconveniences, including the work and the work of spreading it in eight us).
  • the synthetic resin additive of the present invention When the synthetic resin additive of the present invention is added to an agricultural coating material, the synthetic resin additive is excellent not only in the effect of suppressing fog generation but also in antifogging properties and antifogging durability. Therefore, the agricultural covering material containing the synthetic resin additive [] agent is useful for institutional cultivation of plants. Examples The following are synthesis examples (Example 16), examples (Example 7 12), and comparisons. The present invention will be described in detail with reference to examples (Examples 13 to 18).
  • the hydroxyl value of the fluorine-containing compound D was 57.4 mg KOH / g.
  • the NMR spectrum of the product—NMR, 19 F-NMR, and 13 C—NMR) showed that F (CF 2 ) 8 (CH 2 ) 30 [CH 2 CH (CH 3 ) 0] n H (however, the average value of n is 8.6).
  • the hydroxyl value of the fluorine-containing compound E was 56.8 mg K ⁇ HZg. Due to the NMR spectrum of the product, F (CF),
  • the experimental greenhouse was assembled on an outdoor temperature-controllable water tank. It was made by stretching a frame with a height of 0.5 m, a width of 0.8 m, and a depth of 0.4 m.
  • the antifogging property and fog generation were evaluated by the following methods. The results are shown in Tables 1 and 2.
  • the test was started in September, and the inside of the film stretched in the experimental greenhouse was observed for 8 months.
  • the antifogging property was evaluated according to the following criteria.
  • Fluorine-containing compound J c 8 F 17 CH 2 CH (OH) CH, 0- (CH 2 CH 2 0) 10 [CH 2 CH (CH 3 ) 0] CH 3 fluorinated compound K: C 9 F 19 CON (CH 3 ) (CH 2 CH 20 ) 12 H Fluorine-containing compound L: C 8 F 17 S0 2 N (CH 3 ) (CH 2 CH 20 ) lo H

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention porte sur des résines synthétiques qui peuvent conférer des propriétés antibuée de longue durée à une couche de surface interne d'une matière de couverture pour usage agricole. L'adjuvant comprend un composé fluor représenté par Rf-Q-O-(A-O)¿n?-R (où R?f¿ représente un groupe polyfluorohydrocarbone aliphatique C¿1-22?; Q représente alkylène C1-5; n représente un entier compris entre 1 et 100; A représente alkylène C2-4; etc.; et R représente hydrogène, un groupe hydrocarbure C1-18, etc.).
PCT/JP2000/002269 1999-04-07 2000-04-07 Adjuvant pour resine synthetique WO2000061686A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10063499 1999-04-07
JP11/100634 1999-04-07

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WO2000061686A1 true WO2000061686A1 (fr) 2000-10-19

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CN (1) CN1204200C (fr)
WO (1) WO2000061686A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010511086A (ja) * 2006-11-30 2010-04-08 ソルヴェイ・ソレクシス・エッセ・ピ・ア ハロポリマー用の添加剤

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201118129A (en) * 2009-11-27 2011-06-01 Stone & Resource Ind R & D Ct Anti-yellowing epoxy resin composition for fixing stone material and its application

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0552063A1 (fr) * 1992-01-17 1993-07-21 Sumitomo Chemical Company, Limited Composition de résine polyoléfin et film à partir de celle-ci
JPH05239230A (ja) * 1992-02-26 1993-09-17 Toho Chem Ind Co Ltd 防霧性に優れた合成樹脂フィルム
JPH05239231A (ja) * 1992-02-26 1993-09-17 Toho Chem Ind Co Ltd 防霧性に優れた合成樹脂フィルム
JPH10226739A (ja) * 1996-12-09 1998-08-25 Achilles Corp 農業用塩化ビニル系樹脂フィルム

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0552063A1 (fr) * 1992-01-17 1993-07-21 Sumitomo Chemical Company, Limited Composition de résine polyoléfin et film à partir de celle-ci
JPH05239230A (ja) * 1992-02-26 1993-09-17 Toho Chem Ind Co Ltd 防霧性に優れた合成樹脂フィルム
JPH05239231A (ja) * 1992-02-26 1993-09-17 Toho Chem Ind Co Ltd 防霧性に優れた合成樹脂フィルム
JPH10226739A (ja) * 1996-12-09 1998-08-25 Achilles Corp 農業用塩化ビニル系樹脂フィルム

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010511086A (ja) * 2006-11-30 2010-04-08 ソルヴェイ・ソレクシス・エッセ・ピ・ア ハロポリマー用の添加剤

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KR20010024970A (ko) 2001-03-26
KR100426416B1 (ko) 2004-04-08
CN1296517A (zh) 2001-05-23
CN1204200C (zh) 2005-06-01

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