WO2013046846A1 - Procédé pour la production de polymère contenant du propylène chloré - Google Patents

Procédé pour la production de polymère contenant du propylène chloré Download PDF

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Publication number
WO2013046846A1
WO2013046846A1 PCT/JP2012/067169 JP2012067169W WO2013046846A1 WO 2013046846 A1 WO2013046846 A1 WO 2013046846A1 JP 2012067169 W JP2012067169 W JP 2012067169W WO 2013046846 A1 WO2013046846 A1 WO 2013046846A1
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WIPO (PCT)
Prior art keywords
propylene
containing polymer
chloroform
chlorinated
water
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PCT/JP2012/067169
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English (en)
Japanese (ja)
Inventor
賢一郎 磯本
Original Assignee
東洋紡株式会社
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Publication date
Application filed by 東洋紡株式会社 filed Critical 東洋紡株式会社
Priority to CN201280003487.8A priority Critical patent/CN103189399B/zh
Priority to KR1020137009030A priority patent/KR101380019B1/ko
Publication of WO2013046846A1 publication Critical patent/WO2013046846A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation
    • C08F8/22—Halogenation by reaction with free halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/04—Monomers containing three or four carbon atoms
    • C08F10/06—Propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen

Definitions

  • the present invention relates to a method for producing a chlorinated propylene-containing polymer.
  • chlorinated propylene-containing polymers are chlorinated polypropylene and chlorinated propylene- ⁇ -olefin copolymers, which are paints, inks and adhesives as adhesion-imparting components (binder components) for polypropylene substrates. Widely used in applications such as agents.
  • a chlorination method of a propylene-containing polymer for example, polypropylene
  • 1) a method of chlorinating polypropylene in a solid phase 2) a method of suspending polypropylene in water and chlorinating, 3) chlorination of polypropylene
  • a system solvent for example, chloroform
  • 4) methods for chlorination by dispersing and dissolving polypropylene in a mixture of a chlorinated solvent (for example, chloroform) and water are known methods for chlorination by dispersing and dissolving polypropylene in a mixture of a chlorinated solvent (for example, chloroform) and water.
  • the chlorination methods in the solid phase or suspension in water listed in 1) and 2) above cannot secure a large chlorine content because only the surface layer of polypropylene is chlorinated.
  • the chlorination site tends to be biased, and if a highly crystalline portion remains on the polypropylene surface, the solubility in the solvent tends to be insufficient even after chlorination.
  • a radical generator for example, ultraviolet rays, organic peroxides, azo compounds, etc.
  • the accompanying device, temperature management, pressure management, etc. are indispensable. Specifically, a dedicated device is required for ultraviolet irradiation.
  • temperature control in consideration of the half-life temperature is necessary, and it is necessary to add continuously or intermittently until chlorine gas is thermally decomposed.
  • pressure management is necessary in that it is necessary to release hydrogen chloride gas produced as a by-product outside the system, and the chlorine utilization rate must be low in that chlorine is released out of the system as chlorine hydrogen gas. Absent.
  • Chlorination using a mixture of chlorinated solvent and water listed in 4) above is easy to ensure a large amount of chlorine, but when phase separation into a hydrochloric acid phase and a chlorinated solvent phase after the chlorination reaction, There is a problem in that the polarity of the resin in the chlorinated solvent is high and a long time is required for phase separation. Examples of chlorination using a mixed liquid of this chlorinated solvent and water are described in Patent Documents 1 and 2, for example.
  • the chlorination method 4) is preferable in that the chlorination site is less likely to be biased and a large amount of chlorine can be easily secured. Therefore, in the chlorination method of 4), there has been developed a method for efficiently producing a chlorinated propylene-containing polymer by phase-separating the hydrochloric acid phase and the chlorinated solvent phase in a short time after the chlorination reaction. It is desired.
  • the present invention is a method for producing a chlorinated propylene-containing polymer having a step of chlorinating a propylene-containing polymer in a mixed solution of a chlorinated solvent and water.
  • the object is to provide an improved production method which can be obtained.
  • the present inventor has found that the above object can be achieved when a production method having a specific process is adopted, and has completed the present invention.
  • this invention relates to the manufacturing method of the following chlorinated propylene containing polymer.
  • a method for producing a chlorinated propylene-containing polymer comprising: (1) Step 1 of obtaining a dispersion by dispersing at least one propylene-containing polymer of polypropylene and a propylene- ⁇ -olefin copolymer in a mixed solution containing chloroform and water; (2) Step 2 of chlorinating the propylene-containing polymer by introducing chlorine gas into the dispersion while heating the dispersion at a temperature of 130 ° C.
  • the method for producing the chlorinated propylene-containing polymer of the present invention comprises: (1) Step 1 of obtaining a dispersion by dispersing at least one propylene-containing polymer of polypropylene and a propylene- ⁇ -olefin copolymer in a mixed solution containing chloroform and water; (2) Step 2 of chlorinating the propylene-containing polymer by introducing chlorine gas into the dispersion while heating the dispersion at a temperature of 130 ° C.
  • the method has a step 4 of obtaining a chlorinated propylene-containing polymer.
  • the reaction solution is converted into a hydrochloric acid-containing phase and a chloroform-containing phase by adding a water-insoluble epoxy group-containing compound to the reaction solution obtained in step 2.
  • Phase separation can be performed in a short time, and as a result, the chlorinated propylene-containing polymer as the target product can be produced efficiently.
  • step 1 At least one propylene-containing polymer of polypropylene and a propylene- ⁇ -olefin copolymer is dispersed in a mixed solution containing chloroform and water to obtain a dispersion.
  • the raw material propylene-containing polymer at least one of polypropylene and a propylene- ⁇ -olefin copolymer is used.
  • the propylene- ⁇ -olefin copolymer is a copolymer in which ⁇ -olefin is copolymerized mainly with propylene.
  • ⁇ -olefin for example, one kind or several kinds of ethylene, 1-butene, 1-heptene, 1-octene, 4-methyl-1-pentene and the like can be used. Of these ⁇ -olefins, ethylene and 1-butene are preferred.
  • the ratio of the propylene component to the ⁇ -olefin component of the propylene- ⁇ -olefin copolymer is not limited, but the propylene component is preferably 50 mol% or more, and more preferably 90 mol% or more.
  • Both the polypropylene and the propylene- ⁇ -olefin copolymer are preferably isotactic polymers.
  • Isotactic polymers exhibit a relatively high degree of crystallinity, and crystallinity can be controlled by chlorination.
  • the propylene-containing polymer is provided with solubility in various organic solvents, it can be crystallized by increasing the chlorine content.
  • the solubility in an organic solvent is lowered, but high crystallinity can be maintained by setting the chlorine content low.
  • Polypropylene and propylene- ⁇ -olefin copolymers synthesized using a metallocene catalyst are preferred because they have uniform crystallinity and excellent solubility in solvents.
  • the polypropylene and the propylene- ⁇ -olefin copolymer commercially available products can be used.
  • the propylene-containing polymer is dispersed in a mixed liquid containing chloroform and water to obtain a dispersion.
  • the main purpose of use of water is to absorb the hydrogen chloride produced as a by-product during the chlorination in Step 2 and to simplify the production process of the target product.
  • it may be set according to the amount, it is preferably set so that the hydrochloric acid concentration in the hydrochloric acid phase after the completion of the reaction is 10 to 30%.
  • the weight ratio of the propylene-containing polymer, chloroform, and water in the dispersion is not limited, but is preferably 1: 8 to 20: 0.8 to 2, and 1: 9 to 15: 0. 9 to 1.8 is more preferable.
  • step 2 the propylene-containing polymer is chlorinated by introducing chlorine gas into the dispersion while heating the dispersion at a temperature of 130 ° C. or lower in a sealed state.
  • the dispersion is heated at a temperature of 130 ° C. or lower under hermetic conditions.
  • the temperature is not limited as long as it is within the above range, but the maximum temperature reached during chlorination is preferably 110 to 130 ° C, more preferably 115 to 125 ° C, from the viewpoint of securing a temperature at which the propylene-containing polymer is dissolved.
  • the dispersion liquid contains water
  • introduction of chlorine continuously generates oxygen radicals (O.) in the reaction system by the following reaction.
  • the containing polymer can be chlorinated.
  • hypochlorous acid is first produced by the reaction of water or hydroxide ions with chlorine, and then oxygen radicals are produced by the decomposition of hypochlorous acid.
  • the amount of chlorine gas introduced is not limited, but the chlorine content of the chlorinated propylene-containing polymer is preferably 20 to 40% by weight.
  • the chlorine content is not limited to such a range, but in the present invention, it is preferably 20 to 40% by weight, more preferably 25 to 35% by weight.
  • Hydrogen chloride is by-produced by the introduction of chlorine gas, but since most of the hydrogen chloride is dissolved in water, excessive pressure control or the like is not necessary in the production method of the present invention. Further, since chlorination is performed in a hermetically sealed state, it is preferable in that a large chlorine utilization rate can be secured as compared with the conventional non-aqueous chlorination.
  • the weight average molecular weight of the chlorinated propylene-containing polymer obtained by the production method of the present invention is not limited, but is preferably 5000 to 200000. If it is less than 5000, the cohesive force becomes weak and the adhesion to the polypropylene substrate may be poor. On the other hand, when it exceeds 200,000, the dissolved state in the solvent may deteriorate. A more preferred weight average molecular weight is 30,000 to 180,000.
  • oxygen gas may be introduced prior to introduction of chlorine gas in order to reduce the weight average molecular weight of the chlorinated propylene-containing polymer. By introducing oxygen gas, oxygen radicals are generated and molecular cleavage of the propylene-containing polymer occurs, whereby the weight average molecular weight can be adjusted to be smaller.
  • step 3 a water-insoluble epoxy group-containing compound is added to the reaction solution obtained in step 2 and allowed to stand, and then the chloroform-containing phase is collected.
  • Water-insoluble means that the solubility in water at 20 ° C. is less than 1% by weight.
  • the reaction solution can be separated into a hydrochloric acid-containing phase and a chloroform-containing phase in a short time by adding a water-insoluble epoxy group-containing compound to the reaction solution obtained in step 2 and allowing to stand.
  • the water-insoluble epoxy group-containing compound preferably has an action of aggregating fine water particles in the reaction solution (action as an emulsion breaker).
  • phenyl glycidyl ether examples include monoepoxy compounds such as -butylphenyl glycidyl ether, 4-chlorophenyl glycidyl ether, 4-methoxyphenyl glycidyl ether, 2-biphenyl glycidyl ether, 1-naphthyl glycidyl ether, 2-ethylhexyl glycidyl ether, and allyl glycidyl ether.
  • monoepoxy compounds such as -butylphenyl glycidyl ether, 4-chlorophenyl glycidyl ether, 4-methoxyphenyl glycidyl ether, 2-biphenyl glycidyl ether, 1-naphthyl glycidyl ether, 2-ethylhexyl glycidyl ether, and allyl glycidyl ether
  • bisphenol A type epoxy compounds obtained by polycondensation reaction of bisphenol A and epichlorohydrin in various proportions bisphenol F type epoxy compounds obtained by polycondensation reaction of bisphenol F and epichlorohydrin in various proportions, unsaturated Examples thereof include epoxidized soybean oil and epoxidized linseed oil obtained by reacting a vegetable oil having a group with a peracid such as peracetic acid.
  • polyfunctional epoxy compounds such as hydrogenated bisphenol A diglycidyl ether, diglycidyl o-phthalate, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether and the like are also exemplified.
  • the addition amount of the water-insoluble epoxy group-containing compound is not limited, but is preferably 0.1 to 5 parts by weight, preferably 0.3 to 2 parts per 100 parts by weight of the chlorinated propylene-containing polymer in the reaction solution. Part by weight is more preferred.
  • the standing time after the addition of the epoxy group-containing compound is not limited as long as the phase separation can be sufficiently performed. In the present invention, it is preferably 2 hours or less, and more preferably 1 hour or less. As described above, in the present invention, since the phase separation can be performed in a significantly short time as compared with the conventional production method, the target product can be produced efficiently.
  • the chloroform-containing layer is collected.
  • the chloroform-containing phase contains a chlorinated propylene-containing polymer, and a known fractionation method can be used as the fractionation method.
  • Step 4 obtains a chlorinated propylene-containing polymer by distilling off chloroform from the chloroform-containing phase.
  • the temperature and pressure conditions for distilling off the chloroform from the chloroform-containing phase are not limited, but it is preferable in terms of efficiency to gradually reduce the pressure from the state above the boiling point (61 ° C.) of chloroform. 70 ° C. is preferable, and 25 to 65 ° C. is more preferable.
  • the pressure condition is preferably ⁇ 0.09 to 0.08 MPa, more preferably ⁇ 0.08 to 0.05 MPa. Further, in the present invention, most of chloroform is distilled off under reduced pressure, and then a high concentration solution of a chlorinated propylene-containing polymer is fed to an extruder and chlorinated while distilling off residual chloroform. It is preferable to granulate and take out the propylene-containing polymer.
  • the temperature condition and pressure condition at the time of extrusion are not limited, but feeding from a high temperature and low vacuum state gradually to a low temperature and high vacuum state is preferable in terms of the efficiency of the production method, and the extruder temperature is preferably 50 to 150 ° C. More preferred is ⁇ 140 ° C.
  • the extruder pressure condition is preferably ⁇ 0.099 to ⁇ 0.080 MPa, more preferably ⁇ 0.099 to ⁇ 0.090 MPa.
  • the chlorinated propylene-containing polymer obtained through the above process is easily dissolved in various solvents such as toluene, xylene, solvent naphtha, etc., and is used as a component for imparting adhesion to a polypropylene substrate, such as paint, ink, adhesive, etc. Can be used widely.
  • the production method of the present invention adds the water-insoluble epoxy group-containing compound to the reaction solution obtained in Step 2 in Step 3, so that the reaction solution can be phased into a hydrochloric acid-containing phase and a chloroform-containing phase in a short time. As a result, the target chlorinated propylene-containing polymer can be efficiently produced.
  • Example 1 In a 5000 L glass-lined reactor, 300 kg of isotactic polypropylene (MFR 14 g / min at 230 ° C., melting point 165 ° C.) 300 kg synthesized using Ziegler-Natta catalyst, 3100 kg of chloroform and 420 kg of deionized water were sealed. .
  • chloroform was distilled off and the chlorinated polypropylene solution having a high concentration was fed to a twin-screw extruder at 30 to 50 ° C., and the heating temperature was 60 to 140 ° C. and the degree of vacuum was ⁇ 0.099 to ⁇ 0.093 MPa. Under reduced pressure, chloroform was distilled off and granulated.
  • the obtained chlorinated polypropylene had a chlorine content of 30.2% and a weight average molecular weight of 180,000.
  • Example 2 In Example 1, the same operation as in Example 1 was performed except that 0.2 kg of oxygen gas was introduced before chlorine was introduced.
  • the obtained chlorinated polypropylene had a chlorine content of 30.1% and a weight average molecular weight of 140,000.
  • propylene: ethylene 97: 3 molar ratio, MFR 2 g / min, melting point 125 ° C.
  • Example 4 In Example 3, the same operation as in Example 3 was performed except that the amount of deionized water used was 540 kg, and 440 kg of chlorine gas was introduced over 5 hours and 30 minutes.
  • the obtained chlorinated polypropylene had a chlorine content of 39.7% and a weight average molecular weight of 106,000.
  • Example 5 In Example 3, the same operation as in Example 3 was performed except that the amount of deionized water used was 270 kg, and 157 kg of chlorine gas was introduced over 2 hours.
  • the obtained chlorinated polypropylene had a chlorine content of 20.4% and a weight average molecular weight of 92,000.
  • Example 6 In Example 1, the same operation as in Example 1 was performed except that 3 kg of oxygen gas was introduced before introducing chlorine.
  • the obtained chlorinated polypropylene had a chlorine content of 30.3% and a weight average molecular weight of 70,000.
  • Example 7 Example 1 except that 1.8 kg of p-tert-butylphenylglycidyl ether (epoxy equivalent 225 g / eq) was added instead of 1.8 kg of bisphenol A type epoxy compound (epoxy equivalent 189 g / eq) in Example 1. The same operation as 1 was performed. After standing for 1 hour, as in Example 1, the phase was clearly separated into an upper hydrochloric acid phase and a lower chloroform-containing phase. The obtained chlorinated polypropylene had a chlorine content of 30.1% and a weight average molecular weight of 176,000.
  • Example 8 Example 1 is the same as Example 1 except that 1.8 kg of trimethylolpropane triglycidyl ether (epoxy equivalent 150 g / eq) was added instead of 1.8 kg of bisphenol A type epoxy compound (epoxy equivalent 189 g / eq). The same operation was performed. After standing for 1 hour, as in Example 1, the phase was clearly separated into an upper hydrochloric acid phase and a lower chloroform-containing phase. The obtained chlorinated polypropylene had a chlorine content of 30.3% and a weight average molecular weight of 178,000.
  • Example 1 In Example 1, no bisphenol A type epoxy compound (epoxy equivalent 189 g / eq) was added after introduction of chlorine gas. As a result, the mixture was allowed to stand in the same manner as in Example 1, and separation of the hydrochloric acid layer and the chloroform layer was attempted.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention porte sur un procédé pour la production d'un polymère contenant du propylène chloré, ledit procédé comprenant une étape dans laquelle un polymère contenant du propylène est chloré dans un liquide mélangé constitué d'un solvant à base de chlore et d'eau. Ce procédé est un procédé de production amélioré par lequel un objet produit peut être obtenu plus efficacement que par des procédés classiques. Précisément, la présente invention porte sur un procédé pour la production d'un polymère contenant du propylène chloré, qui est caractérisé en ce qu'il comprend : (1) une étape 1 dans laquelle une dispersion liquide est obtenue par dispersion d'au moins une sorte de polymère contenant du propylène choisi parmi les polypropylènes et les copolymères de propylène-α-oléfine dans un liquide mélangé qui contient du chloroforme et de l'eau; (2) une étape 2 dans laquelle le polymère contenant du propylène est chloré par introduction d'un gaz contenant du chlore dans la dispersion liquide, alors que la dispersion liquide est chauffé à une température inférieure ou égale à 130°C dans un système fermé; (3) une étape 3 dans laquelle une phase contenant du chloroforme est séparée après avoir ajouté un composé contenant des groupes époxy insoluble dans l'eau dans le liquide réactionnel obtenu dans l'étape 2 et après avoir laissé le liquide ainsi obtenu au repos; et (4) une étape 4 dans laquelle un polymère contenant du propylène chloré est obtenu par élimination de chloroforme de la phase contenant du chloroforme par distillation.
PCT/JP2012/067169 2011-09-30 2012-07-05 Procédé pour la production de polymère contenant du propylène chloré WO2013046846A1 (fr)

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Application Number Priority Date Filing Date Title
CN201280003487.8A CN103189399B (zh) 2011-09-30 2012-07-05 氯化的含丙烯聚合物的制造方法
KR1020137009030A KR101380019B1 (ko) 2011-09-30 2012-07-05 염소화된 프로필렌 함유 중합체의 제조 방법

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JP2011217415A JP5229369B2 (ja) 2011-09-30 2011-09-30 塩素化されたプロピレン含有重合体の製造方法
JP2011-217415 2011-09-30

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KR (1) KR101380019B1 (fr)
CN (1) CN103189399B (fr)
TW (1) TWI542607B (fr)
WO (1) WO2013046846A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013121871A1 (fr) * 2012-02-17 2013-08-22 東洋紡株式会社 Composition de polymère contenant du propylène chloré modifiable par oxydation et son procédé de fabrication
CN112279946A (zh) * 2020-10-16 2021-01-29 云南正邦科技有限公司 一种微通道反应制备氯化聚丙烯的方法及产物

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015190411A1 (fr) * 2014-06-11 2015-12-17 東洋紡株式会社 Composition adhésive à base de polyoléfine
CN115232237B (zh) * 2022-06-24 2023-11-03 瑞易德新材料股份有限公司 一种高氯低粘度的氯化聚丙烯的制备方法
CN115651102B (zh) * 2022-11-09 2024-02-06 安徽省化工研究院 一种联产制备氯化聚丙烯的方法

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JPH05230128A (ja) * 1992-02-18 1993-09-07 Toyo Kasei Kogyo Kk 塩素化ポリオレフイン類の製造法
JPH069718A (ja) * 1992-06-26 1994-01-18 Toyo Kasei Kogyo Co Ltd 塩素化ポリオレフイン類の製造法
JP2001114843A (ja) * 1999-10-13 2001-04-24 Nippon Paper Industries Co Ltd 耐溶剤性良好な酸変性塩素化ポリオレフィン
JP2003171597A (ja) * 2001-12-03 2003-06-20 Nippon Paper Industries Co Ltd 熱可塑性飽和ノルボルネン系樹脂用プライマー及びそれを用いた接着方法又は塗工方法
JP2003321588A (ja) * 2001-12-28 2003-11-14 Nippon Paper Industries Co Ltd バインダー樹脂組成物と製造方法及びその用途
WO2005116093A1 (fr) * 2004-05-31 2005-12-08 Nippon Paper Chemicals Co., Ltd. Copolymère statistique de propylène chloré et compositions contenant celui-ci

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Publication number Priority date Publication date Assignee Title
JPH05230128A (ja) * 1992-02-18 1993-09-07 Toyo Kasei Kogyo Kk 塩素化ポリオレフイン類の製造法
JPH069718A (ja) * 1992-06-26 1994-01-18 Toyo Kasei Kogyo Co Ltd 塩素化ポリオレフイン類の製造法
JP2001114843A (ja) * 1999-10-13 2001-04-24 Nippon Paper Industries Co Ltd 耐溶剤性良好な酸変性塩素化ポリオレフィン
JP2003171597A (ja) * 2001-12-03 2003-06-20 Nippon Paper Industries Co Ltd 熱可塑性飽和ノルボルネン系樹脂用プライマー及びそれを用いた接着方法又は塗工方法
JP2003321588A (ja) * 2001-12-28 2003-11-14 Nippon Paper Industries Co Ltd バインダー樹脂組成物と製造方法及びその用途
WO2005116093A1 (fr) * 2004-05-31 2005-12-08 Nippon Paper Chemicals Co., Ltd. Copolymère statistique de propylène chloré et compositions contenant celui-ci

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013121871A1 (fr) * 2012-02-17 2013-08-22 東洋紡株式会社 Composition de polymère contenant du propylène chloré modifiable par oxydation et son procédé de fabrication
CN112279946A (zh) * 2020-10-16 2021-01-29 云南正邦科技有限公司 一种微通道反应制备氯化聚丙烯的方法及产物
CN112279946B (zh) * 2020-10-16 2023-09-08 云南正邦科技有限公司 一种微通道反应制备氯化聚丙烯的方法及产物

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KR101380019B1 (ko) 2014-04-02
CN103189399B (zh) 2014-08-27
TW201319105A (zh) 2013-05-16
JP5229369B2 (ja) 2013-07-03
KR20130072249A (ko) 2013-07-01
CN103189399A (zh) 2013-07-03
JP2013076014A (ja) 2013-04-25
TWI542607B (zh) 2016-07-21

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