WO2001019911A1 - Compositions reticulables de poudres de polyolefines fonctionnalisees - Google Patents
Compositions reticulables de poudres de polyolefines fonctionnalisees Download PDFInfo
- Publication number
- WO2001019911A1 WO2001019911A1 PCT/FR2000/002441 FR0002441W WO0119911A1 WO 2001019911 A1 WO2001019911 A1 WO 2001019911A1 FR 0002441 W FR0002441 W FR 0002441W WO 0119911 A1 WO0119911 A1 WO 0119911A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethylene
- acrylate
- chosen
- copolymers
- meth
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/246—Intercrosslinking of at least two polymers
-
- 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
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- 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
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
-
- 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
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
- C08L23/0884—Epoxide containing esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
Definitions
- Patent FR 2 721 319 describes powder compositions for slush molding based on polypropylene and ethylene-propylene rubber (EPR). The skins obtained do not have good creep resistance.
- the present invention is therefore a crosslinkable composition of functionalized polyolefin powder comprising:
- composition having a particle size between 100 and 400 ⁇ m.
- the unsaturated carboxylic acid anhydride can be chosen, for example, from maleic, itaconic, citraconic, allylsuccinic, cyclohex-4-ene-1, 2-dicarboxylic, 4-methylenecyclohex-4-ene-1, 2-dicarboxylic anhydrides, bicyclo (2,2,1) hept-5-ene-2,3-dicarboxylic acid, and x - methylbicyclo (2,2,1) hept-5-ene-2,2-dicarboxylic acid.
- maleic anhydride is used. It would not be departing from the scope of the invention to replace all or part of the anhydride with an unsaturated carboxylic acid such as for example (meth) acrylic acid.
- polyethylenes to which the unsaturated carboxylic acid anhydride is grafted polyethylene is understood to mean homo- or copolymers.
- alpha-olefins advantageously those having from 3 to 30 carbon atoms
- alpha olefins mention may be made of propylene, 1-butene, 1-pentene, 3-methyl-1-butene, 1-hexene, 4-methyl-1-pentene, 3 -methyl-1-pentene, 1-octene, 1-dececene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1 - eicocene, 1-dococene, 1- tetracocene, 1-hexacocene, 1 - octacocene, and 1-triacontene; these alpha-olefins can be used alone or as a mixture of two or more than two, esters of unsaturated carboxylic acids such as, for example, alkyl (meth) acrylates,
- the polyethylene which may be a mixture of several polymers, comprises at least 50% and preferably 75% (in moles) of ethylene, its density can be between 0.86 and 0.98 g / cm 3 .
- the MFI viscosity index at 190 ° C, 2.16 kg
- LDPE low density polyethylene
- HDPE high density polyethylene
- LLDPE linear low density polyethylene
- VLDPE very low density polyethylene
- copolymers of ethylene and of the unsaturated carboxylic acid anhydride that is to say those in which the unsaturated carboxylic acid anhydride is not grafted
- these are the copolymers of l ethylene, unsaturated carboxylic acid anhydride and optionally another monomer which can be chosen from the comonomers mentioned above for the ethylene copolymers intended to be grafted.
- the ethylene-maleic anhydride and ethylene - alkyl (meth) acrylate - maleic anhydride copolymers are advantageously used. These copolymers comprise from 0.2 to 10% by weight of maleic anhydride, from 0 to 40% and preferably 5 to 40% by weight of alkyl (meth) acrylate. Their MFI is between 20 and 100 (190 ° C - 2.16 kg). The alkyl (meth) acrylates have already been described above. The melting temperature is between 80 and 120 ° C.
- the copolymer (A) is commercially available, it is produced by radical polymerization at a pressure which may be between 200 and 2500 bars, it is sold in the form of granules.
- the copolymer is obtained from the grafting of a homo or copolymer polyethylene as described for (A) except that an epoxide is grafted instead of an anhydride.
- a copolymerization it is also similar to (A) except that an epoxide is used, there may also be other comonomers as in the case of (A).
- the product (B) is advantageously an ethylene / alkyl (meth) acrylate / unsaturated epoxide copolymer.
- it can contain up to 40% by weight of alkyl (meth) acrylate, preferably 5 to 40% and up to 10% by weight of unsaturated epoxide, preferably 0.1 to 8%.
- the epoxide is advantageously glycidyl (meth) acrylate.
- the alkyl (meth) acrylate is chosen from methyl (meth) acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate.
- the amount of alkyl (meth) acrylate is advantageously from 20 to 35%.
- the MFI is advantageously between 5 and 100 (in g / 10 min at 190 ° C. under 2.16 kg), the melting temperature is between 60 and 110 ° C.
- This copolymer can be obtained by radical polymerization of the monomers. The powdering is carried out as for (A).
- - tertiary amines such as dimethyllaurylamine, dimethylstearylamine, N-butylmorpholine, N, N-dimethylcyclohexylamine, benzyldimethylamine, pyridine, dimethylamino-4-pyridine, methyl-1-imidazole, tetramethylethylhydrazine, N, N-dimethylpiperazine, N, N, N ', N'-tetramethyl-l , 6-hexanediamine, a mixture of tertiary amines having from 16 to 18 carbons and known under the name of dimethylsuifamine,
- acids such as polymers such as Lucalen (ethylene terpolymer / butyl acrylate / acrylic acid) - Magnesium salts such as mixtures of 65% stearate salt and 35% palmitate salt.
- polyamine By way of example of polyamine, there may be mentioned: ethylenediamine, propanediamine, butanediamine, pentanediamine, hexanediamine, the isomers of the preceding amines, 1, 2-diaminocyclohexane, 1,4-diaminocyclohexane, diethylenetriamine , triethylenetetramine, tetraethylenepentamine, N-aminoethyl-3-aminopropyltrialkoxysilane, triaminopropyltrialkoxysilane, piperazine, Paminoethylpiperazine, diaminoethylpiperazine, xylylenediamine, isophoronediamine, 3,3'-dimethylocyclin 1,4-diaminobenzanilide.
- Part of the polyamine can be replaced by polyols or amino alcohols such as for example: ethylene glycol, propylene glycol, triethylene glycol, dipropylene glycol, butanediol, neopentyl glycol, cyclohexane-dimethanol, hydroquinone bis -hydroxyl-ether, triethanolamine, methyl-diethanolamine, tripropanolamine, N, N-di (2-hydroxyethyl) -aniline, ethanolamine, diethanolamine, propanolamine, dipropanolamine and N-hydroxyethyl-aniline.
- the zeolites advantageously those having pore diameters between 0.3 and 1.5 nm are used and preferably a zeolite chosen from the following four (the pore diameter is indicated): 0.38 nm designated under the type 4A,
- zeolites 0.44 nm designated as type 5A, 0.8 nm designated as type 10X, 0.84 nm designated as type 13X. All these zeolites are available in a particle size of the order of 20 to 50 ⁇ m.
- the zeolite can be loaded with a catalyst for the reaction of the anhydride and the amine.
- desorption temperatures are given below:
- the crosslinking can be carried out by heating beyond the melting point of (A) or later, the skin being removed from the mold, by diffusion of ambient humidity at a temperature between ambient and softening point of (A).
- the radical initiators can be chosen from peroxides, peracids, peresters, peracetals. They are generally used in an amount of 0.01% to 0.5% by mass relative to the polyolefins to be grafted.
- compositions of the invention can also comprise anti-caking agents such as silica Aérosil R972, fluidifying agents such as ethylene-bistearamide, release agents such as calcium stearate or magnesium stearate and other ingredients such as tackifying resins such as Rlichite R1115 resin.
- anti-caking agents such as silica Aérosil R972
- fluidifying agents such as ethylene-bistearamide
- release agents such as calcium stearate or magnesium stearate
- other ingredients such as tackifying resins such as Rlichite R1115 resin.
- processing stabilizers such as Irgafos 168, DDPP, P-EPQ, TNPP, TPP, PS 800, PS 802, antioxidants such as Irganox 1010, 245, 259, 565, 1035, 1076, 1098, 1135, 1141, 1330, 1425, 3052, 3114, 5057, M1024, mixtures of antioxidants and process stabilizers such as Irganox B225, anti UV agents such as the Tinuvin and Chimassorb range from CIBA.
- processing stabilizers such as Irgafos 168, DDPP, P-EPQ, TNPP, TPP, PS 800, PS 802, antioxidants such as Irganox 1010, 245, 259, 565, 1035, 1076, 1098, 1135, 1141, 1330, 1425, 3052, 3114, 5057, M1024, mixtures of antioxidants and process stabilizers such as Irganox B225, anti UV agents such as the Tinuvin and Chi
- fillers and coloring pigments such as carbon black and Ti ⁇ 2-
- deodorizing agents such as activated carbon: for example 3S, CXV (CECA), undecylenic acid, ethyl undecylenate, calcium undecylenate, zinc undecylenate, cyclodextrin, zeolites such as Flavith and perfumes .
- the skin having been formed by melting the mixture of powders (A) + (B) on the hot mold, the excess of unmelted powder is eliminated, then the crosslinking can be continued or triggered by placing it in an oven at a temperature included between 200 and 350 ° C for a time between 10 s and 10 min. The skin is then separated from the mold after cooling. It is also possible in the second and third embodiment to remove the skin from the mold and then cross-link with moisture.
- compositions of the invention make it possible to obtain skins having a very soft feel, a hardness of less than 90 shore A without the use of liquid plasticizers and having no hot creep.
- these skins have the following characteristics:
- the thickness is between 0.6 and 1.1 mm
- compositions of the products % of acrylate, etc.
- compositions of the powders of the invention are by weight. The following products were used:
- MM carbon black MAGNESIUM STEARATE mixtures of 65% stearate salt and 25% palmitate salt AEROSIL R972 (Degussa) ACTIVE CARBON 3S and CXV (CECA).
- the various constituents above have been reduced to powder with a particle size of 200 ⁇ m by cryogenic grinding.
- Example 5 is black skin and Example 6 is gray skin. These examples have better performance than examples 1 and 4 in terms of abrasion, mechanical properties, toxicity (no dimethylsuifamine), better resistance to thermal aging (antioxidants) and less odor.
- the formulas were then cryogenically ground into a powder with a particle size of 200 ⁇ m, then added to the rapid mixer with 2% magnesium stearate and 0.6% AEROSIL silica. 4. Slush molding
- the mold was treated at 100 ° C with a release agent and baked at 120 ° C for 20 min. (Chem-Trend S.A. Mono Coat MC-708A) and was brought to a temperature of 250-300 ° C in an oven. The mold taken out of the oven was then covered with an excess of powder of the composition used. After approximately 10 s, the unmelted powder is removed by inverting the mold. The mold is then brought back to the oven at 250-300 ° C for 1-5 min. The mold is then cooled in cold water. The skin is then released from the mold.
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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)
- Compositions Of Macromolecular Compounds (AREA)
- Moulding By Coating Moulds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002383478A CA2383478A1 (fr) | 1999-09-10 | 2000-09-05 | Compositions reticulables de poudres de polyolefines fonctionnalisees |
PL00353133A PL353133A1 (en) | 1999-09-10 | 2000-09-05 | Crosslinkable compositions of functionalised polyolefin powders |
JP2001523685A JP2003509560A (ja) | 1999-09-10 | 2000-09-05 | 架橋可能な官能性ポリオレフィン粉末組成物 |
AU72979/00A AU7297900A (en) | 1999-09-10 | 2000-09-05 | Crosslinkable compositions of functionalised polyolefin powders |
EP00960794A EP1228141A1 (fr) | 1999-09-10 | 2000-09-05 | Compositions reticulables de poudres de polyolefines fonctionnalisees |
BR0013682-4A BR0013682A (pt) | 1999-09-10 | 2000-09-05 | Composições reticuláveis de pós de poliolefinas funcionalizadas |
US10/070,555 US6774188B1 (en) | 1999-09-10 | 2000-09-05 | Crosslinkable compositions of functionalized polyolefin powders |
KR1020027003103A KR20020057959A (ko) | 1999-09-10 | 2000-09-05 | 작용화 폴리올레핀 파우더의 가교성 조성물 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9911353A FR2798388B1 (fr) | 1999-09-10 | 1999-09-10 | Compositions reticulables de poudres de polyolefines fonctionnalisees |
FR99/11353 | 1999-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001019911A1 true WO2001019911A1 (fr) | 2001-03-22 |
Family
ID=9549726
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/002441 WO2001019911A1 (fr) | 1999-09-10 | 2000-09-05 | Compositions reticulables de poudres de polyolefines fonctionnalisees |
Country Status (13)
Country | Link |
---|---|
US (1) | US6774188B1 (fr) |
EP (1) | EP1228141A1 (fr) |
JP (1) | JP2003509560A (fr) |
KR (1) | KR20020057959A (fr) |
CN (1) | CN1168771C (fr) |
AU (1) | AU7297900A (fr) |
BR (1) | BR0013682A (fr) |
CA (1) | CA2383478A1 (fr) |
CZ (1) | CZ2002865A3 (fr) |
FR (1) | FR2798388B1 (fr) |
PL (1) | PL353133A1 (fr) |
RU (1) | RU2247753C2 (fr) |
WO (1) | WO2001019911A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004041500A1 (fr) * | 2002-10-31 | 2004-05-21 | E.I. Du Pont De Nemours And Company | Procede de coulage par embuage |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8129450B2 (en) | 2002-12-10 | 2012-03-06 | Cellresin Technologies, Llc | Articles having a polymer grafted cyclodextrin |
US7166671B2 (en) * | 2002-12-10 | 2007-01-23 | Cellresin Technologies, Llc | Grafted cyclodextrin |
DE602005023444D1 (de) | 2004-05-24 | 2010-10-21 | Cellresin Tech Llc | Amphotere gepfropfte barrierematerialien |
EP1916265A1 (fr) * | 2006-10-26 | 2008-04-30 | Sika Technology AG | Procédé de fabrication d'un polymère sous forme d'agrégés solides qui contient des groupes amide et ester. |
US7829628B2 (en) | 2006-11-03 | 2010-11-09 | Polyone Corporation | Colorant concentrates for thermoplastic biofiber composites |
JP6895394B2 (ja) | 2015-06-29 | 2021-06-30 | ダウ グローバル テクノロジーズ エルエルシー | 過酸化物開始剤を用いて架橋ポリオレフィンを作製するための組成物及び方法 |
US11401360B2 (en) * | 2017-12-22 | 2022-08-02 | Sabic Global Technologies B.V. | Process for preparation of amorphous polyolefinic ionomers |
KR20240058869A (ko) * | 2021-09-19 | 2024-05-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 다작용성 에폭시 화합물 또는 옥세탄 화합물을 사용한 무수물 작용화된 중합체의 경화 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4612349A (en) * | 1983-10-28 | 1986-09-16 | Societe Chimique Des Charbonnages S.A. | Process for crosslinking ethylene polymers containing anhydride functions, crosslinkable polymer compositions and the application of these compositions to the coating of substrates |
US5483001A (en) * | 1988-03-30 | 1996-01-09 | Norsolor | Thermoplastic compositions based on ethylene polymer and polyester |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5884719A (ja) * | 1981-11-17 | 1983-05-20 | Asahi Chem Ind Co Ltd | 粉末ポリエチレンの成形方法 |
US5037888A (en) * | 1989-11-09 | 1991-08-06 | Eastman Kodak Company | Thermoplastic elastomeric compositions and method for their preparation |
JPH03166236A (ja) * | 1989-11-24 | 1991-07-18 | Ube Ind Ltd | 発泡ポリオレフィン粉末組成物 |
FR2721319B1 (fr) | 1994-06-17 | 1996-08-30 | Reydel Sa | Composition de poudre élastomère polyoléfinique, son procédé de fabrication, article moulé obtenu par sa mise en Óoeuvre. |
DE59509095D1 (de) * | 1994-10-10 | 2001-04-19 | Atochem Elf Sa | Vernetzungsmittel für polymere mit säureanhydridgruppen |
-
1999
- 1999-09-10 FR FR9911353A patent/FR2798388B1/fr not_active Expired - Fee Related
-
2000
- 2000-09-05 BR BR0013682-4A patent/BR0013682A/pt not_active Application Discontinuation
- 2000-09-05 CN CNB008126984A patent/CN1168771C/zh not_active Expired - Fee Related
- 2000-09-05 US US10/070,555 patent/US6774188B1/en not_active Expired - Fee Related
- 2000-09-05 WO PCT/FR2000/002441 patent/WO2001019911A1/fr active Application Filing
- 2000-09-05 KR KR1020027003103A patent/KR20020057959A/ko active IP Right Grant
- 2000-09-05 JP JP2001523685A patent/JP2003509560A/ja not_active Abandoned
- 2000-09-05 RU RU2002109229/04A patent/RU2247753C2/ru not_active IP Right Cessation
- 2000-09-05 EP EP00960794A patent/EP1228141A1/fr not_active Withdrawn
- 2000-09-05 AU AU72979/00A patent/AU7297900A/en not_active Abandoned
- 2000-09-05 PL PL00353133A patent/PL353133A1/xx not_active Application Discontinuation
- 2000-09-05 CZ CZ2002865A patent/CZ2002865A3/cs unknown
- 2000-09-05 CA CA002383478A patent/CA2383478A1/fr not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4612349A (en) * | 1983-10-28 | 1986-09-16 | Societe Chimique Des Charbonnages S.A. | Process for crosslinking ethylene polymers containing anhydride functions, crosslinkable polymer compositions and the application of these compositions to the coating of substrates |
US5483001A (en) * | 1988-03-30 | 1996-01-09 | Norsolor | Thermoplastic compositions based on ethylene polymer and polyester |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004041500A1 (fr) * | 2002-10-31 | 2004-05-21 | E.I. Du Pont De Nemours And Company | Procede de coulage par embuage |
Also Published As
Publication number | Publication date |
---|---|
CA2383478A1 (fr) | 2001-03-22 |
CN1373790A (zh) | 2002-10-09 |
CN1168771C (zh) | 2004-09-29 |
JP2003509560A (ja) | 2003-03-11 |
FR2798388A1 (fr) | 2001-03-16 |
PL353133A1 (en) | 2003-10-20 |
AU7297900A (en) | 2001-04-17 |
CZ2002865A3 (cs) | 2002-07-17 |
EP1228141A1 (fr) | 2002-08-07 |
BR0013682A (pt) | 2002-05-07 |
RU2247753C2 (ru) | 2005-03-10 |
US6774188B1 (en) | 2004-08-10 |
KR20020057959A (ko) | 2002-07-12 |
FR2798388B1 (fr) | 2006-06-23 |
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