WO1990012054A1 - Polypropylene-polyester graft copolymer and production method thereof - Google Patents
Polypropylene-polyester graft copolymer and production method thereof Download PDFInfo
- Publication number
- WO1990012054A1 WO1990012054A1 PCT/US1990/001841 US9001841W WO9012054A1 WO 1990012054 A1 WO1990012054 A1 WO 1990012054A1 US 9001841 W US9001841 W US 9001841W WO 9012054 A1 WO9012054 A1 WO 9012054A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polypropylene
- polyester
- weight
- graft copolymer
- carboxyl group
- Prior art date
Links
Classifications
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/027—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyester or polycarbonate sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
Definitions
- the present invention relates to a polypropylene-polyester graft copolymer which is effective as a compatibilizing agent for both of ingredients in a resin composition comprising a polycarbonate and a polyolefin, in particular, a polypropylene, and a production process for the graft copolymer. More in particular, it relates to a graft copolymer of a polyester having specific intrinsic viscosity and concentration of terminal carboxyl group and a modified polypropylene having a specific melt flow rate (MFR), as well as a production process thereof.
- MFR melt flow rate
- Aromatic polycarbonates have excellent impact resistance, heat resistance, rigidity and dimensional stability, but they involve a drawback of insufficient solvent resistance and moldability.
- Japanese Patent Laid Open Sho 57-108151 discloses a butyl rubber
- Japanese Patent Laid Open Sho 57-108152 discloses an ethyl ene-propylene copolymer and/or ethyl ene-propylene-diene copolymer
- Japanese Patent Laid Open Sho 57-111351 discloses an isoprene rubber and/or methyl pentene polymer.
- the present inventors have previously proposed a process for producing a polyolefin-polyester graft copolymer that can be used as a satisfactory compatibilizing agent for a polycarbonate resin and a polyolefin by reacting from 15 to 85 parts by weight of a polyester having an intrinsic viscosity [ ⁇ ] of 0.30 and 1.2 and a concentration of terminal carboxyl group of 15 to 200 meg/ g, and from 85 to 15 parts by weight of a modified polyolefin containing 0.2 to 5 moll of epoxy groups and having a weight average molecular weight of 8,000 to 140,000 in a twin screw extruder at 260 - 320°C (Japanese Patent Application Sho 63-258883).
- an object of the present invention to provide a polypropylene-polyester graft copolymer capable of functioning as a compatibilizing agent for a polycarbonate resin and a polyolefin, particularly, a polypropylene.
- Another object of the present invention is to provide a process for producing such a propylene-polyester graft copolymer.
- a graft copolymer of a polyester and a functional group-containing modified polypropylene is effective as a compatibilizing agent for a polycarbonate resin and a polyolefin, particularly, a polypropylene and that a desired polypropylene-polyester graft copolymer can be obtained through grafting reaction by defining the intrinsic viscosity and the concentration of the terminal carboxyl group of the polyester and the functional group content and the melt flow rate (MFR) of the modified polypropylene to respective specific ranges.
- a polypropylene-polyester graft copolymer according to the present invention comprises from 10 to 90 parts by weight of a polyester having an intrinsic viscosity [ ⁇ ] of 0.5 to 1.8 and a concentration of terminal carboxyl group of 10 to 1000 meq/Kg, and 90 to 10 parts by weight of a modified polypropylene containing 0.2 to 5.0 % by weight of functional groups and a melt flow rate (MFR) measured at 230°C under the load of 2160 g) of 0.5 to 80 g/10 min.
- a process for producing a polypropylene- polyester graft copolymer according to the present invention comprises reacting:
- the polyester used in the present invention is, generally, a thermoplastic resin comprising a saturated dicarboxylic acid and a saturated difunctional alcohol and there can be mentioned, for example, polyethylene terephthalate, polypropylene terephthalate, polytetramethylene terephthalate (polybutylene terephthalate), polyhexamethylene terephthalate, polycyclohexane-1,4-dimethylol terephthalate and polyneopentyl terephthalate.
- polyethylene terephthalate and polybutylene terephthalate are particularly preferred.
- the polyester has an intrinsic viscosity [ ] Of 0.5 to 1.8 and a concentration of terminal carboxyl group of 10 to 100 meq/Kg.
- the intrinsic viscosity [ ⁇ ] (dl/g) is determined from a solution viscosity measured in an o-chlorophenol solvent at 25°C. If the intrinsic viscosity [ ⁇ ] of the polyester is less than 0.5, the effect for improving the compatibility is insufficient. On the other hand, if it exceeds 1.8, the melt viscosity of the reaction product is increased to bring about a difficulty in fabrication. Meanwhile, if the concentration of the terminal carboxyl group is less than 10 meq/Kg, reactivity with the modified polypropylene is poor.
- the intrinsic viscosity [ ⁇ ] is from 0.5 to 1.0 and the concentration of the terminal carboxyl group is from 10 to 100 meq/kg. If the intrinsic viscosity [ ⁇ ] exceeds 1.0, the m melt viscosity of the graft polymer is increased to cause gelation.
- the terephthalic acid ingredient in the polyethylene terephthalate may be substituted with alkyl group, halogen group, etc.
- the glycol ingredient may contain, in addition to ethyl ene glycol, up to about 50% by weight of other glycol, for example, 1,4-butylene glycol, propylene glycol, hexamethylene glycol, etc.
- the intrinsic viscosity [ ⁇ ] is from 0.5 to 1.8 and the concentration of the terminal carboxyl group is from 10 to 100 meq/Kg.
- the terephthalic acid ingredient may be substituted with alkyl group, halogen group, etc. Further.
- the modified polypropylene used in the present invention is a polypropylene containing an unsaturated monomer having a functional group.
- the functional group contained in the modified polypropylene is at least one such group that is reactive with the terminal carboxyl group or hydroxyl group of the polyester and it can include for example carboxyl group, epoxy group, hydroxyl group and amino group.
- the unsaturated monomer having carboxyl group is an unsaturated carboxyl ic acid or anhydride thereof and it can include, for example, monocarboxylic acid such as acrylic acid or methacrylic acid, dicarboxylic acid such as maleic acid, humaric acid or itanconic acid, dicarboxylic acid anhydride such as maleic acid anhydride or itaconic acid anhydride, the dicarboxylic acid and anhydride thereof being particularly preferred.
- monocarboxylic acid such as acrylic acid or methacrylic acid
- dicarboxylic acid such as maleic acid, humaric acid or itanconic acid
- dicarboxylic acid anhydride such as maleic acid anhydride or itaconic acid anhydride
- the dicarboxylic acid and anhydride thereof being particularly preferred.
- the unsaturated monomer having epoxy group there can be mentioned glycidyl ester of metacrylic acid or glycidyl ester of acrylic acid.
- the backbone for the functional group-containing modified polypropylene may be any of block copolymer, graft copolymer, random copolymer or intercopolymer of, e.g., propylene and it is, particularly preferably, a propylene random copolymer containing a non-conjugated diene comonomer represented by the general formula: where R 1 - R 4 each represents H or an alkyl group with 1 to 6 carbon atoms and n represents an integer of 1 to 20.
- non-conjugated diene there can be mentioned, for example, 1,4-hexadiene, 7-methyl-1,6-octadiene, 5-methyl- 1,4-hexadiene, 1,9-decadiene, 4-methyl-1,4-heptadiene, 4-ethyl- 1,4-hexadiene and 1,13-tetradecadiene.
- 1,4-hexadiene, 7-methyl-1,6-octadiene, 5-methyl-1,4-hexadiene and 1,9 decadiene are particularly preferred.
- Two or more of the non-conjugated diene comonomers may be used in admixture.
- the ratio of the non-conjugated diene is from 0.05 to 10 mol%. If the content of the non-conjugated diene is less than 0.05 mol%, high grafting rate can not be obtained in the subsequent grafting reaction. On the other hand, if it exceeds 10 mol%, crystal Unity of the copolymer is remarkably reduced. More preferred content of the non-conjugated diene is from 0.1 to 3 mol%.
- propylene copolymerized with the unsaturated monomer having the functional group as described above may be incorporated as required, with less than 10% by weight of olefin such as ethylene, butene-1 or pentene-1, monomers such as vinyl acetate, isoprene, chloroprene or butadiene.
- olefin such as ethylene, butene-1 or pentene-1
- monomers such as vinyl acetate, isoprene, chloroprene or butadiene.
- the unsaturated monomer having the functional group may be reacted with the polypropylene-non conjugated diene random copolymer by the following methods.
- melt-kneading method melt-kneading a random copolymer, a monomer and a radical generator using an extruder or the like thereby causing reaction, etc.
- the melt-kneading method is suitable since the continuous reaction is easy.
- the reaction time is preferably from 10 sec to 20 min.
- peroxides such as benzoyl peroxide, lauroyl peroxide, ditertiary butylperoxide, acetyl peroxide, tertiary butyl peroxybenzoic acid, dicumyl peroxide, peroxybenzoic acid, peroxyacetic acid, tertiary butyl peroxypivalate, or diazo compounds such as azobisisobutylonitrile are preferred.
- the blending ratio is desirably within a range from 0.1 to 10 parts by weight based on 100 parts by weight of the radical polymerizable monomer. It is also possible to cause grafting reaction by kneading under heating without using the radical generator.
- melt flow rate (MFR) of the modified polypropylene be from 0.5 to 80 g/10 min and the amount of the functional group in the modified polypropylene be from 0.1 to 2.0% by weight.
- the melt flow rate (MFR) was measured at 230oC under the load of 2160 g and represented by the unit of g/10 min.
- the functional group content was determined from the analytical value for elemental oxygen. If the melt flow rate (MFR) exceeds 80 g/10 min (that is, if the molecular weight is too low), reaction with polyester minimally occurs, bringing about a difficulty in the snythesis of the graft copolymer.
- the melt viscosity is increased such that moldability properties are adversely affected.
- the average molecular weight (Mw) of the modified polypropylene having MFR from 0.5 to 80 g/10 min is about from 70,000 to 300,000.
- the functional group is less than 0.1% by weight, the reactivity with the polyester is so poor that graft copolymer is minimally formed.
- it exceeds 2.0% by weight the melt viscosity of the reaction product is increased due to the excess reaction, tending to result in gel-like material.
- both of them are dry blended and then melt-kneaded at 240 - 300oC, for polypropylene, and at 260 - 320oC for other polyolefins.
- the melt-kneading is preferably conducted in an extruder, particularly, in a twin screw extruder. If the reaction temperature is lower than described, the grafting is not sufficient. On the other hand, if it exceeds that described, excess reaction occurs and the melting temperature of the reaction product is increased, tending to cause blocking in the extruder. Further, the modified polypropylene adversely tends to be degraded more easily.
- the time for the grafting reaction is typically from about 0.5 to 15 min although it may vary depending on the reaction conditions.
- the blending amount of the polyester and the modified polypropylene is from 10 to 90 parts by weight, preferably, from 20 to 80 parts by weight from the former and from 90 to 10 parts by weight and, preferably, from 80 to 20 parts by weight for the latter. If the polyester is less than 10 parts by weight or greater than 90 parts by weight, the amount of the graft copolymer formed is reduced.
- the thus obtained polypropylene-polyester graft copolymer is useful as a compatibilizing agent for a polycarbonate resin and a polyolefin, particularly a polypropylene and, generally, it is added at a ratio of 1 to 30 parts by weight based on 100 parts by weight of the sum of both of them.
- the grafting reaction proceeds easily, a graft copolymer of sufficient grafting ratio can be obtained and formation of gel due to excess reaction can be prevented.
- MFR melt flow rate
- Examples 1 - 6 Comparative Examples 1 - 3 As shown in Table 1, after blending polyethylene terephthalate or a polybutylene terephthalate each having various intrinsic viscosities [ ] and concentrations of terminal carboxyl group and modified polypropylene (graft copolymer of propylene non-conjugated diene random copolymer and maleic acid anhydride or glycidyl methacrylate) having various functional group contents and melt flow rates (MFR) at a ratio of 20/80 (by weight), they were supplied to a twin screw extruder of 45 mm ⁇ and a melt-kneaded at 280°C at 200 rpm to proceed grafting reaction.
- MFR melt flow rates
- Example 7 A copolymer was produced and measured in the same manner as in Example 1 except for using, as a polyester, a mixture of 50% by weight of a polyethylene terephthalate having an intrinsic viscosity [ ] of 0.72 and a concentration of terminal carboxyl group of 30 meq/Kg, and 50% by weight of a polybutylene terephthalate having an intrinsic viscosity [ ⁇ ] of 0.85 and a concentration of terminal carboxyl group of 52 meq/Kg. The results are also shown in Table 1. Also in this example, neither the gel formation nor the clogging of the extruder was observed. Examples 8, 9 Copolymers were produced in the same manner as in Example 1 except for changing the ratio (by weight) of the polybutylene
- polyester having an intrinsic viscosity [ ⁇ ] and a concentration of terminal carboxyl group each within a predetermined range, and a modified polypropylene having a functional group content and a melt flow rate (MFR) each in a predetermined range are reacted, a copolymer can be obtained at a high grafting ratio.
- the polypropylene-polyester graft copolymer according to the present invention thus obtained is extremely effective as a compatibilizing agent for a polycarbonate resin and a polyolefin, particularly, a polypropylene.
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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)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Graft Or Block Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002050283A CA2050283A1 (en) | 1989-04-12 | 1990-04-11 | Polypropylene-polyester graft copolymer and production method thereof |
KR1019910701305A KR920701312A (en) | 1989-04-12 | 1990-04-11 | Polypropylene-Polyester Graft Copolymer and Method for Making the Same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1/92180 | 1989-04-12 | ||
JP9218089 | 1989-04-12 | ||
JP1324269A JPH0347844A (en) | 1989-04-12 | 1989-12-14 | Polypropylene-polyester graft copolymer and production thereof |
JP1/324269 | 1989-12-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990012054A1 true WO1990012054A1 (en) | 1990-10-18 |
Family
ID=26433649
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1990/001841 WO1990012054A1 (en) | 1989-04-12 | 1990-04-11 | Polypropylene-polyester graft copolymer and production method thereof |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0467958A4 (en) |
JP (1) | JPH0347844A (en) |
KR (1) | KR920701312A (en) |
AU (1) | AU5422290A (en) |
CA (1) | CA2050283A1 (en) |
WO (1) | WO1990012054A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0443736A2 (en) * | 1990-02-02 | 1991-08-28 | Tonen Corporation | Thermoplastic resin composition |
US5283285A (en) * | 1993-04-05 | 1994-02-01 | Alliedsignal Inc. | High impact polyester/polycarbonate blends |
WO1995029949A1 (en) * | 1994-04-28 | 1995-11-09 | Borealis A/S | Graft copolymer of functionalized polypropylene polymer and novolak polymer |
WO1995029955A1 (en) * | 1994-04-28 | 1995-11-09 | Borealis A/S | Polymer alloy compatibilized with a graft copolymer of functionalized polypropylene polymer and novolak polymer |
WO2020200688A1 (en) * | 2019-03-29 | 2020-10-08 | Sabic Global Technologies B.V. | Film from graft copolymer having a polypropylene backbone, and nanoporous polypropylene membrane |
CN114269834A (en) * | 2019-08-18 | 2022-04-01 | Sabic环球技术有限责任公司 | Use of a composition for producing foamed articles |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4172859A (en) * | 1975-05-23 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Tough thermoplastic polyester compositions |
JPS59215351A (en) * | 1983-05-24 | 1984-12-05 | Mitsui Petrochem Ind Ltd | Thermoplastic resin composition |
US4654401A (en) * | 1984-12-24 | 1987-03-31 | General Electric Company | Hydroxyl group graft modified polyolefins |
EP0333414A2 (en) * | 1988-03-16 | 1989-09-20 | Polyplastics Co. Ltd. | Improved thermoplastic polyester resin and process for producing the same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4555546A (en) * | 1983-12-29 | 1985-11-26 | Monsanto Company | Compatibilized blends of acrylic ester |
JPH0623301B2 (en) * | 1987-01-16 | 1994-03-30 | ゼネラル・エレクトリック・カンパニイ | Olefin impact modifiers for thermoplastic polyester resins and blends therewith |
JP2599630B2 (en) * | 1988-10-14 | 1997-04-09 | 東燃化学株式会社 | Polyolefin-polyester graft copolymer and method for producing the same |
-
1989
- 1989-12-14 JP JP1324269A patent/JPH0347844A/en active Pending
-
1990
- 1990-04-11 CA CA002050283A patent/CA2050283A1/en not_active Abandoned
- 1990-04-11 AU AU54222/90A patent/AU5422290A/en not_active Abandoned
- 1990-04-11 WO PCT/US1990/001841 patent/WO1990012054A1/en not_active Application Discontinuation
- 1990-04-11 KR KR1019910701305A patent/KR920701312A/en not_active Application Discontinuation
- 1990-04-11 EP EP19900906580 patent/EP0467958A4/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4172859A (en) * | 1975-05-23 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Tough thermoplastic polyester compositions |
JPS59215351A (en) * | 1983-05-24 | 1984-12-05 | Mitsui Petrochem Ind Ltd | Thermoplastic resin composition |
US4654401A (en) * | 1984-12-24 | 1987-03-31 | General Electric Company | Hydroxyl group graft modified polyolefins |
EP0333414A2 (en) * | 1988-03-16 | 1989-09-20 | Polyplastics Co. Ltd. | Improved thermoplastic polyester resin and process for producing the same |
Non-Patent Citations (1)
Title |
---|
See also references of EP0467958A4 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0443736A2 (en) * | 1990-02-02 | 1991-08-28 | Tonen Corporation | Thermoplastic resin composition |
EP0443736A3 (en) * | 1990-02-02 | 1992-04-22 | Tonen Corporation | Thermoplastic resin composition |
US5298557A (en) * | 1990-02-02 | 1994-03-29 | Tonen Corporation | Thermoplastic resin composition |
US5444119A (en) * | 1990-02-02 | 1995-08-22 | Tonen Corporation | Thermoplastic resin composition |
US5283285A (en) * | 1993-04-05 | 1994-02-01 | Alliedsignal Inc. | High impact polyester/polycarbonate blends |
WO1995029949A1 (en) * | 1994-04-28 | 1995-11-09 | Borealis A/S | Graft copolymer of functionalized polypropylene polymer and novolak polymer |
WO1995029955A1 (en) * | 1994-04-28 | 1995-11-09 | Borealis A/S | Polymer alloy compatibilized with a graft copolymer of functionalized polypropylene polymer and novolak polymer |
WO2020200688A1 (en) * | 2019-03-29 | 2020-10-08 | Sabic Global Technologies B.V. | Film from graft copolymer having a polypropylene backbone, and nanoporous polypropylene membrane |
CN114269834A (en) * | 2019-08-18 | 2022-04-01 | Sabic环球技术有限责任公司 | Use of a composition for producing foamed articles |
CN114269834B (en) * | 2019-08-18 | 2023-08-15 | Sabic环球技术有限责任公司 | Use of a composition for producing foamed articles |
Also Published As
Publication number | Publication date |
---|---|
KR920701312A (en) | 1992-08-11 |
EP0467958A1 (en) | 1992-01-29 |
CA2050283A1 (en) | 1990-10-13 |
AU5422290A (en) | 1990-11-05 |
JPH0347844A (en) | 1991-02-28 |
EP0467958A4 (en) | 1992-08-19 |
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