CA1185726A - Impact strength improved polyphenylene ether resin compositions - Google Patents
Impact strength improved polyphenylene ether resin compositionsInfo
- Publication number
- CA1185726A CA1185726A CA000401171A CA401171A CA1185726A CA 1185726 A CA1185726 A CA 1185726A CA 000401171 A CA000401171 A CA 000401171A CA 401171 A CA401171 A CA 401171A CA 1185726 A CA1185726 A CA 1185726A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- parts
- polyphenylene ether
- ether resin
- composition
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
Classifications
-
- 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
- C08K5/13—Phenols; Phenolates
Landscapes
- 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)
Abstract
ABSTRACT OF THE DISCLOSURE
The impact resistance of articles produced from a composition rich in polyphenylene ether resin alone or in combination with conventional additives is stabilized when the starting polyphenylene ether resin (or a composition containing the resin) includes a small but effective content of a hindered phenolic compound.
The impact resistance of articles produced from a composition rich in polyphenylene ether resin alone or in combination with conventional additives is stabilized when the starting polyphenylene ether resin (or a composition containing the resin) includes a small but effective content of a hindered phenolic compound.
Description
5~
IMPACT STRENGTH IMPROVED POLYETHYLENE
ETHER RESIN COMPOSITIONS
The present invention relates to polypheny-lene ether resin compositions of improved impact resistance. More particularly, the invention relates to polyphenylene ether resins alone and in admixture with conventional additives together with an agent which inhibits degradation of the resin at molding temperatures, and to filled and/or plasticized comp-ositions.
Back~round of the Invention The polyphenylene ether resins (also termed "polyphenylene oxide resins") are a well-known family ~f linear thermoplastic engineering resins having the repeating formula: ~
~ O _~ O ~1, wherein X and X' independently represent inert sub-stituents, ~ and Y' each independently represent an inert substituent, and n represents a number (usually 50 or more) which is sufficiently large ~o that the polyether possesses a softening point which is sufficiently high to satisfy engineering re~uirements. A wide variety of these resins and a number of me-thods for their preparations are disclosed in Hay U.S. Patent No.
3,306~874, issued February 28, 1967 and 3,306,875, issued February 28, 1967, as well as in Stamatoff U.S.
Patent No. 3,257,357, issued June 21, 1966 and U.S.
Patent No. 3,257,358~ issued June 21, 1966. The .
~ 2,~3 8CN-3277 substituents desi~nated by X, X', Y and ~' are not critical so long as they are inert and thermostable, and a variety of lower alkyl, cycloal~yl, halo-hydrocarbon, hydrocarbonoxy and halohydrocarbonoxy substikuents have been found to be generally useful.
The resins wherein X and X' represent hydroyen and Y and Y' represent methyl have long been in large-scale commercial production, the preferred polymer being poly(2,6-dimethyl-1,4-phenylene)ether, prepared by the catalyzed oxidative polymerization of 2,6-xylenol.
~ olding compositions containing relatively high amounts of said resins, e.g., from 70 to gO or even 100 parts per hundred of the total resin are very diEficult to process (because of their otherwise excellent high hea-t properties) and this is reflected in poorer impact strength than is desired.
It has now been found that the impact resistance of moldings prepared compositions rich in the polyphenylene ether resins of the type described is stabilized or increased, and in preferred instances is very greatly increased, when the polyphenylene ether resin is supplied to the molding machine in admixture with ahindered phenolic compound. The improvement occurs when the resins are molded alone in admixture only with the phenolic compound, and also when the resins are molded in admixture with one or more of the customary added materials, and is more fully disclosed below. Impact resistance is a very important physical property of a molded thermoplastic article, and even a slight increase in this property is of commercial importance. Moreover, the resins can be ~ 8CN-3277 molded in admixture with an organic plasticizer (typically a triaryl phosphate) and a mineral filler (typically clay~ and neither of these material inhibits the impact strength improving action of the above-mentioned phenolic compound.
The invention thus provides useful comp-ositions high in polyphenylene ether resin content with over a small but effective amount of a hindered phenolic compound as an impact strength stabilizer or enhancer for the resin. The invention fur-ther provides such thermoplastic mol~ing compositions of improved properties, which also include a triaryl phosphite as plasticizer and/or clay as filler.
The present invention is applicable to the engineering grade thermostable polyphenylene ether resins as a family.
Illustrative of the hindred phenolic compounds which can be in the compositions of the present invention are a well-known and large group of agents known in this art and lis-ted among others, for example, in the Encyclopedia of Polymer Science and Technology, Volume
IMPACT STRENGTH IMPROVED POLYETHYLENE
ETHER RESIN COMPOSITIONS
The present invention relates to polypheny-lene ether resin compositions of improved impact resistance. More particularly, the invention relates to polyphenylene ether resins alone and in admixture with conventional additives together with an agent which inhibits degradation of the resin at molding temperatures, and to filled and/or plasticized comp-ositions.
Back~round of the Invention The polyphenylene ether resins (also termed "polyphenylene oxide resins") are a well-known family ~f linear thermoplastic engineering resins having the repeating formula: ~
~ O _~ O ~1, wherein X and X' independently represent inert sub-stituents, ~ and Y' each independently represent an inert substituent, and n represents a number (usually 50 or more) which is sufficiently large ~o that the polyether possesses a softening point which is sufficiently high to satisfy engineering re~uirements. A wide variety of these resins and a number of me-thods for their preparations are disclosed in Hay U.S. Patent No.
3,306~874, issued February 28, 1967 and 3,306,875, issued February 28, 1967, as well as in Stamatoff U.S.
Patent No. 3,257,357, issued June 21, 1966 and U.S.
Patent No. 3,257,358~ issued June 21, 1966. The .
~ 2,~3 8CN-3277 substituents desi~nated by X, X', Y and ~' are not critical so long as they are inert and thermostable, and a variety of lower alkyl, cycloal~yl, halo-hydrocarbon, hydrocarbonoxy and halohydrocarbonoxy substikuents have been found to be generally useful.
The resins wherein X and X' represent hydroyen and Y and Y' represent methyl have long been in large-scale commercial production, the preferred polymer being poly(2,6-dimethyl-1,4-phenylene)ether, prepared by the catalyzed oxidative polymerization of 2,6-xylenol.
~ olding compositions containing relatively high amounts of said resins, e.g., from 70 to gO or even 100 parts per hundred of the total resin are very diEficult to process (because of their otherwise excellent high hea-t properties) and this is reflected in poorer impact strength than is desired.
It has now been found that the impact resistance of moldings prepared compositions rich in the polyphenylene ether resins of the type described is stabilized or increased, and in preferred instances is very greatly increased, when the polyphenylene ether resin is supplied to the molding machine in admixture with ahindered phenolic compound. The improvement occurs when the resins are molded alone in admixture only with the phenolic compound, and also when the resins are molded in admixture with one or more of the customary added materials, and is more fully disclosed below. Impact resistance is a very important physical property of a molded thermoplastic article, and even a slight increase in this property is of commercial importance. Moreover, the resins can be ~ 8CN-3277 molded in admixture with an organic plasticizer (typically a triaryl phosphate) and a mineral filler (typically clay~ and neither of these material inhibits the impact strength improving action of the above-mentioned phenolic compound.
The invention thus provides useful comp-ositions high in polyphenylene ether resin content with over a small but effective amount of a hindered phenolic compound as an impact strength stabilizer or enhancer for the resin. The invention fur-ther provides such thermoplastic mol~ing compositions of improved properties, which also include a triaryl phosphite as plasticizer and/or clay as filler.
The present invention is applicable to the engineering grade thermostable polyphenylene ether resins as a family.
Illustrative of the hindred phenolic compounds which can be in the compositions of the present invention are a well-known and large group of agents known in this art and lis-ted among others, for example, in the Encyclopedia of Polymer Science and Technology, Volume
2, pages 190-lg4, Interscience, New York, 1965.
Speciic mention is made of 4 methoxy-2-t-butylphenol, 2,6-t-butyl-p-cresol, 2,6-di-t-butyl-4-methoxyphenol.
Preferred are 2,2'-methylenebis-(6~methyl-2-t-butylphenol), available from Catali~ as CAO-14 and tetrakis [methylene-3-(3'5-di-t-butyl-4l-hydroxy-phenyl) propionate] methane, available from Geigy as IRGANOX
1010 .
The foregoing compounds are effective for the purposes of the present in~ention in very small proportions. In the case of the preferred phenolic compounds as little as 0.1 part per hundred based on the weight of the polyphenylene ether resin provides a significant improvement, and up to 5 parts per hundred on the same basis, and even more can be present.
In practice between about 0.5 parts and 2 parts of the phenolic compound on the same basis, provides satis-factory impact strength retention and/or improvement while avoiding over- or under-use of the agent.
The composition of the hindered phenolic compound and the polyphenylene ether resin (or mixture o~ such resin with one or more of the usual additives which are employed to form a molding composition) can be prepared by any of the methods therefor which have been used in the past. Thus the components, each in granular or powder form, can be dry blended to form a gree-flowing particulate mix. If pre~erred, a mixture of the polyphenylene ether resin and the phenolic compound (or mixture of phenolic compounds) can be melted and the resulting homogeneous solution can be cooled until solid and then comminuted to form a ~ree-flowing particulate product.
~lternatively, when feasible the antioxidant can be mixed into a plasticizer or into any supplementary resin which may be present, for example the styrene-butadiene-styrene block copolymer which is often included as an agent for improving the properties of articles made from the compositions. The invention does not depend on which r,lethod is adopted.
A variety of materials can be present which do not a~fect the essential character of the resin-phenolic mixture. Thus the mixture can contain:
resins which are intended to improve the properties ~ 8CN-3277 of articles coming from the molding machine/ such as the rubbery styrene-butadlene-styrene copolymer resin re~erred to above; a plasticizer (-for example, 5% to 15% by weight of triphenyl or other similar triaryl phosphate); glass or asbestos ~ibers, or graphite "whiskers" as reinforcing ~illers, halogen, and/or phosphorus compoundsas fire-retardants; non-reinforcing fillers (for example 5% to 50% of clay); one or more dyes; and oneor more pi~men-ts (for example carbon 'black, phthalocyanine blue and titanium dioxide white). The polyphenylene ether resins tolerate large proportions of these supplementary agents, so the weight of the polyphenylene ether resin can vary within broad ranges. Generally however, for filled and/or plasticized molding compositions the composition of polyphenylene ether and hindered phenolic compounds should be hetween 40 and 80 parts by weight per 100 parts by weight of the molding composition.
The compositions which have been described above can be successfully molded in the same ways as polyphenylene ether resin molding compositions have been molded in the past. Blow, injection and extrusion processes can be employed in molding machines working in the conventional temperature range of 450 F-650 F.
The invention is further illustrated by the examples which follow. These examples are preferred embodiments of the invention, and are not to be construed in limitation thereof. Parts are by weight unless otherwise stated.
EXAMPLES''I AND II
The following illustrates the comparative ~CN-3277 effect of two preferred phenolic compounds maintaining or enhancing the impact strength of a commercial polyphenylene ether resin in admixture with customary additives. The antioxidants used are:
A. -2,2'-Methylenebis-~4-methyl-6-~-butylphenol) (CAO-14/ catalin), and B. tetrakis [methylene 3-(3',5'-di-t-butyl-4-hydroxy-phenyl)propionate~ methane.
(IRGANOX 1010, Geigy) in a standard laboratory test composition.
A control composition is prepared by dry blending:
Poly (2,6-dimethyl-1,~-phenylene)ether resin (PPO, polymeric material, General Electric Co.) 91 parts Styrene-butadiene-styrene block copolymer (Kraton G-1651, Shell Chemical Co.) 8 parts Triaryl phosphate (Kronitex 50, FMC
Corp.) 9 parts Run 1. Test compositions are prepared by blending 1 part of the respective hindered phenolic compound shown above into 109 parts of the control composition prepared as described above. All compositions are melt blended in a laboratory Warner~Pfeiderer extrusion molding machine working at 600F and ~est bars were molded in a 3 oz. Newbury in~ection molding machine. The molded test bars are used to determine tensile yield, tensile strength and tensile elongation, and also their impact resistance by the Izod and Gardner methods.
Run 2. The procedures of Run 1 are repeated 7~
except with a new batch of the control composition.
The phenolic compounds used are identified in the table below by the designating letters shown above.
ControlO The foregoing procedure i5 repeated with the control composition (which contains no phenolic compound).
The tensile yield and Gardner impact strength values of all of bars (including the control bars) are substantially the same. The phenolic compound does not significantly improve or harm these properties.
The other results are as follows:
T e n s i 1 e ~ntioxidant Strength Elongation Izod Used (p.s.i.) % Impact ~ft.-lb./in.n) .... .. . _ , , :~ Par-ts Run 1 Run 2 Run 1 Run ? Run 1 Run 2 Control None 9,175 9,030 75 53 2.7 3.1 A(I) 1 9,700 9,770 80 79 4.2 4.0 B(II) 1 9,470 9,000 69 57 3.9 3.7 ~ _ . . . _ . . _ _ . _ *See text above.
The data show that the present invention is capable of increasing tensile strength by 8.2%, elongation by 49%, and Izod impact resistance by 56%.
Obviously, other modifications and vari-ations are possible, in the light of the above teachings. For example, the following hindered phenolic compounds may be substi-tuted:
o-t-buty]anisole and 2,6-di-t-butyl-4-cresol. In addition, up to 125 parts of clay filler per 100 parts of polyphenylene ether resin can be included. The block copolymer and the ph.osphate plasticizer can be omitted, and the like. It is thereforel to be under-stood that changes may be made in the particular embodimen-ts of the invention desc.ribed which are within the full intended scope of the invention as defined by the appended claims.
--8~
Speciic mention is made of 4 methoxy-2-t-butylphenol, 2,6-t-butyl-p-cresol, 2,6-di-t-butyl-4-methoxyphenol.
Preferred are 2,2'-methylenebis-(6~methyl-2-t-butylphenol), available from Catali~ as CAO-14 and tetrakis [methylene-3-(3'5-di-t-butyl-4l-hydroxy-phenyl) propionate] methane, available from Geigy as IRGANOX
1010 .
The foregoing compounds are effective for the purposes of the present in~ention in very small proportions. In the case of the preferred phenolic compounds as little as 0.1 part per hundred based on the weight of the polyphenylene ether resin provides a significant improvement, and up to 5 parts per hundred on the same basis, and even more can be present.
In practice between about 0.5 parts and 2 parts of the phenolic compound on the same basis, provides satis-factory impact strength retention and/or improvement while avoiding over- or under-use of the agent.
The composition of the hindered phenolic compound and the polyphenylene ether resin (or mixture o~ such resin with one or more of the usual additives which are employed to form a molding composition) can be prepared by any of the methods therefor which have been used in the past. Thus the components, each in granular or powder form, can be dry blended to form a gree-flowing particulate mix. If pre~erred, a mixture of the polyphenylene ether resin and the phenolic compound (or mixture of phenolic compounds) can be melted and the resulting homogeneous solution can be cooled until solid and then comminuted to form a ~ree-flowing particulate product.
~lternatively, when feasible the antioxidant can be mixed into a plasticizer or into any supplementary resin which may be present, for example the styrene-butadiene-styrene block copolymer which is often included as an agent for improving the properties of articles made from the compositions. The invention does not depend on which r,lethod is adopted.
A variety of materials can be present which do not a~fect the essential character of the resin-phenolic mixture. Thus the mixture can contain:
resins which are intended to improve the properties ~ 8CN-3277 of articles coming from the molding machine/ such as the rubbery styrene-butadlene-styrene copolymer resin re~erred to above; a plasticizer (-for example, 5% to 15% by weight of triphenyl or other similar triaryl phosphate); glass or asbestos ~ibers, or graphite "whiskers" as reinforcing ~illers, halogen, and/or phosphorus compoundsas fire-retardants; non-reinforcing fillers (for example 5% to 50% of clay); one or more dyes; and oneor more pi~men-ts (for example carbon 'black, phthalocyanine blue and titanium dioxide white). The polyphenylene ether resins tolerate large proportions of these supplementary agents, so the weight of the polyphenylene ether resin can vary within broad ranges. Generally however, for filled and/or plasticized molding compositions the composition of polyphenylene ether and hindered phenolic compounds should be hetween 40 and 80 parts by weight per 100 parts by weight of the molding composition.
The compositions which have been described above can be successfully molded in the same ways as polyphenylene ether resin molding compositions have been molded in the past. Blow, injection and extrusion processes can be employed in molding machines working in the conventional temperature range of 450 F-650 F.
The invention is further illustrated by the examples which follow. These examples are preferred embodiments of the invention, and are not to be construed in limitation thereof. Parts are by weight unless otherwise stated.
EXAMPLES''I AND II
The following illustrates the comparative ~CN-3277 effect of two preferred phenolic compounds maintaining or enhancing the impact strength of a commercial polyphenylene ether resin in admixture with customary additives. The antioxidants used are:
A. -2,2'-Methylenebis-~4-methyl-6-~-butylphenol) (CAO-14/ catalin), and B. tetrakis [methylene 3-(3',5'-di-t-butyl-4-hydroxy-phenyl)propionate~ methane.
(IRGANOX 1010, Geigy) in a standard laboratory test composition.
A control composition is prepared by dry blending:
Poly (2,6-dimethyl-1,~-phenylene)ether resin (PPO, polymeric material, General Electric Co.) 91 parts Styrene-butadiene-styrene block copolymer (Kraton G-1651, Shell Chemical Co.) 8 parts Triaryl phosphate (Kronitex 50, FMC
Corp.) 9 parts Run 1. Test compositions are prepared by blending 1 part of the respective hindered phenolic compound shown above into 109 parts of the control composition prepared as described above. All compositions are melt blended in a laboratory Warner~Pfeiderer extrusion molding machine working at 600F and ~est bars were molded in a 3 oz. Newbury in~ection molding machine. The molded test bars are used to determine tensile yield, tensile strength and tensile elongation, and also their impact resistance by the Izod and Gardner methods.
Run 2. The procedures of Run 1 are repeated 7~
except with a new batch of the control composition.
The phenolic compounds used are identified in the table below by the designating letters shown above.
ControlO The foregoing procedure i5 repeated with the control composition (which contains no phenolic compound).
The tensile yield and Gardner impact strength values of all of bars (including the control bars) are substantially the same. The phenolic compound does not significantly improve or harm these properties.
The other results are as follows:
T e n s i 1 e ~ntioxidant Strength Elongation Izod Used (p.s.i.) % Impact ~ft.-lb./in.n) .... .. . _ , , :~ Par-ts Run 1 Run 2 Run 1 Run ? Run 1 Run 2 Control None 9,175 9,030 75 53 2.7 3.1 A(I) 1 9,700 9,770 80 79 4.2 4.0 B(II) 1 9,470 9,000 69 57 3.9 3.7 ~ _ . . . _ . . _ _ . _ *See text above.
The data show that the present invention is capable of increasing tensile strength by 8.2%, elongation by 49%, and Izod impact resistance by 56%.
Obviously, other modifications and vari-ations are possible, in the light of the above teachings. For example, the following hindered phenolic compounds may be substi-tuted:
o-t-buty]anisole and 2,6-di-t-butyl-4-cresol. In addition, up to 125 parts of clay filler per 100 parts of polyphenylene ether resin can be included. The block copolymer and the ph.osphate plasticizer can be omitted, and the like. It is thereforel to be under-stood that changes may be made in the particular embodimen-ts of the invention desc.ribed which are within the full intended scope of the invention as defined by the appended claims.
--8~
Claims (5)
1. A filled thermoplastic molding composition comprising a filler and from 40 to 80 parts by weight, based on the total composition weight, of a composition comprising a polyphenylene ether resin and a small but effective amount of a hindered phenolic compound consisting essentially of 4-methoxy-2-t-butylphenol as an impact strength stabilizer for said resin, the polyphenylene ether resin comprising at least 70 parts by weight of the total resin components of the composition.
2. A composition according to claim 1 wherein said resin is a poly(2,6-dimethyl-1,4-phenylene)ether resin.
3. A composition according to claim 1 wherein the weight of said phenolic compound is between about 0.1 and 5 parts by weight per 100 parts by weight of said polyphenylene ether resin.
4. A filled thermoplastic molding composition comprising at least 40 parts by weight of a composition according to claim 1 and at least 5 parts by weight of a clay filler per 100 parts by weight of said molding composition.
5. A plasticized thermoplastic molding composition comprising at least 40 parts by weight of a composition according to claim 1 and at least 5 parts by weight of a triaryl phosphate plasticizer per 100 parts by weight of said molding composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26392381A | 1981-05-15 | 1981-05-15 | |
| US263,923 | 1981-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1185726A true CA1185726A (en) | 1985-04-16 |
Family
ID=23003824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000401171A Expired CA1185726A (en) | 1981-05-15 | 1982-04-16 | Impact strength improved polyphenylene ether resin compositions |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0078835A4 (en) |
| JP (1) | JPS58500718A (en) |
| CA (1) | CA1185726A (en) |
| WO (1) | WO1982004057A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2328962B1 (en) * | 2008-08-29 | 2016-01-06 | Solvay Specialty Polymers USA, LLC. | Thermally stabilized polyarylene compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1101622A (en) * | 1965-01-13 | 1968-01-31 | Gen Electric | Polyphenylene oxide stabilizers |
| US3285855A (en) * | 1965-03-11 | 1966-11-15 | Geigy Chem Corp | Stabilization of organic material with esters containing an alkylhydroxy-phenyl group |
| NL90598C (en) * | 1973-11-14 | |||
| US4154775A (en) * | 1977-09-06 | 1979-05-15 | General Electric Company | Flame retardant composition of polyphenylene ether, styrene resin and cyclic phosphate |
| US4154719A (en) * | 1977-12-21 | 1979-05-15 | General Electric Company | Stabilized polyphenylene ether resin compositions containing hindered tris-phenols |
| US4184999A (en) * | 1978-07-19 | 1980-01-22 | General Electric Company | Stabilized polyphenylene ether resin compositions containing hindered phenols |
-
1982
- 1982-04-16 CA CA000401171A patent/CA1185726A/en not_active Expired
- 1982-05-04 JP JP50178882A patent/JPS58500718A/en active Pending
- 1982-05-04 EP EP19820901774 patent/EP0078835A4/en not_active Withdrawn
- 1982-05-04 WO PCT/US1982/000576 patent/WO1982004057A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0078835A1 (en) | 1983-05-18 |
| WO1982004057A1 (en) | 1982-11-25 |
| EP0078835A4 (en) | 1983-09-22 |
| JPS58500718A (en) | 1983-05-06 |
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