Polyarylene sulfide and a preparation method thereof

Abstract

The present invention relates to a polyarylene sulfide having more improved miscibility with other polymer materials or fillers, and a method of preparing the same. At least part of end groups of the main chain of the polyarylene sulfide is carboxyl group (COOH) or amine group (NH.sub.2).

Claims

1. A polyarylene sulfide of which at least part of end groups of the main chain is carboxyl group (COOH), and the remainder of the end groups is iodine group or unsubstituted aryl group, wherein the polyarylene sulfide is prepared by a method including the steps of: melt-polymerizing a reactant including a diiodoaromatic compound and elemental sulfur; and adding a compound having carboxyl group while carrying out the melt-polymerization step, wherein the compound having carboxyl group includes one or more compounds selected from the group consisting of 2-iodobenzoic acid, 3-iodobenzoic acid, 4-iodobenzoic acid, and 2,2-dithiobenzoic acid, wherein an FT-IR spectrum of the polyarylene sulfide shows a first peak between 1400 and 1600 cm.sup.1 and a second peak between 1600 and 1800 cm.sup.1, wherein a height intensity of the second peak is between about 0.5% and about 10% of a height intensity of the first peak, and wherein the compound having carboxyl group is added thereto when the degree of the polymerization reaction is progressed 90% or more, wherein the degree of polymerization reaction is determined by the ratio of present viscosity to target viscosity.

2. The polyarylene sulfide according to claim 1, wherein the melting temperature is 265 to 290 C.

3. The polyarylene sulfide according to claim 1, wherein the number average molecular weight is 5,000 to 50,000.

4. The polyarylene sulfide according to claim 1, wherein the melt viscosity measured with a rotational viscometer at 300 C. is 10 to 50,000 poise.

5. The polyarylene sulfide according to claim 1, wherein the tensile strength measured according to ASTM D 638 is 100 to 900 kgf/cm.sup.2.

6. The polyarylene sulfide according to claim 1, wherein the elongation measured according to ASTM D 638 is 1 to 10%.

7. The polyarylene sulfide according to claim 1, wherein the flexural strength measured according to ASTM D 790 is 100 to 2,000 kgf/cm.sup.2.

8. The polyarylene sulfide according to claim 1, wherein the impact strength measured according to ASTM D 256 is 1 to 100 J/m.

9. The polyarylene sulfide according to claim 1, wherein the compound having carboxyl group is added thereto in the amount of 0.0001 to 5 parts by weight, based on 100 parts by weight of the diiodoaromatic compound.

10. The polyarylene sulfide according to claim 1, wherein the diiodoaromatic compound is one more compounds selected from the group consisting of diiodobenzene, diiodonaphthalene, diiodobiphenyl, diiodobisphenol, and diiodobenzophenone.

11. The polyarylene sulfide according to claim 1, wherein polymerizing step is carried out for 1 to 30 hours by varying the temperature and pressure from the initial reaction condition of 180 to 250 C. and 50 to 450 torr to the final reaction condition of 270 to 350 C. and 0.001 to 20 torr.

12. The polyarylene sulfide according to claim 1, wherein the method further includes the step of melt-mixing the reactant including the diiodoaromatic compound and sulfur element, before the polymerizing step.

13. A shaped article, including the polyarylene sulfide according to claim 1.

14. The shaped article according to claim 13, which is a form of film, sheet, or fiber.

Description

DETAILED DESCRIPTION OF THE EMBODIMENT

(1) Hereinafter, preferable examples are presented for understanding the present invention. However, the following examples are only for illustrating the present invention and the present invention is not limited to or by them.

Example 1: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(2) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 51 g of 4-iodobenzoic acid thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(3) The polyarylene sulfide resin of Example 1 was analyzed by FT-IR spectroscopy. At this time, the carboxyl group peak was recognized at about 1600 to 1800 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 1600 to 1800 cm.sup.1 was about 3.4% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 2: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(4) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 51 g of 4-iodoaniline thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(5) The polyarylene sulfide resin of Example 2 was analyzed by FT-IR spectroscopy. At this time, the amine group peak was recognized at about 3300 to 3500 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 3300 to 3500 cm.sup.1 was about 1.4% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 3: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(6) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 25 g of 4-iodobenzoic acid thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(7) The polyarylene sulfide resin of Example 3 was analyzed by FT-IR spectroscopy. At this time, the carboxyl group peak was recognized at about 1600 to 1800 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 1600 to 1800 cm.sup.1 was about 2.1% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 4: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(8) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 25 g of 4-iodoaniline thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(9) The polyarylene sulfide resin of Example 4 was analyzed by FT-IR spectroscopy. At this time, the amine group peak was recognized at about 3300 to 3500 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 3300 to 3500 cm.sup.1 was about 1.1% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 5: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(10) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 51 g of 2,2-dithiodibenzoic acid thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(11) The polyarylene sulfide resin of Example 5 was analyzed by FT-IR spectroscopy. At this time, the carboxyl group peak was recognized at about 1600 to 1800 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 1600 to 1800 cm.sup.1 was about 3.2% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 6: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(12) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 51 g of 4,4-dithiodianiline thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(13) The polyarylene sulfide resin of Example 6 was analyzed by FT-IR spectroscopy. At this time, the amine group peak was recognized at about 3300 to 3500 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 3300 to 3500 cm.sup.1 was about 1.3% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 7: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(14) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 25 g of 2,2-dithiodibenzoic acid thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(15) The polyarylene sulfide resin of Example 7 was analyzed by FT-IR spectroscopy. At this time, the carboxyl group peak was recognized at about 1600 to 1800 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 1600 to 1800 cm.sup.1 was about 1.9% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Example 8: Synthesis of Polyarylene Sulfide Including Carboxyl Group or Amine Group at the End of the Main Chain

(16) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was carried out for 1 hr. Subsequently, after adding 25 g of 4,4-dithiodianiline thereto when the reaction was proceeded 90% and progressing the reaction under nitrogen circumstance for 10 mins, the reaction was further progressed with slowly vacuumizing to 0.5 torr or less for 1 hr, and terminated. By this, the polyarylene sulfide resin having carboxyl group or amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(17) The polyarylene sulfide resin of Example 8 was analyzed by FT-IR spectroscopy. At this time, the amine group peak was recognized at about 3300 to 3500 cm.sup.1 in the spectrum. It was also recognized that the relative height intensity of the peak at about 3300 to 3500 cm.sup.1 was about 1.0% when the height intensity of the ring stretch peak shown at about 1400 to 1600 cm.sup.1 was assumed as 100%.

Comparative Example 1

(18) After completely melting and mixing the reactant including 5,130 g of p-diiodobenzene (p-DIB), 450 g of sulfur, and 4 g of 1,3-diiodo-4-nitrobenzene as a reaction initiator in a 5 L reactor equipped with a thermocouple capable of measuring the inside temperature of the reactor and a vacuum line for nitrogen purging and vacuumizing by heating the same to 180 C., the polymerization reaction was proceeded by carrying out temperature-rising and pressure reducing step by step from the initial reaction condition of 220 C. and 350 torr to the final reaction temperature of 300 C. and the pressure of 1 torr or less. When the polymerization reaction was proceeded 80% (the proceeding degree of the polymerization reaction was identified by the relative viscosity ratio [(present viscosity/target viscosity)*100%], and the present viscosity was measured with a viscometer after taking a sample from the reactor where the polymerization reaction was progressing), 25 g of 2,2-dithiobisbenzothiazole was added thereto as a polymerization inhibitor and the reaction was progressed under nitrogen circumstance for 10 mins, and the reaction was further progressed with slowly vacuumizing to 0.5 torr or less and terminated when the viscosity reached the target viscosity. By this, the polyarylene sulfide resin having neither carboxyl group nor amine group at the end of the main chain was synthesized. The final resin obtained by the reaction was prepared into pellets by using a small strand cutter.

(19) The polyarylene sulfide resin of Comparative Example 1 was analyzed by FT-IR spectroscopy. At this time, it was recognized that there was neither carboxyl group peak nor amine group peak at about 1600 to 1800 cm.sup.1 or about 3300 to 3500 cm.sup.1 in the spectrum.

Comparative Example 2

(20) Product name Z200 of DIC Co., Ltd. in which the polyarylene sulfide made by Macallum process was compounded with an elastomer was used as Comparative Example 2.

Experimental Example 1: Evaluation on Basic Properties of Polyarylene Sulfide

(21) The properties of polyarylene sulfides of Examples 1 to 8 and Comparative Example 1 were evaluated by the following methods:

(22) Melting Temperature (Tm)

(23) By using a differential scanning calorimeter (DSC), after elevating the temperature of the specimen from 30 C. to 320 C. with a scanning speed of 10 C./min and cooling to 30 C., the melting temperature was measured while elevating the temperature from 30 C. to 320 C. again with a scanning speed of 20 C./min.

(24) Number Average Molecular Weight (Mn) and Polydispersity Index (PDI)

(25) After dissolving the polyarylene sulfide in 1-chloronaphthalene at 250 C. for 25 minutes with stirring so as to be 0.4 wt % solution, the polyarylene sulfide was divided in order in the column of a high temperature gel permeation chromatography (GPC) system (210 C.) by flowing the solution with the flow rate of 1 mL/min, and the intensity corresponding to the molecular weight of the divided polyarylene sulfide was measure by using a RI detector. After making a calibration line with a standard specimen (polystyrene) of which the molecular weight was known, the relative number average molecular weight (Mn) and polydispersity index (PDI) of the measure sample was calculated.

(26) Melt Viscosity (Poise)

(27) The melt viscosity (hereinafter, M.V.) was measured at 300 C. by using a rotating disk viscometer. In frequency sweep measuring method, angular frequency was measured from 0.6 to 500 rad/s, and the viscosity at 1.84 rad/s was defined as the melt viscosity (M.V.).

(28) The properties measured according to above methods are listed in the following Table 1:

(29) TABLE-US-00001 TABLE 1 Number Melting Average Polydispersity Melt temperature Molecular Index Viscosity Classification ( C.) Weight (PDI) (Poise) Example 1 278.6 17,667 2.9 2,940 Example 2 278.3 17,614 2.9 2,200 Example 3 278.8 17,435 2.8 2,830 Example 4 278.6 17,224 2.8 2,770 Example 5 277.5 17,338 2.9 2,350 Example 6 277.7 17,152 2.9 2,930 Example 7 278.3 17,531 2.8 2,470 Example 8 278.7 17,582 2.8 2,530 Comparative 280.5 17,267 2.8 2,420 Example 1

Experimental Example 2: Evaluation on Mechanical Properties of Polyarylene Sulfide

(30) The mechanical properties of polyarylene sulfides of Examples 1 to 8 and Comparative Example 1 were evaluated by the following methods:

(31) Tensile Strength and Elongation

(32) The tensile strength and the elongation of the polyarylene sulfide specimens prepared according to Examples 1 to 8 and Comparative Example 1 were measured according to ASTM D 638 method.

(33) Flexural Strength

(34) The flexural strength of the polyarylene sulfide specimens prepared according to Examples 1 to 8 and Comparative Example 1 were measured according to ASTM D 790 method.

(35) Impact Strength (Izod)

(36) The impact strength of the polyarylene sulfide specimens prepared according to Examples 1 to 8 and Comparative Example 1 was measured according to ASTM D 256 method.

(37) The mechanical properties measured according to above methods are listed in the following Table 2:

(38) TABLE-US-00002 TABLE 2 Impact Tensile Flexural Strength Strength Elongation Strength (J/m, Classification (kgf/cm.sup.2) (%) (kgf/cm.sup.2) Notched) Example 1 612 2.2 1,430 17 Example 2 602 1.2 1,422 20 Example 3 622 2.1 1,433 18 Example 4 614 1.3 1,442 17 Example 5 628 2.2 1,455 18 Example 6 605 1.2 1,428 17 Example 7 611 2.3 1,435 17 Example 8 618 1.3 1,447 19 Comparative 605 1.2 1,453 19 Example 1

(39) The specimens were prepared by compounding the polyarylene sulfide of Examples 1 to 8 and Comparative Example 1 with other components according to the following methods:

(40) Compounding of Polyarylene Sulfide and Glass Fiber (GF)

(41) After drying the polymerized resin, the compounding was carried out with a small twin-screw extruder under the condition of the extrusion die temperature of 300 C. and the screw speed of 200 rpm while adding 40 parts by weight of glass fiber to 60 parts by weight of the resin.

(42) Compounding of Polyarylene Sulfide and Elastomer

(43) The mixing extrusion was carried out under the condition of the extrusion die temperature of 300 C. and the screw speed of 200 rpm while adding 10 parts by weight of Lotader (Grade AX-8840, made by Arkema), the elastomer, to 90 parts by weight of the resin.

(44) The mechanical properties of the compounded specimens were evaluated by the same way as the polyarylene sulfide specimens and are listed in the following Table 3. Furthermore, the properties of the specimen of Comparative Example 2, a commercialized compounded specimen, are compared with Examples and Comparative Example 1 in the following Table 3:

(45) TABLE-US-00003 TABLE 3 Tensile Flexural Impact Strength Elongation Strength Strength Classification (kgf/cm.sup.2) (%) (kgf/cm.sup.2) (J/m, Notched) Example 1 + 583 25.2 1,030 54 Elastomer 10% Example 2 + 1,750 1.8 2,440 85 GF 40% Example 3 + 577 20.5 1,010 48 Elastomer 10% Example 4 + 1,740 1.8 2,400 83 GF 40% Example 5 + 564 24.3 1,010 52 Elastomer 10% Example 6 + 1,770 1.8 2,480 86 GF 40% Example 7 + 568 18.7 1,005 45 Elastomer 10% Example 8 + 1,750 1.8 2,420 82 GF 40% Comparative 556 2.5 950 17 Example 1 + Elastomer 10% Comparative 1,700 1.7 2,300 77 Example 1 + GF 40% Comparative 660 15.7 940 76 Example 2

(46) According to Tables 2 and 3, it was recognized that the elongation was elevated about 10 times from about 2.2% to about 25.2 and the impact strength was elevated about 3 times from about 17 J/m to about 54 J/m by compounding the polyarylene sulfide of Example 1 of which carboxyl group is introduce to the end of the main chain with the thermoplastic elastomer. And, it was recognized that the tensile strength was largely elevated from about 602 kgf/cm.sup.2 to about 1750 kgf/cm.sup.2 by compounding the polyarylene sulfide of Example 2 of which amine group is introduced to the end group of the main chain with glass fiber. Therefore, it can be known from the properties elevated by such compounding that the polyarylene sulfides of Examples can show good compatibility with other various polymer materials or fillers, and consequently can exhibit excellent synergistic effects.

(47) On the other hand, it was recognized that the polyarylene sulfide of Comparative Example 1 was inferior in the compatibility with other polymer materials or fillers and the synergistic effects caused by compounding was not so big.

(48) Furthermore, the compounded specimen of Comparative Example 2 was a commercialized specimen prepared by compounding the polyarylene sulfide which was obtained by Macallum process and was known to be good in the compatibility with other polymer materials and several % of elastomer. However, such compounded specimen of Comparative Example 2 also showed not enough elongation improvement by compounding with elastomer, in comparison with Examples, and it seems to have the problems (deterioration in processability and workability due to the powder form) of polyarylene sulfide obtained by Macallum process.