CA2020935A1 - Polyphenylene ether molding composition - Google Patents
Polyphenylene ether molding compositionInfo
- Publication number
- CA2020935A1 CA2020935A1 CA002020935A CA2020935A CA2020935A1 CA 2020935 A1 CA2020935 A1 CA 2020935A1 CA 002020935 A CA002020935 A CA 002020935A CA 2020935 A CA2020935 A CA 2020935A CA 2020935 A1 CA2020935 A1 CA 2020935A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- polyphenylene ether
- molding composition
- radical
- phosphorus compound
- 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.)
- Abandoned
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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
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)
- Injection Moulding Of Plastics Or The Like (AREA)
Abstract
Abstract of the disclosure Polyphenylene ether molding composition In the case of polyphenylene ethers, in particular polyphenylene sulfide, the addition of a small amount of an organic phosphorus compound of the formulae II, III or IV inhibits crystallization and depresses the crystal-lization temperature in the melt.
(II) (III)
(II) (III)
Description
~ ~ ~ v ..~ 3 ~
HOECHST ARTIENGESELLSCHAFT HOE 89/F 225 Dr.DA/je Description Polyphenylene ether molding composition The invention relates to a polyphenylene ether molding composition which contains, to inhibit crystallization, certain organic phosphorus compounds.
Polyphenylene ethers, in particular polyphenylene 6ul-fide, number among the highly c~rstalline polymers, owing to their linear struc~ure. Under normal processing, crystallization occurs very rapidly and, among other effects, prevents transparent articles being produced from these polymers. ~oreover, the high crystallization rate interferes with processes in which molecular orien-tations, for example during stretching, play a part.
Inhibited crystalli~ation would be advantageous, in particular in the production of fibers and films, since then a wider processing range would be available in the amorphous region.
Many proposals have already been made for controlling the crystallization of highly crystalline polymers using crystallization inhibitors.
~or instance, a process for the crystalliza ion of polyarylene sulfide has been disclosed in which the polymer is treated with polyvalent metal cations, prefer-ably in aqueous solution (cf. European Patent 144,987).
Although this treatment depresses the crystallization temperature in the melt and reduces the crystallization rate, an additional process st~p using aqueous solutions is at the same time necessary.
The object is therefore to provide an agent for inhibit-ing the crystallization of polyphenylene ethers, which can be incorporated into ~he polymer at low cost.
: , :
.
HOECHST ARTIENGESELLSCHAFT HOE 89/F 225 Dr.DA/je Description Polyphenylene ether molding composition The invention relates to a polyphenylene ether molding composition which contains, to inhibit crystallization, certain organic phosphorus compounds.
Polyphenylene ethers, in particular polyphenylene 6ul-fide, number among the highly c~rstalline polymers, owing to their linear struc~ure. Under normal processing, crystallization occurs very rapidly and, among other effects, prevents transparent articles being produced from these polymers. ~oreover, the high crystallization rate interferes with processes in which molecular orien-tations, for example during stretching, play a part.
Inhibited crystalli~ation would be advantageous, in particular in the production of fibers and films, since then a wider processing range would be available in the amorphous region.
Many proposals have already been made for controlling the crystallization of highly crystalline polymers using crystallization inhibitors.
~or instance, a process for the crystalliza ion of polyarylene sulfide has been disclosed in which the polymer is treated with polyvalent metal cations, prefer-ably in aqueous solution (cf. European Patent 144,987).
Although this treatment depresses the crystallization temperature in the melt and reduces the crystallization rate, an additional process st~p using aqueous solutions is at the same time necessary.
The object is therefore to provide an agent for inhibit-ing the crystallization of polyphenylene ethers, which can be incorporated into ~he polymer at low cost.
: , :
.
2 ~ i Y.li ~ ~
It has been found that this object can be achieved by using certain organic phosphorus compounds.
The present i~vention accordingly provides a polyphenyl-ene ether molding composition essentially composed of a S polymer which contains units of the formula I
Rl _ [ ~ X~
in which Rl and R2 are identical or different and are a hydrogen atom or a straight-chain or branched Cl-C4-alkyl radical and O X i8 an oxygen atom or a sulfur atom, and a crystallization inhibitor, wherein the molding composi-tion contains 0.05 to 5 parts by weight, rela~ive to the polymer, of an organic phosphorus compound of the formula II
\ ~ R5 (II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more Cl-C4-alkyl groups, of the formula III
R7 o/ ~ P\ (III) in which R6, R7, R3 and R9 have the meaning, of R3, R4 and , -:, . .
-- ~ . .... . -.. :. ~- .
R5, or of the formula IV
R10 0 P ~ --R12 ~' ~ P - O - Rll \ o ~ ~ (IV) in which Rl and R11 are identical or different and are a S straight-chain C~-C22-alkyl radical or a phenyl radical which may be substituted by one or more Cl-C4-alkyl groups, and Rl2 iS a pentaerythrityl radical.
The polyphenylene ether molding composition according ~o the invention is essentially composed of a polymer which contains units of the formula I
~ X ~ (I) In this formula, R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched Cl-C4-alkyl radical. Rl and R2 are preferably a hydrogen atom or a C1-C2-alkyl radical, in particular a hydrogen atom or a methyl group. X is an oxygen atom or a ~ulfur atom, preferably a sulfur stom. The polymer is preferably composed entirely of units of the formula I. The mole-cular weight is generally about 5,000 to about 200,000, correspondin~ to 20 to 2,000 units of the formula I.
Suitable polyphenylene ethers are poly(thio-l,4-phenyl-ene~ and poly(2,6-dimethyl-1,4-phenylene ether). Part-icular preference i8 given to polyphenylene sulfide.
Polymers of this type are commercially available even unstabili~ed and free from other additives. However, they .. . .
., - . . :-: . -.: - . : -. -, , . . . , ~
?~ L,'`'`~
can also be prepared by the process according to European Patent 144,987.
The molding composition according to the invention contains 0.05 to 5, preferably 0.1 to 1, part~ by weight, relative to the polymer, of a cr~stallization inhibitor.
This crystallization inhibitor is an organic phosphorus compound of the formulae II, III or IV:
O
P~3 _ o _ p/
\0 - R5 (II) R6 o\ ~{3 8 ( III ) R - O - P~ R12~ \P - O - Rll ( IV) In these formulae R3, R4, R5, R6, R7, R~ and R9 are identi-cal or different and are a phenyl radical which may be substituted by one or more Cl-C4-, preferably branched C4-, alkyl groups. R3, R4, R5, R6, R7, R8 and R9 are prefer-ably a 2,4-di-t-butylphenyl group.
Rl and R11 are identical or different and are a C12-C22-, preferably Cl8-Cl~-, alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-, preferab~y branched C4-, alkyl radicals. Preferably, R10 and R11 are ~0 a stearyl rad~ical or a 2,4-di-t-butylphe~yl group.
Rl2 is a pentaerythrityl radical.
:
, . ~ ~ :`
. .
;~ v f~
Particularly preferred phosphorus compvunds are tris-(2,4-di-t-butylphenyl) phosphite and tetrakis-(2,4-di-t-butylphenyl) 4,4'-bisphenylenediphosphonite.
Besides the phosphorus compounds which are to be used according to the invention, the polyphenylene ether molding composition may addil:ionally contain anti-oxidants, ~V absorbers, light stabilizers, metal de-activa~ors, stabilizers, fillers, reinforcing agents, lubricants, pigments, optical bxighteners, flame retar-dants or antistatic agents.
The incorporation of the phosphorus compounds into thepolyphenylene etheræ is carried out by the usual plastic compounding procedures. ~or instance, the phosphorus compounds can be incorporated in the form of pulverulent solids wi~h the plastic powder or granules or can be metered in in the form of a concentrate containing up to 50 % by weight of active ingredient or in the form of a dispersion or emulsion in a suitable dispersing agent which is subsequently removed.
The addition of the phosphorus compounds of the formulae II, III or IV allows crystallization to be significantly delayed. Moreover, these oompounds additionally act as heat stabiliæers.
The invention is explained using the following example.
Example Polyphenylens sulfide (density 1.34 g/cm3~ m.p. 283C) was dried in a vacuum drying oven for 12 h at 14GC. A
slowly rotating stirrer was used to admix 0.5 parts by weight of the pulverulent phosphorus ~ompound 1 or 2 per 100 parts by weight of the pulverulent polyphenylene sulfide. These mixtures were used to prepare platelets of dimensions 1 x 60 x 60 mm on an injection molding machine (temperature profile 300-310-320-330C; mold temperature .: : : ,. .
. .
.
.. . . :...... . .. . , - .
- 6 - 2 $ ~, t, " ~ ~
100C). ~he crystallinity was assessed by measuring the transparency of the test pieces using a transparency meter (type LT12/Dr. B. Lange, Berlin). The crystalliz-ation process was investigated using differential scan-ning calorimetry (DSC) and not only the post-crystallization during the first heating step was moni-tored but also the crystallization during the defined cooling of the sample.
DSC conditions:
Temperature range: 10C - 310C
Heating/cooling rate: 10 K/min Purging: nitrogen Sample size: in the range of 6-7 mg Measuring apparatus: ~ettler type TA 3000 15 The results of the measurements are summarized in the table.
Phosphorus compound 1 = tris-(2,4-di-t-butylphenyl~
phosphite C(CH3)3 p _ O ~C ( CH3 ) 3 3 Phosphorus compound 2 = tetrakis-(2,4-di-t-butylphenyl) 4,4'~biphenylenediphosphonite R o/ ~ /O R R _ ~ C(CH3~3 , .
~ .
7 ~ ? j ' ~
~xperimental result~
a) Post-crystallization during the initial heating step Despite the high crystallinity of polyphenylene sulfide, complete crystallization does not occur during in~ection molding. Consequently, post-crystallization can be observed at a higher temperature in the DSC.
Pure PPS has a pos~-crystallizaltion peak at 120C. On adding phosphorus compound 1, this crystallization peak is observed at 127C. Phosphorus compound 2 shift~ the ~0 post-crystallization peak to 12~C.
The greater liberated heat flows from each of the modi-fied types is likewise evidence of lower crystallinity.
b) Crystallization during cooling To investigate this crystallization, the polymer melts are cooled in a defined manner.
The unmodified PPS has a crystalli~ation peak maximum at 246C. ~he sample modified with phosphorus compound 1 has a peak maximum which is 30 g l~wer, i.e~ the crystalliz-ation peak maxLmum is at 216~C.
c) Transparency The addition of 0.5 part of the organic phosphorus com-pound used allows 1 mm test platelets to be obtained having a light transmission of up to 60 %. The unmodified test pieces are opaque after processing.
'- :,. . ~ :, ,~
., ~ , .
- 8 - 2 $ 2 ~ l3 3 ~
Table Results of the DSC analysis PPS PPS PPS
without + 0.5 part ~ 0.5 part additive of phosphorus of phosphorus compound 1 compound 2 1. Heating Post-crystalliz-ation Beginning C 100 108 107 Maximum C 120 127 129 End C 130 142 144 Heat transfer J/g 11.5 29.0 27.0 Melting temp.
Maximum C 283 283 284 Heat of fusion J/g 45 44 47 .
Cooling 20 Crystallization Beginning C 260 237 249 Maximum C 246 216 233 End 200 192. 202 Heat transfer J/g 51 49 52 Transparencyopaque 60.6 4~.5 % transmission .
- .
It has been found that this object can be achieved by using certain organic phosphorus compounds.
The present i~vention accordingly provides a polyphenyl-ene ether molding composition essentially composed of a S polymer which contains units of the formula I
Rl _ [ ~ X~
in which Rl and R2 are identical or different and are a hydrogen atom or a straight-chain or branched Cl-C4-alkyl radical and O X i8 an oxygen atom or a sulfur atom, and a crystallization inhibitor, wherein the molding composi-tion contains 0.05 to 5 parts by weight, rela~ive to the polymer, of an organic phosphorus compound of the formula II
\ ~ R5 (II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more Cl-C4-alkyl groups, of the formula III
R7 o/ ~ P\ (III) in which R6, R7, R3 and R9 have the meaning, of R3, R4 and , -:, . .
-- ~ . .... . -.. :. ~- .
R5, or of the formula IV
R10 0 P ~ --R12 ~' ~ P - O - Rll \ o ~ ~ (IV) in which Rl and R11 are identical or different and are a S straight-chain C~-C22-alkyl radical or a phenyl radical which may be substituted by one or more Cl-C4-alkyl groups, and Rl2 iS a pentaerythrityl radical.
The polyphenylene ether molding composition according ~o the invention is essentially composed of a polymer which contains units of the formula I
~ X ~ (I) In this formula, R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched Cl-C4-alkyl radical. Rl and R2 are preferably a hydrogen atom or a C1-C2-alkyl radical, in particular a hydrogen atom or a methyl group. X is an oxygen atom or a ~ulfur atom, preferably a sulfur stom. The polymer is preferably composed entirely of units of the formula I. The mole-cular weight is generally about 5,000 to about 200,000, correspondin~ to 20 to 2,000 units of the formula I.
Suitable polyphenylene ethers are poly(thio-l,4-phenyl-ene~ and poly(2,6-dimethyl-1,4-phenylene ether). Part-icular preference i8 given to polyphenylene sulfide.
Polymers of this type are commercially available even unstabili~ed and free from other additives. However, they .. . .
., - . . :-: . -.: - . : -. -, , . . . , ~
?~ L,'`'`~
can also be prepared by the process according to European Patent 144,987.
The molding composition according to the invention contains 0.05 to 5, preferably 0.1 to 1, part~ by weight, relative to the polymer, of a cr~stallization inhibitor.
This crystallization inhibitor is an organic phosphorus compound of the formulae II, III or IV:
O
P~3 _ o _ p/
\0 - R5 (II) R6 o\ ~{3 8 ( III ) R - O - P~ R12~ \P - O - Rll ( IV) In these formulae R3, R4, R5, R6, R7, R~ and R9 are identi-cal or different and are a phenyl radical which may be substituted by one or more Cl-C4-, preferably branched C4-, alkyl groups. R3, R4, R5, R6, R7, R8 and R9 are prefer-ably a 2,4-di-t-butylphenyl group.
Rl and R11 are identical or different and are a C12-C22-, preferably Cl8-Cl~-, alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-, preferab~y branched C4-, alkyl radicals. Preferably, R10 and R11 are ~0 a stearyl rad~ical or a 2,4-di-t-butylphe~yl group.
Rl2 is a pentaerythrityl radical.
:
, . ~ ~ :`
. .
;~ v f~
Particularly preferred phosphorus compvunds are tris-(2,4-di-t-butylphenyl) phosphite and tetrakis-(2,4-di-t-butylphenyl) 4,4'-bisphenylenediphosphonite.
Besides the phosphorus compounds which are to be used according to the invention, the polyphenylene ether molding composition may addil:ionally contain anti-oxidants, ~V absorbers, light stabilizers, metal de-activa~ors, stabilizers, fillers, reinforcing agents, lubricants, pigments, optical bxighteners, flame retar-dants or antistatic agents.
The incorporation of the phosphorus compounds into thepolyphenylene etheræ is carried out by the usual plastic compounding procedures. ~or instance, the phosphorus compounds can be incorporated in the form of pulverulent solids wi~h the plastic powder or granules or can be metered in in the form of a concentrate containing up to 50 % by weight of active ingredient or in the form of a dispersion or emulsion in a suitable dispersing agent which is subsequently removed.
The addition of the phosphorus compounds of the formulae II, III or IV allows crystallization to be significantly delayed. Moreover, these oompounds additionally act as heat stabiliæers.
The invention is explained using the following example.
Example Polyphenylens sulfide (density 1.34 g/cm3~ m.p. 283C) was dried in a vacuum drying oven for 12 h at 14GC. A
slowly rotating stirrer was used to admix 0.5 parts by weight of the pulverulent phosphorus ~ompound 1 or 2 per 100 parts by weight of the pulverulent polyphenylene sulfide. These mixtures were used to prepare platelets of dimensions 1 x 60 x 60 mm on an injection molding machine (temperature profile 300-310-320-330C; mold temperature .: : : ,. .
. .
.
.. . . :...... . .. . , - .
- 6 - 2 $ ~, t, " ~ ~
100C). ~he crystallinity was assessed by measuring the transparency of the test pieces using a transparency meter (type LT12/Dr. B. Lange, Berlin). The crystalliz-ation process was investigated using differential scan-ning calorimetry (DSC) and not only the post-crystallization during the first heating step was moni-tored but also the crystallization during the defined cooling of the sample.
DSC conditions:
Temperature range: 10C - 310C
Heating/cooling rate: 10 K/min Purging: nitrogen Sample size: in the range of 6-7 mg Measuring apparatus: ~ettler type TA 3000 15 The results of the measurements are summarized in the table.
Phosphorus compound 1 = tris-(2,4-di-t-butylphenyl~
phosphite C(CH3)3 p _ O ~C ( CH3 ) 3 3 Phosphorus compound 2 = tetrakis-(2,4-di-t-butylphenyl) 4,4'~biphenylenediphosphonite R o/ ~ /O R R _ ~ C(CH3~3 , .
~ .
7 ~ ? j ' ~
~xperimental result~
a) Post-crystallization during the initial heating step Despite the high crystallinity of polyphenylene sulfide, complete crystallization does not occur during in~ection molding. Consequently, post-crystallization can be observed at a higher temperature in the DSC.
Pure PPS has a pos~-crystallizaltion peak at 120C. On adding phosphorus compound 1, this crystallization peak is observed at 127C. Phosphorus compound 2 shift~ the ~0 post-crystallization peak to 12~C.
The greater liberated heat flows from each of the modi-fied types is likewise evidence of lower crystallinity.
b) Crystallization during cooling To investigate this crystallization, the polymer melts are cooled in a defined manner.
The unmodified PPS has a crystalli~ation peak maximum at 246C. ~he sample modified with phosphorus compound 1 has a peak maximum which is 30 g l~wer, i.e~ the crystalliz-ation peak maxLmum is at 216~C.
c) Transparency The addition of 0.5 part of the organic phosphorus com-pound used allows 1 mm test platelets to be obtained having a light transmission of up to 60 %. The unmodified test pieces are opaque after processing.
'- :,. . ~ :, ,~
., ~ , .
- 8 - 2 $ 2 ~ l3 3 ~
Table Results of the DSC analysis PPS PPS PPS
without + 0.5 part ~ 0.5 part additive of phosphorus of phosphorus compound 1 compound 2 1. Heating Post-crystalliz-ation Beginning C 100 108 107 Maximum C 120 127 129 End C 130 142 144 Heat transfer J/g 11.5 29.0 27.0 Melting temp.
Maximum C 283 283 284 Heat of fusion J/g 45 44 47 .
Cooling 20 Crystallization Beginning C 260 237 249 Maximum C 246 216 233 End 200 192. 202 Heat transfer J/g 51 49 52 Transparencyopaque 60.6 4~.5 % transmission .
- .
Claims (7)
1. A polyphenylene ether molding composition essen-tially composed of a polymer which contains units of the formula I
( I ) in which R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched C1-C4-alkyl radical and X is an oxygen atom or a sulfur atom, and a crystallization inhibitor, wherein the molding composition contains 0.05 to 5 parts by weight, relative to the polymer, of an organic phosphorus compound of the formula II
[II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more straight-chain or branched C1-C4-alkyl groups, of the formula III
( III ) in which R6, R7, R8 and R9 have the meanings of R3, R4 and R5, or of the formula IV
(IV) in which R10 and R11 are identical or different and are a C12-C22-alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-alkyl groups, and R12 is a pentaerythrityl radical.
( I ) in which R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched C1-C4-alkyl radical and X is an oxygen atom or a sulfur atom, and a crystallization inhibitor, wherein the molding composition contains 0.05 to 5 parts by weight, relative to the polymer, of an organic phosphorus compound of the formula II
[II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more straight-chain or branched C1-C4-alkyl groups, of the formula III
( III ) in which R6, R7, R8 and R9 have the meanings of R3, R4 and R5, or of the formula IV
(IV) in which R10 and R11 are identical or different and are a C12-C22-alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-alkyl groups, and R12 is a pentaerythrityl radical.
2. A polyphenylene ether molding composition as claimed in claim 1, wherein the polyphenylene ether is a polyphenylene sulfide.
3. A polyphenylene ether molding composition as claimed in claim 1, wherein the organic phosphorus compound is a compound of the formula II.
4. A polyphenylene ether molding composition as claimed in claim 1, wherein the organic phosphorus compound is a compound of the formula III.
5. A polyphenylene ether molding composition as claimed in claim 1, wherein the organic phosphorus compound is tris-(2,4-di-t-butylphenyl) phosphite.
6. A polyphenylene ether molding composition as claimed in claim 1, wherein the organic phosphorus compound is tetrakis-(2,4-di-t-butylphenyl)4,4'-biphenylene-diphosphonite.
7. A process for inhibiting the crystallization of a polyphenylene ether which contains units of the formula I
(I) in which R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched C1-C4-alkyl radical and X is an oxygen atom or sulfur atom, by incorporating a crystallization inhibitor into the molten polymer, which comprises incorporating into the polymer 0.5 to 5 parts by weight, relative to the polymer, of an organic phosphorus compound of the formula II
( II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more C1-C4-alkyl groups, of the formula III
(III) in which R6, R7, R8 and R9 have the meanings of R3, R4 and R5, or of the formula IV
(IV) in which R10 and R11 are identical or different and are a C12-C22-alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-alkyl groups, and R12 is a pentaerythrityl radical.
(I) in which R1 and R2 are identical or different and are a hydrogen atom or a straight-chain or branched C1-C4-alkyl radical and X is an oxygen atom or sulfur atom, by incorporating a crystallization inhibitor into the molten polymer, which comprises incorporating into the polymer 0.5 to 5 parts by weight, relative to the polymer, of an organic phosphorus compound of the formula II
( II) in which R3, R4 and R5 are identical or different and are a phenyl radical, which may be substituted by one or more C1-C4-alkyl groups, of the formula III
(III) in which R6, R7, R8 and R9 have the meanings of R3, R4 and R5, or of the formula IV
(IV) in which R10 and R11 are identical or different and are a C12-C22-alkyl radical or a phenyl radical which may be substituted by one or more C1-C4-alkyl groups, and R12 is a pentaerythrityl radical.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3922901.7 | 1989-07-12 | ||
| DE3922901A DE3922901A1 (en) | 1989-07-12 | 1989-07-12 | POLYPHENYLENETHERFORMMASSE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2020935A1 true CA2020935A1 (en) | 1991-01-13 |
Family
ID=6384805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002020935A Abandoned CA2020935A1 (en) | 1989-07-12 | 1990-07-11 | Polyphenylene ether molding composition |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0407926B1 (en) |
| JP (1) | JPH0352948A (en) |
| KR (1) | KR0169309B1 (en) |
| BR (1) | BR9003317A (en) |
| CA (1) | CA2020935A1 (en) |
| DE (2) | DE3922901A1 (en) |
| HK (1) | HK1007154A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5185392A (en) * | 1989-06-27 | 1993-02-09 | Polyplastics Co., Inc. | Polyarylene sulfide resin composition |
| GB2263280B (en) * | 1992-01-17 | 1996-07-31 | Sandoz Ltd | Use of a phosphonite and optionally a phosphite for clarifying propylene polymers |
| JP2525319B2 (en) * | 1992-04-08 | 1996-08-21 | チッソ株式会社 | Crystalline polyolefin composition |
| JPH0733974A (en) * | 1993-07-16 | 1995-02-03 | Mitsubishi Chem Corp | Thermoplastic resin composition |
| DE102016225777A1 (en) | 2016-12-21 | 2018-06-21 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Process for lowering the crystallization temperature of partially crystalline polyamides, polyamide molding composition produced thereby and use of polyfunctional transesterifiable organic phosphonites, organic phosphites, organic phosphates or mixtures thereof for lowering the crystallization temperature, for crosslinking and / or branching of partially crystalline polyamides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3170981D1 (en) * | 1980-03-10 | 1985-07-25 | Mitsubishi Gas Chemical Co | Polyphenylene ether resin composition of improved heat stability and shaped articles thereof |
| US4892930A (en) * | 1988-07-29 | 1990-01-09 | Phillips Petroleum Company | Method for lowering the melt crystallization temperature of an arylene sulfide polymer with organic phosphite composition |
-
1989
- 1989-07-12 DE DE3922901A patent/DE3922901A1/en not_active Withdrawn
-
1990
- 1990-07-07 DE DE59008284T patent/DE59008284D1/en not_active Expired - Fee Related
- 1990-07-07 EP EP90113036A patent/EP0407926B1/en not_active Expired - Lifetime
- 1990-07-10 JP JP2180740A patent/JPH0352948A/en active Pending
- 1990-07-10 KR KR1019900010381A patent/KR0169309B1/en not_active IP Right Cessation
- 1990-07-11 BR BR909003317A patent/BR9003317A/en unknown
- 1990-07-11 CA CA002020935A patent/CA2020935A1/en not_active Abandoned
-
1998
- 1998-06-24 HK HK98106334A patent/HK1007154A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3922901A1 (en) | 1991-01-17 |
| EP0407926B1 (en) | 1995-01-18 |
| BR9003317A (en) | 1991-08-27 |
| HK1007154A1 (en) | 1999-04-01 |
| DE59008284D1 (en) | 1995-03-02 |
| KR0169309B1 (en) | 1999-03-20 |
| JPH0352948A (en) | 1991-03-07 |
| EP0407926A1 (en) | 1991-01-16 |
| KR910003015A (en) | 1991-02-26 |
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