NL8102633A - POLYPHENYLENE ETH RESIN CONTAINING FORM MATERIALS. - Google Patents

Description

S 2348-1130 Ned. * ’* P & c

Polyphenylene ether resin containing sparking materials.

The polyphenylene ether resins include a known group of polymers that can be prepared by a variety of catalytic and non-catalytic methods, such as described, for example, in U.S. Pat. Nos. 3,306,874, 3,306,875, 3,257,357, 3,257,358, 3,356,761 , 3,337,499, 3,219,626, 3,384,619, 3,440,217, 3,442,885, 3,573,257, 3,455,880, and 3,382,212.

U.S. Patent 3,383,435 describes compositions of polyphenylene ether resins and styrene resins, including halogenated styrene resins. U.S. Pat. No. 3,887,646 describes compositions of a polyphenylene ether resin and a chlorostyrene resin. U.S. Patent 3,629,506 describes compositions of a polyphenylene ether resin containing a styrene resin, a phosphate and a halogenated flame retardant.

It has been found that compositions of a polyphenylene ether resin and a copolymer of styrene and bromostyrene have better stability to ultraviolet rays than compositions with brominated low molecular weight additives, are inherently flame retardant and require little or no further flame retardant additive to an acceptable degree of flame retardancy. Furthermore, it has been found that copolymers of styrene and bromostyrene are compatible with polyphenylene ether resins, while 100% bromostyrene polymers in combination with polyphenylene ether resins exhibit phase separation. It has been found that a copolymer having a bromine styrene to styrene ratio of 85:15 is miscible with polyphenylene ether:. in a 75:25 ratio between polyphenylene ether and bromostyrene copolymer, while a 50:50 polyphenylene ether: bromostyrene copolymer composition having a bromostyrene-styrene ratio of 85:15 or the polymer of bromostyrene alone forms two phases. A copolymer with a bromostyrene: styrene ratio of 70:30 is compatible in all proportions with poly-phenylene ether resins, as well as bromostyrene copolymers with less than 70% bromostyrene. The same degree of compatibility for the bromostyrene-styrene copolymer is to be expected in the lower part of the concentration range.

The compositions containing the bromostyrene copolymer can be extruded and formed without discoloration. They have a higher deformation temperature and better fire resistance than analogous polyphenylene ether resin containing compositions prepared with polystyrene.

8102633 f * s - 2 -

The bromine present in the styrene-bromostyrene copolymer has proved more effective as a flame retardant than an equivalent amount of bromine which is incorporated as a low molecular weight flame retardant in analogous polyphenylene ether-styrene resin compositions.

It has also been found that bromine in the form of a bromostyrene-styrene copolymer when tested in the presence of a polyphenylene ether resin is more stable to the deterioration effects of ultraviolet rays than a low molecular weight bromine compound such as decabromodiphenyl ether. It has further been found that compositions of a polyphenylene ether resin and a copolymer of styrene and bromostyrene are more stable to ultraviolet discoloration than compositions of a polyphenylene ether and a homopolystyrene.

The compositions of the invention contain: (a) a polyphenylene ether resin; and (b) a copolymer of styrene and bromostyrene.

The polyphenylene ether resins are polymers of the formula (1) of the formula sheet wherein Q is a hydrogen atom, hydrocarbon group, halohydrocarbon group having at least two carbon atoms between the halogen atom and the phenyl core, hydrocarbon oxy group or halogen hydrocarbon oxy group having at least two carbon atoms between the halogen atom and the phenyl core proposes; each of the symbols Q 'and Q "has the same meanings as given above for Q and may further represent a halogen atom, with the proviso that Q and Q' are both free of tertiary carbon atoms; and n a number with a value of at least 50.

The preferred polyphenylene ether resin is a poly (2,6-dimethyl-1,4-phenylene) ether resin with an intrinsic viscosity of about 0.40-0.60 dl / g, determined in chloroform at 30 ° C.

The styrene-bromostyrene copolymers can be prepared from styrene and bromostyrene. Furthermore, isomeric mixtures of bromostyrene can be used which may contain para, meta and ortho-bromostyrene.

In general, the weight ratio of styrene to bromostyrene in the copolymer can range from 15:85 to 85:15; preferably this ratio is 30: 70-85: 15.

80-10 parts by weight of the styrene-bromostyrene copolymer can be combined in combination with 20-90 parts by weight. use polyphenylene ether resin.

These copolymers can be prepared by various known methods, including free radical polymerization, 4Ό polymerization en mass, suspension polymerization and emulsion polymerization.

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These copolymers are obtained from Makhteshim Chemical Co. as copolymers with 26.6 wt% bromine and 30.4 wt% bromine.

1-15 parts by weight can be used in the compositions of the invention. of a thermoplastic rubber, such as an ABA or AB block copolymer. Suitable ABA block copolymers are the Kraton and Kraton-G polymers described in U.S. Pat. No. 3,646,162 and U.S. Pat. No. 3,595,942, respectively.

If desired, reinforcing amounts of reinforcing fillers can be added to the compositions in amounts of 5-40% by weight of the total composition. As reinforcing fillers, glass fibers or other reinforcing agents, such as quartz, mica, wollastonite or carbon fibers, can be used.

If the amount of bromine in the compositions of the invention is insufficient to achieve the desired degree of flame retardancy, a small amount of a phosphorus compound, ie, 0.1-7.5 parts by weight of a phosphorus compound, can be calculated as elemental phosphorus per 100 parts by weight of the total composition are added.

The preferred phosphorus containing materials can generally be selected from elemental phosphorus and organic phosphonic acids, phosphonates, phosphienates, phosphonites, phosphinites, phosphine oxides, phosphines, phosphites and phosphates. An example of this is triphenylphosphienoxide. These materials may or may not be used in combination with antimony oxide.

Representative phosphorus compounds preferred according to the invention are those of the general formula (2) of the formula sheet, in which each of the symbols Q (which may represent the same or different groups) represents a hydrocarbon group (eg alkyl, cycloalkyl, aryl) by alkyl-substituted aryl or aryl-substituted alkyl), halogen or hydrogen atom, with the proviso that at least one of the symbols Q represents an aryl group. Representative examples of suitable phosphates are phenyl bis-dodecyl phosphate, phenylethyl hydrophosphate, ethyl diphenyl phosphate, 2-ethylhexyl di (p-tolyl) phosphate, diphenyl hydrophosphate, tricresyl phosphate, triphenyl phosphate, 2-chloroethyl phosphate. The preferred phosphates are those commercially available, such as Kronitex-50, a mixture of isomers of tri-propylphenyl phosphate.

The compositions can be prepared by the components in the form of powder, pearls or extruded granules, with or without suitable reinforcing agents, stabilizers, pigments, non-reinforcing 81 02 633-4% fillers, e.g. 5-50% by weight ( based on the total composition) to subject clay, beam, flame retardants, plasticizers or extruders to a tumbling treatment.

The compositions can be obtained by extruding the components 5 into a continuous strand, comminuting the strand into granules and shaping the granules into any desired shape.

Preferred Embodiments

Example I

Compositions of 65 parts by weight of poly (2,6-dimethyl-1,4-phenylene) -10 ether (IV 0.47 parts / g in CHCl 3 at 30 ° C), 35 parts by weight of a styrene-bromostyrene copolymer with 27% bromine, 10 parts by weight hydrogenated styrene-butadiene-styrene block copolymer (Kraton G 1652), 3 parts by weight titanium dioxide, 1.0 parts by weight diphenyldecyl phosphite, 0.15 parts by weight zinc sulfide, 0.15 parts by weight. parts of zinc oxide and 1.5 parts of polyethylene were extruded and formed into ASTM-15 standard test pieces. For comparison, a blend of the same composition but with homopolystyrene (Dylene 8G) instead of the bromostyrene copolymer was extruded and formed in the same manner. The properties of the mixtures are listed in Table A. The mixture containing the bromostyrene copolymer had about the same gloss, tensile strength and impact strength as the mixture with the styrene homopolymer, but a significantly higher deformation temperature and much better burning properties.

TABLE A

Blend with Blend with polystyrene bromostyrene homopolymer copolymer

Elongation (%) 29 33

Strain limit (kPa) 53800 56500

Tensile strength (kPa) 51700 55200 30 Izod impact strength (Joule / cm notch) 2.72. 2.51

Gardner impact strength (Joule) 25.4 24.3

Gloss (45 °). 62.0 61.3

Yellowness index 23.2 18.7

Distortion temperature (° G) 137 140.5 35 DL-94 Rating Does not meet V-l (dripping burning particles)

Average burn time (seconds) 53 5.1 81 02 6 33 - 5 -

Examples II-IV

Compositions of 85 parts by weight. poly (2,6-dimethyl-1,4-phenylene) ether with an intrinsic viscosity of 0.54 dl / g (in CHCl 3 at 30 ° C), 15 parts by weight. of the styrene-bromostyrene copolymer described in Example I, 5 parts by weight of hydrogenated block copolymer (Kraton G 1652), 3 parts by weight.

Titanium dioxide, 1 part by weight. diphenyldecyl phosphite, 0.15 parts by weight. zinc sulfide, 0.15 parts by weight. zinc oxide and 1.5 parts by weight. polyethylene was extruded and formed as described in Example I. For comparison, a mixture of the same composition but with polystyrene homopolymer (Dylene 8G) 1. p.v. the bromostyrene copolymer extruded and formed in the same manner.

Mixtures of the same composition, but with 3 parts by weight. triphenyl phosphate were added, prepared in the same manner using the same poly (2,6-dimethyl-1,4-phenylene) ether; in one mixture, a low molecular weight poly (2,6-dimethyl-1,4-phenylene) ether was used (IV - 0.37 dl / g in CHCl 2 at 30 ° C). The properties of these mixtures are given in Table B. Blends containing the styrene-bromo-styrene copolymer had about the same tensile strength, impact strength, gloss and color as blends of the same composition prepared with polystyrene homopolymer, but a higher deformation temperature and much better burning properties. The bromo-styrene copolymer compositions having a ratio in the copolymer of 85:15 had good fire resistance (rating V-1 according to UL-94) with no added flame retardant; however, this resistance was further improved (rating V-0) by adding 3 parts by weight. triphenyl phosphate.

The molecular weight of the poly (2,6-dimethyl-1,4-phenylene) ether used in the bromostyrene copolymer blends can be varied over a wide range without a significant effect on flammability and most other properties, but Izod impact strength was lowered and Gardner impact strength greatly increased by a decrease in the intrinsic viscosity of the poly (2,6-dimethyl-1,4-phenylene) ether from 0.54 to 0.37 dl / g, determined in CHCl 3 at 30 ° C.

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Examples V-VII

A mixture of 75 parts by weight. poly (2,6-dimethyl-1,4-phenylene) ether, 25 parts by weight. bromostyrene-styrene copolymer, 10 parts by weight. hydrogenated styrene-butadiene copolymer (Kraton G 1652), 3 parts. titanium dioxide, 1 part by weight. diphenyldecyl phosphite, 0.15 parts by weight. zinc sulfide, 0.15 part by weight. zinc-5 oxide and 1.5 parts by weight. polyethylene was extruded and formed as described in Example I. Another mixture of the same composition containing 3 parts by weight was also prepared. triphenylphosphate were added, and for comparison blends of the same composition, wherein the bromostyrene copolymer was replaced by polystyrene homopolymer (Dylene 8G).

Other mixtures as described above were prepared using polystyrene (Dylene 8G) and enough decabromodiphenyl ether to convert the percentage of bromine (based on the poly (2,6-dimethyl-1,4-phenylene) ether and the polystyrene only) equal to the bromine percentage in the blends with the bromostyrene copolymer; other blends were prepared with a slightly larger amount of decabromodiphenyl ether, so that the percentage of bromine, based on the total weight of the blend, was equal to that of the blends with the bromostyrene copolymer. The properties of the mixtures are given in Table C. The blends containing the bromostyrene copolymer had a high deformation temperature and a high Izod impact strength. Most of the properties are approximately equivalent to those of the control mixtures prepared with polystyrene homopolymer, but the deformation temperature was slightly higher and the burning properties were greatly improved. The mixture prepared with the bromostyrene copolymer had the flammability rating V-1 without any added flame retardant; when adding only 3 wt. parts. Triphenyl phosphate was rated V-Q, with a very short burn time.

The same amount of bromine added in the form of decabromodiphenyl ether caused an increase in color, a decrease in the deformation temperature and a lower Izod impact strength, and was much less effective as a flame suppressant.

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8102633 - 9 -

Example VIII

The mixtures described in Examples V-VII were formed into plates of about 0.32 cm by about 6.35 cm by about 8.25 cm. The plates were racked under ordinary one-thickness window glass on a rotating platform? the plates were exposed at a distance of about 7.6 cm with a battery of fluorescent UV lamps. The yellowness index was determined at 24 hour intervals according to the ASTM test method D1925; the results are given in Table B. The compositions containing the low molecular weight bromine additives quickly yellowed (blends J-M), while compositions P and G, containing the bromostyrene copolymer, yellowed slightly less than the blends H and I, which did not contain bromine.

Table D

Composition1 ^ · Increase in yellowness index_ __ 24 hours 48 hours 72 hours 15 F -0.5 1.2 2.8 G -0.5 1.7 2.8 H2) 0.0 2.1 3.7 I2 ) 0.1 2.1 3.6 J2) 14.2 32.1 37.8 20 K2) 15.0 28.6 39.2 L2 13.0 29.7 36.7 M2 13.7 29 , 4 37.7 1)

Compositions of Table C 25 2 ^ Control

example IX

A mixture of 75 parts by weight. poly (2,6-dimethyl-1,4-phenylene) ether, 25 parts by weight. of the bromostyrene copolymer, 10 parts by weight. hydrogenated styrene-butadiene-styrene block copolymer (Kraton G 1651), 3 wt.

30 parts. titanium dioxide, 3 parts by weight. triphenyl phosphate, 1 part by weight. diphenyldecylphosphine, 0.15 parts by weight. zinc sulfide, 0.15 part by weight. zinc oxide and 1.5 parts by weight. polyethylene was extruded and formed as described in Example I. Properties of the composition are given below:

Elongation (%) 29 35 Elongation limit (kPa) 74,500

Tensile strength (kPa) 60,000

Izod impact strength (Joule / cm) 0.96 8102633 - 10-

Gar dner-s lay resistance (Joule 27.1

Gloss (45 °) 38.9

Yellowness index 24.3

Distortion temperature (° C) 150.5 5 UL-94 rating V-0

Average burn time (seconds) 3.1

Example X.

Compositions of 75 parts by weight were prepared. poly (2,6-dimethyl-1,4-phenylene) ether, 24 parts. of a bromostyrene polymer or bromostyrene-styrene copolymer, 3 parts. titanium dioxide, 1.5 parts by weight. triphenyl phosphate and 10 parts by weight. of a styrene-butadiene-styrene block copolymer (Kraton G 1651) by extrusion, after which the compositions were formed. The compositions had the properties given in Table E:

Table E

15% Bromostyrene Izod impact- Gardner- Average Appearance in polymer strength impact-resistant burning time. ..... ness' UL-94 · .........

70 3.26 31.1 1.9 good 85 4.59 33.9 1.7 good 1) 100 4.27 1.69 0.9 laminated 1) 20 Control example xi

Compositions of 60 parts by weight were prepared. poly (2,6-dimethyl-1,4-phenylene) ether resin, 40 parts by weight. of a bromostyrene polymer or a copolymer of bromostyrene and styrene, 1.5 parts. triphenylphosphate and 10 parts by weight. of a styrene-butadiene-styrene block copolymer by extrusion, after which the compositions were formed. The compositions had the properties listed in Table F.

Table F

% Bromostyrene Izod impact- Gardner- Average Appearance in polymer stiffness impact-resistance burning time 30 _ · UL-94 70 2.99 25.4 2.9 good 85 2.19 3.39 2.0 laminated 1) 100 2 , 13 0.56 0.6 laminated 1 81 0 2 6 33

Control - 11 -

Comparative Example 1,000 g of bromostyrene monomer (Makhteshim-27% ortho, 70% para and 3% meta) was stirred under nitrogen at 82 ° C with 0.6 g azo-bis-isobutyro-nitrile and 0.6 g dicumyl peroxide. After 6 hours, the product was suspended in 1500 ml of water containing 6 g of polyvinyl alcohol and 4.5 g of gelatin; the polymerization was continued at 85 ° -100 ° C for 14 hours. Mixtures with poly (2,6-dimethyl-1,4-phenylene) ether were prepared by coprecipitation from toluene in methanol and the mixtures were pressed into films to determine the transition temperature to the glass condition.

% poly (2,6-dimethyl- Tg (l) Tg (2) i0 1,4-phenylene) ether (° C) (° C) 0 131 25 136 208 50 137 206 75 137 209 15 100 --- 211

The blends exhibit 2 glass transition temperatures, which is indicative of the lack of compatibility of these two materials.

81 02 6 33

Claims (10)

Flame retardant thermoplastic molding material, characterized by: (a) a polyphenylene ether resin; and (b) a copolymer of styrene and bromostyrene. Material according to claim 1, characterized in that the polyphenyl-5-ether ether resin is a compound according to formula (1) of the formula sheet, wherein 0 is a hydrogen atom, hydrocarbon group, halohydrocarbon group with at least two carbon atoms between the halogen atom and the phenyl core, hydrocarbon oxy group or halohydrocarbonoxy group having at least two carbon atoms between the halogen atom and the phenyl core 10, each of the symbols Q 'and O "have the same meanings as given above for Q and further represent halogen stalls, provided that both Q and Q' are not tertiary carbon atoms and n is a number with a value of at least 50. 3. Material according to claim 2, characterized in that Q "is hydrogen 15. Material according to claim 2, characterized in that the polyphenylene ether resin is poly (2,6-dimethyl-1,4-phenylene) ether resin. Material according to claims 1-4, characterized in that the weight ratio between styrene and bromostyrene in the copolymer is 85: 15-20: 85. 6. Material according to claims 1-5, characterized by 20-90 parts by weight. polyphenylene ether and 80-10 parts by weight. copolymer. Material according to claims 1-6, characterized by a filler. 8. Material according to claims 1-7, characterized by a flame-retardant phosphate. Material according to claims 1-8, characterized by a thermoplastic rubber. Material according to claim 9, characterized in that the thermoplastic rubber is an A-B-A block copolymer. 8102635 ---- * s 2348-1130 - Appendix 4 General Electric Company q "q": Q "- Q i. | (2) Q0-P - * - 0Q I CQ j 8102633