JP2000072958A - Flame-retardant resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a non-halogen, flame-retardant resin composition which has a high fire retardancy, yields a high workability and safety by improving the safety when heating red phosphorus and allows no increase in phosphoric acid production which affects electrical properties. SOLUTION: The tilted composition comprises 100 pts.wt. thermoplastic aromatic polyester resin such as polyetetramethylene terephthalate or the like, from 3 to 70 pts.wt. novolak phenol resin, from 1 to 15 pts.wt. coated red phosphorus powder which has a cured resin coating and comprises a globular red phosphorus having no crushed surface, which is directly obtained through a conversion treatment of white phosphorus requiring no grinding and from 0.05 to 5 pts.wt. at least one of titanium oxide, aluminum oxide and molybdenum sulfide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a flame-retardant resin composition having a high flame retardancy. More specifically, the present invention relates to a non-halogen flame-retardant resin composition which enhances the stability of red phosphorus, is excellent in workability and safety, and has no increase in phosphoric acid generation which affects electric properties.

[0002]

2. Description of the Related Art Polyester resins such as polybutylene terephthalate have excellent mechanical properties, heat resistance, chemical resistance, etc., and are widely used as molded articles in applications such as electric / electronic fields and automobile fields. I have.

[0003] Among these, there are many uses requiring flame retardancy, and mainly halogen compounds and antimony compounds are used as flame retardants,
A resin having flame retardancy imparted by using as a flame retardant aid is provided.

[0004] However, halogen-based flame retardants may cause decomposition products to corrode metals as electric products, and some halogen-based flame retardants have non-halogen-based flame retardants because of their environmental impact. Fuel resins are needed.

[0005] Phosphorus compounds are non-halogen flame retardants, and low molecular phosphate esters such as triphenyl phosphate (TPP) have been frequently used as typical organic phosphorus compounds. However, a polyester resin such as polybutylene terephthalate has a relatively high processing temperature, and has a problem of bleed out and heat resistance in the case of a low molecular weight phosphate ester.

JP-A-7-126498 discloses a polyester resin, an epoxy compound having two or more epoxy groups in a molecule, a phenol resin and / or phosphorus, nitrogen having a functional group capable of reacting with an epoxy group.
A non-halogen flame retardant for polyester resin is disclosed which is obtained by melting and reacting at least one non-halogen flame retardant compound selected from boron compounds.

JP-A-7-278267 discloses a flame-retardant polyester resin composition in which 5 to 50 parts by weight of the non-halogen flame retardant is mixed with 100 parts by weight of a polyester resin.

[0008] The non-halogen flame retardant is characterized in that an epoxy compound having two or more epoxy groups in a molecule is used.

JP-A-8-188717 discloses thermoplastic resins such as polystyrene and polyester, phosphorus compounds such as phosphates and phosphites, phenolic resins (eg cresol) and aralkyl halides (eg α, α-). A flame-retardant resin composition comprising a phenol aralkyl resin such as a reaction product of dichloro-p-xylene) is disclosed.

Japanese Patent Application Laid-Open No. Hei 8-208888 discloses a thermoplastic resin such as polystyrene or polyester, a phosphorus compound such as a phosphoric acid ester or a phosphite, and a phenolic resin from a phenol substituted at the ortho or para position. A flame retardant resin composition is disclosed.

On the other hand, the following compounds are known as those using red phosphorus which exhibits excellent flame retardancy even when added in a small amount among phosphorus compounds.

[0012] Journal of Fire retardant chemistry (Journalof Fire R)
etardant Chemistry) vol. 7,
69-76, 1980 discloses that polystyrene is flame retarded by red phosphorus and a phenolic resin.

[0013] Also, Plastics Engineering Nov.
Ember, 29-31, 1993 discloses that PBT is flame retarded by red phosphorus and a phenolic resin.

Japanese Patent Publication No. 2-37370 discloses 99-34 parts by weight of a thermoplastic polyester resin having a softening point of 150 ° C. or more, such as polyethylene terephthalate.
A flame-retardant polyester resin composition comprising 1 to 25 parts by weight of red phosphorus and 10 to 55 parts by weight of a reinforcing filler coated with a thermosetting resin is disclosed.

[0015]

SUMMARY OF THE INVENTION An object of the present invention is to provide a non-halogen flame retardant which has a high flame retardant effect, is excellent in workability and safety, and suppresses the generation of phosphoric acid which affects electric characteristics. To provide a conductive resin composition,
An object of the present invention is to provide a flame-retardant resin composition for electric / electronic parts.

[0016]

That is, the present invention comprises (A) 100 parts by weight of a thermoplastic aromatic polyester resin, (B) 3 to 70 parts by weight of a novolak type phenol resin, and (C) a coating of a cured resin. And from 1 to 15 parts by weight of a coated red phosphorus powder composed of spherical red phosphorus having no crushed surface and directly obtained by a yellow phosphorus conversion treatment method that does not require grinding, and (D) a group consisting of titanium oxide, aluminum oxide and molybdenum sulfide. It is a flame-retardant resin composition comprising 0.05 to 5 parts by weight of at least one selected compound.

In the flame-retardant resin composition of the present invention, the amount of phosphine generated after heating at 120 ° C. for 24 hours is 5 × 10 ⁻⁵ g or less per 1 g of red phosphorus contained in the flame-retardant resin composition, and 1 to 10 g.
The point at which the amount of phosphoric acid generated under the conditions of 21 ° C., 100% RH, 2.1 atm and 200 hours of moist heat is 3 × 10 ⁻⁴ g or less per 1 g of red phosphorus contained in the flame-retardant resin composition. With remarkable features.

The present invention also provides a flame-retardant resin composition for electric / electronic parts, comprising the above-mentioned flame-retardant resin composition and having the above-mentioned properties.

Hereinafter, the present invention will be described in detail. In the present invention, the thermoplastic aromatic polyester resin (A) is a polyester containing an aromatic dicarboxylic acid as a main dicarboxylic acid component and an aliphatic diol having 2 to 10 carbon atoms as a main glycol component. Preferably, at least 80 mol%, more preferably at least 90 mol%, of the dicarboxylic acid component comprises the aromatic dicarboxylic acid component. The glycol component preferably comprises at least 80 mol%, more preferably at least 90 mol%, of the glycol component of an aliphatic diol component having 2 to 10 carbon atoms.

Preferred examples of the aromatic dicarboxylic acid include terephthalic acid, isophthalic acid, phthalic acid, methyl terephthalic acid, methyl isophthalic acid, and 2,6-naphthalene dicarboxylic acid. These can be used alone or in combination of two or more. Examples of the secondary dicarboxylic acid other than the aromatic dicarboxylic acid include aliphatic or alicyclic dicarboxylic acids such as adipic acid, sebacic acid, decanedicarboxylic acid, azelaic acid, dodecanedicarboxylic acid, and cyclohexanedicarboxylic acid.

Examples of the aliphatic diols having 2 to 10 carbon atoms include aliphatic diols such as ethylene glycol, trimethylene glycol, tetramethylene glycol, hexamethylene glycol, neopentyl glycol and the like, and fatty acids such as 1,4-cyclohexanedimethanol. A cyclic diol can be mentioned. One or more of these aliphatic diols and alicyclic diols can be used together. Examples of the secondary glycol other than the aliphatic diol having 2 to 10 carbon atoms include p, p'-dihydroxyethoxybisphenol A and polyoxyethylene glycol.

As the thermoplastic aromatic polyester resin (A), the main dicarboxylic acid component is at least one dicarboxylic acid selected from the group consisting of terephthalic acid and 2,6-naphthalenedicarboxylic acid, and the main diol is Polyesters comprising an ester unit whose component is at least one diol selected from the group consisting of ethylene glycol, triethylene glycol and tetramethylene glycol are preferred.

Of these, polyesters having ethylene terephthalate, trimethylene terephthalate, tetramethylene terephthalate or tetramethylene-2,6-naphthalenedicarboxylate as a main repeating unit are preferred. Further, a polyester elastomer having these repeating units as main repeating units of a hard segment can also be used.

As a soft segment of a polyester elastomer containing tetramethylene terephthalate or tetramethylene-2,6-naphthalenedicarboxylate as a main repeating unit of a hard segment, for example, a dicarboxylic acid is formed from terephthalic acid, isophthalic acid, sebacic acid and adipic acid. Consisting of one or more dicarboxylic acids selected from the group consisting of
10 long-chain diol and H (OCH ₂ CH ₂ ) _i OH
(I = 2 to 5) It is possible to use one composed of one or more diols selected from the group consisting of polyester having a melting point of 100 ° C. or lower or amorphous, or composed of polycaprolactone.

The main component is a component of 80 mol% or more, preferably 90 mol% or more of the total dicarboxylic acid component or the total glycol component, and the main repeating unit is 80 mol% or more of the total repeating unit, preferably Is 90
It is a repeating unit of at least mol%.

The thermoplastic aromatic polyester resin used in the present invention has an intrinsic viscosity of preferably 0.5 to 1.4 dl / g, more preferably 0.6 to 1.2 dl / g, measured in orthochlorophenol at 35 ° C. It is. When the intrinsic viscosity is less than 0.5, the mechanical strength of the obtained composition is low, and thus it is not preferable. When the intrinsic viscosity is more than 1.4, the fluidity of the obtained composition is unfavorably reduced.

The novolak type phenol resin (B) used in the present invention is obtained by polycondensing phenol and formaldehyde in the presence of an acid catalyst. The weight average molecular weight is preferably from 600 to 13,000,
7,000 is more preferred.

The addition amount of the novolak type phenol resin is 3 to 70 parts by weight based on 100 parts by weight of the thermoplastic aromatic polyester resin (A). If the addition amount is less than 3 parts by weight, the flame retardancy is not sufficient, and if it exceeds 70 parts by weight, the mechanical properties of the molded article are lowered. The preferred amount is 5 to 50 parts by weight.

In the present invention, the coated red phosphorus powder (C) comprising spherical red phosphorus without a crushed surface, which has a cured resin coating and is directly obtained by a yellow phosphorus conversion treatment method which does not require grinding, is a cured resin coating. Used as a coated red phosphorus powder.

Originally, there is a danger that red phosphorus alone may ignite or generate phosphine due to high temperature or mechanical shock.

Red phosphorus is usually produced by heat-treating yellow phosphorus for several days in a reaction vessel called a conversion kettle. In this method, red phosphorus is obtained as a lump and an additive of a resin composition as a flame retardant is used. When used as, a pulverizing step is required. The red phosphorus thus obtained forms many active sites on the particle surface by pulverization, and reacts with oxygen and water molecules to cause ignition, and also to generate phosphine and oxidation products.

In the present invention, instead of the conventional red phosphorus obtained through such a pulverizing step, sphere-like red phosphorus having no crushed surface and directly obtained by a yellow phosphorus conversion treatment method is used. By using such spherical red phosphorus, the surface is extremely stabilized, the stability of red phosphorus is increased, and the stability of the composition is improved.

The method for producing sphere-like red phosphorus used in the present invention includes the following method. That is, in a closed vessel replaced with an inert gas, yellow phosphorus is heated to a temperature near the boiling point to start the conversion reaction of red phosphorus, and the reaction is stopped when the conversion or the particle size of red phosphorus reaches a desired level. Then, amorphous red phosphorus composed of microsphere-like particles or aggregates thereof that does not require any pulverization can be obtained by distilling unconverted yellow phosphorus. The conversion and the particle size of red phosphorus are controlled by the reaction time and the reaction temperature.
Particularly preferred is 50 ° C. and a conversion of 60% or less.

The cured resin of the coating of the coated red phosphorus powder is preferably a cured resin of at least one curable resin selected from the group consisting of phenolic resins, epoxy resins, unsaturated polyester resins, melamine resins, urea resins and aniline resins. Things.

The coated red phosphorus powder may further contain at least one inorganic compound selected from the group consisting of aluminum hydroxide, magnesium hydroxide, zinc hydroxide and hydroxide of titanium in the cured resin of the coating. Preferably
These inorganic compounds may be further contained in contact with red phosphorus under the cured resin film. The average particle size of the red phosphorus powder is preferably in the range of 5 to 40 μm, more preferably in the range of 25 to 35 μm.

The coated red phosphorus powder (C) comprising a spherical red phosphorus having no crushed surface and having a coating of a cured resin and directly obtained by a yellow phosphorus conversion treatment method which does not require pulverization is a thermoplastic aromatic polyester resin (C). A) 1 to 100 parts by weight
It is blended so as to be in a range of 15 parts by weight. If the amount is less than 1 part by weight, the flame retardancy is insufficient. If the amount is more than 15 parts by weight, the mechanical properties of a molded article obtained from the flame retardant resin composition deteriorate, which is not preferable.

Although the coated red phosphorus powder is remarkably improved in handling and safety as compared with red phosphorus alone, in the present invention, when using the coated red phosphorus powder, a thermoplastic resin is used for further safety. It is desirable to use as a master pellet that has been melt-kneaded in advance. By using the master pellet, a resin composition having excellent mechanical strength of a molded article obtained when the molded article is formed can be obtained.

In this case, as the thermoplastic resin used for melt-kneading, polyethylene, polypropylene, EPDM, ethylene ethyl acrylate, ethylene methyl acrylate, thermoplastic polyester, polyamide, aromatic polycarbonate and the like can be mentioned. Usually, polypropylene, polyester resin or aromatic polycarbonate is desirable.

Coated red phosphorus powder in master pellet (C)
The content varies depending on the type of the thermoplastic resin used, but is usually preferably 10 to 50% by weight. If the amount is less than 10% by weight, the amount of the added master pellets is relatively increased. If the amount is more than 50% by weight, it is difficult to form the master pellets, and there is a risk that the safety is reduced.

In the present invention, at least one compound (D) selected from the group consisting of titanium oxide, aluminum oxide and molybdenum sulfide is blended in the resin composition. By blending this component (D), sphere-like red phosphorus is remarkably stabilized in the thermoplastic aromatic polyester resin, and the generation amount of phosphine can be greatly reduced. Such effects of stabilizing sphere-like red phosphorus and reducing the amount of generated phosphine can be achieved by blending titanium oxide, aluminum oxide, molybdenum sulfide or copper oxide. In this case, the electrical properties are impaired because the phosphorous reacts with sphere-like red phosphorus to generate phosphoric acid.

The component (D) used in the present invention is preferably added in an amount of 0.05 to 5 parts by weight of at least one of titanium oxide, aluminum oxide and molybdenum sulfide. If the amount is less than 0.05 part by weight, the stabilizing effect of the sphere-like red phosphorus is small, and if it is more than 5 parts by weight, the mechanical properties of a molded article obtained from the flame-retardant resin composition are undesirably reduced.

The component (D) used in the present invention is (A),
When used in combination with the components (B) and (C), 120
The amount of phosphine generated after heating at 24 ° C. for 24 hours is 5 × 10 ⁻⁵ g or less per 1 g of red phosphorus contained in the flame-retardant resin composition, and the conditions are 121 ° C., 100% RH and 2.1 atm. It is possible to obtain a flame-retardant resin composition in which the amount of phosphoric acid produced below is reduced to 3 × 10 ⁻⁴ g or less per 1 g of red phosphorus contained in the flame-retardant resin composition. Since the stability of the sphere-like red phosphorus is increased and the generation of phosphoric acid is not increased, the influence on the electrical properties is extremely small.

The flame-retardant resin composition of the present invention may further contain an inorganic filler as long as the object of the present invention is not impaired. Such fillers include, for example, calcium carbonate,
Titanium oxide, feldspar-based mineral, clay, white carbon,
Granular or amorphous fillers such as carbon black, glass beads, silica, etc .; scaly fillers such as kaolin clay and talc; glass fibers, urastonite, potassium titanate, aluminum borate, carbon fibers, aramid fibers And fibrous fillers such as
When the inorganic filler is contained, it is preferably contained in the range of 5 to 150 parts by weight based on 100 parts by weight of the thermoplastic aromatic polyester resin (A).

Further, generally used additives such as antioxidants, heat stabilizers, ultraviolet absorbers, lubricants, nucleating agents, plasticizers, release agents, pigments, impact modifiers such as various elastomers, and polytetrafluorocarbon A flame retardant modifier such as ethylene may be further added.

As a stabilizer for red phosphorus, oxides or hydroxides of zinc, aluminum, magnesium and titanium can be further added.

The flame-retardant resin composition of the present invention is prepared by simultaneously extruding each component such as polyester resin, sphere-like red phosphorus powder or sphere-like red phosphorus master pellet and novolak type phenol resin, and, if necessary, glass fiber using an extruder. It can be manufactured by a method of melt-kneading. At this time, any of the components may be melt-kneaded in advance.

The resin composition obtained by melt-kneading with an extruder is cut into pellets by a pelletizer and then molded, but the molding method may be any molding method such as injection molding or blow molding.

The flame-retardant resin composition of the present invention can be used for home appliances, OA
It is suitably used in molded parts for electronic and electrical applications such as equipment and in automotive applications. Specifically, it can be used for a switch component, a motor component, an ignition coil case, a coil bobbin, a connector, a relay case, a fuse case, and the like.

[0049]

The present invention will be described in more detail with reference to the following examples.
The intrinsic viscosity was measured at 35 ° C. using an orthochlorophenol solvent. Each test was evaluated according to the following method.

Flame retardancy: The flame retardancy was evaluated by a UL94 standard vertical burning test method using a 0.8 mm thick test piece. Flame retardancy is measured according to the evaluation method described in UL94.
O, V-1, V-2, and HB were classified into four types.

Generated amount of phosphine: 10 g of the pellet prepared by the above method was placed in a 500 ml stoppered glass bottle, and heated at 120 ° C. for 24 hours with the lid closed. After air cooling at room temperature for 5 hours, the phosphine concentration in the glass bottle was measured, and the amount of phosphine generated per gram of red phosphorus was calculated by dividing by the amount of red phosphorus contained in the pellet. The phosphine concentration was measured using a gas detector tube for phosphine manufactured by Gastech.

Generated amount of phosphoric acid: 25 mm × 25 mm using an injection molding machine (manufactured by FANUC) having a mold clamping force of 15 ton.
A flat plate having a thickness of 1 mm x 1 mm was prepared, and
The wet heat treatment was performed at 200 ° C., 100% RH and 2.1 atm for 200 hours. After cooling at room temperature for 24 hours, 5m
1 l of pure water to elute the precipitates on the surface of the molded product, and measure the concentrations of phosphoric acid and phosphorous acid using an ion chromatograph (DX-100, manufactured by Dionex Co., Ltd.). It was calculated as the amount of phosphoric acid generated per gram of red phosphorus by dividing by the amount of red phosphorus contained.

Examples 1 to 5 and Comparative Examples 1 to 8 The compositions of Examples 1 to 5 are shown in Table 1, and the compositions of Comparative Examples 1 to 8 are shown in Table 2.
Shown in Both extruders are twin screw extruders TEX44
The cylinder temperature was 250 ° C. for Examples 1-4 and Comparative Examples 1-7, 280 ° C. for Example 5 and Comparative Example 8, and the discharge rate was any. Is 50Kg / hr and the screw rotation speed is 150r.p.
The mixture was melt-kneaded at m and pelletized by a cutter. The extrudability in the examples was stable with almost no thread breakage. 13 obtained chips
After drying at 0 ° C. for 5 hours, Examples 1-4 and Comparative Examples 1-7 have a melting temperature of 260 ° C. and a mold temperature of 60 ° C., and Examples 5 and Comparative Example 8 have a melting temperature of 280 ° C. and a mold temperature of 60 ° C. Were set, and a combustion test piece and a flat plate test piece were prepared.

[0054]

[Table 1]

[0055]

[Table 2]

Tables 3 and 4 show the results of the combustion test, the amount of phosphine generated, and the amount of phosphoric acid evaluated using these pellets and test pieces.

[0057]

[Table 3]

[0058]

[Table 4]

A coated red phosphorus powder consisting of spherical red phosphorus having no crushed surface and having a cured resin coating and having no crushed surface directly obtained by a yellow phosphorus conversion treatment method not requiring pulverization is available from Rin Kagaku Kogyo Co., Ltd. Nova Excel 140 was used.

As is clear from Tables 3 and 4, a coated red phosphorus powder having a spheroidal red phosphorus without a crushed surface, which has a cured resin coating and is directly obtained by a yellow phosphorus conversion treatment method which does not require grinding, is used. According to the present invention, the amount of phosphine generated can be reduced, and the amount of phosphine generated can be further reduced while suppressing the generation of phosphoric acid by using titanium oxide or aluminum oxide. 0.8m
High flame retardancy of V-0 was achieved with a thickness of m.

[0061]

The flame-retardant resin composition of the present invention is a non-halogen flame-retardant resin composition, which has a high flame retardancy and which is used when heating red phosphorus used as a flame retardant. In order to enhance the stability, use a coated red phosphorus powder consisting of spherical red phosphorus without a crushed surface directly obtained by a yellow phosphorus conversion method that has a cured resin coating and does not require grinding, and further includes titanium oxide,
When at least one of aluminum oxide and molybdenum sulfide is used in combination, the amount of phosphine generated can be further reduced, and the effect of ensuring excellent workability and safety can be obtained. In addition, since titanium oxide, aluminum oxide, and molybdenum sulfide do not increase phosphoric acid production, they have a feature that the possibility of adversely affecting electrical characteristics is extremely small.

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Claims (10)

[Claims] (A) 100 parts by weight of a thermoplastic aromatic polyester resin, (B) novolak type phenolic resin
70 parts by weight, 1 to 15 parts by weight of a coated red phosphorus powder comprising spherical red phosphorus without a crushed surface, which is obtained by a conversion treatment method of yellow phosphorus which has a coating of (C) a cured resin and does not require grinding. D) A flame-retardant resin composition comprising 0.05 to 5 parts by weight of at least one compound selected from the group consisting of titanium oxide, aluminum oxide and molybdenum sulfide. 2. The amount of phosphine generated after heating at 120 ° C. for 24 hours is 5 × 10 ⁻⁵ g or less per 1 g of red phosphorus contained in the flame retardant resin composition, and 121 ° C., 100% RH.
The amount of phosphoric acid generated under the condition of 1 atmosphere and 200 hours of moist heat was 3 × 10 3 g / g of red phosphorus contained in the flame-retardant resin composition.
The flame-retardant resin composition according to claim 1, wherein the composition is not more than ^-4 g. 3. A thermoplastic aromatic polyester resin (A)
Is a polyester having ethylene terephthalate, trimethylene terephthalate, tetramethylene terephthalate or tetramethylene-2,6-naphthalenedicarboxylate as a main repeating unit. 4. The flame-retardant resin composition according to claim 1, wherein the weight-average molecular weight of the novolak-type phenolic resin (B) is in the range of 600 to 13,000. 5. A cured resin of a coating of a coated red phosphorus powder (C) comprising a spherical red phosphorus having no crushed surface and having a coating of a cured resin and obtained directly by a conversion treatment method of yellow phosphorus which does not require grinding. The flame-retardant resin composition according to claim 1, comprising a cured product of at least one curable resin selected from the group consisting of a phenol resin, an epoxy resin, an unsaturated polyester resin, a melamine resin, a urea resin, and an aniline resin. 6. A coating of a coated red phosphorus powder (C) comprising a sphere-like red phosphorus having no crushed surface and having a coating of a cured resin and directly obtained by a conversion treatment method of yellow phosphorus which does not require pulverization. 2. The flame-retardant resin composition according to claim 1, wherein at least one inorganic compound selected from the group consisting of aluminum hydroxide, magnesium hydroxide, zinc hydroxide and titanium hydroxide is dispersedly contained. . 7. A coating of a coated red phosphorus powder (C) comprising a sphere-like red phosphorus having no crushed surface and having a coating of a cured resin and obtained directly by a yellow phosphorus conversion treatment method that does not require grinding. Below, a coating comprising at least one inorganic compound selected from the group consisting of aluminum hydroxide, magnesium hydroxide, zinc hydroxide and a hydroxide of titanium,
The flame-retardant resin composition according to claim 6, which is further present in contact with red phosphorus. 8. A coated red phosphorus powder (C) comprising a spherical red phosphorus having no crushed surface and having a coating of a cured resin and directly obtained by a method for converting yellow phosphorus which does not require pulverization, having an average particle size of 5%. The flame-retardant resin composition according to claim 1, which is in a range of from 40 m to 40 m. 9. A thermoplastic aromatic polyester resin (A)
The flame-retardant resin composition according to claim 1, further comprising 5 to 150 parts by weight of an inorganic filler based on 100 parts by weight. 10. A flame-retardant resin composition for electric / electronic parts, comprising the flame-retardant resin composition according to claim 2.