JP2001002945A5 - - Google Patents
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- JP2001002945A5 JP2001002945A5 JP1999176719A JP17671999A JP2001002945A5 JP 2001002945 A5 JP2001002945 A5 JP 2001002945A5 JP 1999176719 A JP1999176719 A JP 1999176719A JP 17671999 A JP17671999 A JP 17671999A JP 2001002945 A5 JP2001002945 A5 JP 2001002945A5
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- Prior art keywords
- flame
- retardant resin
- resin composition
- composition according
- organic phosphorus
- Prior art date
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- 150000002903 organophosphorus compounds Chemical class 0.000 description 22
- 239000003063 flame retardant Substances 0.000 description 18
- 239000011342 resin composition Substances 0.000 description 15
- 229920001971 elastomer Polymers 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 229920005992 thermoplastic resin Polymers 0.000 description 5
- 230000005494 condensation Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001955 polyphenylene ether Polymers 0.000 description 4
- 229920000122 Acrylonitrile butadiene styrene Polymers 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N Acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229920000578 graft polymer Polymers 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- -1 polytetrafluoroethylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Xylenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N Diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 210000001624 Hip Anatomy 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- XSXWYGABGYBZRM-UHFFFAOYSA-N carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound OC(O)=O.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 XSXWYGABGYBZRM-UHFFFAOYSA-N 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
Description
【請求項７】 （β）有機リン化合物が、式（１）で表される１種または２種以上のオリゴマー系有機リン化合物である請求項１〜６のいずれかに記載の難燃性樹脂組成物。
【化１】
Embedded image
【請求項８】 （β）有機リン化合物が、式（２）で表される１種または２種以上のオリゴマー系有機リン化合物である請求項１〜６のいずれかに記載の難燃性樹脂組成物。
【化２】
Embedded image
【請求項９】 （β）有機リン化合物が、式（１）で表される１種または２種以上のオリゴマー系有機リン化合物であり、その平均縮合度Ｎが１以上１．２未満である請求項１〜６のいずれかに記載の難燃性樹脂組成物。 9. The organic phosphorus compound (β) is one or more oligomeric organic phosphorus compounds represented by the formula (1), and the average degree of condensation N is 1 or more and less than 1.2. The flame-retardant resin composition according to claim 1.
【請求項１０】 （β）有機リン化合物が、式（２）で表される１種または２種以上のオリゴマー系有機リン化合物であり、その平均縮合度Ｎが１以上１．２未満である請求項１〜６のいずれかに記載の難燃性樹脂組成物。 10. The organic phosphorus compound (β) is one or more oligomeric organic phosphorus compounds represented by the formula (2), and has an average degree of condensation N of 1 or more and less than 1.2. The flame-retardant resin composition according to claim 1.
【請求項１１】 （β）有機リン化合物の酸価が３ｍｇＫＯＨ／ｇ以下である請求項１〜１０のいずれかに記載の難燃性樹脂組成物。 11. The flame-retardant resin composition according to claim 1, wherein the acid value of (β) the organic phosphorus compound is 3 mgKOH / g or less.
【請求項１２】 さらにポリテトラフルオロエチレンを含む請求項１〜１１のいずれかに記載の難燃性樹脂組成物。 12. The flame-retardant resin composition according to claim 1 , further comprising polytetrafluoroethylene.
すなわち本発明は、
［１］（α）熱可塑性樹脂１００重量部、（β）有機リン化合物１〜３０重量部、及び（γ）脂環式エポキシ系安定剤０．０１〜５重量部が含まれる難燃性樹脂組成物、
［２］（α）熱可塑性樹脂が、ポリカーボネート系樹脂、または、ポリフェニレンエーテル系樹脂である［１］記載の難燃性樹脂組成物、
［３］（α）熱可塑性樹脂が、（Ａ）ポリカーボネート系樹脂５０〜９８重量部、（Ｂ）スチレン系重合体４９〜０重量部、（Ｃ）グラフト共重合体１〜３０重量部からなる樹脂組成物である［１］記載の難燃性樹脂組成物、
［４］（Ｂ）スチレン系重合体が、（ｂ１）芳香族ビニル単量体成分、及び（ｂ２）シアン化ビニル単量体成分を含む共重合体であり、（Ｃ）グラフト共重合体が、（ｃ１）芳香族ビニル単量体成分、（ｃ２）シアン化ビニル単量体成分、及び（ｃ３）アルキル（メタ）アクリレート単量体成分のうちの少なくとも１種あるいは２種以上が（ｃ４）ゴム質重合体にグラフト重合された共重合体である［３］記載の難燃性樹脂組成物、
［５］（Ｃ）成分が、（ｃ１）芳香族ビニル単量体成分および（ｃ２）シアン化ビニル単量体成分が（ｃ４）ゴム質重合体にグラフト重合された共重合体と、（ｃ３）アルキル（メタ）アクリレート単量体成分が（ｃ４）ゴム質重合体にグラフト重合された共重合体の組み合わせからなることを特徴とする［４］記載の難燃性樹脂組成物、
［６］（α）熱可塑性樹脂が、ポリフェニレンエーテル系樹脂１０〜９９重量部とポリスチレン系樹脂９０〜１重量部からなる樹脂組成物である［１］記載の難燃性樹脂組成物、
［７］（β）有機リン化合物が、式（１）で表される１種または２種以上のオリゴマー系有機リン化合物である［１］〜［６］のいずれかに記載の難燃性樹脂組成物、
That is, the present invention
[1] Flame retardant resin containing (α) 100 parts by weight of a thermoplastic resin, (β) 1 to 30 parts by weight of an organic phosphorus compound, and (γ) 0.01 to 5 parts by weight of an alicyclic epoxy-based stabilizer Composition,
[2] The flame-retardant resin composition according to [1], wherein the (α) thermoplastic resin is a polycarbonate resin or a polyphenylene ether resin.
[3] The thermoplastic resin (α) comprises (A) 50 to 98 parts by weight of a polycarbonate resin, (B) 49 to 0 parts by weight of a styrene polymer, and (C) 1 to 30 parts by weight of a graft copolymer. The flame-retardant resin composition according to [1], which is a resin composition,
[4] (B) the styrene-based polymer is a copolymer containing (b1) an aromatic vinyl monomer component and (b2) a vinyl cyanide monomer component, and (C) a graft copolymer. At least one or two or more of (c1) an aromatic vinyl monomer component, (c2) a vinyl cyanide monomer component, and (c3) an alkyl (meth) acrylate monomer component as (c4) The flame-retardant resin composition according to [3], which is a copolymer obtained by graft-polymerizing a rubbery polymer,
[5] The component (C) is a copolymer obtained by graft-polymerizing (c1) an aromatic vinyl monomer component and (c2) a vinyl cyanide monomer component onto a rubber polymer (c4); (4) The flame-retardant resin composition according to (4), wherein the alkyl (meth) acrylate monomer component comprises (c4) a combination of a copolymer obtained by graft polymerization to a rubber polymer.
[6] The flame-retardant resin composition according to [1], wherein the (α) thermoplastic resin is a resin composition comprising 10 to 99 parts by weight of a polyphenylene ether resin and 90 to 1 part by weight of a polystyrene resin.
[7] The flame-retardant resin according to any one of [1] to [6] , wherein the (β) organophosphorus compound is one or more oligomeric organophosphorus compounds represented by the formula (1). Composition,
［９］ （β）有機リン化合物が、式（１）で表される１種または２種以上のオリゴマー系有機リン化合物であり、その平均縮合度Ｎが１以上１．２未満である［１］〜［６］のいずれかに記載の難燃性樹脂組成物、
［１０］（β）有機リン化合物が、式（２）で表される１種または２種以上のオリゴマー系有機リン化合物であり、その平均縮合度Ｎが１以上１．２未満である［１］〜［６］のいずれかに記載の難燃性樹脂組成物、
［１１］（β）有機リン化合物の酸価が３ｍｇＫＯＨ／ｇ以下である［１］〜［１０］のいずれかに記載の難燃性樹脂組成物、
［１２］さらにポリテトラフルオロエチレンを含む［１］〜［１１］のいずれかに記載の難燃性樹脂組成物である。
[9] (β) The organophosphorus compound is one or more oligomeric organophosphorus compounds represented by the formula (1), and the average degree of condensation N is 1 or more and less than 1.2. ] The flame-retardant resin composition according to any one of [6],
[10] (β) The organophosphorus compound is one or more oligomeric organophosphorus compounds represented by the formula (2), and the average degree of condensation N is 1 or more and less than 1.2. ] The flame-retardant resin composition according to any one of [6],
[11] The flame-retardant resin composition according to any one of [1] to [10] , wherein the (β) organic phosphorus compound has an acid value of 3 mgKOH / g or less.
[12] The flame-retardant resin composition according to any one of [1] to [11] , further comprising polytetrafluoroethylene.
【００６０】
【実施例】
以下実施例により本発明を具体的に説明する。用いた材料を以下に示す。
１．熱可塑性樹脂（α）成分
（ポリカーボネート：ＰＣ）
ビスフェノールＡとジフェニルカーボネートから溶融エステル交換法により製造されたＭｗが２０，５００であり、ヒドロキシ基末端量が３０％のビスフェノールＡ系ポリカーボネート
（ポリフェニレンエーテル：ＰＰＥ）
米国特許４，７８８，２７７号明細書（特願昭６２−７７５７０号）に記載されている方法に従ってジブチルアミンの存在下に、２，６−キシレノールを酸化カップリング重合して製造されたもので、ηＳＰ／Ｃ＝０．４２であり、溶融粘度は２８０℃で１４０ｓｅｃ−１のせん断速度で測定し、４９，０００ｐｏｉｓｅである。
（アクリロニトリル・スチレン共重合体：ＳＡＮ）
アクリロニトリル単位２５．０ｗｔ％、スチレン単位７５．０ｗｔ％からなるＭｗが１４０，０００のアクリロニトリル・スチレン共重合体
（ポリスチレン：ＧＰＰＳ）
旭化成工業（株）製 スタイロン６８５
（アクリロニトリル・ブタジエン・スチレン共重合体ゴム：ＡＢＳ）
１０メッシュ残分が、９０％未満であるパウダー状ＡＢＳ樹脂（三菱レーヨン（株）社製、商品名 ＲＣ）
（ハイインパクトポリスチレン：ＨＩＰＳ）
旭化成工業（株）製 スタイロンＨ９４０５
（メチルメタクリレート・スチレン・ブタジエン共重合体ゴム：ＭＢＳ）
最外層がメチルメタクリレートで被覆されたメチルメタクリレートグラフトスチレン・ブタジエンゴム（三菱レーヨン（株）社製、商品名 メタブレンＣ−２３３Ａ）
（メチルメタクリレートグラフトシリコンアクリル複合ゴム：シリコンアクリル複合ゴム）
最外層がメチルメタクリレートで被覆されたポリオルガノシロキサン成分およびポリアルキル（メタ）アクリレートゴム成分が相互進入網目構造を有している複合ゴム（三菱レーヨン（株）社製、商品名 メタブレンＳ−２００１）
２．有機リン化合物（β）成分
（有機リン化合物（β１））
下記参考例１の方法により得られた有機リン化合物
[0060]
【Example】
Hereinafter, the present invention will be described specifically with reference to examples. The materials used are shown below.
1. Thermoplastic resin (α) component (polycarbonate: PC)
Bisphenol A-based polycarbonate (polyphenylene ether: PPE) having a Mw of 20,500 produced from bisphenol A and diphenyl carbonate by a melt transesterification method and having a hydroxy group terminal content of 30%.
It is produced by oxidative coupling polymerization of 2,6-xylenol in the presence of dibutylamine according to the method described in U.S. Pat. No. 4,788,277 (Japanese Patent Application No. 62-77570). , Η SP / C = 0.42, and the melt viscosity is 49,000 poise, measured at 280 ° C. at a shear rate of 140 sec −1 .
(Acrylonitrile / styrene copolymer: SAN)
Acrylonitrile-styrene copolymer (polystyrene: GPPS) having an Mw of 140,000 consisting of 25.0 wt% of acrylonitrile units and 75.0 wt% of styrene units
Styron 685 manufactured by Asahi Kasei Corporation
(Acrylonitrile-butadiene-styrene copolymer rubber: ABS)
Powdered ABS resin with 10 mesh residue less than 90% (RC name, manufactured by Mitsubishi Rayon Co., Ltd.)
(High impact polystyrene: HIPS)
Styron H9405 manufactured by Asahi Kasei Kogyo Co., Ltd.
(Methyl methacrylate / styrene / butadiene copolymer rubber: MBS)
Methyl methacrylate grafted styrene / butadiene rubber whose outermost layer is coated with methyl methacrylate (Metablene C-233A, manufactured by Mitsubishi Rayon Co., Ltd.)
(Methyl methacrylate grafted silicone acrylic composite rubber: silicone acrylic composite rubber)
Composite rubber in which a polyorganosiloxane component and a polyalkyl (meth) acrylate rubber component each having an outermost layer coated with methyl methacrylate have a mutual intrusion network structure (trade name: METABLEN S-2001, manufactured by Mitsubishi Rayon Co., Ltd.)
2. Organic phosphorus compound (β) component (organic phosphorus compound (β1))
Organic phosphorus compounds obtained by the method of Reference Example 1 below
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11176719A JP2001002945A (en) | 1999-06-23 | 1999-06-23 | Stabilized flame retardant resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11176719A JP2001002945A (en) | 1999-06-23 | 1999-06-23 | Stabilized flame retardant resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001002945A JP2001002945A (en) | 2001-01-09 |
| JP2001002945A5 true JP2001002945A5 (en) | 2006-07-27 |
Family
ID=16018588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11176719A Pending JP2001002945A (en) | 1999-06-23 | 1999-06-23 | Stabilized flame retardant resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001002945A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100486979C (en) | 2001-02-08 | 2009-05-13 | 旭瑞达有限公司 | Process for purification of phosphate esters |
| JP2003155416A (en) * | 2001-11-22 | 2003-05-30 | Teijin Chem Ltd | Flame-retardant thermoplastic resin composition and its injection molded article |
| US6717005B2 (en) | 2002-05-13 | 2004-04-06 | Akzo Nobel N.V. | Epoxy-stabilized polyphosphate compositions |
| EP1693412A4 (en) * | 2003-12-10 | 2008-12-03 | Teijin Chemicals Ltd | Flame-retardant styrene resin composition and molded article obtained therefrom |
| JP5571399B2 (en) * | 2010-01-27 | 2014-08-13 | 帝人株式会社 | Flame-retardant styrenic resin composition and molded product therefrom |
| JP5558146B2 (en) * | 2010-03-15 | 2014-07-23 | 旭化成ケミカルズ株式会社 | Resin composition |
| JP5502819B2 (en) * | 2011-08-24 | 2014-05-28 | 帝人株式会社 | Flame retardant resin composition and molded product therefrom |
-
1999
- 1999-06-23 JP JP11176719A patent/JP2001002945A/en active Pending
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