JP7479406B2 - 難燃性樹脂組成物およびその成形品 - Google Patents
難燃性樹脂組成物およびその成形品 Download PDFInfo
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- JP7479406B2 JP7479406B2 JP2021576214A JP2021576214A JP7479406B2 JP 7479406 B2 JP7479406 B2 JP 7479406B2 JP 2021576214 A JP2021576214 A JP 2021576214A JP 2021576214 A JP2021576214 A JP 2021576214A JP 7479406 B2 JP7479406 B2 JP 7479406B2
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- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- CENHPXAQKISCGD-UHFFFAOYSA-N trioxathietane 4,4-dioxide Chemical compound O=S1(=O)OOO1 CENHPXAQKISCGD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- SGKKYCDALBXNCG-UHFFFAOYSA-N tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-5-methylphenyl] phosphite Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C(=CC(OP(OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)=C(C=2)C(C)(C)C)C)=C1 SGKKYCDALBXNCG-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- 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
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- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
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- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
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- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Description
(A)成分:酸未変性ポリオレフィン系樹脂
(B)成分:オルトリン酸メラミン、ピロリン酸メラミンおよびポリリン酸メラミンからなる群から選択される1種以上のメラミン塩
(C)成分:オルトリン酸ピペラジン、ピロリン酸ピペラジンおよびポリリン酸ピペラジンからなる群から選択される1種以上のピペラジン塩
(D)成分:ガラス繊維
(E)成分:酸価が5~100KOHmg/gであり、重量平均分子量が10,000~100,000であるマレイン酸変性ポリオレフィンおよび無水マレイン酸変性ポリオレフィンから選ばれる1種以上
<難燃剤組成物>
本発明の難燃性樹脂組成物は、下記(A)~(E)成分を含有する。
(A)成分:酸未変性ポリオレフィン系樹脂
(B)成分:オルトリン酸メラミン、ピロリン酸メラミンおよびポリリン酸メラミンからなる群から選択される1種以上のメラミン塩
(C)成分:オルトリン酸ピペラジン、ピロリン酸ピペラジンおよびポリリン酸ピペラジンからなる群から選択される1種以上のピペラジン塩
(D)成分:ガラス繊維
(E)成分:酸価が5~100KOHmg/gであり、重量平均分子量が10,000~100,000である酸変性樹脂
(i)140℃に加熱したキシレン70mLに酸変性樹脂1gを溶解させる。
(ii)同温度でフェノールフタレインを指示薬として、0.1mol/L水酸化カリウムエタノール溶液(商品名「0.1mol/Lエタノール性水酸化カリウム溶液」、和光純薬(株)製)で滴定を行う。
(iii)滴定に要した水酸化カリウム量をmgに換算して酸価(単位:mgKOH/g)を算出する。
本発明の難燃性樹脂組成物は、助剤を含有してもよい。助剤としては、難燃助剤、ドリップ防止助剤、加工助剤等が挙げられる。難燃助剤は、金属酸化物や多価アルコール化合物を含むことができる。これにより、樹脂の難燃性を向上できる。
本発明の成形体は、本発明の難燃性樹脂組成物を成形することにより得られる。成形方法および成形条件については特に制限はなく、公知の成形方法および成形条件を用いることができる。具体的な成形方法としては、押出加工、カレンダー加工、射出成形、ロール、圧縮成形、ブロー成形、回転成形等が挙げられ、樹脂板、シート、フィルム、ボトル、繊維、異形品等の種々の形状の成形体を製造することができる。
(B)成分と(C)成分を、以下の製造例の方法で製造した。
(B)成分:メラミン塩
オルトリン酸メラミンを220℃で6時間、固相状態で加熱縮合反応させて、ピロリン酸メラミンを主成分とするメラミン塩を製造した。メラミン塩は精製せずにそのまま用いた。メラミン塩中のピロリン酸メラミンの純度は、98.5%だった。なお、純度は、イオンクロマトグラフ測定装置ICS-2100(サーモフィッシャーサイエンティフィック株式会社)、Dionex IonPac AS-19カラム(サーモフィッシャーサイエンティフィック株式会社)、電気伝導度検出器を用いて測定した。
(C)成分:ピペラジン塩
二リン酸ピペラジンを250℃で1時間、固相状態で加熱縮合反応させて、ピロリン酸ピペラジンを主成分とするピペラジン塩を製造した。ピペラジン塩は精製せずにそのまま用いた。ピペラジン塩中のピロリン酸ピペラジンの純度は、99.0%だった。なお、純度は、イオンクロマトグラフ測定装置ICS-2100(サーモフィッシャーサイエンティフィック株式会社)、Dionex IonPac AS-19カラム(サーモフィッシャーサイエンティフィック株式会社)、電気伝導度検出器を用いて測定した。
・実施例1~21、比較例1~14
表1~5に示す成分を同表に示す割合で配合し、さらに(A)成分である樹脂100質量部当たり、中和剤(ステアリン酸カルシウム)0.05質量部、フェノール系酸化防止剤(アデカスタブAO-60、ADEKA製)0.1質量部、リン系酸化防止剤(アデカスタブ2112、ADEKA製)0.1質量部を配合し、ヘンシェルミキサーで混合して難燃性樹脂組成物を得た。なお、表中の各成分の単位は質量部である。
得られたペレット状の難燃性樹脂組成物を射出成形機(NEX80、日精樹脂工業社製)にて成形し、UL-94V測定用試験片(127mm×12.7mm×1.6mm)を作製した。射出成形の加工条件は、実施例1~20および比較例1~13の組成物では、樹脂温度230℃、金型温度50℃の条件で行い、実施例21および比較例14の組成物では、樹脂温度200℃、金型温度50℃の条件で行った。得られた試験片を23℃、湿度60%RHの恒温恒湿槽内に7日間静置した後、UL-94V規格に準拠して燃焼ランクをつけた。燃焼ランクはV-0が最高のものであり、V-1、V-2となるにしたがって難燃性は低下する。ただし、V-0~V-2のランクの何れにも該当しないものはNR(No Rating)とした。結果を表1~5に併記する。
得られたペレット状の難燃性樹脂組成物を射出成形機(NEX80、日精樹脂工業社製)にて成形し、酸素指数測定用試験片(80mm×10mm×4mm)を作製した。射出成形の加工条件は、実施例1~20および比較例1~13の組成物では、樹脂温度230℃、金型温度50℃の条件で行い、実施例21および比較例14の組成物では、樹脂温度200℃、金型温度50℃の条件で行った。得られた試験片を23℃、湿度60%RHの恒温恒湿槽内に7日間静置した後、JIS K7201-2に準拠して試験片の酸素指数を測定した。酸素指数は、窒素と酸素の混合ガス中で、垂直の小型試験片が燃焼を維持する最少酸素濃度であり、この値が高いほど燃えにくいと言える。結果を表1~5に併記する。
得られたペレット状の難燃性樹脂組成物を射出成形機(NEX80、日精樹脂工業社製)にて成形し、荷重たわみ温度測定用試験片(80mm×10mm×4mm)を作製した。射出成形の加工条件は、実施例1~20および比較例1~13の組成物では、樹脂温度230℃、金型温度50℃の条件で行い、実施例21および比較例14の組成物では、樹脂温度200℃、金型温度50℃の条件で行った。得られた試験片を23℃、湿度60%RHの恒温恒湿槽内に7日間静置した後、ISO178に準拠して試験片の曲げ弾性率(MPa)を測定した。結果を表1~5に併記する。
得られたペレット状の難燃性樹脂組成物を射出成形機(NEX80、日精樹脂工業社製)にて成形し、荷重たわみ温度測定用試験片(80mm×10mm×4mm)を作製した。射出成形の加工条件は、実施例1~20および比較例1~13の組成物では、樹脂温度230℃、金型温度50℃の条件で行い、実施例21および比較例14の組成物では、樹脂温度200℃、金型温度50℃の条件で行った。得られた試験片を23℃、湿度60%RHの恒温恒湿槽内に7日間静置した後、ISO75-2(荷重1.8MPa)に準拠して、荷重たわみ温度(℃)を測定した。結果を表1~5に併記する。
得られたペレット状の難燃性樹脂組成物を射出成形機(NEX80、日精樹脂工業社製)にて成形し、シャルピー衝撃強さ測定用試験片(80mm×10mm×4mm)を作製した。射出成形の加工条件は、実施例1~20および比較例1~13の組成物では、樹脂温度230℃、金型温度50℃の条件で行い、実施例21および比較例14の組成物では、樹脂温度200℃、金型温度50℃の条件で行った。得られた試験片を23℃、湿度60%RHの恒温恒湿槽内に7日間静置した後、試験片にノッチを付与した。ノッチを付与した試験片を温度23℃、湿度60%RHの恒温恒湿槽内に5日間静置した後、恒温恒湿槽から試験片を取り出し、ISO179-1に準拠してシャルピー衝撃強度(kJ/m2)を測定した。結果を表1~5に併記する。
上記で得られたペレットの表面粗さの状態、切断面の気泡状態を目視により評価し加工性ランクを付けた。加工性ランクは以下の指標によって判定した。
A:表面荒れおよび切断面の気泡が目視で確認できず、実用上満足できる。
B:表面荒れまたは切断面の気泡が目視で確認でき、実用上不満足である。
表1~5中の無水マレイン酸変性ポリプロピレン、(E)-1~(E)-5および(E)’-1、(E)’-2の重量平均分子量(Mw)は、ゲル浸透クロマトグラフィーを用いて測定した。測定条件は以下のとおりである。
(装置名:Viscotek HT-GPC、スペクトリス(株)製)
溶媒 :オルトジクロロベンゼン
基準物質 :ポリスチレン
検出器 :屈折率検出器
カラム固定相:TSKgel GMHHR-HHT、2本直列、東ソー株式会社製
カラム温度 :140℃
サンプル濃度:3mg/1mL
流量 :1.0mL/min
注入量 :100μL
(A)-1:インパクトコポリマーポリプロピレン(メルトフローレート(JIS K7210に準拠、荷重2.16kg、温度230℃)=30g/10min)
(A)-2:ホモポリプロピレン(メルトフローレート(JIS K7210に準拠、荷重2.16kg、温度230℃)=30g/10min)
(A)-3:高密度ポリエチレン(メルトフローレート(JIS K7210に準拠、荷重2.16kg、温度190℃)=40g/10min
(B):メラミン塩(上述の製造例1で製造したもの)
(C):ピペラジン塩(上述の製造例2で製造したもの)
(D):ガラス繊維(チョップドストランドCS3PE-455S(日東紡績製、カット長3.0mm、単繊維径13μm))
(E)-1:無水マレイン酸変性ポリプロピレン1(酸価=9.5mgKOH/g、Mw=75,000)
(E)-2:無水マレイン酸変性ポリプロピレン2(酸価=47mgKOH/g、Mw=80,000)
(E)-3:無水マレイン酸変性ポリプロピレン3(酸価=66mgKOH/g、Mw=45,000)
(E)-4:無水マレイン酸変性ポリプロピレン4(酸価=52mgKOH/g、Mw=30,000)
(E)-5:無水マレイン酸変性ポリエチレン(酸価=19mgKOH/g、Mw=40,000)
(E)’-1:無水マレイン酸変性ポリプロピレン5(酸価=3.5mgKOH/g、Mw=9,000)
(E)’-2:無水マレイン酸変性ポリプロピレン6(酸価=21.4mgKOH/g、Mw=160,000)
(F):酸化亜鉛
Claims (9)
- 下記(A)~(E)成分を含有することを特徴とする難燃性樹脂組成物。
(A)成分:酸未変性ポリオレフィン系樹脂
(B)成分:オルトリン酸メラミン、ピロリン酸メラミンおよびポリリン酸メラミンからなる群から選択される1種以上のメラミン塩
(C)成分:オルトリン酸ピペラジン、ピロリン酸ピペラジンおよびポリリン酸ピペラジンからなる群から選択される1種以上のピペラジン塩
(D)成分:ガラス繊維
(E)成分:酸価が5~100KOHmg/gであり、重量平均分子量が10,000~100,000であるマレイン酸変性ポリオレフィンおよび無水マレイン酸変性ポリオレフィンから選ばれる1種以上 - (A)成分100質量部に対して、(B)成分と(C)成分との合計含有量が10~200質量部である請求項1記載の難燃性樹脂組成物。
- (A)成分100質量部に対して、(D)成分の含有量が5~200質量部である請求項1または2記載の難燃性樹脂組成物。
- (A)成分100質量部に対して、(E)成分の含有量が0.1~25質量部である請求項1~3のうちいずれか一項記載の難燃性樹脂組成物。
- (B)成分と(C)成分の含有比率が、質量比で20:80~60:40である請求項1~4のうちいずれか一項記載の難燃性樹脂組成物。
- (C)成分がピロリン酸ピペラジンを含有する請求項1~5のうちいずれか一項記載の難燃性樹脂組成物。
- さらに、(F)成分:酸化亜鉛を、(B)成分と(C)成分との合計100質量部に対して、0.01~10質量部含有する請求項1~6のうちいずれか一項記載の難燃性樹脂組成物。
- (A)成分がポリプロピレン系樹脂である請求項1~7のうちいずれか一項記載の難燃性樹脂組成物。
- 請求項1~8のうちいずれか一項記載の難燃性樹脂組成物から得られることを特徴とする成形体。
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