JP2023036025A - 乳化重合体粒子を含む消光剤、これを含む消光性高分子組成物及びこの製造方法 - Google Patents
乳化重合体粒子を含む消光剤、これを含む消光性高分子組成物及びこの製造方法 Download PDFInfo
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- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- KZOIWQKIVZDOGH-UHFFFAOYSA-M didodecyl(dimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC KZOIWQKIVZDOGH-UHFFFAOYSA-M 0.000 description 1
- VBVQYGNPGUXBIS-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC VBVQYGNPGUXBIS-UHFFFAOYSA-M 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- VVSMKOFFCAJOSC-UHFFFAOYSA-L disodium;dodecylbenzene;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 VVSMKOFFCAJOSC-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- JVQOASIPRRGMOS-UHFFFAOYSA-M dodecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)C JVQOASIPRRGMOS-UHFFFAOYSA-M 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- STYCVOUVPXOARC-UHFFFAOYSA-M trimethyl(octyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)C STYCVOUVPXOARC-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Description
(a)反応器に、前記第1重合性組成物、脱イオン水、乳化剤及び酸化合物を添加及び撹拌してプレエマルジョンを製造するステップと、
(b)水溶性開始剤を投入して反応を開始し、乳化重合するステップと、を含むものであってもよい。
1)平均粒径:粒度分析装置(Malvern社のMastersizer 3000)を用いて測定した。
2)表面光沢度(GLOSS):ASTM D523に基づいて60°及び85°で測定した。
3)IZOD衝撃強度(Noched IZOD Impact strength):衝撃強度をASTM D256に基づいて1/4”及び1/8”で測定した。
4)引張強度(tensile strength) :引張強度をASTM D638に基づいて測定した。
5)黄色度(YI、Yellow Index):3.2mmの厚さの射出成形品を製造し、黄色度をASTM D1925に基づいて測定した。
(A)コア層の製造ステップ
スチレン23g、アクリロニトリル9g、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート(CEL-2021、ダイセルケム)3g及びドデシルベンゼンスルホン酸(95wt%、SAMCHUN化学)0.35gを反応器に投入して撹拌した。その後、脱イオン水200g及びロジン酸カリウム2.0gをさらに投入した後に200rpm以上の撹拌速度で30分以上撹拌した。反応器内の組成物がミルク色のプレエマルジョン状態となったことを確認した後に60℃に昇温した。反応器にカリウムパースルフェート0.15gを投入して反応を開始し、その後に発熱反応を調節しながら反応器の内部温度を70℃に保持し、2時間乳化重合を行い、これにより乳化重合体粒子のコア層を製造した(重合転換率97%)。
前記(A)ステップに続いて、内部温度70℃の反応器にスチレン43g、アクリロニトリル16g及び3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート6gを混合した組成物を2時間連続に滴下した後、発熱反応を調節しながら温度を70℃に保持し、2時間乳化重合を行った。反応完了後、反応器の内部温度を40℃以下に冷却して乳化重合体粒子を含む分散液(エマルジョン)を収得した(重合転換率98%、固形分33%)。
前記実施例1の(A)ステップで、アクリロニトリルを投入せずにスチレン32gを投入することを除き、実施例1と同様に行った。前記乳化重合体粒子の平均粒径は160nmと測定された。
前記実施例1の(A)ステップで、スチレン24g及び3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート2gを投入することと、(B)ステップで、スチレン44g、アクリロニトリル17g及び3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート4gを投入することを除き、実施例1と同様に行った。前記乳化重合体粒子の平均粒径は180nmと測定された。
前記実施例1の(A)ステップで、アクリロニトリル8g及び3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート4gを投入することと、(B)ステップで、スチレン42g、アクリロニトリル15g及び3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレート8gを投入することを除き、実施例1と同様に行った。前記乳化重合体粒子の平均粒径は215nmと測定された。
前記実施例1の(A)ステップで、スチレンと共にジビニルベンゼン0.1gをさらに投入することと、(B)ステップで、スチレンと共にジビニルベンゼン0.3gをさらに投入することを除き、実施例1と同様に行った。前記乳化重合体粒子の平均粒径は140nmと測定された。
前記実施例1の(A)ステップで、ドデシルベンゼンスルホン酸を投入せず、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレートの代わりにジビニルベンゼン3gを投入することと、(B)ステップで、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキシルカルボキシレートの代わりにジビニルベンゼン6gを投入することを除き、実施例1と同様に行い、収得されたエマルジョンの重合転換率は97%以上であり、固形分は36%であった。以後の過程も実施例1と同様に行った。前記乳化重合体粒子の平均粒径は118nmと測定された。
[実施例6~10及び比較例2~4]
PC(3020PJ)65.5wt%、ABS(IM-601)11.4wt%、SAN(92HR)18wt%及び酸化防止剤0.3wt%と前記実施例1~5及び比較例1に係る乳化重合体粒子4.7wt%を混合した後、押出機によって消光性高分子組成物ペレットを得て、前記ペレットを乾燥して射出機で横、縦及び厚さが70mm×75mm×3.0mmの試験片と、単一シート押出機で横、縦及び厚さが100mm×75mm×2.0mmのシート状の試験片を製造した。製造した射出成形品及び押出シートの物性を測定し、下記表1に示した。
前記実施例6において、前記乳化重合体粒子の代わりに米国公開特許US5580924AによるSAN Gel-1を同量投入したことを除き、実施例6と同様に行った。製造した射出成形品及び押出シートの物性を測定し、下記表1に示した。
前記実施例6でABS(IM-601)の代わりにASA(XC-500A)を同量投入したことを除き、実施例6と同様に行った。製造した射出成形品及び押出シートの物性を測定し、下記表2に示した。
Claims (21)
- 芳香族ビニル化合物、不飽和ニトリル化合物及び脂環族エポキシ化合物を含む重合性組成物から製造され、前記脂環族エポキシ化合物のエポキシ基は開環したものである、乳化重合体粒子。
- 前記脂環族エポキシ化合物は、2個以上のエポキシ基を有するものである、請求項1に記載の乳化重合体粒子。
- 前記脂環族エポキシ化合物は、3,4-エポキシシクロヘキシルメチル3,4-エポキシシクロヘキサン-カルボキシレート、ジエチレングリコールビス(3,4-エポキシシクロヘキサン-カルボキシレート)、2-エチル-1,3-ヘキサンジオールビス(3,4-エポキシシクロヘキサン-カルボキシレート)、ジエチレングリコールビス(3,4-エポキシ-6-メチルシクロヘキサン-カルボキシレート)、3-メチル-1,5-ペンタンジオールビス(3,4-エポキシシクロヘキサン-カルボキシレート)、1,5-ペンタンジオールビス(3,4-エポキシシクロヘキサン-カルボキシレート)、エチレングリコールビス(3,4-エポキシシクロヘキサン-カルボキシレート)、エチレングリコールビス(3,4-エポキシ-6-メチルシクロヘキサン-カルボキシレート)、ビス(3,4-エポキシシクロヘキシルメチル)オキサレート、ビス(3,4-エポキシシクロヘキシルメチル)スクシネート、ビス(3,4-エポキシシクロヘキシルメチル)アジペート及び1,2,8,9-ジエポキシリモネンからなる群から選択される1つ以上である、請求項1に記載の乳化重合体粒子。
- 前記重合性組成物は、芳香族ビニル化合物100重量部に対して、不飽和ニトリル化合物を20~45重量部及び脂環族エポキシ化合物を3~25重量部で含んで製造される、請求項1に記載の乳化重合体粒子。
- 前記重合性組成物は、R1COOH、R2SO3H及びこれらの塩化合物からなる群から選択されるいずれか1つまたは2つ以上の酸化合物をさらに含み、
前記R1及びR2は独立してC6-30アルキル、C6-30アリールまたはC6-30アルC6-30アルキルである、請求項1に記載の乳化重合体粒子。 - 前記重合性組成物は、芳香族ビニル化合物100重量部に対して、前記酸化合物を0.05~1重量部で含む、請求項5に記載の乳化重合体粒子。
- 前記重合性組成物は水と混合されて分散相を形成し、且つ
前記酸化合物は、分散相と水相の界面に位置して前記重合性組成物が重合されるものである、請求項5に記載の乳化重合体粒子。 - 前記乳化重合体粒子の表面は負に荷電されたものである、請求項1に記載の乳化重合体粒子。
- 前記乳化重合体粒子の平均粒径は90~250nmである、請求項1に記載の乳化重合体粒子。
- 請求項1乃至9のいずれか一項に記載の乳化重合体粒子を含む消光剤。
- 請求項10に記載の消光剤を含むマスターバッチチップ。
- 請求項10に記載の消光剤及び熱可塑性高分子を含む消光性高分子組成物。
- 前記熱可塑性高分子は、ポリプロピレン(PP)、ポリアクリレート(polyacrylate)、ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート(PBT)、ポリメチルメタクリレート(PMMA)、ポリカーボネート(PC)、ポリアミド(polyamide)、スチレン-アクリロニトリル共重合体(SAN)、アクリロニトリル-ブタジエン-スチレン(ABS)、アクリロニトリル-スチレン-アクリレート(ASA)及びこれらの混合物からなる群から選択される1つ以上である、請求項12に記載の組成物。
- 請求項12に記載の消光性高分子組成物を押出または射出して製造した成形品。
- 芳香族ビニル化合物及び脂環族エポキシ化合物を含む第1重合性組成物を水相で乳化重合してコア層を製造するステップと、
前記コア層の存在下で芳香族ビニル化合物、不飽和ニトリル化合物及び脂環族エポキシ化合物を含む第2重合性組成物を乳化重合してシェル層を製造するステップと、を含む、乳化重合体粒子の製造方法。 - 前記第1重合性組成物は、芳香族ビニル化合物100重量部に対して、脂環族エポキシ化合物を1~20重量部で含み、
前記第2重合性組成物は、前記芳香族ビニル化合物及び不飽和ニトリル化合物の総合である100重量部に対して、脂環族エポキシ化合物を2~18重量部で含むものである、請求項15に記載の乳化重合体粒子の製造方法。 - 前記コア層を製造するステップは、
(a)反応器に、前記第1重合性組成物、脱イオン水、乳化剤及び酸化合物を添加及び撹拌してプレエマルジョンを製造するステップと、
(b)水溶性開始剤を投入して反応を開始し、乳化重合するステップと、を含むものである、請求項15に記載の乳化重合体粒子の製造方法。 - 前記酸化合物は、R1COOH、R2SO3H及びこれらの塩化合物からなる群から選択されるいずれか1つまたは2つ以上の組み合わせであり、
前記R1及びR2は独立してC6-30アルキル、C6-30アリールまたはC6-30アルC6-30アルキルである、請求項17に記載の乳化重合体粒子の製造方法。 - 前記シェル層を製造するステップは、
前記コア層の存在下で前記第2重合性組成物を滴下し、乳化重合して乳化重合体粒子分散液を製造するステップを含むものである、請求項15に記載の乳化重合体粒子の製造方法。 - 前記乳化重合体粒子は、コア層が5~60wt%及びシェル層が40~95wt%で含まれるものである、請求項15に記載の乳化重合体粒子の製造方法。
- 前記乳化重合体粒子分散液の固形分含量(solid content)が20~45wt%である、請求項19に記載の乳化重合体粒子の製造方法。
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