JP6457948B2 - 有機着色剤および良好な加工特性を有する着色ポリマー組成物 - Google Patents
有機着色剤および良好な加工特性を有する着色ポリマー組成物 Download PDFInfo
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- JP6457948B2 JP6457948B2 JP2015548471A JP2015548471A JP6457948B2 JP 6457948 B2 JP6457948 B2 JP 6457948B2 JP 2015548471 A JP2015548471 A JP 2015548471A JP 2015548471 A JP2015548471 A JP 2015548471A JP 6457948 B2 JP6457948 B2 JP 6457948B2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 4
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- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
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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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
-
- 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
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- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
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- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
- C08K5/08—Quinones
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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
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- 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
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- 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
- C08K5/3465—Six-membered rings condensed with carbocyclic rings
-
- 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
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- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Description
R1およびR2は、各々、互いに独立して、直鎖状もしくは分岐鎖状アルキルラジカルまたはハロゲンであり、好ましくは、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、tert‐ブチル、ペンチル、ネオペンチル、ヘキシル、テキシル(thexyl)、またはClであり、より好ましくは、メチルまたはCl、特に好ましくは、Clであり、
nは、0から4の範囲の自然数である。
RaおよびRbは、各々、互いに独立して、直鎖状もしくは分岐鎖状アルキルラジカルまたはハロゲンであり、好ましくは、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、tert‐ブチル、ペンチル、ネオペンチル、ヘキシル、テキシル、またはClであり、より好ましくは、メチルまたはCl、特に好ましくは、Clであり、
nは、特定のラジカルRとは無関係に、0から3の範囲の自然数であり、n=0の場合、ラジカルは水素である。
RcおよびRdは、各々、互いに独立して、直鎖状もしくは分岐鎖状アルキルラジカルまたはハロゲンであり、好ましくは、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、tert‐ブチル、ペンチル、ネオペンチル、ヘキシル、テキシル、またはClであり、より好ましくは、メチルまたはCl、特に好ましくは、Clであり、
nは、特定のラジカルRとは無関係に、0から3の範囲の自然数であり、n=0の場合、ラジカルは水素である。
ホスフェートをベースとする少なくとも1つの安定化剤または加工助剤。ホスフェートは、以下の構造(9)を有し、
所望に応じて存在してよい、組成物の総重量に基づいて、0.0重量%から1.0重量%、好ましくは、0.01重量%から0.50重量%、特に好ましくは、0.01重量%から0.40重量%の1つ以上の離型剤。本発明の組成物に特に適する離型剤は、ペンタエリスリチルテトラステアレート(PETS)またはグリセリルモノステアレート(GMS)、好ましくは、PETSである。
所望に応じて存在してよい、0.00重量%から20.00重量%、好ましくは、0.05重量%から10.00重量%、より好ましくは、0.10重量%から1.00重量%、なおより好ましくは、0.10重量%から0.50重量%、非常に特に好ましくは、0.10重量%から0.30重量%の少なくとも1つのUV(紫外線)吸収剤。
ことも可能である。
所望に応じて存在してよい、組成物の総重量に基づいて0.00重量%〜0.20重量%、好ましくは、0.01重量%〜0.10重量%、より好ましくは、0.01重量%から0.05重量%、特に好ましくは、0.015重量%から0.040重量%の、好ましくは、ホスフィン、ホスファイト、およびフェノール系抗酸化剤、ならびにさらにはこれらの混合物から成る群より選択されるc)とは異なる1つ以上の熱または加工安定化剤。
熱可塑性ポリマー、好ましくは、透明熱可塑性ポリマー、好ましくは、ポリカーボネート、コポリカーボネート、ポリエステルカーボネート、ポリスチレン、スチレンコポリマー、ポリエチレンテレフタレート(PET)、PET‐シクロヘキサンジメタノールコポリマー(PETG)、ポリエチレンナフタレート(PEN)、ポリブチレンテレフタレート(PBT)などの芳香族ポリエステル、環状ポリオレフィン、ポリアクリレートまたはコポリアクリレート、およびポリメタクリレートまたはコポリメタクリレート、例えば、ポリメチルまたはコポリメチルメタクリレート(PMMAなど)およびさらには、スチレンとのコポリマー、例えば、透明ポリスチレン‐アクリロニトリル(PSAN)、熱可塑性ポリウレタン、環状オレフィンをベースとするポリマー(例:TOPAS(登録商標)、チコナ(Ticona)製の市販品)、より好ましくは、ポリカーボネート、コポリカーボネート、ポリエステルカーボネート、芳香族ポリエステル、もしくはポリメチルメタクリレート、または述べた成分の混合物、特に好ましくは、ポリカーボネートおよびコポリカーボネートを含み、透明熱可塑性ポリマーは、他のすべての成分と合計して100重量%となるような量で添加される。
透過率測定は、ISO 13468‐2に従い、光度計積分球(photometer sphere)を有するパーキンエルマー製Lambda 900分光光度計で行った(すなわち、拡散透過率および直接透過率を測定することによって全透過率を特定する)。
ΔEは、ASTEM D 2244に従う知覚された色差に対する算出値である。本実験の場合、光源D65/10°を用いた。ASTM D 2244の式7を用いてΔE値の算出を行った。
成分b)
式(1)のアントラキノン系着色剤として、レバークーゼンのランクセス社製のR=t‐ブチルであるMacrolex Grun G(Solvent Green 28;CAS 28198‐05‐2)を用いる。
式(2)のアントラキノン系着色剤として、レバークーゼンのランクセス社製のR=HであるMacrolex Violet B(Solvent Violet 13;CAS 81‐48‐1)を用いる。
本発明に従うものではないアントラキノン系着色剤として、レバークーゼンのランクセス社製Macrolex Grun 5B(Solvent Green 3;CAS 128‐80‐3)を用いる。
本発明に従うものではないアントラキノン系着色剤として、レバークーゼンのランクセス社製Macrolex Violet 3R(Solvent Violet 36;CAS 61951‐89‐1)を用いる。
本発明に従うホスフェート系安定化剤として、トリオクチルホスフェート(TOF;トリス‐2‐エチルヘキシルホスフェート;CAS 78‐42‐2)を用いる。
本発明に従うものではない安定化剤として、トリフェニルホスフィン(TPP)(CAS 603‐35‐0)を用いる。
本発明に従うものではない安定化剤として、Irgafos PEP‐Q(CAS 119345‐01‐6)を用いる。
本発明に従うものではない安定化剤として、Irganox B900(Irgafos 168(80%)およびIrganox 1076(20%)の混合物;Irgafos 168(トリス(2,4‐ジ‐tert‐ブチルフェニル)ホスファイト;CAS 31570‐04‐4);Irganox 1076(オクタデシル3‐(3,5‐ジ‐tert‐ブチル‐4‐ヒドロキシフェニル)プロピオネート;を用いる。
本発明に従うものではない安定化剤として、Doverphos S 9228(ビス(2,4‐ジクミルフェニル)ペンタエリスリトールジホスファイト(CAS 154862‐43‐8))を用いる。
ペレットを、120℃にて3時間減圧乾燥した。
Claims (13)
- 改善された色安定性を有し:
a)その他の成分と一緒に合計して100重量%となる割合の熱可塑性ポリマー、
b)0.000001重量%から1.000000重量%の割合の、少なくとも1つの遊離ヒドロキシル官能基を有する少なくとも1つのアントラキノンをベースとした着色剤、
c)モノヘキシル、ジヘキシル、およびトリヘキシルホスフェート、トリイソオクチルホスフェート、ならびにトリノニルホスフェートから成る群より選択され、0.00005から0.05000重量%の割合で存在する、少なくとも1つの安定化剤、
を含むポリマー組成物。 - 以下の成分d)〜g):
d)前記組成物の総重量に基づいて0.0重量%から1.0重量%の1つ以上の離型剤、
e)前記組成物の総重量に基づいて0.0重量%から20.00重量%の1つ以上のUV吸収剤、
f)前記組成物の総重量に基づいて0.00重量%から0.20重量%のc)とは異なる1つ以上の熱または加工安定化剤
g)前記組成物の総重量に基づいて0.0重量%から5.0重量%の1つ以上のさらなる添加剤
を含むことを特徴とする、請求項1に記載の組成物。 - 各々の場合において前記組成物の総重量に基づいた割合で成分b)〜g):
b)0.00005重量%から0.50000重量%の割合の、少なくとも1つの遊離ヒドロキシル官能基を有する少なくとも1つのアントラキノンをベースとした着色剤、
c)0.0002重量%から0.0500重量%の割合の、モノヘキシル、ジヘキシル、およびトリヘキシルホスフェート、トリイソオクチルホスフェート、ならびにトリノニルホスフェートから成る群より選択される少なくとも1つの安定化剤、
d)前記組成物の総重量に基づいて0.01重量%から0.50重量%の1つ以上の離型剤
e)前記組成物の総重量に基づいて0.05重量%から10.00重量%の1つ以上のUV吸収剤、
f)前記組成物の総重量に基づいて0.01重量%から0.05重量%のc)とは異なる1つ以上の熱または加工安定化剤
g)前記組成物の総重量に基づいて0.01重量%から1.00重量%の1つ以上のさらなる添加剤
を含むことを特徴とする、請求項1または2に記載の組成物。 - 前記熱可塑性ポリマーが、ポリカーボネートであることを特徴とする、請求項1から3のいずれか一項に記載の組成物。
- 前記着色剤が、以下の構造:
から成る群より選択されることを特徴とする、請求項1から4のいずれか一項に記載の組成物。 - 前記式1のRxおよびRyが、n‐ブチル、tert‐ブチル、またはメチルであり、
前記式2のRが、Hである、請求項5に記載の組成物。 - 成分c)が、トリイソオクチルホスフェートであることを特徴とする、請求項1から6のいずれか一項に記載の組成物。
- 前記組成物が、アントラキノンをベースとする、ペリノンをベースとする、およびフタロシアニンをベースとする着色剤の群より選択される成分b1)のさらなる着色剤の少なくとも1つを含むことを特徴とする、請求項1から7のいずれか一項に記載の組成物。
- 前記組成物が、構造(3)から(8):
から成る群より選択される前記成分b1)のさらなる着色剤を含むことを特徴とする、請求項8に記載の組成物。 - 請求項1〜9のいずれか一項に記載の組成物のうちの1つを用いて作製された成型品。
- 自動車の窓であることを特徴とする、請求項10に記載の成型品。
- a)請求項1〜9のいずれか一項に記載の組成物から成る基材層、
b)耐引っ掻き性層としての少なくとも1つのカバー層
を含む多層品。 - 前記層b)が、UV保護層を追加で含むことを特徴とする、請求項12に記載の多層品。
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DE102009059771A1 (de) * | 2009-12-21 | 2011-06-22 | Bayer MaterialScience AG, 51373 | Polycarbonat mit verbesserten thermischen und mechanischen Eigenschaften sowie reduziertem thermischen Ausdehnungskoeffizienten |
IT1403380B1 (it) * | 2010-12-17 | 2013-10-17 | Bayer Materialscience Ag | Composizione di polimeri con caratteristiche di assorbimento di calore ad alta stabilità agli agenti atmosferici. |
ITRM20100667A1 (it) * | 2010-12-17 | 2012-06-18 | Bayer Materialscience Ag | Composizione di polimeri con caratteristiche di assorbimento di calore ad alta stabilità agli agenti atmosferici. |
ITRM20100670A1 (it) | 2010-12-17 | 2012-06-18 | Bayer Materialscience Ag | Colorante organico e composizioni polimeriche colorate ad alta stabilità agli agenti atmosferici. |
CN103946310B (zh) * | 2011-11-30 | 2016-03-02 | 拜耳知识产权有限责任公司 | 由聚碳酸酯制成的带有深色光泽效果的多层制品 |
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2013
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- 2013-12-18 CN CN201380073476.1A patent/CN104995247B/zh active Active
- 2013-12-18 US US14/654,293 patent/US20150368434A1/en not_active Abandoned
- 2013-12-18 EP EP13811194.3A patent/EP2935437A1/de active Pending
- 2013-12-18 JP JP2015548471A patent/JP6457948B2/ja active Active
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CN104995247A (zh) | 2015-10-21 |
KR102258329B1 (ko) | 2021-06-01 |
KR20150096738A (ko) | 2015-08-25 |
US20150368434A1 (en) | 2015-12-24 |
WO2014095967A1 (de) | 2014-06-26 |
JP2016507607A (ja) | 2016-03-10 |
CN104995247B (zh) | 2018-05-08 |
EP2935437A1 (de) | 2015-10-28 |
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