JP6184471B2 - 改善された光学的特性を有するポリアミド組成物 - Google Patents
改善された光学的特性を有するポリアミド組成物 Download PDFInfo
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- JP6184471B2 JP6184471B2 JP2015500889A JP2015500889A JP6184471B2 JP 6184471 B2 JP6184471 B2 JP 6184471B2 JP 2015500889 A JP2015500889 A JP 2015500889A JP 2015500889 A JP2015500889 A JP 2015500889A JP 6184471 B2 JP6184471 B2 JP 6184471B2
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- alkyl
- composition
- substituted
- unsubstituted
- butyl
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- 125000000217 alkyl group Chemical group 0.000 claims description 23
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
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- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- 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
- C08K5/21—Urea; Derivatives thereof, e.g. biuret
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Description
ポリアミド(PA)は、その非常に良好な性能特性と低コストのため、多くの種々の用途に、例えば自動車産業、機械工学産業、電気産業、エレクトロニクス産業、スポーツ産業および娯楽産業で広く使用される。ポリアミドはまた食品包装のために使用される。プレート、シート、フィルムおよびコンテナとして使用されるポリアミドのための多くの用途は、それを用いて貯蔵され、包装され、かつ/または覆われた物品の特定を促すために本質的な透明度を必要とし、かつ/または本質的に濁りがないことを必要とする。このように、透明なポリアミドを使用することが望ましい。しかしながら、多くのポリアミドは、半晶質であるため、該ポリアミド中に存在する結晶ドメインにより入射光が散乱するため光学的に不透明である。成核剤および透明剤は、通常は、工業的な実施において、光学的特性、例えば透明度、ヘイズまたはレーザ透過率を改善するために結晶化可能な熱可塑性ポリマーと組み合わせて使用される。非常に様々な成核剤および透明剤はポリプロピレンについて知られている。今までに、ポリアミド組成物のヘイズを下げる透明剤は知られていない。従って、ポリアミド組成物で使用できる透明剤に大きな需要が存在する。
xは、1、2または3であり、
R1およびR2は、互いに独立して、水素、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択され、かつ
Zは、C3〜C10−アルカンジイル、非置換もしくは置換されたアリーレン、非置換もしくは置換されたアリーレン−C1〜C4−アルキレン−アリーレン、非置換もしくは置換されたヘテロアリーレン、非置換もしくは置換されたヘテロアリーレン−C1〜C4−アルキレン−ヘテロアリーレン、非置換もしくは置換されたC5〜C8−シクロアルキレン、非置換もしくは置換されたC5〜C8−シクロアルキレン−C1〜C4−アルキレン−C5〜C8−シクロアルキレン、非置換もしくは置換されたヘテロシクロアルキレンおよび非置換もしくは置換されたヘテロシクロアルキレン−C1〜C4−アルキレン−ヘテロシクロアルキレンから選択される]の少なくとも1種の化合物とを含む組成物を提供する。
xは、1、2または3であり、
R1およびR2は、互いに独立して、水素、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択され、
Zは、C3〜C10−アルカンジイル、非置換もしくは置換されたアリーレン、非置換もしくは置換されたアリーレン−C1〜C4−アルキレン−アリーレン、非置換もしくは置換されたヘテロアリーレン、非置換もしくは置換されたヘテロアリーレン−C1〜C4−アルキレン−ヘテロアリーレン、非置換もしくは置換されたC5〜C8−シクロアルキレン、非置換もしくは置換されたC5〜C8−シクロアルキレン−C1〜C4−アルキレン−C5〜C8−シクロアルキレン、非置換もしくは置換されたヘテロシクロアルキレンおよび非置換もしくは置換されたヘテロシクロアルキレン−C1〜C4−アルキレン−ヘテロシクロアルキレンから選択される]の新規化合物(但し、R1およびR2が同一であり、かつ水素、t−ブチル、2−エチルヘキシル、1−エチルペンチル、シクロヘキシルもしくはフェニルであり、かつxが1である場合に、Zが1,4−シクロヘキシレンである化合物またはR1およびR2が両者とも(R)−1−フェニルエチルであり、かつxが1である場合に、Zが−(CH2)9−である化合物を除く)に関する。
− ヘイズ値は、式Iの化合物を含まない参照ポリマー組成物と比較して、ASTM D 1003による方法(層厚1.1mm)で測定して、少なくとも5%だけ低減される。
− 透明度値は、式Iの化合物を含まない参照ポリマー組成物と比較して、ASTM D 1003による方法(層厚1.1mm)で測定して、少なくとも5%だけ高められる。
− レーザ透過率値は、式Iの化合物を含まない参照ポリマー組成物と比較して、1064nm(層厚)で測定して、少なくとも1%だけ高められる。
xは、1、2または3であり、
R1およびR2は、互いに独立して、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択され、かつ
Zは、C3〜C10−アルカンジイル、非置換もしくは置換されたアリーレン、非置換もしくは置換されたアリーレン−C1〜C4−アルキレン−アリーレン、非置換もしくは置換されたヘテロアリーレン、非置換もしくは置換されたヘテロアリーレン−C1〜C4−アルキレン−ヘテロアリーレン、非置換もしくは置換されたC5〜C8−シクロアルキレン、非置換もしくは置換されたC5〜C8−シクロアルキレン−C1〜C4−アルキレン−C5〜C8−シクロアルキレン、非置換もしくは置換されたヘテロシクロアルキレンおよび非置換もしくは置換されたヘテロシクロアルキレン−C1〜C4−アルキレン−ヘテロシクロアルキレンから選択される。
xは、1、2または3、好ましくは1または2、特に1である;
R1およびR2は、互いに独立して、水素、分枝鎖状のC3〜C10−アルキル、C5〜C12−シクロアルキル、C5〜C12−シクロアルキル、C5〜C12−シクロアルキル−C1〜C4−アルキル、アリールおよびアリール−C1〜C4−アルキルから選択され、その際、最後に挙げた4つの基におけるそれぞれの環は、非置換であるか、または1つ以上の同一もしくは異なる基Raによって置換されており、その際、Raは、C1〜C10−アルキルおよびハロゲンから選択される。より好ましくは、R1およびR2は、互いに独立して、水素、分枝鎖状のC3〜C10−アルキル、C5〜C12−シクロアルキル、C5〜C12−シクロアルキル、C5〜C12−シクロアルキル−C1〜C4−アルキル、フェニルおよびフェニル−C1〜C4−アルキルから選択され、その際、最後に挙げた4つの基におけるそれぞれの環は、非置換であるか、または1つ以上の同一もしくは異なる基Raによって置換されており、その際、Raは、C1〜C10−アルキルおよびハロゲンから選択される。特に、R1およびR2は、互いに独立して、水素、分枝鎖状のC3〜C10−アルキルであって、該骨格にアルキル基の第二級もしくは第三級の炭素原子を介して結合されているもの、非置換または1もしくは2個の基Raによって置換されたC5〜C10−シクロアルキルおよび非置換または1もしくは2個の基Raによって置換されたフェニルから選択される。R1およびR2のために適した例は、水素、エチル、n−プロピル、イソプロピル、n−ブチル、t−ブチル、1−メチルプロピル、1−エチルプロピル、1,1−ジメチルプロピル、2−メチルブチル、1,5−ジメチルヘキシル、1,1,3,3−テトラメチルブチル、1−アダマンチル、2−アダマンチル、ホモアダマンチル、シクロペンチル、シクロヘキシル、シクロペンチルメチル、1−シクロペンチルエチル、2−シクロペンチルエチル、シクロヘキシルメチル、1−シクロヘキシルエチル、2−シクロヘキシルエチル、シクロペンチルの1もしくは2個のC1〜C4−アルキルで置換されたもの、シクロヘキシルの1もしくは2個のC1〜C4−アルキルで置換されたもの、フェニル、トリルまたは3,4−ジメチルフェニルである。特に、R1およびR2は、水素、イソプロピル、t−ブチル、1−メチルプロピル、1−エチルプロピル、1,1−ジメチルプロピル、2−メチルブチル、1,5−ジメチルヘキシル、1,1,3,3−テトラメチルブチルおよび1−アダマンチルから選択される。
特にZは、トランス−1,4−シクロヘキサンジイルである。特に、xが2である場合に、それぞれのZは、同じ意味を有する。
R1およびR2は、同じ意味を有し、かつ1,1−ジメチルプロピル、1,5−ジメチルヘキシル、1,1,3,3−テトラメチルブチルおよび1−アダマンチルから選択される;
Zは、トランス−1,4−シクロヘキサンジイルである;かつ
xは、1である。
着色剤という用語は、染料および顔料を含む。顔料は、当該技術分野で公知の有機顔料もしくは無機顔料であってよい。好適な顔料の例は、有色顔料、真珠光沢顔料、例えばエフェクト顔料または液晶ポリマーをベースとする顔料である。
2.1. アルキル化モノフェノール、例えば2,6−ジ−t−ブチル−4−メチルフェノール、2−t−ブチル−4,6−ジメチルフェノール、2,6−ジ−t−ブチル−4−エチルフェノール、2,6−ジ−t−ブチル−4−n−ブチルフェノール、2,6−ジ−t−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−t−ブチル−4−メトキシメチルフェノール、直鎖状または側鎖で分岐したノニルフェノール、例えば2,6−ジ−ノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルトリデカ−1’−イル)フェノールおよびそれらの混合物。
3.1. 2−(2’−ヒドロキシフェニル)ベンゾトリアゾール、例えば2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−t−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(5’−t−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1,1,3,3−テトラメチルブチル)フェニル)ベンゾトリアゾール、2−(3’,5’−ジ−t−ブチル−2’−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(3’−s−ブチル−5’−t−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクチルオキシフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−t−アミル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’,5’−ビス(α,α−ジメチルベンジル)−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−t−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−t−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−ドデシル−2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(3’−t−ブチル−2’−ヒドロキシ−5’−(2−イソオクチルオキシカルボニルエチル)フェニルベンゾトリアゾール、2’−メチレンビス[4−(1,1,3,3−テトラメチルブチル)−6−ベンゾトリアゾール−2−イルフェノール]、2−[3’−t−ブチル−5’−(2−メトキシカルボニルエチル)−2’−ヒドロキシフェニル]−2H−ベンゾトリアゾールとポリエチレングリコール300とのエステル交換反応生成物;[R−CH2CH2−COO−CH2CH2]2であって式中Rが3’−t−ブチル−4’−ヒドロキシ−5’−2H−ベンゾトリアゾール−2−イル−フェニル、2−[2’−ヒドロキシ−3’−(α,α−ジメチルベンジル)−5’−(1,1,3,3−テトラメチルブチル)フェニル]ベンゾトリアゾールであるもの;2−[2’−ヒドロキシ−3’−(1,1,3,3−テトラメチルブチル)−5’−(α,α−ジメチルベンジル)フェニル]ベンゾトリアゾール。
含リン酸は、リンのオキソ酸、例えばリン酸、ホスホン酸およびホスフィン酸を含む。含リン酸の好適な塩は、アルカリ金属塩、アルカリ土類金属塩または遷移金属塩である。なかでも、カルシウム塩、バリウム塩、マグネシウム塩、ナトリウム塩、カリウム塩、マンガン塩およびアルミニウム塩が好ましい。特に好ましいのは、ホスフィン酸ナトリウム(NaPO2H2、次亜リン酸ナトリウムとも知られる)、ビスホスフィン酸マンガン(Mn(H2PO2)2、次亜リン酸マンガン(II)としても知られる)、ホスフィン酸アルミニウム(Al(H2PO2)3)ならびにそれらの混合物である。また、特に好ましいのは、ホスホン酸エステル、半エステルおよびそれらの混合物、特にヒドロキシフェニルアルキルホスホン酸エステル、半エステルまたはそれらの混合物、例えばWO2007006647に開示されるもの、特にカルシウム ビス[モノエチル(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ホスホネート](Irgamod(登録商標)195、BASF SEから市販されている)またはジエチル(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ホスホネート(Irgamod(登録商標)295、BASF SEから市販されている)である。
xは、1、2または3であり、
R1およびR2は、互いに独立して、水素、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択され、
Zは、C3〜C10−アルカンジイル、非置換もしくは置換されたアリーレン、非置換もしくは置換されたアリーレン−C1〜C4−アルキレン−アリーレン、非置換もしくは置換されたヘテロアリーレン、非置換もしくは置換されたヘテロアリーレン−C1〜C4−アルキレン−ヘテロアリーレン、非置換もしくは置換されたC5〜C8−シクロアルキレン、非置換もしくは置換されたC5〜C8−シクロアルキレン−C1〜C4−アルキレン−C5〜C8−シクロアルキレン、非置換もしくは置換されたヘテロシクロアルキレンおよび非置換もしくは置換されたヘテロシクロアルキレン−C1〜C4−アルキレン−ヘテロシクロアルキレンから選択される]の化合物(但し、R1およびR2が同一であり、かつ水素、t−ブチル、2−エチルヘキシル、1−エチルペンチル、シクロヘキシルもしくはフェニルであり、かつxが1である場合に、Zが1,4−シクロヘキシレンである化合物またはR1およびR2が両者とも(R)−1−フェニルエチルであり、かつxが1である場合に、Zが−(CH2)9−である化合物を除く)に関する。
xは、1、2または3であり、
R1およびR2は、互いに独立して、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択され、
Zは、C3〜C10−アルカンジイル、非置換もしくは置換されたアリーレン、非置換もしくは置換されたアリーレン−C1〜C4−アルキレン−アリーレン、非置換もしくは置換されたヘテロアリーレン、非置換もしくは置換されたヘテロアリーレン−C1〜C4−アルキレン−ヘテロアリーレン、非置換もしくは置換されたC5〜C8−シクロアルキレン、非置換もしくは置換されたC5〜C8−シクロアルキレン−C1〜C4−アルキレン−C5〜C8−シクロアルキレン、非置換もしくは置換されたヘテロシクロアルキレンおよび非置換もしくは置換されたヘテロシクロアルキレン−C1〜C4−アルキレン−ヘテロシクロアルキレンから選択される。
I.1 式Iで示され、式中、x=1およびR1=R2である化合物
例1: 1,1’−(トランス−1,4−シクロヘキシレン)ビス(3−(t−ブチル)ウレア)
t−ブチルイソシアネート(3.90g、0.039モル)を無水テトラヒドロフラン(THF)(50mL)中に溶かした溶液を、トランス−1,4−ジアミノシクロヘキサン(2.10g、0.019モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をN,N−ジメチルホルムアミド(DMF)から再結晶化させ、高真空下で乾燥させた。
MS(70eV): 312(M+)
シクロヘキシルイソシアネート(5.49g、0.044モル)を無水THF(50mL)中に溶かした溶液を、トランス−1,4−ジアミノシクロヘキサン(2.51g、0.022モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をDMFから再結晶化させ、高真空下で乾燥させた。
MS(70eV): 364(M+)
イソプロピルアミン(1.25g、0.022モル)を無水THF(50mL)中に溶かした溶液を、トランス−1,4−シクロヘキサンジイソシアネート(1.75g、0.011モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をDMFから再結晶化させ、高真空下で乾燥させた。
MS(70eV): 284(M+)
3−アミノペンタン(2.20g、0.025モル)を無水THF(50mL)中に溶かした溶液を、トランス−1,4−シクロヘキサンジイソシアネート(2.00g、0.012モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をDMFから再結晶化させ、高真空下で乾燥させた。
MS(70eV): 340(M+)
イソシアナトシクロヘキサン(3.25g、0.026モル)を無水THF(50mL)中に溶かした溶液を、シス−1,4−シクロヘキサンジアミン(1.50g、0.013モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をMeOHから再結晶化させ、高真空下で乾燥させた。
融点: 252℃
MS(70eV): 364(M+)
t−ブチルイソシアネート(2.57g、0.026モル)を無水THF(50mL)中に溶かした溶液を、シス−1,4−シクロヘキサンジアミン(1.50g、0.013モル)を無水THF(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる無水THFで洗浄した。得られた白色の固体をMeOHから再結晶化させ、高真空下で乾燥させた。
融点: 319℃
MS(70eV): 312(M+)
MS(70eV): 340(M+)
MS(70eV): 426(M+)
MS(70eV): 425(M+)
MS(70eV): 468(M+)
融点: 358℃
MS(70eV): 312(M+)
MS(70eV): 284(M+)
MS(70eV): 256(M+)
トランス−1,4−ジアミノシクロヘキサン(2.10g、0.019モル)を水(40mL)中に溶解させた。該溶液を、HClの添加によりpH5〜7にした。3.30gのシアン酸カリウムを撹拌しながらゆっくりと添加した。得られた混合物を加熱還流させ、24時間にわたり撹拌した。沈殿物を濾過し、更なる水で洗浄した。得られた白色の固体を高真空下で乾燥させた。
例15: 1−t−ブチル−3−[4−(シクロヘキシルカルバモイルアミノ)シクロヘキシル]尿素
15.1 トランス−1−(4−アミノシクロヘキシル)−3−シクロヘキシルウレア
トランス−1,4−ジアミノシクロヘキサン(6.15g、0.054モル)を無水THF(500mL)中に溶かした溶液を、冷却浴(イソプロピルアルコール/ドライアイス)中で不活性雰囲気下で−40℃に冷却した。イソシアナトシクロヘキサン(6.75g、0.054モル)を無水THF(100mL)中に入れたものを激しく撹拌しながらゆっくりと添加した。得られた混合物を、室温で更に24時間にわたり撹拌した。沈殿する白色固体を濾過し、水中に懸濁し、そしてpH2へと酸性化(HCl)させた。生じた澄明な溶液を再び濾過し、そして濾液をpH8にし(NaOH)、その後に、トランス−1−(4−アミノシクロヘキシル)−3−シクロヘキシルウレアが白色固体として沈殿した。
t−ブチルイソシアネート(1.17g、0.012モル)を無水N−メチル−2−ピロリドン(NMP)(50mL)中に溶かした溶液を、トランス−1−(4−アミノシクロヘキシル)−3−シクロヘキシルウレア(2.83g、0.012モル)を無水NMP(100mL)中に溶かした溶液へと不活性雰囲気下でゆっくりと添加した。得られた混合物を70℃に加熱し、24時間にわたり撹拌した。該溶液を1MのHCl中で沈殿させ、濾別した。得られた白色の固体をTHFで洗浄し、DMFから再結晶化させ、高真空下で乾燥させた。
融点: 325℃
MS(70eV): 338(M+)
トランス−1,4−ジアミノシクロヘキサン(6.15g、0.054ミリモル)を、火炎乾燥されたシュレンクフラスコ中に添加し、THF(500mL)中にアルゴン雰囲気下で溶解させた。該溶液を、冷却浴(イソプロピルアルコール/ドライアイス)中で−40℃に冷却し、そしてシクロヘキシルイソシアネート(6.75g、0.054ミリモル)をTHF(100mL)中に希釈したものを、激しく撹拌しながらゆっくりと添加した。その反応混合物を、室温で12時間にわたり撹拌した。沈殿した白色固体を濾別し、水中に懸濁し、そしてpH2へと酸性化(HCl)させた。生じた澄明な溶液を再び濾過し、そして濾液をpH8にし(NaOH)、その後に、トランス−1−(4−アミノシクロヘキシル)−3−シクロヘキシルウレアが白色固体として沈殿した。
MS(70eV): 265(M+)
粉体化されたポリアミドと式Iの尿素化合物を、ガラス瓶中で1.0質量%の濃度で正確に秤量した。該組成物を次いで、40〜45rpmで24時間にわたり回転混合して配合した。上述の粉体を次いで同時回転二軸スクリュー型コンパウンダ(DSM Xplore)において50rpmの回転速度で250℃の溶融温度で窒素下に5分間にわたりコンパウンディングした。種々の濃度を、引き続き初期成核剤濃度をストレートのポリアミドで希釈することによって調製した。ストレートのポリアミドを同様に処理することで、ブランク対照サンプルを作製した。
− Ultramid(登録商標)B27、BASF SE(ドイツ)から入手可能:PA6グレード
− Ultramid(登録商標)A27E1、BASF SE(ドイツ)から入手可能:PA66グレード
− PA66/6(90/10)
− Ultramid(登録商標)C33、BASF SE(ドイツ)から入手可能:PA6/66グレード
− Zytel(登録商標)1512、DuPontから入手可能、PA6/12グレード
− Ultramid(登録商標)S3K Balance、BASF SE(ドイツ)から入手可能:PA6,10グレード。
射出成形は、DSM Xploreの12ml射出成形機で実施した。約8.5gの溶融されたコンパウンドを直接的にバレル中に250℃で二軸スクリュー押出機から窒素で覆いながら充填した。溶融物を、研磨した成形型中に約6バールの圧力で射出した。成形型温度は100℃であった。回収された試験片は25mmの直径を有していた。
様々な混合物および対照サンプルの結晶化挙動を、Perkin Elmer Diamond DSCで示差走査熱量測定(DSC)によって窒素下で測定した。50℃と250℃の間での2つの加熱および冷却走査を10℃/分の標準速度で行った。熱的履歴を消すために、各冷却作業前にサンプルを250℃で5分間にわたり保持した。ポリマー結晶化についての値(Tc)は、2番目の冷却走査の発熱最小値で測定した。
ヘイズと透明度は、haze-guard plus機器(BYK、Gardner(登録商標)、照明CIE-E)を用いて室温で測定した。前記のhaze-guard plus機器は、ASTM D-1003に準拠している。ヘイズ値と透明度値は、射出成形から試験片を得てから12時間〜24時間の間に測定した。測定されたサンプルは、25mmの直径を有していた。
レーザ透過度は、波長1064nmで熱電能測定によって測定した。測定ジオメトリは、以下の通り設置した:ビーム分割器(Laseroptik GmbH社製のSQ2非分極ビーム分割器)を使用して、1ワットの出力の参照ビームを、90゜の角度で、2ワットの全出力を有するレーザビーム(波長1064nmを有するダイオードポンプ型Nd−YAGレーザ、FOBA DP50)から分割した。参照ビームを参照センサに当てた。本来のビームの前記ビーム分割器を通過した部分は、同様に1ワットの出力を有する測定ビームを提供する。このビームを0.18μmの焦点直径へと、ビーム分割器の後方にあるモード絞り(5.0)を介して合焦した。レーザ透過率(LT)測定センサは、焦点の80mm下方に配置した。試験シートは、LT測定センサの2mm上方に配置した。射出成形した試験シートを使用した。その試験シートは、60×60×2mm3の寸法とエッジゲートを有している。測定は、シート中央(2つの対角線の交点)で行った。射出成形パラメータを以下の値に定めた:
LT=(信号(測定センサ)/信号(参照センサ))×100%
ポリアミド組成物の結晶化温度(Tc)、ヘイズおよび透明度ならびに試験片(プレート)の厚さおよび本発明による式Iの化合物の濃度を、以下の表I〜XVIに列挙する。
** Ceasit AV, 粉状流動助剤、Baerlocher社製
IC 本発明による組成物
CC 比較組成物
Claims (17)
- 請求項1に記載の組成物であって、R1およびR2は、互いに独立して、直鎖状のC1〜C7−アルキル、分枝鎖状のC3〜C10−アルキル、非置換もしくは置換されたC3〜C12−シクロアルキル、非置換もしくは置換されたC3〜C12−シクロアルキル−C1〜C4−アルキル、非置換もしくは置換されたアリールおよび非置換もしくは置換されたアリール−C1〜C4−アルキルから選択される前記組成物。
- 請求項1に記載の組成物であって、R1およびR2は、互いに独立して、水素、分枝鎖状のC3〜C10−アルキル、C5〜C12−シクロアルキル、C5〜C12−シクロアルキル−C1〜C4−アルキル、フェニルおよびフェニル−C1〜C4−アルキルから選択され、その際、最後に挙げた4つの基におけるそれぞれの環は、非置換であるか、または1つ以上の同一もしくは異なる基Raによって置換されており、その際、Raは、C1〜C10−アルキルまたはハロゲンから選択される前記組成物。
- 請求項1に記載の組成物であって、R1およびR2は、互いに独立して、分枝鎖状のC3〜C10−アルキルであって骨格にアルキル基の第二級もしくは第三級の炭素原子を介して結合されている前記分枝鎖状のC3〜C10−アルキル、非置換または1もしくは2個の基Raによって置換されたC5〜C10−シクロアルキルおよび非置換または1もしくは2個の基Raによって置換されたフェニルから選択される前記組成物。
- 請求項1から4までのいずれか1項に記載の組成物であって、R1およびR2が同じ意味を有する前記組成物。
- 請求項1から5までのいずれか1項に記載の組成物であって、xが1である前記組成物。
- 請求項1から6までのいずれか1項に記載の組成物であって、R1およびR2は、同一であり、かつ水素、t−ブチル、1,1−ジメチルプロピル、1,5−ジメチルヘキシル、1,1,3,3−テトラメチルブチルおよび1−アダマンチルから選択され、かつxは1である前記組成物。
- 請求項1から7までのいずれか1項に記載の組成物であって、前記ポリアミドポリマーは、脂肪族ポリアミドホモポリマー、脂肪族ポリアミドコポリマーおよび部分芳香族ポリアミドから選択される前記組成物。
- 請求項1から8までのいずれか1項に記載の組成物であって、前記ポリアミドポリマーは、PA6、PA7、PA10、PA11、PA12、PA66、PA69、PA610、PA612、PA1010、PA6/66、PA66/6、PA66/610およびそれらの混合物から選択される前記組成物。
- 請求項1から9までのいずれか1項に記載の組成物であって、前記ポリアミドポリマーは、PA6、PA11、PA12、PA66、PA66/6およびPA6/66から選択され、かつ式(I)の化合物において、R1およびR2が、同一であり、かつ水素、t−ブチル、1,1−ジメチルプロピル、1,5−ジメチルヘキシル、1,1,3,3−テトラメチルブチルおよび1−アダマンチルから選択され、かつxが1である前記組成物。
- 請求項1から10までのいずれか1項に記載の組成物であって、式(I)の化合物は、前記ポリアミドポリマーの質量に対して、0.001〜5質量%の量で存在する前記組成物。
- 請求項1から10までのいずれか1項に記載の組成物であって、式(I)の化合物は、前記ポリアミドポリマーの質量に対して、0.01〜3質量%の量で存在する前記組成物。
- 請求項1から10までのいずれか1項に記載の組成物であって、式(I)の化合物は、前記ポリアミドポリマーの質量に対して、0.05〜2質量%の量で存在する前記組成物。
- 請求項1から13までのいずれか1項に記載の組成物であって、前記ポリマー組成物は、更に、着色剤、酸化防止剤、UV吸収剤、光安定剤、強化材、充填剤、防曇剤、離型剤、殺生物剤、帯電防止剤およびレオロジー調節剤から選択された少なくとも1種の更なる添加剤を含む前記組成物。
- 請求項1から14までのいずれか1項に記載のポリマー組成物を含む成形品。
- 請求項16に記載の成形品であって、フィルム、繊維、シート、パイプ、半完成品、造粒物、コンテナ、ブロー成形品またはモノフィラメントから選択される前記成形品。
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PCT/EP2013/055718 WO2013139802A1 (en) | 2012-03-20 | 2013-03-19 | Polyamide compositions with improved optical properties |
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WO2016166140A1 (de) | 2015-04-16 | 2016-10-20 | Basf Se | Polyamide mit besseren optischen eigenschaften |
EP3118247A1 (de) * | 2015-07-15 | 2017-01-18 | Basf Se | Polyamide mit besseren optischen eigenschaften |
BR112020007184A2 (pt) | 2017-11-23 | 2020-09-24 | Basf Se | composição de poliamida, processo de produção de composições, uso de composição, molde soldável, uso de álcoois póli-hídricos e processo de aumento da resistência de costura |
KR20200093069A (ko) * | 2017-12-18 | 2020-08-04 | 바스프 에스이 | 개선된 광학 특성을 갖는 폴리아미드 성형 조성물 및 그 조성물에서의 착색제의 용도 |
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CA2867924A1 (en) | 2013-09-26 |
RU2014141921A (ru) | 2016-05-10 |
BR112014022977B1 (pt) | 2020-12-29 |
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EP2828329A1 (en) | 2015-01-28 |
IL234427A (en) | 2016-09-29 |
KR20140144702A (ko) | 2014-12-19 |
CA2867924C (en) | 2020-07-21 |
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CN104271654B (zh) | 2016-10-19 |
EP2828329B1 (en) | 2015-12-30 |
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ZA201407505B (en) | 2016-06-29 |
AU2013237496A1 (en) | 2014-10-09 |
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PH12014502108B1 (en) | 2014-12-10 |
WO2013139802A1 (en) | 2013-09-26 |
AU2013237496B2 (en) | 2016-02-25 |
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