CN103554650A - 含有山梨糖醇化合物的透明化剂组合物以及聚丙烯系树脂组合物的制造方法 - Google Patents
含有山梨糖醇化合物的透明化剂组合物以及聚丙烯系树脂组合物的制造方法 Download PDFInfo
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- CN103554650A CN103554650A CN201310375854.3A CN201310375854A CN103554650A CN 103554650 A CN103554650 A CN 103554650A CN 201310375854 A CN201310375854 A CN 201310375854A CN 103554650 A CN103554650 A CN 103554650A
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- Prior art keywords
- polypropylene
- butyl
- based resin
- dibenzylidene sorbitol
- tert
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- -1 sorbitol compound Chemical class 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000011342 resin composition Substances 0.000 title claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 title abstract description 42
- 229920001155 polypropylene Polymers 0.000 title abstract description 8
- 239000004743 Polypropylene Substances 0.000 title abstract description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 title description 10
- 239000000600 sorbitol Substances 0.000 title description 10
- 229940087101 dibenzylidene sorbitol Drugs 0.000 claims abstract description 45
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 239000002245 particle Substances 0.000 claims abstract description 29
- 238000001125 extrusion Methods 0.000 claims abstract description 12
- 229920005673 polypropylene based resin Polymers 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 5
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 abstract description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
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- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 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
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/156—Heterocyclic compounds having oxygen in the ring having two oxygen atoms in the ring
- C08K5/1575—Six-membered 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
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/022—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the choice of material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/04—Particle-shaped
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
- B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
- B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/92—Measuring, controlling or regulating
-
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Abstract
本发明涉及一种透明化剂组合物，其是包含100质量份的具有d97为30μm～200μm的粒径的下述通式（I）表示的二亚苄基山梨糖醇化合物与5～200质量份的四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷的混合物，并且这两种成分的总量为混合物的50质量%以上。另外，本发明还涉及一种聚丙烯系树脂组合物的制造方法，其特征在于，在获得聚丙烯系树脂中配合有具有d97为30μm～200μm的粒径的下述通式（I）表示的二亚苄基山梨糖醇化合物的聚丙烯系树脂组合物时，将在100质量份的所述聚丙烯系树脂中配合了0.05～2质量份的所述二亚苄基山梨糖醇化合物而得到的混合物，使用双螺杆挤出机在220～250℃的挤出温度下进行混炼。
Description
本申请是申请日为2011年3月8日、中国申请号为201180004943.6的专利申请的分案申请。
技术领域
本发明涉及一种透明化剂树脂组合物，其通过将以往认为不适合在聚丙烯系树脂的加工时添加的粒径较大的二亚苄基山梨糖醇系透明化剂在与树脂进行混合之前，预先与特定的酚系抗氧化剂混合，然后将该混合物添加于树脂中，由此可以形成透明性优良的聚丙烯系树脂组合物。
另外，本发明还涉及一种透明性优良的聚丙烯系树脂组合物的制造方法，在该方法中，通过选择特定的加工条件，就能够配合以往认为不适合在聚丙烯系树脂的加工时添加的粒径较大的二亚苄基山梨糖醇系透明化剂。
背景技术
丙烯均聚物或乙烯-丙烯共聚物等聚丙烯系树脂被广泛用于汽车、家电、建筑材料、家具、包装容器、玩具、日用杂货等。但是，聚丙烯系树脂在透明性方面不如聚乙烯、聚对苯二甲酸乙二醇酯、聚碳酸酯、聚苯乙烯等，所以以往提出了配合苯甲酸金属盐、芳香族磷酸酯金属盐、脂肪族环状化合物的金属盐以及二亚苄基山梨糖醇类、酰胺化合物等各种成核剂、透明化剂的技术，并得到了实用化。
其中，二亚苄基山梨糖醇类尽管透明性的改良效果优良，但存在着臭味强，熔点高，加工温度下在树脂中的均匀分散困难等缺点。通过将加工温度设定为熔点以上就能够实现均匀分散，但本发明中使用的通式（I）表示的化合物的熔点高达260℃以上，熔点以上的温度下的加工会引起聚丙烯的显著劣化，因而不优选。为了提高熔点以下的温度下的在树脂中的分散性，提出了通过粉碎而减小粒径，或预先与其它成分熔融混合而使熔点下降等各种处理方法。
例如，在专利文献1中，提出了通过将二亚苄基山梨糖醇类制成d97为 30μm以下的粉末而使其表现出性能的方案。该二亚苄基山梨糖醇类尽管透明性的改良效果优良，但制成微粉时，流动性下降，因此计量、投料等操作性下降，此外，还存在着因粘连（blocking）而无法获得所期望的分散性等问题。另外，微粉碎后的产物实际上需要用无机物或表面处理剂等防止二次凝聚，制造成本增加，而且树脂中还会混入不需要的成分。不需要的成分的混入会引起不想要的树脂物性的变化，或者成为再利用时的品质下降或用途限定的原因，因此微粉化未必能是令人满意的解决方法。
在专利文献2中，提出了通过使用不同结构的二亚苄基山梨糖醇化合物的混合物来提高性能的技术。通过形成类似结构物的混合物而能够使熔点下降，所以在树脂中的分散性提高。但是，上述提案是在二亚苄基山梨糖醇类中的效果特别优良的化合物中勉强添加其它结构的透明化剂，所以因透明化效果下降等而未成为充分的解决方案。
另外，聚丙烯如果是单独的话，在加工温度下会劣化，所以配合酚系抗氧化剂或磷系抗氧化剂等添加剂成分是不可缺少的，这些添加剂成分与成核剂和透明化剂一起配合于聚丙烯的粉末或颗粒中的技术是以往一直实行的。如专利文献1中的比较例所记载的，即使将上述的其它添加剂成分与二亚苄基山梨糖醇类一起配合于树脂中，并利用亨舍尔混合机等混合，也不能提高二亚苄基山梨糖醇类的分散性。
现有技术文献
专利文献
专利文献1：日本特开平06-145431号公报
专利文献2：日本特开平02-206627号公报
发明内容
本发明要解决的问题
本发明的目的是通过不将二亚苄基山梨糖醇化合物微粉化而配合于聚丙烯系树脂中，提供一种可以形成透明性优良的聚丙烯系树脂组合物的二亚苄基山梨糖醇系透明化剂。
另外，本发明的目的是提供一种尽管二亚苄基山梨糖醇化合物不进行微粉化就配合于聚丙烯系树脂中，但仍然具有优良的透明性和物性的聚丙烯系树脂组合物的制造方法。
解决问题的手段
本发明通过提供下述的透明化剂组合物而实现了上述目的，所述透明化剂组合物是包含100质量份的具有d97为30μm～200μm的粒径的下述通式（I）表示的二亚苄基山梨糖醇化合物与5～200质量份的四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷的混合物，并且这两种成分的总量为混合物的50质量%以上。
另外，本发明通过提供下述的聚丙烯系树脂组合物的制造方法而实现了上述目的，所述制造方法的特征在于，在获得聚丙烯系树脂中配合有具有d97为30μm～200μm的粒径的下述通式（I）表示的二亚苄基山梨糖醇化合物的聚丙烯系树脂组合物时，将在所述聚丙烯系树脂100质量份中配合了0.05～2质量份的所述二亚苄基山梨糖醇化合物而得到的混合物，使用双螺杆挤出机在220～250℃的挤出温度下进行混炼。
具体实施方式
首先对本发明的透明化剂组合物进行说明。本发明的透明化剂组合物中使用的通式（I）表示的二亚苄基山梨糖醇化合物的制造方法没有特别限定，可以是用公知的任一种方法制造的。
本发明的透明化剂组合物中使用的通式（I）表示的二亚苄基山梨糖醇化合物的粒径是，d97为30μm～200μm，d97优选为40μm～150μm，d97特别优选为40μm～100μm。如果粉碎至d97低于30μm，则粉碎成本变高，而且会发生粘连而使操作性下降，在树脂中的分散性也下降，因而不优选。d97如果大于200μm，则透明性不充分，在成型为膜等时存在鱼眼增加等问题。此外，本发明中的d97，是指小于某一粒径的粒子量相对于总粒子量的百分比为97的粒径。
对于本发明的透明化剂组合物中使用的四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷以及包括其中间体在内，可以不受其制造方法、晶体形态、熔点、红外线吸收光谱、X射线衍射峰等限定地进行使用。
本发明的透明化剂组合物是在100质量份的通式（I）表示的二亚苄基山梨糖醇化合物中混合四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷5～200质量份、优选为10～150质量份而得到的，并且混合装置以及温度等混合条件等没有特别限制，可以使用亨舍尔混合机等各种混合装置。特别是由于不需要使其熔融，所以优选不进行加热或冷却等会导致成本增加的处理，而在室温下进行混合。另外，只要在室温下混合，则混合时不必担心会着色，因而是优选的。另外，为了抑制与树脂的加热混炼时的氧化引起的着色，还可以在氮气气氛下进行混合处理。
本发明的透明化剂组合物中，通式（I）表示的二亚苄基山梨糖醇化合物和四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷这两种成分的总量为混合物的50质量%以上，优选为80质量%以上，特别优选为100质量%。
作为本发明的透明化剂组合物中可以配合的除了上述两种成分以外的成分，可以列举出抗氧化剂、受阻胺化合物、其它的成核剂等。
本发明的透明化剂组合物对于聚丙烯系树脂的透明性提高是有效的，作为聚丙烯系树脂，可以列举出聚丙烯均聚物、乙烯-丙烯无规共聚物、乙烯-丙烯嵌段共聚物、丙烯与少量（1～10质量%）的其它α-烯烃（例如1-丁烯、1-己烯、4-甲基-1-戊烯等）形成的共聚物、丙烯与乙丙烯形成的共聚物（TPO）等。
上述的聚丙烯系树脂可以不考虑聚合催化剂/助催化剂的种类或有无、有规立构性、平均分子量、分子量分布、特定的分子量成分的有无或比例、比重、粘度、在各种溶剂中的溶解度、伸长率、冲击强度、结晶度、X射线衍射、通过不饱和羧酸（马来酸、衣康酸、富马酸等）以及其衍生物（马来酸酐、马来酸单酯、马来酸二酯等）或有机过氧化物或者能量射线的照射以及这些处理的组合进行的改性/交联处理的有无等来使用。
本发明的透明化剂组合物相对于100质量份的聚丙烯系树脂，优选配合0.01～10质量份，更优选配合0.05～5质量份。
在配合有本发明的透明化剂组合物的聚丙烯系树脂组合物中，优选根据使用条件以及要求特性添加酚系抗氧化剂、磷系抗氧化剂、硫系抗氧化剂、紫外线吸收剂、受阻胺化合物、阻燃剂、阻燃助剂、其它的成核剂、抗静电剂、重金属惰性化剂、增塑剂、软化剂、润滑剂、水滑石化合物、脂肪酸金 属盐、颜料、红外线吸收剂、防灰雾（antifogging）剂、防雾（antimist）剂、填充剂、抗菌/抗霉剂等通用的树脂添加剂。
作为酚系抗氧化剂，可以列举出2,6-二叔丁基-对甲酚、2,6-二苯基-4-十八烷氧基苯酚、2-甲基-4,6-双（辛硫基甲基）苯酚、二硬脂酰基（3,5-二叔丁基-4-羟基苄基）膦酸酯、1,6-六亚甲基双[（3,5-二叔丁基-4-羟基苯基）丙酸酰胺]、4,4’-硫代双（6-叔丁基-间甲酚）、2,2’-亚甲基双（4-甲基-6-叔丁基苯酚）、2,2’-亚甲基双（4-乙基-6-叔丁基苯酚）、4,4’-亚丁基双（6-叔丁基-间甲酚）、2,2’-亚乙基双（4,6-二叔丁基苯酚）、2,2’-亚乙基双（4-仲丁基-6-叔丁基苯酚）、1,1,3-三（2-甲基-4-羟基-5-叔丁基苯基]丁烷、1,3,5-三（2,6-二甲基-3-羟基-4-叔丁基苄基）异氰脲酸酯、1,3,5-三（3,5-二叔丁基-4-羟基苄基）异氰脲酸酯、1,3,5-三（3,5-二叔丁基-4-羟基苄基）-2,4,6-三甲基苯、2-叔丁基-4-甲基-6-（2-丙烯酰氧基-3-叔丁基-5-甲基苄基）苯酚、硬脂酰基（3,5-二叔丁基-4-羟基苯基）丙酸酯、硫代二甘醇双[（3,5-二叔丁基-4-羟基苯基）丙酸酯]、1,6-六亚甲基双[（3,5-二叔丁基-4-羟基苯基）丙酸酯]、双[3,3-双（4-羟基-3-叔丁基苯基）丁酸]二醇酯、双[2-叔丁基-4-甲基-6-（2-羟基-3-叔丁基-5-甲基苄基）苯基]对苯二甲酸酯、1,3,5-三[（3,5-二叔丁基-4-羟基苯基）丙酰氧基乙基]异氰脲酸酯、四[3-（3,5-二叔丁基-4-羟基苯基）丙酸甲酯]甲烷、3,9-双[1,1-二甲基-2-{（3-叔丁基-4-羟基-5-甲基苯基）丙酰氧基}乙基]-2,4,8,10-四氧杂螺[5,5]十一烷、三甘醇双[（3-叔丁基-4-羟基-5-甲基苯基）丙酸酯]等，相对于树脂100重量份，优选使用0.001～10重量份，更优选使用0.05～5重量份。
作为磷系抗氧化剂，可以列举出例如三壬基苯基亚磷酸酯、三（2,4-二叔丁基苯基）亚磷酸酯、三[2-叔丁基-4-（3-叔丁基-4-羟基-5-甲基苯硫基）-5-甲基苯基]亚磷酸酯、亚磷酸十三烷基酯、辛基二苯基亚磷酸酯、二（癸基）单苯基亚磷酸酯、二（十三烷基）季戊四醇二亚磷酸酯、二（壬基苯基）季戊四醇二亚磷酸酯、双（2,4-二叔丁基苯基）季戊四醇二亚磷酸酯、双（2,6-二叔丁基-4-甲基苯基）季戊四醇二亚磷酸酯、双（2,4,6-三叔丁基苯基）季戊四醇二亚磷酸酯、双（2,4-二枯基苯基）季戊四醇二亚磷酸酯、四（十三烷基）对异丙基联苯酚二亚磷酸酯、四（十三烷基）-4,4’-正亚丁基双（2-叔丁基-5-甲基苯酚）二亚磷酸酯、六（十三烷基）-1,1,3-三（2-甲基-4-羟基-5-叔 丁基苯基）丁烷三亚磷酸酯、四（2,4-二叔丁基苯基）亚联苯基二膦酸酯、9,10-二氢-9-氧代-10-磷杂菲-10-氧化物、2,2’-亚甲基双（4,6-叔丁基苯基）-2-乙基己基亚磷酸酯、2,2’-亚甲基双（4,6-叔丁基苯基）-十八烷基亚磷酸酯、2,2’-亚乙基双（4,6-二叔丁基苯基）-氟代亚磷酸酯、三（2-[（2,4,8,10-四叔丁基二苯并[d,f][1,3,2]二噁磷环庚烷-6-基）氧]乙基）胺、2-乙基-2-丁基丙二醇与2,4,6-三叔丁基苯酚的亚磷酸酯等。
作为硫系抗氧化剂，可以列举出硫代二丙酸二月桂酯、硫代二丙酸二肉豆蔻酯、硫代二丙酸二棕榈酯、硫代二丙酸二硬脂酯、四（3-月桂基硫代二丙酸甲酯）甲烷、双（2-甲基-4-（烷基（C8～C18的单独或混合）硫代丙酰氧基）-5-叔丁基苯基）硫化物、2-巯基苯并咪唑以及其锌盐等。
作为紫外线吸收剂，可以列举出2,4-二羟基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-4-辛氧基二苯甲酮、5,5’-亚甲基双（2-羟基-4-甲氧基二苯甲酮）等2-羟基二苯甲酮类；2-（2’-羟基-5’-甲基苯基）苯并三唑、2-（2’-羟基-3’,5’-二叔丁基苯基）-5-氯苯并三唑、2-（2’-羟基-3’-叔丁基-5’-甲基苯基）-5-氯苯并三唑、2-（2’-羟基-5’-叔辛基苯基）苯并三唑、2-（2’-羟基-3’,5’-二枯基苯基）苯并三唑、2,2’-亚甲基双（4-叔辛基-6-苯并三唑基）苯酚、2-（2’-羟基-3’-叔丁基-5’-羧基苯基）苯并三唑等2-（2’-羟基苯基）苯并三唑类；水杨酸苯酯、间苯二酚单苯甲酸酯、2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、2,4-二叔戊基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、十六烷基-3,5-二叔丁基-4-羟基苯甲酸酯等苯甲酸酯类；2-乙基-2’-乙氧基草酰替苯胺、2-乙氧基-4’-十二烷基草酰替苯胺等取代草酰替苯胺类；乙基-α-氰基-β,β-二苯基丙烯酸酯、甲基-2-氰基-3-甲基-3-（对甲氧基苯基）丙烯酸酯等氰基丙烯酸酯类；2-（2-羟基-4-辛氧基苯基）-4,6-双（2,4-二叔丁基苯基）-s-三嗪、2-（2-羟基-4-甲氧基苯基）-4,6-二苯基-s-三嗪、2-（2-羟基-4-丙氧基-5-甲基苯基）-4,6-双（2,4-二叔丁基苯基）-s-三嗪等三芳基三嗪类。
作为受阻胺化合物，可以列举出例如2,2,6,6-四甲基-4-哌啶基硬脂酸酯、1,2,2,6,6-五甲基-4-哌啶基硬脂酸酯、2,2,6,6-四甲基-4-哌啶基苯甲酸酯、双（2,2,6,6-四甲基-4-哌啶基）癸二酸酯、双（1,2,2,6,6-五甲基-4-哌啶基）癸二酸酯、双（1-十一烷氧基-2,2,6,6-四甲基-4-哌啶基）碳酸酯、四（2,2,6,6-四甲基-4-哌啶基丁烷四羧酸酯、四（1,2,2,6,6-五甲基-4-哌啶基丁烷四羧酸酯、双 （2,2,6,6-四甲基-4-哌啶基）·二（十三烷基）-1,2,3,4-丁烷四羧酸酯、双（1,2,2,6,6-五甲基-4-哌啶基）·二（十三烷基）-1,2,3,4-丁烷四羧酸酯、双（1,2,2,6,6-五甲基-4-哌啶基）-2-丁基-2-（3,5-二叔丁基-4-羟基苄基）丙二酸酯、1-（2-羟基乙基）-2,2,6,6-四甲基-4-哌啶醇/琥珀酸二乙酯缩聚物、1,6-双（2,2,6,6-四甲基-4-哌啶基氨基）己烷/二溴乙烷缩聚物、1,6-双（2,2,6,6-四甲基-4-哌啶基氨基）己烷/2,4-二氯-6-吗啉代-s-三嗪缩聚物、1,6-双（2,2,6,6-四甲基-4-哌啶基氨基）己烷/2,4-二氯-6-叔辛基氨基-s-三嗪缩聚物、1,5,8,12-四[2,4-双（N-丁基-N-（2,2,6,6-四甲基-4-哌啶基）氨基）-s-三嗪-6-基]-1,5,8,12-四氮杂十二烷、1,5,8,12-四[2,4-双（N-丁基-N-（1,2,2,6,6-五甲基-4-哌啶基）氨基）-s-三嗪-6-基]-1,5,8,12-四氮杂十二烷、1,6,11-三[2,4-双（N-丁基-N-（2,2,6,6-四甲基-4-哌啶基）氨基）-s-三嗪-6-基氨基十一烷、1,6,11-三[2,4-双（N-丁基-N-（1,2,2,6,6-五甲基-4-哌啶基）氨基）-s-三嗪-6-基氨基十一烷等受阻胺化合物。
作为阻燃剂，可以使用十溴二苯基醚或四溴双酚A等卤系阻燃剂、磷酸三苯酯、间苯二酚或双酚A等多元酚与苯酚或2,6-二甲苯酚等一元酚的缩合磷酸酯；红磷、磷酸三聚氰胺等无机磷化合物；三聚氰胺异氰脲酸酯等含氮阻燃剂；氢氧化镁或氢氧化铝等无机系阻燃剂；氧化锑或氧化锆等阻燃助剂；聚四氟乙烯等防滴落剂等。
作为阻燃助剂，可以列举出聚四氟乙烯（PTFE）、聚偏氟乙烯（PVDF）、聚氟乙烯（PVF）、聚四氟乙烯-六氟丙烯共聚物（FEP）、（甲基）丙烯酸改性PTFE等氟树脂或硅树脂等。
作为其它的成核剂，可以列举出苯甲酸钠、对叔丁基苯甲酸铝、对叔丁基苯甲酸锂等苯甲酸类的金属盐；2,2-亚甲基双（4,6-二叔丁基苯基）磷酸酯钠等磷酸酯金属盐；二亚苄基山梨糖醇、双（4-甲基亚苄基）山梨糖醇、双（4-乙基亚苄基）山梨糖醇等其它的亚苄基山梨糖醇类；丙三醇锌等金属醇盐类；谷氨酸锌等氨基酸金属盐；二环庚烷二羧酸或其盐等具有二环结构的脂肪族二元酸以及其金属盐、苯磺酸钠、对甲苯磺酸锂等芳香族磺酸金属盐等。
本发明中，即使不将透明性赋予性能特别优良的通式（I）的二亚苄基山梨糖醇化合物进行微粉碎就使用，也能够获得与微粉碎品同样的效果，并且 与其它的二亚苄基山梨糖醇类并用的话，与添加量相比，透明性的提高效果变小，所以本发明的效果下降。通过与2,2-亚甲基双（4,6-二叔丁基苯基）磷酸酯钠等磷酸酯金属盐等金属盐系化合物那样的不仅可提高透明性、还可提高聚丙烯系树脂的玻璃化转变温度的成核剂并用，能够期待仅用本发明无法获得的效果，因而是优选的。
作为重金属惰性化剂，可以列举出例如2-羟基苯并酰胺-N-1H-1,2,4-三唑-3-基、十二烷二酸双[2-（2-羟基苯甲酰基）酰肼]等。
作为水滑石化合物，优选使用下述通式（II）表示的由镁和铝构成的复盐化合物、或者由镁、锌和铝构成的复盐化合物，此外，也可以是将结晶水脱水后的产物。
MgX1ZnX2Al2·(OH)2(X1+X2)+4·(CO3)1-y1/2·mH2O （II）
（式中的x1、x2和y1分别表示满足下式表示的条件的数，m表示0或任意的整数。0≤x2/x1≤10、2≤x1+x2＜20、0≤y1≤2）
上述水滑石化合物可以是天然物，也可以是合成品。作为该合成品的合成方法，可以列举出日本特公昭46-2280号公报、日本特公昭50-30039号公报、日本特公昭51-29129号公报、日本特公平3-36839号公报、日本特开昭61-174270号公报、日本特开2001-164042号公报、日本特开2002-53722号公报等中所记载的公知的合成方法。另外，本发明中，上述水滑石化合物可以不受其晶体结构、晶体粒径等的限制地使用，原料中所含的铁等重金属成分的残存量在精制成本实用的范围内优选较少。
此外，作为上述水滑石化合物，还可以使用将其表面用硬脂酸等高级脂肪酸、油酸碱金属盐等高级脂肪酸金属盐、十二烷基苯磺酸碱金属盐等有机磺酸金属盐、高级脂肪酰胺、高级脂肪酸酯或石蜡等覆盖后的物质。
在聚丙烯系树脂中配合本发明的透明化剂组合物的方法以及配合而成的树脂组合物的成型方法、用途等没有特别限制，可以使用挤出成型、注射成型、吹塑成型、压延成型、压制成型、真空成型等公知的成型加工技术，成型为膜、片材、成型品等，用于汽车的内外装饰材料、家电产品、建筑材料、包装材料、农业用材料、杂货、医疗用器具等，有关使用形态，可以单独使用或与其它的树脂或金属等直接或通过粘接剂层贴合在一起等来使用。
下面，对本发明的聚丙烯系树脂组合物的制造方法进行说明。作为本发 明的聚丙烯系树脂组合物的制造方法中使用的聚丙烯系树脂，可以列举出丙烯均聚物、乙烯-丙烯无规共聚物、乙烯-丙烯嵌段共聚物、丙烯与少量（1～10质量%）的其它α-烯烃（例如1-丁烯、1-己烯、4-甲基-1-戊烯等）形成的共聚物、丙烯与乙丙烯形成的共聚物（TPO）等。
上述的聚丙烯系树脂可以不考虑聚合催化剂/助催化剂的种类或有无、有规立构性、平均分子量、分子量分布、特定的分子量成分的有无或比例、比重、粘度、在各种溶剂中的溶解度、伸长率、冲击强度、结晶度、X射线衍射、通过不饱和羧酸（马来酸、衣康酸、富马酸等）以及其衍生物（马来酸酐、马来酸单酯、马来酸二酯等）或有机过氧化物或者能量射线的照射以及这些处理的组合进行的改性/交联处理的有无等来使用。
本发明的聚丙烯系树脂组合物的制造方法中使用的通式（I）表示的二亚苄基山梨糖醇化合物的制造方法没有特别限定，可以使用公知的任意方法。
本发明的制造方法中使用的通式（I）表示的二亚苄基山梨糖醇化合物的粒径是，d97为30μm～200μm，d97特别优选为40μm～150μm。如果粉碎至d97低于30μm，则粉碎成本变高，而且会发生粘连而使操作性下降，因而不优选。d97如果大于200μm，则透明性不充分，成型为膜等时存在鱼眼增加等问题。此外，本发明中的d97，是指小于某一粒径的粒子量相对于总粒子量的百分比为97的粒径。
上述通式（I）表示的二亚苄基山梨糖醇化合物的配合量相对于上述的聚丙烯系树脂100质量份为0.05～2质量份，优选为0.1～1质量份。二亚苄基山梨糖醇化合物的配合量如果低于0.05质量份，则添加效果不充分，另外，超过2质量份添加，也看不到效果的提高。
作为将在上述的聚丙烯系树脂中配合了上述通式（I）表示的二亚苄基山梨糖醇化合物而得到的混合物进行混炼的双螺杆挤出机，优选从树脂投入部至口模之间具有至少3个温度管理区域的双螺杆挤出机，例如，可以优选使用株式会社池贝制造的双螺杆挤出机PCM-30（商品名）、株式会社日本制钢所制造的双螺杆挤出机TEX-28V（商品名）等。
通过上述双螺杆挤出机进行的混合物的混炼在挤出温度为220～250℃下、优选在230～250℃下进行。有关双螺杆挤出机的温度设定，在从双螺杆挤出机的树脂投入部至口模的区域，将除树脂投入部以外并且除口模以外的 部分的温度设定为220～250℃即可。
挤出温度如果低于220℃，则分散性差，难以表现出效果，而如果超过250℃，则会引起聚丙烯系树脂的劣化，因而不优选。
在上述的聚丙烯系树脂中配合上述通式（I）表示的二亚苄基山梨糖醇化合物时，优选将该二亚苄基山梨糖醇化合物和四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷以混合物的形态配合、或者将上述的化合物分别单独地同时配合。配合四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷时，相对于100质量份的上述二亚苄基山梨糖醇化合物，优选配合5～200质量份，特别优选配合10～150质量份。
另外，在将上述通式（I）表示的二亚苄基山梨糖醇化合物配合于上述的聚丙烯系树脂中而得到的混合物中，优选根据本发明的聚丙烯系树脂组合物的使用条件以及要求特性添加酚系抗氧化剂、磷系抗氧化剂、硫系抗氧化剂、紫外线吸收剂、受阻胺化合物、阻燃剂、阻燃助剂、其它的成核剂、抗静电剂、重金属惰性化剂、增塑剂、软化剂、润滑剂、水滑石化合物、脂肪酸金属盐、颜料、红外线吸收剂、防灰雾（antifogging）剂、防雾（antimist）剂、填充剂、抗菌/抗霉剂等常用的树脂添加剂。作为上述的树脂添加剂的具体例子，可以使用前述的那些。
本发明的聚丙烯系树脂组合物的成型方法、用途等没有特别限制，可以使用挤出成型、注射成型、吹塑成型、压延成型、压制成型、真空成型等公知的成型加工技术，成型为膜、片材、成型品等，用于汽车的内外装饰材料、家电产品、建筑材料、包装材料、农业用材料、杂货、医疗用器具等，有关使用形态，可以单独使用或与其它的树脂或金属等直接或通过粘接剂层贴合在一起等来使用。
实施例
合成例（通式（I）表示的二亚苄基山梨糖醇化合物的合成）
在反应用四口烧瓶中添加3,4-二甲基苯甲醛44g（0.42mol）、山梨糖醇38g（0.21mol）、作为催化剂的50%硫酸5g、作为溶剂的环己烷700ml以及甲醇70ml，在甲醇回流温度下进行搅拌。随时滴加与挥发的甲醇量相同量的甲醇，反应5小时而得到块状物。
用异丙醇/水=1/1（容积比）洗涤得到的块状物，在90℃下减压干燥过滤物。
用粉碎机粉碎得到的块，分别得到具有表1和表2记载的d97的二亚苄基山梨糖醇粉末（表1和表2中简记为山梨糖醇）。二亚苄基山梨糖醇粉末的d97用激光散射法测定。另外，对于得到的二亚苄基山梨糖醇粉末，使用粉末性能测试仪通过测定休止角来评价粘连性。各二亚苄基山梨糖醇粉末的休止角示于表1和表2中。休止角越大，表示流动性越差。
实施例1～5和比较例1～3
将合成例中得到的二亚苄基山梨糖醇粉末（表1中简记为山梨糖醇）和四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷的粉末（表1中简记为酚：使用株式会社ADEKA制造的ADEKA STAB AO-60）按照表1记载的配比混合，分别调制透明化剂组合物。
将上述的透明化剂组合物如下所述地配合于聚丙烯系树脂中，制作试验片。此外，比较例3中，不调制透明化剂组合物，将二亚苄基山梨糖醇粉末和四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷的粉末与其它的树脂添加剂一起，直接配合于聚丙烯系树脂中。
在无规聚丙烯（MFI=8～10g/10分钟、MG3：Japan Polypropylene株式会社制）100质量份中，配合四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷0.1质量份、三（2,4-二叔丁基苯基）亚磷酸酯0.05质量份、硬脂酸钙0.05质量份以及表1记载的透明化剂组合物0.3质量份，用亨舍尔混合机混合，并用双螺杆挤出机（株式会社池贝制造、PCM-30）进行挤出成型，得到颗粒。将得到的颗粒在250℃下进行注射成型，从而制作厚度为1mm的试验片。
使用熔融指数分析仪（东洋精机株式会社制造），根据JIS K7210对得到的颗粒测定230℃下的2.16kg负荷下的熔体流动指数（MFI），评价有无树脂物性的下降。MFI越大，树脂的物性变化越大，因而不优选。另外，根据JIS K 7361-1测定试验片的雾度（Haze），从而测定透明性提高效果。Haze的值越小，透明性越优良，因而是优选的。其结果示于表1中。
表1
由表1所示的结果可知如下情况。配合了本发明的透明化剂组合物的实施例1～5的聚丙烯系树脂具有优良的透明性，也没有物性的下降。与此相对，配合有使用了具有d97较小的粒径的二亚苄基山梨糖醇粉末的透明化剂组合物的比较例1的聚丙烯系树脂尽管透明性优良，但物性下降。另外，配合了由二亚苄基山梨糖醇粉末单独构成的透明化剂组合物的比较例2的聚丙烯系树脂的透明性变差，物性也大幅下降。另外，直接配合了二亚苄基山梨糖醇粉末和四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷粉末的比较例3的聚丙烯系树脂的结果是：透明性大大变差。
实施例6～8和比较例4～8
在无规聚丙烯（MFI=8～10g/10分钟、MG3：Japan Polypropylene株式会社制）100质量份中，配合四[3（3,5-二叔丁基-4-羟基苯基）丙酰氧基甲基]甲烷0.1质量份、三（2,4-二叔丁基苯基）亚磷酸酯0.05质量份、硬脂酸钙0.05质量份以及合成例中得到的具有表2记载的d97的二亚苄基山梨糖醇粉末0.2质量份，用亨舍尔混合机混合，使用表2记载的挤出机在表2记载的挤出温度下进行挤出成型，得到颗粒。将得到的颗粒在250℃下进行注射成型，从而制作厚度为1mm的试验片。
使用熔融指数分析仪（东洋精机株式会社制造），根据JIS K7210对得到的颗粒测定230℃下的2.16kg负荷下的熔体流动指数（MFI），评价有无树脂物性的下降。MFI越大，树脂的物性变化越大，因而不优选。另外，根据JIS K 7361-1测定试验片的雾度（Haze），从而测定透明性提高效果。Haze的值越小，透明性越优良，因而是优选的。其结果示于表2中。
表2
*1：作为双螺杆挤出机，使用株式会社池贝制造的PCM-30
作为单螺杆挤出机，使用株式会社DDM制造的OEX3024
由表2所示的结果可知如下情况。由实施例6与比较例5的对比可知，即使是相同组成，使用单螺杆挤出机时，透明性的改善效果小，通过使用双螺杆挤出机才获得了本发明的效果。另外，由比较例7和8可知，即使想通过提高加工温度而提高分散性，但在透明性、物性的稳定性方面也是不理想的结果，通过选择温度和加工机器才获得了本发明的效果。由实施例6和8与比较例4的对比可知，通过设定为本发明的加工条件，可以使流动性优良的粒径较大的二亚苄基山梨糖醇化合物在以往被认为较差的透明性和物性的稳定性方面，显示出与微粉化后的化合物同等的性能。此外，由比较例6可知，当使用d97的值接近300μm的二亚苄基山梨糖醇化合物时，即使在本发明的加工条件下，透明性也差，所以必须将二亚苄基山梨糖醇化合物的d97设定为200μm以下。
产业上的可利用性
根据本发明的透明化剂组合物，通过将以往无法获得充分的透明性的粒径较大的二亚苄基山梨糖醇化合物制成与特定的酚系抗氧化剂的混合物，然后添加到聚丙烯系树脂中，由此提供在不将二亚苄基山梨糖醇化合物进行微粉碎的情况下，也能够形成透明性优良的聚丙烯系树脂组合物的透明化剂组合物。
另外，根据本发明的聚丙烯系树脂组合物的制造方法，尽管二亚苄基山梨糖醇化合物不进行微粉化就配合于聚丙烯系树脂中，但仍然能够获得具有优良的透明性和物性的聚丙烯系树脂组合物。
Claims (3)
1.一种聚丙烯系树脂组合物的制造方法，其特征在于，在获得聚丙烯系树脂中配合有具有d97为30μm～200μm的粒径的下述通式（I）表示的二亚苄基山梨糖醇化合物的聚丙烯系树脂组合物时，将在100质量份的所述聚丙烯系树脂中配合了0.05～2质量份的所述二亚苄基山梨糖醇化合物而得到的混合物，使用双螺杆挤出机在220～250℃的挤出温度下进行混炼，
2.根据权利要求1所述的聚丙烯系树脂组合物的制造方法，其中，通式（I）表示的二亚苄基山梨糖醇化合物的d97为40μm～150μm。
3.根据权利要求1或2所述的聚丙烯系树脂组合物的制造方法，其中，作为双螺杆挤出机，使用从树脂投入部至口模之间具有至少3个温度管理区域的双螺杆挤出机，将除树脂投入部以外并且除口模以外的部分的温度设定为220～250℃。
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- 2011-03-08 EP EP20110762504 patent/EP2554591B1/en active Active
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- 2011-03-08 CN CN201180004943.6A patent/CN102725348B/zh not_active Expired - Fee Related
- 2011-03-08 WO PCT/JP2011/055357 patent/WO2011122264A1/ja active Application Filing
- 2011-03-08 US US13/575,136 patent/US20120296018A1/en not_active Abandoned
- 2011-03-08 KR KR1020127015253A patent/KR101874488B1/ko active IP Right Grant
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2014
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| CN1044127C (zh) * | 1992-05-01 | 1999-07-14 | 米利肯研究公司 | 粉末状澄清剂及将其混入半透明聚烯烃树脂中的方法 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105283501A (zh) * | 2013-05-31 | 2016-01-27 | 株式会社Adeka | 透明化剂组合物以及含有它的聚烯烃系树脂组合物 |
| US9701812B2 (en) | 2013-05-31 | 2017-07-11 | Adeka Corporation | Clarifying agent composition, and polyolefin resin composition containing same |
| CN105283501B (zh) * | 2013-05-31 | 2018-01-05 | 株式会社Adeka | 透明化剂组合物以及含有它的聚烯烃系树脂组合物 |
| CN114341246A (zh) * | 2019-07-08 | 2022-04-12 | 弗劳恩霍夫应用研究促进协会 | 酚取代的糖衍生物作为稳定剂的用途、塑料组合物、稳定塑料材料的方法和酚取代的糖衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103554650B (zh) | 2015-11-18 |
| US20140128520A1 (en) | 2014-05-08 |
| WO2011122264A1 (ja) | 2011-10-06 |
| EP2554591B1 (en) | 2014-12-24 |
| KR20130009738A (ko) | 2013-01-23 |
| TWI526447B (zh) | 2016-03-21 |
| EP2554591A4 (en) | 2013-08-21 |
| CN102725348B (zh) | 2014-02-05 |
| KR101874488B1 (ko) | 2018-07-04 |
| BR112012016841A2 (pt) | 2018-05-08 |
| EP2554591A1 (en) | 2013-02-06 |
| US20120296018A1 (en) | 2012-11-22 |
| CN102725348A (zh) | 2012-10-10 |
| US9441091B2 (en) | 2016-09-13 |
| TW201139448A (en) | 2011-11-16 |
| BR112012016841B1 (pt) | 2020-03-31 |
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