TW201920331A - 含膨脹之tpu及塗層之物件 - Google Patents
含膨脹之tpu及塗層之物件 Download PDFInfo
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- TW201920331A TW201920331A TW107122739A TW107122739A TW201920331A TW 201920331 A TW201920331 A TW 201920331A TW 107122739 A TW107122739 A TW 107122739A TW 107122739 A TW107122739 A TW 107122739A TW 201920331 A TW201920331 A TW 201920331A
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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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/14—Manufacture of cellular products
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/365—Coating
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/007—After-treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D35/00—Producing footwear
- B29D35/12—Producing parts thereof, e.g. soles, heels, uppers, by a moulding technique
- B29D35/14—Multilayered parts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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Abstract
本發明有關包括膨脹熱塑性聚胺甲酸酯作為基材及特定聚胺甲酸酯脲塗層於該基材上之物件,以及鞋類,製造該物件之方法及聚胺甲酸酯脲溶液之用途。已發現包括聚碳酸酯結構單元之聚胺甲酸酯脲塗層強烈結合於膨脹TPU基材,並維持膨脹TPU之固有性質。
Description
本發明有關包括膨脹熱塑性聚胺甲酸酯作為基材及特定塗層於該基材上之物件,以及鞋類,製造該物件之方法及聚胺甲酸酯脲溶液之用途。
膨脹熱塑性聚胺甲酸酯(TPU)已知其可撓性、彈性及潤濕性(WO 94/20568A1)。一般製造膨脹TPU係使用結果熱塑性聚胺甲酸酯組成要素之擠壓方法及隨後粒化方法。誘發顆粒膨脹可藉由蒸氣或熱空氣,藉由推進劑/發泡劑浸沒顆粒及接著熱處理(WO 2007/082838 A1)或使用例如含有推進劑/發泡劑之微球體母料(WO 2005/023920 A1)。各種推進劑/發泡劑有用於膨脹顆粒(WO 2010/136398 A1給予之概述)。
為了製造及成形分別物件,膨脹TPU通常被導入鑄模且暴露於蒸氣及/或熱,以致膨脹顆粒之外表面熔化。然而,當運輸膨脹TPU顆粒時,如將其倒入鑄模,而且運輸至袋子、桶子、通過管子等,彼等顆粒傾向互相黏著,造成凝塊及不利沉積於分別表面上。此一方面影響膨脹TPU顆粒之加工性,另一方面對整體物件製造方法之可控性及再現性具有負面影響。
因此,正常在製造期間或之後添加添加劑例如潤滑劑於膨脹TPU顆粒,以便減少上述黏著問題(如WO 2013/182555 A1)。雖然此等添加劑減少或防止運輸期間顆粒黏著,但其等亦餘留在欲製造的結果物件。因此,致力製造塗層於包括膨脹TPU的結果物件之任何方法面臨物件上潤滑劑亦對成形膨脹TPU表面與其本身塗層間黏著展現負面影響之問題。
因此,許多嘗試成功塗布膨脹TPU基材之實驗失敗。此係進一步由於膨脹TPU基材具撓性,因此分別塗層需要黏著於基材,甚至當此基材使用時
彎曲(如走路時鞋底)。因此,已知改良剛性表面抗性(如抗化學性、抗水性、抗刮性、抗紫外線性及/或耐久性)之許多塗層例如丙烯酸塗層再者亦破裂及從撓曲的撓性基材剝離。
然而,想要塗布彼等基材以便提供改良或裝飾外觀,施加圖案或增進抗水性、抗化學性、抗刮性、抗紫外線性及/或耐久性。
有些方法敘述將膨脹TPU顆粒本身染色以便改良膨脹TPU基材外觀。WO 2014/052243 A1以及WO 2005/023920 A1敘述添加染料以便改變結果物件顏色。然而,染色方法具有原則上確實需要的染料量超過獲得想要效果所需的染料量之缺點。因為僅可看見結果成形物件之外表面,物件內部之染料不需要。此導致製造包括膨脹TPU之染色物件時增加成本。再者,染料本身可影響膨脹TPU物件之結果性質,因此需要特別適應。
WO 2012/065926 A1敘述在製造具兩種組分聚胺甲酸酯之混合材料前,將膨脹顆粒首先經由洗滌從助劑的黏著殘渣脫除。使用硝酸及水執行洗滌。此方法造成額外清潔步驟,再者粗澀物質被用於洗滌。
WO 2009/120560 A1敘述包括發泡TPU之物件,其塗有水載兩種組分塗層組成物。然而,此文件僅敘述使用發泡TPU基材。製造TPU發泡體係使用與膨脹TPU完全不同的方法,因此並無面臨潤滑劑存在於分別基材外表面之問題。因此,此先前技藝文件敘述本質上不需要潤滑劑之發泡體表面上塗層因此沒有潤滑劑。為此理由,發明者發現所述塗層黏著於TPU發泡體。
就此先前技藝觀點,本發明目的係克服至少一項、較好所有先前技藝已知的不利條件。特別是,本發明目的係提供充分黏著於膨脹TPU之塗層。再者,本發明特別目的係在膨脹TPU上提供塗層,其甚至在膨脹TPU彎曲或撓曲時亦能黏著。較佳者,膨脹TPU不應洗滌或沒有存在其表面的潤滑劑。
藉由以下詳述根據本發明物件、本發明鞋類、製造根據本發明物件之方法及根據本發明用途已完成此等目的。
根據本發明,提供物件包括膨脹熱塑性聚胺甲酸酯作為基材及塗層於至少部分該基材上,其中固化包括至少一種有機溶劑之聚胺甲酸酯脲溶液
獲得塗層,特徵在於聚胺甲酸酯脲包括聚碳酸酯結構單元。
驚人地已發現包括至少一種有機溶劑之聚胺甲酸酯脲溶液(其中聚胺甲酸酯脲包括聚碳酸酯結構單元)黏著於膨脹TPU基材。再者,驚人地已發現甚至於膨脹TPU上存在潤滑劑,塗層於膨脹TPU上的黏著力亦足夠。因此,由於其製造方法,不需洗滌步驟或移除膨脹TPU表面上存在之添加劑。
在不希望受理論束縛下,據信聚胺甲酸酯脲塗層中聚碳酸酯結構單元促進黏著於膨脹TPU表面。再者,據信藉由使用列舉如下特定選擇的溶劑,可額外改良、較好加乘改良聚胺甲酸酯脲塗層與膨脹TPU表面之黏著。使用含有特定有機溶劑之聚胺甲酸酯脲溶液,據信部分溶解(亦即部分膨潤)膨脹TPU表面。存在於溶液之聚胺甲酸酯脲聚合物鏈因此可部分穿透膨脹TPU表面之粗鬆網路,導致溶劑蒸發時聚胺甲酸酯脲之物理包埋(形成相互穿透網路)。然而,因為膨脹TPU表面僅些微膨潤,膨脹TPU總體性質並未明顯受此方法影響且顯然完全維持。
再者,驚人地已發現甚至當物件彎曲或撓曲時,包括聚碳酸酯結構單元之聚胺甲酸酯脲塗層的黏著亦足夠。因此,在膨脹TPU上獲得穩定塗層,甚至當物件彎曲或撓曲時亦維持其黏著。同時較好於溫度範圍-20至+40℃,維持膨脹TPU基材之性質,亦即機械及/或官能性質。
此外,相較於無塗層之TPU表面,藉由塗布膨脹TPU基材,成功改良基材之抗水性、抗化學性、抗刮性、抗紫外線性及/或耐久性。尤其,相較於無塗層之TPU表面,藉由塗層可增加膨脹TPU表面之抗土壤性。再者,相較於無塗層之TPU表面,可減少膨脹TPU表面之粗糙度。
根據本發明,措辭「膨脹TPU」係指由熱塑性聚胺甲酸酯製造之顆粒發泡體。較佳者,此術語係指提供膨脹TPU顆粒並在鑄模中使其成形而獲得之產品。較佳者,沒有執行洗滌或清潔此結果成形物件,其能夠及/或意欲移除膨脹TPU顆粒表面上潛在存在之添加劑,較好潤滑劑。然而,此並非意謂膨脹TPU尚未以塗布基材前常用的傳統方式清潔,如移除灰塵等,藉以非故意移除膨脹TPU基材表面上若干添加劑。若需要,可使用PU清潔劑,較好以丙酮或醇為主,其可能較好包括小於5重量%離子或陰離子界面活性劑。PU清潔劑實例為Würth的PUSR500(Adolf Würth GmbH & Co.KG,
Künzelsau-Gaisbach,Germany)、Dr.Schutz的CC-PU-Reiniger(CC-Dr-Schutz GmbH,Bonn,Germany)等。因此,較好膨脹TPU基材實質上包括由於產品加工存在之多數添加劑。較佳者,膨脹TPU基材包括0.1至10重量份、更好0.25至7.55重量份、最好0.5至6重量份至少一種潤滑劑,以施加塗層時100份膨脹TPU為主。潤滑劑可存在呈均質分散於膨脹TPU基材。然而,較好累積於膨脹TPU顆粒表面。根據本發明,術語「潤滑劑」較好係指能夠維持或增進將膨脹的聚合物顆粒流動性之試劑。
較佳者,膨脹TPU具有封閉胞格結構。
熟習技藝人士已知適合TPU以及製備膨脹TPU基材之方法。較佳者,製造膨脹TPU基材係根據如WO 94/20568 A1、WO 2007/082838 A1、WO 2005/023920 A1、WO 2007/045586 A1、WO 2010/136398 A1、WO 2014/126799 A1及WO 2013/153153 A1敘述之任一項方法,其等有關膨脹TPU及/或膨脹TPU基材產品合併於此為參考。
較佳者,製造TPU係使異氰酸酯(a)與對異氰酸酯呈反應性化合物(b)之混合物反應,較好以莫耳質量0.5kg/mol至10kg/mol,且若合適,與鏈伸長劑(c)反應,較好以莫耳質量0.06kg/mol至0.5kg/mol。在其他較好具體實例中,針對製造TPU,至少一種鏈調節劑(c1)及至少一種觸媒(d),且若合適至少一種填料、助劑及/或至少一種添加劑(e)亦被加入混合物。
在製造TPU期間常用之組分(a)、(b)、(c)、(c1)、(d)及(e)舉例說明如下且包括下列物質之組群:異氰酸酯(a)、對異氰酸酯呈反應性化合物(b)、鏈伸長劑(c)、鏈調節劑(c1)、觸媒(d)、及/或至少一種傳統填料、助劑及/或添加劑(e)。
TPU製造一直需要由異氰酸酯(a)與對異氰酸酯呈反應性化合物(b)組成之混合物。進一步添加組分(c)、(c1)、(d)及(e)係視情況且可個別發生或藉由使用任何可能的變體。此處組分意謂個別物質或該組分內物質混合物。
若使用,組分異氰酸酯(a)、對異氰酸酯呈反應性化合物(b)、及鏈伸長劑(c)、及亦鏈調節劑(c1)被稱為結構組分。在較好具體實例中,所用有機異氰酸酯(a)包括脂族、環脂族、芳脂族、及/或芳香族異氰酸酯、
及亦較好二異氰酸酯。較好二異氰酸酯實例係三-、四-、五-、六-、七-、及/或八亞甲基二異氰酸酯、2-甲基五亞甲基1,5-二異氰酸酯、2-乙基伸丁基1,4-二異氰酸酯、五亞甲基1,5-二異氰酸酯、伸丁基1,4-二異氰酸酯、1-異氰酸基-3,3,5-三甲基-5-異氰酸基甲基環己烷(異佛酮二異氰酸酯,IPDI)、1,4-及/或1,3-雙(異氰酸基甲基)環己烷(HXDI)、環己烷1,4-二異氰酸酯、1-甲基環己烷2,4-及/或2,6-二異氰酸酯、及/或二環己基甲烷4,4’-、2,4’-、及2,2’-二異氰酸酯、二苯基甲烷2,2’-、2,4’-、及/或4,4’-二異氰酸酯(MDI)、伸萘基1,5-二異氰酸酯(NDI)、甲伸苯基2,4-及/或2,6-二異氰酸酯(TDI)、二苯基甲烷二異氰酸酯、3,3’-二甲基二苯基二異氰酸酯、1,2-二苯基乙烷二異氰酸酯、及伸苯基二異氰酸酯。
在較好具體實例中,所用對異氰酸酯呈反應性化合物(b)包括聚酯多元醇、聚醚多元醇、及/或聚碳酸酯二醇,其另外一般慣用術語係「多元醇」。
TPU較好從至少一種聚醚醇製造,特別好使用至少一種聚醚二醇。因此,結果膨脹熱塑性聚胺甲酸酯較好包括至少一種聚醚。非常特別好聚醚二醇為聚乙二醇及聚丙二醇。聚醚醇較好以莫耳質量0.6kg/mol至4.5kg/mol使用、特別好以莫耳質量0.8kg/mol至2.5kg/mol使用。聚醚醇係個別或另外呈各種聚醚醇混合物形式使用。
在替代具體實例中,從聚酯醇製造TPU。在較好具體實例中,聚酯二醇被用於此目的。一種較好聚酯二醇係從己二酸與1,4-丁烷二醇製造。聚酯醇之較好具體實例具有莫耳質量0.6kg/mol至4.0kg/mol、特別好具莫耳質量0.8kg/mol至2.5kg/mol。
在進一步較好具體實例中,該多元醇之平均官能度係1.8至2.3、或較好1.9至2.2、特別是2。
較好具體實例使用之鏈伸長劑(c)包括脂族、芳脂族、芳香族、及/或環脂族化合物,在進一步較好具體實例中具有莫耳質量0.06kg/mol至0.5kg/mol。在若干較好具體實例中,鏈伸長劑(c)係具有兩個官能基之化合物,例如二胺及/或於伸烷自由基具有2至10個碳原子之烷二醇(特別是1,2-乙烷二醇、1,4-丁烷二醇、1,6-己烷二醇、及/或具有4至20個碳原子之二-、三-、四-、五-、六-、七-、八-、九-、及/或十烷二醇),及對應寡-及/或聚丙
二醇。在進一步具體實例中,提及的鏈伸長劑混合物被用於製造TPU。
若干具體實例使用鏈調節劑(c1),通常以莫耳質量0.03kg/mol至0.5kg/mol。鏈調節劑係僅具有一個與異氰酸酯相關的官能基之化合物。鏈調節劑實例為一元醇、單官能胺(較好1-丁胺、1-己胺)、及/或一元多元醇(較好1-丁醇、1-己醇及1-辛醇)。鏈調節劑可用在由個別組分組成之混合物中調節想要的流動性質。
在較好具體實例中鏈調節劑用量係0重量%至5重量%、更好0.1重量%至1重量%,以對異氰酸酯呈反應性化合物(b)為基準。除了鏈伸長劑外,使用鏈調節劑代替此等。
在進一步具體實例中,至少一種觸媒(d)被用於TPU製造,特別是加速二異氰酸酯(a)的NCO基與對異氰酸酯呈反應性化合物、較好結構組分(b)的羥基、(c)、及(c1)間反應。在較好具體實例中,觸媒已選自三級胺、如三乙胺、二甲基環己胺、N-甲基嗎啉、N,N’-二甲基哌、2-(二甲胺基乙氧基)乙醇、二吖雙環[2.2.2]辛烷、及相似物質之組群。在進一步較好具體實例中,至少一種觸媒已選自有機金屬化合物之組群,可提及之實例為鈦酸酯、鐵化合物(如乙醯丙酮鐵(III))、錫化合物(如二乙酸錫(II)、二辛酸錫(II)、二月桂酸錫(II))、或脂族羧酸之二烷錫鹽(如二乙酸二丁錫、二月桂酸二丁錫)等。
若干具體實例個別使用觸媒,其他具體實例使用至少兩種提及觸媒之混合物。在較好具體實例中,觸媒或觸媒混合物之用量係0.0001重量%至0.1重量%,以對異氰酸酯呈反應性化合物(b)、較好多羥基化合物為基準。水解穩定劑(例如聚合及低分子量碳二醯亞胺)亦可與觸媒(d)一起或未使用觸媒下加入結構組分(a)至(c)及若合適(c1)。
在進一步具體實例中,TPU可包括磷化合物。較好具體實例使用之磷化合物包括三價磷之有機磷化合物,如亞磷酸酯及亞膦酸酯。適合磷化物實例為亞磷酸三苯酯、亞磷酸二苯基烷酯、亞磷酸苯基二烷酯、參(壬基苯基)亞磷酸酯、亞磷酸三月桂酯、亞磷酸三-十八烷酯、二硬脂基新戊四醇二亞磷酸酯、參(2,4-二第三丁基苯基)亞磷酸酯、二異癸基新戊四醇二亞磷酸酯、二(2,4-二第三丁基苯基)新戊四醇二亞磷酸酯、三硬脂基山梨醇三亞磷
酸酯、肆(2,4-二第三丁基苯基)4,4’-二伸苯基二亞膦酸酯、三異癸基亞磷酸酯、二異癸基苯基亞磷酸酯、及二苯基異癸基亞磷酸酯、或其混合物。
特別好具體實例包括難以水解之磷化合物,因為磷化合物水解成對應酸可導致損害聚胺甲酸酯,特別是聚酯胺甲酸酯。因此,特別針對聚酯胺甲酸酯,適合磷化合物係特別抗水解者。抗水解磷化合物之較好具體實例為二聚丙二醇苯基亞磷酸酯、三異癸基亞磷酸酯、三苯基單癸基亞磷酸酯、三異壬基亞磷酸酯、參(2,4-二第三丁基苯基)亞磷酸酯、肆(2,4-二第三丁基苯基)4,4’-二伸苯基二亞膦酸酯、及二(2,4-二第三丁基苯基)新戊四醇二亞磷酸酯、或其混合物。
在進一步具體實例中,TPU可包括進一步像抗氧化劑、光穩定劑、UV穩定劑、光學亮光劑及脫模劑之添加劑。
結構組分(b)及(c)之莫耳比率可相對廣泛變化。在較好具體實例中,組分(b)相對於所用鏈伸長劑(c)總量之莫耳比率自10:1至1:10變化、較好自5:1至1:8、更好自3:1至1:4,隨著鏈伸長劑(c)含量增加,此處TPU硬度提高。
如上述已解釋,在膨脹方法前及/或後,結果膨脹TPU顆粒提供至少一種潤滑劑。適合潤滑劑實例為滑石、金屬化合物(例如磷酸三鈣、碳酸鈣)、二氧化矽(特別是煙燻二氧化矽,例如來自Degussa的Aerosil®)、長鏈(如C10-22)羧酸鹽(例如硬脂酸鹽,例如硬脂酸鈣)、長鏈羧酸酯(如甘油酯,例如甘油硬脂酸酯)、矽氧油及聚四氟乙烯。通常經由混合、噴灑塗布、鼓輪塗布、或其他傳統方法,將潤滑劑塗敷於視情況膨脹TPU顆粒。一般用量係0.01至20重量份、較好0.1至10重量份、特別好0.5至6重量份,以100重量份視情況膨脹TPU為基準。
因此,根據本發明,膨脹熱塑性聚胺甲酸酯較好額外包括至少一種潤滑劑。更佳者,至少一種潤滑劑選自由滑石、金屬化合物、二氧化矽、C10至C22羧酸鹽、C10至C22羧酸酯、聚矽氧油、聚四氟乙烯或其至少兩種組合所構成之組群。又較佳者,至少一種潤滑劑選自由硬脂酸酯、滑石、聚矽氧油、甘油酯、聚四氟乙烯或其至少兩種組合所構成之組群。
根據本發明,膨脹TPU基材至少部分塗有由固化包括至少一種有機溶
劑的聚胺甲酸酯脲溶液獲得之塗層,其中聚胺甲酸酯脲包括聚碳酸酯結構單元。較佳者,由塗層範圍10至100%、或較好範圍20至100%、或較好範圍30至100%、或較好範圍30至70%、或較好範圍40至60%,以基材總表面為基準,塗布基材。若塗布具有內與外表面之封閉或本質封閉的結構,像鞋子、袋子、類似座椅,較好僅至少部分基材之外表面被塗層塗布。
根據本發明,術語「塗層」係指經由定義界面而與基材接觸之層。定義界面實例係塗層與表面之直接接觸、經由可區域限制的進一步層之間接接觸。較佳者,塗層係與基材直接接觸。較佳者,塗層較基材本身更薄。較佳者,塗層具有厚度範圍1至100μm、或較好範圍1.5至50μm、或較好範圍3至25μm。
熟習技藝人士已知用於塗布膨脹TPU基材之分別聚胺甲酸酯脲溶液。
較佳者,根據本發明聚胺甲酸酯脲係由至少以下浸提物之反應獲得:a)聚碳酸酯二醇,b)脂族或環脂族二胺或肼作為鏈伸長劑,及c)脂族、環脂族或芳香族二異氰酸酯。
更佳者,根據本發明聚胺甲酸酯脲係由至少以下浸提物之反應獲得:a)至少一種具有分子量600至4000g/mol、特別好1000至3000g/mol之巨二醇(聚醚二醇、聚酯二醇或聚碳酸酯二醇),或至少兩種該巨二醇組分之混合物,或一種該巨二醇與具有分子量50至500g/mol之短鏈脂族二醇的混合物(每莫耳巨二醇添加0.2至0.5莫耳短鏈脂族二醇),條件係使用至少一種聚碳酸酯二醇,b)每莫耳巨二醇0.5至2.0莫耳脂族或環脂族二胺或肼作為所謂鏈伸長劑,及c)每莫耳巨二醇1.5至3.0莫耳脂族、環脂族或芳香族二異氰酸酯、較好脂族或環脂族二異氰酸酯。
巨二醇a)(亦即較好具有平均羥基官能度約1.8至2.2、或較好1.95至2.05之多羥基化合物)根本上適合,條件係使用至少一種聚碳酸酯二醇。欲避免更高程度的巨二醇分支,因為高程度交聯給予結果聚胺甲酸酯脲溶液非常高黏度,其不利於加工為塗層溶液。
適合聚碳酸酯二醇係由二醇(例如1,3-丙烷二醇、1,4-丁烷二醇、1,6-己烷二醇或二-、三-或四乙二醇)與碳酸二芳酯或碳酸二烷酯或光氣反應可製備者。較好聚碳酸酯二醇係以1,6-己烷二醇為主者以及具有改質作用之共二醇(如1,4-丁烷二醇)或ε-己內酯。
適合含有羥基之聚醚係如於BF3存在下由環狀醚(例如環氧乙烷、環氧丙烷、環氧丁烷、四氫呋喃、氧化苯乙烯或表氯醇)與其本身聚合製備者,或將此等環化合物視情況呈混合物或接續添加於具有活性氫原子之起始物組分(例如醇及胺,實例為水、乙二醇、1,2-丙二醇或1,3-丙二醇)上製備者。
適合含有羥基之聚酯係如多元醇(較好二元醇)與多元羧酸(較好二元羧酸)之反應產物。代替游離羧酸,亦可使用對應聚羧酸酐或低級醇之對應聚羧酸酯、或其至少兩種混合物製備聚酯。
聚羧酸可有脂族、環脂族、芳香族及/或雜環天性,且可被如鹵素原子取代、及/或未取代。以下可提及為實例:
琥珀酸、己二酸、癸二酸、酞酸、異酞酸、1,2,4-苯三甲酸、酞酸酐、四氫酞酸酐、六氫酞酸酐、四氯酞酸酐、戊二酸酐、順丁烯二酸、順丁烯二酸酐、反丁烯二酸或對酞酸二甲酯。
適合多元醇實例為乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、2,3-丁二醇、1,6-己烷二醇、1,8-辛烷二醇、新戊二醇或2-甲基-1,3-丙烷二醇。亦可使用來自內酯之聚酯,如己內酯。
適合短鏈脂族二醇實例為乙二醇、丙二醇、新戊二醇、二乙二醇、三乙二醇、二乙醇胺、2-乙基-1,3-己烷二醇、N-甲基二異丙醇胺、1,3-丙烷二醇、1,4-丙烷二醇、1,3-丁烷二醇、1,4-丁烷二醇或1,6-己烷二醇。每莫耳巨二醇添加0.2至0.5莫耳短鏈脂族二醇。
所謂鏈伸長劑b)亦較好被用於製造根據發明使用之聚胺甲酸酯脲溶液。如此鏈伸長劑為肼或脂族二胺,如伸乙二胺、伸丙二胺、1,6-六亞甲二胺或其他脂族二胺。亦適合係環脂族二胺,例如1,4-雙(胺甲基)環己烷、4,4’-二胺基-3,3’-二甲基二環己基甲烷及其他(C1-C4)-二烷基-與(C1-C4)-四烷基二環己基甲烷,如4,4’-二胺基-3,5-二乙基-3’,5’-二異丙基二環己基甲烷。1-胺
基-3,3,5-三甲基-5-胺甲基環己烷(異佛酮二胺)及4,4’-二胺基二環己基甲烷為較佳。
每莫耳巨二醇混合物a)使用約0.5至2.0莫耳、較好0.6至1.7莫耳鏈伸長劑b)。
傳統使用大約等當量的鏈伸長劑,以扣除已與巨二醇混合物反應的異氰酸酯比例後剩餘之異氰酸酯為主。然而,較好使用小於等當量、低至約30至80%NCO基。殘留NCO基可與單官能終止劑反應,例如丁胺、硬脂胺、三烷氧矽基丙烷胺、丁酮肟或嗎啉。此防止分子量過度成長或交聯及分支反應。溶劑混合物含有之醇亦以此形式作用為鏈伸長劑。
可用的二異氰酸酯c)係熟習技藝者已知之所有脂族、環脂族及/或芳香族異氰酸酯,其具有平均NCO官能度≧1、較好≧2,個別或互相呈任何想要的混合物,彼等是否已由光氣法或無光氣法製備並不重要。
較好使用來自脂族或環脂族系列之異氰酸酯,其等碳骨架(存在的NCO基除外)具有3至30個碳原子、較好4至20個碳原子。
特別好化合物組分c)對應具脂族及/或環脂族鍵結的NCO基之前述類型,例如雙(異氰酸基烷基)醚、雙-與參-(異氰酸基烷基)苯、-甲苯與-二甲苯、丙烷二異氰酸酯、丁烷二異氰酸酯、戊烷二異氰酸酯、己烷二異氰酸酯(如六亞甲基二異氰酸酯,HDI)、庚烷二異氰酸酯、辛烷二異氰酸酯、壬烷二異氰酸酯(如三甲基-HDI(TMDI)、正常呈2,4,4與2,2,4異構物之混合物)、壬烷三異氰酸酯(如4-異氰酸基甲基-1,8-辛烷二異氰酸酯)、癸烷二異氰酸酯、癸烷三異氰酸酯、十一烷二異氰酸酯、十一烷三異氰酸酯、十二烷二異氰酸酯、十二烷三異氰酸酯、1,3-與1,4-雙(異氰酸基甲基)環己烷(H6XDI)、3-異氰酸基甲基-3,5,5-三甲基環己基異氰酸酯(異佛酮二異氰酸酯,IPDI)、雙(4-異氰酸基環己基)甲烷(H12MDI)或雙(異氰酸基甲基)降莰烷(NBDI)。
非常特別好化合物組分c)為六亞甲基二異氰酸酯(HDI)、三甲基-HDI(TMDI)、2-甲基-1,5-戊烷二異氰酸酯(MPDI)、異佛酮二異氰酸酯(IPDI)、1,3-與1,4-雙(異氰酸基甲基)環己烷(H6XDI)、雙(異氰酸基甲基)降莰烷(NBDI)、3(4)-異氰酸基甲基-1-甲基環己基異氰酸酯(IMCI)及/或4,4’-雙
(4-異氰酸基環己基)甲烷(H12MDI)、或至少兩種此等異氰酸酯之混合物。
每莫耳巨二醇混合物a)使用約1.5至3.0莫耳、較好1.7至2.8莫耳二異氰酸酯組分c)。
為了製造根據發明聚胺甲酸酯脲,至少一種包括聚碳酸酯二醇(視情況低分子量脂族二醇)之巨二醇與二異氰酸酯呈熔融或呈溶液一起反應,直到已消耗所有羥基。隨後添加進一步溶劑及二胺鏈伸長劑,視情況於溶液。當已達到目標黏度時,用單官能脂族胺或用丁酮肟封阻殘留NCO基。
較佳者,結果聚胺甲酸酯脲包括烷氧基矽烷結構單元。藉由使用含有停止劑之烷氧基矽烷基,將此等結構單元較好導入聚胺甲酸酯脲。較佳者,使用含有至少一個烷氧基矽烷基與異氰酸酯反應性基之至少一種化合物,導入結構單元。烷氧基矽烷化合物較好為胺烷基矽氧烷例如3-胺丙基三乙氧基矽烷、3-胺丙基三甲氧基矽烷、3-胺丙基三丁氧基矽烷、2-胺乙基三乙氧基矽烷、2-胺乙基三甲氧基矽烷、2-胺乙基三丁氧基矽烷、4-胺丁基三乙氧基矽烷、4-胺丁基三甲氧基矽烷,所提烷氧基矽烷與順丁烯二酸二烷酯(如順丁烯二酸二乙酯、順丁烯二酸二甲酯或順丁烯二酸二丁酯)之反應產物,N-苯基胺丙基三甲氧基矽烷,雙-(3-三甲氧基矽基丙基)胺,一或兩個烷氧基被烷基取代之所提化合物類型及至少兩種所提烷氧基矽烷與其他烷氧基矽烷之混合物。
已發現烷氧基矽烷結構單元改良結果聚胺甲酸酯脲塗層之水解穩定性。再者,額外改良對膨脹TPU基材之黏著。
根據本發明聚胺甲酸酯脲溶液之至少一種有機溶劑係較好選自由甲苯、異丙醇、1-甲氧基丙烷-2-醇、1-甲氧基丙基乙酸酯、γ-丁內酯、丙二醇單甲醚、2-丁酮、乙酸乙酯或其至少兩種組合所構成之組群。此等有機溶劑驚人地導致聚胺甲酸酯脲與膨脹TPU基材之改良黏著。據信此等溶劑展現上述性質,造成膨脹TPU基材之外表層與聚胺甲酸酯脲塗層間形成互穿網路。此方面最佳者,至少一種有機溶劑包括γ-丁內酯。又最佳者,至少一種有機溶劑為2-丁酮。此溶劑較好係因為其結合上述性質且額外於毒物學上可接受。
較佳者,至少一種有機溶劑係至少兩種上述溶劑之混合物。更佳者,
混合物包括2-丁酮及至少一種選自由γ-丁內酯、乙醇、正丙醇、異丙醇、丙二醇單甲醚及1-甲氧基-2-丙醇所構成之組群之其他有機溶劑。再者,亦可同時使用酯及酮,例如乙酸乙酯、乙酸丁酯、丙酮、甲乙酮及甲基異丁酮。最佳者,混合物包括2-丁酮及丙二醇單甲醚。
最佳者,γ-丁內酯比例(以聚胺甲酸酯脲溶液總重為基準)係1重量%至80重量%、較好3重量%至20重量%、最好4重量%至10重量%。
又較佳者,2-丁酮比例(以聚胺甲酸酯脲溶液總重為基準)係1重量%至80重量%、較好25重量%至75重量%、最好50重量%至70重量%。
較佳者,包括至少一種有機溶劑之聚胺甲酸酯脲溶液含有5至60重量%固體、或較好6至40重量%固體。
在本發明態樣中,聚胺甲酸酯脲溶液額外包括至少一種著色劑。因此,藉由塗布膨脹TPU基材,就提供顏色及/或圖案而論可改良其外觀。根據本發明物件可較已知染色物件更方便製造,因為可精確定位至少一種顏色,亦即特別提供想要的地方。
可同時使用傳統添加劑與助劑物質,例如改良手感試劑、染料、消光劑、UV穩定劑、酚系抗氧化劑、光穩定劑、疏水劑及/或流動控製劑。
在本發明較好具體實例中,聚胺甲酸酯脲溶液額外包括至少一種聚異氰酸酯。此額外聚異氰酸酯改良基材與塗層間之鍵結強度。較佳者,額外聚異氰酸酯為寡聚異氰酸酯。可用之聚異氰酸酯較好係熟習技藝者已知之所有脂族、環脂族及/或芳香族異氰酸酯,其具有平均NCO官能度≧1、較好≧2,個別或互相呈任何想要的混合物,彼等是否已由光氣法或無光氣法製備並不重要。更佳者,聚異氰酸酯係選自由異氰酸酯二聚體(uretdione)、三聚異氰酸酯、亞胺基二二酮及/或二三酮結構及經縮二脲化的二異氰酸酯或其至少兩種的混合物所構成之組群之寡聚異氰酸酯。較佳者,聚異氰酸酯係經聚合、例如三聚合或經縮二脲化的脂族、芳脂族或芳香族二異氰酸酯。適合如此異氰酸酯之改質反應係例如催化低聚合異氰酸酯形成異氰酸酯二聚體、三聚異氰酸酯、亞胺基二二酮、胺甲酸酯、脲甲酸酯及/或二三酮結構之傳統方法或縮二脲化二異氰酸酯之傳統方法,例如舉例說明於Laas et al,J.Prakt.Chem.336,1994,185-200、DE-A 1 670
666及EP-A 0 798 299。如此以芳脂族二異氰酸酯為主聚異氰酸酯之具體敘述亦被發現於如EP-A 0 081 713、EP-A 0 197 543、GB-A 1 034 152及JP-A 05286978。
特別好聚異氰酸酯係具脂族及/或環脂族鍵結的NCO基者,例如雙(異氰酸基烷基)醚、雙-與參-(異氰酸基烷基)苯、-甲苯與-二甲苯、丙烷二異氰酸酯、丁烷二異氰酸酯、戊烷二異氰酸酯、己烷二異氰酸酯(如六亞甲基二異氰酸酯,HDI)、庚烷二異氰酸酯、辛烷二異氰酸酯、壬烷二異氰酸酯(如三甲基-HDI(TMDI)、正常呈2,4,4與2,2,4異構物之混合物)、壬烷三異氰酸酯(如4-異氰酸基甲基-1,8-辛烷二異氰酸酯)、癸烷二異氰酸酯、癸烷三異氰酸酯、十一烷二異氰酸酯、十一烷三異氰酸酯、十二烷二異氰酸酯、十二烷三異氰酸酯、1,3-與1,4-雙(異氰酸基甲基)環己烷(H6XDI)、3-異氰酸基甲基-3,5,5-三甲基環己基異氰酸酯(異佛酮二異氰酸酯,IPDI)、雙(4-異氰酸基環己基)甲烷(H12MDI)或雙(異氰酸基甲基)降莰烷(NBDI)。
若額外聚異氰酸酯存在於聚胺甲酸酯脲溶液,存在量較好為0.1至10.0重量份、或較好0.2至8重量份、或較好0.3至5.0重量份、或較好0.5至4.0重量份,各次較好以100重量份聚胺甲酸酯脲溶液為基準。此額外聚異氰酸酯量有效改良結果聚胺甲酸酯脲塗層對基材之鍵結強度,同時確保塗層本身仍具足夠撓性,以免影響或對膨脹TPU基材有影響。
較佳者,根據本發明物件係選自由鞋底、襯墊、座椅(如汽車座椅或兒童座椅)、管(如自行車內胎)、輥(如艙室輥)、保險桿(如汽車保險桿)與床墊或其至少兩種組合所構成之組群。最佳者,根據本發明物件為鞋底。
在本發明另外態樣中,提供包括根據本發明物件之鞋類。
根據本發明,術語「包括」及/或「含有」較好意謂「實質上包括」,更好意謂「由…組成」。
本說明書陳述之任何分子質量為數量平均分子量。此說明書目的之數量平均分子量一直由膠透層析術(GPC)於23℃四氫呋喃中決定。此程序係根據DIN 55672-1:"Gel permeation chromatography,Part 1-Tetrahydrofuran as eluent"(來自PSS Polymer Service之SECurity GPC系統,流速1.0ml/min,管柱:2×PSS SDV linear M,8×300mm,5μm,RID偵檢器)。使用已知莫耳
質量之聚苯乙烯樣品舉行校準。以軟體協助計算數量平均分子量。基線點及評估極限係根據DIN 55672 Part 1詳載。
再者,本發明有關製造根據以上各具體實例所述本發明物件之方法。
根據本發明方法,包括至少以下步驟:1)提供包括膨脹熱塑性聚胺甲酸酯之基材,2)將包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於步驟1)至少部分該基材上,其中聚胺甲酸酯脲包括聚碳酸酯結構單元,3)固化步驟2)該聚胺甲酸酯脲溶液,以便獲得塗層,且4)視情況重複步驟2)及3)至少一次,其中重複步驟2)時,將包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於步驟3)或重複步驟3)獲得之固化塗層。
有關根據本發明物件,已詳細敘述基材及聚胺甲酸酯脲溶液。所有較好具體實例及具體實例組合可用於根據本發明方法。
較佳者,根據本發明方法步驟2)中,藉由刷塗、噴灑、滾動、輥塗、槽塗、浸漬及/或印刷,將包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於基材。熟習技藝人士能夠製備展現分別應用技術所需性質(黏度等)之分別溶液。然而,步驟2)中及/或重複步驟2)時使用之聚胺甲酸酯脲溶液根據DIN EN ISO 3219/A.3較好具有黏度範圍50至40,000mPas、或較好範圍500至10,000mPas、或較好範圍1000至8000mPas、或較好範圍1500至5000mPas
又較佳者,用熱實現固化步驟3)聚胺甲酸酯脲溶液。溫度需要適應基材性質。較佳者,使用溫度40至100℃、更好50至90℃、最好60至80℃。
在步驟4)較好具體實例中,重複一次步驟2)及3)。此意謂首先提供包括固化塗層之基材,在此固化塗層頂上,將包括至少一種有機溶劑之聚胺甲酸酯脲溶液(其中聚胺甲酸酯脲包括聚碳酸酯結構單元)塗敷於固化塗層。由此將(至少)兩層塗層建構於基材上。此具體實例中,已用於步驟2)之相同聚胺甲酸酯脲溶液可被用於步驟4),或可使用包括至少一種有機溶劑之不同聚胺甲酸酯脲溶液(其中聚胺甲酸酯脲包括聚碳酸酯結構單
元)。較佳者,相較於最先步驟2)之聚胺甲酸酯脲溶液,重複步驟2)使用之不同聚胺甲酸酯脲溶液包括至少不同聚胺甲酸酯脲溶液之有機溶劑量。此意謂在步驟4)較好具體實例中,重複步驟2)時使用之聚胺甲酸酯脲溶液不同於步驟2)使用之聚胺甲酸酯脲溶液(亦即第一次進行步驟2)時),條件係使用包括至少一種有機溶劑之聚胺甲酸酯脲溶液,其中聚胺甲酸酯脲包括聚碳酸酯結構單元。較佳者,聚胺甲酸酯脲溶液為任一種上述聚胺甲酸酯脲溶液。
在又另外態樣中,本發明有關包括至少一種有機溶劑之聚胺甲酸酯脲溶液之用途,其係於包括膨脹熱塑性聚胺甲酸酯基材之裝飾性塗層,其中聚胺甲酸酯脲包括聚碳酸酯結構單元。
*包括聚碳酸酯結構單元之脂族聚胺甲酸酯脲,30%固體含量於1-甲氧基丙基乙酸酯/γ-丁內酯/異丙醇/1-甲氧基丙烷-2-醇7:23:20:20。
**以六亞甲基二異氰酸酯為主之縮二脲結構。
為了獲得聚胺甲酸酯脲溶液A,首先將Impranil 2610與丙二醇單甲醚均質混合。接著,緩慢添加2-丁酮,同時攪拌。然後添加顏料。
最後,添加Desmodur N 75 MPA/x-cn並分散於溶液。
用2ml/cm2 Würth的PUSR500(Adolf Würth GmbH & Co.KG,Künzelsau-Gaisbach,Germany)清潔WO 2007/045586 A1中根據實施例1獲得之膨脹TPU鞋底。
使用傳統噴槍,將分散液A塗敷於清潔之膨脹TPU基材。塗布白色基材直到不再看見此基材之白色。使塗布基材於70℃固化10分鐘。
使用手工橡膠/EVA層合方法試驗基材塗層之黏著。此試驗中,一個人用手利用其全部力量,試著用手將塗層與基材分開。不可決定塗層層合。
*包括聚碳酸酯結構單元之脂族聚胺甲酸酯脲,30%固體含量於1-甲氧基丙基乙酸酯/γ-丁內酯/異丙醇/1-甲氧基丙烷-2-醇7:23:20:20。
**以六亞甲基二異氰酸酯為主之縮二脲結構。
為了獲得聚胺甲酸酯脲溶液,首先將Impranil 2610與丙二醇單甲醚均質混合。接著,緩慢添加2-丁酮,同時攪拌。
最後,添加Desmodur N 75 MPA/x-cn並分散於溶液。
將分散液B塗敷於膨脹TPU基材,該基材塗有藉由使用噴槍固化溶液A獲得之塗層。使塗布基材於70℃固化10分鐘。
使用手工橡膠/EVA層合方法試驗基材塗層之黏著。此試驗中,一個人用手利用其全部力量,試著用手將塗層與基材分開。不可決定塗層層合。
在實施例1及2兩者中,乾燥塗布基材後,完成具乾燥觸感之表面,其具撓性且使用時將不會剝落。可能利用為正常使用鞋子或日常生活之其他物件。表面可藉由添加不同顏料改變顏色。
Claims (15)
- 一種包括膨脹熱塑性聚胺甲酸酯作為基材及塗層於至少部分該基材上之物件,其中藉由固化包括至少一種有機溶劑之聚胺甲酸酯脲溶液以獲得塗層,特徵在於該聚胺甲酸酯脲包括聚碳酸酯結構單元。
- 根據請求項1之物件,其中該膨脹熱塑性聚胺甲酸酯包括至少一種聚醚。
- 根據請求項1或2中任一項之物件,其中該膨脹熱塑性聚胺甲酸酯額外包括至少一種潤滑劑。
- 根據請求項4之物件,其中該至少一種潤滑劑係選自由滑石、金屬化合物、二氧化矽、C10至C22羧酸鹽、C10至C22羧酸酯、聚矽氧油、聚四氟乙烯或其至少兩種組合所構成之組群。
- 根據請求項1至4中任一項之物件,其中該聚胺甲酸酯脲係由至少以下浸提物之反應獲得:a)聚碳酸酯二醇,b)脂族或環脂族二胺或肼作為鏈伸長劑,及c)脂族、環脂族或芳香族二異氰酸酯。
- 根據請求項1至5中任一項之物件,其中該聚胺甲酸酯脲包括烷氧基矽烷結構單元。
- 根據請求項1至6中任一項之物件,其中該至少一種有機溶劑係選自由甲苯、異丙醇、1-甲氧基丙烷-2-醇、1-甲氧基丙基乙酸酯、γ-丁內酯、丙二醇單甲醚、2-丁酮、乙酸乙酯或其至少兩種組合所構成之組群。
- 根據請求項1至7中任一項之物件,其中該聚胺甲酸酯脲溶液額外包括至少一種著色劑。
- 根據請求項1至8中任一項之物件,其中該聚胺甲酸酯脲溶液額外包括至少一種聚異氰酸酯。
- 根據請求項1至9中任一項之物件,其中該物件係選自由鞋底、座椅(如汽車座椅或兒童座椅)、管(如自行車內胎)、輥(如艙室輥)、保險桿(如汽車保險桿)、襯墊與床墊或其至少兩種組合所構成之組群。
- 一種鞋類,包括根據請求項1至10中任一項之物件。
- 一種製造根據請求項1至10中任一項物件之方法,包括以下步驟:1)提供包括膨脹熱塑性聚胺甲酸酯之基材,2)將包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於步驟1)之至少部分該基材上,其中該聚胺甲酸酯脲包括聚碳酸酯結構單元,3)固化步驟2)之該聚胺甲酸酯脲溶液,以便獲得塗層,且4)視情況重複步驟2)及3)至少一次,其中重複步驟2)時,將該包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於步驟3)或重複步驟3)獲得之固化塗層。
- 如請求項12之方法,其中在步驟2)中,藉由刷塗、噴灑、滾動、輥塗、槽塗、浸漬及/或印刷,將包括至少一種有機溶劑之聚胺甲酸酯脲溶液塗敷於基材。
- 根據請求項12或13中任一項之方法,其中步驟2)中及/或重複步驟2)時使用之聚胺甲酸酯脲溶液具有根據DIN EN ISO 3219/A.3之黏度50至40,000mPas。
- 一種包括至少一種有機溶劑之聚胺甲酸酯脲溶液之用途,其係用於包括膨脹熱塑性聚胺甲酸酯基材之裝飾性塗層,其中該聚胺甲酸酯脲包括聚碳酸酯結構單元。
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EP17179592.5A EP3424973A1 (en) | 2017-07-04 | 2017-07-04 | Article comprising expanded tpu and a coating |
EP17179592.5 | 2017-07-04 | ||
??17179592.5 | 2017-07-04 |
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TW201920331A true TW201920331A (zh) | 2019-06-01 |
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US (1) | US20200115489A1 (zh) |
EP (2) | EP3424973A1 (zh) |
JP (1) | JP7183201B2 (zh) |
KR (1) | KR20200026913A (zh) |
CN (1) | CN110831999B (zh) |
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WO (1) | WO2019007767A1 (zh) |
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- 2018-06-27 WO PCT/EP2018/067207 patent/WO2019007767A1/en unknown
- 2018-06-27 US US16/622,985 patent/US20200115489A1/en not_active Abandoned
- 2018-07-02 TW TW107122739A patent/TWI763876B/zh not_active IP Right Cessation
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TWI763876B (zh) | 2022-05-11 |
WO2019007767A1 (en) | 2019-01-10 |
US20200115489A1 (en) | 2020-04-16 |
EP3649171A1 (en) | 2020-05-13 |
EP3424973A1 (en) | 2019-01-09 |
KR20200026913A (ko) | 2020-03-11 |
CN110831999B (zh) | 2021-12-14 |
JP2020525319A (ja) | 2020-08-27 |
JP7183201B2 (ja) | 2022-12-05 |
EP3649171B1 (en) | 2021-02-24 |
CN110831999A (zh) | 2020-02-21 |
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