TW202330816A - 來自可再生來源之α,α支鏈酸的縮水甘油酯及其調配物 - Google Patents
來自可再生來源之α,α支鏈酸的縮水甘油酯及其調配物 Download PDFInfo
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- TW202330816A TW202330816A TW112111522A TW112111522A TW202330816A TW 202330816 A TW202330816 A TW 202330816A TW 112111522 A TW112111522 A TW 112111522A TW 112111522 A TW112111522 A TW 112111522A TW 202330816 A TW202330816 A TW 202330816A
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- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
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- RPQRZJDCBAVXKL-UHFFFAOYSA-N disodium propan-2-olate Chemical compound [Na+].CC([O-])C.[Na+].CC([O-])C RPQRZJDCBAVXKL-UHFFFAOYSA-N 0.000 description 1
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- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
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- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明係關於衍生自與表鹵醇反應之松香及/或氫化松香之α,α-支鏈烷羧酸縮水甘油酯組合物。以上縮水甘油酯組合物可例如用作用於油漆或黏著劑之黏合劑組合物中之單體,用作活性稀釋劑或用作除酸劑。本發明亦關於松香及/或氫化松香縮水甘油酯與聚酯多元醇或丙烯酸多元醇或聚醚多元醇之組合之用途。
Description
本發明係關於衍生自與表鹵醇反應之松香(來自不同來源:例如樹膠、松油)或氫化松香之α,α-支鏈烷羧酸縮水甘油酯組合物。本發明中所用之松香由具有通式C
19H
29COOH之二萜類單羧酸構成。該羧酸為三烷基乙酸衍生物且此外具有三環碳架。粗製松香為幾個異構體與兩種或三種不飽和物之摻合物,該松香可經共軛或不經共軛。粗製松香為深棕色固體脆性產物,較淺著色產物係在不飽和物部分或完全氫化之後獲得。三級羧酸與表鹵醇反應以產生與例如新烷酸縮水甘油酯如新壬酸或新癸酸縮水甘油酯相當之縮水甘油酯。本發明與諸如聚酯多元醇之一些聚合物組合給予諸如與經改善硬度、較高玻璃轉移溫度(Tg)、其衍生塗料之較快乾燥不同且出乎意料的效能。
松香衍生物之縮水甘油酯可根據JPS5560575、JPS6469680、JPH03115480、JPH09143430或此項技術中已知之其他縮水甘油化方法獲得。
以上縮水甘油酯組合物可例如用作用於油漆或黏著劑之黏合劑組合物中之單體,用作活性稀釋劑或用作除酸劑。
縮水甘油酯之其他用途為與聚酯多元醇或丙烯酸多元醇或聚醚多元醇或聚醚-酯多元醇之組合或與醇酸樹脂之組合。諸如用於汽車工業塗料中之丙烯酸多元醇與聚酯多元醇之組合的丙烯酸多元醇與聚酯多元醇之組合產生具有有吸引力之塗料特性之快速乾燥塗料體系。塗料組合物可處於有機溶劑應用或基於水之應用或待用於粉末塗料中之固體應用中。可用適當技術將塗料塗覆於金屬、塑膠或木材之上。
以上縮水甘油酯組合物可例如在包含諸如EPIKOTE 828之環氧樹脂之調配物中用作活性稀釋劑。固化劑可為胺、酐或酸,分別如二伸乙基三胺、納迪克甲基酐(nadic methyl anhydride)或環己烷二羧酸。
本發明亦關於用於製備環氧樹脂可固化組合物之方法,該等組合物係藉由將如上文所描述之縮水甘油酯之混合物併入包含環氧樹脂及固化劑之混合物中來獲得。
上文所提及之樹脂可為例如芳族或脂族鹵化或非鹵化縮水甘油醚樹脂。可商購之鹵化樹脂為例如EPON 1163、EPIKOTE 5123、EPIKOTE 5119及EPIKOTE 5112 (來自Hexion之EPON/EPIKOTE)或在樹脂材料上含有超過10重量%溴之任何其他四溴雙酚衍生物縮水甘油醚。非鹵化環氧樹脂之實例為雙酚A及/或雙酚F二縮水甘油醚及/或酚/甲酚-甲醛酚醛清漆聚縮水甘油醚及其類似物。該等樹脂之商業實例為:EPIKOTE 828、EPIKOTE 834、EPIKOTE 1001、EPIKOTE 1002、EPIKOTE 154、EPIKOTE 164。
胺、酐及酸可用作固化劑硬化劑。
上文所提及之胺可為例如脂族胺,諸如二伸乙基三胺(DETA)、三伸乙基四胺(TETA)、四伸乙基五胺(TEPA)、異佛酮二胺(IPD)、對胺基環己烷甲烯(PACM)、二胺基環己烷(DCH)、間二甲苯二胺(mXDA)、4,4'-二胺基3,3'-二甲基二環己基甲烷(DDCM),及諸如基於DETA、TETA、TEPA、IPD、PACM、DCH、mXDA、DDCM之脂族胺之加成物及其類似物;或芳族胺,諸如MDA。
上文所提及之可用作硬化劑之酐可為例如環脂族酐。本文中所揭示之可固化組合物可包括一或多種環脂族酐硬化劑。環脂族酐硬化劑可尤其包括例如納迪克甲基酐、六氫鄰苯二甲酸酐、偏苯三酸酐、十二烯基丁二酸酐、鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐及甲基四氫鄰苯二甲酸酐。酐固化劑亦可包括如US 6,613,839中所描述之苯乙烯與順丁烯二酸酐及其他酐之共聚物。可用於本文中所揭示之可固化組合物之硬化劑亦包括例如衍生自任何上文所提及之酐的酸。
本發明亦關於包含至少一上文所描述之縮水甘油酯之混合物之環氧樹脂可固化組合物,該組合物可用於浸漬適用於複合結構、積層板、塗料、地板及油灰製造應用之纖維。
根據本發明之另一實施例,其中在指定之前,組合物可用於需要高耐化學性之地板應用中。
根據本發明之再另一態樣,該以上組合物為可用於藉由此項技術中已知之技術用玻璃、碳或天然纖維製造複合材料之物質。
根據本發明之再另一態樣,以上縮水甘油酯可(作為除酸劑)與聚酯纖維組合使用以改善擠出期間及後續使用期間之水解穩定性。
如本文中所使用,「松香」(來自不同來源:例如樹膠、松油)或「松香部分」意欲涵蓋松香、松香酸以及為經處理(例如歧化或氫化)松香之松香衍生物。如此項技術中已知,松香為至少八種單羧酸(松脂酸、長葉松酸、去氫松脂酸、新松脂酸、左旋海松脂酸、海松脂酸、山達海松脂酸及異海松脂酸)之摻合物。松脂酸可為主物種且其他七種酸為其異構體。由於松香之組成,故通常使用同義詞「松香酸」來描述各種松香衍生產物。如此項技術中已知,松香部分包括經化學改質之松香,諸如部分或完全氫化松香酸、部分或完全二體化松香酸、官能化松香酸、歧化松香酸、異構化松香酸或其組合。松香可以多種形式商購,例如松香酸、松香酯及二體化松香、氫化松香可例如以產品線Poly-Pale™、Dymerex™、Staybelite-E™、Foral™ Ax-E、Lewisol™及Pentalyn™自Eastman Chemicals商購;以產品線Sylvalite™及Sylvatac™自Arizona Chemicals商購;及以產品線Pensel及Hypal自Arakawa-USA商購。
本發明之另一態樣進一步用松香(松香GE)縮水甘油酯或氫化松香(氫化松香GE)縮水甘油酯之合成來說明。松香或氫化松香之酸官能基之縮水甘油化係根據如技術方案1之方法進行且進一步在實例中加以說明。
該縮水甘油酯可藉由使羧酸之鹼金屬鹽與諸如表鹵醇(例如表氯醇)之經鹵基取代之單環氧化物(1至20莫耳過量)反應來製得。混合物係在形成縮水甘油酯之催化劑加上鹼金屬鹽及水存在之情況下經加熱(50-150℃)。水及過量表鹵醇係藉由共沸蒸餾來移除,且例如NaCl之鹽副產物係藉由過濾及/或洗滌來移除。縮水甘油酯亦可藉由在類似方法條件下使羧酸直接與表氯醇反應來製得。在此反應期間形成之氯醇酯中間物隨後經例如氫氧化鈉或氫氧化鉀之鹼性材料處理,此舉產生所需縮水甘油酯。副產物鹽係藉由洗滌及/或過濾來移除,且水係藉由乾燥來移除。
一種用於製造「松香」或氫化松香縮水甘油酯之方法,其包含
(a)在水及水可混溶溶劑存在之情況下且在量為「松香」酸之莫耳量之至多45 mol%的催化劑存在之情況下,在30℃至110℃範圍內之溫度下,在0.5小時至2.5小時範圍內之時段期間,使松香酸與2-20莫耳過量之諸如表鹵醇(例如表氯醇)之經鹵基取代之單環氧化物反應,
(b)以至多在0.9:1至1.2:1且較佳0.95:1至1.10:1範圍內之如相對於單羧酸基之莫耳比添加額外鹼金屬氫氧化物或鹼金屬烷醇鹽,且在0℃至80℃之溫度下進行反應,
(c)蒸餾所獲得之反應混合物以移除過量經鹵基取代之單環氧化物及溶劑以及所形成之水,及
(d)在視情況用濃鹼金屬氫氧化物或鹼金屬醇鹽水溶液處理殘餘產物之後例如藉由用水洗滌所獲得之縮水甘油酯來移除鹼金屬鹵化物鹽,以便完成去鹵氫(且較佳去氯氫)。
「松香」縮水甘油酯之另一製備為在催化劑存在之情況下使「松香」與含有3至13個碳原子之環氧烷基鹵化物反應,其中
-使大於化學計算量之環氧烷基鹵化物與酸在偶合反應中反應(例如較佳以在1.02:1至1.50:1範圍內之環氧烷基鹵化物與酸之莫耳比),以形成包含鹵醇之中間反應產物,
-在適當地冷卻反應物及/或反應混合物以保持反應混合物之溫度低於80℃之情況下將環氧烷基鹵化物添加至酸中,接著使環氧烷基鹵化物與酸在低於80℃(較佳在55℃至75℃範圍內)之溫度下反應達足以完全轉化該量之酸之時間,
-視情況在閉環反應之前自反應產物移除任何過量之環氧烷基鹵化物,
-使反應產物進行閉環反應(DHC)且視情況進行一或多次後處理(ADHC)以移除任何剩餘鹵基官能基。
- 視情況在DHC之前或之後添加溶劑以降低黏度且以促進在便於移除鹽之水洗滌之後的相分離,
- 視情況使用經降低之反應器壓力且使過量環氧烷基鹵化物回流回至反應器中以進行溫度控制。
待用於本發明方法中之催化劑較佳為不需要溶劑之均相催化劑。催化劑可選自先前技術中已知之催化劑。因此,其可選自鹼金屬氫氧化物、鹼金屬碳酸鹽、鹼土金屬氫氧化物、鹼金屬或鹼土金屬醇鹽或銨鹽,且尤其為式R'R''R'''R''''N
+Y
-氫氧化物或鹵化物,其中R'、R''及R'''可彼此獨立地表示視情況可經一或多個羥基取代之具有1至16個碳原子之烷基,其中R''''表示具有1至16個碳原子之烷基、苯基或苄基,且其中Y表示羥基或諸如氯、溴或碘之鹵素。此外,可使用對應鏻鹽及其芳族型式如碘化乙基三苯鏻。
偶合反應期間之較佳催化劑為銨鹽,且尤其為式R'R''R'''R''''N
+Y
-氫氧化物或鹵化物,其中R'、R''及R'''可彼此獨立地表示具有1至10個碳原子之烷基,且Y表示氯或溴。
如上文所提及,該方法涉及兩個步驟:用於將中間鹵醇轉化成所需縮水甘油酯之偶合反應及閉環反應。
在此項技術中已知之閉環反應中,較佳使用相對強且水溶性金屬氫氧化物或金屬醇鹽。此所謂之DHC反應可藉由添加鹼金屬氫氧化物或鹼金屬烷醇鹽來執行。該反應較佳在50℃至90℃且更佳60℃至80℃之溫度下進行。在閉環反應期間形成之鹽水可經完全或部分移除,接著產物可進行視情況選用之後處理。
可在以上步驟中用於DHC及ADHC之鹼金屬氫氧化物或鹼金屬烷醇鹽較佳選自氫氧化鈉或氫氧化鉀、諸如異丙醇鈉之具有1至6個碳原子之烷醇鈉或醇鉀。最佳使用具有1至6個碳原子之氫氧化鈉或烷醇鈉。
在此等步驟中,氫氧化鈉較佳以15重量%至60重量%且更佳20重量%至50重量%濃度之水溶液形式使用。
自反應產物移除溶劑及水可藉由汽提或蒸餾來進行。應瞭解,若需要,乾燥步驟可在最終洗滌步驟之後進行。
所用方法
用於表徵樹脂之測試方法
使用聚苯乙烯標準品在THF溶液中用凝膠滲透層析儀(Perkin Elmer/Water)量測樹脂之
分子量。在指定溫度下用布氏黏度計(Brookfield viscometer)(LVDV-I)量測樹脂之
黏度。用函數(Ww-Wd) / Ww × 100%計算
固體含量。此處Ww為濕潤樣品之重量,Wd為在110℃溫度下在烘箱中乾燥1小時之後的樣品之重量。
已用來自Perkin Elmer之DSC 7或用來自TA Instruments Thermal Analysis之設備測定
Tg(玻璃轉移溫度)。掃描速率分別為20℃/min及10℃/min。僅比較在相同實驗條件下獲得之資料。若非此舉,則因不同掃描速率存在之溫度差已經證明對於所比較之結果而言不重要。
黃度值使用來自Hach Lange之Lico 500依鉑-鈷標度(Platinum-Cobalt scale)獲得之量測結果。
用於表徵塗料之方法 適用期藉由觀測在通常為24.0 ± 0.5℃之室溫下加倍初始黏度之經過時間來測定適用期。
透明塗料之塗覆使用Q面板作為基板。隨後,藉由快速蒸發溶劑甲基乙酮或丙酮來清潔面板。
無塵時間藉由使棉絨球從經界定距離豎直掉落在扁平基板上來評估透明塗料之無塵時間(DFT)。當棉球與基板接觸時,立即翻轉基板。無塵時間定義為棉絨球不再黏附至基板之時間間隔。
硬度發展用柯尼希方法(Koenig method)使用擺式硬度試驗機來追蹤硬度發展。
所用化學品-
松香:可獲自
Sigma - Aldrich-
氫化松香:可獲自
Foreverest-
松香縮水甘油酯:根據如技術方案1至2之方法合成
-
氫化松香縮水甘油酯:根據如技術方案1至2之方法合成
-
Cardura™ E10P :可獲自Hexion
-
Cardura™ 9 :可獲自Hexion
-
乙二醇:來自Aldrich
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單新戊四醇:可獲自Sigma-Aldrich
-
甲基六氫鄰苯二甲酸酐:可獲自Sigma-Aldrich
-
丙烯酸:可獲自Sigma-Aldrich
-
甲基丙烯酸:可獲自Sigma-Aldrich
-
甲基丙烯酸羥乙酯:可獲自Sigma-Aldrich
-
苯乙烯:可獲自Sigma-Aldrich
-
丙烯酸 2 - 乙基己酯:可獲自Sigma-Aldrich
-
甲基丙烯酸甲酯:可獲自Sigma-Aldrich
-
丙烯酸丁酯:可獲自Sigma-Aldrich
-
甲基丙烯酸異莰酯:可獲自Sigma-Aldrich
-
二甲苯-
二第三戊基過氧化物為來自Arkema之Luperox DTA
-
過氧 - 3 , 5 , 5 - 三甲基己酸第三丁酯:可獲自Akzo Nobel
-
乙酸正丁酯來自Aldrich
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二氯甲烷來自Biosolve
-
稀釋劑 (thinner) A :為50 wt%二甲苯、30 wt%甲苯、10 wt%芳烴混合物溶劑A (Shellsol A)、10 wt%乙酸2-乙氧基乙酯之混合物。
-
稀釋劑 B :為乙酸丁酯
-
固化劑 , HDI :1,6-己二異氰酸酯三聚體,來自Bayer Material Science或Covestro之Desmodur N3390 BA或來自Perstorp之Tolonate HDT LV2
-
調平劑 :作為在乙酸丁酯中稀釋為10%之BYK-331之『10 wt% BYK』
-
催化劑 :作為在乙酸丁酯中稀釋為1 wt%之二月桂酸二丁基錫之『1 wt% DBTDL』
-
顏料分散劑:來自BYK之Disperbyk 110
-
油漆表面調平劑:來自BYK之BYK 358N
-
消泡劑:來自BYK之BYK 077
-
沈降控制:來自Lubrizol之Solthix 250
-
氧化鈦顏料 :來自The Chemours Company之Ti-Pure TS6200
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油漆調配物稀釋劑 :來自Sigma-Aldrich之乙氧基丙酸乙酯、來自Sigma-Aldrich之甲基戊酮
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HALS 添加劑:來自BASF之Tinuvin 123
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UVA 添加劑:來自BASF之Tinuvin 1130
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油漆固化劑:來自Covestro之Desmodur N3300
松香及氫化松香縮水甘油酯之合成實例 實例 1 :
將750公克氫化樹膠松香、321公克甲苯及21.8公克(0.04 mol/mol氫化樹膠松香)氯化四甲銨(呈50%水溶液形式)裝入反應器中且加熱至70℃;
將表氯醇給予至反應器中,同時將反應介質冷卻至約70℃,保持低添加速率以允許適當冷卻;經約90分鐘之時段添加總計253公克表氯醇(1.1 mol/mol氫化樹膠松香)。因此,添加時間為冷卻效率之函數。監測反應且在當前條件下此舉耗費約7小時。
在70℃下在苛性鹼存在之情況下執行閉環反應;使用總計246 g 50% NaOH (1.24 mol/mol氫化樹膠松香)。在90分鐘內使用線性輪廓給予NaOH。210分鐘後反應時間之後,閉環反應完成。再添加1375公克甲苯及653公克水以洗掉鹽。相分離之後移除鹽水相,接著進行最終水洗滌。藉由在減壓下進行汽提來將甲苯自產物中移除。
對產物EGC加以分析且發現其為2567 mmol/kg;加德納顏色(Colour Gardner)(50%於甲苯中)為1。
黏合劑製備及調配物實例 比較實例 1
將以下組分裝入配備有攪拌器、冷凝器及溫度計之反應容器中:92.4公克Cardura™ E10P、24.0公克乙酸丁酯。已將彼初始反應器裝料加熱至135℃。隨後,經1 h 20 min之時段添加以下混合物,同時保持溫度恆定:27.5公克丙烯酸、1.2公克二第三戊基過氧化物、12.0公克乙酸正丁酯。進一步添加1.2公克二第三戊基過氧化物及20.4公克乙酸正丁酯之後,在135℃下進行後蒸煮1 h。
實例 2a將以下組分裝入配備有攪拌器、冷凝器及溫度計之反應容器中:92.4公克松香GE、24.0公克乙酸丁酯。已將彼初始反應器裝料加熱至135℃。隨後,經1 h 18 min之時段添加以下混合物,同時保持溫度恆定:16.7公克丙烯酸、1.2公克二第三戊基過氧化物、12.0公克乙酸正丁酯。進一步添加1.2公克二第三戊基過氧化物及20.4公克乙酸正丁酯之後,在135℃下進行後蒸煮1 h。
實例 2b將以下組分裝入配備有攪拌器、冷凝器及溫度計之反應容器中:92.4公克氫化松香GE、24.0公克乙酸丁酯。已將彼初始反應器裝料加熱至135℃。隨後,經1 h 18 min之時段添加以下混合物,同時保持溫度恆定:16.8公克丙烯酸、1.2公克二第三戊基過氧化物、12.0公克乙酸正丁酯。進一步添加1.2公克二第三戊基過氧化物及20.4公克乙酸正丁酯之後,在135℃下進行後蒸煮1 h。
觀測結果:丙烯酸多元醇之Tg受縮水甘油酯之選擇影響。
實例 3松香GE或氫化松香GE與丙烯酸之加成物(ACE加成物)及與甲基丙烯酸之加成物(MACE加成物) (參見表3)為可用於調配羥基官能(甲基)丙烯酸聚合物之丙烯酸單體。
表 3:以重量份為單位之加成物組成之納入量
● 將DABCO T9及4-甲氧基酚(185 ppm,基於縮水甘油酯重量計算)裝入反應器中。
● 在氣流下執行反應(以便使自由基抑制劑再循環)。
● 將反應器裝料在持續攪拌下緩慢加熱至約80℃,其中放熱反應開始,從而將溫度升高至約100℃。
● 維持100℃之溫度,直至達到低於30 meq/kg之環氧基含量。將反應混合物冷卻至室溫。
實例 4丙烯酸樹脂
松香GE丙烯酸加成物 | 松香GE甲基丙烯酸加成物 | 氫化松香GE丙烯酸加成物 | 氫化松香GE甲基丙烯酸加成物 | |
初始反應器裝料 | ||||
松香GE 氫化松香GE | 250 | 250 | 250 | 250 |
丙烯酸 | 51.0 | 51.4 | ||
甲基丙烯酸 | 62.5 | 63.0 | ||
自由基抑制劑 | ||||
4-甲氧基酚 | 0.463 | 0.463 | 0.463 | 0.463 |
催化劑 | ||||
DABCO T9 (以縮水甘油酯計0.07 wt%) | 0.175 | 0.175 | 0.175 | 0.175 |
對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表4)加熱至140℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約75%之固體含量。
表 4 :丙烯酸樹脂配方
實例 | 實例4a | 實例4b | 實例4c | 實例4d |
初始反應器裝料 | 重量% | 重量% | 重量% | 重量% |
Cardura™ E10P | 25.0 | 0 | 20.0 | 25.0 |
松香GE | 0 | 0 | 5.0 | 0 |
氫化松香GE | 0 | 25.0 | 0 | 0 |
乙酸丁酯 | 14.0 | 14.0 | 14.0 | 14.0 |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 | 0.5 |
饋料材料 | 重量% | 重量% | 重量% | 重量% |
甲基丙烯酸 | 9.9 | 5.4 | 9.2 | 9.9 |
甲基丙烯酸羥乙酯 | 10.0 | 16.0 | 10.8 | 9.5 |
苯乙烯 | 20.0 | 20.0 | 20.0 | 20.0 |
甲基丙烯酸甲酯 | 14.0 | 12.6 | 13.9 | 0 |
甲基丙烯酸異莰酯 | 0 | 0 | 0 | 30.6 |
丙烯酸丁酯 | 21.1 | 20.0 | 21.1 | 5.0 |
二第三戊基過氧化物 | 6.5 | 6.5 | 6.5 | 6.5 |
後蒸煮 | 重量% | 重量% | 重量% | 重量% |
二第三戊基過氧化物 | 1.0 | 1.0 | 1.0 | 1.0 |
130℃下添加之溶劑 | 重量% | 重量% | 重量% | 重量% |
乙酸丁酯 | 18.0 | 18.0 | 18.0 | 18.0 |
最終固體含量 | 75.2% | 75.6% | 75.0% | 76.2% |
羥基含量 | 3.1% | 3.2% | 3.0% | 3.0% |
顏色(Pt/Co) | 15 | 42 | 238 | 64 |
隨後,用以下成分調配透明塗料(表5)且藉由80 µm濕潤塗棒來塗覆透明塗料:
表 5:透明塗料調配物
實例ex 4(a-d)之樹脂 | Tolonate HDT | 10 wt% BYK於ButAc中 | 1 wt% DBTDL於ButAc中 | 乙酸丁酯 |
60.0 g | 16.3 g | 0.44 g | 2.26 g | 稀釋直至黏度為40-55 mPa.s |
比較特性示於表6中。
表 6 :透明塗料之特性
實例之透明塗料 | 實例4a | 實例4b | 實例4c | 實例4d |
VOC (g/l) | 418 | 448 | 404 | 441 |
初始黏度(mPa.s) | 53.1 | 54.9 | 51.3 | 43.6 |
無塵時間(min) | 16.5 | 9.5 | 8.5 | 10.0 |
6小時柯尼希硬度(sec) | 3 | 8 | 6 | 7 |
丙烯酸樹脂
對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表7)加熱至150℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在150℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約70%之固體含量。
表 7 :丙烯酸樹脂配方
實例 | 實例4f | 實例4g | 實例4h | 實例4i |
初始反應器裝料 | 重量% | 重量% | 重量% | 重量% |
Cardura™ E10P | 25.0 | 0 | 15.0 | 0 |
Cardura™ 9 | 0 | 25.0 | 0 | 0 |
松香GE | 0 | 0 | 10.0 | 0 |
氫化松香GE | 0 | 0 | 0 | 25.0 |
乙酸丁酯 | 5.0 | 5.0 | 5.0 | 5.0 |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 | 0.5 |
饋料材料 | 重量% | 重量% | 重量% | 重量% |
甲基丙烯酸 | 9.8 | 10.3 | 8.4 | 6.3 |
甲基丙烯酸羥乙酯 | 16.4 | 16.4 | 19.3 | 22.5 |
苯乙烯 | 20.0 | 20.0 | 20.0 | 20.0 |
甲基丙烯酸甲酯 | 12.0 | 12.6 | 12.0 | 12.0 |
丙烯酸丁酯 | 16.8 | 16.3 | 15.3 | 14.2 |
二第三戊基過氧化物 | 5.0 | 5.0 | 5.0 | 5.0 |
後蒸煮 | 重量% | 重量% | 重量% | 重量% |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 | 0.5 |
130℃下添加之溶劑 | 重量% | 重量% | 重量% | 重量% |
乙酸丁酯 | 35.0 | 35.0 | 35.0 | 35.0 |
最終固體含量 | 70.8% | 70.2% | 72.1% | 72.2% |
羥基含量 | 3.9% | 4.0% | 4.0% | 4.0% |
隨後,用以下成分調配透明塗料(表8)且藉由80 µm濕潤塗棒來塗覆透明塗料:
表 8 :透明塗料調配物
實例ex 4之樹脂 | Tolonate HDT | 10 wt% BYK於ButAc中 | 1 wt% DBTDL於ButAc中 | 乙酸丁酯 |
60.0 g | 19.5 g | 0.44 g | 2.28 g | 稀釋直至黏度為40-55 mPa.s |
比較特性示於表9中。
表 9 :透明塗料之特性
實例之透明塗料 | 實例4f | 實例4g | 實例4h | 實例4i |
VOC (g/l) | 427 | 428 | 472 | 474 |
初始黏度(mPa.s) | 54.9 | 55.5 | 53.4 | 55.8 |
無塵時間(min) | 14.0 | 13.0 | 9.0 | 7.5 |
6小時柯尼希硬度 (sec) | 7 | 8 | 12 | 12 |
丙烯酸樹脂
對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表10)加熱至140℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約75%之固體含量。
表 10 :丙烯酸樹脂配方
實例 | 實例4k | 實例4l | 實例4m | 實例4n |
初始反應器裝料 | 重量% | 重量% | 重量% | 重量% |
Cardura™ E10P | 25.0 | 25.0 | 15.0 | 0 |
松香GE | 0 | 0 | 10.0 | 0 |
氫化松香GE | 0 | 0 | 0 | 25.0 |
乙酸丁酯 | 14.0 | 14.0 | 14.0 | 14.0 |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 | 0.5 |
饋料材料 | 重量% | 重量% | 重量% | 重量% |
Cardura™ E10P | 0 | 0 | 0 | 0 |
甲基丙烯酸 | 9.9 | 9.9 | 8.4 | 6.3 |
甲基丙烯酸羥乙酯 | 17.1 | 17.1 | 19.3 | 22.5 |
苯乙烯 | 20.0 | 20.0 | 20.0 | 20.0 |
甲基丙烯酸甲酯 | 20.0 | 0 | 20.0 | 20.0 |
甲基丙烯酸異莰酯 | 0 | 28.0 | 0 | 0 |
丙烯酸丁酯 | 8.0 | 0.0 | 7.3 | 6.2 |
二第三戊基過氧化物 | 6.5 | 6.5 | 6.5 | 6.5 |
後蒸煮 | 重量% | 重量% | 重量% | 重量% |
二第三戊基過氧化物 | 1.0 | 1.0 | 1.0 | 1.0 |
130℃下添加之溶劑 | 重量% | 重量% | 重量% | 重量% |
乙酸丁酯 | 27.0 | 27.0 | 27.0 | 27.0 |
最終固體含量 | 69.7% | 70.2% | 71.5% | 71.7% |
羥基含量 | 4.0% | 4.0% | 4.0% | 4.0% |
顏色(Pt/Co) | 17 | 19 | 273 | 39 |
隨後,用以下成分調配透明塗料(表11)且藉由80 µm濕潤塗棒來塗覆透明塗料:
表 11 :透明塗料調配物
實例ex 4之樹脂 | Tolonate HDT | 10 wt% BYK於ButAc中 | 1 wt% DBTDL於ButAc中 | 乙酸丁酯 |
60.0 g | 19.7 g | 0.44 g | 2.27 g | 稀釋直至黏度為40-55 mPa.s |
比較特性示於表12中。
表 12 :透明塗料之特性
實例之透明塗料 | 實例4k | 實例4l | 實例4m | 實例4n |
VOC (g/l) | 424 | 406 | 449 | 429 |
初始黏度(mPa.s) | 51.6 | 51.0 | 51.0 | 53.4 |
無塵時間(min) | 12.5 | 9.5 | 9.0 | 7.0 |
6小時柯尼希硬度(sec) | 7 | 13 | 14 | 14 |
實例 5用於汽車修補漆之透明塗料
摻合溶劑以產生具有以下組成之稀釋劑混合物(表13):
表 13 :稀釋劑組成
稀釋劑 | 於溶劑摻合物中之理論重量% |
甲苯 | 30.1% |
芳烴混合物溶劑A | 34.9% |
乙酸2-乙氧基乙酯 | 10.0% |
乙酸正丁酯 | 25.0% |
總計 | 100% |
隨後,用以下成分(重量份)調配透明塗料(表14):
表 14 :透明塗料調配物
實例ex 4之樹脂 | Desmodur N3390 | 10 wt% BYK於ButAc中 | 1 wt% DBTDL於ButAc中 | 稀釋劑 |
60.0 g | 19.5 g | 0.44 g | 2.28 g | 稀釋直至黏度為40-55 mPa.s |
此等透明塗料可藉由噴霧來塗覆。
著色2K聚胺甲酸酯
相同類型之樹脂亦可用於工業應用之著色體系中。以下給出白色油漆調配物之實例:
表 15 :著色油漆調配物之實例
成分 | 納入量 (以公克為單位之份數) |
部分A 來自實例4之丙烯酸聚合物(70%固體) | 31.6 |
Disperbyk 110 | 2.5 |
BYK 358N BYK 077 | 2.3 2.3 |
Solthix 250 | 4.5 |
Ti-Pure TS-6200 | 143.3 |
乙氧基丙酸乙酯 | 用於在高速攪動下獲得滾動環狀物 |
釋放物 來自實例4之丙烯酸聚合物(70%固體) | 151.3 |
Tinuvin 123 | 3.2 |
Tinuvin 1130 | 4.1 |
乙氧基丙酸乙酯 | 35.3 |
甲基戊酮 | 14.2 |
二月桂酸二丁基錫 | 0.07 |
部分B N3300 (1.1:1 NCO:OH比) | 76.7 |
實例6
用於中級固體初次修補漆透明塗料之基於松香GE或氫化松香GE之丙烯酸聚合物
對用於丙烯酸多元醇之反應器進行氮氣沖氣,且將初始反應器裝料(參見表16)加熱至140℃。在此溫度下經5小時經由泵將包括引發劑之單體混合物添加至反應器中。在一小時期間將額外引發劑饋料至反應器中,且隨後將混合物保持在140℃下以完成後反應中之轉化。最後,將聚合物冷卻且用乙酸丁酯稀釋至約60%之固體含量。
表 16 :丙烯酸樹脂配方
重量% | |
初始反應器裝料 | |
松香GE或氫化松香GE | 25.0 |
二甲苯 | 24.8 |
單體混合物 | |
丙烯酸 | 6.4 |
甲基丙烯酸丁酯 | 12.9 |
丙烯酸丁酯 | 8.2 |
甲基丙烯酸羥乙酯 | 10.6 |
苯乙烯 | 30.0 |
甲基丙烯酸甲酯 | 7.9 |
引發劑 | |
二第三戊基過氧化物(DTAP) | 1.5 |
後添加 | |
二第三戊基過氧化物 | 1.0 |
溶劑(用於稀釋至60%固體) | |
乙酸丁酯 | 41.3 |
透明漆調配物
藉由添加Cymel 1158 (來自CYTEC之固化劑)及用於稀釋至噴霧黏度之溶劑來由丙烯酸聚合物調配透明漆(參見表17)。聚合物之酸度足以催化固化過程,因此不添加額外酸催化劑。充分攪拌該漆以獲得均相組合物。
表 17 :透明漆調配物
成分 | 納入量 (重量份) |
丙烯酸聚合物 | 60.0 |
Cymel 1158 | 8.8 |
乙酸丁酯 | 達到塗覆黏度 |
塗覆及固化
將塗料用棒塗機塗覆在Q面板上以達成約40 µm之乾膜厚度。將體系在室溫下晾乾15分鐘,隨後在140℃下烘烤30分鐘。在23℃下在1天後對經固化體系進行測試。
實例 7對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表18)加熱至140℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約75%之固體含量。
表 18 :丙烯酸樹脂配方
實例 | 實例7a | 實例7b | 實例7c |
初始反應器裝料 | 重量% | 重量% | 重量% |
Cardura™ E10P | 15.0 | 0 | 0 |
松香GE | 0 | 15.0 | 0 |
氫化松香GE | 0 | 0 | 15.0 |
乙酸丁酯 | 14.0 | 14.0 | 14.0 |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 |
饋料材料 | 重量% | 重量% | 重量% |
Cardura™ E10P | 10.0 | 0 | 0 |
松香GE | 0 | 10.0 | 0 |
氫化松香GE | 0 | 0 | 10.0 |
甲基丙烯酸 | 9.9 | 5.4 | 5.4 |
甲基丙烯酸羥乙酯 | 10.0 | 16.0 | 16.0 |
苯乙烯 | 20.0 | 20.0 | 20.0 |
甲基丙烯酸甲酯 | 14.0 | 12.6 | 12.6 |
丙烯酸丁酯 | 21.1 | 20.0 | 20.0 |
二第三戊基過氧化物 | 6.5 | 6.5 | 6.5 |
後蒸煮 | 重量% | 重量% | 重量% |
二第三戊基過氧化物 | 1.0 | 1.0 | 1.0 |
130℃下添加之溶劑 | 重量% | 重量% | 重量% |
乙酸丁酯 | 18.0 | 18.0 | 18.0 |
最終固體含量 | 75.0% | 75.0% | 75.0% |
羥基含量 | 3.1% | 3.1% | 3.2% |
實例 8藉由加成聚合獲得之聚酯
將三羥甲基丙烷、甲基六氫鄰苯二甲酸酐或丁二酸酐及乙酸正丁酯裝入反應容器中且在乙酸丁酯沸騰下加熱直至完全轉化。隨後,逐滴添加Cardura E10P或松香GE或氫化松香GE,且在150℃下進行反應直至達到可接受之酸值。聚酯具有約80.0 wt%之固體含量。配方及特性定義於表19中。
表 19 :聚酯多元醇配方
實例 | 實例8a | 實例8b | 實例8c | 實例8d | 實例8e |
初始反應器裝料 | 重量% | 重量% | 重量% | 重量% | 重量% |
三羥甲基丙烷 | 14.2 | 10.8 | 10.8 | 13.5 | 11.7 |
甲基六氫鄰苯二甲酸酐 | 36.0 | 27.4 | 27.2 | 34.1 | 0 |
丁二酸酐 | 0 | 0 | 0 | 0 | 26.2 |
乙酸丁酯 | 25.0 | 25.0 | 25.0 | 25.0 | 25.0 |
饋料材料 | 重量% | 重量% | 重量% | 重量% | 重量% |
Cardura™ E10P | 49.8 | 0 | 0 | 39.2 | 62.1 |
松香GE | 0 | 0 | 62.0 | 13.2 | 0 |
氫化松香GE | 0 | 61.8 | 0 | 0 | 0 |
最終固體含量 | 81.3% | 79.7% | 80.3% | 83.3% | 81.3% |
羥基含量 | 5.3% | 4.0% | 4.0% | 5.1% | 4.4% |
酸值(mg KOH/g) | 7.0 | 5.6 | 6.4 | 7.1 | 4.7 |
實例8之樹脂可經調配於具有低VOC (揮發性有機化合物)含量且提供極佳外觀以及高乾燥速度之諸如2K (聚胺甲酸酯)的塗料組合物中。
藉由聚縮合獲得之聚酯
表20中描述之相同類型之聚酯亦可藉由使用多官能酸而非酐來製備。酸官能基與羥基之反應係在約200-240℃之溫度下執行直至在如二甲苯之共沸溶劑存在之情況下充分轉化以移除過程期間生成之水。
實例 9實例8之樹脂可與丙烯酸多元醇摻合以便獲得用於例如汽車塗料之適合樹脂。丙烯酸樹脂之實例在表19中給出。
對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表20)加熱至140℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約75%之固體含量。
表 20 :用於摻合之丙烯酸多元醇之實例
實例 | 實例9 |
初始反應器裝料 | 重量% |
Cardura™ E10P | 25.0 |
乙酸丁酯 | 14.0 |
二第三戊基過氧化物 | 0.5 |
饋料材料 | 重量% |
甲基丙烯酸 | 9.9 |
甲基丙烯酸羥乙酯 | 10.0 |
苯乙烯 | 20.0 |
甲基丙烯酸甲酯 | 14.0 |
甲基丙烯酸異莰酯 | 0 |
丙烯酸丁酯 | 21.1 |
二第三戊基過氧化物 | 6.5 |
後蒸煮 | 重量% |
二第三戊基過氧化物 | 1.0 |
130℃下添加之溶劑 | 重量% |
乙酸丁酯 | 18.0 |
最終固體含量 | 75.2% |
羥基含量 | 3.1% |
隨後,將丙烯酸多元醇與來自實例8之聚酯多元醇以25 wt%聚酯多元醇與75 wt%丙烯酸多元醇之含量摻合。使用該摻合物以調配透明塗料(表21)且藉由80 µm濕潤塗棒來塗覆透明塗料:
表 21 :丙烯酸多元醇與聚酯多元醇之摻合
75/25摻合物 | Tolonate HDT | 10 wt% BYK於ButAc中 | 1 wt% DBTDL於ButAc中 | 乙酸丁酯 |
60.0 g | 17.9 - 19.9 g 適於OH % | 0.45 g | 2.3 g | 稀釋直至黏度為40-55 mPa.s |
比較特性示於表22中。
表 22 :透明塗料之特性
實例之透明塗料 | 實例9a | 實例9b | 實例9c | 實例9d | 實例9e |
VOC (g/l) | 384 | 383 | 392 | 386 | 381 |
初始黏度(mPa.s) | 53.7 | 54.3 | 52.8 | 54.6 | 52.8 |
無塵時間(min) | 44.0 | 17.5 | 15.0 | 26.0 | 46.5 |
6小時柯尼希硬度(sec) | 1 | 7 | 7 | 3 | 3 |
實例 10來自實例8及實例9之丙烯酸多元醇及聚酯多元醇可在混合過程中在同一反應器中製備。首先合成聚酯多元醇,且將其用作初始反應器裝料以在同一反應期間繼續製備丙烯酸多元醇。該過程之實例與用於聚酯多元醇中之Cardura E10P一起描述於表23中,但亦可在製備中使用松香GE或氫化松香GE。
將三羥甲基丙烷、甲基六氫鄰苯二甲酸酐及乙酸正丁酯裝入反應容器中且在乙酸丁酯沸騰下加熱直至完全轉化。隨後,逐滴添加Cardura E10P或松香GE或氫化松香GE,且在150℃下再進行反應一小時以完成酸轉化。接著,將反應器內部溫度降至140℃,且隨後在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。隨後,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。最後,將聚合物冷卻至135℃且用乙酸丁酯稀釋至約75%之固體含量。
表 23 :基於聚酯之丙烯酸多元醇蒸煮(混合過程)
實例 10a | 實例 10b | 實例 10c | |
1°/聚酯蒸煮,以重量%為單位之組分 | |||
三羥甲基丙烷 | 3.5 | 2.7 | 2.7 |
甲基六氫鄰苯二甲酸酐 | 9.0 | 6.8 | 6.8 |
乙酸正丁酯 | 5.0 | 5.0 | 5.0 |
Cardura E10P | 12.5 | 15.5 | 15.5 |
2°/丙烯酸多元醇蒸煮,以重量%為單位之初始反應器裝料 | |||
Cardura E10P | 18.8 | 0 | 0 |
松香GE | 0 | 0 | 18.8 |
氫化松香GE | 0 | 18.8 | 0 |
乙酸丁酯 | 10.0 | 10.0 | 10.0 |
3°/丙烯酸多元醇蒸煮,以重量%為單位之饋料材料 | |||
甲基丙烯酸 | 7.0 | 4.8 | 4.8 |
甲基丙烯酸羥乙酯 | 9.8 | 12.0 | 12.0 |
苯乙烯 | 15.0 | 15.0 | 15.0 |
丙烯酸丁酯 | 15.0 | 15.0 | 15.0 |
甲基丙烯酸甲酯 | 9.4 | 9.4 | 9.4 |
二第三戊基過氧化物 | 5.3 | 5.3 | 5.3 |
4°/丙烯酸多元醇後蒸煮,以重量%為單位之饋料材料 | |||
二第三戊基過氧化物 | 0.75 | 0.75 | 0.75 |
5°/丙烯酸多元醇固體含量調節,以重量%為單位之所添加之溶劑 | |||
乙酸正丁酯 | 17.0 | 17.0 | 17.0 |
當應用於塗料時,觀測到利用該混合過程組合松香GE或氫化松香GE顯著地改善VOC (揮發性有機化合物)及早期乾燥發展。
實例 11藉由將以下組分裝入反應容器中來獲得聚醚:2.5500公克松香GE、1.1571公克二氯甲烷、0.0137公克三氟化硼合二乙醚。反應在室溫下進行3天且隨後藉由蒸發徹底移除溶劑。
實例 12藉由將以下組分裝入反應容器中來獲得聚醚:2.5500公克氫化松香GE、1.1571公克二氯甲烷、0.0137公克三氟化硼合二乙醚。反應在室溫下進行3天且隨後藉由蒸發徹底移除溶劑。
比較實例 13藉由將以下組分裝入反應容器中來獲得聚醚:2.5500公克Cardura E10P、1.1571公克二氯甲烷、0.0137公克三氟化硼合二乙醚。反應在室溫下進行3天且隨後藉由蒸發徹底移除溶劑。
觀測 結果:經改質聚醚樹脂之Tg受縮水甘油酯之類型的組成影響,基於松香之縮水甘油酯給出較高Tg。
實例 14聚醚樹脂
將以下組分裝入配備有攪拌器、溫度計及冷凝器之反應容器中:138公克二三羥甲基丙烷(DTMP)、862公克松香GE、135.5公克乙酸正丁酯(BAC)及2.5公克辛酸錫2。將混合物加熱至其約180℃之回流溫度約4小時直至松香GE經轉化達到低於0.12 mg/g之環氧基含量。冷卻之後,聚醚具有約88%之固體含量。
實例 15聚醚樹脂
將以下組分裝入配備有攪拌器、溫度計及冷凝器之反應容器中:139公克二三羥甲基丙烷(DTMP)、861公克氫化松香GE、135.5公克乙酸正丁酯(BAC)及2.5公克辛酸錫2。將混合物加熱至其約180℃之回流溫度約4小時直至氫化松香GE經轉化達到低於0.12 mg/g之環氧基含量。冷卻之後,聚醚具有約88%之固體含量。
比較實例 16聚醚樹脂
將以下組分裝入配備有攪拌器、溫度計及冷凝器之反應容器中:123公克單新戊四醇、877公克Cardura E10P、194公克乙酸正丁酯及3.552公克2-乙基己酸錫(II)。將混合物加熱至約180℃之溫度約6小時直至Cardura E10P經轉化達到約25 mmol/kg之環氧基含量。冷卻之後,聚醚具有約95%之固體含量。
實例 17聚醚樹脂
將以下組分裝入配備有攪拌器、溫度計及冷凝器之反應容器中:79公克單新戊四醇、921公克松香GE、183公克乙酸正丁酯及0.3550公克2-乙基己酸錫(II)。將混合物加熱至約180℃之溫度約6小時直至松香GE經轉化達到約25 mmol/kg之環氧基含量。冷卻之後,聚醚具有約95%之固體含量。
實例 18聚醚樹脂
將以下組分裝入配備有攪拌器、溫度計及冷凝器之反應容器中:79公克單新戊四醇、921公克氫化松香GE、185公克乙酸正丁酯及3.572公克2-乙基己酸錫(II)。將混合物加熱至約180℃之溫度約6小時直至氫化松香GE經轉化達到約25 mmol/kg之環氧基含量。冷卻之後,聚醚具有約95%之固體含量。
觀測結果:當以松香GE或氫化松香GE置換Cardura E10P以進行聚醚蒸煮時觀測到顯著改善(更快硬度發展)。
實例 19製備用於複合結構之真空灌注物
用於諸如遊艇及風力機之大型結構之真空灌注物之樹脂係藉由混合此處所描述之27.7重量份固化劑摻合物及100重量份環氧樹脂摻合物來製備:
環氧樹脂摻合物:850重量份Epikote 828及150重量份松香GE或氫化松香GE。
固化劑摻合物:650重量份Jeffamine D230及350重量份異佛酮二胺(IPDA)。
Jeffamine D230為可獲自Huntsman Corporation之聚氧伸烷基胺。Epikote 828為可獲自Hexion Chemicals之環氧樹脂。
實例 20可鏝塗地板及修補化合物之實例
混合下表24中所呈現之成分以製備可鏝塗地板化合物:
表 24:可鏝塗地板化合物之製備
基礎組分 | 重量(份) | 體積(份) | 供應商 |
EPIKOTE 828LVEL 松香GE或氫化松香GE | 63.2 11.1 | 126.3 22.3 | Hexion |
Byk A530 | 4.8 | 13.4 | Byk Chemie |
填料添加之前將添加劑混合至 EPIKOTE 樹脂中 | |||
總計 | 79.1 | 162.0 | |
填料 | 重量(份) | 體積(份) | 供應商 |
1-2 mm砂 | 582.3 | 496.4 | SCR Sibelco |
0.2-0.6 mm砂 | 298.4 | 254.4 | SCR Sibelco |
總計 | 880.7 | 750.8 | |
使用混凝土混合器分散至基礎組分中 | |||
固化劑組分 | 重量(份) | 體積(份) | 供應商 |
EPIKURE F205 | 40.2 | 87.2 | Hexion |
總計 | 40.2 | 87.2 | |
塗覆之前將固化劑與 EPIKOTE 樹脂基質及填料充分混合 | |||
總調配物 | 1000.0 | 1000.0 |
實例 21用於基於水之自調平地板之調配物
混合下表25中所呈現之成分以製備基於水之自調平地板體系:
表 25:基於水之自調平地板體系之製備
固化劑組分(A) | 重量(份) | 供應商 | 說明 | ||
EPIKURE 8545-W-52 (HEW = 320 g/eq) | 164.00 | Hexion | |||
EPIKURE 3253 | 4.00 | Hexion | 加速劑 | ||
BYK 045 | 5.00 | BYK CHEMIE | 消泡劑 | ||
Antiterra 250 | 4.00 | BYK CHEMIE | 分散 | ||
Byketol WS | 5.00 | BYK CHEMIE | 濕潤劑 | ||
Bentone EW(3%於水中) | 20.00 | Elementis | 抗沈降 | ||
填料添加之前將添加劑混合至 EPIKURE 固化劑中 | |||||
二氧化鈦2056 | 50.00 | KronosTitan | |||
在 2000 rpm 下分散顏料 10 分鐘。 | |||||
EWO-重晶石 | 195.00 | Sachtleben Chemie | 硫酸鋇 | ||
石英粉末W8 | 98.00 | Westdeutsche Quarzwerke | |||
在 2000 rpm 下分散填料 10 分鐘 | |||||
水 | 55.00 | ||||
0.1-0.4 mm砂 | 400.00 | Euroquarz | |||
組分A總計 | 1000.00 | ||||
樹脂組分(B) | |||||
EPIKOTE 828LVEL | 81.00 | Hexion | |||
GE9H | 19.00 | ||||
將(B)混合至(A)中 | |||||
調配物A+B總計 | 1081.00 | ||||
調配物特徵 | |||||
填料+顏料/黏合劑比率 | 3.9 | 以重量計 | |||
PVC | 37.7 | % v/v | |||
密度 | 1.9 | g/ml | |||
水含量 | 12.5 | % m/m | |||
實例 22經由二級分散獲得之基於水之丙烯酸多元醇之製備。
對配備有攪拌器之玻璃反應器進行氮氣沖氣,且將初始反應器裝料(參見表26)加熱至140℃。隨後,在此溫度下經5小時經由泵將包括引發劑之單體混合物逐漸添加至反應器中。接著,在140℃下在另一1小時時段期間將額外引發劑饋料至反應器中。隨後,將聚合物冷卻至80℃,且添加n,n-二甲基乙醇胺且使其在劇烈攪拌下反應15分鐘。在反應器中逐漸添加80℃下之預加熱水2小時且將溫度維持在80℃下。隨後,在室溫下冷卻水性樹脂且排出。
表 26 :水性丙烯酸多元醇配方
實例 | 實例22a | 實例22b | 實例22c |
初始反應器裝料 | 重量% | 重量% | 重量% |
Cardura™ E10P | 30.0 | 0 | 0 |
松香GE | 0 | 30.0 | 0 |
氫化松香GE | 0 | 0 | 30.0 |
丁氧乙醇 | 10.0 | 10.0 | 10.0 |
饋料材料 | 重量% | 重量% | 重量% |
丙烯酸 | 12.9 | 9.4 | 9.4 |
甲基丙烯酸羥乙酯 | 14.0 | 17.5 | 17.5 |
苯乙烯 | 20.0 | 20.0 | 20.0 |
甲基丙烯酸甲酯 | 14.1 | 14.1 | 14.1 |
丙烯酸丁酯 | 9.0 | 9.0 | 9.0 |
二第三戊基過氧化物 | 2.5 | 2.5 | 2.5 |
後蒸煮 | 重量% | 重量% | 重量% |
二第三戊基過氧化物 | 0.5 | 0.5 | 0.5 |
最終固體含量 | 91% | 91% | 91% |
羥基含量 | 4.0% | 3.6% | 3.6% |
酸值(mg KOH/g) | ±30 | ±30 | ±30 |
針對100 g之中和 | 重量g | 重量g | 重量g |
N,N-二甲基乙醇胺 | 3.2 | 3.2 | 3.2 |
針對100 g之分散 | 重量g | 重量g | 重量g |
80℃下之水 | 128 | 128 | 128 |
分散液之固體含量 | ±40% | ±40% | ±40% |
實例22之樹脂可經調配於具有接近零之VOC (揮發性有機化合物)含量且在維持高乾燥速度同時提供極佳外觀之諸如2K水性(聚胺甲酸酯)之塗料組合物中。已觀測到,含有松香GE或氫化松香GE之丙烯酸多元醇誘導更快無塵時間早期硬度發展。
實施態樣[項目1]
一種松香及/或氫化松香縮水甘油酯之用途,其用作用於油漆、黏著劑之黏合劑組合物中之單體,用作活性稀釋劑及用作除酸劑。
[項目2]
一種聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其包含如項目1之松香及/或氫化松香縮水甘油酯。
[項目3]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其特徵在於該聚酯多元醇樹脂係藉由使聚羧酸化合物與松香及/或氫化松香縮水甘油酯之混合物反應來獲得,其中該聚羧酸化合物係藉由使一或多種多官能多元醇與一或多種酐或酸酐反應來獲得。
[項目4]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其中該聚酯多元醇樹脂之酸值以固體樹脂計低於20 mg KOH/g且較佳以固體樹脂計低於10 mg KOH/g,最佳低於6 mg KOH/g。
[項目5]
如項目4之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其中該聚酯多元醇樹脂之數目平均分子量(Mn)根據聚苯乙烯標準品介於300道爾頓與7000道爾頓之間,且/或羥基值以固體計介於40 mg KOH/g固體與320 mg KOH/g固體之間。
[項目6]
一種可用於塗料組合物之黏合劑組合物,其至少包含如項目3至5之任何聚酯多元醇樹脂。
[項目7]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其特徵在於在一或多個步驟中,羥基官能丙烯酸樹脂係藉由利用環氧基與羧酸基之反應來將松香及/或氫化松香縮水甘油酯之混合物併入至羥基官能丙烯酸樹脂中而獲得,該羧酸基來自經由自由基聚合反應與一或多個不飽和單體反應之羥基乙烯羧酸酯單體的乙烯羧酸化合物。
[項目8]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其中該丙烯酸多元醇樹脂包含以固體計介於50 mg KOH/g與180 mg KOH/g之間之經計算之羥基值,且/或根據聚苯乙烯標準品介於1500道爾頓與50000道爾頓之間之數目平均分子量(Mn)。
[項目9]
一種可用於塗料組合物之黏合劑組合物,其至少包含如項目7至8之任何羥基官能丙烯酸樹脂。
[項目10]
一種透明塗料組合物,其包含10重量%至40重量%脂族異氰酸酯、0重量%至25重量%如項目5至8之聚酯多元醇、40重量%至70重量%如項目7至8中任一項之丙烯酸多元醇,所有重量%皆以該溶劑蒸發之後的固體計。
[項目11]
如項目7至8之丙烯酸多元醇,其係在該反應器中在聚酯多元醇存在下製備。
[項目12]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其特徵在於該聚醚多元醇樹脂係藉由使具有至少三個羥基之至少一種多元醇與松香及/或氫化松香縮水甘油酯之混合物反應來獲得。
[項目13]
如項目2之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其中該聚醚多元醇樹脂包含根據聚苯乙烯標準品低於4500道爾頓之數目平均分子量(Mn),且/或以固體計高於120 mg KOH/g固體之羥基值。
[項目14]
一種可用於塗料組合物之黏合劑組合物,其至少包含如項目12至13之任何聚醚多元醇樹脂。
[項目15]
一種金屬、木材或塑膠基板,其塗佈有如項目6、9及14之黏合劑組合物。
[項目16]
如項目3、7及12中任一項之聚酯多元醇樹脂或丙烯酸多元醇樹脂或聚醚多元醇樹脂或聚醚-酯多元醇樹脂或環氧樹脂調配物,其特徵在於使用松香及/或氫化松香縮水甘油酯之混合物作為活性稀釋劑。
Claims (6)
- 一種聚酯多元醇樹脂調配物,其包含松香縮水甘油酯,該松香縮水甘油酯係用作用於油漆或黏著劑之黏合劑組合物中之單體、用作活性稀釋劑、或用作除酸劑,其特徵在於聚酯多元醇樹脂係藉由使聚羧酸化合物與該松香縮水甘油酯反應來獲得,其中該聚羧酸化合物係藉由使一或多種多官能多元醇與一或多種酐或酸酐反應來獲得。
- 如請求項1之聚酯多元醇樹脂調配物,其中該聚酯多元醇樹脂之酸值以固體樹脂計低於20 mg KOH/g。
- 如請求項1之聚酯多元醇樹脂調配物,其中該聚酯多元醇樹脂之數目平均分子量(Mn)根據聚苯乙烯標準品介於300道爾頓與7000道爾頓之間,且/或羥基值以固體計介於40 mg KOH/g固體與320 mg KOH/g固體之間。
- 如請求項1之聚酯多元醇樹脂調配物,其中該松香縮水甘油酯係用作活性稀釋劑。
- 一種可用於塗料組合物之黏合劑組合物,其至少包含由如請求項1至4中任一項之聚酯多元醇樹脂調配物所獲得之聚酯多元醇樹脂。
- 一種基板,其塗佈有如請求項5之黏合劑組合物。
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