TW202110784A - 酚化合物、樹脂組成物及其製造方法以及成形體 - Google Patents
酚化合物、樹脂組成物及其製造方法以及成形體 Download PDFInfo
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- TW202110784A TW202110784A TW109124272A TW109124272A TW202110784A TW 202110784 A TW202110784 A TW 202110784A TW 109124272 A TW109124272 A TW 109124272A TW 109124272 A TW109124272 A TW 109124272A TW 202110784 A TW202110784 A TW 202110784A
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- 238000012360 testing method Methods 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
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- 229920006305 unsaturated polyester Polymers 0.000 description 1
Classifications
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- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
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- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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Abstract
一種由下述通式(I)所表示之酚化合物。通式(I)中,R1
、R2
分別獨立表示氫原子或烷基。
Description
本發明係關於酚化合物、樹脂組成物及其製造方法以及成形體者。
當製造樹脂組成物時,有時會實施將包含聚合溶劑之聚合物溶液在減壓及高溫條件下熱處理的製造程序。在此種熱處理中,通常會因去除聚合溶劑之目的而以遠高於聚合溶劑之沸點的溫度處理聚合物溶液,故經熱處理而獲得之聚合物有時會產生熱劣化或著色等問題。於是,開發了透過對樹脂組成物進行添加而可減輕起因於熱處理之熱劣化等問題的添加劑。
例如在專利文獻1中,提案有酚系化合物,所述酚系化合物得在製造丁二烯系聚合物時為了自聚合物溶液分離聚合物而進行高溫處理時等,防止聚合物之熱劣化及著色。
專利文獻
《專利文獻1》:日本專利公開第H1-168643號公報
於此,當製造樹脂組成物時,在對樹脂(亦即聚合物)施加如上所述之在減壓及高溫條件下之熱處理的情況下,聚合物會分解,因而聚合物有熱劣化的情形。
於是,當製造樹脂組成物時,需要即使於在減壓及高溫條件下實施熱處理的情況下,亦得充分抑制樹脂之分解的添加劑。為此,不僅需要添加劑具有樹脂之分解抑制能力,還需要添加劑本身即使在暴露於高溫條件下的情況下亦不易揮發擴散。
然而,專利文獻1所記載之一丙烯酸雙酚酯化合物及其他眾所周知之添加劑,係在減壓及高溫條件下的樹脂之分解抑制能力不足或在高溫條件下容易揮發擴散者。
於是,本發明以提供一種酚化合物為目的,所述酚化合物即使在暴露於高溫條件下的情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高。
並且,本發明以提供包含上述酚化合物的樹脂組成物及其製造方法為目的。
再者,本發明以提供由上述樹脂組成物而成的成形體為目的。
本發明人等以解決上述問題為目的潛心進行研究。然後,本發明人等新發現滿足特定之結構的酚化合物即使在暴露於高溫條件下的情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力優異,進而完成本發明。
亦即,此發明係以順利解決上述問題為目的者,本發明之酚化合物之特徵在於係由下述通式(I)所表示:
『化1』
(通式(I)中,R1
、R2
分別獨立表示氫原子或烷基。)。如此,具有上述指定之結構的酚化合物即使在暴露於高溫條件下的情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高。是故,透過將此種酚化合物摻合於樹脂組成物,即使在暴露於在減壓、高溫條件下之處理的情況下,亦可充分抑制樹脂的分解。
於此,在本發明之酚化合物中,以前述通式(I)之R1
及R2
分別係氫原子為佳。換言之,以本發明之酚化合物係一丙烯酸雙酚酯化合物為佳。藉由對樹脂組成物摻合此種一丙烯酸雙酚酯化合物,即使在將樹脂組成物暴露於在減壓及高溫條件下之處理的情況下,亦可進一步充分抑制樹脂分解。
並且,在本發明之酚化合物中,以前述通式(I)之R1
係甲基且R2
係氫原子為佳。換言之,以本發明之酚化合物係一甲基丙烯酸雙酚酯化合物為佳。藉由對樹脂組成物摻合此種一甲基丙烯酸雙酚酯化合物,即使在將樹脂組成物暴露於在減壓及高溫條件下之處理的情況下,亦可進一步充分抑制樹脂分解。
並且,此發明係以順利解決上述問題為目的者,本發明之樹脂組成物之特徵在於包含樹脂及於上已述之酚化合物之任一者。若樹脂組成物包含如上所述之酚化合物之至少任一者,則即使在將樹脂組成物暴露於在減壓及高溫條件下之處理的情況下,亦可充分抑制樹脂分解。
於此,在本發明之樹脂組成物中,以前述樹脂係熱塑性聚合物為佳。透過將作為樹脂之熱塑性聚合物與如上所述之酚化合物組合而摻合於樹脂組成物,可進一步有效發揮在減壓及高溫條件下的樹脂之分解抑制能力。
並且,此發明係以順利解決上述問題為目的者,本發明之成形體之特徵在於由上述樹脂組成物成形而成。由於上已述之樹脂組成物成形而成的成形體具有優異之性狀。
並且,此發明係以順利解決上述問題為目的者,本發明之樹脂組成物的製造方法之特徵在於包含將包含前述樹脂及前述酚化合物之混合物在200℃以上且減壓下加熱的加熱工序。透過將包含樹脂及指定之酚化合物之混合物在指定之條件下減壓及加熱,可有效率製造具有良好之性狀的樹脂組成物。
此外,在本說明書中,所謂「在減壓下」,意謂在以絕對壓力計為50 kPa以下的環境下。
根據本發明,可提供一種酚化合物,所述酚化合物即使在暴露於高溫條件下的情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高。
並且,根據本發明,可提供包含上述酚化合物的樹脂組成物及其有效率的製造方法。
再者,根據本發明,可提供由上述樹脂組成物而成的成形體。
以下詳細說明本發明之實施型態。
於此,本發明之酚化合物由於即使在暴露於高溫條件下之情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高,故尤其得合宜對可能在製造時及成形時等暴露於減壓及高溫條件下之處理的樹脂組成物摻合。而且,本發明之樹脂組成物可藉由本發明之樹脂組成物的製造方法來有效率製造。再者,本發明之樹脂組成物可合宜使用作為本發明之成形體的材料。
(酚化合物)
本發明之酚化合物由於滿足以指定之通式(I)表示之結構,故即使在暴露於高溫條件下的情況下亦不易揮發擴散,且在高溫及減壓條件下的樹脂之分解抑制能力夠高。是故,透過對樹脂組成物摻合此種酚化合物,即使在暴露於減壓及高溫條件下之處理的情況下,亦可充分抑制樹脂的分解。
上述通式(I)中,R1
、R2
之烷基分別獨立,得為例如碳數1~6之烷基。作為碳數1~6之烷基,並不特別受限,可列舉例如:甲基、乙基、丙基、丁基、戊基、己基、環己基等具有直鏈、支鏈或環狀結構的烷基。
其中,以R1
、R2
分別獨立為氫原子或甲基為佳。
再者,本發明之酚化合物以熔點為30℃以上為佳,以40℃以上為較佳,且以200℃以下為佳,以150℃以下為較佳,以100℃以下為更佳。若酚化合物之熔點為上述下限值以上,則由於在常溫下會成為固體,故化合物的處理性優異。並且,若酚化合物之熔點為上述上限值以下,則容易變得較樹脂之乾燥溫度或濃縮溫度、成形溫度還低,於使用樹脂組成物之成形體的製造時酚化合物容易充分熔融,得提高所獲得之成形體的透明性。
此外,酚化合物之熔點可依循實施例所記載之方法來量測。
(樹脂組成物)
本發明之樹脂組成物包含樹脂與上述酚化合物。本發明之樹脂組成物由於包含上述酚化合物,故即使在暴露於減壓及高溫條件下之處理的情況下,亦可充分抑制樹脂分解。此外,樹脂組成物亦可任意含有溶劑及添加劑。樹脂組成物在常溫常壓(25℃、1 atm)條件下可為樹脂溶解於溶劑中而成的溶液,亦可為包含固體狀態之樹脂的固形物(例如樹脂顆粒)。
在樹脂組成物中之上述指定之酚化合物的含有比例,將樹脂之含量定為100質量份,以0.01質量份以上為佳,以0.1質量份以上為較佳,且以10質量份以下為佳,以1.0質量份以下為較佳。
〈樹脂〉
於此,作為本發明之樹脂組成物所含有之樹脂,可因應用途使用已知之任何聚合物。作為此種聚合物之一例,可列舉於日本專利公開第H3-207788號公報中作為成分a)列舉之各種聚合物。
具體之例係以下者。
1.一烯烴及二烯烴之聚合物(例如:聚丙烯、聚異丁烯、聚丁烯、聚甲基戊烯、聚異戊二烯或聚丁二烯)以及環烯烴之聚合物(例如:環戊烯或降𦯉烯、雙環戊二烯或四環十二烯之聚合物)、聚乙烯(其可未交聯亦可交聯,例如:高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)及直鏈狀低密度聚乙烯(LLDPE))。
2.上述1所記載之聚合物的混合物,例如:聚丙烯與聚異丁烯的混合物、聚丙烯與聚乙烯的混合物(例如:PP/HDPE及PP/LDPE)及相異種類之聚乙烯的混合物(例如:LDPE/HDPE)。一烯烴及二烯烴的共聚物,以及一烯烴及二烯烴之任一者或兩者與其他乙烯型單體及環烯烴類之任一者或兩者的共聚物、環烯烴類的共聚物,例如:乙烯/丙烯共聚物、直鏈狀低密度聚乙烯(LLDPE)及其與低密度聚乙烯(LDPE)之混合物、丙烯/丁烯共聚物、乙烯/己烯共聚物、乙烯/甲基戊烯共聚物、乙烯/庚烯共聚物、乙烯/辛烯共聚物、丙烯/丁二烯共聚物、異丁烯/異戊二烯共聚物、乙烯/丙烯酸烷酯共聚物、乙烯/甲基丙烯酸烷酯共聚物、乙烯/乙酸乙烯酯或乙烯/丙烯酸共聚物及此等之鹽(離子聚合物),以及乙烯、丙烯與二烯例如己二烯、雙環戊二烯或亞乙基降𦯉烯的三元共聚物、乙烯/降𦯉烯共聚物、乙烯/四環十二烯共聚物;還有此種共聚物彼此的混合物及此種共聚物與於上述1已述之聚合物的混合物例如聚丙烯/乙烯與丙烯共聚物、LDPE/EVA、LDPE/EAA、LLDPE/EVA及LLDPE/EAA。
3.烴樹脂(例如碳原子數5到9)。
4.乙烯芳烴的聚合物,例如:聚苯乙烯、聚(對甲基苯乙烯)、聚(α-甲基苯乙烯)、聚乙烯萘、聚二苯乙烯。
5.苯乙烯或其他乙烯芳族與二烯或丙烯酸系衍生物的共聚物,例如:苯乙烯/丁二烯、苯乙烯/異戊二烯、苯乙烯/丙烯腈、苯乙烯/甲基丙烯酸烷酯、苯乙烯/甲基苯乙烯、苯乙烯/乙烯萘、苯乙烯/甲基苯乙烯/異戊二烯、苯乙烯/乙烯萘/異戊二烯、苯乙烯/丁二烯/丙烯酸烷酯、苯乙烯/順丁烯二酸酐、苯乙烯/丙烯腈/丙烯酸甲酯;由苯乙烯共聚物與其他聚合物例如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物所製造之耐衝擊性混合物;以及苯乙烯的嵌段共聚物例如苯乙烯/丁二烯/苯乙烯、苯乙烯/異戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6.苯乙烯或α-甲基苯乙烯的接枝共聚物,例如:苯乙烯對於聚丁二烯的接枝共聚物;苯乙烯對於聚丁二烯/苯乙烯或聚丁二烯/丙烯腈的接枝共聚物;苯乙烯及丙烯腈(或甲基丙烯腈)對於聚丁二烯的接枝共聚物;苯乙烯及順丁烯二酸酐或順丁烯二醯亞胺對於聚丁二烯的接枝共聚物;苯乙烯、丙烯腈及順丁烯二酸酐或順丁烯二醯亞胺對於聚丁二烯的接枝共聚物;苯乙烯、丙烯腈及甲基丙烯酸甲酯對於聚丁二烯的接枝共聚物;苯乙烯及丙烯酸烷酯或甲基丙烯酸酯對於聚丁二烯的接枝共聚物、苯乙烯及丙烯腈對於乙烯/丙烯/二烯三元共聚物的接枝共聚物、苯乙烯及丙烯腈對於聚丙烯酸烷酯或聚甲基丙烯酸烷酯的接枝共聚物、苯乙烯及丙烯腈對於丙烯酸酯/丁二烯共聚物的接枝共聚物,以及此等與上述5.所記載之共聚物的混合物例如以ABS、MBS、ASA或AES聚合物為人所知的共聚物混合物。
7.鹵化聚合物,例如:聚氯平、氯化橡膠、氯化或磺化聚乙烯、乙烯與氯乙烯的共聚物、表氯醇均聚物及共聚物,以鹵乙烯化合物的聚合物為佳,例如:聚氯乙烯、聚二氯亞乙烯、聚氟乙烯、聚二氟亞乙烯,以及此等之共聚物例如氯乙烯/二氯亞乙烯共聚物、氯乙烯/乙酸乙烯酯或二氯亞乙烯/乙酸乙烯酯共聚物。
8.由α,β-不飽和酸及其衍生物衍生出的聚合物,例如:聚丙烯酸酯及聚甲基丙烯酸酯、聚丙烯醯胺及聚丙烯腈。
9.上述8所記載之單體彼此的共聚物,或上述8所記載之單體與其他不飽和單體的共聚物,例如:丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷酯共聚物、丙烯腈/丙烯酸烷氧烷酯或丙烯腈/鹵乙烯共聚物或丙烯腈/甲基丙烯酸烷酯/丁二烯三元共聚物。
10.由不飽和醇及胺或醯衍生物或此等之縮醛衍生出的聚合物,例如:聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苄酸乙烯酯、聚順丁烯二酸乙烯酯、聚丁酸乙烯酯、聚酞酸烯丙酯或聚烯丙基三聚氰胺,以及上述1所記載之烯烴與此等的共聚物。
11.環醚的均聚物及共聚物,例如:聚烷二醇、聚環氧乙烷、聚環氧丙烷或二環氧丙基醚與此等的共聚物。
12.聚縮醛,例如:聚甲醛及包含環氧乙烷作為共聚單體之種種聚甲醛;使用熱塑性聚胺甲酸酯、丙烯酸酯或MBS改質的聚縮醛。
13.聚氧二甲苯、聚苯硫醚及聚苯乙烯,以及此等之至少任一者與聚醯胺的混合物。
14.由末端具有羥基之聚醚、聚酯或聚丁二烯與脂族或芳族聚異氰酸酯衍生出的聚胺甲酸酯,以及此等的前驅物。
15.由二胺與二羧酸及/或由胺基酸或相當之內醯胺衍生出的聚醯胺或共聚醯胺,例如:聚醯胺4、聚醯胺6、聚醯胺6/6、6/10、6/9、6/12及4/6、聚醯胺11、聚醯胺12、透過間二甲苯二胺與己二酸之縮合獲得的芳族聚醯胺;使用或不使用彈性體作為改質劑之由六亞甲基二胺與異酞酸及/或對酞酸製造出的聚醯胺例如聚(2,4,4-三甲基伸己基對酞醯胺)或聚間苯異酞醯胺;前述聚醯胺與聚烯烴、烯烴共聚物、離子聚合物或者經化學上鍵結或接枝之彈性體的嵌段共聚物,或者前述聚醯胺與聚醚例如聚乙二醇、聚丙二醇或聚伸丁二醇的嵌段共聚物;以及進一步使用EPDM或ABS改質的聚醯胺或共聚醯胺。
16.聚脲、聚醯亞胺、聚醯胺醯亞胺及聚苯并咪唑。
17.由二羧酸與二醇及/或由羥基羧酸或相應之內酯衍生出的聚酯,例如:聚對酞酸乙二酯、聚對酞酸丁二酯、聚對酞酸-1,4-二羥甲基環己酯、聚羥基苄酸酯以及由羥基末端聚醚衍生出的嵌段共聚醚酯;及進一步使用聚碳酸酯或MBS改質的聚酯。
18.聚碳酸酯及聚酯碳酸酯。
19.聚碸、聚醚碸及聚醚酮。
20.由使用飽和及不飽和二羧酸與多元醇及作為交聯劑之乙烯基化合物之共聚酯衍生出的不飽和聚酯,及更低易燃性之此等的含鹵素改質物。
21.由取代丙烯酸酯衍生出的交聯性丙烯酸樹脂,例如:丙烯酸環氧酯、胺甲酸酯丙烯酸酯或聚酯丙烯酸酯。
22.前述聚合物的混合物(高分子摻合物),例如:PP/EPDM、聚醯胺6/EPDM或ABS、PVC/EVA、PVS/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/熱塑性PUR、PC/熱塑性PUR、POM/丙烯酸酯、POM/MBS、PPE/HIPS、PPE/PA6.6及共聚物、PA/HDPE、PA/PP、PA/PPE。
23.上述1至22所記載之聚合物的氫化改質物。
上述列舉之各種聚合物之中,以本發明之樹脂組成物所含有之樹脂係熱塑性聚合物為佳。其中,以熱塑性聚合物包含乙烯芳族的聚合物或其氫化改質物、苯乙烯或其他乙烯芳族與二烯的共聚物及苯乙烯的嵌段共聚物之中之至少任一者為佳。於此,在本說明書中,所謂「熱塑性聚合物」,係得透過加熱呈可成形之程度之流動性的聚合物,意謂能夠檢測出玻璃轉移點及熔點之至少一者且會因加熱至玻璃轉移點或熔點以上之溫度而軟化的聚合物。
此外,於上已述之聚合物並無特別受限,可採用適於用以形成聚合物之單體的已知之任何聚合方法來聚合。甚者,作為聚合物,當然亦能夠使用市售者。
《聚合物的重量平均分子量》
並且,聚合物以重量平均分子量為10,000以上為佳,以50,000以上為較佳,且以1,000,000以下為佳。若聚合物的重量平均分子量為10,000以上,則可提高由樹脂組成物形成之成形體的耐熱性及機械強度。另一方面,若聚合物的重量平均分子量為1,000,000以下,則可提高樹脂組成物的成形性。
此外,聚合物的重量平均分子量可依循實施例所記載之方法來量測。
〈溶劑〉
作為本發明之樹脂組成物得任意含有之溶劑,並無特別受限,可列舉環己烷等飽和烴系溶劑、甲苯等芳族烴系溶劑等。此外,在樹脂組成物為溶液狀的情況下,於樹脂組成物中之溶劑的含量可適當設定。此外,在樹脂組成物為樹脂顆粒等固形物的情況下,於樹脂組成物中之溶劑的含量亦可為零,亦即於樹脂組成物中實質上不含溶劑。
〈添加劑〉
亦可於本發明之樹脂組成物中視需求摻合其他添加劑,例如:抗熱劣化劑、各種抗氧化劑、紫外線吸收劑、受阻胺系光穩定劑(HALS)等光穩定劑、滑劑、成核劑、抗靜電劑、無機填充劑及顏料等。
針對此等添加劑之一部分,以下列舉具體例。
作為抗熱劣化劑,可列舉:丙烯酸-2-三級丁基-4-甲基-6-(2-羥基-3-三級丁基-5-甲苄基)苯酯(Sumilizer GM)、丙烯酸-1′-羥基{2,2′-亞乙基雙[4,6-雙(1,1-二甲基丙基)苯]}-1-酯(Sumilizer GS)。
作為抗氧化劑,並無特別受限,可列舉例如:酚系抗氧化劑、磷系抗氧化劑及硫系抗氧化劑等。
作為酚系抗氧化劑,可列舉例如:丁基羥基甲苯(BHT)、2,2′-亞甲基雙(6-三級丁基對甲酚)(Sumilizer MDP-S)、4,4′-硫雙(6-三級丁基間甲酚)(Sumilizer WX-R)、4,4′-亞丁基雙(6-三級丁基-3-甲酚)(Sumilizer BBM-S)、2,2′-亞甲基雙(4-乙基-6-三級丁基酚)(Yoshinox 425)、3-[3,5-二(三級丁基)-4-羥基苯基]丙酸硬脂酯(Irganox 1076)、肆{3-[3,5-二(三級丁基)-4-羥基苯基]丙酸}新戊四醇酯(Irganox 1010)、雙{3-[3,5-二(三級丁基)-4-羥基苯基]丙酸}-1,6-己二醇酯(Irganox 259)、雙{3-[3,5-二(三級丁基)-4-羥基苯基]丙酸}2,2′-硫二乙酯(Irganox 1035)、N,N′-六亞甲基雙{3-[3,5-二(三級丁基)-4-羥基苯基]丙醯胺}(Irganox 1098)、雙[3-(3-三級丁基-4-羥基-5-甲基苯基)丙酸][伸乙基雙(氧伸乙基)](Irganox 245)、2,4,6-參[3′,5′-二(三級丁基)-4′-羥基苄基]-1,3,5,-三甲苯(Irganox 1330)、1,3,5-參{[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基}-1,3,5-三𠯤-2,4,6(1H,3H,5H)三酮(Irganox 3114)、4-{[4,6-雙(辛硫基)-1,3,5-三𠯤-2-基]胺基}-2,6-二(三級丁基)酚(Irganox 565)、2,4-雙(辛硫基甲基)-6-甲酚(Irganox 1520)、2,4-雙[(十二硫基)甲基]-6-甲酚(Irganox 1726)、1,3,5-參{[4-(1,1-二甲基乙基)-3-羥基-2,6-二甲基苯基]甲基}-1,3,5-三𠯤-2,4,6(1H,3H,5H)三酮(Cyanox 1790)、雙[3-(3-三級丁基-4-羥基-5-甲基苯基)丙酸]-2,2′-二甲基-2,2′-(2,4,8,10-四氧螺[5.5]十一-3,9-二基)二丙-1,1′-二酯(Sumilizer GA-80)、4,4′,4″-(1-甲基丙-3-亞基)參(6-三級丁基間甲酚)(Adekastab AO-30)等。
作為磷系抗氧化劑,可列舉例如:亞磷酸參[2,4-二(三級丁基)苯酯](Irgafos 168)、4,4′,4″,4‴-{[(1,1′-聯苯-4,4′-二基)雙(膦三基)]四氧基}肆[1,3-二(三級丁基)苯](Sandostab P-EPQ)、3,9-雙[2,4-二(三級丁基)苯氧基]-2,4,8,10-四氧基-3,9-二磷螺[5.5]十一烷(Ultranox 626)、3,9-雙[2,6-二(三級丁基)-4-甲基苯氧基]-2,4,8,10-四氧基-3,9-二磷螺[5.5]十一烷(Adekastab PEP-36)、亞磷酸-2,2′-亞甲基雙[4,6-二(三級丁基)苯酯]-2-乙基己酯(Adekastab HP-10)、2-三級丁基-6-甲基-4-(3-{[2,4,8,10-四(三級丁基)二苯[d,f][1,3,2]二氧基膦-6-基]氧基}丙基)酚(Sumilizer GP)等。
作為硫系抗氧化劑,可列舉例如:3,3′-硫二丙酸二月桂酯(Sumilizer TPL-R)、3,3′-硫二丙酸二(十四酯)(Sumilizer TPM)、3,3′-硫二丙酸二硬脂酯(Sumilizer TPS)、雙[3-(十二硫基)丙酸]-2,2-雙{[3-(十二硫基)-1-側氧丙基氧基]甲基}-1,3-丙二酯(Sumilizer TP-D)等。
作為金屬減活劑,可列舉例如:N,N′-雙{3-[3,5-二(三級丁基)-4-羥基苯基]丙醯基}肼(Irganox MD1024)、2,2-草醯胺雙{3[3,5-二(三級丁基)羥基苯基]丙酸乙酯}(Naugard LX-1)等。
作為紫外線吸收劑,可列舉例如:2-(2H-苯并三唑-2-基)-4-甲基苯酚(Tinuvin P;drometrizole)、2-(5-氯-2H-苯并三唑-2-基)-6-(1,1-二甲基乙基)-4-甲基苯酚(Tinuvin 326;bumetrizole)、4,6-雙(1,1-二甲基丙基)-2-(2H-苯并三唑-2-基)酚(Tinuvin 328)、2-[2-羥基-5-(1,1,3,3-四甲基丁基)苯基]苯并三唑(Tinuvin 329;octrizole)、2-[2-羥基-3,5-雙(α,α-二甲基苄基)苯基]-2H-苯并三唑(Tinuvin 234)、雙{2-[2-羥基-5-(1,1,3,3-四甲基丁基)苯基]苯并三唑}(Tinuvin 360)、3,5-二(三級丁基)-4-羥基苄酸-2,4-二(三級丁基)苯酯(Tinuvin 120)、2-羥基-4-正辛氧基二苯甲酮(Chimassorb 81;octabenzone)、2-(4,6-二苯基-1,3,5-三𠯤-2-基)-5-己氧基苯酚(Tinuvin 1577)、2-[4,6-二(2,4-二甲苯基)-1,3,5-三𠯤-2-基]-5-辛氧基酚(Cyasorb UV-1164)、2-(4,6-二苯基-1,3,5-三𠯤-2-基)-5-[2-(2-乙基己醯氧基)乙氧基]酚(Adekastab LA-46)、2,4,6-參(2-羥基-4-己氧基-3-甲基苯基)-1,3,5-三𠯤(Adekastab LA-F70)等。
作為HALS,可列舉例如:癸二酸雙(2,2,6,6-四甲基-4-哌啶酯)(Tinuvin 770)、2-{[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基}-2-丁基丙二酸雙[1,2,2,6,6-五甲基-4-哌啶酯](Tinuvin 144)、癸二酸雙[2,2,6,6-四甲基-1-(辛氧基)哌啶-4-酯](Tinuvin 123)、1,5,8,12-肆[4,6-雙(N-丁基-N-1,2,2,6,6-五甲基-4-哌啶基胺基)-1,3,5-三𠯤-2-基]-1,5,8,12-四吖十二烷(Tinuvin 119)、琥珀酸二甲酯/1-(2-羥基乙基)-4-羥基-2,2,6,6-四甲基-4-哌啶聚縮物(Tinuvin 622)、聚({6-[(1,1,3,3-四甲基丁基)胺基]對稱三𠯤-2,4-二基}-[(2,2,6,6-四甲基-4-哌啶基)亞胺基]六亞甲基[(2,2,6,6-四甲基-4-哌啶基)亞胺基])(Chimassorb 944)、由1,6-己胺及N,N′-雙(2,2,6,6-四甲基-4-哌啶基)而成的聚合物與2,4,6-三氯-1,3,5-三𠯤及N-丁基-1-丁胺與N-丁基-2,2,6,6-四甲基-4-哌啶胺的反應物(Chimassorb 2020)、聚{(6-N-𠰌啉基對稱三𠯤-2,4-二基)[(2,2,6,6-四甲基-4-哌啶基)亞胺基]六亞甲基[(2,2,6,6-四甲基-4-哌啶基)亞胺基]}(Cyasorb UV-3346)、由1,6-己二胺及N,N′-雙(2,2,6,6-四甲基-4-哌啶基)而成的聚合物與𠰌啉-2,4,6-三氯-1,3,5-三𠯤的反應物(Cyasorb UV-3529)、肆(1,2,2,6,6-五甲基-4-哌啶基)丁烷(Adekastab LA-52)、肆(2,2,6,6-四甲基-4-哌啶基)丁烷-1,2,3,4-四羧酯(Adekastab LA-57)、1,2,3,4-丁烷四羧酸四甲酯與1,2,2,6,6-五甲基-4-哌啶醇與β,β,β′,β′-四甲基-2,4,8,10-四氧螺[5.5]十一烷-3,9-二乙醇的反應物(Adekastab LA-63P)、1,2,3,4-丁烷四羧酸四甲酯與2,2,6,6-四甲基-4-哌啶醇與β,β,β′,β′-四甲基-2,4,8,10-四氧螺[5.5]十一烷-3,9-二乙醇的反應物(Adekastab LA-68)等。
(樹脂組成物的製造方法)
本發明之樹脂組成物的製造方法之特徵在於包含將包含於上已述之樹脂及於上已述之酚化合物之混合物在200℃以上且減壓下加熱的加熱工序。
更具體而言,上述加熱工序得為下述之工序:自上述混合物去除於上述混合物中不可避免可能含有之雜質及於上述混合物中得任意摻合之溶劑的至少一部分,將上述混合物乾燥及濃縮,獲得溶液狀或固體狀的樹脂組成物。
在加熱工序中之加熱溫度必須為200℃以上,且得為400℃以下。並且,在加熱工序中之壓力以絕對壓力計,以50 kPa以下為佳,以20 kPa以下為較佳。換言之,在加熱工序中,以實施在50 kPa以下之壓力條件下將混合物加熱至200℃以上的操作為佳。
在加熱工序中,只要滿足上述溫度條件及壓力條件即無特別受限,可實施使用了離心薄膜連續蒸發機、刮面式熱交換型連續反應器型蒸發機及高黏度反應器裝置等眾所周知之裝置的直接加熱乾燥法。
此外,得於加熱工序之前,進行將於上已述之樹脂及於上已述之酚化合物混合而獲得混合物的工序。作為混合方法,並無特別受限,可舉出對由樹脂溶解而成之溶液添加指定之酚化合物並透過已知之方法混合的方法。
再者,亦可於加熱工序之後,實施將含有樹脂及指定之酚化合物之熔融體造粒以形成顆粒狀之樹脂組成物的造粒工序。
(成形體)
本發明之成形體係由於上已述之樹脂組成物成形而成。本發明之成形體由於包含樹脂與於上已述之特定之酚化合物,故即使在暴露於減壓及高溫條件下的情況下,樹脂(聚合物)之分解亦不易進行,可良好維持機械強度等性狀。而且,本發明之成形體可便於使用作為例如光學透鏡等。
本發明之成形體可因應期望之形狀而經由合適之已知之成形方法,來成形為薄膜或各種形狀之成形體。作為成形方法,並無特別受限,可列舉例如:射出成形法、擠製成形法及吹塑成形法等。再者,作為成形方法,亦可舉出透過紡絲黏合法或熔噴法等熔融紡絲對不織布或纖維加工的方法。成形條件可因應成形時使用之機材及成形體之期望之形狀等適當設定。
『實施例』
接下來,透過實施例進一步詳細說明本發明,但本發明並非因此等例而受到任何限定者。
此外,在各例中的量測或評價藉由以下方法進行。並且,滿足通式(I)的各種酚化合物依循製造例1~2所記載之程序製造。
甚者,在以下說明中,表示量的「份」及「%」除非特別註記,否則係質量基準。而且,在以下說明中所記載之壓力皆為絕對壓力。
各種物性之量測及各種評價依循下述方法進行。
(1)待測樣本的揮發性評價及酚化合物的熔點
分別使用依循製造例1、2製造出之酚化合物及在各個比較例2~4中使用之各種添加劑作為待測樣本。將待測樣本10 mg放入鋁盤,使用微差熱熱重量同時量測裝置(TG/DTA,Hitachi High-Tech Science Corporation製,產品名「STA7200」),以升溫速度15℃/分鐘加溫至30℃~300℃,獲得加溫結束後之重量減少率,依循下述基準評價各待測樣本的揮發性。
A:未達5%
B:5%以上
並且,酚化合物的熔點,使用熔點量測裝置(梅特勒―托利多公司製,產品名「MP70」),將量測起始溫度定為20℃,將量測結束溫度定為200℃,以升溫速度5℃/分鐘進行量測。如此操作獲得依循製造例1、2製造出之酚化合物的熔點。
(2)重量平均分子量(Mw)
重量平均分子量(Mw)以利用將四氫呋喃作為溶析液之凝膠滲透層析法(GPC)的標準聚苯乙烯換算值的形式求出。作為標準聚苯乙烯,使用東曹公司製標準聚苯乙烯(Mw=589、1,010、3,120、9,490、13,700、37,200、98,900、189,000、397,000)。作為量測裝置,使用東曹公司製之HLC8020GPC,管柱則串聯3支東曹公司製之管柱(TSKgel G5000HXL、TSKgel G4000HXL及TSKgel G2000HXL)來使用,在流速1.0 mL/分鐘、樣本注入量100 μL、管柱溫度40℃的條件下進行。
(3)分解抑制能力的評價
將在加熱工序前之時間點之聚合物的重量平均分子量定為Mw0,將在造粒後之時間點之聚合物的重量平均分子量定為Mw1,求出重量平均分子量維持率(%)=Mw1/Mw0×100,依循下述基準,評價待測樣本(依循製造例1、2製造出之酚化合物及在各個比較例2~4中使用之各種添加劑)之聚合物分解抑制能力。
A:90%以上
B:80%以上且未達90%
C:未達80%
(4)透明性的評價
針對由在實施例、比較例獲得之樹脂組成物成形而成的成形體(平板),使用霧度計(日本電色工業公司製,產品名NDH2000)依循JIS K 7136:2000量測霧度(漫透射率相對於全光線穿透率的比率:%),依循下述基準評價成形體的透明性。
A:0.5%以下
B:超過0.5且未達1.0%
C:1.0%以上
(製造例1)
於具備溫度計、攪拌裝置的四頸燒瓶置入2,4-雙(α,α-二甲苄基)酚100份、二甲苯133份、十二基磺酸1.2份、10%對甲苯磺酸25份、甲醛4.3份,以氮氣置換後,在110℃下攪拌4小時同時進行反應,獲得反應液。反應結束後,對反應液放入二甲苯2400份,對水層予以分液去除。之後,有機層水洗至成為中性。隨後,在90~110℃、約200 mmHg之減壓下,一邊將溶劑回流一邊將水分餾至系統外。將所獲得之縮合反應混合物冷卻後,置入三乙胺15.2份,以氮氣置換後,滴入丙烯醯氯6.8份,在40℃保溫1小時。之後將有機層水洗至成為中性,進一步將二甲苯減壓餾除。隨後,藉由對此蒸餾殘渣加入甲醇以結晶析出,獲得87份之丙烯酸-2,4-雙(α,α-二甲苄基)-6-[2-羥基-3,5-雙(α,α-二甲苄基)]苄基苯酯(一丙烯酸雙酚酯化合物。以下亦稱作「酚化合物1」。由下式所表示。)。在依循上述來評價酚化合物1的揮發性時獲得之重量減少率(利用TG/DTA之量測值)為2.8%。再者,酚化合物1的熔點為52℃。
『化4』
(製造例2)
除了將丙烯醯氯改變為甲基丙烯醯氯以外,比照製造例1進行,獲得甲基丙烯酸-2,4-雙(α,α-二甲苄基)-6-[2-羥基-3,5-雙(α,α-二甲苄基)]苄基苯酯(一甲基丙烯酸雙酚酯化合物。以下亦稱作「酚化合物2」。由下式所表示。)。依循上述而獲得之重量減少率(利用TG/DTA之量測值)為2.8%。再者,酚化合物2的熔點為57℃。
『化5』
(實施例1)
〈熱塑性樹脂製備工序(聚合~氫化)〉
於具備攪拌裝置且內部充分經氮氣置換的反應器放入脫水環己烷231份、脫水苯乙烯100份及二丁醚0.39份。一邊在60℃攪拌所有內容物,一邊加入正丁基鋰(15%環己烷溶液)0.53份使聚合起始。繼續在60℃攪拌所有內容物60分鐘。隨後,藉由加入異丙醇0.18份使反應終止,獲得聚苯乙烯溶液。
將聚苯乙烯溶液移至具備攪拌裝置的耐壓反應器,添加矽藻土負載型鎳觸媒(日揮觸媒化成公司製,產品名「E22U」,鎳負載量60%)10份作為氫化觸媒,攪拌0.1小時。以氫氣置換反應器內部,進一步一邊攪拌溶液一邊供應氫氣,在溫度180℃、壓力4.6 MPa進行氫化反應7小時。藉此,獲得「包含作為摻合於樹脂組成物的聚合物之氫化聚苯乙烯」的反應溶液。所獲得之氫化聚苯乙烯的重量平均分子量(Mw0)為90,000。
對反應溶液加入在製造例1獲得之酚化合物1(一丙烯酸雙酚酯化合物)0.5份並使之溶解。以矽藻土(昭和化學工業公司製,產品名「RADIOLITE(註冊商標)#500」)作為過濾床,在壓力0.35 MPa將此溶液加壓過濾(石川島播磨重工公司製「FUNDABAC濾器」)去除氫化觸媒,獲得無色透明的氫化聚苯乙烯溶液。
〈加熱工序(濃縮工序)〉
將氫化聚苯乙烯溶液在氮氣環境下加熱至200℃,以壓力3 MPa連續供應至薄膜蒸發器(日立製作所公司製,產品名KONTRO)。薄膜蒸發器之運轉條件,設定為在壓力13.4 kPa下,內部之經濃縮的聚合物溶液之溫度為200℃。接下來,將經濃縮的溶液自薄膜蒸發器連續導出,進一步在壓力1.6 MPa供應至同型的薄膜蒸發器。運轉條件定為壓力0.5 kPa、溫度260℃。
〈造粒工序〉
將包含熔融狀態之聚合物的組成物自薄膜蒸發器連續導出,在等級100之無塵室內於200℃下自模具擠製出,水冷後,以造粒機(產品名「OSP-2」,長田製作所公司製)切割,獲得作為「包含酚化合物1(一丙烯酸雙酚酯化合物)與作為聚合物的氫化聚苯乙烯」之樹脂組成物的顆粒。使顆粒再度溶解於環己烷,進行Mw1之量測,結果Mw1為86,000。
〈成形工序〉
使用小型混練機(Micro 15 Compounder,DSMXplore公司製)在260℃、100 rpm之條件下混練顆粒1分鐘使之熔融後,利用小型射出成形機(Micro Injection Moulding Machine 10cc,DSMXplore公司製)在成形溫度260℃、射出壓力0.7 MPa、模具內保持時間10秒且將各個模具溫度定為100℃之條件下,成形為縱長70 mm、橫寬30 mm、厚度3 mm的平板。所獲得之作為成形體之平板的霧度為0.3%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
(實施例2)
除了對包含作為熱塑性樹脂之氫化聚苯乙烯的反應溶液加入酚化合物2(一甲基丙烯酸雙酚酯化合物)0.5份以外,實施與實施例1相同的各種操作,獲得顆粒及平板。顆粒之Mw1為85,500。並且,平板之霧度為0.4%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
(比較例1)
除了於氫化反應後未添加酚化合物1以外,實施與實施例1相同的各種操作,獲得顆粒及作為成形體之平板。顆粒之Mw1為60,000。並且,平板之霧度為1.1%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
(比較例2)
除了對包含作為熱塑性樹脂之氫化聚苯乙烯的反應溶液加入係為不滿足通式(I)所示之結構之添加劑的Sumilizer GS(住友化學公司製:丙烯酸-1′-羥基{2,2′-亞乙基雙[4,6-雙(1,1-二甲基丙基)苯]}-1-酯,下式)0.5份以外,實施與實施例1相同的各種操作,獲得顆粒及作為成形體之平板。Sumilizer GS之重量減少率為12.7%。並且,顆粒之Mw1為77,000。甚者,平板之霧度為0.4%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
『化6』
(比較例3)
除了對包含作為熱塑性樹脂之氫化聚苯乙烯的反應溶液加入係為不滿足通式(I)所示之結構之添加劑的Sumilizer GM(住友化學公司製,丙烯酸-2-三級丁基-4-甲基-6-(2-羥基-3-三級丁基-5-甲苄基)苯酯:下式)0.5份以外,實施與實施例1相同的各種操作,獲得顆粒及作為成形體之平板。Sumilizer GM之重量減少率為29.5%。並且,顆粒之Mw1為75,000。甚者,平板之霧度為0.9%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
『化7』
(比較例4)
除了對包含作為熱塑性樹脂之氫化聚苯乙烯的反應溶液加入係為不滿足通式(I)所示之結構之添加劑的Irganox 1010(BASF JAPAN公司製,肆{3-[3,5-二(三級丁基)-4-羥基苯基]丙酸}新戊四醇酯)0.5份以外,實施與實施例1相同的各種操作,獲得顆粒及作為成形體之平板。顆粒之Mw1為64,000。並且,平板的霧度為0.4%。依據所獲得之各種量測值,依循上述進行各種評價。結果揭示於表1。
『表1』
實施例 | 比較例 | ||||||
1 | 2 | 1 | 2 | 3 | 4 | ||
滿足式(1)之酚化合物 | 製造例No. | 1 | 2 | - | - | - | - |
R1 | H | CH3 | - | - | - | - | |
R2 | H | H | - | - | - | - | |
添加劑 | - | - | - | Sumilizer GS | Sumilizer GM | Irganox 1010 | |
評價 | 揮發性 | A | A | - | B | B | A |
分解抑制能力 | A | A | C | B | B | C | |
透明性 | A | A | C | A | B | A |
由表1之實施例1~2明顯可知,具有滿足通式(I)之指定之結構的一丙烯酸雙酚酯化合物及一甲基丙烯酸雙酚酯化合物,即使在暴露於高溫條件下之情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高。
另一方面,由比較例1可確認到,在不摻合此種指定之一丙烯酸雙酚酯化合物或一甲基丙烯酸雙酚酯化合物的情形中,於實施例1使用之熱塑性樹脂,在暴露於真空、高溫條件之情況下進行了分解。
並且,由比較例2~3可知,具有與在實施例1使用之一丙烯酸雙酚酯化合物類似之結構但不滿足通式(I)的添加劑,在減壓及高溫條件下的樹脂之分解抑制能力不足,並且在暴露於高溫條件下之情況下有易揮發擴散的傾向。
甚者,由比較例4可知,結構與在實施例1使用之一丙烯酸雙酚酯化合物顯著相異之抗氧化劑(Irganox 1010)在高溫條件下雖不易揮發擴散,但在減壓及高溫條件下的樹脂之分解抑制能力不足。
而且,在實施例1~2中,透明性之評價結果皆為「A」評價。由此可知,根據具有滿足通式(I)之指定之結構的一丙烯酸雙酚酯化合物及一甲基丙烯酸雙酚酯化合物,得在暴露於高溫條件下之情況下妥善抑制樹脂著色。
根據本發明,可提供即使在暴露於高溫條件下之情況下亦不易揮發擴散,且在減壓及高溫條件下的樹脂之分解抑制能力夠高的酚化合物。
並且,根據本發明,可提供包含上述酚化合物的樹脂組成物及其有效率的製造方法。
再者,根據本發明,可提供由上述樹脂組成物而成的成形體。
無。
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