TWI436978B - 雙酚單酯化合物 - Google Patents
雙酚單酯化合物 Download PDFInfo
- Publication number
- TWI436978B TWI436978B TW097145629A TW97145629A TWI436978B TW I436978 B TWI436978 B TW I436978B TW 097145629 A TW097145629 A TW 097145629A TW 97145629 A TW97145629 A TW 97145629A TW I436978 B TWI436978 B TW I436978B
- Authority
- TW
- Taiwan
- Prior art keywords
- butyl
- propylene
- tert
- thermoplastic polymer
- ethylene
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 54
- 229920001169 thermoplastic Polymers 0.000 claims description 46
- 239000003381 stabilizer Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- -1 alkyl Hydrogen ketone Chemical compound 0.000 description 55
- 229920001577 copolymer Polymers 0.000 description 27
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 4
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- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 235000006708 antioxidants Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
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- 238000000034 method Methods 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
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- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- CPAJUXUFVYLYLX-UHFFFAOYSA-N [1-(hydroxymethyl)-3,5,8-trioxabicyclo[2.2.2]octan-4-yl]phosphonic acid Chemical compound C1OC2(P(O)(O)=O)OCC1(CO)CO2 CPAJUXUFVYLYLX-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
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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
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- 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
- C07C69/67—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 saturated acids
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
本發明係關於雙酚單酯化合物。
為了改善熱塑性聚合物的熱安定性,專利文獻1揭露一種含有式(1)所示化合物作為活性成分的安定劑。
專利文獻:1.第1-16864號日本專利案
本發明之目的在於提供一種用以進一步改善熱塑性聚合物之安定性的化合物。
在此等情況下,本發明者發現某些雙酚單酯化合物而完成本發明。亦即,本發明提供下述[1]至[6]之內容。
[1]一種式(1)所示之雙酚單酯化合物:
(式(1)中,R各自獨立,表示氫原子或甲基,且R’表示碳數1至6的烷基或氫原子)。
[2]一種安定劑,包括如[1]所定義之雙酚單酯化合物
作為活性成份。
[3]如[2]之安定劑,包括0.005wt%至100wt%之如[1]所定義的雙酚單酯化合物。
[4]一種熱塑性聚合物組成物,包括如[2]或[3]所定義之安定劑,以及熱塑性聚合物。
[5]一種如[2]或[3]所定義之安定劑之用途,係用於熱安定化熱塑性聚合物。
[6]一種製造如[1]所定義之雙酚單酯化合物的方法,包括使式(2)所示之雙酚:
(式(2)中,R’表示碳數為1至6的烷基或氫原子)與式(3)所示之化合物:
(式(3)中,R各自獨立,表示氫原子或甲基,且X表示鹵素原子、羥基或碳數為1至6的烷氧基)反應。
本發明之化合物係一種如式(1)所示之雙酚單酯化合物(下文中,在某些情況,被稱為化合物(1))。
本文中,R各自獨立,表示氫原子甲基。較佳地,全部R皆為氫原子。
R’係碳數為1至6的烷基如甲基、乙基及正丁基,或氫原子,並以甲基為特佳。
用以製造化合物(1)之方法的實例包括:使2,4-二-第三戊基酚與R’CHO反應以製造雙酚(2)以及,接著使該雙酚(2)與式(3)所示之化合物(下文中,在某些情況被稱為化合物(3))反應。化合物(3)之X係以鹵素原子如氯為特佳。具體而言,用亞硫醯氯將化合物(3)之X為羥基之化合物轉變為鹵化物,然後將該鹵化物與雙酚反應。
化合物(3)的實例包括:丙烯酸2-羧基乙酯、甲基丙烯酸2-羧基乙酯、甲基丙烯酸2-羧基-2-甲酯、丙烯酸2-羧基-2-甲酯、及其氯化物。
丙烯酸2-羧基乙酯可由市場上購得,例如自Aldrich公司。
本發明之安定劑係以熱安定化熱塑性聚合物的熱安定劑為較佳。本發明之安定劑包含0.005wt%至100wt%,較佳地0.01wt%至100wt%,更佳地0.1至100wt%,之化合物(1)作為活性成分。
在不會抑制本發明效果的範圍內,本發明之安定劑可包含化合物(1)以外的添加劑。此等添加劑的實例包含抗氧化劑(例如酚系抗氧化劑、磷系抗氧化劑以及硫系抗氧化劑)、紫外線吸收劑、光安定劑、金屬鈍化劑、成核劑、潤滑劑、抗靜電劑、阻燃劑、填料、顏料、增塑劑、防黏連劑(anti-blocking agents)、界面活性劑、加工助劑、膨脹劑、乳化劑、光亮劑、中和劑如硬脂酸鈣和鋁碳酸鎂(hydrotalcite)、以及黏合劑。
尤其,以抗氧化劑為較佳,且其中係以酚系抗氧化劑為較佳。
酚系抗氧化劑之實例包括:烷基化單酚,如2,6-二-第三丁基-4-甲基酚、2,4,6-三-第三丁基酚、2,6-二-第三丁基酚、2-第三丁基-4,6-二甲基酚、2,6-二-第三丁基-4-乙基酚、2,6-二-第三丁基-4-正丁基酚、2,6-二-第三丁基-4-異丁基酚、2,6-二環戊基-4-甲基酚、2-(α-甲基環己基)-4,6-二甲基酚、2,6-雙十八烷基-4-甲基酚、2,4,6-三環己基酚、2,6-二-第三丁基-4-甲氧基甲基酚、2,6-二-壬基-4-甲基酚、2,4-二甲基-6-(1’-甲基十一基-1’-基)酚、2,4-二甲基-6-(1’-甲基十七烷基-1’-基)酚、2,4-二申基-6-(1’-甲基十三烷基-1’-基)酚、及其混合物;烷硫基甲基酚,如2,4-二辛硫基甲基-6-第三丁基酚、2,4-二辛硫基甲基-6-甲基酚、2,4-二辛硫基甲基-6-乙基酚、2,6-雙十二烷硫基甲基-4-壬基酚、及其混合物;氫醌和烷基化氫酮,如2,6-二-第三丁基-4-甲氧基酚、2,5-二-第三丁基氫醌、2,5-二-第三戊基氫醌、2,6-二苯基-4-十八烷基氧基酚、2,6-二第三丁基氫醌、2,5-二-第三丁基-4-羥基苯甲醚、硬脂酸[3,5-二-第三丁基-4-羥基苯酯]、己二酸雙(3,5-二-第三丁基-4-羥基苯酯)、及其混合物;生育酚,如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚、及其混合物;羥基化二苯硫醚,如2,2’-硫雙(6-第三丁基酚)、2,2’-硫雙(4-甲基-6-第三丁基酚)、2,2’-硫雙(4-辛基酚)、4,4’-硫雙(3-甲基-6-第三丁基酚)、4,4’-硫雙(2-甲基-6-第三丁基酚)、4,4’-硫雙(3,6-二-第三戊基酚)、及4,4’-(2,6-二甲基-4-羥基苯)二硫醚;亞烷基雙酚,如2,2’-亞甲基雙(4-甲基-6第三丁基酚)、2,2’-亞甲基雙(4-乙基-6-第三丁基酚)、2,2’-亞甲基雙[4-甲基-6-(α-甲基環己基)酚]]、2,2’-亞甲基雙(4-甲基-6-環己基酚)、2,2’-亞甲基雙(4-甲基-6-壬基酚)、2,2’-亞甲基雙(4,6-二-第三丁基酚),2,2’-亞乙基雙(4,6-二-第三丁基酚)、2,2’-亞乙基雙(4-異丁基-6-第三丁基酚)、2,2’-亞甲基雙[6-(α-甲基苯甲基)-4-壬基酚]、2,2’-亞甲基雙[6-(α,α-二甲基苯甲基)-4-壬基酚]、4,4’-亞甲基雙(6-第三丁基-2-甲基酚)、4,4’-亞甲基雙(2,6-二-第三丁基酚)、4,4’-亞丁基雙(3-甲基-6-第三丁基酚)、1,1-雙(4-羥基苯基)環己烷、1,1-雙(5-第三丁基-4-羥基-2-甲基苯基)丁烷、2,6-雙(3-第三丁基-5-甲基-2-羥基苯甲基)-4-甲基酚、1,1,3-參(5-第三丁基-4羥基-2-甲基苯基)丁烷、1,1-雙(5-第三丁基-4-羥基-2-甲基苯基)-3-正十二烷基巰基丁烷、乙二醇雙[3,3-雙-3’-第三丁基-4’-羥基苯]丁酸酯]、雙(3-第三丁基-4-羥基-5-甲基苯基)二環戊二烯、對苯二甲酸雙[2-(3’-第三丁基-2’-羥基-5’-甲基苯甲基)-6-第三丁基-4-甲基苯酯]、1,1-雙(3,5-二甲基-2-羥基苯)丁烷、2,2-雙(3,5-二-第三丁基-4-羥基苯基)丙烷、2,2-雙(5-第三丁基-4-羥基-2-甲基苯基)-4-正十二烷基巰基丁烷、1,1,5,5-四(5-第三丁基-4-羥基-2-甲基苯基)戊烷、丙烯酸2-第三丁基-6-(3’-第三丁基-5’-甲基-2’-羥基苯甲基)-4-甲基苯基酯、丙烯酸2,4-二-第三戊基-6-[1-(2-羥基-3,5-二-第三戊基苯基)乙基]苯酯、及其混合物及其衍生物;O-苯甲基衍生物、N-苯甲基衍生物及S-苯甲基衍生物’如3,5,3’,5’-四-第三丁基-4,4’-二羥基二苯甲基醚、4-羥基-3,5-二甲基苯甲基硫基醋酸十八烷酯]、參(3,5-二-第三丁基-4-羥基苯甲基)胺、二硫代對苯二甲酸雙(4-第三丁基-3-羥基-2,6-二甲基苯甲酯)、雙(3,5-二-第三丁基-4-羥基苯甲基)硫醚、3,5-二-第三丁基-4-羥基苯甲基硫基醋酸異辛酯、及其混合物;羥基苯甲基化丙二酸酯衍生物’如2,2-雙(3,5-二-第三丁基-2-羥基苯甲基)丙二酸二(十八烷酯)、2-(3-第三丁基-4-羥基-5-甲基苯甲基)丙二酸二(十八烷酯)、2,2-雙(3,5-二-第三丁基-4-羥基苯甲基)丙二酸二(十二烷基硫基乙酯)、2,2-雙(3,5-二-第三丁基-4-羥基苯甲基)丙二酸雙[4-(1,1,3,3-四甲基丁基)苯酯]、及其混合物;芳族羥基苯甲基衍生物’如1,3,5-三甲基-2,4,6-參(3,5-二-第三丁基-4-羥基苯甲基)苯、1,4-雙(3,5-二-第三丁基-4-羥基苯甲基)-2,3,5,6-四甲基苯、2,4,6-參(3,5-二-第三丁基-4-羥基苯甲基)酚、及其混合物;三衍生物,如2,4-雙(n-辛基硫基)-6-(4-羥基-3,5-二-第三丁基苯胺基)-1,3,5-三、2-正辛基硫基-4,6-雙(4-羥基-3,5-二-第三丁基苯胺基)-1,3,5-三、2-正辛基硫-4,6-雙(4-羥基-3,5-二-第三丁基苯氧基)-1,3,5-三、2,4,6-參(3,5-二-第三丁基-4-苯氧基)-1,3,5-三、參(4-第三丁基-3-羥基-2,6-二甲基苯甲基)異三聚氰酸酯、參(3,5-二-第三丁基-4-羥基苯甲基)異三聚氰酸酯、2,4,6-參(3,5-二-第三丁基-4-羥基苯乙基)-1,3,5-三、2,4,6-參(3,5-二-第三丁基-4-羥基苯丙基)-1,3,5-三、參(3,5-二環己基-4-羥基苯甲基)異三聚氰酸酯、參[2-(3’,5’-二-第三丁基-4’-羥基桂皮醯氧基)乙基]異三聚氰酸酯、及其混合物;苯甲基膦酸酯衍生物,如3,5-二-第三丁基-4-羥基苯甲基膦酸二甲酯、3,5-二-第三丁基-4羥基苯甲基膦酸二乙酯、3,5-二-第三丁基-4-羥基苯甲基膦酸二(十八烷酯)、5-第三丁基-4-羥基-3-甲基苯甲基膦酸二(十八烷酯)、3,5-二-第三丁基-4羥基苯甲基膦酸單酯鉀鹽、及其混合物。醯基胺基酚衍生物,如N-苯基-4-羥基月桂醯胺(4-hydroxylauric acid anilide)、N-苯基-4-羥基硬脂醯胺、N-(3,5-二-第三丁基-4-羥基苯基)胺基甲酸辛酯、及其混合物;β-(3-(3,5-二-第三丁基-4-羥基苯基)丙酸與一元醇或多元醇所形成的酯,該一元醇或多元醇係如甲醇、乙醇、辛醇、硬脂醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺環乙二醇(spiro glycol)、三乙二醇、新戊四醇、參(羥乙基)異三聚氰酸酯、N,N’-雙(羥乙基)草醯胺、3-硫雜十一醇(3-thiaundecanol)、3-硫雜十五醇(3-thiapentadecanol)、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜二環[2,2,2]辛烷、及其混合物;β-(5-第三丁基-4-羥基-3-甲基苯基)丙酸與一元醇或多元醇所形成的酯,該一元醇或多元醇係如甲醇、乙醇、辛醇、硬脂醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺環乙二醇(spiro glycol)、三乙二醇、新戊四醇、參(羥乙基)異三聚氰酸酯、N,N’-雙(羥乙基)草醯胺、3-硫雜十一醇、3-硫雜十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜二環[2,2,2]辛烷、及其混合物;β-(3,5-二環己基-4-羥基苯基)丙酸與一元醇或多元醇所形成的酯,該一元醇或多元醇係如甲醇、乙醇、辛醇、硬脂醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺環乙二醇(spiro glycol)、三乙二醇、新戊四醇、參(羥乙基)異三聚氰酸酯、N,N’-雙(羥乙基)草醯胺、3-硫雜十一醇、3-硫雜十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜二環[2,2,2]辛烷、及其混合物;3,5-二-第三丁基-4-羥基苯基醋酸與一元醇或多元醇所形成的酯,該一元醇或多元醇係如甲醇、乙醇、辛醇、硬脂醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺環乙二醇(spiro glycol)、三乙二醇、新戊四醇、參(羥乙基)異三聚氰酸酯、N,N’-雙(羥乙基)草醯胺、3-硫雜十一醇、3-硫雜十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜二環[2,2,2]辛烷、及其混合物;β-(3,5-二-第三丁基-4-羥基苯)丙酸的醯胺,如N,N’-雙[3-(3’,5’-二-第三丁.基-4’羥基苯基)丙醯基]聯胺、N,N’-雙[3-(3’,5’-二-第三丁基-4’-羥基苯基)丙醯基]六亞甲二胺、N,N’-雙[3-(3’,5’-二-第三丁基-4’-羥基苯基)丙醯基]三亞甲二胺、及其混合物。此等酚系抗氧化劑可單獨使用或可混和兩種或更多種來使用。
尤佳的酚系抗氧化劑的實例包括:2,6-二-第三丁基-4-甲基酚、2,4,6-三-第三丁基酚、2,4-二辛硫基甲基-6-甲基酚、2,2’-硫雙(6-第三丁基酚)、4,4’-硫雙(3-甲基-6-第三丁基酚)、2,2’-亞甲基雙(4-甲基-6-第三丁基酚)、2,2’-亞甲基雙(4-乙基-6-第三丁基酚)、2,2’-亞甲基雙[4-甲基-6-(α-甲基環己基)酚]、2,2’-亞甲基雙(4-甲基-6-環己基酚)、2,2’-亞甲基雙(4,6-二-第三丁基酚)、2,2’-亞乙基雙(4,6-二-第三丁基酚)、4,4’-亞甲基雙(6-第三丁基-2-甲基酚)、4,4’-亞甲基雙(2,6-二-第三丁基酚)、4,4’-亞丁基雙(3-甲基-6-第三丁基酚)、1,1-雙(4-羥基苯基)環己烷、1,1-雙(5-第三丁基-4-羥基-2-甲基苯基)丁烷、1,1,3-三(5-第三丁基-4-羥基-2-甲基苯基)丁烷、乙二醇雙[3,3-雙-3’-第三丁基-4’-羥基苯]丁酸酯];2,4,6-三(3,5-二-第三丁基-4-苯氧基)-1,3,5-三、參(4-第三丁基-3-羥基-2,6-二甲基苯甲基)異三聚氰酸酯、雙(3,5-二-第三丁基-4-羥基苯甲基)異三聚氰酸酯、參[2-(3’,5’-二-第三丁基-4’-羥基桂皮醯氧基)乙基]異三聚氰酸酯、3,5-二-第三丁基-4-羥基苯甲基膦酸二乙酯、3,5-二-第三丁基-4-羥基苯甲基膦酸二(正十八烷酯)、3,5-二-第三丁基-4-羥基苯甲基膦酸單酯鈣鹽、3-(3,5-二-第三丁基-4-羥基苯基)丙酸正十八烷酯、新戊四醇肆(3,5-二-第三丁基-4-羥基桂皮酸酯)、硫二伸乙基雙(3,5-二-第三丁基-4-羥基桂皮酸酯)、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苯甲基)苯、3,6-二氧雜(1,8-伸辛基)雙(3,5-二-第三丁基-4-羥基桂皮酸酯)、六亞甲基雙(3,5-二-第三丁基-4-羥基桂皮酸酯)、三乙二醇雙(5-第三丁基-4-羥基-3-甲基桂皮酸酯)、3,9-雙[2-(3-(3-第三丁基-4-羥基-5-甲基苯基)丙醯基氧)-1,1-二甲基乙基]-2,4,8,10-四氧雜螺[5‧5]十一烷、N,N’-雙[3-(3’,5’-二-第三丁基-4’-羥基苯基)丙醯基]聯胺、N,N’-雙[3-(3’,5’-二第三丁基-4’-羥基苯基)丙醯基]六亞甲基二胺、丙烯酸2-第三丁基-6-(3’-第三丁基-5’-甲基-2’-羥基苯甲基)-4甲基苯酯、丙烯酸2,4-二-第三戊基-6-[1-(2-羥基-3,5-二-第三戊基苯基)乙基]苯酯、及其混合物;此等酚系抗氧化劑,可單獨使用或使用兩種或多種。
尤其,以丙烯酸2-第三丁基-6-(3’-第三丁基-5’-甲基-2’-羥基苯甲基)-4-甲基苯酯、丙烯酸2,4-二-第三戊基-6-[1-(2-羥基-3,5-二-第三戊基苯基)乙基]苯酯、及其混合物為更佳。
本發明的組成物為含該安定劑及熱塑性聚合物之熱塑性聚合物組成物。
熱塑性聚合物的實例包含聚丙烯系樹脂如乙烯-丙烯共聚物、聚乙烯系樹脂(高密度聚乙烯(HD-PE)、低密度聚乙烯(LD-PE)、直鏈低密度聚乙烯(LLDPE)等)、甲基戊烯聚合物、乙烯-丙烯酸乙酯共聚物、乙烯-乙酸乙烯酯共聚物、聚苯乙烯(如聚(對-甲基苯乙烯)、聚(α-甲基苯乙烯)、丙烯腈-苯乙烯共聚物、丙烯腈-丁二烯-苯乙烯共聚物、特殊丙烯酸橡膠-丙烯腈-苯乙烯共聚物,丙烯腈-氯化聚乙烯-苯乙烯共聚物、苯乙烯-丁二烯共聚物等)、氯化聚乙烯、聚氯平、氯化橡膠、聚氯乙烯、聚偏二氯乙烯、甲基丙烯酸樹脂、乙烯-乙烯醇共聚物、氟樹脂、聚縮醛、接枝的聚苯醚樹脂、聚苯硫醚樹脂、聚胺基甲酸酯、聚醯胺、聚酯樹脂(例如,聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯等)、聚碳酸酯、聚丙烯酸酯、聚碸、聚醚醚酮、聚醚碸、芳族聚酯樹脂、苯二甲酸二烯丙酯預聚物、矽氧樹脂、1,2-聚丁二烯、聚異戊二烯、丁二烯/丙烯腈共聚物、以及乙烯-甲基丙烯酸甲酯共聚物。尤其,就良好加工性能而言,以聚乙烯系樹脂、聚丙烯系樹脂和聚苯乙烯類為佳,且其中,聚丙烯系樹脂、丙烯腈-丁二烯-苯乙烯共聚物、以及苯乙烯-丁二烯共聚物為佳。
本文中,聚丙烯系樹脂意指含有衍生自丙烯之結構單元的聚烯烴,且具體而言,例如,包含結晶聚丙烯均聚物、丙烯-乙烯無規共聚物、丙烯-α-烯烴無規共聚物、丙烯-乙烯-α-烯烴共聚物、以及丙烯系嵌段共聚物(由丙烯均聚物成份或主要由丙烯所構成的共聚物成分、以及丙烯、乙烯及/或α-烯烴的共聚物成分所構成)。
當丙烯系樹脂用作本發明之熱塑性聚合物時,可使用一種聚丙烯系樹脂或將兩種或多種丙烯系樹脂摻混使用。
通常,α-烯烴為4至12個碳的α-烯烴,且其實例包含1-丁烯、1-戊烯、1-己烯、4-甲基-1-戊烯、1-辛烯、及1-癸烯,並以1-丁烯、1-己烯扣1-辛烯為佳。
丙烯-α-烯烴無規共聚物的實例包含丙烯-1-丁烯無規共聚物、丙烯-1-己烯無規共聚物、及丙烯-1-辛烯無規共聚物。
丙烯-乙烯-α-烯烴共聚物的實例包含丙烯-乙烯-1-丁烯共聚物、丙烯-乙烯-1-己烯共聚物、及丙烯-乙烯-1-辛烯共聚物。
由丙烯均聚物成份或主要由丙烯所構成的共聚物成分、以及丙烯、乙烯及/或α-烯烴的共聚物成分所構成的共聚物成分包含丙烯-乙烯共聚物成分、丙烯-1-丁烯共聚物成分、及丙烯-1-己烯共聚物成分,丙烯、乙烯及/或α-烯烴之的共聚物成分包含丙烯-乙烯共聚物成分、丙烯-乙烯-1-丁烯-共聚物成分、丙烯-乙烯-1-己烯共聚物成分、丙烯-乙烯-1-辛烯成分、丙烯-1-丁烯共聚物成分、丙烯-1-己烯共聚物成分、以及丙烯-1-辛烯共聚物成分。在丙烯、乙烯及/或α-烯烴的共聚物成分中,乙烯及/或4至12個碳的α-烯烴的含量為0.01至20wt%。
此外,由丙烯均聚物成分或主要由丙烯所構成的共聚物成分、以及丙烯、乙烯及/或α-烯烴的共聚物成分所構成的聚丙烯系嵌段共聚物之實例包含丙烯-乙烯嵌段共聚物、(丙烯)-(丙烯-乙烯)嵌段共聚物、(丙烯)-(丙烯-乙烯-1-丁烯)嵌段共聚物、(丙烯)-(丙烯-乙烯-1-己烯)嵌段共聚物、(丙烯)-(丙烯-1-丁烯)嵌段共聚物、(丙烯)-(丙烯-1-己烯)嵌段共聚物、(丙烯-乙烯)-(丙烯-乙烯-1-丁烯)嵌段共聚物、(丙烯-乙烯)-(丙烯-乙烯-1-己烯)嵌段共聚物、(丙烯-乙烯)-(丙烯-1-丁烯)嵌段共聚物、(丙烯-乙烯)-(丙烯-1-己烯)嵌段共聚物、(丙烯-1-丁烯)-(丙烯-乙烯)嵌段共聚物、(丙烯-1-丁烯)-(丙烯-乙烯-1-丁烯)嵌段共聚物、(丙烯-1-丁烯)-(丙烯-乙烯-1-己烯)嵌段共聚物、(丙烯-1-丁烯)-(丙烯-1-丁烯)嵌段共聚物、及(丙烯-1-丁烯)-(丙烯-1-己烯)嵌段共聚物。
當聚丙烯系樹脂用作本發明之熱塑性聚合物時,以由結晶之丙烯均聚物,或者由丙烯均聚物成分所構成的聚丙烯系嵌段共聚物或主要由丙烯及丙烯、乙烯及/或4至12個碳的α-烯烴的共聚物成分所構成的共聚物成分所構成的聚丙烯系嵌段共聚物為佳。更佳地為由丙烯均聚物成份所構成的聚丙烯系嵌段共聚物,或者主要由丙烯、及丙烯、乙烯及/或4至12個碳的α-烯烴之共聚物成分所構成的共聚物成分所構成的聚丙烯系嵌段共聚物。本發明之熱塑性聚合物組成物,相對於每100重量份熱塑性聚合物,通常含有5重量份或更少的本發明安定劑就已足夠,特定而言,該組成物含有0.0001重量份至5重量份的安定劑,較佳地為0.0005重量份至3重量份的安定劑。當安定劑的含量為5重量份或更少時,所謂的滲出現象,即安定劑出現在熱塑性聚合物組成物之表面,將受到壓制,故而較佳。
本發明之製備熱塑性聚合物組成物的方法包含:乾式摻混(dry-blending)熱塑性聚合物和安定劑,以單軸或多軸押出機熔融捏合(melt-kneading)該摻混物以及模壓出此摻混物以得到粒狀之熱塑性聚合物組成物的方法;以及將本發明之安定劑溶解於溶劑(如環己烷)之溶液與熱塑性聚合物溶液(如聚合物之聚合反應後的熱塑性聚合物溶液)混合,並蒸餾出該溶劑而得到熱塑性聚合物組成物的方法。
含有本發明之化合物(1)的安定劑給予熱塑性聚合物熱安定性。本文中,可藉由下列方式評估含有熱塑性聚合物和該安定劑的熱塑性聚合物之熱安定性:在180℃加熱該含有熱塑性聚合物和該安定劑的熱塑性聚合物組成物並予以熔化,使用如JIS K7105之色度計測量黃化指數(YI),接著,在180℃復加熱該組成物2小時,在加熱後測量該組成物之YI值,並藉由該組成物於加熱前後之YI值差異評估熱安定性。當測得的YI值差異較小時,不易引起熱變質所導致的變色,亦即熱安定性越好。
下述實施例和比較例將更詳細地說明本發明,但不應以該等實施例限制本發明。
混和2,4-二-第三戊基酚(117.5g)、0.9g的對甲苯磺酸單水合物以及6.9g的78%硫酸水溶液。在該混合物中,滴加經由28g之二甲苯稀釋12.1g乙醛所得的溶液歷時2小時並維持在35至45℃。添加之後,升高該所得溶液的溫度至90℃,且維持該相同溫度3小時。
維持該溫度之後,添加157g的二甲苯、59g的水以及11.7g的25%氫氧化鈉水溶液,使其分層並移除該水層。以水清洗所得的油層,並進行共沸脫水移除水分。脫水後,得到292g之淡黃色之含有式(2)所示之雙酚。
添加28g的50%氫氧化鉀水溶液至含雙酚之淡黃色油,升高該溶液的溫度至98℃,且維持該溶液相同溫度3小時。之後,使該溶液冷卻至50℃,添加己烷,且在加溫至液體溫度106℃的條件下脫水,並冷卻至3℃(此溶液標記為A溶液)。
於另一容器填入35.3g的丙烯酸羧乙酯,並在攪拌下冷卻至1℃。接著將26.7g的亞硫醯氯經1.5小時滴加至其中並維持在0至1℃。之後,升溫至1至17℃歷3小時,接著減壓下除氣3小時(此溶液標記為B溶液)。
將B溶液經1小時滴加至A溶液中,同時維持溫度在1至3℃,並維持相同溫度30分鐘。在其中添加150ml的水,在10至30℃以水清洗該混和溶液,且根據相同程序,藉由分層以得到該油層,重複以水清洗3次。藉此,得到303g之褐色油層。
當所得的油層以液相層析分析時,發現除了溶劑外,該組成物含有6.3wt%之式(1-1)所示的化合物(下文中,在某些情況被稱為化合物(1-1))。
以使用Sumipax ODS A-210(直徑20mm×高25cm,填料直徑為5μm)作為管柱之大規模收集系統(Shimadzu公司所製造之8A型)自所得的油層分離化合物(1-1)。
使用JEOL所製造的ECA-500並採用四甲基矽烷作為內標準測量化合物(1-1)的1
H NMR光譜。
1
H NMR(500.16MHz,CDCl3
)δ(ppm):0.49(3H,(a)),0.55(3H,(b)),0.66(3H,(c)),0.70(3H,(d)),1.01(3H,(e)),1.03(3H,(f)),1.19-1.38(23H,(g)-(1)),1.48(3H,(m)),1.57-1.99(7H,(n)-(p)),3.09(2H,(q)),3.89(1H,(r)),4.61-4.64(2H,(s)),5.55(1H,(t)),5.72(1H,(u)),6.04(1H,(v)),6.36(1H,(w)),6.49(1H,(x)),7.12(3H,(y))
使用實施例1中所得之化合物(1-1)(11.6m2)作為熱安定劑,並將其溶解於5ml之氯仿。在該所得溶液中添加作為熱塑性聚合物之2000mg之丙烯-乙烯嵌段共聚物(MI:9至10g/10分鐘)(230℃,2.16kg)(SUMITOMO CHEMICAL有限公司所製造),並攪拌該混合物,且氯仿在25℃自然地蒸發。此外,以耐熱試驗爐(gear oven,Tabai Espec公司製造之GHPS-222)在180℃加熱並熔化殘餘物1小時以得到熱塑性聚合物組成物。
根據JIS K7105,使用色度計(Konika Minolta所製造的CM-3500d)測量實施例1所得熱塑性聚合物組成物的黃化指數(YI)值(YI-1),在180℃以耐熱試驗爐(Tabai Espec公司製造之GHPS-222)加熱該組成物2小時,以再次測量YI值(YI-2),且採用YI-2與YI-1的差值作為變色程度,並用以評估該熱塑性聚合物組成物的熱安定性。當變色程度較小時,難以引起因熱塑性聚合物組成物之熱降解所造成的變色,亦即熱安定性較佳。實施例1之該熱塑性聚合物組成物的變色程度為10.03。
令不含該安定劑的熱塑性聚合物(比較例描述於下文中)的變色程度作為100%,改善的變色程度(變色程度減少率)以變色程度改善指數來表示。亦即,因為實施例1的變色程度改善指數為(13.15-10.03)/13.15×100=23.7(%),是以,相較於不含該安定劑的熱塑性聚合物組成物,實施例1的熱塑性聚合物組成物改善23.7%。
根據<熱塑性聚合物組成物之製備例>之相同方法得到熱塑性聚合物組成物,但不使用實施例1得到的化合物(1-1)。
根據實施例1之相同方法,但係使用所得之熱塑性聚合物組成物,並測定該熱塑性聚合物組成物的熱安定性。測得的結果與實施例1的結果顯示於表1。
除了使用11.6mg的丙烯酸2,4-二-第三戊基-6-[1-(3,5-二-第三戊基-2-羥基苯基)乙基]苯基酯(Sumilizer GS,由SUMITOMO CHEMICAL有限公司所製造,下文中,於某些情況被稱為化合物A)取代實施例1所得到的化合物(1-1)之外,如實施例2之相同方法得到熱塑性聚合物組成物。
除了係使用該所得的熱塑性聚合物組成物之外,如實施例1之相同方法,測定熱安定性。測得的結果以及實施例1和比較例1之結果示於表1中。
本發明之化合物可進一步改善熱塑性聚合物的熱安定性。
Claims (6)
- 一種如式(1)所示之雙酚單酯化合物:
- 一種安定劑,包括如申請專利範圍第1項之雙酚單酯化合物作為活性成分。
- 如申請專利範圍第2項之安定劑,其中,該安定劑包含0.005wt%至100wt%之如申請專利範圍第1項之該雙酚單酯化合物。
- 一種熱塑性聚合物組成物,包括如申請專利範圍第2或3項之安定劑、以及熱塑性聚合物。
- 一種如申請專利範圍第2或3項之安定劑的用途,係用於熱安定化熱塑性聚合物。
- 一種製造如申請專利範圍第1項之雙酚單酯化合物的方法,包括使式(2)所示之雙酚:
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