TW201708371A - 具改良低溫性質及良好耐油性之丙烯酸酯橡膠,由其製得之可硫化混合物及硫化物 - Google Patents
具改良低溫性質及良好耐油性之丙烯酸酯橡膠,由其製得之可硫化混合物及硫化物 Download PDFInfo
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- TW201708371A TW201708371A TW105113294A TW105113294A TW201708371A TW 201708371 A TW201708371 A TW 201708371A TW 105113294 A TW105113294 A TW 105113294A TW 105113294 A TW105113294 A TW 105113294A TW 201708371 A TW201708371 A TW 201708371A
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- Prior art keywords
- acrylate
- copolymer
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- weight
- diyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 229920001971 elastomer Polymers 0.000 title claims description 22
- 239000005060 rubber Substances 0.000 title claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 16
- 229920001577 copolymer Polymers 0.000 claims abstract description 58
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005977 Ethylene Substances 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 238000004132 cross linking Methods 0.000 claims abstract description 14
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 10
- -1 Propane-1,2-diyl Chemical group 0.000 claims description 41
- 239000000178 monomer Substances 0.000 claims description 37
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 16
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- 238000004073 vulcanization Methods 0.000 claims description 13
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 12
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 12
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 5
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- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 4
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- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- JZQAAQZDDMEFGZ-UHFFFAOYSA-N bis(ethenyl) hexanedioate Chemical compound C=COC(=O)CCCCC(=O)OC=C JZQAAQZDDMEFGZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 2
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- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
本發明涉及丙烯酸烷基酯、特定不飽和羧酸酯和選擇性地乙烯的共聚物之用途,該等共聚物具有低玻璃轉化溫度同時具有高耐油性,其係用於製造可硫化混合物及其交聯以及由其獲得的硫化物和成形物件。
Description
丙烯酸酯單體的聚合物和乙烯與丙烯酸酯單體的共聚物,尤其丙烯酸酯橡膠(ACM)和乙烯-丙烯酸酯共聚物(AEM)係大規模製造的橡膠,例如藉由自由基交聯或借助於主鏈嵌入的固化位點(cure-site)單體的交聯,可以從該等橡膠製造硫化物(vulcanizates),該等硫化物的突出之處尤其在於良好的耐油性和耐介質性以及出色的耐老化性。
然而,當前在市場上可獲得的ACM和AEM橡膠並不充分滿足良好的低溫可撓性(low-temperature flexibility)與低的油溶脹性(Oil Swell)之組合,因為耐油性的改良迄今為止僅在低溫可撓性劣化的同時才是可能的。在AEM和ACM橡膠通常地展現出在玻璃轉化溫度和油溶脹性之間的聯繫,其中當所使用的丙烯酸酯的極性增加,該油溶脹性降低,然而同時玻璃轉化溫度升高,反之亦然。在藉由嵌入不同的額外的共聚單體下,實現在保持相同的油溶脹性下降低玻璃轉化溫度或者在保持相同的玻璃轉化溫度下降低油溶脹性的嘗試,在過去沒有獲得足夠的成功。
在文獻中,描述了用於改良ACM和AEM橡膠的低溫性質的
不同的手段。
加入可塑劑來改良ACM和AEM硫化物的低溫性質為一種可能性。然而,尤其在改良低溫性質方面最有效的可塑劑,例如像Rhenosin 759、己二酸二辛酯(DOA)、癸二酸二辛酯(DOS)或者例如像乙醯基檸檬酸三(2-乙基己基)酯或乙醯基檸檬酸三丁基酯等檸檬酸酯係相對揮發性的並且因而經常導致在硫化物的熱老化時的問題,這在ACM和AEM的情況下是特別成問題的,因為該等橡膠較佳的是在高溫應用中使用。此外,可以添加的可塑劑的量係受限的,因為否則就不再能達到所要求的硬度及/或其他硫化物性質,例如像斷裂拉伸率(elongation at break)和/或拉伸強度(tensile strength)。此外,由於可塑劑的滲出(exudation)、可塑劑從硫化物中遷移(migration)出來或其抽取(extraction)而進一步產生問題。因此,而非僅使用可塑劑,其較佳係降低所使用橡膠的玻璃轉化溫度:調配者(formulator)在自由選擇可塑劑及其劑量的情況下混合物形成物一方面獲得更多的可撓性,或者可以在需要時甚至完全省去可塑劑的添加,因而不需要接受在硫化物的低溫性質或在熱老化之犧牲。另一方面,可以藉由具有該更低玻璃轉化溫度的改良橡膠與適合的可塑劑的組合,可額外地再次向下擴展橡膠及/或由其製造的硫化物的使用溫度範圍。
AEM橡膠係已知的大規模製造的橡膠,該等橡膠具有良好的耐油性、良好的熱穩定性以及出色的UV穩定性。可商購的共聚物由乙烯、丙烯酸甲基酯、丙烯酸丁基酯或類似的丙烯酸烷基酯和選擇性地其他的固化位點單體如富馬酸單烷基酯或馬來酸單烷基酯來構造。通常,乙烯-丙烯酸酯橡膠在高壓方法中在900至2800bar的壓力下製造並且在超過100℃的溫度下聚合。於是,US 2599123描述了在這些條件下利用批次(batch)方法製造乙烯-丙烯酸甲基酯-馬來酸單烷基酯共聚物。在聚合過程
中溶劑(如甲醇)的添加,如在US 4026851中所描述的,減少了所使用的反應器的停留時間(on-stream times)。通常,可商購的乙烯-丙烯酸酯橡膠係過氧化物式或用聚胺或氨基甲酸酯化二胺(carbamated diamine)如DIAK No.1來交聯。這例如是在US3883472或US40226851中呈現的。
在EP 1654687中描述的,藉由使用丙烯酸烷基酯、尤其丙烯酸丁基酯作為其他的單體,改良了低溫可撓性,然而同時藉由使用極性更低的單體提高了油溶脹性。因此,在保留良好的油溶脹性的同時充分改良低溫可撓性係迄今為止在用於AEM的先前技術中未知的。
ACM橡膠在乳液方法中製造並且由不同丙烯酸酯的混合物組成。最常用的單體係丙烯酸乙基酯和丙烯酸丁基酯,大多數情況與適合的固化位點單體相結合,如乙酸氯乙烯酯、氯乙基乙烯基醚、4-乙烯基苄基氯、甲基丙烯酸縮水甘油酯、丙烯酸、馬來酸單烷基酯或富馬酸單烷基酯。為了能夠改善低溫性質,如在EP 905182中描述的,將丙烯酸2-甲氧基乙基酯聚合入其中。總體上,在此更長的烷基可以改善耐寒性,然而由此損害了耐油性。更短的烷基於是顯示出相反的效果。丙烯酸烷氧基酯改良了耐寒性以及耐油性,在此存在對於進一步改良耐寒性的額外的要求。
J.-F.Lutz等人例如在J.Polym.Sci.,Polym.Chem.2008,46,3459和Macromolecules 2006,39,893中描述了聚合甲基丙烯酸聚乙二醇酯來合成具有更高的、部分依賴于溫度的水溶性的聚合物。沒有描述甲基丙烯酸聚乙二醇酯與乙烯和/或其他丙烯酸酯的共聚物。
在DE 19942301中,描述了由丙烯酸烷基酯、乙烯基芳香族和聚乙氧基丙烯酸烷基酯所構成聚合物之製造。所製造的聚合物用作可重分散(redispersible)的水泥改性劑。利用所獲得的聚合物用於製造可硫化混合物(vulcanizable mixtures)和硫化物之用途並未被公開,對於硫化物本
身及其性質的改良也是同樣情況。
本發明之目的在於,提供丙烯酸酯聚合物以及乙烯和丙烯酸酯的共聚物,及其用於製造可硫化混合物和硫化物之用途,它們避免了先前技術的缺點並且具有與高的耐油性相組合的改良的低溫性質,其中較佳的是應當避免老化性質的劣化。
所述之目的藉由包含以下各項的共聚物來實現:i)49至99重量%、較佳的是55至90重量%的衍生自至少一種丙烯酸烷基酯的重複單元,該重複單元與重複單元ii)不同,ii)1至51重量%的衍生自至少一種具有通式(I)之單體的重複單元CH2=C(R1)(COO(R2O)nR3) (I)
其中R1 代表氫或甲基,R2 分別彼此獨立地代表直鏈或分支的C2至C6-烯基R3 代表氫,未取代或用C1-C3烷基取代的苯基,直鏈或分支的C1-C8烷基或-C(=O)R4,R4 代表氫或直鏈或分支的C1-C8烷基,並且n 代表2至30的數字,以及iii)0至50重量%、較佳的是0至45重量%的衍生自乙烯的重複單元,其中該等量分別相對於重複單元i)至iii)的總量。
因此“共聚物”在本發明意義上理解為如下聚合物:包含兩種或更多不同單體的共聚單元(copolymerized units),其中本發明之聚合物
包含三種或更多不同單體的共聚單元。
適合用於引入重複單元i)的、與重複單元ii)不同的丙烯酸烷基酯較佳的是選自具有1至10個碳原子的烷基的丙烯酸酯,如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸異丙酯、丙烯酸正丁酯、丙烯酸正己酯、丙烯酸3-丙基庚酯、丙烯酸2-乙基己酯、丙烯酸正辛酯,以及該等丙烯酸酯的混合物,特別較佳的是丙烯酸甲酯、丙烯酸乙酯和丙烯酸正丁酯以及該等丙烯酸酯的混合物。
通式(I)的單體具有部分R2,該等部分獨立於彼此地選自包含以下項之群組乙烷-1,2-二基,丙烷-1,3-二基,丙烷-1,2-二基,丁烷-1,4-二基,丁烷-1,3-二基,戊烷-1,3-二基,戊烷-1,4-二基,戊烷-1,5-二基和2-甲基丁烷-1,4-二基,較佳的是乙烷-1,2-二基,丙烷-1,3-二基,丙烷-1,2-二基和丁烷-1,4-二基,特別較佳的是乙烷-1,2-二基和丙烷-1,2-二基。表達“獨立於彼此地”在此表明,在一個分子中可以包含不同的部分R2。由此產生的不同的R2O單元在此可以在該分子的聚醚鏈中任意地按隨機式、交替式、或嵌段式排列。
通式(I)的分子的部分R3選自包含以下項之群組:H,CH3,CH2CH3,CH2CH2CH3,CH2CH2CH2CH3,CHO,COCH3,COCH2CH3,COCH2CH2CH3和COCH2CH2CH2CH3,較佳的是選自包含以下項之群組:H,CH3,CH2CH3和COCH3,並且特別較佳的是選自包含以下項之群組:CH3,CH2CH3和COCH3。作為通式(I)之單體可以使用通式(I)的多種不同單體的混合物,該等單體例如在部分R1、R2和/或R3中或者在重複單元的數量“n”中有所不同。
通式(I)之單體的實例係丙烯酸聚乙二醇酯,甲基丙烯酸聚乙二醇酯,丙烯酸聚丙二醇酯,甲基丙烯酸聚丙二醇酯,混合的丙烯酸聚(乙二醇丙二醇)酯或甲基丙烯酸聚(乙二醇丙二醇)酯,或者丙烯酸聚(THF)酯
或甲基丙烯酸聚(THF)酯。特別較佳的是甲氧基或乙氧基封端的丙烯酸聚乙二醇酯或甲基丙烯酸聚乙二醇酯、甲氧基或乙氧基封端的丙烯酸聚丙二醇酯或甲基丙烯酸聚丙二醇酯,具有2至25個乙二醇或丙二醇重複單元,非常特別較佳的是具有2至20乙二醇或丙二醇重複單元。
通式(I)的重複單元的含量較佳的是2至40重量%、特別較佳的是4至25重量%並且大多數情況下較佳的是6至20重量%,分別基於重複單元i)至iii)的總和。
在一個較佳的實施方式中,衍生自乙烯的重複單元的比例大於5重量%、較佳的是大於10重量%並且特別較佳的是大於20重量%,分別基於重複單元i)至iii)的總量。
本發明之共聚物還可以具有一種或多種額外的共聚單體(iv),也就是說並未落在上述對重複單元i)至iii)的單體的定義中的共聚物,並且尤其以少於25重量%、較佳的是少於20重量%、還較佳的是少於15重量%、仍進一步較佳的是少於10重量%、特別較佳的是少於5重量%且非常特別較佳的是少於1重量%的總量,分別基於重複單元i)至iii)和該一種或多種額外的共聚單體(iv)的總量。
該等其他的單體(iv)典型地選自包含以下項之群組:含環氧基的丙烯酸酯,含環氧基的甲基丙烯酸酯,具有2至8個碳原子的烷氧基烷基的丙烯酸烷氧基烷基酯,乙烯基酮,乙烯基芳香族化合物,共軛二烯,α-單烯烴,具有羥基的乙烯基單體,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,丙烯酸,甲基丙烯酸,偏氟乙烯,六氟丙烯,偏氯乙烯,四氟乙烯,四氯乙烯,氯乙烯,不飽和醯胺單體和一氧化碳以及該等單體的混合物,較佳的是選自丙烯酸甲酯,丙烯酸乙酯,丙烯酸丙酯,丙烯酸正丁酯,丙烯酸2-乙基己酯,丙烯酸正辛酯,甲基丙烯酸縮水甘油酯,己二酸
二乙烯酯,甲基乙烯基酮,乙基乙烯基酮,苯乙烯,α-甲基苯乙烯,乙烯基甲苯,丁二烯,異戊二烯,丙烯,1-丁烯,丙烯酸β-羥乙基酯,丙烯酸4-羥丁基酯,丙烯酸3-氰基乙基酯,丙烯醯胺,N-甲基甲基丙烯醯胺,丙烯酸2-甲氧基乙基酯,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,一氧化碳以及該等單體的混合物,並且特別較佳的是選自丙烯酸,甲基丙烯酸,丙烯酸2-甲氧基乙基酯,甲基丙烯酸縮水甘油酯,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,一氧化碳以及該等單體的混合物。
在一個特別較佳的實施方式中,本發明之共聚物為包含衍生自乙烯、丙烯酸甲酯和具有2至20個乙二醇和/或丙二醇重複單元的含聚伸烷基二醇的(甲基)丙烯酸酯的重複單元的共聚物。在其他的較佳的實施方式中,還包含衍生自丙烯酸丁酯、馬來酸單烷基酯和/或富馬酸單烷基酯的重複單元。
在一個特別較佳的實施方式中,本發明之共聚物為包含衍生自至少兩種丙烯酸烷基酯,較佳的是丙烯酸乙酯和丙烯酸丁酯,和具有2至20個乙二醇和/或丙二醇重複單元的含聚伸烷基二醇的(甲基)丙烯酸酯的重複單元的共聚物。在其他的較佳的實施方式中,還包含衍生自(甲基)丙烯酸、甲基丙烯酸縮水甘油酯、乙酸氯乙烯酯、馬來酸單烷基酯、富馬酸單烷基酯的重複單元。
一個非常特別較佳的實施方式包含,分別基於重複單元i)和ii),至少10重量%的丙烯酸乙酯,至少10重量%的丙烯酸丁酯,最高達20重量%的式(I)之單體,以及最高達10重量%、較佳的是最高達5重量%的選自下組的其他單體,該組包含:含環氧基的丙烯酸酯,含環氧基的甲基丙烯酸酯,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,丙烯酸,甲基丙烯酸,偏氯乙烯,氯乙烯以及該等單體的混合物。
在本發明之共聚物中,單體隨機式分佈、交替式分佈、或者嵌段式分佈,較佳的是隨機式分佈。
本發明之共聚物的玻璃轉化溫度典型地處於+10℃至-50℃的範圍內、較佳的是在0℃至-45℃的範圍內,並且特別較佳的是在-5℃至-40℃的範圍內(借助於DSC以20K/min的加熱速率測量)。
本發明的另一個主題係用於製造本發明之共聚物之方法,其中將丙烯酸酯、通式(I)之單體和選擇性地一種或多種額外的單體(iv)自由基聚合。
在一個較佳的實施方式中,用於製造本發明之共聚物之方法如下地執行,使得在聚合反應開始之後,將通式(I)之單體添加到反應混合物。反應混合物可以在聚合反應開始時已經包含通式(I)之單體的總使用量的一部分或者可以在聚合反應開始之後才把全部通式(I)之單體投入。
本發明還涉及包含本發明的聚合物和選擇性地一種或多種交聯劑的可硫化混合物。後者對於借助於輻射交聯來硫化的組成物而言是不需要的。表達混合物和組成物在本申請中可以看做同義的。
作為交聯劑例如可以考慮過氧化物型交聯劑,如雙(2,4-二氯苄基)過氧化物,二苯甲醯過氧化物,雙(4-氯苯甲醯)過氧化物,1,1-雙-(三級丁基過氧基)-3,3,5-三甲基環己烷,過氧苯甲酸三級丁基酯,2,2雙(三級丁基-過氧基)丁烯,戊酸4,4-二-三級丁基過氧基壬基酯,二異丙苯基過氧化物,2,5-二甲基-2,5-二(三級丁基-過氧基)己烷,1,3-雙(三級丁基過氧基異丙基)苯,二-三級丁基過氧化物和2,5-二甲基-2,5-二(三級丁基過氧基)-己炔-3。這種或該等交聯劑的總量通常處於0.5至15phr的範圍內,較佳的是處於1至10phr的範圍內並且特別較佳的是處於1.5至6phr的範圍內,基於本發明
之共聚物。在此可以較佳的是使用負載的過氧化物,其中所給出的量必須校正載體的量。
可以較佳的是,除了這種過氧化物交聯之外,還使用額外的添加劑,即所謂的助劑,借助該等添加劑能夠提高交聯的產率。適合於此的例如是異氰酸三烯丙基酯,氰酸三烯丙基酯,三甲基丙烯酸三甲氧基丙烷酯,苯三甲酸三烯丙基酯,二甲基丙烯酸乙二醇酯,二甲基丙烯酸丁二醇酯,三丙烯酸三甲氧基丙烷酯,二丙烯酸鋅,二甲基丙烯酸鋅,1,2-聚丁二烯或N,N’-間伸苯基二馬來醯亞胺。這種或該等助劑的總量通常處於0.2至10phr的範圍內,較佳的是處於0.4至4phr的範圍內並且特別較佳的是處於0.6至2phr的範圍內,基於本發明之共聚物。在此還可以使用負載的化合物,其中所給出的量必須校正載體的量。
替代於過氧化物交聯,在環氧官能的情況下,本發明之共聚物可以包含(例如像能夠藉由使用甲基丙烯酸縮水甘油酯作為額外單體加入時)還藉由添加多元酸或多元酸酐以及適合的加速劑來執行的交聯。作為多元酸可以使用例如戊二酸或己二酸,並且作為加速劑可以使用溴化四丁基銨。
在富馬酸或馬來酸單烷基酯的情況下包含的共聚物大多數情況下用脂肪族或芳香族的二胺化合物作為硫化劑以及鹼作為硫化加速劑來進行加工。脂肪族或芳香族的二胺化合物包含例如六亞甲基二胺,胺基甲酸六亞甲二胺酯,4,4’-亞甲基二苯胺,間伸苯基二胺,4,4’-二胺二苯基醚,對伸苯基二胺,p,p’-伸乙基二苯胺,4,4’-(對伸苯基二異丙基)二苯胺,4,4’-(間伸苯基二異丙基)二苯胺,3,4’-二胺基二苯基醚,4,4’-二胺基二苯基碸,2,2-雙[4-(4-胺基苯氧基)苯基)丙烷,雙[4-(4-胺基苯氧基)苯基]碸,雙[4-(3-胺基苯氧基)苯基]碸,4,4’雙(4-胺基苯氧基)聯苯,雙[4-(4-胺基苯氧基)苯基]醚,
2,2-雙[4(4-胺基苯氧基)苯基]六氟丙烷,1,4-雙(4-胺基苯氧基)苯和1,3-雙(4-胺基苯氧基)苯,其中較佳的是對二胺基取代的化合物和胺基甲酸六亞甲二胺酯。二胺化合物以約0.1至約5phr、較佳的是約0.2至約4phr、特別較佳的是約0.5至約3phr的量使用。低於約0.1phr則硫化不充分並且不能獲得在壓縮應力下足夠的性質,相反,超過約5重量份數造成預交聯以及硫化的消失。作為鹼可以例如使用胍,或者雙-或多環的胺類鹼,如1,8-二氮雜二環[5.4.0]十一-7-烯(DBU),1,5-二氮雜二環[4.3.0]-5-壬烯(DBN),1,4-二氮雜二環[2.2.2]辛烷(DABCO),1,5,7-三氮雜二環[4.4.0]癸-5-烯(TBD),7-甲基-1,5,7-三氮雜二環[4.4.0]癸-5-烯(MTBD)及其衍生物。同樣可以使用該等化合物的混合物。該等化學品能夠以純形式或預分散的形式使用。在預分散的化學品的情況下,尤其可以使用聚乙烯蠟或者乙烯-乙烯基乙酸酯共聚物作為載體材料。另外,鹼也可以按質子化的形式,例如具有甲酸根或乙酸根作為平衡離子。
可使用的胍的清單除胍之外還包含二苯基胍(DPG),四甲基胍,四乙基胍,N,N’-二-鄰甲苯基胍(DOTG)等等,其中二苯基胍和N,N’-二-鄰甲苯基胍是較佳的。該鹼以約0.1至約10phr、較佳的是約0.3至約6phr、特別較佳的是約0.5至約4phr的量使用。
在帶有含鹵素或含鹵素和羧基的重複單元的聚合物的情況下,尤其可以使用硫、三如2,4,6-三巰基-S-三,或者三硫氰酸如1,3,5-三-2,4,6-三硫醇作為硫化劑。作為加速劑尤其可以使用例如像1,3-二鄰甲苯基胍或二苯基胍,秋蘭姆(thiuram)或秋蘭姆多硫化物例如像二五亞甲基秋蘭姆二硫化物,或四丁基秋蘭姆二硫化物,脲衍生物例如像N,N’-二乙基硫脲或N,N’-二甲基硫脲,達有龍(diuron),鹵化四烷基銨如溴化十八烷基三甲基銨,溴化鯨蠟基三甲基銨或者溴化四丁基銨,羧酸鹽例如像硬
脂酸鈉或硬脂酸鉀或苯甲酸銨,硬脂酸,二硫代胺基甲酸酯或其鹽例如像二甲基二硫代胺基甲酸鋅,二乙基二硫代胺基甲酸鋅,二丁基二硫代胺基甲酸鋅或者二甲基二硫代胺基甲酸鐵,以1至15phr、較佳的是以1.5至10phr的量。硫化劑可以單獨地或組合地使用。
替代於這種交聯方式,還可以借助於高能輻射來進行本發明共聚物的交聯,例如貝塔射線或伽馬射線,其中在此情況下還可以使用上述的助劑來改良交聯產率。
視情況,此類可硫化的混合物也可以另外包含一種或多種對於橡膠技術人員而言常規的添加劑和纖維材料。這包括例如填料,可塑劑,抗老化劑,光保護劑,加工助劑,增黏劑,推進劑,染料,顏料,蠟,樹脂,有機酸和/或其鹽,硫化延遲劑,金屬氧化物,纖維,以及填料活化劑或其他添加劑,該等添加劑在橡膠行業中是已知的(見例如烏爾曼化工百科全書(Ullmann’s Encyclopedia of Industrial Chemistry),VCH Verlagsgesellschaft mbH,D-69451魏茵海姆,1993,卷A 23“化學品和添加劑(Chemicals and Additives)”第366-417頁或者Bayer AG“橡膠工業手冊(Manual for the Rubber Industry)”第2完全修訂版,勒沃庫森,1993)。
本發明之可硫化的組成物還可以較佳的是包含另外一種或多種填料,例如像炭黑、滑石、矽石、碳酸鈣和(鈣化的)高嶺土、(鈣化的)矽酸鋁,特別較佳的是炭黑、矽石、鈣化的矽酸鋁、和/或鈣化的高嶺土。
本發明的可硫化的組成物還可以另外包含一種或多種可塑劑,例如像癸二酸二辛酯,己二酸二辛酯,磷酸酯,TOTM等等。
作為填料活化劑考慮例如有機矽烷,如乙烯基三甲氧基矽烷、乙烯基二甲氧基甲基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基-
乙氧基)矽烷、N-環己基-3-胺基丙基三甲氧基矽烷、3-胺基丙基-三甲氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、三甲基乙氧基矽烷、異辛基三甲氧基矽烷、異辛基三乙氧基矽烷、十六烷基三甲氧基矽烷、(十八烷基)甲基-二甲氧基矽烷和含環氧基的矽烷,例如像3-環氧丙氧基丙基三甲氧基矽烷或3-環氧丙氧基丙基三乙氧基矽烷。其他的填料活化劑為例如介面活性的物質,如三乙醇胺、三甲氧基丙烷、己三醇和具有74至10 000g/mol的分子量的聚乙二醇。填料改性劑的量通常為0至10重量份數,相對于本發明之共聚物的100重量份數。
作為抗氧化劑可以添加熟習該項技術者已知的所有可硫化的組成物,該等組成物通常以0至5重量份數、較佳的是0.5至3重量份數的量使用,相對于本發明共聚物的100重量份數。較佳的是使用CDPA和TMQ。
作為加工助劑和/或脫模劑考慮例如飽和的或部分不飽和的脂肪酸和油酸及其衍生物(脂肪酸酯、脂肪酸鹽、脂肪醇、脂肪酸醯胺)。此外可以按比加工助劑更小的投料量使用臭氧保護蠟(商品名稱例如Antilux®)。這種試劑較佳的是以相對於100重量份的本發明共聚物,0到10重量份、較佳的是0到2重量份、較佳的是0到1重量份的量使用。為了進一步改良可脫模性,還可以使用塗覆在模具表面上的產品,例如像基於低分子的矽化合物的產品、基於氟聚合物的產品以及基於苯酚樹脂的產品。
作為用於製造發泡的產品之推進劑可以使用例如OBSH或ADC。
還可行的是,根據US-A-4,826,721的傳授內容用由玻璃製成的增強載體(纖維)來增強,以及藉由由脂肪族和芳香族的聚醯胺(Nylon®,Aramid®)、聚酯和天然纖維產品製成的線、織物、纖維來增強。
本發明之可硫化組成物較佳的是以如下方式製造,本發明之
共聚物與交聯劑、選擇性地一種或多種助劑以及選擇性地其他的化學品和添加材料(在橡膠行業中通常使用的)例如像上文所述借助於通常的混合機組(例如輥磨機或內部混合機)進行混合。在此可以應用單步或多步的混合方法。
下面示例性地展示可如何實施本發明的兩個變體:
方法A:在內部混合機中製造
在開始時間點,用本發明之共聚物填充內部混合機(較佳的是具有所謂的“彼此內部接合”的轉子幾何結構的內部混合機),並且造成材料的粉碎。在適合的混合時間段之後,添加填料和添加劑。混合在用如下措施控制溫度的情況下進行:混合物料在80至150℃範圍內的溫度下保持適合的時間。在另一個適合的混合時間段之後,進行其他的混合物成分的添加,如視情況硬脂酸、助劑、抗氧化劑、可塑劑、白色顏料(例如二氧化鈦)、顏料和其他的加工作用材料。在另一個適合的混合時間段之後,將該內部混合機通氣並且清潔管道。在另一個適合的時間段之後,添加交聯劑。在此,要小心地控制混合溫度以便避免混合機中的硫化。選擇性地,必須減小轉子的轉速以降低混合物溫度。在另一個適合的時間段之後,將該內部混合機清空,同時獲得可硫化的混合物。適合的時間段應理解為幾秒至幾分鐘。如此製造的可硫化混合物可以按通常方式,如藉由孟納黏度、藉由孟納焦燒值或藉由流變計測試來評估。替代地,該混合物可以在沒有添加交聯劑的情況下倒出並且將交聯劑在一輥磨機上混入。
方法B:在輥上製造
在投料方面的順序可以以類似於上述方法A的方式進行。
本發明之共聚物或包含該共聚物的可硫化組成物的硫化典型地在100至250℃、較佳的是140至220℃、特別較佳的是160至200℃範圍
內的溫度下進行。在需要時,可以在硫化之後在約150至200℃的溫度下在1至24小時期間進行退火,以便改良最終產物性質。
本發明的主題還有藉由所述硫化可獲得的硫化物。因此,這應理解為硫化的本發明的共聚物、以及包含本發明共聚物和較佳的是一個或多個交聯劑的硫化組成物。此類硫化物顯示了在室溫和150℃下的壓力變形測試中非常好的值、高拉伸張力和良好的斷裂伸長率,以及非常好的低油溶脹性和低玻璃轉化溫度的組合。
本發明之共聚物或由其製造的可硫化的混合物和/或硫化物可以用於製造未發泡的或發泡的成形物件,以及用於製造所有類型的薄膜和塗層,尤其用於製造纜線導電層、纜線外套、密封件、傳送帶、氣囊、軟管、氣缸蓋密封件和O形環。本發明因此還包括上述的包含本發明硫化物之成形物件。本發明的硫化物還可以混合到塑膠中,在那裡它們用作不揮發的抗靜電劑。因此,本發明之共聚物用於聚合物的抗靜電裝備或含本發明硫化物-的帶抗靜電裝備的塑膠的用途也係本發明的另一個主題。
此外,本發明之共聚物可以用作熱塑性硫化物中的彈性體相,以及用作塑膠或橡膠(較佳的是PVC、聚醯胺、聚酯和/或HNBR)中的摻合成分。
其他的應用可能性在於本發明之共聚物用作塑膠(PVC、聚醯胺和/或聚酯)中的不揮發的可塑劑和/或抗衝擊改性劑之用途。
因此,含本發明硫化物作為彈性體相的熱塑性硫化物,以及含本發明硫化物的塑膠和橡膠,尤其作為不揮發性可塑劑和含本發明硫化物作為抗衝擊改性劑的塑膠係本發明的額外的主題。
本發明的一個實質性的優點在於,本發明的硫化物第一次具有低玻璃轉化溫度和良好的耐油性的良好組合。
測量方法:
玻璃轉化溫度(Tg)的確定借助於動態示差掃描量熱法(英語:Differential Scanning Calorimetry-DSC)根據EN ISO 1135701:2009和EN ISO 11357-2:2014進行,作為惰性氣體使用氦氣,玻璃轉化溫度根據拐點方法來確定。溫度採樣速率為在共聚物的情況下20K/min,硫化物的情況下10K/min。
共聚物的組成的確定借助於1H NMR(設備:Bruker DPX400帶有軟體XWIN-NMR 3.1,測量頻率400MHz)。
根據DIN 55672-1執行凝膠滲透色譜法(GPC),凝膠滲透色譜(GPC)部分1:四氫呋喃(THF)作為洗脫劑,添加0.5重量%的三乙基胺。聚苯乙烯用作標準。
孟納黏度值(ML(1+4)100℃)的確定相應地借助於剪切盤黏度計根據ISO 289在100℃下進行。
用於確定機械性質的板在Werner & Pfleiderer公司的硫化壓機中在特氟龍薄膜之間在所給出條件下硫化。
肖氏A硬度根據ASTM-D2240-81測量。
用於確定張力與變形的依賴性的拉伸實驗根據DIN 53504或ASTM D412-80來執行。
熱氣體老化根據DIN 53508/2000進行。採用了方法4.1.1“在帶有強制通風的熱箱中儲存”。
油儲存和水儲存根據DIN ISO 1817進行。
用商品名標記的物質:
VAMAC GLS DuPont公司的AEM:62.7重量%的甲基丙烯酸酯,33.4重量%的乙烯,3.9重量%的富馬酸單乙酯,TG-25.6℃。
VAMAC DP DuPont公司的AEM:59.0重量%的甲基丙烯酸酯,41.0重量%的乙烯,TG-29℃。
SR550 甲基丙烯酸甲氧基聚乙二醇酯(PEG單元的Mw 350g/mol),Sartomer Europe公司
SR552 甲基丙烯酸甲氧基聚乙二醇酯(PEG單元的Mw約553g/mol),Sartomer Europe公司
Antilux 110公司 Rheinchemie Rheinau公司的石蠟
Rhenofit TAC/S Rheinchemie Rheinau GmbH公司的在30%矽酸上的70%氰酸三烯丙基酯
Rhenofit DDA Rheinchemie Rheinau GmbH公司的抗老化劑(二苯基胺衍生物)
Perkadox 14-40 B-PD AkzoNobel N.V.公司的負載型二-(三級丁基過氧化異丙基)苯
Corax® N550/30 Orion Engineered Carbons GmbH公司的炭黑
共聚物的製造:
M1
聚合物的製造在5L的攪拌高壓釜中進行。在該5L反應器中30℃下相繼地向其中引入1492g的溶液,該溶液由1490.0g三級丁醇和2.0g丙烯酸甲酯以及252.5g的活化劑溶液組成,該活化劑溶液由2.5g AIBN(偶
氮-雙-(異丁腈))和250.0g三級丁醇溶液組成。反應器用氮氣載入並且然後壓入960.0g乙烯。溫度提高到70℃,其中設定約380bar的壓力。隨後以約0.46g/min的速度在9h內向反應混合物中投料一種溶液,該溶液由200.0g丙烯酸甲酯和50.0g SR550組成。在整個聚合過程中,藉由壓入乙烯將壓力保持在380bar±10bar。
在10h的反應時間之後,將乙烯投料停止並且從該5L反應器緩慢地將聚合物溶液壓入截止高壓釜。在去除溶劑和殘餘單體之後,獲得312.0g的SR550-乙烯-丙烯酸甲酯共聚物。
Mn=48880g/mol,Mw=109106g/mol,Mz=183890g/mol
乙烯=36.1重量%,丙烯酸甲酯=48.2重量%,SR550=15.7重量%,ML(1+4)100℃=<10;Tg=-34℃
M2
在裝備有特氟龍攪拌器和強力冷卻器的四頸燒瓶中,在氮氣下將75g水,5.5g十二烷基磺酸鈉,62g丙烯酸乙酯,24g丙烯酸丁酯,12g SR552和2g富馬酸單乙酯加入。然後將0.002g甲醛次硫酸氫鈉和0.005g丁基過氧化氫加入。在開始聚合之後,溫度上升到30℃。在0.5h的聚合時長之後將聚合物用20%的水性NaCl溶液沈澱。隨後將聚合物用水清洗並在75℃下真空中乾燥。獲得了具有如下組成的85g丙烯酸酯橡膠:
丙烯酸乙酯:62重量%,丙烯酸丁酯:24.0重量%,SR552:12重量%,富馬酸單乙酯:2.0重量%
Tg=-31℃。
可硫化混合物和硫化物的製造
根據在下面表1中展示的配方根據方法B在輥上製造聚合
物。
在壓機中180℃下(對於2mm厚的板/測試體為10min,對於6mm厚的板/測試體為12min)在壓機中進行硫化。在硫化之後,將板或測試體在175℃下退火4h。
如從表2可以看出的,由本發明的聚合物製造的硫化物具有可比較的油溶脹性和明顯降低的玻璃轉化溫度。
本發明的實例M1顯示出在另外與乙烯含量相對應的物理性質(如斷裂伸長率、油溶脹性等等)下相對於VM1和VM2明顯更低的玻璃轉化溫度。在實施例M1中出人意料地低的孟納黏度甚至可能允許提高用於硫化的過氧化物量,由此可能進一步減少油溶脹性而不產生玻璃轉化溫度的提高。
Claims (16)
- 一種共聚物之用途,該共聚物包含i)49至99重量%、較佳的是55至90重量%的衍生自至少一種丙烯酸烷基酯的重複單元,該重複單元與重複單元ii)不同,ii)1至51重量%的衍生自至少一種具有通式(I)之單體的重複單元CH2=C(R1)(COO(R2O)nR3) (I)其中R1 代表氫或甲基,R2 分別彼此獨立地代表直鏈或分支的C2至C6-烯基,R3 代表氫,未取代或用C1-C3烷基取代的苯基,直鏈或分支的C1-C8烷基或-C(=O)R4,R4 代表氫或直鏈或分支的C1-C8烷基,並且n 代表2至30的數字,以及iii)0至50重量%、較佳的是0至45重量%的衍生自乙烯的重複單元,其中該等量分別相對於重複單元i)至iii)的總量,其係用於製造硫化物和可硫化組成物。
- 如申請專利範圍第1項所述共聚物之用途,其中該丙烯酸烷基酯具有1至10個碳原子的烷基部分,並且較佳的是選自丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸異丙酯、丙烯酸正丁酯、丙烯酸正己酯、丙烯酸3-丙基庚酯、丙烯酸2-乙基己酯、丙烯酸正辛酯,以及該等丙烯酸酯的混合物,特別較佳的是丙烯酸甲酯、丙烯酸乙酯和丙烯酸正丁酯以及該等丙烯酸酯的混合物。
- 如申請專利範圍第1或2項所述共聚物之用途,其中該共聚物包含,相對 於重複單元i)至iii)的總和,2至40重量%、較佳的是4至25重量%、且特別較佳的是6至20重量%的通式(I)之單體。
- 如申請專利範圍第1至3項中任一項所述共聚物之用途,其中R2部分係分別彼此獨立地選自由乙烷-1,2-二基,丙烷-1,3-二基,丙烷-1,2-二基,丁烷-1,4-二基,丁烷-1,3-二基,戊烷-1,3-二基,戊烷-1,4-二基,戊烷-1,5-二基和2-甲基丁烷-1,4-二基所組成之群組,較佳的是選自乙烷-1,2-二基,丙烷-1,3-二基,丙烷-1,2-二基及丁烷-1,4-二基,特別較佳的是選自乙烷-1,2-二基及丙烷-1,2-二基。
- 如申請專利範圍第1至4項中任一項所述共聚物之用途,其中R3部分係選自由H、CH3、CH2CH3、CH2CH2CH3、CH2CH2CH2CH3、CHO、COCH3、COCH2CH3、COCH2CH2CH3和COCH2CH2CH2CH3所組成之群組,較佳的是選自H、CH3、CH2CH3和COCH3,且特別較佳的是選自CH3、CH2CH3和COCH3。
- 如申請專利範圍第1至5項中任一項所述共聚物之用途,其中該共聚物還具有一種或多種額外的共聚單體(iv),以少於25重量%、較佳的是少於20重量%、還較佳的是少於15重量%、仍進一步較佳的是少於10重量%、特別較佳的是少於5重量%且非常特別較佳的是少於1重量%的總量,分別基於重複單元i)至iii)和該一種或多種額外的共聚單體的總量。
- 如申請專利範圍第6項所述共聚物之用途,其中該等額外的共聚單體(iv)選自含環氧基的丙烯酸酯,含環氧基的甲基丙烯酸酯,具有2至8個碳原子的烷氧基烷基的丙烯酸烷氧基烷基酯,乙烯基酮,乙烯基芳香族化合物,共軛二烯,α-單烯烴,具有羥基的乙烯基單體,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,丙烯酸,甲基丙烯酸,偏氟乙烯,六氟丙烯,偏氯乙烯,四氟乙烯,四氯乙烯,氯乙烯,不飽和醯胺 單體,一氧化碳以及該等單體的混合物,較佳的是選自丙烯酸甲酯,丙烯酸乙酯,丙烯酸丙酯,丙烯酸正丁酯,丙烯酸2-乙基己酯,丙烯酸正辛酯,甲基丙烯酸縮水甘油酯,己二酸二乙烯酯,甲基乙烯基酮,乙基乙烯基酮,苯乙烯,α-甲基苯乙烯,乙烯基甲苯,丁二烯,異戊二烯,丙烯,1-丁烯,丙烯酸β-羥乙基酯,丙烯酸4-羥丁基酯,丙烯酸3-氰基乙基酯,丙烯醯胺,N-甲基甲基丙烯醯胺,丙烯酸2-甲氧基乙基酯,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,一氧化碳以及該等單體的混合物,並且特別較佳的是選自丙烯酸,甲基丙烯酸,丙烯酸2-甲氧基乙基酯,甲基丙烯酸縮水甘油酯,乙酸氯乙烯酯,馬來酸單烷基酯,富馬酸單烷基酯,一氧化碳以及該等單體的混合物。
- 如申請專利範圍第1至7項中任一項所述共聚物之用途,其中該共聚物包含衍生自乙烯、丙烯酸甲酯和具有2至20個乙二醇和/或丙二醇重複單元的含聚伸烷基二醇的(甲基)丙烯酸酯的重複單元,較佳的是與衍生自丙烯酸丁酯、馬來酸單烷基酯和/或富馬酸單烷基酯的重複單元一起。
- 如申請專利範圍第1至7項中任一項所述共聚物之用途,其中該共聚物包含衍生自兩種或多種丙烯酸烷基酯、較佳的是丙烯酸乙酯和丙烯酸丁酯、以及具有2至20個乙二醇和/或丙二醇重複單元的含聚伸烷基二醇的(甲基)丙烯酸酯的重複單元。
- 一種用於製造可硫化組成物之方法,其係藉由混合如申請專利範圍第1至9項中任一項所述之共聚物與一種或多種交聯劑。
- 一種可硫化組成物,其包含如申請專利範圍第1至9項中任一項所述之共聚物、一種或多種交聯劑、以及選擇性地用於提高交聯產率的助劑。
- 一種用於製造硫化物之方法,其係藉由交聯如申請專利範圍第11項所述之可硫化組成物。
- 一種從如申請專利範圍第1至9項中任一項所述之共聚物、如申請專利範圍第11項所述之可硫化組成物和/或藉由如申請專利範圍第12項所述之方法獲得的硫化物。
- 一種如申請專利範圍第1至9項中任一項所述共聚物之用途,其係用於製造起泡或不起泡的成形物件,該成形物件較佳的是纜線導電層、纜線外套、密封件、傳送帶、氣囊、軟管、氣缸蓋密封件和O形環。
- 如申請專利範圍第1至9項中任一項所述共聚物之用途,其係作為在塑膠、較佳的是PVC、聚醯胺和/或聚酯中的不揮發性可塑劑和/或抗衝擊改性劑。
- 如申請專利範圍第1至9項中任一項所述共聚物之用途,其係作為在塑膠或橡膠、較佳的是PVC、聚醯胺、聚酯和/或HNBR中的摻合成分。
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EP (1) | EP3288987B2 (zh) |
JP (1) | JP6767390B2 (zh) |
KR (1) | KR102609762B1 (zh) |
CN (1) | CN107580614B (zh) |
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SG11201906829SA (en) * | 2017-01-31 | 2019-08-27 | Zeon Corp | Acrylic rubber, acrylic rubber composition, and crosslinked acrylic rubber |
JP6958436B2 (ja) * | 2018-03-06 | 2021-11-02 | 日本ゼオン株式会社 | アクリルゴム、アクリルゴム組成物、アクリルゴム架橋物及びホース |
KR20210151598A (ko) | 2020-06-05 | 2021-12-14 | 코웨이 주식회사 | 착탈식 커버가 구비된 매트리스 |
JP7007440B2 (ja) * | 2020-09-24 | 2022-01-24 | 藤森工業株式会社 | 帯電防止表面保護フィルム |
EP4019586A3 (en) | 2020-12-21 | 2022-09-28 | Parker Hannifin Corp. | High temperature, oil-resistant thermoplastic vulcanizates |
CN115043978B (zh) * | 2021-03-09 | 2023-10-20 | 北京化工大学 | 一种富马酸酯生物基耐油弹性体及其制备方法和复合材料 |
US20220306855A1 (en) | 2021-03-25 | 2022-09-29 | Parker-Hannifin Corporation | Thermoplastic vulcanizates comprising acrylate rubber and thermoplastic polyurethane |
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US2599123A (en) | 1950-08-18 | 1952-06-03 | Du Pont | Copolymers of ethylene with an alkyl acrylate and an alkyl monoester of a butene-1,4-dioic acid |
US3883472A (en) | 1973-08-09 | 1975-05-13 | Du Pont | Fast curing heat stable elastomeric compositions |
US4026851A (en) | 1975-08-13 | 1977-05-31 | E. I. Du Pont De Nemours And Company | Acrylate polymers cured with diamines in the presence of an acid catalyst |
JPS52126495A (en) * | 1976-04-16 | 1977-10-24 | Sumitomo Chem Co Ltd | Novel ethylene copolymer and preparation thereof |
WO1980002289A1 (en) * | 1979-04-24 | 1980-10-30 | V Pavlyuchenko | Copolymers of vinylacetate,ethylene and peroxy-containing alkylacrylate |
DE3618907A1 (de) | 1986-06-05 | 1987-12-10 | Bayer Ag | Verbundwerkstoffe aus vorbehandeltem fasermaterial und vulkanisaten aus hnbr |
EP0538640B1 (en) * | 1991-09-30 | 1996-09-04 | Nippon Zeon Co., Ltd. | Acrylic copolymer elastomer and vulcanizable composition containing same |
US5777029A (en) | 1996-07-26 | 1998-07-07 | Advanced Elastomer Systems, L.P. | Co-cured rubber-thermoplastic elastomer compositions |
JPH1192614A (ja) | 1997-09-19 | 1999-04-06 | Nippon Mektron Ltd | アクリルエラストマー組成物 |
EP0922730B1 (en) * | 1997-12-10 | 2003-05-28 | Advanced Elastomer Systems, L.P. | Thermoplastic vulcanizates made from condensation polymer and crosslinked elastomer |
DE19942301A1 (de) | 1999-09-04 | 2001-03-08 | Basf Ag | Zementzusammensetzungen, enthaltend redispergierbare Polymerisatpulver |
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JP2007186631A (ja) * | 2006-01-16 | 2007-07-26 | Yunimatekku Kk | アクリルゴム組成物 |
JP2007194102A (ja) * | 2006-01-20 | 2007-08-02 | Toyo Ink Mfg Co Ltd | 色素増感型光電変換素子用電解質組成物および該電解質組成物を用いた光電変換素子 |
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EP3288987B2 (de) | 2022-12-28 |
US20180118866A1 (en) | 2018-05-03 |
CA2984353A1 (en) | 2016-11-03 |
WO2016174203A1 (de) | 2016-11-03 |
JP2018518557A (ja) | 2018-07-12 |
JP6767390B2 (ja) | 2020-10-14 |
CN107580614B (zh) | 2021-05-14 |
CN107580614A (zh) | 2018-01-12 |
KR102609762B1 (ko) | 2023-12-06 |
EP3288987A1 (de) | 2018-03-07 |
KR20180002624A (ko) | 2018-01-08 |
TWI689548B (zh) | 2020-04-01 |
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