CN115304757B - 一种嵌段型油墨树脂及其制备方法 - Google Patents
一种嵌段型油墨树脂及其制备方法 Download PDFInfo
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- CN115304757B CN115304757B CN202210853019.5A CN202210853019A CN115304757B CN 115304757 B CN115304757 B CN 115304757B CN 202210853019 A CN202210853019 A CN 202210853019A CN 115304757 B CN115304757 B CN 115304757B
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- acrylate
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- acid
- butyl
- ink resin
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- 239000011347 resin Substances 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title abstract description 11
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- 239000002253 acid Substances 0.000 claims abstract description 24
- 238000005886 esterification reaction Methods 0.000 claims abstract description 17
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 14
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 46
- 238000010438 heat treatment Methods 0.000 claims description 30
- -1 acrylic ester Chemical class 0.000 claims description 27
- 238000001816 cooling Methods 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
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- 238000007599 discharging Methods 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003054 catalyst Substances 0.000 claims description 6
- 239000012986 chain transfer agent Substances 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 claims description 4
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
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- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
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- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 claims description 4
- XHGOVHOCQHSNTI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy formate Chemical compound CC(C)(C)OOC=O XHGOVHOCQHSNTI-UHFFFAOYSA-N 0.000 claims description 3
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 claims description 3
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 claims description 3
- NJJVQRWBOBTTSN-UHFFFAOYSA-N 2-ethenyl-1,3-dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1C=C NJJVQRWBOBTTSN-UHFFFAOYSA-N 0.000 claims description 3
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
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- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 claims description 3
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 claims description 3
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Abstract
本发明公开了一种嵌段型油墨树脂及其制备方法。该嵌段型油墨树脂是通过二元酸(酐)、二元醇、端羟基聚丙烯酸酯、改性松香树脂等酯化反应而得到的。由于在油墨树脂中引入了聚酯、聚丙烯酸酯和改性松香树脂结构,使得该嵌段型油墨树脂对各类塑料薄膜基材具有广泛的适用性。
Description
技术领域
本发明涉及高分子化学领域,特别涉及一种嵌段型油墨树脂。
背景技术
近年来,人民生活水平的提高带动了包装工业的快速增长,由于凹版印刷在国内塑料薄膜印刷中占有重要地位,因此也促进了凹版印刷用复合油墨技术及市场的不断发展。目前塑料凹版印刷用油墨树脂主要有聚氨酯体系、氯醋体系、聚酰胺体系、聚乙烯缩丁醛体系、硝化棉体系等,但是单一树脂往往难以满足印刷油墨多方面的要求,因此对现有油墨树脂的改性一直是油墨树脂发展的重要方面。
以聚丙烯酸酯为油墨连接料制备的复合油墨,主要适合BOPP薄膜基材的印刷,因此,为了扩展该类油墨树脂的适用范围,众多企业和科研院所积极展开了相关方面的研究工作。专利CN102653595A公布了一种聚酯改性羟基聚丙烯酸酯的制备方法及含有聚酯改性羟基聚丙烯酸酯的涂料。该方法将羟基聚酯与含酸酐的羟基聚丙烯酸酯通过酯化反应制得该树脂。专利CN101029122A公布了一种丙烯酸酯改性聚酯树脂的制备方法及其用途。该方法首先制得带羧基的丙烯酸酯预聚体,然后将预聚体与二元酸、二元醇酯化制得该树脂。
发明内容
本发明的目的在于提供一种嵌段型油墨树脂。
本发明提供的技术方案为:
首先制得端羟基聚丙烯酸酯,然后与二元酸(酐)、二元醇、改性松香树脂等酯化合成嵌段型油墨树脂。
一种嵌段型油墨树脂,该嵌段型油墨树脂由以下步骤制得:
(1)将溶剂加入反应釜,升温至75~90℃,将(甲基)丙烯酸酯、苯乙烯类单体、活性功能单体、引发剂、链转移剂组成的混合液在2~5小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应5~8小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将二元酸(酐)、二元醇、催化剂加入反应釜中,通入氮气,升温至140~150℃,待原料全部熔化后开始搅拌反应,在2~5小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为10~30mgKOH/g时,降温至120~130℃之间,向反应釜中加入端羟基聚丙烯酸酯、改性松香树脂,在1~2小时内升温至220℃,保温酯化至酸值低于3mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
进一步的,步骤(1)中,以重量百分比计,各组分的含量如下:
溶剂 30~70 wt%
(甲基)丙烯酸酯 10~35 wt%
苯乙烯类单体 15~30 wt%
活性功能单体 1~15 wt%;
所述引发剂用量为苯乙烯类单体和活性功能单体总重量的0.5~10wt%,所述链转移剂用量为引发剂重量的10~50wt%。
进一步的,步骤(1)中所述溶剂为乙酸乙酯、乙酸丁酯、环己酮、甲乙酮、甲戊酮中任一种或多种。
进一步的,步骤(1)中所述(甲基)丙烯酸酯为(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸-2-乙基己酯、丙烯酸壬酯、丙烯酸癸酯、丙烯酸十二烷基酯、(甲基)丙烯酸十六酯、(甲基)丙烯酸十八酯、丙烯酸苯基酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸三甲基环己酯、(甲基)丙烯酸叔丁基环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸甲氧基乙酯、丙烯酸乙氧基甲酯、丙烯酸丙氧基乙酯、丙烯酸丁氧基乙酯、丙烯酸乙氧基丙酯、2-(2-甲氧乙氧)乙基丙烯酸酯、2-(2-乙氧乙氧)乙基丙烯酸酯、2-苯氧乙基丙烯酸酯中任一种或多种。
进一步的,步骤(1)中所述苯乙烯类单体为苯乙烯、α-甲基苯乙烯、对甲基苯乙烯、4-乙酰氧基苯乙烯、3,4-二甲基苯乙烯、2,4,6-三甲基苯乙烯、对乙基苯乙烯、2,5-二乙基苯乙烯、对丁基苯乙烯、间叔丁基苯乙烯、对苄基苯乙烯、邻甲氧基苯乙烯、对甲氧基苯乙烯、2,6-二甲氧基苯乙烯、2-甲氧基-5-异丙基苯乙烯中任一种或多种。
进一步的,步骤(1)中所述活性功能单体为(甲基)丙烯腈、N-甲氧基乙基甲基丙烯酰胺、N-丁氧基甲基甲基丙烯酰胺、(甲基)丙烯酸二甲基氨基甲酯、(甲基)丙烯酸二乙基氨基甲酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸二乙基氨基乙酯、甲基丙烯酸二丙基氨基乙酯、甲基丙烯酸二丁基氨基乙酯、(甲基)丙烯酸二甲基氨基丙酯、(甲基)丙烯酸二乙基氨基丙酯中任一种或多种。
进一步的,步骤(1)中所述引发剂为偶氮二异丁腈、偶氮二异庚腈、2,2’-偶氮双(2,4-二甲基戊腈)、2,2’-偶氮二异丁酸二甲酯、4, 4’-偶氮双(4-氰基戊酸)、2,2’-偶氮双(4-甲氧-2,4-二甲基戊腈)、2,2’-偶氮双(2-甲基丙酸)二甲酯、过氧化二苯甲酰、过氧化苯甲酸叔丁酯、过氧化二碳酸二异丙酯、过氧化(2-乙基己酸)叔丁酯、过氧化甲酸叔丁酯、叔丁基过氧化氢、叔戊基过氧化氢、异丙基苯过氧化氢、过氧化二碳酸二正丙酯、过氧化二碳酸二(2-乙氧基)乙酯、过氧化新癸酸叔丁酯、过氧化特戊酸叔丁酯、过氧化双(3,5,5-三甲基己酰)、过氧化二乙酰中任一种或多种。
进一步的,步骤(1)中所述链转移剂为β-巯基乙醇、3-巯基丙醇、3-巯基-2-丁醇、3-巯基-2-戊醇、3-巯基-2-甲基戊醇、6-巯基己醇中任一种或多种。
进一步的,所述步骤(2)中,以重量百分比计,各组分含量如下:
二元酸(酐) 15~35 wt%
二元醇 10~30 wt%
端羟基聚丙烯酸酯 10~35 wt%
改性松香树脂 5~30 wt%;
所述催化剂用量为反应物总重量的0.01~0.5wt%。
进一步的,步骤(2)中所述二元酸(酐)为乙二酸、丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、对苯二甲酸、邻苯二甲酸(酐)、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、间苯二甲酸、马来酸(酐)、富马酸、3, 3-二甲基戊二酸中任一种或多种。
进一步的,步骤(2)中所述二元醇为乙二醇、1,2-丙二醇、1,3-丙二醇、一缩二乙二醇、一缩二丙二醇,1,4-丁二醇、1,6-己二醇、1,8-辛二醇、1,10-癸二醇、1,12-十二烷二醇、甲基丙二醇、新戊二醇、2-乙基-2-丁基-1、3-丙二醇、1,2-环己烷二甲醇、1,4-环己烷二甲醇中任一种或多种。
进一步的,步骤(2)中所述改性松香树脂为二氢松香、四氢松香、丙烯海松酸、马来海松酸、富马海松酸中任一种或多种。
进一步的,步骤(2)中所述的催化剂为二月桂酸二丁基锡、辛酸亚锡、二醋酸二丁基锡、三丁基氧化锡、二辛基氧化锡、三丁基氯化锡、2-乙基己酸铅、苯甲酸铅、环烷酸铅、苯甲酸钴、2-乙基己酸钴、环烷酸锌、辛酸铁中任一种或多种。
本发明的嵌段型油墨树脂由于结合了聚酯、聚丙烯酸酯和改性松香树脂的特点,能有效地适应各类塑料薄膜基材的印刷。
具体实施方式
下面通过实施例对本发明进行具体的描述,该实施例只用于对本发明的进一步说明,不应理解为对本发明保护范围的限定。对本领域技术人员来说,在不背离本发明的范围和总体构思的前提下,按照本发明的方法作出不同的修改和变化,应属本发明的保护范围之内。
实施例1
嵌段型油墨树脂的制备:
(1)将45kg乙酸乙酯加入反应釜中,升温至75℃,将25kg甲基丙烯酸丙酯、19kg苯乙烯、8kgN-丁氧基甲基甲基丙烯酰胺、0.78kg2,2’-偶氮双(2,4-二甲基戊腈)、0.156kg3-巯基-2-丁醇组成的混合液在2小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应5小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将18kg己二酸、5kg1,3-丙二醇、7kg1,10-癸二醇、0.155kg辛酸亚锡加入反应釜中,通入氮气,升温至140℃,待原料全部熔化后开始搅拌反应,在2小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为15mgKOH/g时,降温至120℃,向反应釜中加入20kg端羟基聚丙烯酸酯、12kg四氢松香,在1小时内升温至220℃,保温酯化至酸值为2.9mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
实施例2
嵌段型油墨树脂的制备:
(1)将56kg乙酸丁酯加入反应釜中,升温至80℃,将14kg丙烯酸正丁酯、16kg丙烯酸壬酯、24kg2,5-二乙基苯乙烯、11kg甲基丙烯酸二甲基氨基丙酯、1.56kg过氧化二苯甲酰、0.624kg3-巯基-2-戊醇组成的混合液在3小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应6小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将7kg丁二酸、18kg癸二酸、16kg一缩二丙二醇、6kg1,4-丁二醇、0.115kg二辛基氧化锡加入反应釜中,通入氮气,升温至145℃,待原料全部熔化后开始搅拌反应,在3小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为21mgKOH/g时,降温至125℃,向反应釜中加入20kg端羟基聚丙烯酸酯、15kg丙烯海松酸,在2小时内升温至220℃,保温酯化至酸值为1.8mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
实施例3
嵌段型油墨树脂的制备:
(1)将41kg甲乙酮加入反应釜中,升温至85℃,将10kg甲基丙烯酸甲酯、9kg丙烯酸叔丁酯、22kg邻甲氧基苯乙烯、14kg丙烯酸二乙基氨基丙酯、1.76kg叔戊基过氧化氢、0.493kg6-巯基己醇组成的混合液在4小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应7小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将23kg辛二酸、8kg间苯二甲酸、9kg1,2-丙二醇、18kg1,2-环己烷二甲醇、0.41kg三丁基氧化锡加入反应釜中,通入氮气,升温至143℃,待原料全部熔化后开始搅拌反应,在5小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为14mgKOH/g时,降温至126℃,向反应釜中加入19kg端羟基聚丙烯酸酯、22kg富马海松酸,在1.5小时内升温至220℃,保温酯化至酸值为2.7mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
实施例4
嵌段型油墨树脂的制备:
(1)将62kg环己酮加入反应釜中,升温至90℃,将5kg甲基丙烯酸乙酯、12kg丙烯酸十二烷基酯、17kg2,4,6-三甲基苯乙烯、6kg甲基丙烯酸二甲基氨基乙酯、3kg过氧化二碳酸二正丙酯、0.54kg3-巯基丙醇组成的混合液在5小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应8小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将14kg壬二酸、9kg3, 3-二甲基戊二酸、9kg一缩二乙二醇、15kg甲基丙二醇、0.374kg苯甲酸钴加入反应釜中,通入氮气,升温至150℃,待原料全部熔化后开始搅拌反应,在3.5小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为24mgKOH/g时,降温至128℃,向反应釜中加入15kg端羟基聚丙烯酸酯、25kg马来海松酸,在2小时内升温至220℃,保温酯化至酸值为1.1mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
实施例5
嵌段型油墨树脂的制备:
(1)将58kg甲戊酮加入反应釜中,升温至90℃,将12kg甲基丙烯酸甲酯、14kg丙烯酸苄酯、26kg2,6-二甲氧基苯乙烯、6kg甲基丙烯酸二乙基氨基乙酯、1.972kg过氧化甲酸叔丁酯、0.513kgβ-巯基乙醇组成的混合液在5小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应7小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将10kg戊二酸、17kg富马酸、8kg乙二醇、11kg1,8-辛二醇、0.072kg环烷酸铅加入反应釜中,通入氮气,升温至142℃,待原料全部熔化后开始搅拌反应,在4小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为27mgKOH/g时,降温至126℃,向反应釜中加入25kg端羟基聚丙烯酸酯、9kg丙烯海松酸,在1小时内升温至220℃,保温酯化至酸值为2.1mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂。
实施例6
油墨的制备:
用实施例1、2、3、4和5所制嵌段型油墨树脂分别来制备凹版印刷用复合油墨,工艺如下:将33kg所制嵌段型油墨树脂、1.6kg聚酮树脂、30kg乙酸乙酯、6kg乙酸丁酯、29kg钛白粉、2kgBYK-191分散剂、1kg聚乙烯蜡和1.5kg气相二氧化硅放入容器内,用高速分散机搅拌30分钟后,将物料取出,送入砂磨机中进行砂磨,待细度低于10微米时出料,过滤,制得用于凹版印刷用复合油墨。所制凹版印刷用复合油墨的各项检测指标如表1所示。
表1 所制油墨的各项检测指标
。
以上检测结果依据QB/T2024-2012标准检测。
对比例1
(1)将13kg戊二酸、10kg癸二酸、9kg乙二醇、15kg新戊二醇、0.12kg三丁基氯化锡加入反应釜中,通入氮气,升温至150℃,待原料全部熔化后开始搅拌反应,在3.5小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为2mgKOH/g时,降温出料制得油墨树脂。
(2)取33kg上述所制油墨树脂、1.6kg聚酮树脂、30kg乙酸乙酯、6kg乙酸丁酯、29kg钛白粉、2kgBYK-191分散剂、1kg聚乙烯蜡和1.5kg气相二氧化硅放入容器内,用高速分散机搅拌30分钟后,将物料取出,送入砂磨机中进行砂磨,待细度低于10微米时出料,过滤,制得用于凹版印刷用复合油墨。所制凹版印刷用复合油墨的各项检测指标如表2所示。
表2
。
以上检测结果依据QB/T2024-2012标准检测。
最后应说明的是:以上各实施例仅用以说明本发明的技术方案,而非对其限制;尽管参照前述各实施例对本发明进行了详细的说明,但本领域的普通技术人员应当理解:其依然可以对前述各实施例所记载的技术方案进行修改,或者对其中部分或者全部技术特征进行等同替换;而这些修改或者替换,并不使相应技术方案的本质脱离本发明各实施例技术方案的范围。
Claims (8)
1.一种嵌段型油墨树脂,其特征在于,该嵌段型油墨树脂由以下步骤制得:
(1)将溶剂加入反应釜,升温至75~90℃,将(甲基)丙烯酸酯、苯乙烯类单体、活性功能单体、引发剂、链转移剂组成的混合液在2~5小时内匀速滴加到反应釜中,滴加完成后在该温度下继续搅拌反应5~8小时,降至室温,出料制得端羟基聚丙烯酸酯;
(2)将二元酸和/或二元酸酐、二元醇、催化剂加入反应釜中,通入氮气,升温至140~150℃,待原料全部熔化后开始搅拌反应,在2~5小时内升温至180℃,然后以10℃/小时的速度将温度升至220℃,控制分馏柱顶部温度在100±1℃,保温酯化反应至酸值为10~30mgKOH/g时,降温至120~130℃之间,向反应釜中加入端羟基聚丙烯酸酯、改性松香树脂,在1~2小时内升温至220℃,保温酯化至酸值低于3mgKOH/g时,停止反应,降至室温,出料制得嵌段型油墨树脂;
步骤(1)中,以重量百分比计,各组分的含量如下:
溶剂 30~70 wt%
(甲基)丙烯酸酯 10~35 wt%
苯乙烯类单体 15~30 wt%
活性功能单体 1~15 wt%;
所述引发剂用量为苯乙烯类单体和活性功能单体总重量的0.5~10wt%,所述链转移剂用量为引发剂重量的10~50wt%;
所述活性功能单体为(甲基)丙烯腈、N-甲氧基乙基甲基丙烯酰胺、N-丁氧基甲基甲基丙烯酰胺、(甲基)丙烯酸二甲基氨基甲酯、(甲基)丙烯酸二乙基氨基甲酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸二乙基氨基乙酯、甲基丙烯酸二丙基氨基乙酯、甲基丙烯酸二丁基氨基乙酯、(甲基)丙烯酸二甲基氨基丙酯、(甲基)丙烯酸二乙基氨基丙酯中任一种或多种;
步骤(1)中所述链转移剂为β-巯基乙醇、3-巯基丙醇、3-巯基-2-丁醇、3-巯基-2-戊醇、3-巯基-2-甲基戊醇、6-巯基己醇中任一种或多种;
所述步骤(2)中,以重量百分比计,各组分含量如下:
二元酸和/或二元酸酐 15~35 wt%
二元醇 10~30 wt%
端羟基聚丙烯酸酯 10~35 wt%
改性松香树脂 5~30 wt%;
所述催化剂用量为反应物总重量的0.01~0.5wt%;
所述改性松香树脂为二氢松香、四氢松香、丙烯海松酸、马来海松酸、富马海松酸中任一种或多种。
2.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(1)中所述溶剂为乙酸乙酯、乙酸丁酯、环己酮、甲乙酮、甲戊酮中任一种或多种。
3.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(1)中所述(甲基)丙烯酸酯为(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸-2-乙基己酯、丙烯酸壬酯、丙烯酸癸酯、丙烯酸十二烷基酯、(甲基)丙烯酸十六酯、(甲基)丙烯酸十八酯、丙烯酸苯基酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸三甲基环己酯、(甲基)丙烯酸叔丁基环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸甲氧基乙酯、丙烯酸乙氧基甲酯、丙烯酸丙氧基乙酯、丙烯酸丁氧基乙酯、丙烯酸乙氧基丙酯、2-(2-甲氧乙氧)乙基丙烯酸酯、2-(2-乙氧乙氧)乙基丙烯酸酯、2-苯氧乙基丙烯酸酯中任一种或多种。
4.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(1)中所述苯乙烯类单体为苯乙烯、α-甲基苯乙烯、对甲基苯乙烯、4-乙酰氧基苯乙烯、3,4-二甲基苯乙烯、2,4,6-三甲基苯乙烯、对乙基苯乙烯、2,5-二乙基苯乙烯、对丁基苯乙烯、间叔丁基苯乙烯、对苄基苯乙烯、邻甲氧基苯乙烯、对甲氧基苯乙烯、2,6-二甲氧基苯乙烯、2-甲氧基-5-异丙基苯乙烯中任一种或多种。
5.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(1)中所述引发剂为偶氮二异丁腈、偶氮二异庚腈、2,2’-偶氮双(2,4-二甲基戊腈)、2,2’-偶氮二异丁酸二甲酯、4,4’-偶氮双(4-氰基戊酸)、2,2’-偶氮双(4-甲氧-2,4-二甲基戊腈)、2,2’-偶氮双(2-甲基丙酸)二甲酯、过氧化二苯甲酰、过氧化苯甲酸叔丁酯、过氧化二碳酸二异丙酯、过氧化(2-乙基己酸)叔丁酯、过氧化甲酸叔丁酯、叔丁基过氧化氢、叔戊基过氧化氢、异丙基苯过氧化氢、过氧化二碳酸二正丙酯、过氧化二碳酸二(2-乙氧基)乙酯、过氧化新癸酸叔丁酯、过氧化特戊酸叔丁酯、过氧化双(3,5,5-三甲基己酰)、过氧化二乙酰中任一种或多种。
6.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(2)中所述二元酸和/或二元酸酐为乙二酸、丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、对苯二甲酸、邻苯二甲酸和/或邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、间苯二甲酸、马来酸和/或马来酸酐、富马酸、3, 3-二甲基戊二酸中任一种或多种。
7.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(2)中所述二元醇为乙二醇、1,2-丙二醇、1,3-丙二醇、一缩二乙二醇、一缩二丙二醇、1,4-丁二醇、1,6-己二醇、1,8-辛二醇、1,10-癸二醇、1,12-十二烷二醇、甲基丙二醇、新戊二醇、2-乙基-2-丁基-1,3-丙二醇、1,2-环己烷二甲醇、1,4-环己烷二甲醇中任一种或多种。
8.根据权利要求1所述的嵌段型油墨树脂,其特征在于,步骤(2)中所述的催化剂为二月桂酸二丁基锡、辛酸亚锡、二醋酸二丁基锡、三丁基氧化锡、二辛基氧化锡、三丁基氯化锡、2-乙基己酸铅、苯甲酸铅、环烷酸铅、苯甲酸钴、2-乙基己酸钴、环烷酸锌、辛酸铁中任一种或多种。
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Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3561358A (en) * | 1966-10-10 | 1971-02-09 | Xerox Corp | Gravure imaging system |
US5180774A (en) * | 1991-02-19 | 1993-01-19 | Westvaco Corporation | Modified rosin esters and their use in printing inks |
US5264481A (en) * | 1991-11-22 | 1993-11-23 | Westvaco Corporation | Hydroxyacrylic modified inks |
JPH06107999A (ja) * | 1992-08-03 | 1994-04-19 | Westvaco Corp | 水性インク |
US6433052B1 (en) * | 1998-10-14 | 2002-08-13 | Westvaco Corporation | Rosin-fatty acid vinylic polymers as ink additives |
JP2004223893A (ja) * | 2003-01-23 | 2004-08-12 | Dainippon Ink & Chem Inc | 装飾付き繊維強化プラスチック成形品および繊維強化プラスチック成形品の装飾方法 |
CN101029122A (zh) * | 2006-03-03 | 2007-09-05 | 同济大学 | 一种丙烯酸酯改性聚酯树脂的制备方法及其用途 |
WO2009127127A1 (zh) * | 2008-04-18 | 2009-10-22 | 中国科学院化学研究所 | 用于凹版印刷的油墨树脂及其制备方法 |
CN102653595A (zh) * | 2012-04-28 | 2012-09-05 | 英德市波特化工实业有限公司 | 一种聚酯改性羟基聚丙烯酸酯的制备方法及含有聚酯改性羟基聚丙烯酸酯的涂料 |
CN103601876A (zh) * | 2013-11-18 | 2014-02-26 | 广东科茂林产化工股份有限公司 | 一种水性油墨用高分子量改性松香树脂及其制备方法 |
CN103772666A (zh) * | 2012-10-17 | 2014-05-07 | 成都市新津托展油墨有限公司 | 一种聚酯改性聚丙烯酸酯树脂及其制备方法 |
CN104031202A (zh) * | 2014-06-17 | 2014-09-10 | 中国科学院化学研究所 | 聚丙烯酸油墨树脂及其制备方法 |
CN104788665A (zh) * | 2015-04-21 | 2015-07-22 | 中国科学院化学研究所 | 一种醇水溶改性聚酯油墨树脂及其制备方法 |
JP2017149826A (ja) * | 2016-02-24 | 2017-08-31 | 三菱ケミカル株式会社 | 樹脂組成物および印刷インキ |
CN107177020A (zh) * | 2017-04-24 | 2017-09-19 | 东莞市隆海新材料科技有限公司 | 一种马来海松酸改性聚丙烯酸酯分散剂及其制备方法 |
WO2019052951A1 (en) * | 2017-09-12 | 2019-03-21 | Gleitsmann Security Inks Gmbh | INK FOR PRINTING IN HOLES WITH ENERGY CURING |
CN111978784A (zh) * | 2020-09-15 | 2020-11-24 | 中山市富日印刷材料有限公司 | 一种生物质基环保uv光固化油墨的制备方法 |
CN112480823A (zh) * | 2020-12-09 | 2021-03-12 | 山西省应用化学研究所(有限公司) | 胶版油墨用改性松香树脂及其制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7384992B2 (en) * | 2003-11-10 | 2008-06-10 | Meadwestvaco Corporation | Rosin-fatty acid ester vinylic polymers |
-
2022
- 2022-07-20 CN CN202210853019.5A patent/CN115304757B/zh active Active
Patent Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3561358A (en) * | 1966-10-10 | 1971-02-09 | Xerox Corp | Gravure imaging system |
US5180774A (en) * | 1991-02-19 | 1993-01-19 | Westvaco Corporation | Modified rosin esters and their use in printing inks |
US5264481A (en) * | 1991-11-22 | 1993-11-23 | Westvaco Corporation | Hydroxyacrylic modified inks |
JPH06107999A (ja) * | 1992-08-03 | 1994-04-19 | Westvaco Corp | 水性インク |
US6433052B1 (en) * | 1998-10-14 | 2002-08-13 | Westvaco Corporation | Rosin-fatty acid vinylic polymers as ink additives |
JP2004223893A (ja) * | 2003-01-23 | 2004-08-12 | Dainippon Ink & Chem Inc | 装飾付き繊維強化プラスチック成形品および繊維強化プラスチック成形品の装飾方法 |
CN101029122A (zh) * | 2006-03-03 | 2007-09-05 | 同济大学 | 一种丙烯酸酯改性聚酯树脂的制备方法及其用途 |
WO2009127127A1 (zh) * | 2008-04-18 | 2009-10-22 | 中国科学院化学研究所 | 用于凹版印刷的油墨树脂及其制备方法 |
CN102653595A (zh) * | 2012-04-28 | 2012-09-05 | 英德市波特化工实业有限公司 | 一种聚酯改性羟基聚丙烯酸酯的制备方法及含有聚酯改性羟基聚丙烯酸酯的涂料 |
CN103772666A (zh) * | 2012-10-17 | 2014-05-07 | 成都市新津托展油墨有限公司 | 一种聚酯改性聚丙烯酸酯树脂及其制备方法 |
CN103601876A (zh) * | 2013-11-18 | 2014-02-26 | 广东科茂林产化工股份有限公司 | 一种水性油墨用高分子量改性松香树脂及其制备方法 |
CN104031202A (zh) * | 2014-06-17 | 2014-09-10 | 中国科学院化学研究所 | 聚丙烯酸油墨树脂及其制备方法 |
CN104788665A (zh) * | 2015-04-21 | 2015-07-22 | 中国科学院化学研究所 | 一种醇水溶改性聚酯油墨树脂及其制备方法 |
JP2017149826A (ja) * | 2016-02-24 | 2017-08-31 | 三菱ケミカル株式会社 | 樹脂組成物および印刷インキ |
CN107177020A (zh) * | 2017-04-24 | 2017-09-19 | 东莞市隆海新材料科技有限公司 | 一种马来海松酸改性聚丙烯酸酯分散剂及其制备方法 |
WO2019052951A1 (en) * | 2017-09-12 | 2019-03-21 | Gleitsmann Security Inks Gmbh | INK FOR PRINTING IN HOLES WITH ENERGY CURING |
CN111978784A (zh) * | 2020-09-15 | 2020-11-24 | 中山市富日印刷材料有限公司 | 一种生物质基环保uv光固化油墨的制备方法 |
CN112480823A (zh) * | 2020-12-09 | 2021-03-12 | 山西省应用化学研究所(有限公司) | 胶版油墨用改性松香树脂及其制备方法 |
Non-Patent Citations (1)
Title |
---|
水溶性油墨用富马酸改性松香树脂的研制;程珍发,解洪柱,卢渊,钟丽丽,梁经伦;林产化工通讯(02);全文 * |
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