CN104995236A - 木素基涂料组合物 - Google Patents
木素基涂料组合物 Download PDFInfo
- Publication number
- CN104995236A CN104995236A CN201380063787.XA CN201380063787A CN104995236A CN 104995236 A CN104995236 A CN 104995236A CN 201380063787 A CN201380063787 A CN 201380063787A CN 104995236 A CN104995236 A CN 104995236A
- Authority
- CN
- China
- Prior art keywords
- lignin
- coating composition
- solvent
- mixture
- coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920005610 lignin Polymers 0.000 title claims abstract description 74
- 239000008199 coating composition Substances 0.000 title claims abstract description 73
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 239000004593 Epoxy Substances 0.000 claims abstract description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004971 Cross linker Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 22
- -1 (methyl) glycidyl Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 238000004806 packaging method and process Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 2
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims 3
- 238000000034 method Methods 0.000 abstract description 13
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- 230000007935 neutral effect Effects 0.000 abstract description 2
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- 239000000178 monomer Substances 0.000 description 13
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
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- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
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- 229920002488 Hemicellulose Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明包括具有木素的涂料组合物、使用所述涂料组合物涂覆基材的方法，和涂覆有所述涂料组合物的基材。在本发明的一些实施方案中，一种具有如下物质的混合物的组合物：a)木素，b)溶剂，和c)交联剂，其中所述木素具有中性或负电荷。本发明还包括一种具有如下物质的混合物的涂料组合物：a)木素，b)具有(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂和c)溶剂。此外，本发明包括一种具有如下物质的混合物的涂料组合物：a)木素，b)溶剂，和c)酚类交联剂。
Description
发明背景
1.发明领域
本发明涉及包含木素的涂料组合物、用所述涂料组合物涂覆基材的方法和涂覆有所述涂料组合物的基材。
2.相关技术描述
由环氧树脂形成的涂料组合物已用于涂覆食品和饮料的包装和容器。尽管美国、加拿大、欧洲和日本的全球主要食品安全监管局解释的科学证据的衡量显示就目前的商业环氧基涂料而言，消费者所暴露的双酚A水平是安全的，然而一些消费者和品牌持有者持续表达担忧，且期望不含双酚A或者任何其他内分泌干扰剂的涂料。
需要制备不含双酚A或者基本上不含双酚A的涂料组合物。本发明的木素基涂料组合物可用于制备尤其适于作为食品和饮料包装和容器的包装涂料的涂料组合物。
消费者和品牌持有者希望由可再生源制成的涂料组合物，且使用木素作为该涂料组合物中的主要组分为食品接触涂料提供了可持续的原料基础。
发明简述
本发明的涂料组合物提供了良好的固化、耐溶剂性、抗发白性、蒸馏能力以及抗侵蚀性食品和饮料，同时为该涂料组合物中的一些原材料提供可持续的来源。
本发明包括含木素的涂料组合物，使用所述涂料组合物涂覆基材的方法和涂覆有涂料组合物的基材。在本发明的一些实施方案中，所述涂料组合物包含a)木素、b)溶剂和c)交联剂的混合物。本发明还包括涂料组合物，其包含a)木素、b)包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂和c)溶剂的混合物。此外，本发明包括涂料组合物，其包含a)木素、b)溶剂和c)酚类交联剂的混合物。所述混合物中所含的木素可具有中性或负电荷。
所述涂料组合物可通过包括如下步骤的方法制备：将木素、溶剂和交联剂混合。在一些实施方案中，所述涂料组合物可通过包括如下步骤的方法制备：将木素、包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂和溶剂混合。此外，所述涂料组合物可通过包括如下步骤的方法制备：将木素、溶剂和酚类交联剂混合。
还公开了涂覆有本发明涂料组合物的基材。在一些实施方案中，所述基材为用于食品或饮料的罐或包装。
发明详述
在本发明的前述实施方案和其他实施方案以及本文所述的权利要求中所用的下列术语通常具有所示的含义，但是如果本发明的益处通过将下列术语推导至更宽的含义而获得，则这些含义并非意图限制本发明的范围。
本发明包括至少部分涂覆有涂料组合物的基材和涂覆基材的方法。本文所用的术语“基材”包括而不限于用于容纳、碰触或接触任何类型的食品或饮料的罐、金属罐、包装、容器、贮器，或者其任何部分。同样，作为非限制性实例，术语“基材”、“食品罐”、“食品容器”等包括可由罐端原料冲压成形且用于饮料包装的“罐端”。
本发明包括涂料组合物，其包含a)木素、b)溶剂和c)交联剂的混合物。本发明还包括涂料组合物，其包含a)木素、b)包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂和c)溶剂的混合物。此外，本发明包括涂料组合物，其包含a)木素、b)溶剂和c)酚类交联剂的混合物。所述混合物中的木素可具有负或中性电荷。
本文所用的术语“混合物”意指使用所指出的组分制得的溶液。该术语不排除存在可特意指出或未特意指出的其他组分的存在。在一些实施方案中，所述混合物中的木素不为改性的木素或者特定组分的反应产物。
所述涂料组合物的制备方法可包括将木素、溶剂和交联剂混合以形成混合物的步骤。在一些实施方案中，所述涂料组合物可通过包括如下步骤的方法制备：将木素、包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂和溶剂混合以形成混合物。此外，所述涂料组合物可通过包括如下步骤的方法制备：将木素、溶剂和酚类交联剂混合以形成混合物。
木素通常具有羟基、酚和/或羧酸官能团。木素中的各官能团的水平取决于生物质和用于将木素与生物质中的纤维素和半纤维素分离的工艺条件。木素中通常存在少量灰分、纤维素和半纤维素。在本发明的某些实施方案中，木素以占所述涂料组合物的约1-约99重量％的量存在。
硫酸盐浆、木素硫酸盐和碱木素通常在碱性条件下以显著的商业量由硬木、软木和草(稻秸秆、小麦秸秆、大麻、蔗渣等)制备。用于制备木素的各种其他生物质包括玉米秸秆、柳枝稷、城市废弃物料流等。有机溶剂型(Organosolve)木素在可包括乙醇和水且通常为酸性的溶剂混合物中制备。水解木素通常在中性或酸性条件下制备。使用各种工艺步骤以有助于生物质分解从而产生木素，包括蒸汽爆破，在通常超过100℃的温度下在水中蒸煮，暴露于超临界水、超临界二氧化碳或其他物质中，以及微生物和酶处理。所有常规制备方法均可能适用于本发明中。
适用于本发明中的木素没有限制。就非限制性实例而言，所述木素可硫酸盐浆木素、木素硫酸盐、有机溶剂型木素、水解木素、碱木素或其混合物。在一些实施方案中，所述木素具有约500-30,000的数均分子量。一般而言，具有高羧酸含量(高于约0.5meq/g羧酸)的木素，如一些碱木素通常更适于用于水基涂料中，且通常与中和剂一起使用。具有较低羧酸含量(具有小于约0.5meq/g羧酸)的木素通常更适于用于溶剂基涂料中。
所述混合物中所用的溶剂可包括水、有机溶剂或其混合物。所述溶剂可以以占所述涂料组合物的约1-约95重量％的量存在。在某些情况下，当所述涂料组合物包含水时，可使用中和剂以辅助木素在所述混合物中的分散。所述中和剂可包括而不限于氨，叔胺，作为非限制性实例例如为二甲基乙醇胺、2-二甲氨基-2-甲基-1-丙醇、三丁胺或其组合。所述中和剂可以以基于所述体系中待中和的酸和酚基的摩尔量为约0-约200％的量存在。
所述混合物可用其量占所述涂料组合物的约1-约99重量％的交联剂制备。在一些实施方案中，所述木素为未改性的木素，这意味着所述木素不为木素多元醇、不含羟基官能团、不含丙烯酸酯官能团、未用甲醛化合物改性，且未用不饱和酸改性。交联剂的非限制性列表包括环氧交联剂，例如山梨醇环氧、丁二醇二缩水甘油基醚、氧化丙烯二缩水甘油基醚等，聚合环氧交联剂，苯代胍胺甲醛，甘脲，蜜胺甲醛，苯酚甲醛交联剂，脲甲醛，异氰酸酯，封闭的异氰酸酯，及其组合。所述聚合环氧交联剂可为包含(甲基)丙烯酸缩水甘油酯的丙烯酸类(共)聚合物。该类具有(甲基)丙烯酸缩水甘油酯的丙烯酸类(共)聚合物通过为所述丙烯酸类(共)聚合物提供环氧官能团而起聚合环氧交联剂的作用。对使用酚类交联剂的实施方案而言，发现固化的涂料组合物具有优异的粘合性和高耐溶剂性。
所述包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂可在溶剂中通过添加烯属不饱和单体组分和一种或多种引发剂而制备。在一些实施方案中，在约50-约150℃下经约2小时将所述烯属不饱和单体组分和引发剂添加至所述溶剂中。所述烯属不饱和单体组分可包括而不限于(甲基)丙烯酸缩水甘油酯、乙烯基单体、丙烯酸类单体、烯丙基类单体、丙烯酰胺类单体；乙烯基酯，包括而不限于乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、苯甲酸乙烯酯、乙酸乙烯基异丙酯，和类似的乙烯基酯；乙烯基卤，包括而不限于氯乙烯、氟乙烯和偏二氯乙烯；乙烯基芳烃，包括而不限于苯乙烯、甲基苯乙烯和类似的低级烷基苯乙烯、氯苯乙烯、乙烯基甲苯、乙烯基萘；乙烯基脂族烃单体，包括而不限于α-烯烃，如作为非限制性实例的乙烯、丙烯、异丁烯和环己烯；以及共轭二烯，如作为非限制性实例的1,3-丁二烯、甲基-2-丁二烯、1,3-戊间二烯、2,3-二甲基丁二烯、异戊二烯、环己烷、环戊二烯和二环戊二烯。乙烯基烷基醚包括而不限于甲基乙烯基醚、异丙基乙烯基醚、正丁基乙烯基醚和异丁基乙烯基醚。丙烯酸类单体包括而不限于作为非限制性实例的单体，例如具有含约1-约10个碳原子的烷基酯部分的丙烯酸或甲基丙烯酸的低级烷基酯，以及丙烯酸和甲基丙烯酸的芳族衍生物。丙烯酸类单体包括作为非限制性实例的丙烯酸甲酯和甲基丙烯酸甲酯、丙烯酸乙酯和甲基丙烯酸乙酯、丙烯酸丁酯和甲基丙烯酸丁酯、丙烯酸丙酯和甲基丙烯酸丙酯、丙烯酸2-乙基己酯和甲基丙烯酸2-乙基己酯、丙烯酸环己酯和甲基丙烯酸环己酯、丙烯酸癸酯和甲基丙烯酸癸酯、丙烯酸异癸酯和甲基丙烯酸异癸酯、丙烯酸苄酯和甲基丙烯酸苄酯，与丙烯酸和甲基丙烯酸反应的各种缩水甘油基醚，丙烯酸羟烷基酯和甲基丙烯酸羟烷基酯，例如而不限限于丙烯酸羟乙酯和羟丙酯以及甲基丙烯酸羟乙酯和羟丙酯，和氨基丙烯酸酯和氨基甲基丙烯酸酯。所述烯属不饱和单体组分可占所述涂料组合物的约1-约99重量％。
适于制备所述聚合环氧交联剂的引发剂包括自由基引发剂，如过氧化苯甲酰、过辛酸叔丁酯、过苯甲酸叔丁酯、各种过碳酸盐等。一般而言，所述引发剂以占所述烯属不饱和单体组分混合物的约0.5-10重量％的量使用。适于制备所述聚合环氧交联剂的溶剂包括丁醇、丁基溶纤剂、乙酸丁酯、二甲苯和其他常规溶剂。一般而言，将所述溶剂预热至约50-约150℃的合适反应温度，且以给出约10-约90％最终聚合物固体的水平使用。
包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂为环氧官能的，因此能与木素交联，其中所述木素交联所述丙烯酸类(共)聚合物，和/或所述丙烯酸类(共)聚合物交联木素。水基木素具有羧基，其可用胺基中和剂中和，因此可以说木素的作用类似于表面活性剂，且最有可能有助于将所述(甲基)丙烯酸缩水甘油酯基丙烯酸类(共)聚合物分散至水中。
本发明的涂料组合物可包含本领域技术人员已知的常规添加剂，例如而不限于调节泡沫、降低平衡和动态表面张力、调节流变性和表面润滑性的添加剂。用量可以以任何本领域技术人员已知的方式根据所需的涂料应用和性能变化。
在一些实施方案中，将一种或多种本发明的涂料组合物施加至基材上，作为非限制性实例，例如用于容纳、碰触或接触任何类型的食品或饮料的罐、金属罐、包装、容器、贮器，罐端，或者其任何部分。在一些实施方案中，除本发明的涂料组合物之外，施加一种或多种涂料，作为非限制性实例，例如可在基材和本发明的涂料组合物之间施加底涂层。
可以以任何本领域技术人员已知的方式将所述涂料组合物施加至基材上。在一些实施方案中，将所述涂料组合物喷涂或辊涂至基材上。当喷涂施加时，作为非限制性实例，所述涂料组合物可包含约10-约30重量％聚合物固体，相对于约70-约90％水，希望的话，包括其他挥发物，例如而不限于少量溶剂。对一些应用(典型地为除喷涂之外的那些(例如辊涂))而言，作为非限制性实例，所述聚合物分散体可包含约20-约60重量％聚合物固体。在一些实施方案中，使用有机溶剂以有助于喷涂、辊涂或其他施加方法，该类溶剂包括而不限于正丁醇、2-丁氧基乙醇-1、二甲苯、甲苯及其混合物。在一些实施方案中，组合使用正丁醇和2-丁氧基乙醇-1。在一些情况下，可用已知的颜料和不透明剂对本发明的涂料组合物进行着色和/或使其不透明。对许多应用(作为非限制性实例，包括食品应用)而言，所述颜料为二氧化钛。在一些实施方案中，可通过涂料工业中已知的常规方法施加所得的含水涂料组合物。因此，作为非限制性实例，对透明和着色膜而言，可使用喷涂、辊涂、浸涂和流涂施加方法。在一些实施方案中，在施加至基材上之后，所述涂料可在约130-约250℃或更高的温度下热固化达足以进行完全固化且使其中的任何挥发性组分挥发的时间。在一些实施方案中，所述涂料组合物不能用辐射充分固化。
对意欲用作食品或饮料容器的基材而言，所述涂料组合物可以以约0.5-约15毫克聚合物涂层/平方英寸暴露基材表面的比率施加。在一些实施方案中，所述水分散性涂料以约1-约25微米的厚度施加。
实施例
参照下文非限制性实施例进一步描述本发明。应理解的是，本领域技术人员可对这些实施例进行各种改变和改造而不偏离本发明的主旨和范围。
实施例1
将1.0g Protobind 1000碱木素(ALM India)、0.2ml二甲基乙醇胺、3.2g水和0.71g苯酚甲醛交联剂(70％固体)搅拌以形成均匀溶液，并用#7刮涂棒刮涂至5×5英寸的80#电镀锡的钢板上。将所得组合物在400F下在燃气烘箱中烘烤10分钟。固化膜能耐受60次MEK双摩擦，其具有50％附着力(借助划格胶带剥离法)，2H铅笔硬度，且在20英寸磅的反面冲击下不开裂。在沸水中1小时后，所述膜不发白。
实施例2
将0.80g Protobind 1000碱木素、0.20g Cymel 303、0.24ml二甲基乙醇胺和2.8ml水搅拌以形成均匀溶液，并以与实施例1相同的方式烘烤。固化膜具有HB铅笔硬度、0％附着力、耐受100次MEK双摩擦、不发白，在20英寸磅的反面冲击之后有一些开裂。
实施例3
将1.0g有机溶剂型木素、0.36g酚醛树脂和3.6g丁基溶纤剂搅拌以形成均匀溶液，并以与实施例1相同的方式烘烤。固化膜能耐受100次MEK双摩擦、具有2H铅笔硬度、100％附着力，在20英寸磅的反面冲击之后不开裂。
实施例4
由20g甲基丙烯酸缩水甘油酯、20g苯乙烯、60g丙烯酸丁酯和6.0g过氧化苯甲酰(70％，于水中)的溶液制备丙烯酸类(共)聚合物。在120℃下将所得溶液经2小时添加至100g丁基溶纤剂中。将所得溶液保持30分钟。随后，添加1.0g过辛酸叔丁酯，然后保持90分钟。将所得丙烯酸类(共)聚合物溶液冷却。
将0.70g有机溶剂型木素、0.60g上文制得的丙烯酸类(共)聚合物溶液和1.7g丁基溶纤剂搅拌以形成均匀溶液，并以与实施例1相同的方式烘烤。固化膜具有HB铅笔硬度、100％附着力、能耐受100次MEK双摩擦，在20英寸磅的反面冲击之后不开裂且不发白。
实施例5
将0.80g LignoBoost(硫酸盐浆燃料木素，Metzo)、0.40g酚醛树脂、2.6g丁基溶纤剂和0.2g水搅拌以形成均匀溶液，并以与实施例1相同的方式烘烤。固化膜100％附着力、2H铅笔硬度、能耐受100次MEK双摩擦，在20英寸磅的反面冲击之后不开裂且不发白。
实施例6
由30g甲基丙烯酸缩水甘油酯、30g甲基丙烯酸羟丙酯、30g丙烯酸丁酯、10g甲基丙烯酸甲酯和6.0g过氧化苯甲酰(70％，于水中)的溶液制备丙烯酸类(共)聚合物。在120℃下将所得溶液经2小时添加至100g丁基溶纤剂中。将所得溶液保持30分钟。随后，添加1.0g过辛酸叔丁酯，然后保持90分钟。将所得丙烯酸类(共)聚合物溶液冷却。
将0.70g LignoBoost、0.60g所述丙烯酸类(共)聚合物溶液、0.2g水和1.5g丁基溶纤剂搅拌以形成均匀溶液，并以与实施例1相同的方式烘烤。固化膜具有2H铅笔硬度、100％附着力、能耐受100次MEK双摩擦、不发白且在20英寸磅的反面冲击之后不开裂。
Claims (17)
1.一种涂料组合物，其包含如下物质的混合物：
a)木素；
b)溶剂；和
c)交联剂；
其中所述木素具有中性或负电荷。
2.根据权利要求1的涂料组合物，其中所述木素为未改性的木素。
3.根据权利要求1或2的涂料组合物，其中所述涂料组合物能喷涂或辊涂至基材上。
4.根据权利要求1-3中任一项的涂料组合物，其中所述交联剂包括环氧交联剂、聚合环氧交联剂、苯代胍胺甲醛、甘脲、蜜胺甲醛、酚类交联剂、脲甲醛、异氰酸酯、封闭的异氰酸酯或其混合物。
5.根据权利要求4的涂料组合物，其中所述聚合环氧交联剂包含(甲基)丙烯酸缩水甘油酯。
6.根据权利要求4的涂料组合物，其中所述酚类交联剂包括苯酚甲醛。
7.一种涂料组合物，其包含如下物质的混合物：
a)木素；
b)包含(甲基)丙烯酸缩水甘油酯的聚合环氧交联剂；和
c)溶剂。
8.根据权利要求7的涂料组合物，其中所述木素为未改性的木素。
9.根据权利要求7或8的涂料组合物，其中所述木素具有中性或负电荷。
10.根据权利要求7-9中任一项的涂料组合物，其中所述涂料组合物能喷涂或辊涂至基材上。
11.一种涂料组合物，其包含如下物质的混合物：
a)木素；
b)溶剂；和
b)酚类交联剂。
12.根据权利要求11的涂料组合物，其中所述木素为未改性的木素。
13.根据权利要求11或12的涂料组合物，其中所述木素具有中性或负电荷。
14.根据权利要求11-13中任一项的涂料组合物，其中所述涂料组合物能喷涂或辊涂至基材上。
15.涂覆有根据权利要求1-6中任一项的涂料组合物的罐或包装。
16.涂覆有根据权利要求7-10任一项的涂料组合物的罐或包装。
17.涂覆有根据权利要求11-14任一项的涂料组合物的罐或包装。
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003792A (zh) * | 2017-12-27 | 2018-05-08 | 齐鲁工业大学 | 一种木素基金属保护涂料及其制备方法 |
| CN110983860A (zh) * | 2019-12-24 | 2020-04-10 | 齐鲁工业大学 | 一种纸基材料表面涂敷剂、包装纸及制备方法 |
| CN115768844A (zh) * | 2020-07-03 | 2023-03-07 | 斯道拉恩索公司 | 涂料组合物的制造工艺 |
| CN116134102A (zh) * | 2020-05-28 | 2023-05-16 | 阿尔托大学基金会 | 水基木质素颗粒-环氧表面涂层、热固性材料和粘合剂 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010008393A1 (de) * | 2010-02-10 | 2011-10-06 | Technische Universität Dresden | Substrat zur Bodenverbesserung mit Wasser speichernder Eigenschaft, Verfahren zur Herstellung und dessen Verwendung |
| BR112016006675B1 (pt) * | 2013-09-27 | 2022-05-31 | Stora Enso Oyj | Uma composição compreendendo lignina e composto epóxi para revestimento e método para fabricar a mesma e uso da mesma |
| BR112017015646A2 (pt) | 2015-01-21 | 2018-03-13 | Resinate Mat Group Inc | poliois de alto teor reciclável de poliésteres termoplásticos e lignina ou tanino |
| SE539828C2 (en) | 2016-04-29 | 2017-12-12 | Innventia Ab | Lignin-containing sealant and / or coating compositions from renewable sources |
| CN110494517B (zh) | 2017-04-07 | 2021-11-09 | 阿克佐诺贝尔国际涂料股份有限公司 | 包含羟基苯基官能聚合物和胶乳聚合物的涂料组合物 |
| WO2018185094A1 (en) * | 2017-04-07 | 2018-10-11 | Akzo Nobel Coatings International B.V. | Coating compositions containing a hydroxyphenyl functional polymer and a latex polymer |
| SE543597C2 (en) * | 2019-06-24 | 2021-04-13 | Stora Enso Oyj | Process for preparing a bonding resin |
| SE543776C2 (en) | 2019-10-23 | 2021-07-20 | Rise Innventia Ab | Lignin-containing sealant and/or coating compositions from renewable sources |
| WO2021124129A1 (en) * | 2019-12-20 | 2021-06-24 | Stora Enso Oyj | Process for preparing a bonding resin |
| BR112022011952A2 (pt) * | 2019-12-20 | 2022-09-06 | Stora Enso Oyj | Processo para a preparação de uma resina de ligação |
| SE545325C2 (en) * | 2019-12-20 | 2023-07-04 | Stora Enso Oyj | Process for the preparation of a bonding resin |
| SE544233C2 (en) * | 2019-12-20 | 2022-03-08 | Stora Enso Oyj | Process for preparing a bonding resin from an aqueous lignin solution, the bonding resin, and use of the bonding resin |
| CA3202309A1 (en) * | 2020-12-22 | 2022-06-30 | Mojgan NEJAD | Lignin-based epoxide prepolymers, polymers, related compositions, and related methods |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1176643A (zh) * | 1995-12-29 | 1998-03-18 | K·R·库泼 | 木素基多元醇 |
| CN1651478A (zh) * | 2005-01-05 | 2005-08-10 | 福州大学 | 高沸醇木质素聚氨酯的制备 |
| CN1958636A (zh) * | 2006-10-21 | 2007-05-09 | 福州大学 | 酶解木质素聚氨酯的原料配方及其制备方法 |
| CN101935493A (zh) * | 2010-09-28 | 2011-01-05 | 江苏冶建防腐材料有限公司 | 一种水性无毒长效防污涂料及其制备方法 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857354A (en) * | 1955-07-20 | 1958-10-21 | Du Pont | Process of making glycidyl methacrylate polymer composition containing same, and product coated therewith |
| US3787520A (en) * | 1971-08-16 | 1974-01-22 | Ford Motor Co | Powdered coating compositions containing a glycidyl ester copolymer,a phenolic hydroxy crosslinking agent,and a flow control agent |
| US3886101A (en) * | 1974-07-08 | 1975-05-27 | Georgia Pacific Corp | Phenolic adhesives |
| US4017430A (en) * | 1975-06-23 | 1977-04-12 | Georgia-Pacific Corporation | Coating composition |
| CA1057438A (en) * | 1976-01-13 | 1979-06-26 | Michael R. Clarke | Methylolated kraft lignin-base resins |
| US4130515A (en) * | 1977-06-30 | 1978-12-19 | Georgia-Pacific Corporation | Lignin-based composition board binder comprising a copolymer of a lignosulfonate, melamine and an aldehyde |
| US4292214A (en) * | 1979-02-21 | 1981-09-29 | Blount David H | Process for the production of polyurethane products |
| GB2048271B (en) | 1979-03-15 | 1983-08-03 | Mitsui Toatsu Chemicals | Phenolic resin epoxide rubber compositions |
| US4486378A (en) * | 1980-05-07 | 1984-12-04 | Toyo Seikan Kaisha Ltd. | Plastic bottles and process for preparation thereof |
| US4370368A (en) * | 1980-05-07 | 1983-01-25 | Toyo Seikan Kaisha, Ltd. | Plastic bottles and process for preparation thereof |
| US4320036A (en) * | 1980-10-16 | 1982-03-16 | American Can Company | Ligno-novolak resin molding compositions |
| DE3173472D1 (en) * | 1980-10-31 | 1986-02-20 | Toyo Seikan Kaisha Ltd | Laminated plastic container and process for preparation thereof |
| US4486557A (en) * | 1981-11-11 | 1984-12-04 | Atlantic Richfield Company | Organic polyisocyanate-liquid aromatic epoxide-lignin adhesive binder compositions |
| DE3908104A1 (de) * | 1989-03-13 | 1990-09-20 | Basf Lacke & Farben | Beschichtungsmasse, verfahren zu ihrer herstellung sowie die verwendung der beschichtungsmasse, insbesondere zur aussenlackierung von tiefgezogenen dosen |
| US5173527A (en) * | 1991-05-15 | 1992-12-22 | Forintek Canada Corp. | Fast cure and pre-cure resistant cross-linked phenol-formaldehyde adhesives and methods of making same |
| CA2070500C (en) * | 1991-06-13 | 1997-10-14 | Ted Mcvay | Reactive phenolic resin modifier |
| US5192361A (en) * | 1992-01-27 | 1993-03-09 | Westvaco Corporation | Submicron lignin-based binders for water-based black ink formulations |
| DE4241513A1 (de) * | 1992-12-10 | 1994-06-16 | Ruetgerswerke Ag | Bindemittelgemisch |
| DE4437720A1 (de) * | 1994-10-21 | 1996-04-25 | Basf Ag | Strahlungshärtbare Beschichtungen aus Basis von Ligninderivaten |
| SG47174A1 (en) * | 1995-09-18 | 1998-03-20 | Ibm | Cross-linked biobased materials and fabricating methods thereof |
| TW354451B (en) * | 1995-09-18 | 1999-03-11 | Ibm | Method of fabricating cross-linked biobased materials and structures fabricated therewith a method comprising the step of: forming the mixture of polymer and cross-linked agent |
| TW344191B (en) | 1995-09-18 | 1998-11-01 | Ibm | Cross-linked biobased materials and uses thereof |
| DE59705574D1 (de) * | 1996-08-12 | 2002-01-10 | Novamont Spa | Biologisch abbaubare zusammensetzung |
| US6025452A (en) * | 1996-12-27 | 2000-02-15 | Kurple; Kenneth R. | Lignin based polyols |
| US5891952A (en) * | 1997-10-01 | 1999-04-06 | Henkel Corporation | Aqueous compositions containing polyphenol copolymers and processes for their preparation |
| AUPQ544900A0 (en) * | 2000-02-04 | 2000-02-24 | Commonwealth Scientific And Industrial Research Organisation | Treatment of cellulosic material |
| US6465587B1 (en) * | 2000-12-08 | 2002-10-15 | Hercules Incorporated | Polymeric fluid loss additives and method of use thereof |
| EP1258330A1 (fr) * | 2001-05-10 | 2002-11-20 | Universite Catholique De Louvain | Procédé de traitement d'un matériau poreux |
| US7252735B2 (en) * | 2002-05-13 | 2007-08-07 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| US7026390B2 (en) * | 2002-12-19 | 2006-04-11 | Owens Corning Fiberglas Technology, Inc. | Extended binder compositions |
| US20050032967A1 (en) * | 2003-07-09 | 2005-02-10 | Roberts Michael G. | Water-based coating composition for waterproofing walls |
| US20050058822A1 (en) * | 2003-08-04 | 2005-03-17 | Ittel Steven Dale | Fiber-reinforced thermoplastic matrices |
| FR2863617B1 (fr) * | 2003-12-15 | 2006-01-21 | Rhodia Chimie Sa | Polymeres zwitterioniques comprenant des unites de type betaine et utilisation de polymeres zwitterioniques dans des fluides de forage. |
| US7183339B2 (en) * | 2004-11-02 | 2007-02-27 | Shen Kuo C | Method for making dimensionally stable composite products from lignocelluloses |
| AR065041A1 (es) * | 2007-01-26 | 2009-05-13 | Du Pont | Composicion que comprende un biopolimero |
| CN102395621A (zh) * | 2009-03-20 | 2012-03-28 | Sika技术股份公司 | 用于制备化学改性的木质素的分解产物的方法 |
| CA2725896C (en) * | 2009-12-30 | 2013-11-19 | Rohm And Haas Company | Carboxylated lignin based binders |
| EP2524012B1 (de) * | 2010-01-11 | 2014-12-03 | Liebherr-Hausgeräte Ochsenhausen GmbH | Oberflächenbeschichtungen mit anti-eis eigenschaften |
| DE102010008393A1 (de) * | 2010-02-10 | 2011-10-06 | Technische Universität Dresden | Substrat zur Bodenverbesserung mit Wasser speichernder Eigenschaft, Verfahren zur Herstellung und dessen Verwendung |
| WO2011097719A1 (en) * | 2010-02-15 | 2011-08-18 | Lignol Innovations Ltd. | Binder compositions comprising lignin derivatives |
| EP2431101A1 (en) * | 2010-09-16 | 2012-03-21 | Tooling Invest A/S | Method of working a workpiece with a coating of a lignin-derived substance, wooden element with a coating of such lignin-derived substance, and structures, interior or exterior, with such wooden element |
| TW201219526A (en) * | 2010-11-11 | 2012-05-16 | Ind Tech Res Inst | Adhesive composition |
| CN102558507B (zh) * | 2010-12-14 | 2013-12-25 | 财团法人工业技术研究院 | 生质环氧树脂的原料及生质环氧树脂的制备方法 |
| ES2602499T5 (es) * | 2011-02-04 | 2022-05-12 | Mosca Gmbh | Flejes de materias primas renovables |
| EP2714791A1 (en) * | 2011-05-25 | 2014-04-09 | Shell Internationale Research Maatschappij B.V. | Asphalt composition |
| JP5479530B2 (ja) * | 2011-06-23 | 2014-04-23 | ダウ グローバル テクノロジーズ エルエルシー | 再分散可能なエポキシ粉体 |
| US20130116383A1 (en) * | 2011-11-03 | 2013-05-09 | Ut-Battelle, Llc | Lignin-derived thermoplastic co-polymers and methods of preparation |
| US9006369B2 (en) * | 2012-08-01 | 2015-04-14 | Empire Technology Development Llc | Water based lignin epoxy resins, methods of using and making the same |
| US20160024337A1 (en) * | 2013-03-15 | 2016-01-28 | Akzo Nobel Coatings International B.V. | Coating Compositions Having Hydroxyl Phenyl Functional Polymers |
| BR112016006675B1 (pt) * | 2013-09-27 | 2022-05-31 | Stora Enso Oyj | Uma composição compreendendo lignina e composto epóxi para revestimento e método para fabricar a mesma e uso da mesma |
| EP3058040A4 (en) * | 2013-10-18 | 2017-06-21 | Queensland University Of Technology | Lignin-based waterproof coating |
| WO2016080469A1 (ja) * | 2014-11-20 | 2016-05-26 | 住友ベークライト株式会社 | リグニン樹脂組成物、硬化物および成形物 |
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2013
- 2013-12-17 MX MX2015007497A patent/MX369868B/es active IP Right Grant
- 2013-12-17 CN CN201380063787.XA patent/CN104995236B/zh not_active Expired - Fee Related
- 2013-12-17 RU RU2015128097A patent/RU2652183C2/ru active
- 2013-12-17 MY MYPI2015701943A patent/MY171821A/en unknown
- 2013-12-17 EP EP13805895.3A patent/EP2935411B1/en not_active Not-in-force
- 2013-12-17 AU AU2013363709A patent/AU2013363709B2/en not_active Ceased
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- 2013-12-17 KR KR1020157016950A patent/KR102166188B1/ko active IP Right Grant
- 2013-12-17 CA CA2893088A patent/CA2893088C/en active Active
- 2013-12-17 US US14/652,480 patent/US20150344737A1/en not_active Abandoned
- 2013-12-17 WO PCT/EP2013/076820 patent/WO2014095800A1/en active Application Filing
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1176643A (zh) * | 1995-12-29 | 1998-03-18 | K·R·库泼 | 木素基多元醇 |
| CN1651478A (zh) * | 2005-01-05 | 2005-08-10 | 福州大学 | 高沸醇木质素聚氨酯的制备 |
| CN1958636A (zh) * | 2006-10-21 | 2007-05-09 | 福州大学 | 酶解木质素聚氨酯的原料配方及其制备方法 |
| CN101935493A (zh) * | 2010-09-28 | 2011-01-05 | 江苏冶建防腐材料有限公司 | 一种水性无毒长效防污涂料及其制备方法 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003792A (zh) * | 2017-12-27 | 2018-05-08 | 齐鲁工业大学 | 一种木素基金属保护涂料及其制备方法 |
| CN110983860A (zh) * | 2019-12-24 | 2020-04-10 | 齐鲁工业大学 | 一种纸基材料表面涂敷剂、包装纸及制备方法 |
| CN110983860B (zh) * | 2019-12-24 | 2022-06-07 | 齐鲁工业大学 | 一种纸基材料表面涂敷剂、包装纸及制备方法 |
| CN116134102A (zh) * | 2020-05-28 | 2023-05-16 | 阿尔托大学基金会 | 水基木质素颗粒-环氧表面涂层、热固性材料和粘合剂 |
| CN115768844A (zh) * | 2020-07-03 | 2023-03-07 | 斯道拉恩索公司 | 涂料组合物的制造工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2013363709A1 (en) | 2015-06-11 |
| US20180355119A1 (en) | 2018-12-13 |
| MY171821A (en) | 2019-10-31 |
| US20150344737A1 (en) | 2015-12-03 |
| EP2935411B1 (en) | 2019-04-24 |
| CA2893088A1 (en) | 2014-06-26 |
| BR112015013437A2 (pt) | 2017-07-11 |
| AU2013363709B2 (en) | 2016-10-20 |
| EP2935411A1 (en) | 2015-10-28 |
| HK1215270A1 (zh) | 2016-08-19 |
| MX2015007497A (es) | 2015-09-04 |
| KR20150097554A (ko) | 2015-08-26 |
| CA2893088C (en) | 2020-10-20 |
| KR102166188B1 (ko) | 2020-10-16 |
| CN104995236B (zh) | 2017-11-28 |
| US10913824B2 (en) | 2021-02-09 |
| RU2015128097A (ru) | 2017-01-25 |
| WO2014095800A1 (en) | 2014-06-26 |
| RU2652183C2 (ru) | 2018-04-25 |
| MX369868B (es) | 2019-11-25 |
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