CN103443209B - 用于金属的可辐射固化涂料组合物 - Google Patents
用于金属的可辐射固化涂料组合物 Download PDFInfo
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- CN103443209B CN103443209B CN201180062309.8A CN201180062309A CN103443209B CN 103443209 B CN103443209 B CN 103443209B CN 201180062309 A CN201180062309 A CN 201180062309A CN 103443209 B CN103443209 B CN 103443209B
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- Prior art keywords
- methyl
- coating composition
- acrylate
- acrylic acid
- radiation
- 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.)
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- 239000008199 coating composition Substances 0.000 title claims abstract description 39
- 229910052751 metal Inorganic materials 0.000 title claims description 12
- 239000002184 metal Substances 0.000 title claims description 12
- -1 acrylic compound Chemical class 0.000 claims abstract description 40
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 238000004806 packaging method and process Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- VALXVSHDOMUUIC-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phosphoric acid Chemical group OP(O)(O)=O.CC(=C)C(O)=O VALXVSHDOMUUIC-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 11
- 239000012948 isocyanate Substances 0.000 abstract description 10
- 150000002513 isocyanates Chemical class 0.000 abstract description 8
- 230000008719 thickening Effects 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000003085 diluting agent Substances 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UADUAXMDVVGCGW-UHFFFAOYSA-N propanoic acid;zirconium Chemical compound [Zr].CCC(O)=O UADUAXMDVVGCGW-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F220/10—Esters
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/31692—Next to addition polymer from unsaturated monomers
- Y10T428/31699—Ester, halide or nitrile of addition polymer
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- Engineering & Computer Science (AREA)
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- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
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Abstract
提供可辐射固化涂料组合物的各个实施方案。在一个实施方案中,可辐射固化涂料组合物包含(甲基)丙烯酸酯官能化合物和增粘(甲基)丙烯酸酯化合物。所述可辐射固化涂料组合物还可包含(甲基)丙烯酸酯官能化合物、聚(甲基)丙烯酸酯和反应性稀释剂。所述(甲基)丙烯酸酯官能化合物可由多官能异氰酸酯、多元醇和羟基官能(甲基)丙烯酸酯在催化剂的存在下反应而制备。
Description
发明背景
本公开内容涉及可提供有用的涂层和包装材料如金属罐的涂覆表面的可辐射固化涂料组合物。目前可得的可辐射固化涂料如通过紫外线(“UV”)辐射或电子束辐射(“EB”)固化的那些倾向于为不可挠曲的固化涂层,其倾向于更高的收缩水平。因此,迄今本领域技术人员认识到使用这种固化化学的涂料在直接金属粘合性、可成形性和耐干馏性方面是不合适的,以及在挠性包装工业内的粘合性和延展性方面的应用中受限。解决这些顾虑的尝试可导致依赖于如下方面的缺点:(1)在引发辐射固化以前需要高温闪蒸的方法,如在聚氨酯分散体(“PUD”)中,(2)阳离子化学,其遭遇固化的湿度抑制、光引发剂和目前由于供应问题导致的高成本的缺点,(3)高温烘烤、后辐射固化的应用,和/或底涂层的应用以赋予粘合性,和/或(4)依赖于常规溶剂和水基热固性化学,其回归至释放挥发性有机化合物(“VOC”)、BADGE/NOGE结构部分的缺点。因此,解决这些问题中的一个或多个,同时还省去辐射固化涂料化学中的这些缺点中的一个或多个的任何组合物会提供一个或多个使用优点,同时积极影响安全性、健康和环境考虑。
尽管增粘剂是本领域中已知的,令人惊讶的是,比供应商文献或其它公开信息中常用的更高的这些化合物含量提供粘合性的显著改进并且不导致固化涂层抗发白性的严重问题。较高含量尤其用于不经预处理的“仅清洁的”金属基材和无铬基材上。
发明概述
本发明涵盖包含(甲基)丙烯酸酯官能化合物和增粘(甲基)丙烯酸酯化合物的可辐射固化涂料组合物以及包含(甲基)丙烯酸酯官能化合物、聚(甲基)丙烯酸酯和反应性稀释剂的可辐射固化涂料组合物。本发明还涵盖包含金属基材和置于基材上的可辐射固化涂料组合物的包装。
另外,本发明涵盖涂覆包装的方法,所述方法包括:a)制备如本文所述的可辐射固化涂料组合物;和b)将涂料组合物施涂于包装上。发现本发明可辐射固化涂层是硬的、挠性的,并显示出在金属基材上的良好粘合性。本发明涂膜可以最小的白化和最小的粘合性损失经得住干馏条件。
发明详述
本发明涵盖包含(甲基)丙烯酸酯官能化合物和增粘(甲基)丙烯酸酯化合物的可辐射固化涂料组合物以及包含(甲基)丙烯酸酯官能化合物、聚(甲基)丙烯酸酯和反应性稀释剂的可辐射固化涂料组合物。作为非限制性实例,(甲基)丙烯酸酯官能化合物可由多官能异氰酸酯、多元醇和羟基官能(甲基)丙烯酸酯在催化剂的存在下反应而制备。所述(甲基)丙烯酸酯官能化合物和增粘(甲基)丙烯酸酯化合物各自可为单体、低聚物或其组合,提及单体,应当理解包括低聚物,反之亦然。
在一些实施方案中,所述(甲基)丙烯酸酯官能化合物以至多约50重量%涂料组合物的量存在。所述(甲基)丙烯酸酯官能化合物可由本领域中已知的各种材料制备,例如而不限于(甲基)丙烯酸酯官能聚酯、(甲基)丙烯酸酯官能聚丙烯酸酯、(甲基)丙烯酸酯官能聚醚、(甲基)丙烯酸酯官能聚碳酸酯、油多元醇醚、(甲基)丙烯酸酯官能氨基甲酸酯、WO2008/151286(通过引用将其内容并入本文中)的(甲基)丙烯酸酯官能化合物或其组合。一种可能的(甲基)丙烯酸酯官能化合物为氨基甲酸酯,其容易地但不仅仅由多官能异氰酸酯、多元醇和羟基官能(甲基)丙烯酸酯在催化剂的存在下反应而制备。
作为非限制性实例,所述增粘(甲基)丙烯酸酯化合物可为磷酸酯(甲基)丙烯酸系官能单体、羧酸酯(甲基)丙烯酸系官能单体、磷酸酯(甲基)丙烯酸系官能低聚物、羧酸酯(甲基)丙烯酸系官能低聚物或其组合。在一些实施方案中,所述磷酸酯(甲基)丙烯酸系官能单体可包括甲基丙烯酸的磷酸酯或羟基官能酯。羧酸酯(甲基)丙烯酸系官能单体/低聚物可包括而不限于羧酸官能酯、羧酸官能醚及其组合。在本发明的某些实施方案中,所述磷酸酯(甲基)丙烯酸系官能单体/低聚物可以以至多约12重量%涂料组合物的量存在。所述羧酸酯(甲基)丙烯酸系官能单体/低聚物可以以约0.5-约50重量%涂料组合物的量存在。
所述增粘(甲基)丙烯酸酯化合物可以以至多约65重量%总涂料组合物成膜组分的量存在。
在本发明一些实施方案中,聚(甲基)丙烯酸酯以至多约25重量%涂料组合物或约5-约15重量%的量存在。聚(甲基)丙烯酸酯可包括而不限于三环癸基二甲醇二丙烯酸酯、二丙二醇二丙烯酸酯等,及其组合。
所述反应性稀释剂可以以至多约95重量%涂料组合物或约20-约60重量%的量存在。反应性稀释剂可包括而不限于单(甲基)丙烯酸酯。
用于本发明中的多官能异氰酸酯包括但不限于异氰酸酯、二异氰酸酯、多异氰酸酯、脂族异氰酸酯、芳族异氰酸酯、二-六亚甲基、聚六亚甲基、己烷二异氰酸酯、异佛尔酮(isophorane)、MDI及其组合。
用于本发明中的多元醇包括但不限于聚酯、二醇、醇、聚碳酸酯、聚丙二醇、聚乙二醇、聚氧化四亚甲基及其组合。在本发明一些实施方案中,所述多元醇具有约100-约10,000或约500-约5000的分子量。
合适的羟基官能(甲基)丙烯酸酯包括但不限于羟基单体、(甲基)丙烯酸4-羟基丁酯、丁二醇单(甲基)丙烯酸酯、(甲基)丙烯酸羟基丙酯、(甲基)丙烯酸羟基乙酯、增链(甲基)丙烯酸羟基酯、聚己酸内酯(甲基)丙烯酸酯及其组合。所述羟基官能(甲基)丙烯酸酯的量可基于(甲基)丙烯酸酯官能化合物的重量为约5-约95重量%,在其它实例中,基于(甲基)丙烯酸酯官能化合物的重量为约25-约75重量%。
在本发明一些实施方案中,多官能异氰酸酯/多元醇/羟基官能(甲基)丙烯酸酯的摩尔比为约1/0.1-2/0.2-5、约1/0.25-0.75/0.5-2.5或约1/0.5/2。基于重量,该比可为约1-约75%的多官能异氰酸酯:至多约90%的多元醇:约1-约99%的羟基官能(甲基)丙烯酸酯。在一些实施方案中,羟基官能度相对于异氰酸酯官能度稍微过量,其允许反应进行至至少99%的多官能异氰酸酯转化率。
其它羟基官能材料可与羟基官能(甲基)丙烯酸酯一起包含在内。其它羟基官能材料可包括但不限于醇、二醇、多元醇、聚酯、聚醚(作为非限制性实例,例如苄醇、三羟甲基丙烷、聚丙二醇、己二醇)及其组合。
所述催化剂可为适于聚合的催化剂,例如而不限于锡催化剂如二月桂酸二丁基锡或氧化二丁基锡、锆催化剂如丙酸锆、铋催化剂如新癸酸铋、叔胺催化剂如三亚乙基二胺或其组合。催化剂的量可为约1-约10,000ppm、约10-约1,000ppm或约20-约200ppm。通常方便的是使用在有机溶剂中的溶液形式的催化剂。合适溶剂的实例包括而不限于芳族烃溶剂、脂环族极性溶剂(例如脂环族酮,包括环己酮)、极性脂族溶剂(例如烷氧基链烷醇,包括2-甲氧基乙烷)、所述二醇原料及其组合。
空气气氛和有效的抑制剂如甲氧基氢醌、氢醌、二叔丁基氢醌、丁基化羟基甲苯、吩噻嗪或其组合可用于防止所述羟基官能(甲基)丙烯酸酯单体/低聚物的自由基聚合。抑制剂可以以约10-约10,000ppm的量存在。所述多官能异氰酸酯、多元醇和羟基官能(甲基)丙烯酸酯的反应可在约环境温度至约70℃或约110℃,在其它实例中,约90-约100℃的温度下进行。通常,至少90%转化率,在一些实施方案中至少99%的异氰酸酯基团转化率可在90℃下在约1小时内得到。另外,可在反应期间加入稀释剂以降低粘度,作为非限制性实例,例如自由基反应性物种,例如(甲基)丙烯酸酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸叔丁基环己基酯、三环癸基二甲醇二(甲基)丙烯酸或其组合。稀释剂可以以至多约75%或更多的总批料重量的量存在。
本发明的各个实施方案提供当用低能固化如电子束固化固化时,基本不含BADGE和NOGE的辐射固化涂料组合物。本文所述各种辐射固化涂料组合物具有改进的挠性,且例如比具有其它(甲基)丙烯酸酯涂料的涂层更具挠性。本发明涂料组合物还可提供根据已知用于刚性包装应用的最常用干馏试验的刚性包装应用的耐干馏性。本发明的可固化涂料组合物可不需要底涂层而使用以直接接触金属基材。所述涂料组合物可以以本领域技术人员已知的任何方式施涂于基材上。
给出以下实施例以阐述所述体系和方法,且不应当理解为对其范围或精神的限制。
实施例
实施例1
氨基甲酸酯低聚物的制备
在1升烧瓶中将99g的BayerN-3900与200g聚丙二醇2000、153g丙烯酸异冰片酯、57.6g丙烯酸4-羟基丁酯和0.15g吩噻嗪混合。将混合物置于在空气保护下的90℃热水浴中并搅拌。向所得混合物中加入0.5ml的二月桂酸二丁基锡的10%甲乙酮溶液。将所得混合物保持2小时,然后冷却。
实施例2
在搅拌下加入以下成分,同时在中速搅拌下进行混合操作。将最终涂料划涂在金属基材上并在3兆拉德/90千伏最小设置的电子束下固化。
*评定0-5,5=优异
**白化评定:5-无白化,4-非常轻微,3-轻微,2-白化,1和0-失效
Claims (12)
1.一种可辐射固化涂料组合物,其包含:
a)(甲基)丙烯酸酯官能聚醚;和
b)至少一种增粘化合物,其中所述增粘化合物选自磷酸酯(甲基)丙烯酸系官能单体、羧酸酯(甲基)丙烯酸系官能单体、磷酸酯(甲基)丙烯酸系官能低聚物、羧酸酯(甲基)丙烯酸系官能低聚物或其组合。
2.根据权利要求1的涂料组合物,其中所述增粘化合物以2-40重量%的量存在。
3.根据权利要求1的涂料组合物,其中所述(甲基)丙烯酸酯官能聚醚以0.5-45重量%所述涂料组合物的量存在。
4.根据权利要求1的涂料组合物,其中所述磷酸酯(甲基)丙烯酸系官能单体为(甲基)丙烯酸的磷酸酯。
5.根据权利要求1的涂料组合物,其中所述羧酸酯(甲基)丙烯酸系官能单体或羧酸酯(甲基)丙烯酸系官能低聚物为羧酸官能(甲基)丙烯酸酯、羧酸官能(甲基)丙烯酸酯醚或其组合。
6.根据权利要求1的涂料组合物,其中所述磷酸酯(甲基)丙烯酸系官能单体或磷酸酯(甲基)丙烯酸系官能低聚物以至多12重量%的涂料组合物的量存在。
7.根据权利要求1的涂料组合物,其中所述羧酸酯(甲基)丙烯酸系官能单体或羧酸酯(甲基)丙烯酸系官能低聚物以0.5-50重量%的涂料组合物的量存在。
8.根据权利要求1的涂料组合物,其进一步包含至少一种多官能(甲基)丙烯酸酯。
9.一种包装,其包含:金属基材;和根据权利要求1的可辐射固化涂料组合物。
10.根据权利要求9的包装,其中所述可辐射固化涂料组合物直接接触金属基材而不具有底涂层。
11.一种涂覆包装的方法,其包括:
a)制备根据权利要求1的可辐射固化涂料组合物;和
b)将所述可辐射固化涂料组合物施涂于包装上。
12.根据权利要求11的方法,其中所述包装为金属基材。
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MX2011009154A (es) | 2009-03-05 | 2011-10-10 | Akzo Nobel Coatings Int Bv | Polioles de aceite con funcion de hidroxilo y composiciones de recubrimiento preparadas de polioles de aceite con funcion de hidroxilo. |
MX367933B (es) | 2011-12-21 | 2019-09-12 | Akzo Nobel Coatings Int Bv | Composiciones de recubrimiento a base de solvente. |
WO2013092539A1 (en) | 2011-12-21 | 2013-06-27 | Akzo Nobel Coatings International B.V. | Water-based coating compositions |
CN103254353A (zh) * | 2013-04-27 | 2013-08-21 | 晟通科技集团有限公司 | 一种水溶性丙烯酸树脂及用其制作的亲水涂料 |
EP3204444B1 (en) * | 2014-10-08 | 2023-08-30 | Basf Se | Phosphate ester-modified acrylic polyols |
EP3289033A1 (en) | 2015-05-01 | 2018-03-07 | LORD Corporation | Adhesive for rubber bonding |
CN109890929A (zh) | 2016-09-19 | 2019-06-14 | 陶氏环球技术有限责任公司 | 双组分无溶剂粘合剂组合物和制造其的方法 |
CN108977047A (zh) * | 2018-05-23 | 2018-12-11 | 无锡万博涂料化工有限公司 | 一种基于eb固化的卷材涂料 |
KR102315050B1 (ko) * | 2020-04-07 | 2021-10-21 | 대주전자재료 주식회사 | 고온 이형 가능한 도전성 접착제 및 태양 전지 모듈 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5128391A (en) * | 1988-02-24 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal containing organofunctional silane adhesion promoter |
EP1818349A1 (en) * | 2006-02-13 | 2007-08-15 | Cytec Surface Specialties, S.A. | Radiation curable compositions |
CN101096472A (zh) * | 2006-06-26 | 2008-01-02 | 上海飞凯光电材料有限公司 | 辐射固化材料粘接性能促进剂 |
Family Cites Families (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3929929A (en) | 1973-05-29 | 1975-12-30 | Ici America Inc | Vinyl urethane resins |
US4025548A (en) | 1974-02-04 | 1977-05-24 | The O'brien Corporation | Radiation curable oligomers |
US4153778A (en) | 1978-03-30 | 1979-05-08 | Union Carbide Corporation | Acrylyl capped urethane oligomers |
US4508916A (en) | 1979-04-11 | 1985-04-02 | Minnesota Mining And Manufacturing Company | Curable substituted urethane acrylates |
AU530007B2 (en) | 1981-04-02 | 1983-06-30 | Dow Chemical Company, The | Laminated container body and manufacture thereof |
US4452374A (en) | 1981-04-02 | 1984-06-05 | The Dow Chemical Company | Manufacture of draw-redraw cans using an irradiated film laminated or extrusion coated steel sheet material |
NZ205206A (en) | 1982-08-12 | 1986-07-11 | Scm Corp | Water-dispersed coating compositions containing alkylol acrylamide-containing copolymers |
JPS6053570A (ja) | 1983-09-05 | 1985-03-27 | Toray Ind Inc | 電子線キユア性塗料組成物 |
JPS60112865A (ja) | 1983-11-25 | 1985-06-19 | Nippon Paint Co Ltd | プレコ−ト用塗料組成物及びプレコ−ト鋼板 |
US4607084A (en) | 1984-06-11 | 1986-08-19 | Celanese Specialty Resins, Inc. | Radiation curable acrylated polyurethane oligomer compositions |
JPS6392618A (ja) | 1986-10-07 | 1988-04-23 | Sumitomo Chem Co Ltd | リン酸エステルを含む光硬化性組成物 |
US5128387A (en) | 1987-07-28 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal |
KR950704387A (ko) | 1992-11-24 | 1995-11-20 | 캐롤린 에이. 베이츠 | 방사선 경화성 올리고머 및 이로부터 제조된 자기 기록 매체(radiati0n curable oligomers and magnetic rec0rding media prepared therefrom) |
JPH0859770A (ja) | 1994-08-15 | 1996-03-05 | Dainippon Ink & Chem Inc | ポリウレタンポリ尿素架橋微粒子分散体及びその製造方法 |
JPH0931150A (ja) | 1995-05-15 | 1997-02-04 | Dainippon Ink & Chem Inc | ウレタンプレポリマー、活性エネルギー線硬化型水性ポリウレタン樹脂組成物、及びその製造方法 |
US5578693A (en) | 1995-09-05 | 1996-11-26 | Bomar Specialties Company | Multifunctional terminally unsaturated urethane oligomers |
US6743879B1 (en) | 1996-04-10 | 2004-06-01 | Hehr International Inc. | Methacrylic-urethane oligomers, method of preparation and oligomer-containing resin compositions |
JPH10204325A (ja) | 1997-01-27 | 1998-08-04 | Toyo Ink Mfg Co Ltd | 電子線硬化型塗料およびその硬化方法 |
KR100593519B1 (ko) * | 1997-04-22 | 2006-06-28 | 코닌클리즈케 디에스엠 엔.브이. | 액상 경화성 수지 조성물 |
US6488993B2 (en) | 1997-07-02 | 2002-12-03 | William V Madigan | Process for applying a coating to sheet metal |
JP4288691B2 (ja) | 1999-04-15 | 2009-07-01 | 日立化成工業株式会社 | 光硬化性樹脂組成物を含む塗料を用いた硬化塗膜の製造法 |
JP2001038452A (ja) | 1999-07-28 | 2001-02-13 | Daido Steel Co Ltd | 連続鋳造方法 |
DE19960693A1 (de) | 1999-12-16 | 2001-07-19 | Dupont Performance Coatings | Verfahren zur anodischen Elektrotauchlackierung, sowie Elektrotauchlacke |
US6306468B1 (en) | 2000-02-25 | 2001-10-23 | Polymeric Processes Inc. | Metal tube coating process |
US7115676B2 (en) * | 2000-05-18 | 2006-10-03 | Henkel Corporation | Adhesive compositions for bonding passive substrates |
EP1317517A1 (en) | 2000-09-14 | 2003-06-11 | Dsm N.V. | Coating compositions for plastic substrates |
DE10048849A1 (de) | 2000-10-02 | 2002-04-18 | Basf Coatings Ag | Verfahren zur Herstellung eines thermisch und mit aktinischer Strahlung härtbaren Mehrkomponentensystems und seine Verwendung |
EP1254936B1 (en) | 2001-05-04 | 2007-03-14 | Rohm And Haas Company | Method for preparing a laminate |
US6433091B1 (en) * | 2001-05-10 | 2002-08-13 | Henkel Loctite Corporation | Adhesive composition |
US20020172760A1 (en) | 2001-05-17 | 2002-11-21 | Shu An | Apparatus and process for the post-production repair of converted can ends |
US6974665B2 (en) | 2001-09-06 | 2005-12-13 | University Of Nebraska | In situ screening to optimize variables in organic reactions |
US20030079333A1 (en) | 2001-10-29 | 2003-05-01 | Guthrie Joseph D. | Process for making a metal-polymer composite having an irradiated polymer coating |
US20030225149A1 (en) | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
US6696106B1 (en) | 2002-09-11 | 2004-02-24 | Alcoa Inc. | Primer for radiation curable coating compositions |
US7122684B2 (en) | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
JP2005060631A (ja) * | 2003-08-20 | 2005-03-10 | Jsr Corp | 放射線硬化性液状樹脂組成物 |
US7109252B2 (en) | 2003-11-25 | 2006-09-19 | Bomar Specialties Company | TMXDI-based oligomer and formulations containing it |
US6989407B2 (en) | 2004-01-09 | 2006-01-24 | Northwest Coatings, Llc | Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers |
CN1651533A (zh) * | 2004-01-13 | 2005-08-10 | 上海飞凯光电材料有限公司 | 辐射固化涂料及其应用 |
DE102004012902A1 (de) | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
EP1616710A1 (de) | 2004-07-01 | 2006-01-18 | Alcan Technology & Management Ltd. | Verfahren zur Herstellung eines Verpackungsmaterials |
US7297748B2 (en) | 2004-08-31 | 2007-11-20 | Rhodia Inc. | Direct to metal polyurethane coating compositions |
US7368171B2 (en) | 2004-09-03 | 2008-05-06 | H.B. Fuller Licensing & Financing, Inc. | Laminating adhesive, laminate including the same, and method of making a laminate |
CN101171317B (zh) | 2005-05-02 | 2011-11-23 | 氰特表面技术有限公司 | 粘合剂组合物和方法 |
JP4899535B2 (ja) | 2005-08-17 | 2012-03-21 | セントラル硝子株式会社 | 防曇性被膜及び防曇性物品 |
US20070088111A1 (en) | 2005-08-26 | 2007-04-19 | Ppg Industries Ohio, Inc. | Coating compositions exhibiting corrosion resistance properties, related coated substrates, and methods |
JP5021194B2 (ja) | 2005-09-15 | 2012-09-05 | Hoya株式会社 | 硬化性組成物及びそれを用いた光学部材 |
KR100725249B1 (ko) * | 2005-12-20 | 2007-06-04 | (주)디피아이 홀딩스 | 철재 도장용 자외선 경화 도료 |
CN100343344C (zh) | 2005-12-26 | 2007-10-17 | 中国化工建设总公司常州涂料化工研究院 | 用于金属镀膜表面防护的紫外光固化涂料 |
ATE489407T1 (de) | 2006-04-19 | 2010-12-15 | Stepan Co | Strahlungshärtbare zusammensetzungen für verbesserte witterungsbeständigkeit |
JP2007305220A (ja) | 2006-05-11 | 2007-11-22 | Lintec Corp | 光記録媒体製造用シートおよび光記録媒体、ならびにそれらの製造方法 |
CN101117458A (zh) | 2006-08-01 | 2008-02-06 | 天津市振东涂料有限公司 | 一种紫外光或电子束引发的固化涂料 |
DE102006045041A1 (de) | 2006-09-25 | 2008-03-27 | Evonik Degussa Gmbh | Strahlenhärtbare Formulierung, die zu flexiblen Beschichtungen mit erhöhtem Korrosionsschutz auf Metalluntergründen führt |
US9725549B2 (en) * | 2006-10-27 | 2017-08-08 | Basf Se | Radiation-curable mixture containing low-molecular, ethylenically unsaturated compounds having non-aromatic ring systems |
KR101105116B1 (ko) * | 2006-12-14 | 2012-01-16 | 디에스엠 아이피 어셋츠 비.브이. | 광섬유에 대한 d1365 bj 선 경화성 1차 코팅 |
ATE503732T1 (de) * | 2006-12-14 | 2011-04-15 | Dsm Ip Assets Bv | Strahlungshärtbare d 1368 cr-grundierbeschichtung für optische fasern |
WO2008151286A1 (en) | 2007-06-05 | 2008-12-11 | The Glidden Company | Radiation curable coating composition derived from epoxidized vegetable oils |
US20090012202A1 (en) | 2007-07-03 | 2009-01-08 | Henkel Corporation | Acrylated Urethanes, Processes for Making the Same and Curable Compositions Including the Same |
US20090047531A1 (en) | 2007-08-17 | 2009-02-19 | Ppg Industries Ohio, Inc. | Packages having radiation-curable coatings |
JP2009102208A (ja) | 2007-10-25 | 2009-05-14 | Nof Corp | 防曇ガラス |
DE102007056477A1 (de) * | 2007-11-22 | 2009-05-28 | Kalle Gmbh | Druckfarbensystem zum Bedrucken von Nahrungsmittelhüllen auf Polyamidbasis, bedruckte Nahrungsmittelhüllen und Verfahren zu ihrer Herstellung |
KR100938430B1 (ko) | 2007-12-28 | 2010-01-22 | (주)디피아이 홀딩스 | 금속용 전자선 경화형 도료 조성물 및 이를 이용한 도막 형성 방법 |
US20090176907A1 (en) | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
DE102008021151A1 (de) * | 2008-04-28 | 2009-10-29 | Bayer Materialscience Ag | Blockfeste, strahlungshärtbare Beschichtungssysteme auf Basis hochmolekularer, wässriger Polyurethandispersionen |
WO2010055507A2 (en) | 2008-11-12 | 2010-05-20 | Pythagoras Solar Inc. | Concentrating photovoltaic module |
AU2012319183A1 (en) * | 2011-10-03 | 2014-05-22 | Biomimedica, Inc. | Polymeric adhesive for anchoring compliant materials to another surface |
-
2011
- 2011-12-23 US US13/976,763 patent/US9856392B2/en active Active
- 2011-12-23 BR BR112013015806-9A patent/BR112013015806B1/pt active IP Right Grant
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- 2011-12-23 KR KR20137017278A patent/KR20140007351A/ko not_active Application Discontinuation
- 2011-12-23 EP EP11802104.7A patent/EP2658893B2/en active Active
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-
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- 2013-06-19 ZA ZA2013/04519A patent/ZA201304519B/en unknown
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5128391A (en) * | 1988-02-24 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal containing organofunctional silane adhesion promoter |
EP1818349A1 (en) * | 2006-02-13 | 2007-08-15 | Cytec Surface Specialties, S.A. | Radiation curable compositions |
CN101096472A (zh) * | 2006-06-26 | 2008-01-02 | 上海飞凯光电材料有限公司 | 辐射固化材料粘接性能促进剂 |
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