CN1551894A - 基于不同程度烷氧基化多元醇的掺合物的可辐射固化的聚氨酯丙烯酸酯 - Google Patents
基于不同程度烷氧基化多元醇的掺合物的可辐射固化的聚氨酯丙烯酸酯 Download PDFInfo
- Publication number
- CN1551894A CN1551894A CNA02817447XA CN02817447A CN1551894A CN 1551894 A CN1551894 A CN 1551894A CN A02817447X A CNA02817447X A CN A02817447XA CN 02817447 A CN02817447 A CN 02817447A CN 1551894 A CN1551894 A CN 1551894A
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- China
- Prior art keywords
- urethane acrylate
- acid
- polyvalent alcohol
- alkoxylation
- mixture
- 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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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims description 27
- 229920005628 alkoxylated polyol Polymers 0.000 title description 7
- 230000005855 radiation Effects 0.000 title description 2
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 150000002148 esters Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 239000005056 polyisocyanate Substances 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 230000032050 esterification Effects 0.000 claims description 10
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 239000011111 cardboard Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003077 polyols Chemical group 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 17
- 238000009408 flooring Methods 0.000 abstract description 2
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- 239000003795 chemical substances by application Substances 0.000 description 25
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
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- -1 acrylic ester Chemical class 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000000976 ink Substances 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
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- 229940051250 hexylene glycol Drugs 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
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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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
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- C08F290/067—Polyurethanes; Polyureas
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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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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Abstract
本发明涉及新型低粘度且可辐射固化的聚氨酯丙烯酸酯，其固化后可以形成具有更好耐磨性的涂层，并且本发明还涉及其作为特别是用于地板材料的涂层成分的应用。
Description
本发明涉及一种低粘度并可辐射固化的新型聚氨酯丙烯酸酯，其可固化形成具有更好耐磨强度的涂层，并涉及其作为特别是用于地板材料涂层剂的用途。
基于(甲基)丙烯酸的羟基官能酯和二异氰酸酯的反应产物的可辐射硬化的涂料剂被称为聚氨酯丙烯酸酯，例如由P.K.T.Oldring(编著)，Chemistry & Technology of UV & EB FormulationsFor Coatings，Inks & Paints，Vol.2，1991，SITA Technology，伦敦，第73-123页中已知。它们常用于涂覆镶木地板和其他用作地板的材料。大部分这种涂层剂都具有通常大于10000mPa·s(在23℃时)的高动态粘度，因此可用低分子量的丙烯酸酯(活性稀释剂)稀释，并通过如使用辊筒等各种方法，和附加的光引发剂以及适用的话与添加剂一起施加于待涂底层后，再在紫外光照射下硬化。由于活性稀释剂的稀释，聚氨酯丙烯酸酯常常会损失一些重要性能，诸如耐磨强度和粘弹性。为此就要用特别低粘度的聚氨酯丙烯酸酯来保持低的活性稀释剂用量。在多数情况下，2-羟乙基-以及2-羟丙基丙烯酸酯或-甲基丙烯酸酯作为工业上易提供的初始产品和作为(甲基)丙烯酸的羟基官能酯，来生产聚氨酯丙烯酸酯。但是所制得的聚氨酯丙烯酸酯在未稀释时是很粘稠的(参见EP-A168173的实施例)。
EP-A53749公开了基于二异氰酸酯或多异氰酸酯、3到4.5重烷氧基化三羟甲基丙烷的羟基官能丙烯酸酯以及任选地羟烷基丙烯酸酯的低粘度聚氨酯丙烯酸酯的制备过程。在所引用的中请中，对比实验显示，即使乙氧基化程度达到了7，相应产品的耐受极性溶剂的稳定性还是不够的。
本发明的目的在于提供可耐受溶剂且与已有技术相比具有更好耐磨强度的低粘度聚氨酯丙烯酸酯。
现已发现，基于二异氰酸酯或多异氰酸酯以及高度和低度烷氧基化多元醇混合物的羟基官能(甲基)丙烯酸酯的聚氨酯丙烯酸酯，具有低粘度、能耐受溶剂且尤其是耐磨。这是很令人惊奇的发现，因为没有预料到在含有例如七重乙氧基化三元醇的聚氨酯丙烯酸酯和含有平均相应于七重乙氧基化三元醇的高乙氧基化和低乙氧基化的混合物的聚氨酯丙烯酸酯之间会有着本质差异。
因此，本发明内容在于，提供可通过二异氰酸酯和/或多异氰酸酯与基于具有三个或更多羟基的不同烷氧基化程度的多元醇的混合物的丙烯酸和/或甲基丙烯酸的羟基官能偏酯进行反应而制得的低粘度、可辐射固化的聚氨酯丙烯酸酯，且其特征在于，烷氧基化的多元醇混合物由25到75mol％的烷氧基化度在3到5之间的多元醇和75到25mol％的烷氧基化度在8到25之间的多元醇组成。
本发明内容还在于提供一种生产本发明的聚氨酯丙烯酸酯的两步生产法，其特征在于在第一步中烷氧基化多元醇用丙烯酸和/或甲基丙烯酸[以下记作(甲基)丙烯酸]进行部分酯化，然后在第二步中与二异氰酸酯或多异氰酸酯进行反应。
本发明内容还在于聚氨酯丙烯酸酯作为在高能辐射影响下固化的涂层剂的成分的用途。
使用分子量为92-254的三元和多元醇如丙三醇、三羟甲基丙烷、季戊四醇、二三羟甲基丙烷、二季戊四醇或山梨醇及其混合物作为烷氧基化多元醇的基础。优选为丙三醇和三羟甲基丙烷。烷氧基化反应按照本身已公知的生产聚醚的方法来进行。为此可以使用环氧乙烷、环氧丙烷和四氢呋喃，优选环氧乙烷和/或环氧丙烷作为单体，其中还可以使用混合物或连续的不同单体(“嵌段”的制备)。将以醇的量计的烷氧基化单体的量记作烷氧基化度(例如每mol的三羟甲基丙烷7.0mol的环氧乙烷就对应烷氧基化度为7.0)。
关键在于使用两种不同烷氧基化程度的多元醇。一方面使用25-75mol％，优选30-45mol％的烷氧基化度在3和5之间的多元醇，另一方面要使用补足100mol％份数的，也就是75到25mol％，优选70到55mol％的多元醇，且它具有的烷氧基化度要在8到25之间，优选是8到15之间，特别优选是10到13之间。
烷氧基化多元醇的混合物利用(甲基)丙烯酸根据本身已公知的方法进行酯化，而优选所采用的方法是，其中反应水能通过和水形成共沸混合物的溶剂(共沸夹带剂)而蒸馏除去。也可以分别酯化不同的烷氧基化的多元醇，接着和/或在进一步与多异氰酸酯反应前混合这些酯。如果适当的话，还可以进一步在酯化反应之后，使剩余量的酸和环氧化合物进行反应。这些方法记载在诸如EP-A54105，EP-A126341和EP-A900778中。
丙烯酸和/或甲基丙烯酸的用量为，以烷氧基化多元醇的羟基基团计，酸对氢氧化物的当量比为1比1.1到1比2.4，优选1比1.2到1比1.8，特别优选1比1.3到1比1.5。只要是可供使用，也可以使用它们的酐或低聚反应产物，如甲基丙烯酸酐或二聚丙烯酸来代替纯酸。
作为共沸夹带剂使用的有烃类和它们的卤代或硝基取代产物，以及其他一些既不与反应物反应也不会因酸催化剂影响而变化的溶剂。优选使用未取代的烃类。比如有：脂肪烃如己烷、庚烷、辛烷、不同沸点范围的汽油馏分，脂环烃如环戊烷、环己烷、甲基环己烷，或者芳烃如苯、甲苯或同分异构的二甲苯。优选使用沸点在70℃-120℃之间的那些溶剂。这里特别优选是环己烷、甲苯或者在70℃-120℃之间沸腾的汽油馏分。与水不混溶的溶剂也可以是上述物质的混合物。以待酯化的反应成分的重量计，溶剂用量在10-100重量％之间，优选在15-50重量％之间，特别优选在20-40重量％之间。
作为酸性酯化反应催化剂使用的可以是无机酸也可以是有机酸，其用量以待酯化的反应成分的重量计，在0.1-3.0重量％之间，优选在0.5-1.5重量％之间。这些酯化催化剂的实例为硫酸、磷酸、焦磷酸、对甲苯磺酸、苯乙烯-二乙烯基苯磺酸、氯磺酸、氯甲酸，其中优选硫酸和对甲苯磺酸。另外此处还可以使用连接于固体树脂之上的酸催化剂，比如离子交换剂。
反应可以在有一种或多种阻聚剂存在的情况下进行，阻聚剂的量为0.01-1重量％，优选为0.1-0.5重量％，以待酯化的混合物计。这种抑制剂在比如Houben-Weyl，Methoden der organischen Chemie，第四版，XIV/1卷，Georg Thieme出版社，斯图加特，1961，参见第433页中有记述。作为实例有：连二亚硫酸钠，氢硫化钠，硫磺，肼，苯肼，二苯肼，N-苯基-β-萘胺，N-苯基乙醇二胺，二硝基苯，苦味酸，对亚硝基二甲基苯胺，二苯基亚硝胺，酚类如对叔丁基邻苯二酚，2，5-二-叔戊基对苯二酚，硝酰化合物，对烷氧基苯酚，二叔丁基对苯二酚，二硫化四甲基秋兰姆，2-巯基苯并噻唑和二甲基二硫代氨基甲酸钠盐。另外，在一优选方案中是将含氧气体，优选空气导入含有溶剂的反应混合物中。
(甲基)丙烯酸的酯化首先在温度为60℃-140℃的范围内进行，优选在70℃-120℃，特别优选在所使用溶剂的沸点值。通过蒸馏，溶剂不断从反应混合物中去除，然后在反应器外的脱水器中浓缩，并从夹带水中分离，之后再返入反应混合物中去。当反应中脱去的水量与理想的反应度相符或反应混合物的酸值降到与理想反应度相符的数值时，反应结束。此时酸值为0.1到15，优选为1到5mg氢氧化钾每克反应混合物。接着，可任选地对酯化反应催化剂进行中和、沉淀和/或滤除，任选地还可以将溶剂蒸馏除去，而残留的酸可以与任选地带有不饱和基团的环氧化合物进行反应。在一个优选的变化方案中，向每摩尔的残留酸加入0.8到1.5、优选0.9到1.1mol的甲基丙烯酸缩水甘油酯，之后在70到130、优选80到110℃下反应，直至酸值低于3、优选低于1mg氢氧化钾每克反应混合物时止。
如果溶剂在与环氧化合物反应之前没有馏出，那么就需要在反应后将其去除。这里，优选蒸馏在低压下进行，直到样品的闪点在100℃以上。
在一同样是原理已公知的变化方案中，也可以用酯交换反应工艺来代替酸和多元醇的酯化反应。上述方法的原理记载在诸如DE-A4019788中。这里，可以使用(甲基)丙烯酸与低分子量的醇例如甲醇或乙醇所形成的酯来代替(甲基)丙烯酸。此时就不会有水分解出来了，而是要将低分子量的醇经蒸馏从反应混合物中去除。该方法中可以省略掉共沸的夹带剂。
由不同烷氧基化的多元醇和(甲基)丙烯酸所形成的羟基官能偏酯通常在23℃时具有1000mPa·s以下的动态粘度，并且它是透明的、水亮的或是轻微带色的。在第二步中，使这些产品与二异氰酸酯和/或多异氰酸酯——下文称多异氰酸酯——进行反应。
除由不同烷氧基化的多元醇和(甲基)丙烯酸所制得的羟基官能偏酯外，适当的话还可以使用与异氰酸酯有反应活性的其他化合物。对于本发明的聚氨酯丙烯酸酯来说，其用量是有限制的：即每异氰酸酯当量使用低于0.4当量、优选低于0.2当量的与异氰酸酯有反应活性的其他化合物。
这一类化合物可以是：带有一个游离羟基的、丙烯酸或甲基丙烯酸与二元醇的酯，如2-羟乙基-、2-或3-羟丙基或2-、3-或4-羟丁基-(甲基)丙烯酸酯，以及它们和有如ε-己内酯的内酯的反应产物，或者是这类化合物的任意混合物，即分子量范围在62到286的(环)链烷二醇(即羟基和环(脂)族烃相连的二元醇)，如乙二醇，1，2-和1，3-丙二醇，1，2-，1，3-和1，4-丁二醇，1，5-戊二醇，1，6-己二醇，新戊二醇，环己烷-1，4-二甲醇，1，2-和1，4-环己二醇，2-乙基-2-丁基丙二醇，2-二乙基-1，3-丙二醇，2，2-二甲基-1，3-丙二醇，2-乙基-1，3-己二醇，2，5-二甲基-1，6-己二醇，2，2，4-三甲基-1，3-戊二醇，(3-羟基-2，2-二甲基丙基)-3-羟基-2，2-二甲基丙酸酯，含有醚氧的且最大分子量约为2000、优选约1000以及特别优选约500的二醇，如二甘醇，三甘醇，四甘醇，双丙甘醇，三丙二醇，聚乙二醇，聚丙二醇或聚丁二醇。上述二醇和ε-己内酯或其他己内酯的反应产物，同样也可以作为二醇来使用。此外，也可以使用一些本身已公知的由前述的二醇和芳族和/或优选地由环(脂)族二羧酸或其酸酐(如邻苯二甲酸，邻苯二甲酸酐，间苯二甲酸，四氢邻苯二甲酸，四氢邻苯二甲酸酐，六氢邻苯二甲酸，六氢邻苯二甲酸酐，环己烷二羧酸，马来酸酐，富马酸，丙二酸，琥珀酸，琥珀酸酐，戊二酸，己二酸、庚二酸，辛二酸，癸二酸，十二烷二酸，和氢化的二聚脂肪酸)得到的聚酯二醇。
但特别优选的是放弃使用上述能进一步和异氰酸酯进行反应的化合物。
合适的多异氰酸酯是本身在聚氨酯化学中已公知的、带有以脂族、环脂族和/或芳族方式相连的异氰酸酯基团的任意的有机多异氰酸酯，其优选具有144到1000，更优选168到300的分子量。适合的例子有亚丁基二异氰酸酯，1，6-己二异氰酸酯(HDI)，异氟尔酮二异氰酸酯(IPDI)，3(4)-异氰酸基甲基-甲基环己基-异氰酸酯(IMCI)，三甲基六亚甲基二异氰酸酯(＝2，2，4和/或2，4，4-三甲基六亚甲基二异氰酸酯)，异构的二(4，4’-异氰酸基环己基)甲烷(H12MDI)，异构的二(异氰酸基甲基)-甲基环己烷，异氰酸基甲基-1，8-辛二异氰酸酯，1，4-亚环己基二异氰酸酯，1，4-苯二异氰酸酯，2，4-和/或2，6-甲苯二异氰酸酯(TDI)，1，5-萘二异氰酸酯，2，4’-和/或4，4’-二苯基甲烷二异氰酸酯(MDI)，三苯基甲烷-4，4’，4”-三异氰酸酯或其与尿烷-、异氰尿酸酯-、脲基甲酸酯-、缩二脲-、脲二酮(Uretdion)-，亚氨基噁二嗪二酮(Iminooxadiazindion)结构和/或其混合物以及脂族和芳族的二-和/或多异氰酸酯混合物生成的衍生物。一般而言，这些衍生物具有最多约1000的平均分子量。这类衍生物的生产制备方法记载在如US-A3124605，US-A3183112，US-A3919218，US-A4324879或EP-A798299的文献中。
优选使用HDI、IPDI、TDI、H12MDI和/或通过HDI、TDI或IPDI的三聚而得到的具有异氰酸酯基团的多异氰酸酯。特别优选的是HDI和IPDI及其混合物。
使用多异氰酸酯时，异氰酸酯基团对羟基基团的当量比为1比1到1比3，优选1比1到1比2，特别优选1比1到1比1.5。而转化度通常通过追踪反应混合物中异氰酸酯含量来得到监控。为此可以对所提取的样品进行光谱测量(红外或近红外光谱)或是化学分析(滴定)。优选将反应进行至异氰酸酯含量为0.2％或更低时止。反应温度要保持在20到100℃，特别优选50到80℃。在反应进行时可以以任意的次序将起始成分加到反应中去。反应优选是在有适于尿烷化反应的合适的催化剂存在的条件下进行，这种催化剂有如辛酸锌(II)，二丁基月桂酸锌或叔胺如二氮杂二环辛烷。
这样制得的聚氨酯丙烯酸酯可以有益地用作涂层剂的主成分。这种涂层剂又可以含有辅料和助剂，比如本身已公知的，且可以在用足够能量射线，如UV射线照射后引发自由基聚合反应的引发剂。这种光引发剂记载在比如P.K.T.Oldring(编著)，用于涂层、油墨和涂料中的UV和EB制剂化学和技术，第3册，1991，SITA技术，伦敦，(第61-325页)中。而具体实例是1-羟基环己基苯酮，偶苯酰缩酮如偶苯酰二甲基缩酮，酰基氧化膦如二(2，4，6-三甲基苯甲酰)苯基氧化膦、二乙酰氧化膦，苯甲酮和它们的衍生物。它们可以单独或是混合使用，适用时还可以和别的作为添加剂的促进剂或助引发剂一起使用，其用量以涂料体系中的固体计为0.1到10重量份，优选2到7重量份，特别优选3到4重量份。光聚合反应也可以在惰性气氛中进行，这时光引发剂可以选择明显小于空气中进行硬化时的用量。如果该涂层剂借助电子束进行硬化，则就可以舍弃光引发剂。
涂层剂可以和作为能在UV固化时(共)聚合的助剂的稀释剂进行混合。这种反应性稀释剂记载在P.K.T.Oldring(编辑)，用于涂层、油墨和涂料中的UV和EB制剂化学和技术，第2册，1991，SITA技术，伦敦，第237-285页中。具体实例有丙烯酸或甲基丙烯酸、优选丙烯酸与下列醇的酯。一元醇有各种异构的丁醇、戊醇、己醇、庚醇、辛醇、壬醇和癸醇，此外还有环脂族的醇如异冰片、环己醇和烷基化的环己醇，二环戊醇，芳基脂族醇如苯氧乙醇和壬基苯乙醇，以及四氢呋喃甲醇。另外可使用这些醇的烷氧基化衍生物。二元醇有，比如，乙二醇、丙二醇-1，2，丙二醇-1，3，二甘醇，双丙甘醇，各种异构的丁二醇，新戊二醇，己二醇-1，6，2-乙基己二醇和三丙二醇或也可以是这些醇的烷氧基化衍生物。优选的二元醇是己二醇-1，6，双丙甘醇和三丙二醇。三元醇有甘油或三羟甲基丙烷或其烷氧基化衍生物。优选丙氧基化的甘油。由于本发明的聚氨酯丙烯酸酯相对具有较低的粘度，因此较之现有技术的聚氨酯丙烯酸酯，为了调节到相同的粘度，通常需要较少的活性稀释剂。
此外，也可以将根据本发明所制得的涂层剂与不同种类的助剂和添加剂(辅料)共混。这里可添加的有填料，颜料，染料，平滑剂，褪光剂，排气剂(Entlüftungsmittel)如聚丙烯酸酯，粘结剂如氨基烷基三烷氧基硅烷和流动控制剂如聚硅氧烷，而上述这些助剂都要以涂层技术中熟知的常用量来进行使用。为了改善耐候性，如耐光照，可以以常用量来使用防光致老化剂，如UV-吸收剂和位阻胺。如果使用UV-吸收剂，就必须通常使用一定比例的长波吸收型光引发剂。防光致老化剂的使用方法及其各种不同的类型都记载在诸如A.Valet，Lichtschutzmittel für Lacke，Vincentz出版社，汉诺威，1996中。也可以使用对于自由基聚合为惰性的溶剂，然后将该溶剂在涂覆和固化过程之间，任选地利用导入热量而除去。
含有本发明聚氨酯丙烯酸酯的涂层剂适用于生产在各种基材之上的高级涂层、覆膜和涂漆，这些基材可以是例如纸张、纸板、皮革、织物、玻璃、塑料、如必要时经受过预处理的铝片或钢片等的金属，也可以是所谓“箔”形的金属，木材特别是镶木地板或木质材料如中密度的纤维板，塑料材料如聚碳酸酯或聚氯乙烯薄板(PVC)，无机材料如水泥、陶土、矿石、陶瓷或者是由所述材料构成的且已涂覆过的基材，如汽车或汽车部件。也可以对那些由多种所述材料构成的基材进行涂覆。本发明的涂层剂特别适用于可做地板用的材料的耐磨涂层。特别是镶木地板和PVC薄板。
可以利用涂漆技术中常用且熟知的方法来将涂层剂涂覆于待涂覆的材料之上，这些方法有如喷涂、刮涂、辊涂、浇注、浸渍、离心涂覆和喷雾(真空)。液态涂层剂的固化过程通过紫外线或电子束的辐照来完成。为此，要将被涂覆的材料置于比如汞的中压辐射器下。利用UV射线进行的固化过程以公知的方法进行，且相关内容记载在比如P.K.T.Oldring(编辑)，用于涂层、油墨和涂料中的UV和EB制剂化学和技术，第1册，1991，SITA技术，伦敦，第167-269页中。
实施例
由烷氧基化的多元醇和丙烯酸制备偏酯：
A)在贯通导入空气(每小时一倍的装置体积)和导入氮气(每
小时两倍装置体积)的情况下，称量860.6g平均12重乙氧
基化且起始于三羟甲基丙烷的聚醚(羟基数255，23℃时动态
粘度265mPa·s)，214.2g平均4重乙氧基化且起始于三羟甲
基丙烷的聚醚(羟基数550，23℃时动态粘度505mPa·s)，
309.6g丙烯酸，9.3g的4-甲苯磺酸，3.9g的4-甲氧基苯
酚，0.3g的2，5-二叔丁基对苯二酚和560.1g的异辛烷，将
它们加入到带有水分离器、搅拌器、气体导管和温度计的装
置中。然后一边搅拌一边将反应混合物加热到回流温度(约
94-108℃)并保持强烈回流，直至酸值达到小于4.5的数
值。在这期间，约有77g的水量被分离。接着将物料冷却到
50℃，并在50℃下缓慢抽真空，将溶剂蒸馏除去，直至在90
℃和真空(＜50mbar)下不再有溶剂被蒸除。在经过通风换气
后，一边搅拌一边均匀添加26.3g甲基丙烯酸缩水甘油酯。
然后在100℃下继续搅拌一小时，产品的酸值低于2，而羟基
数在80和90之间。
B)重复试验A)，区别在于用214.2g的平均3重丙氧基化且起始
于三羟甲基丙烷的聚醚(羟基数550，23℃下的动态粘度为
1800mPa·s)代替平均4重乙氧基化的起始于三羟甲基丙烷
的聚醚。
聚氨酯丙烯酸酯
根据下表，在贯通导入空气(每小时一倍的装置体积)和导入氮气(每小时两倍装置体积)的情况下，将由烷氧基化的多元醇和丙烯酸形成的偏酯，以及以总物料量计的0.1重量％的2，6-二叔丁基-4-甲基苯酚和以总物料量计的0.05重量％的乙基己酸锡(II)称量好加入到带有搅拌器、气体导管和温度计的装置中，并一边搅拌一边加热到55℃。然后滴加相应的异氰酸酯，使得利用放热反应而将温度保持在55到60℃。滴加完成后(约1h)，将温度调整到60℃并保持其直到NCO含量低于0.1％(约8h)。
| 聚氨酯丙烯酸酯的生产 | 对涂漆的测试 | ||||
| 实施例号 | 偏酯 | 异氰酸酯 | 粘度[23℃] | 耐磨性 | 稳定性 |
| 1 | A[450.9g] | TDI[25.0g]和HDI[24.2g]的混合物 | 2600mPas | 7900周期每100μm厚涂层 | 1(NaOH)/2(乙醇) |
| 2 | B[430.0g] | IPDI[62.0g] | 4300mPas | 5600 | 1/3 |
| 3 | A[450.9g] | 首先HDI[24.2g]，然后TDI[25.0g] | 3100mPas | 10100 | 1/2 |
| 4 | A[444.1g] | IPDI[56.0g] | 8000mPas | 7300 | 1/2 |
| 5 | A[450.0g] | TDI[50.0g] | 5600mPas | 7000 | 1/2 |
| 对比：EP-A53749的重校实施例6 | 4000 | 1/2 | |||
| 对比：EP-A53749的重校实施例3 | 4300 | 1/2 | |||
TDI-Desmodur T80，Bayer AG，Leverkusen，DE；HDI-DesmodurH，Bayer AG，Leverkusen，DE；IPDI-DesmodurI，Bayer AG，Leverkusen.DE.
将85重量份的聚氨酯丙烯酸酯分别与16重量份双丙甘醇二丙烯酸酯(BASF AG，Ludwigshafen，DE)和2.5重量份光引发剂Darocur1173，Ciba特种化学，Lampertheim，DE，借助螺旋刮刀施加于被腐蚀的中密度纤维板(MDF)上，并利用UV光(带式排列，1辐射器，80W/cm灯照波长[CK-辐射器，IST，Metzingen，DE])进行固化。为进行耐磨性测试，按如下方法制备涂膜：一次用手工涂胶机#2[约18μm]，以15m/min的带速通过2次，然后二次用手工涂胶机#3[约30μm]且以5m/min的带速通过1次。所得到的涂层厚度通过光学显微镜确定。为进行稳定性测试，借助于螺旋刮刀在MDF上生产约120μm的涂膜，并在5m/min的带速下通过一次进行固化。
进行耐磨测试时，使用的是Erichsen公司的5130型TaberAbraser和155型Taber Abraser Grip Feeder，并且使用TreibacherSchleifmittel公司(Villach，Austria)的氧化铝(AlodurEPL)平滑剂，该氧化铝经过筛选(200μm筛目)和干燥(80℃，1小时)。耐磨测试根据Erichsen公司的测试条件指南BA 155/D-VI/1995，在1000g负载每轴，散逸量85(对应于34g每100转)的条件下进行。利用丙烯酸片进行校准。在2000转时发现耐磨量为142mg(理想值为127±18mg)。在每种情况下测定周期数，直至涂层毁损为止。算上所测得的层厚度，就能得到每100μm厚的层所给定的周期数。
稳定性测试利用48％的含水乙醇和16％的氢氧化钠进行。各将浸渍过的棉纱团覆盖在涂层上16h。接着用一块干燥且柔软的织物将表面擦拭干净，并进行视觉检查。所得结果以分值(0-无变化直至5-毁坏)进行评价。
Claims (8)
1.低粘度的、可辐射固化的聚氨酯丙烯酸酯，其可以通过使二异氰酸酯和/或多异氰酸酯与基于不同烷氧基化程度且带有三个或多个羟基基团的多元醇的混合物的丙烯酸和/或甲基丙烯酸的羟基官能偏酯反应而得到，其特征在于烷氧基化的多元醇的混合物由25到75mol％的烷氧基化度在3到5之间的多元醇和75到25mol％的烷氧基化度在8到25之间的多元醇组成。
2.根据权利要求1的聚氨酯丙烯酸酯，其特征在于它们不含有丙烯酸羟基-C1-4-烷基酯和甲基丙烯酸羟基-C1-4-烷基酯。
3.根据权利要求1的聚氨酯丙烯酸酯，其特征在于烷氧基化的多元醇的混合物由30到45mol％的烷氧基化度在3到5之间的多元醇和70到55mol％的烷氧基化度在8到15之间的多元醇组成。
4.根据权利要求1的聚氨酯丙烯酸酯，其特征在于使用了脂族和芳族二异氰酸酯和/或多异氰酸酯的混合物。
5.生产如权利要求1的低粘度且可辐射固化的聚氨酯丙烯酸酯的方法，其特征在于在第一阶段中，烷氧基化的多元醇部分地用丙烯酸和/或甲基丙烯酸[以下记作(甲基)丙烯酸]进行酯化；且在第二阶段中，使其与二异氰酸酯和/或多异氰酸酯进行反应。
6.聚氨酯丙烯酸酯作为能在高能辐照影响下固化的涂层剂成分的用途。
7.根据权利要求1的聚氨酯丙烯酸酯在涂覆纸张、纸板、皮革、织物、玻璃、金属和塑料方面的应用。
8.根据权利要求1的聚氨酯丙烯酸酯在涂覆地板、木板、PVC板和由木材与塑料制成的镶木地板方面的应用。
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| DE10143630A DE10143630A1 (de) | 2001-09-06 | 2001-09-06 | Strahlenhärtende Beschichtungsmittel |
| DE10143630.0 | 2001-09-06 |
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| EP (1) | EP1456273B1 (zh) |
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| AT (1) | ATE493455T1 (zh) |
| BR (1) | BR0212331B1 (zh) |
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| DE (2) | DE10143630A1 (zh) |
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| CN111655805A (zh) * | 2018-01-23 | 2020-09-11 | 斯蒂潘公司 | 用于低voc聚氨酯应用的多元醇 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108431066A (zh) * | 2015-12-22 | 2018-08-21 | 湛新荷兰有限公司 | 具有残留异氰酸酯基的可辐射固化的氨酯(甲基)丙烯酸酯 |
| CN111655805A (zh) * | 2018-01-23 | 2020-09-11 | 斯蒂潘公司 | 用于低voc聚氨酯应用的多元醇 |
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| Publication number | Publication date |
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| EP1456273A1 (de) | 2004-09-15 |
| TWI238179B (en) | 2005-08-21 |
| KR20040033020A (ko) | 2004-04-17 |
| BR0212331B1 (pt) | 2012-12-25 |
| PL368501A1 (en) | 2005-04-04 |
| KR100897985B1 (ko) | 2009-05-18 |
| CA2459358C (en) | 2010-11-02 |
| MXPA04002119A (es) | 2004-09-08 |
| PT1456273E (pt) | 2011-02-25 |
| JP2005502749A (ja) | 2005-01-27 |
| HUP0402239A3 (en) | 2008-06-30 |
| US6753394B2 (en) | 2004-06-22 |
| MX246814B (es) | 2007-06-29 |
| WO2003022902A1 (de) | 2003-03-20 |
| CA2459358A1 (en) | 2003-03-20 |
| JP4253584B2 (ja) | 2009-04-15 |
| HK1071763A1 (en) | 2005-07-29 |
| PL207569B1 (pl) | 2011-01-31 |
| DE50214841D1 (de) | 2011-02-10 |
| EP1456273B1 (de) | 2010-12-29 |
| ATE493455T1 (de) | 2011-01-15 |
| DE10143630A1 (de) | 2003-03-27 |
| BR0212331A (pt) | 2004-09-21 |
| HU228390B1 (en) | 2013-03-28 |
| ES2356731T3 (es) | 2011-04-12 |
| CN1258548C (zh) | 2006-06-07 |
| DK1456273T3 (da) | 2011-04-18 |
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| US20030050390A1 (en) | 2003-03-13 |
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