JP2012197268A - β-HYDROXYALKYLAMIDE AND CROSSLINKABLE COMPOSITION - Google Patents
β-HYDROXYALKYLAMIDE AND CROSSLINKABLE COMPOSITION Download PDFInfo
- Publication number
- JP2012197268A JP2012197268A JP2012046835A JP2012046835A JP2012197268A JP 2012197268 A JP2012197268 A JP 2012197268A JP 2012046835 A JP2012046835 A JP 2012046835A JP 2012046835 A JP2012046835 A JP 2012046835A JP 2012197268 A JP2012197268 A JP 2012197268A
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- Japan
- Prior art keywords
- acid
- group
- hydroxyalkylamide
- parts
- hydrocarbon group
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
- 229920005989 resin Polymers 0.000 claims description 43
- 239000011347 resin Substances 0.000 claims description 43
- 125000001931 aliphatic group Chemical group 0.000 claims description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- -1 alicyclic hydrocarbon Chemical class 0.000 abstract description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 20
- 239000003431 cross linking reagent Substances 0.000 abstract description 10
- 239000011342 resin composition Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 87
- 238000005259 measurement Methods 0.000 description 38
- 238000010992 reflux Methods 0.000 description 38
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- 239000007789 gas Substances 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 238000007664 blowing Methods 0.000 description 19
- 238000001723 curing Methods 0.000 description 18
- 150000002430 hydrocarbons Chemical group 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 7
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000013112 stability test Methods 0.000 description 5
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
- 229940043276 diisopropanolamine Drugs 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
本発明は、有機溶剤可溶なβ−ヒドロキシアルキルアミドに関する。更には、β−ヒドロキシアルキルアミドを有する硬化剤、その製造方法、β−ヒドロキシアルキルアミドとカルボキシ基を有する樹脂との組成物、およびその組成物を加熱することでなる硬化物に関する。 The present invention relates to an organic solvent-soluble β-hydroxyalkylamide. Further, the present invention relates to a curing agent having β-hydroxyalkylamide, a production method thereof, a composition of β-hydroxyalkylamide and a resin having a carboxy group, and a cured product obtained by heating the composition.
架橋剤を用いて樹脂組成物を硬化させることで、樹脂の耐熱性、機械特性、密着性、耐湿性、耐薬品性などを向上させることは様々な用途で幅広く用いられている。 It is widely used in various applications to improve the heat resistance, mechanical properties, adhesion, moisture resistance, chemical resistance, etc. of a resin by curing the resin composition using a crosslinking agent.
樹脂としてカルボキシ基を有する樹脂を使用する場合は、カルボキシ基と反応しうる官能基を有する架橋剤が用いられる。その官能基は、たとえば、イソシアネート基、ブロックイソシアネート基、エポキシ基、β−ヒドロキシアルキルアミド基、などが挙げられる。 When using resin which has a carboxy group as resin, the crosslinking agent which has a functional group which can react with a carboxy group is used. Examples of the functional group include an isocyanate group, a blocked isocyanate group, an epoxy group, and a β-hydroxyalkylamide group.
イソシアネート基を有する架橋剤を使用した場合、イソシアネート基とカルボキシ基は130℃以上で反応すると言われている。しかし、イソシアネート基は樹脂中のOH基や水、アルコールとの反応性がより高いため、配合時に溶剤にアルコールを使用する場合や、水が含まれる溶剤を使用する場合には、カルボキシ基と反応する前に水やアルコールと反応してしまうため使用できない。また、配合後の長期間保存も空気中の水分と反応してしまうため、1液化するのは困難である。 When a crosslinking agent having an isocyanate group is used, the isocyanate group and the carboxy group are said to react at 130 ° C. or higher. However, since isocyanate groups are more reactive with OH groups, water, and alcohol in the resin, they react with carboxy groups when alcohol is used as a solvent during mixing or when a solvent containing water is used. It cannot be used because it reacts with water and alcohol before it is used. In addition, since long-term storage after blending also reacts with moisture in the air, it is difficult to make a single solution.
上記の問題を解決するためにブロックイソシアネートを使用する例もあるが、ブロック化剤が硬化物に残存することで物性に悪影響を与えることがある。また、ブロック化剤によっては加熱硬化時にブロック化剤が空気中に飛散し、作業者あるいは環境に悪影響を与える懸念がある。ブロック化剤が外れて硬化する温度よりも沸点が高いアルコール系の溶剤を使用する場合も、樹脂に含まれるカルボキシ基よりも先にアルコール系溶剤と反応してしまうため、このような溶剤は使用できない。 There is an example in which a blocked isocyanate is used to solve the above problem, but the blocking agent remains in the cured product, which may adversely affect the physical properties. Further, depending on the blocking agent, there is a concern that the blocking agent is scattered in the air at the time of heat curing, which adversely affects the operator or the environment. Even when using an alcoholic solvent with a boiling point higher than the temperature at which the blocking agent comes off and hardens, it reacts with the alcoholic solvent prior to the carboxy group contained in the resin. Can not.
また、エポキシ基を有する架橋剤はイソシアネートと並んでカルボキシ基を有する樹脂を架橋するときに汎用的に用いられており、多くの種類が市販されている。エポキシ基とカルボキシ基の反応では副生成物が存在せず、ブロックイソシアネートのブロック化剤のような悪影響は起こさないと考えられる。無触媒ではあまり反応が進まないが、3級アミンや4級アンモニウム塩などを触媒として添加することで、150℃以下の温度で硬化させることが可能である。しかし、添加する触媒の影響で室温でも反応が少しずつ進行してしまい、保存安定性が悪いという問題がある。 Moreover, the crosslinking agent which has an epoxy group is used universally when bridge | crosslinking the resin which has a carboxy group along with isocyanate, and many kinds are marketed. There is no by-product in the reaction of the epoxy group and the carboxy group, and it is considered that no adverse effect such as a blocking agent for blocked isocyanate occurs. The reaction does not proceed so much without a catalyst, but it can be cured at a temperature of 150 ° C. or lower by adding a tertiary amine or a quaternary ammonium salt as a catalyst. However, there is a problem that the reaction proceeds little by little at room temperature due to the influence of the catalyst to be added, and the storage stability is poor.
β−ヒドロキシアルキルアミドもカルボキシ基と反応する架橋剤である(特許文献1)。反応時の副生成物は水のみであり、硬化物に与える影響も少なく、作業者や環境にはまったく影響がないメリットがある。また、150℃で硬化させることが可能である。現在市販されているβ−ヒドロキシアルキルアミドとして、エムスケミー社のPrimid XL−552などが挙げられ、主に粉体塗料の架橋剤として用いられている(特許文献2)。 β-hydroxyalkylamide is also a crosslinking agent that reacts with a carboxy group (Patent Document 1). The only by-product during the reaction is water, and there is little effect on the cured product, and there is a merit that there is no effect on the worker or the environment. Further, it can be cured at 150 ° C. Currently available commercially available β-hydroxyalkylamides include Primid XL-552 manufactured by Ems Chemie, and are mainly used as a crosslinking agent for powder coatings (Patent Document 2).
しかし、市販されているβ−ヒドロキシアルキルアミドは非常に溶解性が悪く、液体塗料として用いられている例は少ない。多数のヒドロキシ基を有する化合物、結晶性が高さと極性の高さが溶解性を悪化させていると考えられる。ヒドロキシ基が多いため、水性塗料への応用例は一部みられる(特許文献3)が、溶剤系の塗料に応用されている例は見られない。溶解性が悪く均一に混合できていない塗料では膜物性の一部が低下、または、その物性が安定しないといった問題が発生する。 However, commercially available β-hydroxyalkylamides have very poor solubility and are rarely used as liquid paints. A compound having a large number of hydroxy groups, high crystallinity and high polarity are considered to deteriorate the solubility. Since there are many hydroxy groups, some examples of application to water-based paints are seen (Patent Document 3), but no examples of application to solvent-based paints are found. If the paint has poor solubility and cannot be mixed uniformly, there is a problem that a part of the film physical properties are lowered or the physical properties are not stable.
本発明は上記の現状に鑑みてなされたものであり、有機溶剤に可溶であり、カルボキシ基と反応する架橋剤であるβ−ヒドロキシアルキルアミドを提供することを目的とする。さらには、有機溶剤可溶なβ−ヒドロキシアルキルアミドを含む樹脂組成物、その硬化物、有機溶剤可溶なβ−ヒドロキシアルキルアミドの製造方法を提供することを目的とする。 The present invention has been made in view of the above situation, and an object thereof is to provide β-hydroxyalkylamide which is a crosslinking agent that is soluble in an organic solvent and reacts with a carboxy group. It is another object of the present invention to provide a resin composition containing an organic solvent-soluble β-hydroxyalkylamide, a cured product thereof, and a method for producing an organic solvent-soluble β-hydroxyalkylamide.
すなわち本発明は、一般式(1)で表されることを特徴とする(B)β−ヒドロキシアルキルアミドに関する。
一般式(1)
Xは炭素、水素、酸素、窒素、硫黄、または、ハロゲンから構成されるn価の基であり、
脂環式炭化水素基、分岐脂肪族炭化水素基、芳香族炭化水素基、酸素、窒素、もしくは、硫黄で分断されている直鎖脂肪族炭化水素基、または、酸素、窒素、硫黄、もしくは、ハロゲンを含む置換基で置換された直鎖脂肪族炭化水素基であり、
X中のカルボニル基に直接結合する原子が炭素原子である。
nは2〜6の整数であり、
R1およびR2は、それぞれ独立に、水素原子、一般式(2)で表される基、または炭化水素基を表し、R1およびR2のうち、少なくとも1つは、一般式(2)で表される基である。
一般式(2)
General formula (1)
X is an n-valent group composed of carbon, hydrogen, oxygen, nitrogen, sulfur, or halogen;
An alicyclic hydrocarbon group, a branched aliphatic hydrocarbon group, an aromatic hydrocarbon group, a linear aliphatic hydrocarbon group separated by oxygen, nitrogen, or sulfur, or oxygen, nitrogen, sulfur, or A linear aliphatic hydrocarbon group substituted with a halogen-containing substituent,
The atom directly bonded to the carbonyl group in X is a carbon atom.
n is an integer of 2-6,
R 1 and R 2 each independently represent a hydrogen atom, a group represented by the general formula (2), or a hydrocarbon group, and at least one of R 1 and R 2 is represented by the general formula (2) It is group represented by these.
General formula (2)
また本発明は、X中のカルボニル基に直接結合する原子が、芳香環を形成していない炭素原子であることを特徴とする上記(B)β−ヒドロキシアルキルアミドに関する。 The present invention also relates to the above (B) β-hydroxyalkylamide, wherein the atom directly bonded to the carbonyl group in X is a carbon atom that does not form an aromatic ring.
また本発明は、Xが、分岐脂肪族炭化水素基であることを特徴とする上記(B)β−ヒドロキシアルキルアミドに関する。 The present invention also relates to the above (B) β-hydroxyalkylamide, wherein X is a branched aliphatic hydrocarbon group.
また本発明は、一般式(1)中のR1が炭化水素基であり、R2が一般式(2)で表される基であることを特徴とする上記(B)β−ヒドロキシアルキルアミドに関する。 Further, the present invention provides the above (B) β-hydroxyalkylamide, wherein R 1 in the general formula (1) is a hydrocarbon group, and R 2 is a group represented by the general formula (2). About.
また本発明は、上記(B)β−ヒドロキシアルキルアミドと、(C)有機溶剤とからなる架橋性組成物に関する。 The present invention also relates to a crosslinkable composition comprising the above (B) β-hydroxyalkylamide and (C) an organic solvent.
また本発明は、さらに、(A)カルボン酸を有する樹脂を含む上記架橋性組成物に関する。 Moreover, this invention relates to the said crosslinkable composition containing resin which has (A) carboxylic acid further.
また本発明は、請求項5または6記載の架橋性組成物を加熱してなる硬化物に関する。 Moreover, this invention relates to the hardened | cured material formed by heating the crosslinkable composition of Claim 5 or 6.
本発明により、有機溶剤に可溶であり、カルボキシ基と反応する架橋剤であるβ−ヒドロキシアルキルアミドを提供することができた。さらには、有機溶剤可溶なβ−ヒドロキシアルキルアミドを含む樹脂組成物、その硬化物、有機溶剤可溶なβ−ヒドロキシアルキルアミドの製造方法を提供することができた。 According to the present invention, β-hydroxyalkylamide, which is a crosslinking agent that is soluble in an organic solvent and reacts with a carboxy group, can be provided. Furthermore, it was possible to provide a resin composition containing an organic solvent-soluble β-hydroxyalkylamide, a cured product thereof, and a method for producing an organic solvent-soluble β-hydroxyalkylamide.
本発明の(A)カルボン酸を有する樹脂は、樹脂の末端および/または側鎖にカルボキシ基を有する樹脂である。樹脂は直鎖、分岐、星状を問わない。たとえば、カルボキシ末端のポリエステル、ポリアミド、ポリエステルアミド、ポリエーテルエステル、アクリル、ポリブタジエン、ポリイソプレン、側鎖にカルボキシを有するアクリル樹脂、などが挙げられる。 The resin (A) having a carboxylic acid of the present invention is a resin having a carboxy group at the terminal and / or side chain of the resin. The resin may be linear, branched or star-shaped. Examples include carboxy-terminated polyester, polyamide, polyesteramide, polyetherester, acrylic, polybutadiene, polyisoprene, and acrylic resin having carboxy in the side chain.
β−ヒドロキシアルキルアミドは、一般式(1)で表される化合物である。 β-hydroxyalkylamide is a compound represented by the general formula (1).
式中、Xは炭素、水素、酸素、窒素、硫黄、または、ハロゲンから構成されるn価の基であり、
脂環式炭化水素基、分岐脂肪族炭化水素基、芳香族炭化水素基、酸素、窒素、もしくは、硫黄で分断されている直鎖脂肪族炭化水素基、または、酸素、窒素、硫黄、もしくは、ハロゲンを含む置換基で置換された直鎖脂肪族炭化水素基であり、
X中のカルボニル基に直接結合する原子が炭素原子である。
nは2〜6の整数であり、
R1およびR2は、それぞれ独立に、水素原子、一般式(2)で表される基、または1価の炭化水素基を表し、R1およびR2のうち、少なくとも1つは、一般式(2)で表される基である。
In the formula, X is an n-valent group composed of carbon, hydrogen, oxygen, nitrogen, sulfur, or halogen,
An alicyclic hydrocarbon group, a branched aliphatic hydrocarbon group, an aromatic hydrocarbon group, a linear aliphatic hydrocarbon group separated by oxygen, nitrogen, or sulfur, or oxygen, nitrogen, sulfur, or A linear aliphatic hydrocarbon group substituted with a halogen-containing substituent,
The atom directly bonded to the carbonyl group in X is a carbon atom.
n is an integer of 2-6,
R 1 and R 2 each independently represent a hydrogen atom, a group represented by the general formula (2), or a monovalent hydrocarbon group, and at least one of R 1 and R 2 is represented by the general formula It is a group represented by (2).
ここで、Xは、脂環式炭化水素基、分岐脂肪族炭化水素基、芳香族炭化水素基、酸素、窒素、もしくは、硫黄で分断されている直鎖脂肪族炭化水素基、酸素、窒素、硫黄、もしくは、ハロゲンを含む置換基で置換された直鎖脂肪族炭化水素基、および、これらの組み合わせからなる基である。 Here, X is an alicyclic hydrocarbon group, a branched aliphatic hydrocarbon group, an aromatic hydrocarbon group, oxygen, nitrogen, or a linear aliphatic hydrocarbon group separated by sulfur, oxygen, nitrogen, A straight chain aliphatic hydrocarbon group substituted with a substituent containing sulfur or halogen, and a group composed of a combination thereof.
また、Xにおける炭化水素基とは、炭素、水素、酸素、窒素、硫黄から構成される基であり、酸素、窒素、硫黄、もしくは、ハロゲンを含む置換基で置換されていてもよい。 The hydrocarbon group in X is a group composed of carbon, hydrogen, oxygen, nitrogen, and sulfur, and may be substituted with a substituent containing oxygen, nitrogen, sulfur, or halogen.
ハロゲンとしては、フッ素、塩素、臭素、ヨウ素等が挙げられ、透明性の観点からはフッ素が好ましい。難燃性を付与する観点からは塩素、臭素が好ましい。 Examples of the halogen include fluorine, chlorine, bromine and iodine, and fluorine is preferable from the viewpoint of transparency. From the viewpoint of imparting flame retardancy, chlorine and bromine are preferred.
Xにおけるn価の基とは、化合物からn個の水素原子を取り除くことで得られる基である。化合物としてはたとえば、エタン、プロパン、ブタン、ペンタン、ヘキサン、ヘプタン、オクタン、ノナン、デカン、ウンデカン、ドデカン、トリデカン、テトラデカン、ペンタデカン、ヘプタデカン、ヘキサデカン、オクタデカン、ノナデカン、イコサン、ヘンイコサン、ドコサン、イソブタン、イソペンタン、ネオペンタン、メチルペンタン、ジメチルペンタン、エチルメチルペンタン、ジエチルペンタン、メチルヘキサン、テトラメチルヘプタン、エチレン、プロピレン、ブチレン、ペンテン、ヘキセン、ヘプテン、オクテン、ノネン、デセン、ウンデセン、ドセン、トリデセン、テトラセン、ペンタデセン、ヘプタデセン、ヘキサデセン、オクタデセン、ノナデセン、イコセン、ヘンイコセン、ドコセン、メチルペンテン、エチン、プロピン、ブチン、ペンチン、ヘキシン、ペプチン、オクチン、ノニン、デシン、ウンデシン、ドデシン、トリデシン、イコシン、ヘンイコシン、ドコシン、シクロプロパン、シクロブタン、シクロペンタン、メチルシクロペンタン、ジメチルシクロペンタン、トリメチルシクロペンタン、ベンゼン、ナフタレン、ビフェニル、アントラセン、トルエン、キシレン、エチルベンゼン、tert−ブチルベンゼン、ジフェニルエタン、ジフェニルアセチレン、9,9−ジフェニルフルオレン、エタノール、エチレングリコール、エチレンジアセテート、エチレンジピバレート、エチレンジベンゾエート、エチレンビス(メチルベンゾエート)、エチレンビス(メトキシベンゾエート)、プロパノール、イソプロパノール、酢酸エチル、エリスリトール、エチレンオキシド、アセトアルデヒド、アセトン、ジプロピルケトン、γ−ペンタデカノラクトン、1,2−シクロヘキサン、γ−ブチロラクトン、エチルアミン、エチルメチルアミン、プロピルアミン、N−プロピルアセトアミド、エタンチオール、エタンジチオール、テトラフルオロエタン、ジブロモエタン、ヘキサフルオロプロパン、オクトフルオロブタン、ドデカフルオロヘキサン、ヘキサデカフルオロオクタン、1,2,3,4,7,7−ヘキサクロロノルボルネン、アニソール、フルオロベンゼン、テトラフルオロベンゼン、トリフルオロメチルベンゼン、クロロベンゼン、ジクロロベンゼン、テトラクロロベンゼン、ブロモベンゼン、テトラブロモベンゼン、ニトロベンゼン、フェノール、アニリン、ベンゼンスルホン酸、アントラキノン、ブタンホスホン酸、トリエチルトリアジン、トリプロピルトリアジン、トリエチルイソシアヌレート、トリプロピルイソシアヌレート、ベンゾフェノン、チオフェン、ジエチルスルフィド、ジフェニルスルホン、2,2−ジフェニル−1,1,1,3,3,3−ヘキサフルオロプロパン、ジフェニルエーテル、等が挙げられる。 The n-valent group in X is a group obtained by removing n hydrogen atoms from a compound. Examples of the compound include ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, heptadecane, hexadecane, octadecane, nonadecane, icosane, heicosane, docosane, isobutane, isopentane. , Neopentane, methylpentane, dimethylpentane, ethylmethylpentane, diethylpentane, methylhexane, tetramethylheptane, ethylene, propylene, butylene, pentene, hexene, heptene, octene, nonene, decene, undecene, docene, tridecene, tetracene, pentadecene , Heptadecene, hexadecene, octadecene, nonadecene, icosene, henicosene, docosene, methylpentene, ethyne, Lopin, butyne, pentyne, hexyne, peptin, octyne, nonine, decyne, undecine, dodecin, tridecine, icosin, henicosin, docosin, cyclopropane, cyclobutane, cyclopentane, methylcyclopentane, dimethylcyclopentane, trimethylcyclopentane, benzene, Naphthalene, biphenyl, anthracene, toluene, xylene, ethylbenzene, tert-butylbenzene, diphenylethane, diphenylacetylene, 9,9-diphenylfluorene, ethanol, ethylene glycol, ethylene diacetate, ethylene dipivalate, ethylene dibenzoate, ethylene bis (Methylbenzoate), ethylenebis (methoxybenzoate), propanol, isopropanol, ethyl acetate, erythritol , Ethylene oxide, acetaldehyde, acetone, dipropyl ketone, γ-pentadecanolactone, 1,2-cyclohexane, γ-butyrolactone, ethylamine, ethylmethylamine, propylamine, N-propylacetamide, ethanethiol, ethanedithiol, Tetrafluoroethane, dibromoethane, hexafluoropropane, octofluorobutane, dodecafluorohexane, hexadecafluorooctane, 1,2,3,4,7,7-hexachloronorbornene, anisole, fluorobenzene, tetrafluorobenzene, trifluoro Methylbenzene, chlorobenzene, dichlorobenzene, tetrachlorobenzene, bromobenzene, tetrabromobenzene, nitrobenzene, phenol, aniline, benzenesulfone , Anthraquinone, butanephosphonic acid, triethyltriazine, tripropyltriazine, triethylisocyanurate, tripropylisocyanurate, benzophenone, thiophene, diethylsulfide, diphenylsulfone, 2,2-diphenyl-1,1,1,3,3,3 -Hexafluoropropane, diphenyl ether and the like.
反応性の観点から、カルボニル基と結合するX中の炭素原子が芳香環を形成しないことが好ましい。また、溶剤溶解性や相溶性の観点から、X中に分岐がある構造がより好ましい。 From the viewpoint of reactivity, it is preferable that the carbon atom in X bonded to the carbonyl group does not form an aromatic ring. Moreover, the structure which has a branch in X from a solvent solubility or a compatible viewpoint is more preferable.
一般式(1)中のR1およびR2はそれぞれ水素原子、1価の炭化水素基、一般式(2)で表される基を表す。 R 1 and R 2 in the general formula (1) each represent a hydrogen atom, a monovalent hydrocarbon group, or a group represented by the general formula (2).
1価の炭化水素基としては前述した炭化水素基のうち1価のものが挙げられる。 Examples of the monovalent hydrocarbon group include monovalent hydrocarbon groups described above.
1価の炭化水素基として好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、デシル基、ドデシル基、ペンタデシル基、オクタデシル基、ビニル基、1−プロペニル基、2−プロペニル基、イソプロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−オクテニル基、1−デセニル基、1−オクタデセニル基、エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−オクチニル基、1−デシニル基、1−オクタデシニル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロオクタデシル基、2−インデノ基、デカヒドロナフチル基、アダマンチル基、ジシクロペンタニル基、、フェニル基、ベンジル基、o−トリル基、m−トリル基、p−トリル基、2,4−キシリル基、p−クメニル基、メシチル基、1−ナフチル基、2−ナフチル基、1−アンスリル基、2−アンスリル基、5−アンスリル基、1−フェナンスリル基、9−フェナンスリル基、1−アセナフチル基、2−アズレニル基、1−ピレニル基、2−トリフェニレル基、o−ビフェニリル基、m−ビフェニリル基、p−ビフェニリル基等が挙げられる。 The monovalent hydrocarbon group is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, Octyl, decyl, dodecyl, pentadecyl, octadecyl, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-octenyl Group, 1-decenyl group, 1-octadecenyl group, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group, 1-decynyl group, 1-octadecynyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl , Cyclooctyl group, cyclooctadecyl group, 2-indeno group, decahydronaphthyl group, adamantyl group, dicyclopentanyl group, phenyl group, benzyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, mesityl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, Examples include 1-acenaphthyl group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group and the like.
溶解性の観点からR1は1価の炭化水素基、R2は一般式(2)で表される基であることが好ましい。 From the viewpoint of solubility, R 1 is preferably a monovalent hydrocarbon group, and R 2 is preferably a group represented by the general formula (2).
一般式(2)中のR3〜R6はそれぞれ、水素原子、1価の炭化水素基、または、ヒドロキシ基で置換された炭化水素基を表す。 R 3 to R 6 in the general formula (2) each represent a hydrogen atom, a monovalent hydrocarbon group, or a hydrocarbon group substituted with a hydroxy group.
1価の炭化水素基としては前述した1価の炭化水素基が挙げられる。 Examples of the monovalent hydrocarbon group include the monovalent hydrocarbon groups described above.
ヒドロキシ基で置換された1価の炭化水素基としてはヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシプロピル基、ヒドロキシブチル基、ヒドロキシフェニル基、ヒドロキシシクロヘキシル基、などが挙げられる。 Examples of the monovalent hydrocarbon group substituted with a hydroxy group include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxyphenyl group, and a hydroxycyclohexyl group.
本発明の(B)β−ヒドロキシアルキルアミドは、(b−1)2価以上のカルボン酸またはその誘導体と、(b−2)β位にヒドロキシ基を1つ以上有する1級または2級アミン(すなわち、窒素原子に水素原子、R1、R2が結合したアミン)とを反応させることで作製することができる。
(b−1)2価以上のカルボン酸は以下のものが挙げられる。(以下、同一化合物の別名を表す場合は《 》で表す。)
(B) β-hydroxyalkylamide of the present invention comprises (b-1) a divalent or higher carboxylic acid or derivative thereof, and (b-2) a primary or secondary amine having one or more hydroxy groups at the β-position. (In other words, it can be produced by reacting a hydrogen atom, an amine in which R 1 and R 2 are bonded to a nitrogen atom).
(B-1) Divalent or higher carboxylic acids include the following. (Hereinafter, “” is used to indicate an alias for the same compound.)
分岐飽和脂肪族ジカルボン酸:
メチルマロン酸、ジメチルマロン酸、エチルマロン酸、ジプロピルマロン酸、イソプロピルマロン酸、メチルコハク酸、ジメチルコハク酸、ブチルコハク酸、オクチルコハク酸、デシルコハク酸、ドデシルコハク酸、テトラデシルコハク酸、ヘキサデシルコハク酸、オクタデシルコハク酸、メチルグルタル酸、ジメチルグルタル酸、エチルメチルグルタル酸、ジエチルグルタル酸、メチルアジピン酸、テトラメチルピメリン酸、
Branched saturated aliphatic dicarboxylic acid:
Methylmalonic acid, dimethylmalonic acid, ethylmalonic acid, dipropylmalonic acid, isopropylmalonic acid, methylsuccinic acid, dimethylsuccinic acid, butylsuccinic acid, octylsuccinic acid, decylsuccinic acid, dodecylsuccinic acid, tetradecylsuccinic acid, hexadecylsuccinic acid Acid, octadecyl succinic acid, methyl glutaric acid, dimethyl glutaric acid, ethyl methyl glutaric acid, diethyl glutaric acid, methyl adipic acid, tetramethyl pimelic acid,
不飽和脂肪族ジカルボン酸:アリルコハク酸、メタリルコハク酸、ヘキセニルコハク酸、オクテニルコハク酸、ドデセニルコハク酸、ドコセニルコハク酸、デカジエン−1,2−ジカルボン酸、フマル酸、マレイン酸、アセチレンジカルボン酸、ムコン酸、イタコン酸、シトラコン酸、メサコン酸、 Unsaturated aliphatic dicarboxylic acids: allyl succinic acid, methallyl succinic acid, hexenyl succinic acid, octenyl succinic acid, dodecenyl succinic acid, dococenyl succinic acid, decadiene-1,2-dicarboxylic acid, fumaric acid, maleic acid, acetylenedicarboxylic acid, muconic acid, itaconic acid Citraconic acid, mesaconic acid,
脂環式ジカルボン酸:
シクロプロパンジカルボン酸、シクロブタンジカルボン酸、シクロペンタンジカルボン酸、シクロペンチルマロン酸、シクロペンタン二酢酸、
Alicyclic dicarboxylic acids:
Cyclopropanedicarboxylic acid, cyclobutanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclopentylmalonic acid, cyclopentanediacetic acid,
芳香環を有する脂肪族ジカルボン酸(カルボキシに結合する炭素原子が芳香環を形成しない):
フェニルマロン酸、ベンジルマロン酸、チオフェンマロン酸、フェニルコハク酸、ジフェニルコハク酸、
Aliphatic dicarboxylic acid having an aromatic ring (the carbon atom bonded to carboxy does not form an aromatic ring):
Phenylmalonic acid, benzylmalonic acid, thiophenmalonic acid, phenylsuccinic acid, diphenylsuccinic acid,
カルボキシ基以外に酸素原子を含む脂肪族または脂環式カルボン酸:
酒石酸、ジアセチル酒石酸、ジピバロイル酒石酸、ジベンゾイル酒石酸、ジトルオイル酒石酸、ジ(p−アニソイル)酒石酸、リンゴ酸、アセチルリンゴ酸、クエン酸、シトラマル酸、ヒドロキシメチルグルタル酸、ガラクタル酸、エポキシコハク酸、オキサル酢酸、オキソグルタル酸、オキソアゼライン酸、4,5−ジカルボキシ−γ−ペンタデカノラクトン、3,6−エポキシ−1,2,3,6−ヘキサヒドロフタル酸、ブチロラクトンジカルボン酸、
Aliphatic or alicyclic carboxylic acids containing oxygen atoms in addition to the carboxy group:
Tartaric acid, diacetyltartaric acid, dipivaloyltartaric acid, dibenzoyltartaric acid, ditoluoyltartaric acid, di (p-anisoyl) tartaric acid, malic acid, acetylmalic acid, citric acid, citramalic acid, hydroxymethylglutaric acid, galactaric acid, epoxysuccinic acid, oxalic acetic acid, Oxoglutaric acid, oxoazeleic acid, 4,5-dicarboxy-γ-pentadecanolactone, 3,6-epoxy-1,2,3,6-hexahydrophthalic acid, butyrolactone dicarboxylic acid,
窒素原子を含む脂肪族または脂環式ジカルボン酸:
アスパラギン酸、N−メチルアスパラギン酸、N−(tert−ブトキシカルボニル)−アスパラギン酸、N−(ベンジルオキシカルボニル)アスパラギン酸、N−カルバモイルアスパラギン酸、N−[(9H−フルオレン−9−イルメトキシ)カルボニル]アスパラギン酸、グリシルアスパラギン酸、3−ヒドロキシアスパラギン酸、グルタミン酸、N−アセチルグルタミン酸、N−(tert−ブトキシカルボニル)−グルタミン酸、N−(ベンジルオキシカルボニル)グルタミン酸、N−ベンゾイルグルタミン酸、N−(4−アミノベンゾイル)グルタミン酸、N−[(9H−フルオレン−9−イルメトキシ)カルボニル]グルタミン酸、メチルグルタミン酸、グリシルグルタミン酸、グアジニノグルタル酸、N−フタリルグルタミン酸、アミノアジピン酸、アミノピメリン酸、ジアミノピメリン酸、アミノスベリン酸、葉酸、メトトレキサート、
Aliphatic or alicyclic dicarboxylic acids containing nitrogen atoms:
Aspartic acid, N-methylaspartic acid, N- (tert-butoxycarbonyl) -aspartic acid, N- (benzyloxycarbonyl) aspartic acid, N-carbamoylaspartic acid, N-[(9H-fluoren-9-ylmethoxy) carbonyl ] Aspartic acid, glycylaspartic acid, 3-hydroxyaspartic acid, glutamic acid, N-acetylglutamic acid, N- (tert-butoxycarbonyl) -glutamic acid, N- (benzyloxycarbonyl) glutamic acid, N-benzoylglutamic acid, N- ( 4-Aminobenzoyl) glutamic acid, N-[(9H-fluoren-9-ylmethoxy) carbonyl] glutamic acid, methylglutamic acid, glycylglutamic acid, guadininoglutaric acid, N-phthalylglutamine , Amino adipic acid, aminopimelic acid, diaminopimelic acid, aminosuberic acid, folic acid, methotrexate,
硫黄原子を含む脂肪族または脂環式ジカルボン酸:
ジメルカプトコハク酸、チオリンゴ酸、
Aliphatic or alicyclic dicarboxylic acids containing sulfur atoms:
Dimercaptosuccinic acid, thiomalic acid,
ハロゲン原子を含む脂肪族または脂環式ジカルボン酸:
テトラフルオロコハク酸、ジブロモコハク酸、ヘキサフルオログルタル酸、オクタフルオロアジピン酸、ドデカフルオロスベリン酸、ヘキサデカフルオロセバシン酸、クロレンド酸《ヘット酸》、
Aliphatic or alicyclic dicarboxylic acids containing halogen atoms:
Tetrafluorosuccinic acid, dibromosuccinic acid, hexafluoroglutaric acid, octafluoroadipic acid, dodecafluorosuberic acid, hexadecafluorosebacic acid, chlorendic acid 《Het's acid》,
芳香族ジカルボン酸:
フタル酸、メチルフタル酸、tert−ブチルフタル酸、エチニルフタル酸、(フェニルエチニル)フタル酸、メトキシフタル酸、フルオロフタル酸、テトラフルオロフタル酸、トリフルオロメチルフタル酸、クロロフタル酸、ジクロロフタル酸、テトラクロロフタル酸、ブロモフタル酸、テトラブロモフタル酸、ニトロフタル酸、ヒドロキシフタル酸、アミノフタル酸、スルホフタル酸、イソフタル酸、メチルイソフタル酸、tert−ブチルイソフタル酸、メトキシイソフタル酸、テトラフルオロイソフタル酸、ブロモイソフタル酸、ニトロイソフタル酸、ヒドロキシイソフタル酸、アミノイソフタル酸、アミノトリヨードイソフタル酸、スルホイソフタル酸、テレフタル酸、ジメチルテレフタル酸、テトラフルオロテレフタル酸、ジクロロテレフタル酸、テトラクロロテレフタル酸、ブロモテレフタル酸、テトラブロモテレフタル酸、ニトロテレフタル酸、ジヒドロキシテレフタル酸、アミノテレフタル酸、スルホテレフタル酸、
ナフタレンジカルボン酸、アントラセンジカルボン酸、アントラキノンジカルボン酸、1,3−ジベンジル−2−オキソ−4,5−イミダゾリジンジカルボン酸、
Aromatic dicarboxylic acids:
Phthalic acid, methylphthalic acid, tert-butylphthalic acid, ethynylphthalic acid, (phenylethynyl) phthalic acid, methoxyphthalic acid, fluorophthalic acid, tetrafluorophthalic acid, trifluoromethylphthalic acid, chlorophthalic acid, dichlorophthalic acid, tetrachloro Phthalic acid, bromophthalic acid, tetrabromophthalic acid, nitrophthalic acid, hydroxyphthalic acid, aminophthalic acid, sulfophthalic acid, isophthalic acid, methylisophthalic acid, tert-butylisophthalic acid, methoxyisophthalic acid, tetrafluoroisophthalic acid, bromoisophthalic acid, Nitroisophthalic acid, Hydroxyisophthalic acid, Aminoisophthalic acid, Aminotriiodoisophthalic acid, Sulfoisophthalic acid, Terephthalic acid, Dimethylterephthalic acid, Tetrafluoroterephthalic acid, Dichloromethane Roterefutaru acid, tetrachlorophthalic terephthalic acid, bromo terephthalic acid, tetrabromophthalic terephthalic acid, nitroterephthalic acid, dihydroxy terephthalic acid, aminoterephthalic acid, sulfoterephthalic acid,
Naphthalenedicarboxylic acid, anthracene dicarboxylic acid, anthraquinone dicarboxylic acid, 1,3-dibenzyl-2-oxo-4,5-imidazolidine dicarboxylic acid,
脂肪族または脂環式トリカルボン酸:
トリカルバリル酸《1,2,3−プロパントリカルボン酸》、アニコット酸、ブテントリカルボン酸、シクロヘキサントリカルボン酸、2−ホスホノブタン−1,2,4−トリカルボン酸、3−ブテン−1,2,3−トリカルボン酸、シクロヘキサントリカルボン酸、ペンタントリカルボン酸、トリス(2−カルボキシエチル)−1,3,5−トリアジン、トリス(3−カルボキシプロピル)−1,3,5−トリアジン、イソシアヌル酸トリス(2−カルボキシエチル)、イソシアヌル酸トリス(3−カルボキシプロピル)、
Aliphatic or alicyclic tricarboxylic acids:
Tricarballylic acid << 1,2,3-propanetricarboxylic acid >>, anicotic acid, butenetricarboxylic acid, cyclohexanetricarboxylic acid, 2-phosphonobutane-1,2,4-tricarboxylic acid, 3-butene-1,2,3-tricarboxylic acid Acid, cyclohexanetricarboxylic acid, pentanetricarboxylic acid, tris (2-carboxyethyl) -1,3,5-triazine, tris (3-carboxypropyl) -1,3,5-triazine, isocyanuric acid tris (2-carboxyethyl) ), Isocyanuric acid tris (3-carboxypropyl),
芳香族トリカルボン酸:
トリメリット酸、ヘミメリット酸、ベンゼン−1,3,5−トリカルボン酸、ベンゾフェノントリカルボン酸、
Aromatic tricarboxylic acid:
Trimellitic acid, hemimellitic acid, benzene-1,3,5-tricarboxylic acid, benzophenone tricarboxylic acid,
脂肪族または脂環式テトラカルボン酸:
ブタンテトラカルボン酸、シクロブタンテトラカルボン酸、シクロペンタンテトラカルボン酸、シクロヘキサンテトラカルボン酸、チオジコハク酸、テトラヒドロフランテトラカルボン酸、ビシクロ[2.2.2]オクト−7−エン−2,3,5,6−テトラカルボン酸、5−(1,2−ジカルボキシエチル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸、4−(1,2−ジカルボキシエチル)1,2,3,4−テトラヒドロナフタレン−1,2−ジカルボン酸、
Aliphatic or alicyclic tetracarboxylic acid:
Butanetetracarboxylic acid, cyclobutanetetracarboxylic acid, cyclopentanetetracarboxylic acid, cyclohexanetetracarboxylic acid, thiodisuccinic acid, tetrahydrofurantetracarboxylic acid, bicyclo [2.2.2] oct-7-ene-2,3,5,6 -Tetracarboxylic acid, 5- (1,2-dicarboxyethyl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid, 4- (1,2-dicarboxyethyl) 1,2,3,4 -Tetrahydronaphthalene-1,2-dicarboxylic acid,
芳香族テトラカルボン酸:
ピロメリット酸、ベンゾフェノンンテトラカルボン酸、ビフェニルテトラカルボン酸、ジフェニルスルホンテトラカルボン酸、オキシジフタル酸、ヘキサフルオロイソプロピリデンジフタル酸、ナフタレンテトラカルボン酸、フルオレン−9,9−ビスフタル酸、
Aromatic tetracarboxylic acid:
Pyromellitic acid, benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, diphenyl sulfone tetracarboxylic acid, oxydiphthalic acid, hexafluoroisopropylidenediphthalic acid, naphthalene tetracarboxylic acid, fluorene-9,9-bisphthalic acid,
脂肪族または脂環式のペンタカルボン酸またはヘキサカルボン酸:
シクロヘキサンヘキサカルボン酸、
Aliphatic or alicyclic pentacarboxylic acid or hexacarboxylic acid:
Cyclohexane hexacarboxylic acid,
脂肪族または脂環式のペンタカルボン酸またはヘキサカルボン酸:
ベンゼンペンタカルボン酸、メリット酸
Aliphatic or alicyclic pentacarboxylic acid or hexacarboxylic acid:
Benzene pentacarboxylic acid, merit acid
また(b−1)2価以上のカルボン酸として、カルボン酸を末端および/または側鎖に有するポリエステル、ポリブタジエン、ポリイソプレン、アクリルオリゴマー、あるいは、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオール、ポリブタジエンポリオール、ポリイソプレンポリオール、ポリアクリルポリオール、などのポリオールを酸無水物、たとえば無水コハク酸、無水マレイン酸、無水フタル酸、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、無水トリメリット酸、無水ピロメリット酸、などで変性して得られる化合物も挙げられる。 (B-1) As a carboxylic acid having 2 or more valences, polyester, polybutadiene, polyisoprene, acrylic oligomer, or polyether polyol, polyester polyol, polycarbonate polyol, polybutadiene polyol, having carboxylic acid at the terminal and / or side chain, Polyisoprene polyol, polyacryl polyol, and other polyols such as succinic anhydride, maleic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, trimellitic anhydride, pyromellitic anhydride, etc. Also included are compounds obtained by modification with.
カルボン酸の誘導体としては上記カルボン酸の酸無水物、酸クロリド、酸ブロミド、メチルエステル、エチルエステル、フェニルエステル、などが挙げられる。 Examples of carboxylic acid derivatives include acid anhydrides, acid chlorides, acid bromides, methyl esters, ethyl esters, and phenyl esters of the above carboxylic acids.
(b−2)β位にヒドロキシ基を1つ以上有する1級または2級アミンは以下のような例が挙げられる。 (B-2) Examples of the primary or secondary amine having one or more hydroxy groups at the β-position include the following.
1級アミン(R1が水素原子でR2が一般式(2)で表されるアミン):
エタノールアミン、1−アミノ−2−プロパノール《イソプロパノールアミン》、2−アミノ−1−プロパノール、2−アミノ−1−ブタノール、2−アミノ−2−フェニル−エタノール、2−アミノ−2−メチル−1−プロパノール、イソロイシノール《2−アミノ−3−メチル−1−ペンタノール》、2−イソプロピルアミノ−3−メチル−1−ブタノール、ロイシノール《2−アミノ−4−メチル−1−ペンタノール》、tert−ロイシノール《2―アミノ−3,3−ジメチル−1−ブタノール》、フェニルアラニノール《2−アミノ−3−フェニル−1−プロパノール》、1−アミノ−2−ブタノール、2−アミノ−1−フェニルエタノール、2−アミノ−1−フェニル−1−プロパノール、
Primary amine (R 1 is a hydrogen atom and R 2 is an amine represented by the general formula (2)):
Ethanolamine, 1-amino-2-propanol <isopropanolamine>, 2-amino-1-propanol, 2-amino-1-butanol, 2-amino-2-phenyl-ethanol, 2-amino-2-methyl-1 -Propanol, isoleucinol << 2-amino-3-methyl-1-pentanol >>, 2-isopropylamino-3-methyl-1-butanol, leucinol << 2-amino-4-methyl-1-pentanol >>, tert- Leucinol << 2-amino-3,3-dimethyl-1-butanol >>, phenylalaninol << 2-amino-3-phenyl-1-propanol >>, 1-amino-2-butanol, 2-amino-1-phenylethanol 2-amino-1-phenyl-1-propanol,
R1が炭化水素基で、R2が一般式(2)で表される2級アミン:
N−メチルエタノールアミン、N−エチルエタノールアミン、N−ブチルエタノールアミン、N−tert−ブチルエタノールアミン、3−tert−ブチルアミノ−1,2−プロパンジオール、N−シクロヘキシルエタノールアミン、N−フェニルエタノールアミン、N−ベンジルエタノールアミン、
A secondary amine in which R 1 is a hydrocarbon group and R 2 is represented by the general formula (2):
N-methylethanolamine, N-ethylethanolamine, N-butylethanolamine, N-tert-butylethanolamine, 3-tert-butylamino-1,2-propanediol, N-cyclohexylethanolamine, N-phenylethanol Amine, N-benzylethanolamine,
R1、R2とも一般式(2)で表される2級アミン:
ジエタノールアミン、ジイソプロパノールアミン、
A secondary amine represented by the general formula (2) for both R 1 and R 2 :
Diethanolamine, diisopropanolamine,
R3〜R6の中にヒドロキシ置換炭化水素基が含まれるアミン:
2−[(ヒドロキシメチル)アミノ]エタノール、2−アミノ−1,3−プロパンジオール、2−アミノ−2−メチル−1,3−プロパンジオール、トリス(ヒドロキシメチル)アミノメタン、3−アミノ−1,2−プロパンジオール、3−(メチルアミノ)−1,2−プロパンジオール、N−メチルグルカミン《6−(メチルアミノ)−1,2,3,4,5−ヘキサンペンタオール》、1,3−ビス[トリス(ヒドロキシメチル)メチルアミノ]プロパン、2−アミノ−1−フェニル−1,3−プロパンジオール、フェニレフリン《1−(3−ヒドロキシフェニル)−2−(メチルアミノ)エタノール》、エチレフリン《2−エチルアミノ−1−(3−ヒドロキシフェニル)エタノール》、
Amines containing a hydroxy-substituted hydrocarbon group in R 3 to R 6 :
2-[(hydroxymethyl) amino] ethanol, 2-amino-1,3-propanediol, 2-amino-2-methyl-1,3-propanediol, tris (hydroxymethyl) aminomethane, 3-amino-1 , 2-propanediol, 3- (methylamino) -1,2-propanediol, N-methylglucamine << 6- (methylamino) -1,2,3,4,5-hexanepentaol >>, 3-bis [tris (hydroxymethyl) methylamino] propane, 2-amino-1-phenyl-1,3-propanediol, phenylephrine << 1- (3-hydroxyphenyl) -2- (methylamino) ethanol >>, ethylephrine << 2-ethylamino-1- (3-hydroxyphenyl) ethanol >>
本発明の(B)β−ヒドロキシアルキルアミドは、(b−1)2価以上のカルボン酸またはその誘導体と、(b−2)β位にヒドロキシ基を1つ以上有する1級または2級アミンと、をアミド化することで製造することができる。 (B) β-hydroxyalkylamide of the present invention comprises (b-1) a divalent or higher carboxylic acid or derivative thereof, and (b-2) a primary or secondary amine having one or more hydroxy groups at the β-position. And can be produced by amidation.
(b−1)2価以上のカルボン酸またはその誘導体と、(b−2)β位にヒドロキシ基を1つ以上有する1級または2級アミンと、をアミド化する方法は様々あるが、(b−1)2価以上のカルボン酸またはその誘導体がカルボン酸の場合は水、カルボン酸エステルの場合はアルコール、カルボン酸無水物またはハロゲン化物の場合は酸を取り除くことで反応を進行させることができる。水やアルコールの場合は加熱により反応系外へ除去することが容易である。酸の場合はトリエチルアミン、トリブチルアミン、ジメチルベンジルアミン、ピリジン、ジメチルアミノピリジン、1,8−ジアザビシクロ[5.4.0]−7−ウンデセン、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウムなどの塩基性化合物によって取り除くことができる。 There are various methods for amidating (b-1) a divalent or higher carboxylic acid or derivative thereof and (b-2) a primary or secondary amine having one or more hydroxy groups at the β-position. b-1) The reaction can be allowed to proceed by removing water when the divalent or higher carboxylic acid or derivative thereof is a carboxylic acid, alcohol when it is a carboxylic acid ester, and acid when it is a carboxylic acid anhydride or halide. it can. In the case of water or alcohol, it is easy to remove out of the reaction system by heating. In the case of acid, triethylamine, tributylamine, dimethylbenzylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. The basic compound can be removed.
上記アミド化の際に触媒を使用することができる。たとえば、硫酸、塩酸、メタンスルホン酸、p−トルエンスルホン酸などの酸触媒、水酸化ナトリウム、炭酸ナトリウム、ナトリウムメトキシドなどの塩基触媒、トリエチルアミン、トリブチルアミン、トリオクチルアミン、テトラメチルエチレンジアミン、N,N−ジメチルエタノールアミン、N,N−ジメチルベンジルアミン、ピリジン、4−(ジメチルアミノ)ピリジン、イミダゾール、N−メチルイミダゾールなどのアミン類、鉄(III)、ジルコニウム(IV)、スカンジウム(III)、チタン(IV)、スズ(IV)、ハフニウム(IV)などの金属イオンを含む塩や錯体、ジフェニルアンモニウムトリフラート、ペンタフルオロフェニルアンモニウムトリフラートなどのアンモニウム塩、などが挙げられる。 A catalyst can be used in the amidation. For example, acid catalysts such as sulfuric acid, hydrochloric acid, methanesulfonic acid, p-toluenesulfonic acid, base catalysts such as sodium hydroxide, sodium carbonate, sodium methoxide, triethylamine, tributylamine, trioctylamine, tetramethylethylenediamine, N, N-dimethylethanolamine, N, N-dimethylbenzylamine, pyridine, 4- (dimethylamino) pyridine, imidazole, amines such as N-methylimidazole, iron (III), zirconium (IV), scandium (III), Examples thereof include salts and complexes containing metal ions such as titanium (IV), tin (IV), and hafnium (IV), and ammonium salts such as diphenylammonium triflate and pentafluorophenylammonium triflate.
上記アミド化反応において、必要に応じて溶媒や触媒を使用することができる。使用する溶媒は、アルコール、アミン、カルボン酸など反応基質と反応する溶媒以外であれば使用できる。たとえば、ヘキサン、ヘプタン、オクタン、シクロヘキサン、ベンゼン、トルエン、エチルベンゼン、キシレン、酢酸エチル、酢酸ブチル、酢酸イソブチル、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、ジクロロメタン、クロロホルム、ジメチルスルホキシド、ジメチルホルムアミド、ジメチルアセトアミドなどが挙げられる。 In the amidation reaction, a solvent or a catalyst can be used as necessary. The solvent to be used can be used as long as it is other than a solvent that reacts with a reaction substrate such as alcohol, amine, or carboxylic acid. For example, hexane, heptane, octane, cyclohexane, benzene, toluene, ethylbenzene, xylene, ethyl acetate, butyl acetate, isobutyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, etc. It is done.
特にカルボン酸とのアミド化において、縮合剤を用いて行うことができる。縮合剤とは、カルボン酸またはアミンを活性化させ、エステル化反応を温和な条件で行うことができると同時に、副生成物の水は縮合剤と結合して別の化合物となるため、触媒作用と水除去作用を兼ね備えた化合物である。このような縮合剤としては、たとえば、ジシクロヘキシルカルボジイミド、ジイソプロピルカルボジイミド、p−トルエンスルホニルクロリド、1−エチル−3−(N,N−ジメチルアミノプロピル)カルボジイミド塩酸塩、カルボニルジイミダゾール、クロロギ酸エチル、クロロギ酸イソブチル、2,4,6−トリクロロ安息香酸クロリド、2−メチル−6−ニトロ安息香酸無水物、O−(7−アザベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスファートなどが挙げられる。 In particular, the amidation with carboxylic acid can be performed using a condensing agent. A condensing agent activates a carboxylic acid or an amine, and the esterification reaction can be carried out under mild conditions. At the same time, the by-product water is combined with the condensing agent to form another compound. And a compound having a water removing action. Such condensing agents include, for example, dicyclohexylcarbodiimide, diisopropylcarbodiimide, p-toluenesulfonyl chloride, 1-ethyl-3- (N, N-dimethylaminopropyl) carbodiimide hydrochloride, carbonyldiimidazole, ethyl chloroformate, chloroformate Acid isobutyl, 2,4,6-trichlorobenzoic acid chloride, 2-methyl-6-nitrobenzoic anhydride, O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′— Examples thereof include tetramethyluronium hexafluorophosphate.
本発明は(B)β−ヒドロキシアルキルアミドが(C)有機溶剤に可溶であることが特徴である。(C)有機溶剤としては、たとえば、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール、sec−ブタノール、tert−ブタノール、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、ベンゼン、トルエン、エチルベンゼン、キシレン、シクロヘキサン、ヘキサン、オクタン、シクロロメタン、クロロホルム、ジメチルホルムアミド、ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、などが挙げられる。 The present invention is characterized in that (B) β-hydroxyalkylamide is soluble in (C) an organic solvent. (C) As an organic solvent, for example, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, tert-butanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate, propyl acetate, Examples include butyl acetate, benzene, toluene, ethylbenzene, xylene, cyclohexane, hexane, octane, cyclomethane, chloroform, dimethylformamide, dimethylacetamide, acetonitrile, dimethyl sulfoxide, and the like.
本発明の樹脂組成物は、さらに、必要に応じて、非反応性樹脂、熱硬化性樹脂、光硬化性樹脂、併用する硬化剤、光開始剤、増感剤、レベリング剤、紫外線吸収剤、光安定剤、酸化防止剤、無機フィラー、接着付与剤、などの添加剤を加えてもよい。 The resin composition of the present invention further comprises a non-reactive resin, a thermosetting resin, a photocurable resin, a curing agent used in combination, a photoinitiator, a sensitizer, a leveling agent, an ultraviolet absorber, if necessary. You may add additives, such as a light stabilizer, antioxidant, an inorganic filler, and an adhesion imparting agent.
本発明の樹脂組成物を、各種基材の片面または両面に塗布し、もしくは金型等を用いて成形後、必要に応じて加熱乾燥後、100〜200℃において加熱硬化させることで目的の硬化物を得ることができる。基材としては、たとえば、ガラス、セラミック、ポリカーボネート、ポリエステル、ウレタン、アクリル、ポリアセテートセルロース、ポリアミド、ポリイミド、ポリスチレン、エポキシ樹脂、ポリオレフィン、ポリシクロオレフィン、ポリビニルアルコール、ステンレス等の各種金属、などが挙げられる。 The resin composition of the present invention is applied to one or both surfaces of various base materials, or molded using a mold or the like, and after heat drying as necessary, it is cured by heating at 100 to 200 ° C. to achieve the desired curing. You can get things. Examples of the base material include glass, ceramic, polycarbonate, polyester, urethane, acrylic, polyacetate cellulose, polyamide, polyimide, polystyrene, epoxy resin, polyolefin, polycycloolefin, polyvinyl alcohol, various metals such as stainless steel, and the like. It is done.
以下に実施例をもって本発明を具体的に説明するが、本発明はこれらに限定されるものではない。なお、特に断りのない限り「%」は「重量%」を、「部」は「重量部」を意味する。 EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, “%” means “% by weight” and “parts” means “parts by weight”.
実施例中のNMR測定はすべて、JEOL社製のJNM−ECX400Pを用いて1H−NMR測定をDMSO−d6中で行った。数平均分子量(Mn)と重量平均分子量(Mw)は東ソー社製のGPC−8020によって測定したポリスチレン換算の値である。 All NMR measurements in the examples were performed in DMSO-d6 using 1H-NMR measurement using JNM-ECX400P manufactured by JEOL. The number average molecular weight (Mn) and the weight average molecular weight (Mw) are values in terms of polystyrene measured by GPC-8020 manufactured by Tosoh Corporation.
実施例中のIR測定はすべて、PerkinElmer社製のSpectrum Oneを用いて行った。 All IR measurements in the examples were performed using Spectrum One manufactured by PerkinElmer.
(B)β−ヒドロキシアルキルアミドの合成
実施例1
(B) Synthesis of β-hydroxyalkylamide Example 1
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、2,4−ジエチルグルタル酸188部、N−ブチルエタノールアミン234部、水酸化カリウム10部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 188 parts 2,4-diethylglutaric acid, 234 parts N-butylethanolamine, 10 parts potassium hydroxide, 300 parts of toluene was added, the Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例2
Example 2
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、ドデシルコハク酸無水物268部、硫酸5部、トルエン300部を入れ、40℃に保ちながら、2―アミノ−4−メチル−1−ペンタノール234部を滴下装置から2時間かけて滴下した。滴下終了後、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 268 parts of dodecyl succinic anhydride, 5 parts of sulfuric acid, and 300 parts of toluene were added and maintained at 40 ° C. 234 parts of 2-amino-4-methyl-1-pentanol was dropped from a dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例3
Example 3
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、2−ブチルオクタン二酸230.3部、ジイソプロパノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 230.3 parts 2-butyloctanedioic acid, 210 parts diisopropanolamine, 5 parts sulfuric acid, 300 parts toluene The Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例4
Example 4
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、3−メチルアジピン酸160部、N−ベンジルエタノールアミン302部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 160 parts of 3-methyladipic acid, 302 parts of N-benzylethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene The Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例5
Example 5
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、4−tert−ブチル無水フタル酸204部、硫酸5部、トルエン300部を入れ、40℃に保ちながら、2―アミノ−3−メチル−1−ペンタノール234部を滴下装置から2時間かけて滴下した。滴下終了後、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 204 parts of 4-tert-butyl phthalic anhydride, 5 parts of sulfuric acid, and 300 parts of toluene are placed at 40 ° C. While maintaining, 234 parts of 2-amino-3-methyl-1-pentanol was dropped from a dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例6
Example 6
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、無水トリメリット酸クロリド204部、ピリジン79部、トルエン300部を入れ、40℃に保ちながら、N−エチルエタノールアミン267部を滴下装置から2時間かけて滴下した。滴下終了後、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエン溶液を10%塩酸500部、飽和炭酸水素ナトリウム水溶液500部、飽和食塩水500部で洗浄したのち、無水硫酸マグネシウムで乾燥した。これをロータリーエバポレーターで溶媒のジクロロメタンを除去したのち、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 204 parts of trimellitic acid chloride, 79 parts of pyridine, and 300 parts of toluene were added and maintained at 40 ° C. 267 parts of N-ethylethanolamine was added dropwise from the dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy. After 4 hours, the toluene solution was washed with 500 parts of 10% hydrochloric acid, 500 parts of a saturated aqueous sodium hydrogen carbonate solution and 500 parts of saturated brine, and then dried over anhydrous magnesium sulfate. After removing the dichloromethane of the solvent with a rotary evaporator, 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. Methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例7
Example 7
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、シクロペンタン−1,2,3,4−テトラカルボン酸246部、N−メチルアミノエタノール300部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 246 parts of cyclopentane-1,2,3,4-tetracarboxylic acid, 300 parts of N-methylaminoethanol Then, 5 parts of sulfuric acid and 300 parts of toluene were added, and the Dean-Stark tube was filled with toluene, heated and refluxed while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例8
Example 8
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、イソシアヌル酸トリス(2−カルボキシエチル)345部、2−ブチルアミノエタノール352部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 345 parts of tris (2-carboxyethyl) isocyanurate, 352 parts of 2-butylaminoethanol, 5 parts of sulfuric acid, 300 parts of toluene was added, the Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例9
Example 9
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、ダイマー酸561部、ジイソプロパノールアミン266部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 561 parts of dimer acid, 266 parts of diisopropanolamine, 5 parts of sulfuric acid, and 300 parts of toluene were added, and Dean-Stark tube Was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例10
Example 10
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、2−ドデセニルコハク酸無水物226部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 226 parts of 2-dodecenyl succinic anhydride, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene are added. The Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例11
Example 11
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、テトラプロペニル無水コハク酸226部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 Add 226 parts tetrapropenyl succinic anhydride, 210 parts diethanolamine, 5 parts sulfuric acid, and 300 parts toluene to a reaction vessel equipped with a stirrer, thermometer, dripping device, Dean-Stark tube, reflux condenser, and gas introduction tube. The tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例12
Example 12
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、2−オクテニル無水コハク酸210部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dripping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of 2-octenyl succinic anhydride, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene are added. The Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例13
Example 13
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、クエン酸192部、2−ブチルアミノエタノール352部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 192 parts of citric acid, 352 parts of 2-butylaminoethanol, 5 parts of sulfuric acid and 300 parts of toluene are placed in a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube. The Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例14
Example 14
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、exo−3,6−エポキシ−1,2,3,6−テトラヒドロフタル酸無水物166部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 166 parts of exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride, Diethanolamine (210 parts), sulfuric acid (5 parts), and toluene (300 parts) were charged. The Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例15
Example 15
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、オクタフルオロアジピン酸290部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 290 parts of octafluoroadipic acid, 210 parts of diethanolamine, 5 parts of sulfuric acid and 300 parts of toluene are placed in a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube. Was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例16
Example 16
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、ヘット酸無水物370部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 370 parts of het acid anhydride, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene were added, and Dean-Stark tube Was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例17
Example 17
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、テトラブロモフタル酸無水物464部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 Into a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 464 parts of tetrabromophthalic anhydride, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene were added. The Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
実施例18
Example 18
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、2,5−チオフェンジカルボン酸172部、ジエタノールアミン210部、硫酸5部、トルエン300部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃に冷却したのち、メチルエチルケトンを加え、NV=80%になるよう調整した。得られた均一な黄褐色透明の溶液を取り出した。 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 172 parts of 2,5-thiophenedicarboxylic acid, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene were placed. The Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., methyl ethyl ketone was added to adjust to NV = 80%. The obtained uniform yellowish brown transparent solution was taken out.
樹脂合成例1 (A)カルボン酸を有する樹脂の合成
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器にメチルエチルケトンを500部入れ、窒素を吹き込みながら70℃で1時間加熱攪拌した。その後、ブチルアクリレート374.4部、アクリル酸25.6部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)11.4部、メチルエチルケトン100部を混合した溶液を滴下装置から2時間かけて滴下した。さらに70℃で2時間反応させ、2,2’−アゾビス(2,4−ジメチルバレロニトリル)1.1部とメチルエチルケトン10部からなる溶液を加え、さらに1時間攪拌した。できた樹脂溶液は固形分NV=39.1%、数平均分子量Mn=16,000、重量平均分子量Mw=34,000、酸価AV=50.2mgKOH/gであった。
Resin synthesis example 1 (A) Synthesis of resin having carboxylic acid 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. for 1 hour. Stir with heating. Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device over 2 hours. And dripped. The mixture was further reacted at 70 ° C. for 2 hours, a solution consisting of 1.1 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 10 parts of methyl ethyl ketone was added, and the mixture was further stirred for 1 hour. The resulting resin solution had a solid content NV = 39.1%, a number average molecular weight Mn = 16,000, a weight average molecular weight Mw = 34,000, and an acid value AV = 50.2 mgKOH / g.
樹脂合成例2 (A)カルボン酸を有する樹脂の合成
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器にブチルカルビトールを500部入れ、窒素を吹き込みながら70℃で1時間加熱攪拌した。その後、ブチルアクリレート374.4部、アクリル酸25.6部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)11.4部、ブチルカルビトール100部を混合した溶液を滴下装置から2時間かけて滴下した。さらに70℃で2時間反応させ、2,2’−アゾビス(2,4−ジメチルバレロニトリル)1.1部とブチルカルビトール10部からなる溶液を加え、さらに1時間攪拌した。できた樹脂溶液は固形分NV=39.3%、数平均分子量Mn=14,000、重量平均分子量Mw=32,000、酸価AV=50.1mgKOH/gであった。
Resin Synthesis Example 2 (A) Synthesis of Resin Having Carboxylic Acid 500 parts of butyl carbitol was placed in a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. Stir with heating for 1 hour. Thereafter, 24.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile), and 100 parts of butyl carbitol were added from a dropping device with 2 It was added dropwise over time. The mixture was further reacted at 70 ° C. for 2 hours, a solution consisting of 1.1 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 10 parts of butyl carbitol was added, and the mixture was further stirred for 1 hour. The resulting resin solution had a solid content NV = 39.3%, a number average molecular weight Mn = 14,000, a weight average molecular weight Mw = 32,000, and an acid value AV = 50.1 mgKOH / g.
樹脂合成例3 比較合成例:ヒドロキシ基を有する樹脂の合成
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器に、メチルエチルケトンを500部入れ、窒素を吹き込みながら70℃で1時間加熱攪拌した。その後、ブチルアクリレート358.8部、2−ヒドロキシエチルアクリレート41.2部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)11.4部、メチルエチルケトン100部を混合した溶液を滴下装置から2時間かけて滴下した。さらに70℃で2時間反応させ、2,2’−アゾビス(2,4−ジメチルバレロニトリル)1.1部とメチルエチルケトン10部からなる溶液を加え、さらに1時間攪拌した。できた樹脂溶液は固形分NV=39.4%、数平均分子量Mn=14,000、重量平均分子量Mw=32,000、水酸基価OHV=50.0mgKOH/gであった。
Resin synthesis example 3 Comparative synthesis example: Synthesis of a resin having a hydroxy group 500 parts of methyl ethyl ketone was placed in a reaction vessel equipped with a stirrer, a thermometer, a dripping device, a reflux condenser, and a gas introduction tube at 70 ° C. while blowing nitrogen. Stir with heating for 1 hour. Thereafter, a solution in which 358.8 parts of butyl acrylate, 41.2 parts of 2-hydroxyethyl acrylate, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device. It was dripped over 2 hours. The mixture was further reacted at 70 ° C. for 2 hours, a solution consisting of 1.1 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 10 parts of methyl ethyl ketone was added, and the mixture was further stirred for 1 hour. The resulting resin solution had a solid content NV = 39.4%, a number average molecular weight Mn = 14,000, a weight average molecular weight Mw = 32,000, and a hydroxyl value OHV = 50.0 mgKOH / g.
実施例19
実施例1の(B)β−ヒドロキシアルキルアミドの溶解性試験、硬化試験、保存安定性試験、を行った。
Example 19
The solubility test, curing test, and storage stability test of (B) β-hydroxyalkylamide of Example 1 were performed.
溶解性試験は次のように行った。実施例1の(B)β−ヒドロキシアルキルアミドをメチルエチルケトンで希釈し、NV=50%になるようにした。そのときに均一な液体として得られたものは○、液体が2層に分かれた、または、固体が沈殿した場合は×とした。 The solubility test was performed as follows. The (B) β-hydroxyalkylamide of Example 1 was diluted with methyl ethyl ketone so that NV = 50%. At that time, what was obtained as a uniform liquid was marked with ◯, and when the liquid was separated into two layers or when a solid was precipitated, it was marked with x.
硬化試験(1)は次のように行なった。実施例1の(B)β−ヒドロキシアルキルアミドと樹脂合成例1の(A)カルボン酸を有する樹脂を、(B)β−ヒドロキシアルキルアミドのヒドロキシ基と、(A)カルボン酸を有する樹脂のカルボキシ基とのモル比が1:1になるように配合し樹脂溶液を作製した。この溶液1gをアルミ容器に入れた。この容器を150℃のオーブンに1時間入れ、樹脂を硬化させた。硬化膜をメチルエチルケトンで洗浄し、洗浄時に膜が残ったものを○、洗い流されたものは×とした。 The curing test (1) was performed as follows. Resin having (B) β-hydroxyalkylamide of Example 1 and (A) carboxylic acid of Resin Synthesis Example 1 is the same as that of (B) a resin having a hydroxy group of β-hydroxyalkylamide and (A) carboxylic acid. A resin solution was prepared by blending such that the molar ratio with the carboxy group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ◯, and the washed film was marked with x.
硬化試験(2)は次のように行なった。実施例1の(B)β−ヒドロキシアルキルアミドと樹脂合成例2の(A)カルボン酸を有する樹脂を、(B)β−ヒドロキシアルキルアミドのヒドロキシ基と、(A)カルボン酸を有する樹脂のカルボキシ基とのモル比が1:1になるように配合し樹脂溶液を作製した。この溶液1gをアルミ容器に入れた。この容器を150℃のオーブンに1時間入れ、樹脂を硬化させた。硬化膜をメチルエチルケトンで洗浄し、洗浄時に膜が残ったものを○、洗い流されたものは×とした。 The curing test (2) was performed as follows. Resin having (B) β-hydroxyalkylamide in Example 1 and (A) carboxylic acid in Resin Synthesis Example 2 is the same as that of (B) the hydroxyl group of β-hydroxyalkylamide and (A) resin having carboxylic acid. A resin solution was prepared by blending such that the molar ratio with the carboxy group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ◯, and the washed film was marked with x.
保存安定性試験は次のように行なった。硬化試験で用いた樹脂溶液の粘度を測定した。その後、40℃で1週間保存し、1週間後の粘度を測定した。試験前の粘度と比較して粘度変化が5%以内のものを○、5%以上増加したものを×とした。 The storage stability test was conducted as follows. The viscosity of the resin solution used in the curing test was measured. Thereafter, it was stored at 40 ° C. for 1 week, and the viscosity after 1 week was measured. When the viscosity change was within 5% compared to the viscosity before the test, the case where the viscosity was 5% or more was rated as x.
実施例20〜36
実施例2〜18の(B)β−ヒドロキシアルキルアミドを、実施例1で合成した(B)β−ヒドロキシアルキルアミドの代わりに使用した以外は、実施例19と同様に溶解性試験、硬化試験、保存安定性試験を行った。
Examples 20-36
A solubility test and a curing test were performed in the same manner as in Example 19 except that (B) β-hydroxyalkylamide of Examples 2 to 18 was used instead of (B) β-hydroxyalkylamide synthesized in Example 1. A storage stability test was conducted.
比較例1
実施例1の(B)β−ヒドロキシアルキルアミドの代わりにDuranate TPA−100(旭化成社製のイソシアネート)を用いた以外は、実施例19と同様に試験を行った。
Comparative Example 1
The test was conducted in the same manner as in Example 19 except that Duranate TPA-100 (isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) β-hydroxyalkylamide in Example 1.
比較例2
実施例1の(B)β−ヒドロキシアルキルアミドの代わりにDuranate TPA−B80E(旭化成社製のブロックイソシアネート)を用いた以外は、実施例19と同様に試験を行った。
Comparative Example 2
The test was performed in the same manner as in Example 19 except that Duranate TPA-B80E (block isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) β-hydroxyalkylamide in Example 1.
比較例3
実施例1の(B)β−ヒドロキシアルキルアミドの代わりにEOCN−1020(日本化薬社製のエポキシ樹脂)を用いた以外は、実施例19と同様に試験を行った。
Comparative Example 3
The test was performed in the same manner as in Example 19 except that EOCN-1020 (epoxy resin manufactured by Nippon Kayaku Co., Ltd.) was used instead of (B) β-hydroxyalkylamide in Example 1.
比較例4
実施例1の(B)β−ヒドロキシアルキルアミドの代わりにEOCN−1020(日本化薬社製のエポキシ樹脂)を用い、さらに触媒としてN,N’−ジメチルベンジルアミンを使用した以外は、実施例19と同様に試験を行った。
Comparative Example 4
Example 1 except that EOCN-1020 (epoxy resin manufactured by Nippon Kayaku Co., Ltd.) was used instead of (B) β-hydroxyalkylamide in Example 1, and N, N′-dimethylbenzylamine was used as a catalyst. The test was conducted in the same manner as in 19.
比較例5
実施例1の(B)β−ヒドロキシアルキルアミドの代わりにPrimid XL−552(エムスケミー社製のβ−ヒドロキシアルキルアミド)を用いた以外は、実施例19と同様に試験を行った。
Comparative Example 5
The test was performed in the same manner as in Example 19 except that Primid XL-552 (β-hydroxyalkylamide manufactured by Ems Chemie) was used instead of (B) β-hydroxyalkylamide in Example 1.
比較例6
硬化試験(1)において、樹脂合成例1の(A)カルボン酸を有する樹脂の代わりに樹脂合成例3のヒドロキシ基を有する樹脂を用い、硬化試験(2)は行わなかった以外は、実施例19と同様に試験を行った。
Comparative Example 6
In the curing test (1), except that the resin having the hydroxy group of the resin synthesis example 3 was used instead of the resin having the carboxylic acid (A) of the resin synthesis example 1, and the curing test (2) was not performed, the examples The test was conducted in the same manner as in 19.
実施例19〜36、比較例1〜6を表1にまとめた。 Examples 19 to 36 and Comparative Examples 1 to 6 are summarized in Table 1.
表1
実施例19〜36は溶解性試験、硬化試験(1)、硬化試験(2)、保存安定性試験、すべてにおいて良好であった。 Examples 19 to 36 were good in all of the solubility test, the curing test (1), the curing test (2), and the storage stability test.
比較例1,2は硬化試験(2)で硬化しない結果であった。硬化試験(2)では沸点が高く(沸点:230.6℃)、ヒドロキシ基を有するブチルカルビトールを溶剤として使用しており、硬化温度(150℃)では十分に溶剤が揮発しない条件であるため、イソシアネートまたはブロックイソシアネートとブチルカルビトールが先に反応してしまい、樹脂のカルボキシ基と反応しなかったためと考えられる。このように、ヒドロキシ基を有する溶剤を使用する場合はイソシアネートまたはブロックイソシアネートを使用することができない。β−ヒドロキシアルキルアミドはヒドロキシ基とは反応せず、選択的にカルボキシ基と反応するため、ヒドロキシ基を有する溶剤を使用することが可能である。 Comparative Examples 1 and 2 were the results of not curing in the curing test (2). In the curing test (2), the boiling point is high (boiling point: 230.6 ° C.), butyl carbitol having a hydroxy group is used as a solvent, and the solvent does not volatilize sufficiently at the curing temperature (150 ° C.). This is probably because the isocyanate or blocked isocyanate and butyl carbitol reacted first and did not react with the carboxy group of the resin. Thus, when using the solvent which has a hydroxyl group, isocyanate or blocked isocyanate cannot be used. Since β-hydroxyalkylamide does not react with a hydroxy group but selectively reacts with a carboxy group, a solvent having a hydroxy group can be used.
比較例3、4はエポキシ基を有する架橋剤を使用した例である。比較例3は無触媒で硬化を行ったが、今回の試験条件では硬化しなかった。触媒を加えることで十分硬化することは確認できたが、その一方で、保存安定性試験で増粘する結果であった。エポキシ基は触媒を加えることで保存時に反応を抑えることができないが、β−ヒドロキシアルキルアミドであれば、保存時には反応せず、硬化条件では十分に反応させることができる。 Comparative Examples 3 and 4 are examples using a crosslinking agent having an epoxy group. Comparative Example 3 was cured without a catalyst, but did not cure under the present test conditions. Although it was confirmed that the catalyst was sufficiently cured by adding a catalyst, on the other hand, it was a result of thickening in a storage stability test. Epoxy groups cannot be suppressed during storage by adding a catalyst, but β-hydroxyalkylamide does not react during storage and can be sufficiently reacted under curing conditions.
比較例5は市販のβ−ヒドロキシアルキルアミドを使用した例であるが、溶剤に対する溶解性が乏しく、評価に至らなかった。 Comparative Example 5 is an example in which a commercially available β-hydroxyalkylamide was used, but the solubility in a solvent was poor, and evaluation was not achieved.
比較例6は樹脂の官能基をヒドロキシ基にしたものであるが、ヒドロキシ基とβ−ヒドロキシアルキルアミドは150℃では全く反応しないため、硬化することができない。 In Comparative Example 6, the functional group of the resin is a hydroxy group. However, the hydroxy group and β-hydroxyalkylamide do not react at 150 ° C. and cannot be cured.
以上のことから、本発明の(A)カルボン酸を有する樹脂と、(B)β−ヒドロキシアルキルアミドと、を含む樹脂組成物が溶剤溶解性、硬化性、保存安定性に優れていることがわかった。 From the above, the resin composition containing (A) the carboxylic acid-containing resin of the present invention and (B) β-hydroxyalkylamide is excellent in solvent solubility, curability and storage stability. all right.
本発明の化合物は、熱硬化性の印刷インキ、塗料、コーティング剤、粘接着剤、成形材料、光硬化性材料に使用することができる。 The compounds of the present invention can be used in thermosetting printing inks, paints, coating agents, adhesives, molding materials, and photocurable materials.
Claims (7)
一般式(1)
ここで、
Xは炭素、水素、酸素、窒素、硫黄、または、ハロゲンから構成されるn価の基であり、
脂環式炭化水素基、分岐脂肪族炭化水素基、芳香族炭化水素基、酸素、窒素、もしくは、硫黄で分断されている直鎖脂肪族炭化水素基、または、酸素、窒素、硫黄、もしくは、ハロゲンを含む置換基で置換された直鎖脂肪族炭化水素基であり、
X中のカルボニル基に直接結合する原子が炭素原子である。
nは2〜6の整数であり、
R1およびR2は、それぞれ独立に、水素原子、一般式(2)で表される基、または炭化水素基を表し、R1およびR2のうち、少なくとも1つは、一般式(2)で表される基である。
一般式(2)
ここで、R3〜R6はそれぞれ独立に、水素原子、炭化水素基、または、ヒドロキシ基で置換された炭化水素基のいずれかを表す。 (B) β-hydroxyalkylamide represented by the general formula (1).
General formula (1)
here,
X is an n-valent group composed of carbon, hydrogen, oxygen, nitrogen, sulfur, or halogen;
An alicyclic hydrocarbon group, a branched aliphatic hydrocarbon group, an aromatic hydrocarbon group, a linear aliphatic hydrocarbon group separated by oxygen, nitrogen, or sulfur, or oxygen, nitrogen, sulfur, or A linear aliphatic hydrocarbon group substituted with a halogen-containing substituent,
The atom directly bonded to the carbonyl group in X is a carbon atom.
n is an integer of 2-6,
R 1 and R 2 each independently represent a hydrogen atom, a group represented by the general formula (2), or a hydrocarbon group, and at least one of R 1 and R 2 is represented by the general formula (2) It is group represented by these.
General formula (2)
Here, R 3 to R 6 each independently represent a hydrogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a hydroxy group.
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