JPH0524951B2 - - Google Patents
Info
- Publication number
- JPH0524951B2 JPH0524951B2 JP8469684A JP8469684A JPH0524951B2 JP H0524951 B2 JPH0524951 B2 JP H0524951B2 JP 8469684 A JP8469684 A JP 8469684A JP 8469684 A JP8469684 A JP 8469684A JP H0524951 B2 JPH0524951 B2 JP H0524951B2
- Authority
- JP
- Japan
- Prior art keywords
- tung oil
- catechol
- addition reaction
- reaction substance
- formula
- 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.)
- Expired - Lifetime
Links
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 24
- 239000002383 tung oil Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 9
- 238000007259 addition reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical group CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
Description
〔産業上の利用分野〕
本発明はフエノール樹脂およびエポキシ樹脂の
反応型可塑剤、酸化防止剤、漆の代替材等として
用いられる桐油とカテコールの付加反応物質及び
その製造法に関するものである。
〔従来技術〕
従来桐油とカテコールの反応については知られ
ていない。本発明者らは過去に桐油と１価のフエ
ノール類の反応について赤外吸収、核磁気共鳴、
液体クロマト等の機器分析等により基礎的反応解
析を行つた。その結果、
桐油の化学式は
で示されるが、フエノール類はフエノール核
のオルソ位あるいはパラ位で桐油の共役２重結
合に付加すること。
さらに詳細には桐油の１つのエレオステアリ
ン酸基に最大２モルのフエノール類が付加可能
なこと、すなわち桐油１モルに対しては最大６
モルのフエノール類が付加可能なこと。
桐油中の１個のエレオステアリン酸基（共役
トリエン１個含有）にフエノール類が１個しか
反応しない場合、未反応のジエンは活性化され
桐油同志の反応が進み重合物が生成すること等
の知見を得た。
〔発明の目的〕
本発明は新規な桐油とカテコールの付加反応物
質を得ることを目的とするもので、上記知見に基
き桐油とカテコールの反応について詳細に検討し
た結果なされたものである。
〔発明の構成〕
本発明は
〔ただし、３つの（−×−）のうち１つは次式の
(A)または(B)であり、他の２つは(A)、(B)、(C)の中か
ら組合せてあるいは重複して選ばれる。
(A)
[Industrial Field of Application] The present invention relates to an addition reaction substance of tung oil and catechol used as a reactive plasticizer for phenolic resins and epoxy resins, an antioxidant, a substitute for lacquer, etc., and a method for producing the same. [Prior Art] Conventionally, the reaction between tung oil and catechol has not been known. The present inventors have previously investigated the reaction between tung oil and monovalent phenols using infrared absorption, nuclear magnetic resonance, and
Basic reaction analysis was performed using instrumental analysis such as liquid chromatography. As a result, the chemical formula of tung oil is However, phenols are added to the conjugated double bond of tung oil at the ortho or para position of the phenol nucleus. More specifically, up to 2 moles of phenols can be added to one eleostearic acid group in tung oil, that is, up to 6 moles can be added to 1 mole of tung oil.
Capable of adding moles of phenols. If only one phenol reacts with one eleostearic acid group (containing one conjugated triene) in tung oil, the unreacted diene will be activated and the reaction between the tung oil will proceed and a polymer will be formed. We obtained the following knowledge. [Object of the Invention] The purpose of the present invention is to obtain a novel addition reaction substance between tung oil and catechol, and was achieved as a result of detailed study on the reaction between tung oil and catechol based on the above findings. [Structure of the invention] The present invention [However, one of the three (-×-) is
(A) or (B), and the other two are selected from (A), (B), and (C) in combination or in duplicate. (A)
【式】 (B)【formula】 (B)
本発明により新規な桐油とカテコールの付加反
応物質が得られた。
According to the present invention, a novel addition reaction substance of tung oil and catechol was obtained.
第１図、第２図、第３図はそれぞれ実施例１で
得られた化合物の液体クロマト、核磁気共鳴、赤
外分光チヤートで、第４図はこれをメチルアルコ
ールによりエステル分解した分解物の液体クロマ
トチヤートである。第５図、第６図、第７図はそ
れぞれ実施例２で得られた化合物の液体クロマ
ト、核磁気共鳴、赤外分光チヤートで、第８図は
これをメルチアルコールによりエステル分解した
分解物の液体クロマトチヤートである。
Figures 1, 2, and 3 are liquid chromatography, nuclear magnetic resonance, and infrared spectroscopy charts of the compound obtained in Example 1, respectively, and Figure 4 shows the decomposition product obtained by deesterifying the compound with methyl alcohol. It is a liquid chromatograph. Figures 5, 6, and 7 are liquid chromatography, nuclear magnetic resonance, and infrared spectroscopy charts of the compound obtained in Example 2, respectively, and Figure 8 shows the decomposition product obtained by ester decomposition of this with merthyl alcohol. It is a liquid chromatograph.
Claims (1)
または(B)であり他の２つは(A)、(B)、(C)の中から組
合せてあるいは重複して選ばれる。 (A)【式】 (B)【式】 (C) −CH＝CH−CH＝CH−CH＝CH−〕 なる化学式で示される桐油とカテコールの付加反
応物質。 ２ ×が２つ(A)で１つ(C)である特許請求の範囲第
１項記載の桐油とカテコールの付加反応物質。 ３ ×が３つとも(B)である特許請求の範囲第１項
記載の桐油とカテコールの付加反応物質。 ４ 反応溶剤に溶解させたカテコールに桐油を添
加しフリーデルクラフト触媒の存在下で反応させ
ることを特徴とする桐油とカテコールの付加反応
物質の製造法。 ５ 桐油がカテコール１モルに対して1/10〜1/20
０モルである特許請求の範囲第４項記載の桐油と
カテコールの付加反応物質の製造法。[Claims] 1 [However, one of the three (-×-) is (A) in the following equation
or (B), and the other two are selected from (A), (B), and (C) in combination or in duplicate. (A) [Formula] (B) [Formula] (C) -CH=CH-CH=CH-CH=CH-] An addition reaction substance of tung oil and catechol, represented by the chemical formula. The addition reaction material of tung oil and catechol according to claim 1, wherein 2 x is two (A) and one (C). 3. The addition reaction substance of tung oil and catechol according to claim 1, wherein all three x's are (B). 4. A method for producing an addition reaction substance of tung oil and catechol, which comprises adding tung oil to catechol dissolved in a reaction solvent and reacting the mixture in the presence of a Friedel-Crafts catalyst. 5 Tung oil is 1/10 to 1/20 per mole of catechol
A method for producing an addition reaction substance of tung oil and catechol according to claim 4, wherein the amount is 0 mol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8469684A JPS60228580A (en) | 1984-04-26 | 1984-04-26 | Addition reaction product between tung oil and catechol and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8469684A JPS60228580A (en) | 1984-04-26 | 1984-04-26 | Addition reaction product between tung oil and catechol and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60228580A JPS60228580A (en) | 1985-11-13 |
| JPH0524951B2 true JPH0524951B2 (en) | 1993-04-09 |
Family
ID=13837825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8469684A Granted JPS60228580A (en) | 1984-04-26 | 1984-04-26 | Addition reaction product between tung oil and catechol and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60228580A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105237720B (en) * | 2015-11-02 | 2017-11-10 | 华南农业大学 | Containing the double UV curing groups PUA prepolymers of double bond/phenolic hydroxyl group and preparation method and application |
| CN105906586A (en) * | 2016-05-12 | 2016-08-31 | 中国林业科学研究院林产化学工业研究所 | Epoxy grease base plasticizing agent and preparation method thereof |
| CN106397367A (en) * | 2016-08-29 | 2017-02-15 | 中国林业科学研究院林产化学工业研究所 | Tung oil source epoxy plasticizer product having function of heat stabilizer, preparation method thereof and application thereof |
-
1984
- 1984-04-26 JP JP8469684A patent/JPS60228580A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60228580A (en) | 1985-11-13 |
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