JPS63196610A - Manufacture of petroleum resin - Google Patents
Manufacture of petroleum resinInfo
- Publication number
- JPS63196610A JPS63196610A JP2814287A JP2814287A JPS63196610A JP S63196610 A JPS63196610 A JP S63196610A JP 2814287 A JP2814287 A JP 2814287A JP 2814287 A JP2814287 A JP 2814287A JP S63196610 A JPS63196610 A JP S63196610A
- Authority
- JP
- Japan
- Prior art keywords
- fraction
- petroleum
- petroleum resin
- less
- boiling point
- 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
Links
- 239000003208 petroleum Substances 0.000 title claims abstract description 34
- 239000011347 resin Substances 0.000 title claims abstract description 31
- 229920005989 resin Polymers 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000009835 boiling Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- COOKKJGOGWACMY-UHFFFAOYSA-N 3-methyl-1h-indene Chemical compound C1=CC=C2C(C)=CCC2=C1 COOKKJGOGWACMY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 5
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 3
- 238000004227 thermal cracking Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 210000003918 fraction a Anatomy 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VENBJVSTINLYEU-UHFFFAOYSA-N phenol;trifluoroborane Chemical compound FB(F)F.OC1=CC=CC=C1 VENBJVSTINLYEU-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は着色度の低い、すなわち淡色の石油樹脂を製造
する方法に関する。さらに詳しくは石油類の熱分解によ
り得られる各種留分のうち１４０〜２２０℃の範囲の沸
点を有する留分（以下これをＣ９留分と称する。）から
特定の成分を除去した成分をカチオン重合して淡色石油
樹脂を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing a petroleum resin with a low degree of coloration, that is, a light color. More specifically, a component obtained by removing a specific component from a fraction having a boiling point in the range of 140 to 220°C (hereinafter referred to as C9 fraction) among various fractions obtained by thermal decomposition of petroleum is subjected to cationic polymerization. The present invention relates to a method for producing a light-colored petroleum resin.
石油樹脂の品質のうち重要なものとして着色度合があシ
、良質な石油樹脂としては着色しないものが要求される
。特に高級用途分野、例えば粘着剤等では、殆ど無色の
樹脂が要求される程である。An important quality of petroleum resin is the degree of coloration, and high-quality petroleum resins are required to be free of coloration. Particularly in high-end applications, such as adhesives, almost colorless resins are required.
ところで、着色度の上限は、石油樹脂の用途にもよるが
、一般的にはガードナー色相（融解法）１０以下程度で
あシ、高級用途向では８以下程度である。石油樹脂は粘
着剤、トラフィックペイント、紙のサイズ剤等色相が重
視される製品の添加物として幅広い用途に用られている
が、石油樹脂の着色度が前述の上限以上になると最終製
品全体の色相を悪化させるため、着色しない石油樹脂が
要求されている。一方、石油樹脂の原料組成は極めて多
数の炭化水素化合物から構成されており、インデン、ビ
ニルトルエン等の有効成分の他に微量の着色成分も多い
ため、その石油樹脂は着色し易く、この問題の解決が非
常に重要である。By the way, the upper limit of the degree of coloring depends on the use of the petroleum resin, but generally it is about Gardner hue (melting method) about 10 or less, and for high-grade applications it is about 8 or less. Petroleum resins are used in a wide range of applications as additives in products where hue is important, such as adhesives, traffic paints, and paper sizing agents.However, if the degree of coloration of petroleum resins exceeds the above-mentioned upper limit, the hue of the entire final product will be affected. Therefore, non-colored petroleum resins are required. On the other hand, the raw material composition of petroleum resin is composed of an extremely large number of hydrocarbon compounds, and in addition to active ingredients such as indene and vinyltoluene, there are also many trace amounts of coloring components, so petroleum resin is easily colored, and this problem is solved. Resolution is very important.
〈従来の技術〉
ところで、淡色石油樹脂の製造方法については種々の方
法が提案されている。これらは、Ｃ９留分中にふくまれ
る微量の着色成分を予め除去、または重合活性の低い物
質に変換させる操作である。<Prior Art> Various methods have been proposed for producing light-colored petroleum resins. These are operations that remove in advance trace amounts of colored components contained in the C9 fraction or convert them into substances with low polymerization activity.
例えば、日化脇月報、１２月号、６８５（１９７５）に
記載されているように、Ｃ９留分中の不要成分、熱重合
物の除去のため、高沸点成分の除去を減圧下で行うこと
が知られている。また、特公昭５０−３４０７８には耐
候性樹脂の製造法として、Ｃ９留分中の共役ジオレフィ
ン含有量が０．９ｗｔ％以下で、共役ジオレフィンの含
有率が３％以下であり、かつインデン及びそのアルキル
誘導体の合計含有量が２ ｗｔ％以下でインデン含有率
が８％以下の条件に調整する方法が提案されている。For example, as described in Nikka Waki Monthly, December issue, 685 (1975), in order to remove unnecessary components and thermal polymers in the C9 fraction, high boiling point components are removed under reduced pressure. It has been known. In addition, Japanese Patent Publication No. 50-34078 describes a method for producing a weather-resistant resin in which the content of conjugated diolefin in the C9 fraction is 0.9 wt% or less, the content of conjugated diolefin is 3% or less, and A method has been proposed in which the total content of alkyl derivatives thereof is 2 wt% or less and the indene content is 8% or less.
また、特許５２−１３８３１には、Ｃ９留分を温和な条
件下でこれらの着色成分を前重合によυ高沸点物質に変
換し蒸留分離して、留出物をフリーデルクラフト型触媒
下で重合する方法が提案されている。In addition, Patent No. 52-13831 discloses that the C9 fraction is prepolymerized to convert these colored components into high-boiling substances by distillation under mild conditions, and the distillate is separated by distillation under a Friedel-Crafts type catalyst. A method of polymerization has been proposed.
その他、Ｐｋａ ３以下の酸性物質で処理した後１、
蒸留させたのち留出物を原料とする方法、及び振下飽
和留分中のインデン、ジシクロペンタジェン（シクロペ
ンタジェン）などを調整して重合するなど石油樹脂の淡
色化の方法が提案されている。In addition, after being treated with an acidic substance with a Pka of 3 or less,
Methods for lightening the color of petroleum resins have been proposed, such as using the distillate as a raw material after distillation, and adjusting and polymerizing indene, dicyclopentadiene (cyclopentadiene), etc. in the shaken saturated fraction. ing.
これらの方法は夫々に有効な方法ではあるが、前重合で
有害物を除去しようとする方法においては石油樹脂とし
て有効である成分をも同時に除去してしまうため収率が
低く経済的でない、あるいはプロセスが複雑となる欠点
を有する。一方蒸留で有効成分を得ようとする重合でも
指標とする物質の種類によっては必要以上に有効成分を
カットする結果、収率が過少になる欠点を有していた。Each of these methods is effective, but the method that attempts to remove harmful substances through prepolymerization simultaneously removes components that are effective as petroleum resins, resulting in low yields and being uneconomical. The disadvantage is that the process is complicated. On the other hand, polymerization in which the active ingredient is obtained by distillation has the disadvantage that depending on the type of substance used as an index, the active ingredient may be cut more than necessary, resulting in an insufficient yield.
く問題点を解決するための手段〉
上記欠点を解消すべく鋭意研究の結果、石油類の熱分解
によシ得られる分解油留分のうち１４０〜２２０℃の範
囲内の沸点留分から３−メチルインデンの含有率が４．
５％以下になる条件で高沸点成分を除去した留分を原料
としてカチオン重合を行ない、淡色石油樹脂を製造する
方法を発明するに至った。Means for Solving the Problems〉 As a result of intensive research in order to solve the above-mentioned shortcomings, we have found that 3- The content of methyl indene is 4.
The inventors have invented a method for producing a light-colored petroleum resin by carrying out cationic polymerization using the fraction from which high-boiling components have been removed under conditions of 5% or less as a raw material.
本発明の骨子は、着色原因物質は３−メチルインデンで
あり本物質を減少させることによシ石油樹脂が淡色化す
ることにある。The gist of the present invention is that the coloring substance is 3-methylindene, and by reducing this substance, the petroleum resin becomes lighter in color.
以下実施例をもって詳細に説明する。なお本実施例は特
許請求の範囲を限定するものではない。This will be explained in detail below using examples. Note that this example does not limit the scope of the claims.
なおガスクロマトグラフの分析条件は第１表に示す通ｐ
である。また樹脂の色相は、ＡＳＴＭＤ −１５４４−
８０に記載された方法に準じて、ガードナー法で測定し
た。The analysis conditions for the gas chromatograph are as shown in Table 1.
It is. In addition, the hue of the resin is ASTM D-1544-
It was measured by the Gardner method according to the method described in 80.
石油樹脂の試作は次のようにして行った。原料油に、０
．０１〜５ ｗｔ％の三フッ化ホウ素フェノール錯化合
物触媒を添加して、０〜２０℃の範囲内の温度で１時間
重合した後、カセイソーダで触媒を分解除去し、必要に
応じて、水洗し、更に、蒸留によシ未反応油及び低分子
量重合物を分離して、石油樹脂を得た。The petroleum resin prototype was produced as follows. In raw oil, 0
．． After adding 01 to 5 wt% of boron trifluoride phenol complex compound catalyst and polymerizing for 1 hour at a temperature within the range of 0 to 20°C, the catalyst was decomposed and removed with caustic soda, and if necessary, washed with water. Further, unreacted oil and low molecular weight polymers were separated by distillation to obtain a petroleum resin.
蒸留条件としては熱重合及び熱分解による有用成分の損
失を防ぐため、′！！−＝１１０ ｍｍ Ｈｇの塔圧で
蒸留した。The distillation conditions are '!' to prevent loss of useful components due to thermal polymerization and thermal decomposition. ! Distilled at a column pressure of -=110 mm Hg.
〈実施例〉
実施例１
ナフサのスチームクラッキングで副生する１５０〜２２
０℃のＣ９留分Ａは、第２表に示す組成を有する。この
Ｃ９留分Ａから、３−メチルインデンの含有量が０．５
９ｗｔ％となるように高沸点成分を蒸留で除去し、本発
明の原料油Ｂを得た。このとき蒸留塔としては段数２５
のものを用い、リフラックス比と塔圧を、夫々、１と７
０ ｔｍ Ｈｇに保って操作した。またこのときの原料
油Ｂの得率は原料油Ａの７０ ｗｔ％であった。<Example> Example 1 150-22 produced by steam cracking of naphtha
C9 fraction A at 0° C. has the composition shown in Table 2. From this C9 fraction A, the content of 3-methylindene is 0.5
The high-boiling components were removed by distillation to a concentration of 9 wt % to obtain raw material oil B of the present invention. At this time, the number of plates for the distillation column is 25.
The reflux ratio and tower pressure were set to 1 and 7, respectively.
The operation was maintained at 0 tm Hg. Further, the yield of feedstock B at this time was 70 wt% of feedstock A.
次にこの原料油Ｂに三フッ化ホウ素フェノール錯塩触媒
を０．８７ ｖｏｌ ％添加して、温度１０℃で１時間
重合した後、５ ｗｔ％カセイソーダ水溶液で触媒を分
解除去し、水洗し、更に、蒸留によ）未反応油及び低分
子量重合物を分離して石油樹脂を得た。この石油樹脂は
ガードナー色相（融解法）８の性状を示した。Next, 0.87 vol % of boron trifluoride phenol complex catalyst was added to this raw oil B, and after polymerization at a temperature of 10°C for 1 hour, the catalyst was decomposed and removed with a 5 wt % caustic soda aqueous solution, washed with water, and further , distillation) to separate unreacted oil and low molecular weight polymers to obtain a petroleum resin. This petroleum resin exhibited a Gardner hue (melting method) of 8.
比較例１
実施例１で使用したＣ９留分Ａの３−メチルインデンの
含有量は５．１８ｗｔ％である。これより、そのまま、
実施例１と同じ方法で石油樹脂を試作したところ、ガー
ドナー色相１２．５の性状の石油樹脂が得られた。Comparative Example 1 The content of 3-methylindene in C9 fraction A used in Example 1 was 5.18 wt%. From now on, as is,
When a petroleum resin was experimentally produced in the same manner as in Example 1, a petroleum resin having a Gardner hue of 12.5 was obtained.
実施例２
実施例１と同じ方法により、Ｃ９留分Ａから、３−メチ
ルインデンの含有量が３．７５ ｗｔｌとなるような組
成の原料油Ｃを得た。（表２参照）このときの原料油Ｃ
の得率は原料油Ａの８３ ｗｔｌであった。これよシ、
実施例１と同じ方法で石油樹脂を試作したところ、ガー
ドナー色相９，５の性状の石油樹脂が得られた。Example 2 Using the same method as in Example 1, raw oil C having a composition such that the content of 3-methylindene was 3.75 wtl was obtained from C9 fraction A. (See Table 2) Raw material oil C at this time
The yield of feedstock A was 83 wtl. This is it,
When a petroleum resin was experimentally produced in the same manner as in Example 1, a petroleum resin having a Gardner hue of 9.5 was obtained.
実施例３
実施例１と同じ方法によシ、Ｃ９留分Ａから、３−メチ
ルインデンの含有率が０ｗｔ％となるような組成の原料
油りを得た。（表２参照）このときの原料油りの得率は
原料油Ａの５５ ｗｔｌであった。Example 3 In the same manner as in Example 1, a raw material oil having a composition such that the content of 3-methylindene was 0 wt % was obtained from C9 fraction A. (See Table 2) The yield of raw material oil at this time was 55 wtl of raw material oil A.
これよシ、実施例１と同じ方法で石油樹脂を試作したと
ころ、ガードナー色相６．５の性状の石油樹脂が得られ
た。When a petroleum resin was experimentally produced in the same manner as in Example 1, a petroleum resin having a Gardner hue of 6.5 was obtained.
表１ ガスクロマトグラフ分析条件
カラム−−−０Ｖ−Ｉ Ｂｏｎｄ＠ｄ フ為−ズド
キヤピラリー長さ−−−−５０ｍ
内径−−−−０，２５禦 ２℃／分（昇温速
度）カラム温度−１００℃１０分保持−一一→２２０℃
２０分保持インジェク
シ、ン温度−１７０℃
検出器−−−Ｆ、１．Ｄ。Table 1 Gas chromatography analysis conditions Column---0V-I Bond@d Folded capillary length---50m Inner diameter---0.25mm 2℃/min (heating rate) Column temperature -100℃ Hold for 10 minutes - 11 → 220℃
Hold for 20 minutes Injector temperature -170°C Detector---F, 1. D.
Claims (1)
〜２２０℃の範囲内の沸点留分から３−メチルインデン
の含有量が４．５％以下になる条件で高沸点成分を除去
した留分を原料としてカチオン重合を行ない、淡色石油
樹脂を製造する方法。140 of the cracked oil fraction obtained by thermal decomposition of petroleum
A method for producing a light-colored petroleum resin by performing cationic polymerization using a boiling point fraction within the range of ~220°C, removing high boiling point components under conditions such that the content of 3-methylindene is 4.5% or less, as a raw material. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2814287A JPS63196610A (en) | 1987-02-12 | 1987-02-12 | Manufacture of petroleum resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2814287A JPS63196610A (en) | 1987-02-12 | 1987-02-12 | Manufacture of petroleum resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63196610A true JPS63196610A (en) | 1988-08-15 |
Family
ID=12240517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2814287A Pending JPS63196610A (en) | 1987-02-12 | 1987-02-12 | Manufacture of petroleum resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63196610A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573752A (en) * | 2022-03-11 | 2022-06-03 | 广东新华粤石化集团股份公司 | Modified petroleum resin with narrow molecular weight distribution, preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57202314A (en) * | 1981-06-08 | 1982-12-11 | Toyo Soda Mfg Co Ltd | Preparation of hydrocarbon resin |
-
1987
- 1987-02-12 JP JP2814287A patent/JPS63196610A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57202314A (en) * | 1981-06-08 | 1982-12-11 | Toyo Soda Mfg Co Ltd | Preparation of hydrocarbon resin |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573752A (en) * | 2022-03-11 | 2022-06-03 | 广东新华粤石化集团股份公司 | Modified petroleum resin with narrow molecular weight distribution, preparation method and application |
| CN114573752B (en) * | 2022-03-11 | 2023-11-03 | 广东新华粤石化集团股份公司 | Modified petroleum resin with narrow molecular weight distribution, preparation method and application |
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