JPH0435903A - Manufacture of acylated woody material - Google Patents
Manufacture of acylated woody materialInfo
- Publication number
- JPH0435903A JPH0435903A JP14412390A JP14412390A JPH0435903A JP H0435903 A JPH0435903 A JP H0435903A JP 14412390 A JP14412390 A JP 14412390A JP 14412390 A JP14412390 A JP 14412390A JP H0435903 A JPH0435903 A JP H0435903A
- Authority
- JP
- Japan
- Prior art keywords
- wood
- ketene
- acylated
- acylating
- wood material
- 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
- 239000000463 material Substances 0.000 title claims abstract description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002023 wood Substances 0.000 claims abstract description 97
- 150000002561 ketenes Chemical class 0.000 claims description 7
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ketene group Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract description 41
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 239000003054 catalyst Substances 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- RZGZTQYTDRQOEY-UHFFFAOYSA-N 2-phenylethenone Chemical compound O=C=CC1=CC=CC=C1 RZGZTQYTDRQOEY-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002421 anti-septic effect Effects 0.000 abstract description 2
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
- 238000005917 acylation reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 241000218645 Cedrus Species 0.000 description 13
- 239000007789 gas Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 230000010933 acylation Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000021736 acetylation Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000013555 soy sauce Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- -1 fatty acid salts Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100305924 Caenorhabditis elegans hoe-1 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、木質材を改質処理したアシル化木質材の製造
方法に関する。さらに詳しくは木質材中の水酸基をエス
テル化することにより、耐汚染性、寸法安定性および防
腐性を改良したアシル化木質材の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing an acylated wood material obtained by modifying a wood material. More specifically, the present invention relates to a method for producing an acylated wood material with improved stain resistance, dimensional stability, and antiseptic properties by esterifying hydroxyl groups in the wood material.
［従来の技術と発明が解決しようとする課題］木材、木
材単板、木材チップ等の木質材は、建築材料、家具用材
料その他の広範な用途に利用されているが、各種微生物
、白蟻等の虫害により浸蝕や腐敗が生し、老朽化しやす
いという問題を有している。[Prior art and problems to be solved by the invention] Wood materials such as wood, wood veneers, and wood chips are used for a wide range of purposes such as building materials and furniture materials, but they are susceptible to various microorganisms, termites, etc. They suffer from erosion and rot due to insect damage, and are susceptible to deterioration.
また、木質材はその主成分、特にセルロースか多数の水
酸基を有しているため、大気中の水分を吸収して、カビ
等が発生しやすい環境となり、発生したカビ等により、
耐久性が低下する。さらに、木質材は雰囲気の湿度に応
して水分を吸収、放出して伸縮するので、寸法安定性が
劣る。また、親水性および浸透性が高いので、液状物で
汚染されやすいという問題もある。In addition, since wood has a large number of hydroxyl groups in its main components, especially cellulose, it absorbs moisture from the atmosphere, creating an environment where mold and other molds can easily grow.
Durability decreases. Furthermore, wood materials absorb and release moisture depending on the humidity of the atmosphere and expand and contract, resulting in poor dimensional stability. Furthermore, since it has high hydrophilicity and permeability, there is also the problem that it is easily contaminated with liquid substances.
このような問題を解決する手段として、木質材中の水酸
基をエステル化する方法が提案されている。例えば、特
開昭５８−１８１６０４号公報には、木質材に肪酸酸塩
水溶液からなるアシル化触媒を含浸させて乾燥した後、
木質材を脂肪酸無水物で処理してアシル化する方法が開
示され、特開昭５９−２０９１０３号公報には、木質材
に酢酸塩水溶液を含浸させて乾燥した後、無水酢酸と有
機溶媒とからなる混合液で処理して、木質材をアシル化
する方法か開示されている。このような方法に従って、
木質材中の水酸基をエステル化することにより木質材の
親油性を増大させ、木質材の大気中の水分吸収量を低下
させることができる。As a means to solve these problems, a method of esterifying the hydroxyl groups in wood materials has been proposed. For example, Japanese Patent Application Laid-Open No. 58-181604 discloses that after impregnating a wooden material with an acylation catalyst consisting of an aqueous fatty acid salt solution and drying it,
A method of acylating wood by treating it with a fatty acid anhydride is disclosed, and Japanese Patent Application Laid-Open No. 59-209103 discloses a method of acylating wood by impregnating it with an acetate aqueous solution, drying it, and then treating it with acetic anhydride and an organic solvent. A method for acylating wood materials by treating them with a mixed solution is disclosed. Following this method,
By esterifying the hydroxyl groups in the wood material, the lipophilicity of the wood material can be increased and the amount of moisture absorbed by the wood material in the atmosphere can be reduced.
そして、木質材をアシル化するアシル化剤としては、反
応性、余剰の反応液や触媒等の除去の簡便さの点から、
一般に、無水酢酸、脂肪酸塩等か用いられている（前記
公報、雑誌「工業材料Ｊ第３４巻、５号、１０１〜１０
５頁、雑誌「木材学会誌」第３２巻、１０号、７５５〜
７６２頁）。As an acylating agent for acylating wood materials, from the viewpoint of reactivity and ease of removing excess reaction liquid and catalyst, etc.
Generally, acetic anhydride, fatty acid salts, etc. are used (the above publication, the magazine "Industrial Materials J Vol. 34, No. 5, 101-10
Page 5, Journal of the Japan Society of Wood Science, Vol. 32, No. 10, 755~
762 pages).
しかしながら、木質材は複雑な構成成分を有しており、
無水酢酸；酢酸ナトリウム、酢酸カリウム等の脂肪酸塩
等のアシル化剤を用いる方法では、木質材中の水酸基に
対する反応性が低く、アシル化に長時間要し、アシル化
木質材の生産性が低い。However, wood has a complex composition,
Acetic anhydride: Methods using acylating agents such as fatty acid salts such as sodium acetate and potassium acetate have low reactivity to hydroxyl groups in wood, require a long time for acylation, and have low productivity of acylated wood. .
また、上記無水酢酸などを用いた場合、アシル化反応で
酢酸か副生ずるため、木質材に酢酸臭が残り、後処理に
より酢酸を除去する必要があった。Further, when the above-mentioned acetic anhydride is used, acetic acid is produced as a by-product in the acylation reaction, so that an acetic acid odor remains in the wood, and it is necessary to remove acetic acid by post-treatment.
［課題を解決するための手段］
本発明者等は、かかる問題を解決すべく鋭意検討を重ね
た結果、上記アシル化剤よりも反応性か高いケテン類を
用いると、効率よく木質材中の水酸基をエステル化でき
、しかも酢酸臭が残存しないことを見出し、本発明の完
成に至った。[Means for Solving the Problems] As a result of intensive studies to solve these problems, the present inventors found that using ketenes, which have higher reactivity than the above-mentioned acylating agents, can efficiently reduce the amount of wood in wood materials. It was discovered that hydroxyl groups can be esterified and no acetic acid odor remains, leading to the completion of the present invention.
すなわち、本発明のアシル化木質材の製造方法は、木質
材をケテン類でアシル化することを特徴とする。That is, the method for producing an acylated wood material of the present invention is characterized by acylating the wood material with a ketene.
本明細書において、木質材をアシル化するとは、木質材
中の水酸基の水素原子をアシル基で置換することを意味
する。As used herein, to acylate a wood material means to substitute a hydrogen atom of a hydroxyl group in the wood material with an acyl group.
本発明に用いることができる木質材には、例えば、木材
原木、丸太材、製材された板材、角材、木材チップ、経
木（木材薄シート）等の木材及びこれらの切屑であるお
が屑などが含まれる。これらの木質材は、そのままアシ
ル化反応に供してもよいか、アシル化反応の前に、木質
材を乾燥するのが好ましい。例えば、ドライヤー等の乾
燥機を用いて木質材中の水分量が１０％以下になるよう
に乾燥すると、その後のアシル化反応がさらに円滑に進
行する。Wood materials that can be used in the present invention include, for example, wood logs, logs, sawn boards, square lumber, wood chips, wood such as wood (thin sheets of wood), and sawdust that is the chips of these wood materials. . These wood materials may be subjected to the acylation reaction as they are, or it is preferable to dry the wood materials before the acylation reaction. For example, if the wood material is dried using a dryer such as a dryer so that the moisture content in the wood material is 10% or less, the subsequent acylation reaction will proceed more smoothly.
ケテン類には、例えばケテン、メチルケテン、フェニル
ケテン、ジメチルケテンなどが含まれる。Examples of ketenes include ketene, methylketene, phenylketene, dimethylketene, and the like.
好ましくは常温で気体状態のケテン類が用いられる。特
に好ましくは、反応性か高いケテンか用いられる。ケテ
ン類は木質材中のセルロース等に含まれる水酸基とのエ
ステル化反応性か、酢酸や無水酢酸よりも高い。Preferably, ketenes in a gaseous state at room temperature are used. Particularly preferably, highly reactive ketenes are used. Ketenes have a higher esterification reactivity than acetic acid and acetic anhydride, probably due to their esterification reactivity with hydroxyl groups contained in cellulose in wood materials.
以下、特に断わりのない限り、上記ケテン類を単にケテ
ンと総称する。Hereinafter, unless otherwise specified, the above ketenes will be collectively referred to simply as ketene.
木質材のアシル化反応条件は、ケテンで処理する限り特
に制限はないが、一般には、例えば−５０〜１５０℃程
度、０．０１〜２０気圧程度の条件下で、０．１〜９６
時間程度行えばよい。ケテンは反応性か高いので、短時
間でしかも比較的低い温度で木質材をアシル化すること
ができる。また、アシル化反応は、触媒、例えば硫酸等
の酸性触媒の存在下で行なってもよい。The acylation reaction conditions for wood materials are not particularly limited as long as they are treated with ketene, but generally, for example, at about -50 to 150°C, at about 0.01 to 20 atm, and at 0.1 to 96
It only takes about an hour. Because ketene is highly reactive, it can acylate wood materials in a short time and at relatively low temperatures. The acylation reaction may also be carried out in the presence of a catalyst, for example an acidic catalyst such as sulfuric acid.
ケテンを用いて木質材をアシル化する方法としては、例
えば下記の３種類の方法が挙げられる。Examples of methods for acylating wood materials using ketene include the following three methods.
（１）常温て気体状態のケテンの雰囲気中で木質材をア
シル化する方法
（２）加圧により液体状態となったケテン、または常温
で液体状態のケテンの液中に木質材を浸漬して木質材を
アシル化する方法
（３）不活性溶媒を含浸した木質材を収容する反応系内
、あるいは不活性溶媒中に木質材を浸漬した反応系内に
、ケテンガスを供給して木質材をアシル化する方法
（１）の方法は、木質材を入れた反応容器内を脱気減圧
した後、この容器内にケテンガスを導入して、木質材を
アシル化する方法である。この方法において、ケテンガ
スを単独で用いてもよいし、ケテンガスと乾燥窒素等の
不活性気体との混合気体を用いてもよい。ケテンガスと
不活性気体との混合気体を用いる場合、ケテンの濃度を
、例えば８０％以下に稀釈してもよい。ケテンの濃度を
８０％以下にすると、アシル化処理におけるコストか低
下する、また、ケテンの濃度を調整することにより、ア
シル化反応およびアシル化度の制御か容易となる。(1) A method of acylating wood in an atmosphere of ketene, which is in a gaseous state at room temperature. (2) Method of acylating wood material in an atmosphere of ketene, which is in a gaseous state at room temperature. Method for acylating wood materials (3) Acetylation of wood materials by supplying ketene gas into a reaction system containing wood materials impregnated with an inert solvent, or into a reaction system containing wood materials immersed in an inert solvent. Method (1) is a method in which the interior of a reaction vessel containing a wood material is degassed and depressurized, and then ketene gas is introduced into the container to acylate the wood material. In this method, ketene gas may be used alone, or a mixed gas of ketene gas and an inert gas such as dry nitrogen may be used. When using a mixed gas of ketene gas and inert gas, the concentration of ketene may be diluted to, for example, 80% or less. When the concentration of ketene is 80% or less, the cost of the acylation process is reduced, and by adjusting the concentration of ketene, the acylation reaction and the degree of acylation can be easily controlled.
（１）の方法は、少なくともケテンガスを含む雰囲気中
で木質材をアシル化するので、比較的表面積か大きな木
質材であっても効率よくアシル化処理てきる。また、既
に組立てられた木工製品についても、組立状態でアシル
化処理することができるので、木質材の少なくとも表層
部全体を処理できる。Method (1) acylates wood in an atmosphere containing at least ketene gas, so even wood with a relatively large surface area can be efficiently acylated. In addition, since it is possible to acylate an already assembled wood product in the assembled state, at least the entire surface layer of the wood material can be treated.
（２）の方法において、常温で気体状態のケテンを用い
る場合には、まず木質材を収容するオートクレーブ等の
反応容器にケテンをいれ、これを加圧してケテンを液体
状態にして、木質材をアシル化するのが好ましい。この
場合、加圧によりケテンが木質材の内部にまで浸透する
ので、木質材の内部も均一にアシル化できる。In method (2), when using ketene that is in a gaseous state at room temperature, first put ketene into a reaction vessel such as an autoclave containing the wood material, pressurize it to make the ketene into a liquid state, and then release the wood material into a liquid state. Acylation is preferred. In this case, ketene penetrates into the interior of the wood material due to pressurization, so that the interior of the wood material can also be uniformly acylated.
一方、常温で液体状態のケテンを用いる場合には、液状
ケテンを容器に仕込み、二〇ケテン液中に木質材を浸漬
してアシル化する。常温で液体状態であるケテンを用い
る場合には、加圧は特に必要ではないが、加圧すること
が好ましい。加圧によりケテンを木質材の内部にまで浸
透させ、木質材の内部もアシル化できる。On the other hand, when using ketene that is in a liquid state at room temperature, the liquid ketene is placed in a container and the wood is acylated by immersing it in the 20-ketene solution. When using ketene which is in a liquid state at room temperature, pressurization is not particularly necessary, but it is preferable to pressurize. By applying pressure, ketene penetrates into the interior of the wood material, and the interior of the wood material can also be acylated.
（３）の方法は、不活性溶媒を利用して木質材をアシル
化する方法である。不活性溶媒としては、例えば、水酸
基やアミノ基等の活性水素を含まない有機溶剤が用いら
れる。このような有機溶剤には、例えば、トルエン、キ
シレン等の芳香族系溶剤；ヘキサン等の脂肪族系溶剤；
シクロヘキサン等の脂環族系溶剤等が含まれる。Method (3) is a method of acylating wood material using an inert solvent. As the inert solvent, for example, an organic solvent containing no active hydrogen such as a hydroxyl group or an amino group is used. Such organic solvents include, for example, aromatic solvents such as toluene and xylene; aliphatic solvents such as hexane;
Includes alicyclic solvents such as cyclohexane.
このような不活性溶媒を含浸した木質材を収容する容器
内に、ケテンガスを供給して木質材をアシル化する。あ
るいは上記溶媒中に木質材を浸漬し、容器内または溶媒
中に直接ケテンガスを供給して木質材をアシル化する。Ketene gas is supplied into a container containing a wood material impregnated with such an inert solvent to acylate the wood material. Alternatively, a wood material is immersed in the above solvent, and ketene gas is supplied into the container or directly into the solvent to acylate the wood material.
いずれの場合も、ケテンが溶媒とともに木質材の内部に
まで浸透し、木質材の内部までアシル化処理することが
できる。In either case, ketene penetrates into the interior of the wood material together with the solvent, allowing the acylation treatment to reach the interior of the wood material.
（１）〜（３）の方法において、木質材を収容する反応
容器内を減圧にすると、木質材内部まで脱気することが
できるので、その後、ケテンを導入すると、木質材の内
部にまでケテンを浸透させ、アシル化処理できる。また
、（１）および（３）の方法において、オートクレーブ
等の反応容器を用いて、加圧条件にてアシル化処理をす
ると、木質材の内部までアシル化処理することかできる
ので好ましい。In methods (1) to (3), if the pressure inside the reaction vessel containing the wood material is reduced, the inside of the wood material can be degassed, so if ketene is then introduced, the ketene will reach the inside of the wood material. can be infiltrated and acylated. Furthermore, in methods (1) and (3), it is preferable to carry out the acylation treatment under pressurized conditions using a reaction vessel such as an autoclave, since the acylation treatment can be carried out to the inside of the wood material.
このようにして製造されたアシル化木質材は、単独で用
いてもよいし、合板等に加工して建築材、土木用素材、
構築材、家具材等の用途に使用してもよい。木材をアシ
ル化すると、親油性が増加するので、接着剤により接着
強度の大きな合板などの加工品を得ることができる。同
様に、アシル化したおが屑は樹脂との親和性に優れてい
るので樹脂加工品の材料に適する。The acylated wood material produced in this way may be used alone or processed into plywood etc. for construction materials, civil engineering materials, etc.
It may be used for construction materials, furniture materials, etc. When wood is acylated, its lipophilicity increases, so it is possible to obtain processed products such as plywood with high adhesive strength using adhesives. Similarly, acylated sawdust has excellent affinity with resins and is therefore suitable as a material for resin-processed products.
［発明の効果］
本発明のアシル化木質材の製造方法は、反応性が高いケ
テンを用いるので、反応が速く、木質材のアシル化反応
を短時間に効率的に行うことができる。さらに酢酸のよ
うな副生物が生成しないので、生産コストを大幅に低下
することができる。[Effects of the Invention] Since the method for producing an acylated wood material of the present invention uses highly reactive ketene, the reaction is fast and the acylation reaction of the wood material can be efficiently carried out in a short time. Furthermore, since by-products such as acetic acid are not produced, production costs can be significantly reduced.
［実施例］
以下に、実施例に基づいて本発明をより詳細に説明する
。[Examples] The present invention will be described in more detail below based on Examples.
実施例１
厚みが０．１順で、１０ｃｍＸ１５ｃｍの杉材の経本を
ガラス製耐圧容器に入れて、１００ 關Ｈｇまて減圧脱
気した後、容器内にケテンを導入して常圧に戻し、２０
℃で１時間、反応させた。反応後、容器内のケテンを空
気で置換して、アセチル化処理した経本を取り出した。Example 1 A 10 cm x 15 cm cedar textbook with a thickness of 0.1 cm was placed in a glass pressure container, degassed under reduced pressure at 100 Hg, and then ketene was introduced into the container to return the pressure to normal pressure. , 20
The reaction was allowed to proceed at ℃ for 1 hour. After the reaction, the ketene in the container was replaced with air, and the acetylated scriptures were taken out.
アセチル化処理した経本からは、ケテン臭、酢酸臭のい
ずれも感じられなかった。Neither ketene odor nor acetic acid odor was detected from the acetylated scriptures.
アセチル化処理した経本の重量を測定したところ、アセ
チル化による重量増加率は２０％であった。また、アセ
チル化処理した経本を、３７℃、相対湿度９０％の空気
中に６０日間放置後、その表面を観察したところ、アセ
チル化処理した軽水の表面には、カビの発生はなく、腐
蝕もしていなかった。When the weight of the acetylated textbook was measured, the weight increase rate due to acetylation was 20%. Furthermore, when we observed the surface of the acetylated scriptures after leaving them in the air at 37°C and 90% relative humidity for 60 days, we found that there was no mold growth on the surface of the acetylated light water, and there was no corrosion. I didn't even do it.
比較例１
実施例１て用いた杉材と同質同大の軽水を、アセチル化
することなく、実施例］と同様の条件（３７℃、相対湿
度９０％の空気中に６０日間）で放置したところ、経本
には、カビが発生し、経本の一部分は明らかに腐蝕して
いた。Comparative Example 1 Light water of the same quality and size as the cedar wood used in Example 1 was left under the same conditions as in Example (60 days in air at 37°C and 90% relative humidity) without being acetylated. However, mold had grown on the sutra, and some parts of the sutra were clearly corroded.
実施例２
厚みが５龍で、５ｃｍＸ１０ｃｍの杉材を５ｇのガラス
製耐圧容器に入れて１００ｗＨｇまて減圧脱気した後、
容器内にトルエンを仕込んだ。この容器に空気を導入し
て常圧に戻した後、反応系内にケテンガスを２０ｍ１／
分の速度で６０分間供給した。Example 2 A 5 cm x 10 cm cedar wood with a thickness of 5 cm was placed in a 5 g glass pressure container and degassed under reduced pressure to 100 wHg.
Toluene was charged into the container. After introducing air into this container and returning it to normal pressure, ketene gas was introduced into the reaction system at 20ml/ml.
It was fed for 60 minutes at a rate of 1 minute.
次に、容器内のトルエンを除去し、アセチル化処理した
杉材を取出して、杉材の重量を測定したところ、アセチ
ル化処理による杉材の重量増加率は２２％であった。Next, the toluene in the container was removed, the acetylated cedar wood was taken out, and the weight of the cedar wood was measured. The weight increase rate of the cedar wood due to the acetylation treatment was 22%.
得られた、このアセチル化処理した杉材を、下記の（ａ
）〜（Ｃ）雰囲気中で７日間放置した。The resulting acetylated cedar wood was processed into the following (a)
) to (C) left in an atmosphere for 7 days.
（ａ） ５０℃、相対湿度９０％
（ｂ） ５０℃、相対湿度３０％
（ｃ） −５℃、相対湿度９０％
放置後、６０℃の温風乾燥器で２４時間乾燥して、アセ
チル化処理した杉材の寸法を測定したところ、杉材の寸
法変化率の平均値は０．３％であった。(a) 50°C, 90% relative humidity (b) 50°C, 30% relative humidity (c) -5°C, 90% relative humidity After standing, dry in a hot air dryer at 60°C for 24 hours to acetylate. When the dimensions of the treated cedar wood were measured, the average value of the dimensional change rate of the cedar wood was 0.3%.
比較例２
実施例２て用いた杉材と同質同大の杉材を、アセチル化
することなく、実施例２と同様に、（ａ）〜（Ｃ）の各
条件で放置し、乾燥して、杉材の寸法を測定したところ
、杉材の寸法変化率の平均値は３．１％であった。Comparative Example 2 Cedar wood of the same quality and size as the cedar wood used in Example 2 was left to dry under the conditions (a) to (C) in the same manner as in Example 2 without being acetylated. When the dimensions of the cedar wood were measured, the average value of the dimensional change rate of the cedar wood was 3.1%.
実施例３
ラワン材のおが屑１００ｇを５ｇのガラス製耐圧容器に
入れて１００關Ｈｇまて減圧脱気した後、これにトルエ
ンを仕込んだ。容器内に空気を導入して常圧に戻した後
、反応系内にケテンガスを２０ ｍｌ ／分の速度で６
０分間供給して、アセチル化反応させた。Example 3 100 g of lauan sawdust was placed in a 5 g glass pressure-resistant container, degassed under reduced pressure of 100 Hg, and then toluene was charged therein. After introducing air into the container and returning it to normal pressure, ketene gas was introduced into the reaction system at a rate of 20 ml/min.
The mixture was supplied for 0 minutes to cause an acetylation reaction.
反応後、トルエンを除去し、アセチル化処理したラワン
材のおが屑を取出して、その重量を測定したところ、ア
セチル化処理によるラワン材のおが屑の重量増加率は１
８％であった。After the reaction, the toluene was removed, the acetylated sawdust from the lauan wood was taken out, and its weight was measured.The weight increase rate of the sawdust from the lauan wood due to the acetylation process was 1.
It was 8%.
このアセチル化処理したラワン材のおが屑を用いた成形
品を得るために、このおが屑５０ｇと、接着剤としての
ポリ酢酸ビニル系エマルジョン（ダイセル化学工業■製
、商品名セビアンーＡ５６８）１００ｇとを混合し、こ
の混合物をカラス板に流延して乾燥した。乾燥後、おが
屑を含む成形品を切出して、厚さ２關、５ ｃ＋ｎ Ｘ
５ ｃｍの試験片を得た。In order to obtain a molded product using this acetylated lauan wood sawdust, 50 g of this sawdust was mixed with 100 g of a polyvinyl acetate emulsion (manufactured by Daicel Chemical Industries, Ltd., trade name: SEVIAN-A568) as an adhesive. This mixture was cast onto a glass plate and dried. After drying, cut out the molded product containing sawdust to a thickness of 2 cm, 5 c+n
A 5 cm test piece was obtained.
この試験片にしょう油を１滴落し、３時間後にふき取っ
た後、試験片の表面状態を観察したところ、成形品の表
面には、しょう油の跡か見られず、耐汚染性に優れてい
た。One drop of soy sauce was placed on this test piece, and after 3 hours it was wiped off. When the surface condition of the test piece was observed, no traces of soy sauce were seen on the surface of the molded product, and it was found to have excellent stain resistance.
比較例３
ラワン材のおが屑５０ｇをアセチル化することなく、実
施例３と同様にしておが屑成形品を得た。Comparative Example 3 A sawdust molded product was obtained in the same manner as in Example 3 without acetylating 50 g of lauan sawdust.
このおが屑成形品の試験片を作製した。この試験片につ
いて実施例３と同様に試験したところ、試験片の表面に
はしょう油の跡か残っていた。A test piece of this sawdust molded product was prepared. When this test piece was tested in the same manner as in Example 3, traces of soy sauce remained on the surface of the test piece.
特許出願人 ダイセル化学工業株式会社代 理
人 弁理士 鍬 １） 充 生−１′／Patent applicant Daicel Chemical Industries, Ltd. Representative
Person Patent Attorney Hoe 1) Mitsuru Life-1'/
Claims (1)
シル化木質材の製造方法。A method for producing acylated wood material, which comprises acylating wood material with ketenes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14412390A JPH0435903A (en) | 1990-05-31 | 1990-05-31 | Manufacture of acylated woody material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14412390A JPH0435903A (en) | 1990-05-31 | 1990-05-31 | Manufacture of acylated woody material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0435903A true JPH0435903A (en) | 1992-02-06 |
Family
ID=15354732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14412390A Pending JPH0435903A (en) | 1990-05-31 | 1990-05-31 | Manufacture of acylated woody material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0435903A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0669456A (en) * | 1989-04-10 | 1994-03-11 | Seiko Epson Corp | Memory cell |
| JPH0677435A (en) * | 1992-02-24 | 1994-03-18 | Seiko Epson Corp | Semiconductor device |
| DE102009027635A1 (en) | 2009-07-10 | 2011-01-13 | Wacker Chemie Ag | Process for the acetylation of lignocelluloses, hemicelluloses, celluloses with ketene |
| CN106827150A (en) * | 2016-12-28 | 2017-06-13 | 重庆市锋跃建材有限公司 | Building template manufacture craft |
-
1990
- 1990-05-31 JP JP14412390A patent/JPH0435903A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0669456A (en) * | 1989-04-10 | 1994-03-11 | Seiko Epson Corp | Memory cell |
| JPH0732202B2 (en) * | 1989-04-10 | 1995-04-10 | セイコーエプソン株式会社 | Memory cell |
| JPH0677435A (en) * | 1992-02-24 | 1994-03-18 | Seiko Epson Corp | Semiconductor device |
| JPH0732201B2 (en) * | 1992-02-24 | 1995-04-10 | セイコーエプソン株式会社 | Semiconductor device |
| DE102009027635A1 (en) | 2009-07-10 | 2011-01-13 | Wacker Chemie Ag | Process for the acetylation of lignocelluloses, hemicelluloses, celluloses with ketene |
| EP2287203A1 (en) | 2009-07-10 | 2011-02-23 | Wacker Chemie AG | Process for the acetylation of lignocelluloses, hemicelluloses, celluloses with ketene |
| CN106827150A (en) * | 2016-12-28 | 2017-06-13 | 重庆市锋跃建材有限公司 | Building template manufacture craft |
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