JP2019119678A - 水溶性金属加工油剤用防黴剤及びそれを含有する水溶性金属加工油剤組成物 - Google Patents
水溶性金属加工油剤用防黴剤及びそれを含有する水溶性金属加工油剤組成物 Download PDFInfo
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- JP2019119678A JP2019119678A JP2017253067A JP2017253067A JP2019119678A JP 2019119678 A JP2019119678 A JP 2019119678A JP 2017253067 A JP2017253067 A JP 2017253067A JP 2017253067 A JP2017253067 A JP 2017253067A JP 2019119678 A JP2019119678 A JP 2019119678A
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- soluble metal
- processing oil
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Abstract
Description
即ち、本発明は以下の発明を提供する。
一般式(3)
一般式(1)の水溶性金属加工油剤用防黴剤の製造において、シクロヘキシルアミンとハロゲン化アルキルの反応に用いられる触媒は、NaOH、KOHなどのアルカリ金属塩存在下または、無触媒で合成される。反応重量比率はハロゲン化アルキル:シクロヘキシルアミン=1:1〜1:5であり、好ましくは1:2〜1:4、更に好ましくは1:2〜1:3である。シクロヘキシルアミンの比率が高くなれば、反応効率は向上するが、一度に製造できる量が減り、製造効率が低下する。シクロヘキシルアミンの比率が低すぎると、未反応のハロゲン化アルキルが残存し、収率が低下する。反応溶媒は特に限定されないが、キシレン、トルエン、水、無溶媒などから選択され、好ましくは水または無溶媒である。反応雰囲気は限定されないが、窒素雰囲気下もしくは空気雰囲気下で合成される。アルキル化の反応温度は、60〜140℃で、反応コストや製品の着色などにより、好ましくは80〜120℃の範囲である。生成した塩の中和及び遊離は、NaOH、KOHなどのアルカリ金属塩が用いられ、50〜60℃で行われる。未反応物の留去における温度は50〜140℃で、好ましくは100℃以下である。
攪拌機、温度計、冷却管を装着した1000mLの4つ口フラスコに、シクロヘキシルアミン376.4g(3.795モル)を入れ、還流させた。そこに、n-ブチルクロリド117.1g(0.633モル)を8時間かけて滴下し、還流下で2.5時間反応させた。反応終了後、60℃以下まで冷却後、減圧下で徐々に加温しながら100℃以下にて、過剰のシクロヘキシルアミンの一部を留出させた(125.5g)。その後、60℃まで冷却し、中和するのに十分な40%水酸化ナトリウム水溶液(126.5g)を滴下し、1時間攪拌した。下層を分離後、水を加え、数回にわたり、上層の洗浄を行った。その後、減圧下で、徐々に加温しながら100℃以下にて過剰のシクロヘキシルアミン及び水を留出させることで、目的とする合成物1を得た。
攪拌機、温度計、冷却管を装着した1000mLの4つ口フラスコに、シクロヘキシルアミン188.4g(1.900モル)、水188.4g、n-ブチルクロリド58.6g(1.265モル)を加え、還流下で10時間反応させた。反応終了後、60℃まで冷却し、中和するのに十分な40%水酸化ナトリウム水溶液(63.3g)を滴下し、1時間攪拌した。下層を分離後、水を加え、数回にわたり、上層の洗浄を行った。その後、減圧下で、徐々に加温しながら100℃以下にて過剰のシクロヘキシルアミン及び水を留出させることで、目的とする合成物2を得た。
合成物1) 合成例1で合成された一般式(1)のR1およびR2は水素または炭素数4の飽和炭化水素基を有するシクロヘキシルアミン誘導体
合成物2) 合成例2で合成された一般式(1)のR1およびR2は水素または炭素数4の飽和炭化水素基を有するシクロヘキシルアミン誘導体
成分1) N-n-ブチル-1,2-ベンゾイソチアゾリン-3-オン
成分2) シクロヘキシルアミン
18mL容試験管に塩酸でpH5.6に調製したサブローデキストロース培地(表1)8mLを入れ、高圧蒸気滅菌した。この培地に表2 に示す成分を配合した加工油剤を調製し、実施例では試料が200mMとなるように、N-n-ブチル-1,2-ベンゾイソチアゾリン-3-オンとの併用の場合はその半量である100mMとなるように、比較例ではシクロヘキシルアミンが200mMとなるように添加した。実施例および比較例の加工油剤を滅菌したサブローデキストロース培地8mL入った18mL容試験管に1mL添加した。カビの胞子液は、分光光度計で波長530nmにおける濁度を測定し、0.5のOD(光学密度)を与えるようにサブローデキストロース培地で希釈した。試験管に胞子液1mLを添加し懸濁後、30℃で4日間静置培養した。4日後、試験管内の液を1mL採取し、サブローデキストロース寒天培地に塗布後、30℃でさらに4日間培養し、4日後のカビの発育を観察した。
− : カビのコロニーが存在しない
+ : 数点のカビのコロニーが存在する
+ + : 培地を覆うカビが存在する
Claims (5)
- 一般式(1)において、R1およびR2は同一または異なって、水素または炭素数4〜10の飽和炭化水素基を示し、少なくとも一方は炭化水素基を有する請求項1に記載の水溶性金属加工油用防黴剤。
- 一般式(1)において、R1およびR2は同一または異なって、水素または炭素数4の飽和炭化水素基を示し、少なくとも一方は炭化水素基を有する請求項1または2に記載の水溶性金属加工油用防黴剤。
- 請求項1〜3のいずれかに記載の水溶性金属加工油用防腐防黴剤を含有する水溶性金属加工油剤組成物。
- 水溶性金属加工油剤組成物全量を100重量% とした場合に、水溶性金属加工油用防黴剤の含有量が0.1〜10.0質量%である請求項4に記載の水溶性金属加工油剤組成物
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