JP7327459B2 - 溶剤組成物、洗浄方法、塗膜の形成方法、熱移動媒体および熱サイクルシステム - Google Patents
溶剤組成物、洗浄方法、塗膜の形成方法、熱移動媒体および熱サイクルシステム Download PDFInfo
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- JP7327459B2 JP7327459B2 JP2021200311A JP2021200311A JP7327459B2 JP 7327459 B2 JP7327459 B2 JP 7327459B2 JP 2021200311 A JP2021200311 A JP 2021200311A JP 2021200311 A JP2021200311 A JP 2021200311A JP 7327459 B2 JP7327459 B2 JP 7327459B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5027—Hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
- B08B3/04—Cleaning involving contact with liquid
- B08B3/08—Cleaning involving contact with liquid the liquid having chemical or dissolving effect
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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Description
このように、フルオロオレフィンの種類によって安定化のための技術が異なることが知られている。仮に先行技術文献に記載された技術を適用したとしても、1-クロロ-2,3,3-トリフルオロ-1-プロペンに対する安定化効果が得られるかどうかは予測できない。
[2]前記溶剤組成物(100質量%)中の前記安定剤の含有量が1質量ppm~10質量%である、[1]に記載の溶剤組成物。
[3]前記溶剤組成物(100質量%)中の1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量が80質量%以上である、[1]または[2]に記載の溶剤組成物。
[5]前記安定剤の沸点が30~120℃である、[1]~[4]のいずれかに記載の溶剤組成物。
[6]前記安定剤が、メタノール、エタノール、イソプロパノール、2-プロピン-1-オール、1,2-ブチレンオキシド、テトラヒドロフラン、1,4-ジオキサン、n-プロピルアミン、ジイソプロピルアミン、N-メチルモルホリン、N-メチルピロール、2-メチル-2-ブテン、2-メチル-1-ペンテン、2-メチル-2-ペンテン、3-エチル-2-ブテン、2,3-ジメチル-2-ブテン、2,4,4-トリメチル-1-ペンテン、2,4,4-トリメチル-2-ペンテン、n-ヘプタンから選ばれる少なくとも1つを含む、[5]に記載の溶剤組成物。
[8]被洗浄物が繊維製品、医療器具、電気機器、精密機械、光学物品から選ばれる少なくとも1種である、[7]に記載の洗浄方法。
[9][1]~[6]のいずれかに記載の溶剤組成物に不揮発性物質を溶解し、得られた不揮発性物質の組成物を被塗布物上に塗布し、前記溶剤組成物を蒸発させ、前記不揮発性物質を主成分とする塗膜を形成することを特徴とする、塗膜の形成方法。
[10][1]~[6]のいずれかに記載の溶剤組成物を含む熱移動媒体。
[11][10]に記載の熱移動媒体を用いた熱サイクルシステム。
本発明の洗浄方法は、地球環境に悪影響を及ぼさず、洗浄性に優れる。
本発明の塗膜の形成方法は、地球環境に悪影響を及ぼさず、均一な塗膜を形成することができる。
本発明の該溶剤組成物を含む熱移動媒体は、地球環境に悪影響を及ぼさず、安定性に優れる。
本発明の該熱移動媒体を用いた熱サイクルシステムは、地球環境に悪影響を及ぼさない。
HCFO-1233ydは、炭素原子-炭素原子間に二重結合を持つフルオロオレフィンであるため、大気中での寿命が短く、オゾン破壊係数や地球温暖化係数が小さい。
本実施形態におけるHCFO-1233ydの純度は99質量%以上が好ましく、99.5質量%以上がより好ましい。
本実施形態の溶剤組成物(100質量%)中のHCFO-1233ydの量は、80~99.9999質量%であることが好ましく、90~99.9995質量%であることが好ましい。上記範囲内であることにより、溶剤組成物の各種有機物の溶解性に優れる。
本実施形態の溶剤組成物において、HCFO-1233ydは、HCFO-1233yd(Z)またはHCFO-1233yd(E)を単独で用いてもよいし、およびHCFO-1233yd(Z)とHCFO-1233yd(E)の混合体を用いてもよい。
HCFO-1233yd(Z)とHCFO-1233yd(E)の混合体を用いる場合、HCFO-1233yd(Z)とHCFO-1233yd(E)の合計量に対するHCFO-1233yd(Z)の含有割合は、80質量%以上100質量%未満であることが好ましく、90質量%以上99質量%以下がより好ましく、95質量%以上98質量%以下がさらに好ましい。HCFO-1233yd(Z)よりHCFO-1233yd(E)の方が、沸点が高いため、HCFO-1233yd(Z)の含有割合が前記下限値以上であれば、溶剤組成物の洗浄剤や塗布溶剤として実用上取扱いやすい。
本実施形態の溶剤組成物における上記炭化水素類の含有量としては、本実施形態の溶剤組成物に対して1質量ppm~10質量%が好ましく、より好ましくは5質量ppm~7質量%、さらに好ましくは10質量ppm~5質量%であり、0.001~0.1質量%が最も好ましい。炭化水素類の含有量が上記好ましい範囲内であると、HCFO-1233ydに対する十分な安定性を示すことに加え、HCFO-1233ydのもつ表面張力や粘度が低く、浸透性が良いという特性を阻害しない点から特に優れている。
上記化合物を安定剤として用いることにより、HCFO-1233ydの分解を引き起こす原因物質、例えば酸素ラジカル等の過酸化物、の発生を抑えられる。また、酸素ラジカルが発生してHCFO-1233ydの還元体を生成した場合でも、還元体を再度酸化させてHCFO-1233ydを生成することができる。
i)メタノール、エタノール、イソプロパノール、2-プロピン-1-オール
ii)2-メチル-1-ペンテン、2-メチル-2-ペンテン、3-エチル-2-ブテン、2,3-ジメチル-2-ブテン、2,4,4-トリメチル-1-ペンテン、2,4,4-トリメチル-2-ペンテン、n-ヘプタン
iii)N-メチルピロール、N-メチルモルホリン、n-プロピルアミン、ジイソプロピルアミン
本実施形態の溶剤組成物に含まれる溶剤(A)は、1種であってもよく、2種以上であってもよい。
本実施形態の溶剤組成物を用いた被洗浄物の洗浄方法は、本実施形態の溶剤組成物を用いて被洗浄物となる物品の表面に本実施形態の溶剤組成物を接触させて物品に付着する汚れを除去すること以外は特に限定されない。例えば、手拭き洗浄、浸漬洗浄、スプレー洗浄、浸漬揺動洗浄、浸漬超音波洗浄、蒸気洗浄、およびこれらを組み合わせた方法等を採用すればよい。洗浄装置、洗浄条件等も公知のものを適宜選択でき、分解することなく長期間繰り返し使用することができる。
本実施形態の溶剤組成物は、衣類の洗浄剤、すなわち、ドライクリーニング用溶剤、として適している。
また本実施形態の溶剤組成物を、例えば不揮発性溶質成分を物品表面に塗布する溶剤として使用する場合には、溶質成分を本実施形態の溶剤組成物に溶解した溶液とし、その溶液を被塗布物上に塗布し、溶剤組成物を蒸発させ、上記被塗布物上に不揮発性成分塗膜を形成させる。
潤滑剤とは、2つの部材が互いの面を接触させた状態で運動するときに、接触面における摩擦を軽減し、熱の発生や摩耗損傷を防ぐために用いるものを意味する。潤滑剤は、液体(オイル)、半固体(グリース)、固体のいずれの形態であってもよい。
本実施形態の熱移動媒体用途は、熱サイクルシステムに本実施形態の溶剤組成物を作動媒体(熱移動媒体)として用いることができる。これにより物質を加熱したり冷却したりすることができる。
以下、熱サイクルシステムの一例として、冷凍サイクルシステムについて説明する。
二次循環冷却システムとは、アンモニアや炭化水素冷媒からなる一次冷媒を冷却する一次冷却手段と、二次循環冷却システム用二次冷媒(以下、「二次冷媒」という。)を循環させて被冷却物を冷却する二次循環冷却手段と、一次冷媒と二次冷媒とを熱交換させ、二次冷媒を冷却する熱交換器と、を有するシステムである。この二次循環冷却システムにより、被冷却物を冷却できる。本実施形態の作動媒体は、二次冷媒としての使用に好適である。
2000gのHCFC-244caを原料にして、テトラ-n-ブチルアンモニウムクロリドの19.9gを入れ、反応温度を50℃に保ち、40質量%水酸化カリウム水溶液の2792gを30分かけて滴下した。その後、52時間反応を続け、有機層を回収した。回収した有機層を精製した結果、純度99.9質量%のHCFO-1233yd(Z)を1520g、純度99.9質量%のHCFO-1233yd(E)を140g得た。この反応を繰返し実施し、必要量のHCFO-1233yd(Z)またはHCFO-1233yd(E)を製造した。
また、同様の反応により得られた、HCFO-1233yd(Z)とHCFO-1233yd(E)とを混合物として分離し、HCFO-1233yd(Z)とHCFO-1233yd(E)の異性体混合物も製造した。このとき得られた異性体混合物は、HCFO-1233yd(Z)95質量%、HCFO-1233yd(E)5質量%であった。
純度99.9質量%のHCFO-1233yd(Z)、HCFO-1233yd(E)またはHCFO-1233ydの異性体混合物に、表1~3に示すように安定剤を所定の濃度になるように添加して、溶剤組成物をそれぞれ100gずつ調製した。なお、表3~6において、前記参考例により得られたHCFO-1233ydの異性体混合物は、単に「HCFO-1233yd」と示した。
得られた溶剤組成物を50℃で3日間保存した。
調製直後と保存後の塩素イオン濃度を測定した結果を表1~3に示す。評価の指標はいずれも塩素イオン濃度である。
「A(優良):10質量ppm未満」
「B(良):10質量ppm以上50ppm未満」
「C(やや不良):50質量ppm以上100ppm未満」
「D(不良):100質量ppm以上」
「A(優良):溶剤組成物が完全に揮発して跡が残らない」
「B(良):溶剤組成物がほぼ揮発して跡が残らない」
「C(可):若干の残留物は認められるが実用上問題ない」
「D(不良):明らかな残留物が認められる」
上記の例4、14、19、20、27、28、50、52、55、60、78、80(実施例)、例1、2(比較例)の溶剤組成物について、日本工業規格JIS K 1508-1982の加速酸化試験に準拠し、還流時間を48時間における安定性を確認する試験を実施した。各200mlの溶剤組成物中に、気相と液相に機械構造用炭素鋼(S20C)試験片を共存させた条件下で、水分を飽和させた酸素気泡を通しながら、電球で光を照射し、その電球の発熱で還流した。
「A(優良):10質量ppm未満」
「B(良):10質量ppm以上50ppm未満」
「C(やや不良):50質量ppm以上100ppm未満」
「D(不良):100質量ppm以上」
「A(優良):試験前後で変化なし」
「B(良):わずかに光沢が失われたが、実用上問題ない」
「C(やや不良):表面がわずかに錆びている」
「D(不良):表面の全面に錆びがみとめられる」
実施例で得られた一部の溶剤組成物について、以下の各洗浄試験を行い、その結果を表5に示した。
SUS-304のテストピース(25mm×30mm×2mm)を、切削油である製品名「ダフニーマーグプラスHT-10」(出光興産株式会社製)中に浸漬した後、各例の溶剤組成物50mL中に1分間浸漬し、引き上げて切削油が除去された度合を観察した。洗浄性の評価は以下の基準に従って行った。
「B(良好):切削油がほぼ除去される。」
「C(やや不良):切削油が微量に残存する。」
「D(不良):切削油がかなり残存する。」
切削油として製品名「ダフニーマーグプラスAM20」(出光興産株式会社製)を使用した以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価した。
切削油として製品名「ダフニーマーグプラスHM25」(出光興産株式会社製)を使用した以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価した。
切削油として製品名「G-6318FK」(日本工作油株式会社製)を使用した以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価した。
実施例で得られた一部の溶剤組成物とフッ素系潤滑剤である製品名「クライトックス(登録商標)GPL102」(デュポン株式会社製、フッ素系オイル)を混合し、塗布溶剤として該フッ素系潤滑剤の含有量が0.5質量%である潤滑剤溶液を調製した。
各例の潤滑剤溶液の溶解状態を目視で確認し、以下の基準で評価した。
「A(優良):直ちに均一に溶解し、透明になる。」
「B(良好):振盪すれば均一に溶解し、透明になる。」
「C(やや不良):若干白濁する。」
「D(不良):白濁もしくは相分離する。」
各例における潤滑剤塗膜の状態を目視で確認して以下の基準で評価した。
「A(優良):均一な塗膜である。」
「B(良好):ほぼ均一な塗膜である。」
「C(やや不良):塗膜に部分的にムラが見られる。」
「D(不良):塗膜にかなりムラが見られる。」
本実施形態の溶剤組成物を用いて、ウール生地の白色カーディガンを洗浄して洗浄性、風合いの状態を以下のように評価した。
Claims (10)
- 1-クロロ-2,3,3-トリフルオロ-1-プロペンと、
不飽和炭化水素を含む安定剤と、
を含み、
前記不飽和炭化水素が、2-メチル-2-ブテン、2-メチル-1-ペンテン、2-メチル-2-ペンテン、3-エチル-2-ブテン、2,3-ジメチル-2-ブテン、2,4,4-トリメチル-1-ペンテン、および2,4,4-トリメチル-2-ペンテンからなる群から選ばれる少なくとも1種である溶剤組成物。 - 前記溶剤組成物(100質量%)中の前記安定剤の含有量が1質量ppm~10質量%である、請求項1に記載の溶剤組成物。
- 前記溶剤組成物(100質量%)中の1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量が80質量%以上である、請求項1または2に記載の溶剤組成物。
- 前記1-クロロ-2,3,3-トリフルオロ-1-プロペンが、1-クロロ-2,3,3-トリフルオロ-1-プロペンのZ異性体と1-クロロ-2,3,3-トリフルオロ-1-プロペンのE異性体の混合体であり、
前記1-クロロ-2,3,3-トリフルオロ-1-プロペンのZ異性体と前記1-クロロ-2,3,3-トリフルオロ-1-プロペンのE異性体の合計量に対する1-クロロ-2,3,3-トリフルオロ-1-プロペンのZ異性体の含有割合は、80質量%以上100質量%未満である、請求項1~3のいずれか一項に記載の溶剤組成物。 - 前記安定剤の沸点が30~120℃である、請求項1~4のいずれか一項に記載の溶剤組成物。
- 請求項1~5のいずれか一項に記載の溶剤組成物を用いて被洗浄物を洗浄することを特徴とする、洗浄方法。
- 被洗浄物が繊維製品、医療器具、電気機器、精密機械、光学物品から選ばれる少なくとも1種である、請求項6に記載の洗浄方法。
- 請求項1~5のいずれか一項に記載の溶剤組成物に不揮発性物質を溶解し、得られた不揮発性物質の組成物を被塗布物上に塗布し、前記溶剤組成物を蒸発させ、前記不揮発性物質を主成分とする塗膜を形成することを特徴とする、塗膜の形成方法。
- 請求項1~5のいずれか一項に記載の溶剤組成物を含む熱移動媒体。
- 請求項9に記載の熱移動媒体を用いた熱サイクルシステム。
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