JP7010965B2 - 光重合工程を含むサイズ制御されたマイクロカプセルの製造方法 - Google Patents
光重合工程を含むサイズ制御されたマイクロカプセルの製造方法 Download PDFInfo
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- JP7010965B2 JP7010965B2 JP2019549646A JP2019549646A JP7010965B2 JP 7010965 B2 JP7010965 B2 JP 7010965B2 JP 2019549646 A JP2019549646 A JP 2019549646A JP 2019549646 A JP2019549646 A JP 2019549646A JP 7010965 B2 JP7010965 B2 JP 7010965B2
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- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
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- A—HUMAN NECESSITIES
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- F28D20/02—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00 using latent heat
- F28D20/023—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00 using latent heat the latent heat storage material being enclosed in granular particles or dispersed in a porous, fibrous or cellular structure
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Description
a)撹拌しつつ、光架橋性ポリマー組成物C2に少なくとも1種の活性成分を含む組成物C1を添加するに際し、組成物C2に分散した組成物C1の液滴を含むエマルション(E1)が得られる工程であって、組成物C1及びC2は互いに混和しない工程と;
b)撹拌しつつ、組成物C3にエマルション(E1)を添加するに際し、組成物C3に分散した液滴を含むダブルエマルション(E2)が得られる工程であって、組成物C2及びC3は互いに混和せず、
組成物C3の粘度は、エマルション(E1)の粘度より高く、かつ、25℃において2000mPa.s超である工程と;
c)エマルション(E2)にせん断を適用するに際し、組成物C3に分散したサイズ制御された液滴を含むダブルエマルション(E3)が得られる工程であって、
適用されるせん断速度が1000s-1未満である工程と;
d)組成物C2を光重合するに際し、組成物C3に分散した固体マイクロカプセルが得られる工程とを含む固体マイクロカプセルの製造方法に関する。
工程a)中、組成物C1は光架橋性ポリマー組成物C2に添加され、この工程は撹拌しつつ実施され、このことは、組成物C1及びC2の混合物を乳化させるために、組成物C1が添加される間、組成物C2が、典型的には機械的に撹拌されることを意味する。
組成物C1は、少なくとも1種の活性成分Aを含む。本発明の方法において、この組成物C1は、本発明の方法中に形成される液滴内及びそのようにして得られる固体カプセル内での活性成分Aのキャリアとして働く。
-ポリマー及びエラストマー配合物;ゴム、塗料、接着剤、密封剤、モルタル、ワニス又はコーティング剤の重合に用いられる架橋剤、硬化剤、有機又は金属触媒(白金、パラジウム、チタン、モリブデン、銅、亜鉛の有機金属又は無機金属錯体等);
-エラストマー、塗料、コーティング剤、接着剤、密封剤、モルタル又は紙の配合物用の染料又は顔料;
-洗剤製品等の洗浄剤、ホームケア製品、化粧品及びパーソナルケア製品、テキスタイル、塗料、コーティング剤用の香料(International Fragrance Association(IFRA)により規定された分子リスト、www.ifraorg.orgウェブサイトで入手可能である);
-食品化合物及び動物試料用の芳香剤、ビタミン、アミノ酸、タンパク質、脂質、プロバイオティクス、酸化防止剤、pH補正剤、防腐剤;
-洗浄剤、洗剤製品、化粧品及びパーソナルケア製品用の柔軟剤、コンディショナー。このように、使用可能な活性成分は、例えば米国特許第6335315号及び米国特許第5877145号に記載される。
-洗浄剤、洗剤製品及びホームケア製品用の変色防止剤(アンモニウム誘導体等)、消泡剤(アルコールエトキシレート、アルキルベンゼンスルホネート、ポリエチレンエトキシレート、アルキルエトキシサルフェート又はアルキルサルフェート等);
-洗浄剤、洗剤製品、化粧品及びパーソナルケア製品を意図した、色活性剤とも呼ばれる光沢剤(スチルベン誘導体、クマリン誘導体、ピラゾリン誘導体、ベンゾオキサゾール誘導体、又はナフタルイミド誘導体等);
-酵素、ビタミン、タンパク質、植物抽出物、皮膚軟化剤、殺菌剤(disinfecting agent)、抗菌剤、抗UV剤、化粧品及びテキスタイルに対するスキンケア製品を意図した薬剤等の生物学的に活性な化合物。これらの生物学的に活性な化合物としては、ビタミンA、B、C、D及びE、パラアミノ安息香酸、αヒドロキシ酸(グリコール酸、乳酸、リンゴ酸、酒石酸又はクエン酸等)、樟脳、セラミド、ポリフェノール(フラボノイド、フェノール酸、エラグ酸、トコフェロール、ユビキノール等)、ヒドロキノン、ヒアルロン酸、イソプロピルイソステアレート、イソプロピルパルミテート、オキシベンゾン、パンテノール、プロリン、レチノール、レチニルパルミテート、サリチル酸、ソルビン酸、ソルビトール、トリクロサン、チロシンが挙げられる;
-塗料及びコーティング剤用の殺菌剤(disinfecting agent)、抗菌剤、抗UV剤;
-農薬用の肥料、除草剤、殺虫剤(insecticide)、殺虫剤(pesticide)、殺菌剤(fungicide)、防虫剤又は消毒剤;
-プラスチック、コーティング、塗料及びテキスタイルにおいて用いられる難燃剤(flame retardant)とも呼ばれる防火剤(fire-proofing agent)(テトラブロモビスフェノールA等の臭素化ポリオール、ハロゲン化又は非ハロゲン化有機リン化合物、塩素化化合物、三水和アルミニウム、酸化アンチモン、ホウ素酸亜鉛、赤リン、メラミン又は二水酸化マグネシウム等);
-塗料、コーティング及び湾曲した可撓性スクリーンを形成するポリマー材料に関するフォトニック結晶又はフォトクロモフォア;
-エネルギーの貯蔵が意図される、相変化を受けたときに熱を吸収するか戻すことのできる相変化材料(PCM)として当業者に知られている製品。PCMの例及びその応用は、Faridら、Energy Conversion and Management、2004、45(9-10)、1597-1615に記載されている。PCMの例として、リン酸アルミニウム、炭酸アンモニウム、塩化アンモニウム、炭酸セシウム、硫酸セシウム、クエン酸カルシウム、塩化カルシウム、水酸化カルシウム、酸化カルシウム、リン酸カルシウム、カルシウムサッカラート、硫酸カルシウム、リン酸セリウム、リン酸鉄、炭酸リチウム、硫酸リチウム、塩化マグネシウム、硫酸マグネシウム、塩化マンガン、硝酸マンガン、硫酸マンガン、酢酸カリウム、炭酸カリウム、塩化カリウム、リン酸カリウム、炭酸ルビジウム、硫酸ルビジウム、四ホウ酸二ナトリウム、酢酸ナトリウム、重炭酸ナトリウム、重硫酸ナトリウム、クエン酸ナトリウム、塩化ナトリウム、水酸化ナトリウム、硝酸ナトリウム、過炭酸ナトリウム、過硫酸ナトリウム、リン酸ナトリウム、プロピオン酸ナトリウム、亜セレン酸ナトリウム、ケイ酸ナトリウム、硫酸ナトリウム、テルル酸ナトリウム、チオ硫酸ナトリウム、ストロンチウムヒドロホスフェート、酢酸亜鉛、塩化亜鉛、チオ硫酸ナトリウム、炭化水素パラフィンワックス、ポリエチレングリコールの溶融塩に言及することができる;
である。
組成物C2は光架橋性組成物であり、このことは、それが、本発明の固体マイクロカプセルの重合したエンベロープを形成するために、重合(架橋)して固体材料を与えることのできる組成物であることを意味する。
-1,6-ヘキサンジオールジアクリレート、1,6-ヘキサンジオールジメタクリレート、ポリエチレングリコールジメタクリレート、1,9-ノナンジオールジメタクリレート、1,4-ブタンジオールジメタクリレート、2,2-ビス(4)メタクリロキシフェニル)プロパン等のジアクリレート、1,3-ブタンジオールジメタクリレート、1,10-デカンジオールジメタクリレート、ビス(2-メタクリロキシエチル)N,N’-1,9-ノニレンビスカルバメート、1,4-ブタンジオールジアクリレート、エチレングリコールジアクリレート、1,5-ペンタンジオールジメタクリレート、1,4-フェニレンジアクリレート、アリルメタクリレート、N,N’-メチレンビスアクリルアミド、2,2-ビス[4-(2-ヒドロキシ-3-メタクリロキシプロポキシ)フェニル]プロパン、テトラエチレングリコールジアクリレート、エチレングリコールジメタクリレート、ジエチレングリコールジアクリレート、トリエチレングリコールジアクリレート、トリエチレングリコールジメタクリレート、ポリエチレングリコールジグリシジルエーテル、N,N-ジアリルアクリルアミド、2,2-ビス[4-(2-アクリロキシエトキシ)フェニル]プロパン、グリシジルメタクリレート;
-ジペンタエリスリトールペンタアクリレート、1,1,1-トリメチロールプロパントリアクリレート、1,1,1-トリメチロールプロパントリメタクリレート、エチレンジアミンテトラメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート等の多官能アクリレート;
-プロパルギルメタクリレート、2-シアノエチルアクリレート、トリシクロデカンジメタノールジアクリレート、ヒドロキシプロピルメタクリレート、N-アクリロキシスクシンイミド、N-(2-ヒドロキシプロピル)メタクリルアミド、N-(3-アミノプロピル)メタクリルアミド塩酸塩、N-(t-BOC-アミノプロピル)メタクリルアミド、2-アミノエチルメタクリレート塩酸塩、モノアクリロキシエチルホスフェート、o-ニトロベンジルメタクリレート、アクリル酸無水物、2-(tert-ブチルアミノ)エチルメタクリレート、N,N-ジアリルアクリルアミド、グリシジルメタクリレート、2-ヒドロキシエチルアクリレート、4-(2-アクリロキシエトキシ)-2-ヒドロキシベンゾフェノン、N-(フタルイミドメチル)アクリルアミド、シンナミルメタクリレート等の別の反応性官能基をさらに有するアクリレートに言及することができる。
-例えば、BASF社により名称DAROCUR(登録商標)1173及び4265、IRGACURE(登録商標)184、2959、及び500として、CYTECによりADDITOL(登録商標)CPKとして販売されている2-ヒドロキシ-2-メチル-1-フェニル-1-プロパノン等のα-ヒドロキシケトン;
-α-アミノケトン、特に、例えば、BASF社により名称Irgacure(登録商標)907及び369として販売されている2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-ブタノン-1;
-例えば、LAMBERTIにより名称ESACURE(登録商標)TZTとして販売されている芳香族ケトン;又は例えば、LAMBERTIにより名称ESACURE(登録商標)ITXとして販売されているチオキサントン、及びキノン。これらの芳香族ケトンは、ほとんどの場合、第三級アミン等の水素供与性化合物、特にアルカノールアミンの存在を必要とする。LAMBERTI社により販売されている第三級アミンESACURE(登録商標)EDBに言及することができる。
-最も一般的な代表例が、BASFにより名称IRGACURE(登録商標)651として販売されているベンジルジメチルケタールであるα-ジカルボニル誘導体。他の商品は、LAMBERTIにより名称ESACURE(登録商標)KB1として販売されている。及び
-例えば、BASF社により、名称Irgacure(登録商標)819、1700及び1800、DAROCUR(登録商標)4265、LUCIRIN(登録商標)TPO、並びにLUCIRIN(登録商標)TPO-Lとして販売されている、例えばビス-アシルホスフィンオキシド(BAPO)等のアシルホスフィンオキシドが挙げられる。
-フッ素化基等の疎水性基、例えばトリフルオロエチルメタクリレート、トリフルオロエチルアクリレート、テトラフルオロプロピルメタクリレート、ペンタフルオロプロピルアクリレート、ヘキサフルオロブチルアクリレート、又はフルオロフェニルイソシアネート;
-第一級、第二級又は第三級アミン、カルボン酸、ホスフェート、サルフェート、ニトレート又はカーボネート基等のpH感受性基;
-アゾベンゼン、スピロピラン、2-ジアゾ-1,2-ナフトキノン、o-ニトロベンジル、チオール、又は6-ニトロ-ベラトロイルオキシカルボニル等のUV感受性又はUV開裂可能な基(又はフォトクロミック基)、例えばポリエチレンオキシド)-ブロック-ポリ(2-ニトロベンジルメタクリレート)、及び(特に、Liuら、Polymer Chemistry2013、4、3431-3443に記載の)他のブロックコポリマー;
-о-ニトロベンジル又は2-ジアゾ-1,2-ナフトキノン等のIR感受性又はIR開裂可能な基、例えばLiuらPolymer Chemistry2013、4、3431-3443に記載のポリマー;及び
-ポリ(N-イソプロピルアクリルアミド)等の温度感受性基
のうちの1種をさらに有するモノマー又はポリマーから選択されることができる。
工程b)中、工程a)で得られたエマルション(E1)は組成物C3に添加され、この工程は撹拌しつつ実施され、このことは、組成物C1、C2及びC3の混合物を乳化させるために、エマルション(E1)が添加される間、組成物C3が、典型的には機械的にかき混ぜられることを意味する。
本発明によれば、25℃における組成物C3の粘度は、25℃におけるエマルション(E1)の粘度より高い。
-セルロースエーテル:メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース、メチルヒドロキシエチルセルロース、エチルヒドロキシエチルセルロース、カルボキシメチルセルロース、ヒドロキシプロピルセルロース又はメチルヒドロキシプロピルセルロース等のセルロース誘導体;
-ポリアクリル酸(PAA)、ポリメタクリル酸(PMAA)、ポリ(ヒドロキシエチルメタクリレート)(pHEMA)、ポリ(N-2-ヒドロキシプロピルメタクリレート)(pHPMA)等のポリアクリレート(カルボマーとも呼ばれる);
-ポリ(N-イソプロピルアクリルアミド)(PNIPAM)等のポリアクリルアミド;
-ポリビニルピロリドン(PVP)及びその誘導体;
-ポリビニルアルコール(PVA)及びその誘導体;
-ポリ(エチレングリコール)、ポリ(プロピレングリコール)及びその誘導体、たとえばポリ(エチレングリコール)アクリレート/メタクリレート、ポリ(エチレングリコール)ジアクリレート/ジメタクリレート、ポリプロピレンカーボネート;
-カラギーナン、イナゴマメガム又はタラガム、デキストラン、キサンタンガム、キトサン、アガロース、ヒアルロン酸、ジェランガム、グアーガム、アラビアゴム、トラガカントゴム、デュータン(diutane)ガム、オーツガム、カラヤガム、ガティガム、カードランガム、ペクチン、こんにゃくガム、スターチ等の多糖類;
-ゼラチン、コラーゲン、フィブリン、ポリリシン、アルブミン、カゼイン等のタンパク質誘導体;
-ポリジメチルシロキサン(ジメチコンとも呼ばれる)、アルキルシリコーン、アリールシリコーン、アルキルアリールシリコーン、ポリエチレングリコールジメチコン、ポリプロピレングリコールジメチコン等のシリコーン誘導体;
-ジエステルワックス(アルカンジオールジエステル、ヒドロキシル酸ジエステル)、トリエステルワックス(トリアシルグリセロール、アルカン-1,2-ジオール、ω-ヒドロキシ酸及び脂肪酸のトリエステル、ヒドロキシマロン酸、脂肪酸及びアルコールのエステル、ヒドロキシル酸、脂肪酸及び脂肪アルコールのトリエステル、脂肪酸、ヒドロキシル酸及びジオールのトリエステル)、及びポリエステルワックス(脂肪酸のポリエステル)等のワックス。本発明の文脈においてワックスとして用いることのできる脂肪酸エステルは、例えばパルミチン酸セチル、オクタン酸セチル、ラウリン酸セチル、乳酸セチル、イソノナン酸セチル及びステアリン酸セチル、ステアリン酸ステアリル、ステアリン酸ミリスチル、ミリスチン酸セチル、ステアリン酸イソセチル、グリセリルトリミリステート、グリセリルトリパルミテート、グリセリルモノステアレート、又はセチルグリセリルパルミテートである。;
-セロチン酸、パルミチン酸、ステアリン酸、ジヒドロキシステアリン酸、ベヘン酸、リグノセリン酸、アラキン酸、ミリスチン酸、ラウリン酸、トリデカン酸、ペンタデカン酸、マルガリン酸、ノナデシル酸、ヘンイコシル(henicosylic)酸、トリコシル酸、ペンタコシル酸、ヘプタコシル酸、モンタン酸又はノナコシル酸等のワックスとして用いることができる脂肪酸;
-脂肪酸塩、特にステアリン酸アルミニウム、ヒドロキシルアルミニウムビス(2-エチルヘキサノエート)等の脂肪酸アルミニウム塩;
-異性体ホホバ油;
-水素化ひまわり油;
-水素化ココナッツオイル;
-水素化ラノリン油;
-ヒマシ油及びその誘導体、特に修飾水素化ヒマシ油又は脂肪族アルコールによりヒマシ油のエステル化をすることにより得られる化合物;
-ポリウレタン及びその誘導体;
-スチレンブタジエン等のスチレン系ポリマー;
-ポリイソブテン等のポリオレフィン
に言及することができ、これらは単独又は混合して用いることができる。
工程c)において、連続相において分散した多分散液滴からなるエマルション(E2)は、せん断、例えば混合機において、低いせん断速度、すなわち1000s-1未満のせん断速度のせん断に供される。
σ=ηγ
により関係づけられる。
工程d)は、エマルション(E3)を光重合に供することからなり、それは、組成物C2の光重合を可能にする。
例1:高粘性c3相及び低せん断による固体マイクロカプセルの調製
この例は、ダブルエマルション(E2)に非常に低いせん断を適用することによってさえ、20μm未満のサイズの単分散カプセルを得ることを可能にする粘性C3組成物の使用を示す。
-組成物C1は、5質量%のアルギネート(活性成分)の溶液である。
-組成物C2は、69質量%のCN981ポリマー(Sartomer brand、Arkemaのポリアクリレートオリゴマー);30質量%のヘキサンジオールジアクリレート(架橋剤)、及び1質量%のDarocure1173(光開始剤)の混合物である。
-組成物C3は、15質量%のアルギネートの溶液である(25℃における粘度:63000s-1)。
直径3cmの解膠撹拌プロペラを備えた機械的撹拌機(Heidolph RZR 2021)を用いて、全ての乳化工程を実施する。
この例は、例1と同じ配合を用いて、高いせん断の適用が、得られるカプセルの単分散性を改善しないことを示す。
この例は、25℃において2000mPa.s未満の粘性を有する組成物C3を用いてマイクロカプセルを製造した際に、20μm未満の単分散サイズのマイクロカプセルを得るのに高せん断の追加の工程を用いる必要があることを示す。
-C1及びC2の組成物は、例1のものと同一である。
-組成物C3は、5質量%のアルギネートの溶液であり、その粘度は1500mPa.sである。
工程a)及びb)は、例1のものと同様に実施される。
本開示は以下も包含する。
[1]
a)撹拌しつつ、光架橋性ポリマー組成物C2に少なくとも1種の活性成分を含む組成物C1を添加するに際し、組成物C2に分散した組成物C1の液滴を含むエマルション(E1)が得られる工程であって、前記組成物C1及びC2は互いに混和しない工程と;
b)撹拌しつつ、組成物C3に前記エマルション(E1)を添加するに際し、前記組成物C3に分散した液滴を含むダブルエマルション(E2)が得られる工程であって、前記組成物C2及びC3は互いに混和せず、
前記組成物C3の粘度は、前記エマルション(E1)の粘度より高く、かつ、25℃において2000mPa.s超である工程と;
c)前記エマルション(E2)にせん断を適用するに際し、前記組成物C3に分散したサイズ制御された液滴を含むダブルエマルション(E3)が得られる工程であって、
適用されるせん断速度が1000s -1 未満である工程と;
d)前記組成物C2を光重合するに際し、前記組成物C3に分散した固体マイクロカプセルが得られる工程とを含む固体マイクロカプセルの製造方法。
[2]
前記組成物C2が、25℃において500mPa.s~100000mPa.sの粘度を有する液体である、上記態様1に記載の方法。
[3]
前記組成物C2が、少なくとも1種のモノマー又はポリマーと、少なくとも1種の架橋剤と、少なくとも1種の光開始剤とを含む、上記態様1又は2に記載の方法。
[4]
前記組成物C2が、組成物C2の全質量に対して0.001質量%~70質量%の架橋剤を含む、上記態様3に記載の方法。
[5]
前記活性成分が、前記組成物C1に可溶化されているか、前記組成物C1に固体粒子の形態で分散している、上記態様1~4のいずれかに記載の方法。
[6]
前記組成物C3が、少なくとも1種の分岐鎖ポリマー、好ましくは5000g.mоl -1 を超える分子量を有する分岐鎖ポリマー、及び/又は5000g.mоl -1 を超える分子量を有する少なくとも1種のポリマー、及び/又はシリケート等の固体粒子を含む、上記態様1~5のいずれかに記載の方法。
[7]
組成物C3の25℃における粘度が、1000mPa.s~100000mPa.sである、上記態様1~6のいずれかに記載の方法。
[8]
工程c)において適用されるせん断速度が、10s -1 ~1000s -1 である、上記態様1~7のいずれかに記載の方法。
[9]
工程d)が、前記組成物C2の光重合を開始することのできる光源に前記エマルション(E3)を曝露することを含む、上記態様1~8のいずれかに記載の方法。
[10]
前記光源が、UV光源である、上記態様9に記載の方法。
Claims (10)
- a)撹拌しつつ、光架橋性ポリマー組成物C2に少なくとも1種の活性成分を含む組成物C1を添加するに際し、組成物C2に分散した組成物C1の液滴を含むエマルション(E1)が得られる工程であって、前記組成物C1及びC2は互いに混和しない工程と;
b)撹拌しつつ、組成物C3に前記エマルション(E1)を添加するに際し、前記組成物C3に分散した液滴を含むダブルエマルション(E2)が得られる工程であって、前記組成物C2及びC3は互いに混和せず、
前記組成物C3の粘度は、前記エマルション(E1)の粘度より高く、かつ、25℃において2000mPa.s超である工程と;
c)前記エマルション(E2)にせん断を適用するに際し、前記組成物C3に分散したサイズ制御された液滴を含むダブルエマルション(E3)が得られる工程であって、
適用されるせん断速度が1000s-1未満である工程と;
d)前記組成物C2を光重合するに際し、前記組成物C3に分散した固体マイクロカプセルが得られる工程とを含む固体マイクロカプセルの製造方法。 - 前記組成物C2が、25℃において500mPa.s~100000mPa.sの粘度を有する液体である、請求項1に記載の方法。
- 前記組成物C2が、少なくとも1種のモノマー又はポリマーと、少なくとも1種の架橋剤と、少なくとも1種の光開始剤とを含む、請求項1又は2に記載の方法。
- 前記組成物C2が、組成物C2の全質量に対して0.001質量%~70質量%の架橋剤を含む、請求項3に記載の方法。
- 前記活性成分が、前記組成物C1に可溶化されているか、前記組成物C1に固体粒子の形態で分散している、請求項1~4のいずれか1項に記載の方法。
- 前記組成物C3が、少なくとも1種の分岐鎖ポリマー、及び/又は5000g.mоl-1を超える分子量を有する少なくとも1種のポリマー、及び/又は固体粒子を含む、請求項1~5のいずれか1項に記載の方法。
- 組成物C3の25℃における粘度が、1000mPa.s~100000mPa.sである、請求項1~6のいずれか1項に記載の方法。
- 工程c)において適用されるせん断速度が、10s-1~1000s-1である、請求項1~7のいずれか1項に記載の方法。
- 工程d)が、前記組成物C2の光重合を開始することのできる光源に前記エマルション(E3)を曝露することを含む、請求項1~8のいずれか1項に記載の方法。
- 前記光源が、UV光源である、請求項9に記載の方法。
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