JP2018530650A - 疎水的に改質された酸化セリウム粒子およびそれらの使用 - Google Patents
疎水的に改質された酸化セリウム粒子およびそれらの使用 Download PDFInfo
- Publication number
- JP2018530650A JP2018530650A JP2018514996A JP2018514996A JP2018530650A JP 2018530650 A JP2018530650 A JP 2018530650A JP 2018514996 A JP2018514996 A JP 2018514996A JP 2018514996 A JP2018514996 A JP 2018514996A JP 2018530650 A JP2018530650 A JP 2018530650A
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- JP
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- Prior art keywords
- cerium oxide
- composition
- polymer
- amphiphile
- modified
- 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.)
- Granted
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- 239000002245 particle Substances 0.000 title claims abstract description 121
- DRVWBEJJZZTIGJ-UHFFFAOYSA-N cerium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Ce+3].[Ce+3] DRVWBEJJZZTIGJ-UHFFFAOYSA-N 0.000 title claims description 49
- 229910000420 cerium oxide Inorganic materials 0.000 claims abstract description 60
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 229920000642 polymer Polymers 0.000 claims abstract description 43
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 45
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical group CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 31
- 239000005977 Ethylene Substances 0.000 claims description 29
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 22
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
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- 238000002360 preparation method Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
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- 239000004711 α-olefin Substances 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 3
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- 159000000032 aromatic acids Chemical class 0.000 claims description 3
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- 229920001169 thermoplastic Polymers 0.000 claims description 2
- ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical compound [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 claims 1
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- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
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- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004627 transmission electron microscopy Methods 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 229920001780 ECTFE Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000002441 X-ray diffraction Methods 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
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- 239000011521 glass Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 239000010954 inorganic particle Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
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- 238000002834 transmittance Methods 0.000 description 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Chemical group CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Chemical group CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Chemical group CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 239000005642 Oleic acid Chemical group 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Chemical group CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- KTSFMFGEAAANTF-UHFFFAOYSA-N [Cu].[Se].[Se].[In] Chemical compound [Cu].[Se].[Se].[In] KTSFMFGEAAANTF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本出願は、2015年9月23日出願の欧州特許出願第15306477.9号の優先権を主張するものであり、その内容は、あらゆる目的のために参照により本明細書に完全に援用される。用語または表現の明確さに影響を与えるであろう本出願とこの欧州出願との間の何らかの矛盾がある場合、それは本出願のみに言及されるべきである。
H3CO−CH2−−(CH2CO)−CH2−(CH2CO)−CH2−COOH
などの、Rが1〜6個の炭素原子を有するアルキル基である、式R−(CH2CO) n−COOHのものなどの、炭化水素鎖中にエーテル結合を含有するカルボン酸の群から選択されてもよい。
のポリオキシエチレン化アルキルエーテルホスフェート、
または式(2):
のポリオキシエチレン化ジアルキルエーテルホスフェート
(式中:同一であっても異なってもよい、R1、R2およびR3は、特に、2〜20個の炭素原子を含有する、線状または分岐のアルキル基;フェニル基;アルキルアリール基、より特に、8〜12個の炭素原子を含有するアルキル鎖を特に持った、アルキルフェニル基;またはアリールアルキル基、より特に、フェニルアリール基を表し;nは、0〜12であり得る、エチレンオキシド単位の数を表し;Mは、水素、ナトリウムまたはカリウムを表す)
から選択することができる。
R4−(OC2H4)p−O−R5 (3)
(式中、R4は、特に、4〜20個の炭素原子を含有することができる線状または分岐のアルキル基であり;pは、1〜20、例えば2〜16、好ましくは3〜12の整数であり;R5は、−CH2COOHなどのカルボン酸残基である)
のポリオキシエチレン化アルキルエーテルカルボキシレ−トからなる群から選択することができる。
(kは、無次元の形状係数(k=0.9)であり;
λ(ラムダ)は、放射光の波長(CuのKα線 1.5406オングストローム)であり;
H:回折ピークの中間高さでの幅であり;
s:用いられる装置におよび回折角に依存する計測幅(補正係数)であり;sは、LaB6結晶の解析によって求めることができる。
θ:回折角である)
に基づいて求められる。
(式中、nは、測定において考慮に入れられる粒子の数であり、xiは、粒子iのサイズであり、
は、粒子のサイズの平均値
である)
で表される。
− d90は、粒子の90%がd90未満の直径を有する粒子サイズまたは直径であり;
− d10は、粒子の10%がd10未満の直径を有する粒子サイズまたは直径であり;
− d50は、粒子の平均サイズまたは直径である。
− テトラフルオロエチレン、ヘキサフルオロプロピレン、ペンタフルオロプロピレン、およびヘキサフルオロイソブチレンなどの、C2〜C8フルオロフルオロオレフィン;
− フッ化ビニル、1,2−ジフルオロエチレン、フッ化ビニリデンおよびトリフルオロエチレンなどの、C2〜C8含水素フルオロオレフィン;
− 式CH2=CH−Rf0(式中、Rf0は、C1〜C6フルオロアルキルまたは1つ以上のエーテル基を有するC1〜C6フルオロオキシアルキルである)のフルオロアルキルエチレン;
− クロロトリフルオロエチレンのような、クロロ−および/またはブロモ−および/またはヨード−C2〜C6フルオロオレフィン;
− 式CF2=CFORf1(式中、Rf1は、C1〜C6フルオロアルキル、例えば−CF3、−C2F5、−C3F7である)のフルオロアルキルビニルエーテル
である。
(a)30〜48モル%、好ましくは35〜45モル%のエチレンと;
(b)52〜70モル%、好ましくは55〜65モル%のクロロトリフルオロエチレン、テトラフルオロエチレンまたはそれらの混合物と;
(c)モノマー(a)および(b)の総量を基準として、0〜5モル%、好ましくは0〜2.5モル%の1つ以上のフッ素化および/または含水素コモノマーと
を含む。
(a)35〜47モル%のエチレンに由来する繰り返し単位;
(b)53〜65モル%のクロロトリフルオロエチレンに由来する繰り返し単位
に由来する繰り返し単位から本質的になるものである。
− 20〜65nmの平均サイズを有する酸化セリウム粒子と、改質酸化セリウムの総重量に対して4.0〜15.0重量%の少なくとも1種の両親媒性物質、好ましくはイソステアリン酸とを含む少なくとも0.5重量%、好ましくは少なくとも1.0重量%の改質酸化セリウム、および
− 上に詳述されたようなエチレンとクロロトリフルオロエチレンとの少なくとも1種のコポリマー
を含む。
水中の酸化セリウム(CeO2)の分散系を、国際公開第2008/043703号パンフレットに、より具体的には国際公開第2008/043703号パンフレットの実施例1に開示されている方法に従って調製した。この分散系は、30重量%のCeO2当量での濃度を有した。40gの乾燥CeO2(本明細書では以下、CeO2−30と言われる)と同等である容積を採取した(133.3gの溶液に相当する)。
10nmの(BETによって測定される)粒子サイズを有する酸化セリウム(CeO2)の分散系を、国際公開第2008/043703号パンフレットに、より具体的には国際公開第2008/043703号パンフレットの実施例1に開示されている方法に従って(異なるCeIV/CeIII比を用いるが)調製した。この分散系は、30重量%のCeO2当量での濃度を有した。40gの乾燥CeO2(本明細書では以下、CeO2−10と言われる)と同等である容積を採取した(133.3gの溶液に相当する)。
3nmの平均粒子サイズの粒子と33重量%の量でのイソステアリン酸とを含む改質CeO2を、国際公開第01/10545A号パンフレットの実施例2に記載されている手順に従って調製した。
比色分析測定は、波長400〜700nmの範囲でX−Rite Ci51/Ci52分光計(測定幾何学:d/8°、DRS分光エンジン、8mm視野/14mm照明;測定範囲0〜200%反射率)を用いて実施例1のおよび比較例1の改質CeO2の粉末に関して実施した。CIE94法に従ったL*a*b*値を表1(ここで、L*は明度を表し;a*は赤/緑軸を表し;b*は黄/青軸を表す)に報告する。
フィルムを、10nmの平均粒子サイズを有する非改質CeO2粒子(本明細書では以下、CeO2−10)を使って、および実施例2において調製された改質CeO2粒子を使って調製した。
原材料
− ECTFE:180℃の融点、18J/gの融解熱(ΔH2f)および3.4g/10分(225℃/2.16kgで測定される)のメルトフローインデックス(MFI)を有するエチレン/クロロトリフルオロエチレンコポリマー。
− 実施例1の改質CeO2。
Claims (23)
- 10nm〜90nmの平均粒子サイズを有する酸化セリウム粒子の形態にある改質酸化セリウム、および少なくとも1種のポリマーと、9〜50個の炭素原子を有し、任意選択的に官能基を有する、線状または分岐の、脂肪族または芳香族の、酸、ならびにそれらの塩および誘導体からなる群から選択される少なくとも1種の両親媒性物質とを含む組成物。
- 改質酸化セリウム粒子がポリマー中に分散している、請求項1に記載の組成物。
- 両親媒性物質が、10〜40個の炭素原子を有する線状または分岐の脂肪族カルボン酸およびそれらの塩からなる群から選択される、請求項1または2に記載の組成物。
- 両親媒性物質がイソステアリン酸である、請求項1〜3のいずれか一項に記載の組成物。
- 少なくとも1種の両親媒性物質が、改質酸化セリウム粒子の総重量に対して少なくとも0.5重量%、最大でも30.0重量%である、請求項1〜4のいずれか一項に記載の組成物。
- 酸化セリウム粒子が、15nm〜60nm、より特に20〜50nm、さらにより特に25〜45nmの平均粒子サイズを有する、請求項1〜5のいずれか一項に記載の組成物。
- 酸化セリウム粒子が、20〜65nm、好ましくは20〜50nmの平均サイズを有し、両親媒性物質が、改質酸化セリウムの総重量に対して4.0〜15.0重量%の間に含まれる量でのイソステアリン酸またはその塩である、請求項1に記載の組成物。
- 酸化セリウムがセリウム(IV)結晶性酸化物である、請求項1〜7のいずれか一項に記載の組成物。
- 酸化セリウム粒子が、平均粒子サイズの値の最大でも30%の標準偏差を有する、請求項1〜8のいずれか一項に記載の組成物。
- ポリマーが熱可塑性ポリマーである、請求項1〜9のいずれか一項に記載の組成物。
- ポリマーが、アルファ−オレフィンホモ−およびコポリマー、重縮合ポリマーならびにハロゲン化ポリマーからなる群から選択される、請求項1〜10のいずれか一項に記載の組成物。
- ポリマーが、フッ化ビニリデンに由来する繰り返し単位を含むポリマー、ならびにエチレンとクロロトリフルオロエチレンおよびテトラフルオロエチレンから選択される少なくとも1種のモノマーとに由来する繰り返し単位を含むポリマーからなる群から選択されるフッ素化ポリマーである、請求項1〜11のいずれか一項に記載の組成物。
- 改質酸化セリウムが、組成物の総重量に対して少なくとも0.5重量%、最大でも10.0重量%である、請求項1〜12のいずれか一項に記載の組成物。
- フィルムの形態の、請求項1〜13のいずれか一項に記載の組成物。
- フィルムの厚さが15〜800μm、好ましくは20〜600μm、より好ましくは25〜500μmである、請求項14に記載の組成物。
- 請求項1〜15のいずれか一項に記載の組成物を含む物品。
- 請求項16に記載の物品または請求項14もしくは15に記載のフィルムの形態の組成物を含む光起電性パネル。
- 請求項1、6〜9のいずれか一項に記載に定義される酸化セリウム粒子と、9〜50個の炭素原子を有し、任意選択的に官能基を有する、線状または分岐の、脂肪族または芳香族の、酸、ならびにそれらの塩および誘導体からなる群から選択される少なくとも1種の両親媒性物質とを含む改質酸化セリウム。
- 両親媒性物質がイソステアリン酸またはその塩である、請求項18に記載の改質酸化セリウム。
- 請求項18または19に記載の改質酸化セリウムの製造方法であって、前記方法が、液体媒体中の酸化セリウム粒子の組成物を提供する工程と;少なくとも1種の両親媒性物質を前記組成物に添加する工程と;液体媒体を除去する工程と;乾燥させる工程とを含む方法。
- 液体媒体中に分散した請求項18または19に記載の改質酸化セリウムを含む分散系。
- 請求項1〜15のいずれか一項に定義される組成物の調製のための請求項18または19に定義される改質酸化セリウムの使用。
- 改質酸化セリウムが液体媒体中に分散している、請求項22に記載の使用。
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