JP5788336B2 - 反応副生成物の濃度が低い水性シルセスキオキサン分散液 - Google Patents
反応副生成物の濃度が低い水性シルセスキオキサン分散液 Download PDFInfo
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- 239000006185 dispersion Substances 0.000 title claims description 43
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- 238000006243 chemical reaction Methods 0.000 title description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 34
- 239000002245 particle Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- 239000007822 coupling agent Substances 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
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- 150000001343 alkyl silanes Chemical class 0.000 description 3
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
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- 239000012855 volatile organic compound Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 150000001412 amines Chemical group 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
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- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
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- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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Description
本出願は、2009年3月13日付けで出願した米国仮出願番号61/159825による優先権の利点を請求するものである。
従って、シルセスキオキサン分散液の安定性を維持しながら上述した如き溶解している副生成物を前記分散液から除去するに有効かつ効果的な手段が必要とされている。
組成物の製造方法が提供される。この方法は、i)a)シリカ、b)アンモニウムではない非揮発性カチオンおよびc)水を含有して成る粒子分散液を生じさせ、ii)式R1−(R2−O)3−Si[式中、R1は、置換アルキルおよび非置換アルキルから成る群より選択され、そしてR2は、メチル、エチル、プロピルおよびブチルから成る群より選択されるが、R1の置換アルキルはアミノアルキルではない]で表される少なくとも1種の有機シリルカップリング剤を添加して、iii)前記有機シリルカップリング剤と前記
粒子分散液を反応させることでシルセスキオキサンおよびアルコールを含有して成る混合物を生じさせ、そしてiv)前記アルコールを前記混合物から真空蒸留で最終的アルコール濃度が総混合物の約1重量%以下になるように除去することを含んで成る。場合により、前記最終的アルコール濃度を総混合物の約0.5重量%以下にしてもよく、それには総混合物の約1000ppm以下が含まれる。そのような分散液をまたゾルと呼ぶこともあり得る。本方法で生じさせた組成物は布地の処理で使用可能であり、それにはカーペットの処理が含まれる。
2−OHが媒体の中に遊離して来る。その媒体にまた元々の粒子を安定に分散させる(シリカまたは他の粒子を出発材料として用いる場合)か或は生じさせる粒子の生成および分散を支持する1種以上の作用剤も入れておいてもよい。
ポキシシランを反応体として用いた場合にも同様な条件下でエタノールもしくはプロパノールを高い分率で除去することができる。また、比較的高い揮発性を示す他の副生成物も同時に除去され得る。そのような副生成物および他の揮発物が除去される度合は、用いる具体的条件(温度、真空度および時間)に依存する。如何なる場合でも、結果として残存する揮発性有機化合物の濃度が実質的に低下した安定な分散液がもたらされる。
質量スペクトル検出器が備わっているガスクロマトグラフィ(GC−MS)を用いて水性分散液中に存在する副生成物であるアルコールの量を真空蒸留工程前および後に測定した。その分散液に残存するアルコールを酢酸エチルによる抽出で優先的に除去した。その抽出液を濾過して微粒子を除去した後、メタノールの相対的濃度をGC−MSで測定して、通常の標準添加方法を用いて既知標準と比較した。
20リットルの反応槽にGraceDavidsonのLudox AS−40(これは平均粒径が約20から30nmのシリカ粒子が水にシリカ量が約40重量%になるように懸濁していてアンモニウムによる安定化を受けた名目上のpHが9の懸濁液であると記述)を約1.2kg入れた。その粒子懸濁液と30gのメチルトリメトキシシランを約30℃でゆっくり反応させることでアルキルシラン改質粒子(これをシリカ−コアシルセスキオキサンと呼ぶことができる)の水性懸濁液を生じさせたが、それのメタノール濃度は約1重量%であった。約40℃でゆっくりした撹拌を維持しながら真空を約50トールの圧力になるように約4時間かけることでメタノールを徐々に除去した。固体が有意な量で沈澱することを確認し、このことは、粒子が凝集を起こしかつ安定な粒子分散液の破壊が始まったことを示している。
20リットルの反応槽にGraceDavidsonのLudox TM−40(これは平均粒径が約20から30nmのシリカ粒子が水にシリカ量が約40重量%になるように懸濁していてナトリウムによる安定化を受けた名目上のpHが9の懸濁液であると記述)を約1.2kg入れた。その粒子懸濁液と30gのメチルトリメトキシシランを約30℃でゆっくり反応させることでアルキルシラン改質粒子(これをシリカ−コアシルセスキオキサンと呼ぶことができる)の水性懸濁液を生じさせたが、それのメタノール濃度は約1重量%であった。約50トールの圧力下約40℃でゆっくりした撹拌を維持することでメタノールを徐々に除去した。約10時間後の溶液中に残存するメタノールの量は100
ppm未満であることを確認した。粒子の凝集はほとんど観察されなかった。
Claims (9)
- 組成物の製造方法であって、
i)a)シリカ、b)リチウム、ナトリウム、カリウム、セシウム、マグネシウムおよびカルシウムから成る群より選択される少なくとも1種のカチオン、および、c)水を含有して成る粒子分散液を生じさせるステップ、
ii)前記分散液に式R1−(R2−O)3−Si[式中、R1は、置換アルキルおよび非置換アルキルから成る群より選択され、そしてR2は、メチル、エチル、プロピルおよびブチルから成る群より選択されるが、R1の置換アルキルはアミノアルキルではない]で表される少なくとも1種の有機シリルカップリング剤を添加するステップ、
iii)前記有機シリルカップリング剤と前記粒子分散液を反応させることで、シルセスキオキサンおよびアルコールを含有して成る混合物を生じさせるステップ、そして
iv)前記アルコールを、前記混合物から真空蒸留で、最終的アルコール濃度が総混合物の1重量%以下になるように除去するステップ、
を含んで成る方法。 - 前記最終的アルコール濃度を総混合物の0.5重量%以下にする請求項1に記載の方法。
- 前記最終的アルコール濃度を総混合物の1000ppm以下にする請求項1に記載の方法。
- 前記カチオンを、リチウム、ナトリウム、カリウムおよびセシウムから成る群より選択する請求項1に記載の方法。
- R2をメチル、エチルおよびプロピルから成る群より選択する請求項1に記載の方法。
- R1をメチル、エチル、プロピルおよびブチルから成る群より選択する請求項1に記載の方法。
- R1がハロアルキルである請求項1記載の方法。
- v)ステップiv)で生じた生成物を、フルオロケミカル樹脂含有水性分散液と混合するステップ、を含んで成る請求項1から7のいずれかに記載の方法。
- 請求項1〜8のいずれかに記載の方法により得られた組成物をカーペットに適用し、その後乾燥させることを特徴とするカーペットの処理方法。
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US15982509P | 2009-03-13 | 2009-03-13 | |
US61/159,825 | 2009-03-13 | ||
PCT/US2010/027008 WO2010105071A2 (en) | 2009-03-13 | 2010-03-11 | Aqueous silsesquioxane dispersions having low concentrations of reaction byproducts |
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JP5788336B2 true JP5788336B2 (ja) | 2015-09-30 |
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US (2) | US8420734B2 (ja) |
EP (1) | EP2406268B1 (ja) |
JP (1) | JP5788336B2 (ja) |
AU (1) | AU2010224097B2 (ja) |
CA (1) | CA2755206C (ja) |
DK (1) | DK2406268T3 (ja) |
NZ (1) | NZ595058A (ja) |
WO (1) | WO2010105071A2 (ja) |
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US20140243452A1 (en) * | 2011-07-29 | 2014-08-28 | David A. Smetana | Dispersions and related coatings and cured articles |
CN108774413A (zh) * | 2018-04-13 | 2018-11-09 | 太仓运通新材料科技有限公司 | 纳米二氧化硅分散液及其制备方法 |
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US3620823A (en) * | 1969-05-19 | 1971-11-16 | Monsanto Co | Process of improving the resistance of soiling of melt spun fibers |
US3986997A (en) * | 1974-06-25 | 1976-10-19 | Dow Corning Corporation | Pigment-free coating compositions |
US4355135A (en) * | 1981-11-04 | 1982-10-19 | Dow Corning Corporation | Tintable abrasion resistant coatings |
US4617057A (en) * | 1985-06-04 | 1986-10-14 | Dow Corning Corporation | Oil and water repellent coating compositions |
US6225403B1 (en) | 1999-02-03 | 2001-05-01 | Barry R. Knowlton | Method and composition for treating fibrous substrates to impart oil, water and dry soil repellency |
US6468587B2 (en) * | 2000-06-30 | 2002-10-22 | 3M Innovative Properties Company | Treatment of fibrous substrates with acidic silsesquioxanes emulsions |
US6736857B2 (en) * | 2001-05-25 | 2004-05-18 | 3M Innovative Properties Company | Method for imparting soil and stain resistance to carpet |
JP3922343B2 (ja) * | 2001-08-07 | 2007-05-30 | 信越化学工業株式会社 | シリカ系及び/またはシルセスキオキサン系微粒子の水性分散液及びその製造方法 |
KR100929229B1 (ko) * | 2002-11-28 | 2009-12-01 | 엘지전자 주식회사 | 드럼 세탁기 도어 열림 제어방법 |
US7320956B2 (en) * | 2004-04-01 | 2008-01-22 | 3M Innovative Properties Company | Aqueous cleaning/treatment composition for fibrous substrates |
US20060115439A1 (en) | 2004-11-04 | 2006-06-01 | L'oreal | Compositions containing at least one silicone resin and glass beads |
CN101180344B (zh) | 2005-03-24 | 2012-01-11 | 株式会社普利司通 | 具有低挥发性有机化合物(voc)释放的配混二氧化硅补强橡胶 |
DE102007012578A1 (de) | 2006-09-01 | 2008-03-06 | Bühler PARTEC GmbH | Kationisch stabilisierte wässrige Silicadispersion, Verfahren zu deren Herstellung und deren Verwendung |
US7879743B2 (en) | 2006-10-01 | 2011-02-01 | Bigsky Technologies Llc | Stain and soil resistant textile article |
NZ580818A (en) * | 2007-05-18 | 2012-09-28 | Invista Tech Sarl | Method and composition for treating fibrous substrates |
US7915368B2 (en) * | 2007-05-23 | 2011-03-29 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes |
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CA2755206C (en) | 2014-08-19 |
EP2406268A2 (en) | 2012-01-18 |
CA2755206A1 (en) | 2010-09-16 |
WO2010105071A2 (en) | 2010-09-16 |
DK2406268T3 (en) | 2018-08-13 |
EP2406268A4 (en) | 2013-06-26 |
EP2406268B1 (en) | 2018-05-30 |
US20100233418A1 (en) | 2010-09-16 |
US9347174B2 (en) | 2016-05-24 |
US20130260084A1 (en) | 2013-10-03 |
JP2012520318A (ja) | 2012-09-06 |
US8420734B2 (en) | 2013-04-16 |
WO2010105071A3 (en) | 2011-01-20 |
AU2010224097A1 (en) | 2011-09-29 |
NZ595058A (en) | 2014-05-30 |
AU2010224097B2 (en) | 2016-05-05 |
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