KR100546947B1 - 작용화 실리카, 이의 제조방법 및 이를 포함하는 피복재 - Google Patents
작용화 실리카, 이의 제조방법 및 이를 포함하는 피복재 Download PDFInfo
- Publication number
- KR100546947B1 KR100546947B1 KR1020010064204A KR20010064204A KR100546947B1 KR 100546947 B1 KR100546947 B1 KR 100546947B1 KR 1020010064204 A KR1020010064204 A KR 1020010064204A KR 20010064204 A KR20010064204 A KR 20010064204A KR 100546947 B1 KR100546947 B1 KR 100546947B1
- Authority
- KR
- South Korea
- Prior art keywords
- silica
- group
- same
- functionalized
- coatings
- Prior art date
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 25
- -1 3-methacryloxypropylsilyl groups Chemical group 0.000 claims abstract description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000003607 modifier Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000077 silane Inorganic materials 0.000 abstract description 3
- 239000011527 polyurethane coating Substances 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000005253 cladding Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- VXKUOGVOWWPRNM-UHFFFAOYSA-N 3-ethoxypropyl acetate Chemical compound CCOCCCOC(C)=O VXKUOGVOWWPRNM-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/3081—Treatment with organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/309—Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/10—Solid density
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/19—Oil-absorption capacity, e.g. DBP values
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Dental Preparations (AREA)
- Silicon Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Glass Compositions (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Silicon Polymers (AREA)
Abstract
Description
BET[㎡/g] 138 탬프트 밀도[g/ℓ] 52 pH 4.6 C 함량 5.7 건조 감량[%] 0.8 강열 감량[%] 9.7 DBP 수[%] 228 |
BET[㎡/g] 165 탬프트 밀도[g/ℓ] 53 pH 4.9 C 함량 5.5 건조 감량[%] 1.5 강열 감량[%] 8.7 DBP 수[%] 242 |
중량부 | ||
밀베이스 (millbase) | 세탈룩스(Setalux) C 1152 XX - 51.50%(제조원; Akzo Nobel) 부틸 아세테이트 98% 크실렌 에어로실(실시예 1에 따르는 실리카) | 53.3 6.7 6.7 5.0 |
합량 | 71.7 | |
락커 구성분 | 세탈룩스 C 1152 XX - 51.50%(제조원; Akzo Nobel) 크실렌 에톡시프로필 아세테이트 부틸글리콜 아세테이트 | 1.1 12.2 1.5 1.5 |
경화제 | 데스모듀어(Desmodur) N 75(제조원; Bayer) | 17.0 |
합량 | 105.0 |
Claims (3)
- 작용성 그룹인 3-메타크릴옥시프로필실릴 그룹, 글리시딜옥시프로필실릴 그룹 또는 3-메타크릴옥시프로필실릴 그룹과 글리시딜옥시프로필실릴 그룹 모두가 표면에 고정되어 있음을 특징으로 하는 작용화 실리카.
- 물 또는 묽은 산을 실리카에 먼저 분무하고, 적당한 혼합 용기 속에서 강력하게 혼합하면서 3-메타크릴옥시프로필트리알콕시실란, 글리시딜옥시프로필트리알콕시실란 및 이들의 혼합물로부터 선택된 표면 개질제를 분무한 다음, 이러한 성분들을 15 내지 30분 동안 재혼합하고, 100 내지 400℃에서 1 내지 6시간에 걸쳐서 열처리함을 특징으로 하는, 제1항에 따르는 작용화 실리카의 제조방법.
- 제1항에 따르는 작용화 실리카를 포함하는 피복재.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00122954A EP1199335B1 (de) | 2000-10-21 | 2000-10-21 | Funktionalisierte Kieselsäuren |
EP00122954.1 | 2000-10-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20020031047A KR20020031047A (ko) | 2002-04-26 |
KR100546947B1 true KR100546947B1 (ko) | 2006-02-01 |
Family
ID=8170158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020010064204A KR100546947B1 (ko) | 2000-10-21 | 2001-10-18 | 작용화 실리카, 이의 제조방법 및 이를 포함하는 피복재 |
Country Status (7)
Country | Link |
---|---|
US (1) | US6809149B2 (ko) |
EP (1) | EP1199335B1 (ko) |
JP (1) | JP2002194246A (ko) |
KR (1) | KR100546947B1 (ko) |
AT (1) | ATE492607T1 (ko) |
CA (1) | CA2359493A1 (ko) |
DE (1) | DE50016050D1 (ko) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10140155A1 (de) | 2001-08-16 | 2003-03-06 | Basf Coatings Ag | Thermisch sowie thermisch und mit aktinischer Strahlung härtbare Beschichtungsstoffe und ihre Verwendung |
CN100575403C (zh) * | 2002-07-02 | 2009-12-30 | 德古萨股份公司 | 液体硬质塑料 |
US20040039781A1 (en) * | 2002-08-16 | 2004-02-26 | Lavallee David Anthony | Peer-to-peer content sharing method and system |
DE10304849A1 (de) * | 2003-02-06 | 2004-08-19 | Institut für Neue Materialien gemeinnützige Gesellschaft mit beschränkter Haftung | Chemomechanische Herstellung von Funktionskolloiden |
US7622514B2 (en) * | 2005-05-09 | 2009-11-24 | Sabic Innovative Plastics Ip B.V. | Curable composition and article possessing protective layer obtained therefrom |
CN100460472C (zh) * | 2005-12-02 | 2009-02-11 | 中国科学院化学研究所 | 表面接枝有机功能分子的纳米二氧化硅及其制备方法 |
EP1801166A1 (de) | 2005-12-23 | 2007-06-27 | Degussa GmbH | Pyrogen hergestelltes silanisiertes Siliciumdioxid |
DE102006039273A1 (de) * | 2006-08-22 | 2008-02-28 | Evonik Degussa Gmbh | Pyrogenes Siliciumdioxid zur Verwendung als Hilfsstoff in pharmazeutischen und kosmetischen Zusammensetzungen |
US7868287B2 (en) * | 2006-08-30 | 2011-01-11 | The Texas A&M University System | Highly diffuse reflector |
DE102007024365A1 (de) * | 2007-05-22 | 2008-11-27 | Evonik Degussa Gmbh | Pyrogen hergestellte silanisierte und vermahlene Kieselsäure |
DE102007024095A1 (de) * | 2007-05-22 | 2008-11-27 | Evonik Degussa Gmbh | Hydrophobe pyrogen hergestellte Kieselsäure und Silikonkautschukmassen, enthaltend die pyrogene Kieselsäure |
DE102007041857A1 (de) * | 2007-09-03 | 2009-03-05 | Wacker Chemie Ag | Verfahren zur kontinuierlichen Herstellung von vernetzbaren Massen auf der Basis von Organosiliciumverbindungen |
EP2070992A1 (de) * | 2007-12-11 | 2009-06-17 | Evonik Degussa GmbH | Lacksysteme |
EP2072028A1 (de) * | 2007-12-21 | 2009-06-24 | Ernst Mühlbauer GmbH & Co.KG | Stumpfaufbaumaterial |
EP2231758A1 (en) * | 2007-12-21 | 2010-09-29 | Cabot Corporation | Filler system including densed fumed metal oxide |
AU2009232369A1 (en) * | 2008-04-01 | 2009-10-08 | The Sherwin-Williams Company | Curable compositions |
US8163357B2 (en) * | 2009-03-26 | 2012-04-24 | Signet Armorlite, Inc. | Scratch-resistant coatings with improved adhesion to inorganic thin film coatings |
US9290690B2 (en) | 2011-05-03 | 2016-03-22 | Preferred Technology, Llc | Coated and cured proppants |
US8763700B2 (en) | 2011-09-02 | 2014-07-01 | Robert Ray McDaniel | Dual function proppants |
US9725645B2 (en) | 2011-05-03 | 2017-08-08 | Preferred Technology, Llc | Proppant with composite coating |
FR2985729B1 (fr) | 2012-01-18 | 2015-04-03 | Sardou Sa | Composite a nanofractales dendritiques fonctionnalisees et procedes pour realiser ledit composite |
US9562187B2 (en) | 2012-01-23 | 2017-02-07 | Preferred Technology, Llc | Manufacture of polymer coated proppants |
WO2013156337A1 (en) | 2012-04-20 | 2013-10-24 | Evonik Degussa Gmbh | Reinforced epoxy resin adhesive |
US9518214B2 (en) | 2013-03-15 | 2016-12-13 | Preferred Technology, Llc | Proppant with polyurea-type coating |
US10100247B2 (en) | 2013-05-17 | 2018-10-16 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
CN103387757B (zh) * | 2013-07-25 | 2016-02-10 | 北京市建筑工程研究院有限责任公司 | 一种超临界中水滑石接枝阻燃剂的制备方法 |
DE102013224206A1 (de) | 2013-11-27 | 2015-05-28 | Wacker Chemie Ag | Oberflächenmodifizierte partikuläre Metalloxide |
US9790422B2 (en) | 2014-04-30 | 2017-10-17 | Preferred Technology, Llc | Proppant mixtures |
AR104606A1 (es) | 2015-05-13 | 2017-08-02 | Preferred Tech Llc | Partícula recubierta |
US9862881B2 (en) | 2015-05-13 | 2018-01-09 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
US11071297B2 (en) * | 2015-08-13 | 2021-07-27 | Basf Se | Nonaqueous pesticide suspension comprising a water soluble solvent, an inorganic thickener, and an alkoxylate |
US11208591B2 (en) | 2016-11-16 | 2021-12-28 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
US10696896B2 (en) | 2016-11-28 | 2020-06-30 | Prefferred Technology, Llc | Durable coatings and uses thereof |
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US5959005A (en) | 1996-04-26 | 1999-09-28 | Degussa-Huls Aktiengesellschaft | Silanized silica |
US6197863B1 (en) | 1997-07-31 | 2001-03-06 | Wacker-Chemie Gmbh | Crosslinkable powder composition which is redispersible in water |
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2000
- 2000-10-21 EP EP00122954A patent/EP1199335B1/de not_active Expired - Lifetime
- 2000-10-21 DE DE50016050T patent/DE50016050D1/de not_active Expired - Lifetime
- 2000-10-21 AT AT00122954T patent/ATE492607T1/de active
-
2001
- 2001-10-18 KR KR1020010064204A patent/KR100546947B1/ko active IP Right Grant
- 2001-10-19 US US09/982,006 patent/US6809149B2/en not_active Expired - Lifetime
- 2001-10-19 CA CA002359493A patent/CA2359493A1/en not_active Abandoned
- 2001-10-22 JP JP2001323487A patent/JP2002194246A/ja active Pending
Patent Citations (9)
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US4427823A (en) * | 1980-10-28 | 1984-01-24 | Mitsui Petrochemical Industries Ltd. | Cured or uncured filled coating composition of polyfunctional acrylic-type acid ester and utilization thereof |
US6096807A (en) * | 1993-07-06 | 2000-08-01 | Basf Coatings Ag | Powder coating, process for the exterior coating of metal pipes, and use of the powder coating for the one-layer exterior coating of metal pipes |
JPH07126549A (ja) * | 1993-11-05 | 1995-05-16 | Shin Etsu Chem Co Ltd | 表面処理シリカの製造方法 |
US5731372A (en) * | 1995-04-03 | 1998-03-24 | Nippon Paint Co., Ltd. | Rust inhibiting coating composition for zinc, zinc alloy plated or unplated steel |
KR100260325B1 (ko) * | 1996-04-26 | 2000-07-01 | 볼커 버그달 | 실란화 실리카 |
KR980002185A (ko) * | 1996-06-11 | 1998-03-30 | 성재갑 | 저장안정성, 내마모성 및 착색성이 우수한 실록산계 피복 조성물 |
EP0896029A1 (de) * | 1997-07-31 | 1999-02-10 | Wacker-Chemie GmbH | Vernetzbare in Wasser redispergierbare Pulverzusammensetzung |
US6355703B1 (en) * | 1997-12-12 | 2002-03-12 | Dsm N. V. | Liquid curable resin composition, coating, and cured coating therefrom |
US6478861B1 (en) * | 1999-06-25 | 2002-11-12 | Videojet Technologies Inc. | Laser markable coating |
Also Published As
Publication number | Publication date |
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ATE492607T1 (de) | 2011-01-15 |
JP2002194246A (ja) | 2002-07-10 |
US20020077407A1 (en) | 2002-06-20 |
CA2359493A1 (en) | 2002-04-21 |
EP1199335A1 (de) | 2002-04-24 |
EP1199335B1 (de) | 2010-12-22 |
KR20020031047A (ko) | 2002-04-26 |
US6809149B2 (en) | 2004-10-26 |
DE50016050D1 (de) | 2011-02-03 |
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