WO2007087987A1 - Polyurethan-giesselastomere aus nco-prepolymeren auf basis von 2,4'-mdi, ein verfahren zu ihrer herstellung und ihre verwendung - Google Patents

Polyurethan-giesselastomere aus nco-prepolymeren auf basis von 2,4'-mdi, ein verfahren zu ihrer herstellung und ihre verwendung Download PDF

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Publication number
WO2007087987A1
WO2007087987A1 PCT/EP2007/000446 EP2007000446W WO2007087987A1 WO 2007087987 A1 WO2007087987 A1 WO 2007087987A1 EP 2007000446 W EP2007000446 W EP 2007000446W WO 2007087987 A1 WO2007087987 A1 WO 2007087987A1
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WO
WIPO (PCT)
Prior art keywords
mdi
nco
prepolymer
preparation
prepolymers
Prior art date
Application number
PCT/EP2007/000446
Other languages
German (de)
English (en)
French (fr)
Inventor
Hartmut Nefzger
Manfred Schmidt
James-Michael Barnes
Matthias Wintermantel
Original Assignee
Bayer Materialscience Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Materialscience Ag filed Critical Bayer Materialscience Ag
Priority to CA002640685A priority Critical patent/CA2640685A1/en
Priority to BRPI0707383-6A priority patent/BRPI0707383A2/pt
Priority to JP2008552712A priority patent/JP2009525363A/ja
Priority to EP07702879A priority patent/EP1981923A1/de
Publication of WO2007087987A1 publication Critical patent/WO2007087987A1/de

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group

Definitions

  • the present invention relates to new polyurethane (PUR) cast elastomers of NCO-functional prepolymers based on 2,4'-MDI and amine chain extenders and / or crosslinkers, a process for their preparation and their use.
  • PUR polyurethane
  • MDI diphenylmethane diisocyanate
  • polyisocyanates is a technically important group of polyisocyanates; it is structurally very heterogeneous in composition and comprises monomer types characterized by having two aromatic moieties joined by only one methylene bridge and higher oligomers having more than two aromatic moieties and more than one methylene bridge , which are referred to as polymeric MDI.
  • the ratio of monomer MDI to polymer MDI, as well as the proportions of the 2,4'- and 4,4'-isomers in the monomer MDI can be varied within wide limits by varying the synthesis conditions for the preparation of the precursor.
  • the separation of the crude MDI obtained in the MDI synthesis is carried out by distillation to a large extent, depending on the technical complexity of both almost isomerically pure fractions with fractions, e.g. can be separated from 4,4'-MDI greater than 97.5 wt .-% or isomer mixtures with 4,4'- and 2,4'-shares of about 50 wt .-%.
  • NCO prepolymers are NCO-terminated polyols, which are obtained by reacting a polyol with a polyisocyanate in, based on the NCO-reactive groups, molar NCO excess at room temperature to about 100 0 C. To this Manner-prepared NCO prepolymers always contain free, monomeric diisocyanate, depending on the molar ratios.
  • the driving force for the preparation of low-monomer, up to practically monomer-free NCO prepolymers is due in the case of 2,4-TDI in its high vapor pressure and the resulting health hazards. More critical in this context are those on the aliphatic diisocyanates, e.g. Hexamethylene diisocyanate (HDI) or isophorone diisocyanate (IPDI) based NCO prepolymers to see. This aspect is also present in MDI, but due to its lower vapor pressure compared to TDI to a significantly reduced extent. In addition, the reduction of the monomer content of the prepolymer results in polyurethanes which are softer than those prepared from monomer-containing NCO prepolymers.
  • HDI Hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • the preparation of low-monomer NCO prepolymers can be done in several different ways:
  • WO 01/40340 A2 (Crompton Corp.) gives examples of such combinations, wherein in a first step, the diisocyanate is reacted with the concomitant use of a selectivity-enhancing catalyst to form an NCO prepolymer, which is then freed from excess monomer by thin layers.
  • a selectivity-enhancing catalyst for particularly critical applications, such as in the food sector, the argument of occupational hygiene, which applies to a large extent to TDI, also applies to MDI.
  • the object of the present invention was therefore to provide polyurethanes based on 2,4'-MDI, which have advantages in terms of processing, for example in the form of extended casting times, lower prepolymer viscosities, compared to the prior art and at the same time in terms of their mechanical properties of the prior art at least equal.
  • NCO prepolymers so are made of pure 2,4'-MDI, at least 1 wt .-% and max. 20 wt .-%, based on prepolymer, free monomeric diisocyanate having and not extracted or distilled NCO prepolymers meant.
  • pure 2,4'-MDI is understood as meaning MDI types which have a content of 2,4'-isomer of at least 85% by weight, preferably at least 90% by weight, particularly preferably at least 95% by weight. , very particularly preferably at least 97.5 wt .-%.
  • the present invention provides polyurethane elastomers (obtainable by the casting process) obtainable from
  • the polyurethanes according to the invention are superior to the prior art because they have particularly favorable combinations of advantageous properties with respect to prepolymer viscosity, casting time, mechanical and mechanical-dynamic properties.
  • Another object of the invention is a process for the preparation of the erfindunssieen polyurethane elastomers according to the casting process, which is characterized in that
  • diphenylmethane diisocyanate having a 2,4'-isomer content of at least 85 wt .-%, preferably at least 90 wt .-%, more preferably at least
  • B) are added to the prepolymer from A) aminic chain extenders and / or crosslinkers and optionally auxiliaries and additives for the preparation of the elastomer.
  • the production of elastomers by the casting process is a generally important application of NCO-terminated prepolymers, wherein the prepolymers are reacted either directly after their preparation with a chain extender or cooled and stored the NCO prepolymers to a lower temperature (storage temperature) for the purpose of subsequent chain extension become.
  • the prepolymers are first degassed by applying a reduced pressure at room temperature or at elevated temperature and then - usually at elevated temperature - stirred with a chain extender.
  • the prepolymer is preferably heated to a temperature of 60 0 C to 1 10 ° C and degassed with stirring under vacuum.
  • the chain extender and / or crosslinker is added in liquid form, which is optionally heated to temperatures of typically at least 5 ° C above its melting point.
  • the reaction mixture is poured into preheated molds (preferably 90 0 C to 120 0 C) and baked for about 24 hours at 90 0 C to 140 0 C.
  • polyether As polyols, it is possible to use polyether, polyester, polycarbonate and polyetherester polyols having hydroxyl numbers of from 20 to 200 mg KOH / g, preferably from 27 to 150, particularly preferably from 27 to 120.
  • Polyether polyols are prepared either by alkaline catalysis or by double metal cyanide catalysis or optionally in stepwise reaction by alkaline catalysis and Doppelmetallcyanidkatalyse from a starter molecule and epoxides, preferably ethylene and / or propylene oxide and have terminal hydroxyl groups.
  • Suitable starters are the compounds with hydroxyl and / or amino groups known to those skilled in the art, as well as water. The functionality of the starter is at least 2 and at most 4. Of course, mixtures of multiple starters can be used.
  • mixtures of several polyether polyols can be used as polyether polyols.
  • Polyether polyols may be hydroxyl-terminated oligomers of tetrahydrofuran.
  • Polyester polyols are prepared in a conventional manner by polycondensation of alipahtic and / or aromatic polycarboxylic acids having 4 to 16 carbon atoms, optionally from their anhydrides and optionally from their low molecular weight esters, including ring esters, being used as the reaction component predominantly low molecular weight polyols having 2 to 12
  • Carbon atoms are used.
  • Polyester polyols here are preferably 2, but in individual cases may also be greater than 2, the components having functionalities greater than 2 being used only in small amounts, so that the arithmetic number average functionality of the polyester polyols is in the range from 2 to 2.5 2 to 2.1.
  • Polyetheresterpolyole be prepared by concomitant use of polyether polyols in polyester polyol synthesis.
  • Polycarbonate polyols are obtained according to the prior art from carbonic acid derivatives, for example dimethyl or diphenyl carbonate or phosgene and polyols by means of polycondensation. - o -
  • aromatic aminic chain extenders such as e.g. Diethyl toluenediamine (DETDA), 3,3'-dichloro-4,4'-diamino-diphenylmethane (MBOCA), 3,5-diamino-4-chloro-isobutylbenzoate, 4-methyl-2,6-bis (methylthio) -l, 3-diaminobenzene (Ethacure 300), trimethylene glycol di-p-aminobenzoate (Polacure 740M) and 4,4'-diamino-2,2'-dichloro-5,5'-diethyldiphenylmethane (MCDEA) , Particularly preferred are MBOCA and 3,5-diamino-4-chloro-isobutylbenzoate. Aliphatic aminic chain extenders may also be used or co-used.
  • DETDA Diethyl toluenediamine
  • MOCA 3,3'-dichlor
  • auxiliaries and additives such as catalysts, stabilizers, UV protectants, hydrolysis protectants, emulsifiers, preferably incorporable dyes and color pigments.
  • catalysts are trialkylamines, diazabicyclooctane, tin dioctoate, dibutyltin dilaurate, N-alkylmorpholine, lead, zinc, calcium, magnesium octoate, the corresponding naphthenates and p-nitrophenolate.
  • stabilizers are Broenstedt and Lewis acids, such as hydrochloric acid, benzoyl chloride, organomineric acids, e.g. Dibutyl phosphate, furthermore adipic acid, malic acid, succinic acid, grape acid or citric acid.
  • Lewis acids such as hydrochloric acid, benzoyl chloride, organomineric acids, e.g. Dibutyl phosphate, furthermore adipic acid, malic acid, succinic acid, grape acid or citric acid.
  • UV protectants and hydrolysis protectants are 2,6-dibutyl-4-methylphenol and sterically hindered carbodiimides.
  • Incorporatable dyes are those which have Zerewitinoff-active hydrogen atoms, so can react with NCO groups.
  • auxiliaries and additives include emulsifiers, foam stabilizers, cell regulators and fillers.
  • emulsifiers include emulsifiers, foam stabilizers, cell regulators and fillers.
  • foam stabilizers include emulsifiers, foam stabilizers, cell regulators and fillers.
  • polyurethane elastomers according to the invention can be used in a wide variety of applications: for example as elastic molded parts produced by the casting process, as well as in coatings and adhesives produced by a spraying process, e.g. in parking deck coatings, concrete repairs, corrosion protection.
  • Polyesterpolyol 1 poly (ethylene-co-butylene) adipate with an OH number of 56 mg KOH / g, Fa. Bayer MaterialScience AG; nominal functionality 2.0
  • 4,4'-MDI 4,4'-diisocyanate, Desmodur ® 44M from Bayer MaterialScience AG;. 98.5% by weight of 4,4'-isomer
  • 2,4'-MDI 2,4'-diphenylmethane diisocyanate (laboratory product) from Bayer MaterialScience AG; 98.5% by weight 2,4'-isomer
  • Table 1 Formulations of MDI-based ester prepolymers (according to the invention and comparative examples)
  • Prepolymer 1 from 100 parts by weight. Polyester polyol 1 and 25 parts by weight. 4,4'-MDI
  • Prepolymer 2 from 100 parts by weight. Polyester polyol 1 and 25 parts by weight. 2,4'-MDI
  • Table 2 Formulations, preparation and properties of the casting elastomers according to the invention
  • Example 3 Production of Non-Inventive Casting Elastomers from Prepolymers IV, 3V, 4V and 6V from Example 1 The preparation was carried out as described under Example 2
  • Tables 2 and 3 illustrates the advantages of the systems according to the invention: At comparable Prepolymertemperaturen (starting temperature) and comparable NCO contents, ie comparable formulations, the casting times of the prepolymers of the invention (Table 2) are up to a factor of 3 longer than those of the non-inventive systems (Table 3), which represents a significant processing advantage. The particularly favorable combinations of the properties "long casting time” and “low prepolymer viscosity" are only achieved by the systems according to the invention.
  • the cast elastomers according to the invention also have advantages with respect to their mechanical properties:
  • the systems according to the invention have a unique combination of advantageous properties with regard to prepolymer viscosity, casting time, mechanical and mechanical-dynamic properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/EP2007/000446 2006-02-01 2007-01-19 Polyurethan-giesselastomere aus nco-prepolymeren auf basis von 2,4'-mdi, ein verfahren zu ihrer herstellung und ihre verwendung WO2007087987A1 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002640685A CA2640685A1 (en) 2006-02-01 2007-01-19 Polyurethane cast elastomers formed from nco prepolymers based on 2,4'-mdi, a process for their preparation and their use
BRPI0707383-6A BRPI0707383A2 (pt) 2006-02-01 2007-01-19 elastÈmeros de fundição de poliuretano de pré-polìmeros nco à base de 2,4'-mdi, processo para sua preparação e seu uso
JP2008552712A JP2009525363A (ja) 2006-02-01 2007-01-19 ２，４’−ｍｄｉに基づくｎｃｏプレポリマーから形成されるポリウレタン注型エラストマー、その製造方法およびその使用
EP07702879A EP1981923A1 (de) 2006-02-01 2007-01-19 Polyurethan-giesselastomere aus nco-prepolymeren auf basis von 2,4'-mdi, ein verfahren zu ihrer herstellung und ihre verwendung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006004527A DE102006004527A1 (de) 2006-02-01 2006-02-01 Polyurethan-Gießelastomere aus NCO-Prepolymeren auf Basis von 2,4-MDI, ein Verfahren zu ihrer Herstellung und ihre Verwendung
DE102006004527.0 2006-02-01

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Country Status (11)

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EP (1) EP1981923A1 (zh)
JP (1) JP2009525363A (zh)
KR (1) KR20080097416A (zh)
CN (1) CN101379105A (zh)
BR (1) BRPI0707383A2 (zh)
CA (1) CA2640685A1 (zh)
DE (1) DE102006004527A1 (zh)
RU (1) RU2008135000A (zh)
TW (1) TW200740868A (zh)
WO (1) WO2007087987A1 (zh)
ZA (1) ZA200806596B (zh)

Cited By (8)

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WO2009065513A1 (de) * 2007-11-20 2009-05-28 Bayer Materialscience Ag Polyurethan-/polyharnstoff-elastomers auf basis von 2,4'-diphenylmethandiisocyanat-prepolymeren und ihre herstellung
WO2009118112A2 (de) * 2008-03-28 2009-10-01 Bayer Materialscience Ag 2,2'-mdi-basierte isocyanat-mischungen und ihre herstellung sowie verwendung
EP2455410A1 (de) * 2010-11-23 2012-05-23 Bayer MaterialScience AG Polyurethanelastomerformteile aus Diphenylmethandiisocyanat-basierten NCO-Prepolymeren und Metallsalzkomplexen und ein Verfahren zu ihrer Herstellung
EP3000834A1 (en) * 2014-09-29 2016-03-30 Fujifilm Corporation Flexible tube for an endoscope, adhesive for an endoscope, endoscope-type medical device, as well as method of producing a flexible tube for an endoscope and method of producing an endoscope-type medical device
CN112692725A (zh) * 2019-10-23 2021-04-23 Skc索密思株式会社 抛光垫用组合物及抛光垫
EP3835335A1 (en) 2019-12-12 2021-06-16 Covestro Deutschland AG Method for producing wood-based panels
EP4063423A1 (en) 2021-03-24 2022-09-28 Covestro Deutschland AG Method for preparing an artificial board
EP4223826A1 (en) 2022-02-08 2023-08-09 Covestro Deutschland AG Isocyanate composition and use thereof

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JP2008133343A (ja) * 2006-11-28 2008-06-12 Nippon Polyurethane Ind Co Ltd 主成分として２，４’−ｍｄｉを用いて得られるウレタンプレポリマーからなるウレタンエラストマー形成性組成物
KR100942359B1 (ko) * 2007-11-06 2010-02-12 주식회사 효성 열세트성이 향상된 폴리우레탄우레아 탄성사의 제조방법
DE102008012971A1 (de) 2008-03-06 2009-05-28 Bayer Materialscience Ag Polyurethan-Prepolymer und hieraus hergestellte Polyurethan/Polyurea-Elastomere
WO2011138275A1 (de) * 2010-05-07 2011-11-10 Bayer Materialscience Ag Polyurethanelastomere, ein verfahren zu ihrer herstellung und ihre verwendung
CN102181033A (zh) * 2011-03-28 2011-09-14 来安县安泰聚氨酯制品有限公司 一种聚氨酯剥片轮的工艺配方
EP2559716A1 (de) 2011-08-15 2013-02-20 Basf Se Polyurethangießharz
CN104245772B (zh) 2012-02-13 2017-08-11 陶氏环球技术有限责任公司 用于造纸设备的弹性体
CN103923457B (zh) * 2014-03-27 2016-08-17 黎明化工研究设计院有限责任公司 一种高耐磨聚氨酯弹性体及其制备方法
KR101919214B1 (ko) 2014-03-28 2018-11-15 호야 렌즈 타일랜드 리미티드 광학 부재용 폴리이소시아네이트 모노머 조성물, 광학 부재 및 그 제조 방법
CN109503804A (zh) * 2018-12-10 2019-03-22 山西省化工研究所（有限公司） 一种室温固化高性能聚氨酯弹性体组合物
KR20220080138A (ko) * 2019-10-09 2022-06-14 듀폰 폴리머스, 인크. 개선된 폴리에스테르

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009065513A1 (de) * 2007-11-20 2009-05-28 Bayer Materialscience Ag Polyurethan-/polyharnstoff-elastomers auf basis von 2,4'-diphenylmethandiisocyanat-prepolymeren und ihre herstellung
WO2009118112A2 (de) * 2008-03-28 2009-10-01 Bayer Materialscience Ag 2,2'-mdi-basierte isocyanat-mischungen und ihre herstellung sowie verwendung
WO2009118112A3 (de) * 2008-03-28 2010-01-21 Bayer Materialscience Ag 2,2'-mdi-basierte isocyanat-mischungen und ihre herstellung sowie verwendung
US8097675B2 (en) 2008-03-28 2012-01-17 Bayer Materialscience Ag 2,2′-MDI-based isocyanate mixtures, polyisocyanate polyaddition products prepared therefrom, processes for making the same and methods for their use
EP2455410A1 (de) * 2010-11-23 2012-05-23 Bayer MaterialScience AG Polyurethanelastomerformteile aus Diphenylmethandiisocyanat-basierten NCO-Prepolymeren und Metallsalzkomplexen und ein Verfahren zu ihrer Herstellung
WO2012069368A1 (de) * 2010-11-23 2012-05-31 Bayer Materialscience Ag Polyurethanelastomerformteile aus diphenylmethandiisocyanat basierten nco-prepolymeren und metallsalzkomplexen und ein verfahren zu ihrer herstellung
EP3000834A1 (en) * 2014-09-29 2016-03-30 Fujifilm Corporation Flexible tube for an endoscope, adhesive for an endoscope, endoscope-type medical device, as well as method of producing a flexible tube for an endoscope and method of producing an endoscope-type medical device
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CN112692725A (zh) * 2019-10-23 2021-04-23 Skc索密思株式会社 抛光垫用组合物及抛光垫
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EP1981923A1 (de) 2008-10-22
BRPI0707383A2 (pt) 2011-05-03
CN101379105A (zh) 2009-03-04
TW200740868A (en) 2007-11-01
DE102006004527A1 (de) 2007-08-09
ZA200806596B (en) 2009-10-28
RU2008135000A (ru) 2010-03-10
JP2009525363A (ja) 2009-07-09
KR20080097416A (ko) 2008-11-05
CA2640685A1 (en) 2007-08-09

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