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WO1999051692A1 - Agents de matite a base de silice revetue - Google Patents

Agents de matite a base de silice revetue Download PDF

Info

Publication number
WO1999051692A1
WO1999051692A1 PCT/EP1999/002160 EP9902160W WO9951692A1 WO 1999051692 A1 WO1999051692 A1 WO 1999051692A1 EP 9902160 W EP9902160 W EP 9902160W WO 9951692 A1 WO9951692 A1 WO 9951692A1
Authority
WO
WIPO (PCT)
Prior art keywords
matting agent
silicon dioxide
urea
moisture content
agent according
Prior art date
Application number
PCT/EP1999/002160
Other languages
English (en)
Inventor
Ute Pospesch
Horst Schneider
Georg Lüers
Original Assignee
Grace Gmbh
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 Grace Gmbh filed Critical Grace Gmbh
Priority to AU34187/99A priority Critical patent/AU3418799A/en
Publication of WO1999051692A1 publication Critical patent/WO1999051692A1/fr

Links

Classifications

    • 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
    • C09C1/3063—Treatment with low-molecular organic compounds
    • 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
    • C09D7/42—Gloss-reducing agents

Definitions

  • the present invention relates to coated matting agents, processes for their preparation and their use in paints and lacquers.
  • Silicon dioxide particles or silica gel particles are used, inter alia, as matting agents to achieve a micro-rough surface on coatings.
  • untreated silica gel particles often form hard sediments during storage. Attempts to redisperse these matting agents are usually difficult, and in many cases unsuccessful. This then often means that the gloss of coatings produced with such paints varies as the paint is used up, since some of the matting agent accumulates on the bottom of the container in which the paint or lacquer is stored.
  • additives such as bentonites , which form thixotropic structures and prevent sedimentation of the particles, are added by the paint manufacturer.
  • the manufacturer modifies the matting agents themselves, i.e. for example coats them with a wax chosen from the group consisting of polyolefins, mineral waxes, paraffins and the like. 5 to 10 wt.% wax, based on the matting agent, is usually used to form a matting agent which gives, in conventional paints and lacquers, soft sediments which can easily be redispersed. - 2 -
  • DE 10 06 100 thus discloses a process for the preparation of silica gel matting agents in which dried and ground silica gel is impregnated with microcrystalline wax which is insoluble in solvents for lacquers and the like. The process is carried out at temperatures above the melting point of the wax.
  • Another process for the preparation of matting agents is known from DE 15 92 865.
  • an aqueous emulsion or dispersion of an inert colourless high-melting wax or synthetic substances which is insoluble in lacquer solvents at room temperature is employed for modification of the silicic acids.
  • WO 95/31508 discloses a matting agent based on an amorphous silica gel having a certain pore size distribution, which is coated with specific waxes and has good matting properties, and a process for the preparation thereof.
  • EP-A-0 348 226 discloses a matting agent based on an inorganic hydrogel having a certain pore volume and content of volatile substances, and a specific average particle size and particle size distribution, so that a certain grinding fineness is obtained when it is dispersed in a coating composition.
  • EP-A-0 003 627 discloses a process for the preparation of a hydrophilic composition of urea, formaldehyde and an aqueous colloidal dispersion of silica particles, in which various mixing stages are carried out at certain pH values and the silica particles have an average size of 1 to 8 ⁇ m.
  • the compositions obtained by the process disclosed are used in photographic photosensitive silver halide material.
  • WO 97/12942 discloses a coating material which can be cured by irradiation or heat and consists of a composition which comprises chemically modified silicon dioxide particles.
  • the silicon dioxide particles are modified to the effect that organic compounds which contain polymeric unsaturated groups, (thio)urea - 3 -
  • silicon dioxide xerogel particles are usually coated with wax in a jet mill at temperatures above the melting point of the wax. During this operation, the molten wax is distributed homogeneously on the silicon dioxide particles.
  • the object of the present invention is thus to provide an efficient matting agent which, during storage in water-based paints and lacquers, forms soft sediments which can readily be redispersed. It is also an object of the present invention to provide a more efficient coating process for silicon dioxide particles, which is superior to the coating with wax known from the prior art.
  • a matting agent based on silicon dioxide which is characterized in that it comprises silicon dioxide particles which have a particle size of 2.5 to 20 ⁇ m and a moisture content of 0 to 65 wt.%, based on the matting agent, and are coated with 0.2 to 10 wt . % of a urea-urethane derivative or a mixture of urea-urethane derivatives of the general formula: - 4 -
  • the invention furthermore relates to a process for the preparation of a matting agent, which is characterized in that the urea-urethane derivative ( s ) of the formula (I) is/are added to the silicon dioxide during the micronization thereof.
  • urea-urethane derivatives according to the invention are also called the organic component or additive in the following.
  • the organic additive is thus in general a urea-urethane compound of low molecular weight.
  • R and R independently of one another are preferably
  • R is preferably
  • urea-urethane derivatives which are particularly preferred according to the invention are: . — . o o
  • the silicon dioxide component is preferably chosen from silicic acid hydrogels and/or silicic acid xerogels. These can be prepared by the sol-gel process or by the precipitation process.
  • the size of the silicon dioxide particles is preferably 5 to 15 ⁇ m, in particular 5 to 10 ⁇ m.
  • the silicon dioxide particles have a moisture content of 0 to 10 wt.%, in particular 0 to 5 wt.%, and preferably 1 to 3 wt . % , or 5 a moisture content of 30 to 65 wt.%, in particular 40 to 60 wt.%, and preferably about 50 wt.%, based on the matting agent.
  • a moisture content 0 to 10 wt.%, in particular 0 to 5 wt.%, and preferably 1 to 3 wt . % , or 5 a moisture content of 30 to 65 wt.%, in particular 40 to 60 wt.%, and preferably about 50 wt.%, based on the matting agent.
  • urea-urethane derivative of the formula (I) are preferably coated with 0.3 to 8 wt.%, in particular 0.5 to 3 wt . % urea-urethane derivative of the formula (I), based on the matting agent.
  • the matting agents according to the invention are in general prepared by adding the urea derivatives according to the invention to the silicon dioxide during comminution thereof. This can be carried out, for example, in a jet mill or in high-speed mixers (e.g. in a Henschel mixer).
  • the jet mill is preferably operated with a hot air supply.
  • the organic component is distributed in the form of very fine particles on the silica gel particles.
  • urea derivatives themselves can be prepared as disclosed in EP-A-0 006 252. They can advantageously be added in the form of organic solutions which contain 10 to 75 wt.%, preferably 30 to 60 wt.%, and in particular 45 to 55 wt.% urea-urethane derivative.
  • N-Methylpyrrolidone for example, can be used as the solvent.
  • BYK-410 from BYK Chemie GmbH, Wesel, which comprises the urea-urethanes of the - 7 -
  • the silicon dioxide or silica gel used in the process according to the invention can be prepared by the sol-gel process, as described, for example, in EP-A-0 384 226.
  • Hydrogels are employed according to the invention in particular.
  • Hydrogel matting agents have the advantage that they do not form dusts, because the pores are filled with water. Small amounts of surface water cause an adhesion of the particles to one another.
  • the hydrogel is micronized with hot air in a jet mill, dried to a moisture content of 30 to 65 wt.%, preferably 40 to 60 wt.%, in particular about 50 wt.%, and coated with the urea derivative.
  • a xerogel is employed, this is preferably micronized with hot air in a jet mill, adjusted to a moisture content of 0 to 10 wt.%, preferably 0 to 5 wt.%, in particular 1 to 3 wt.%, and coated with the urea derivative.
  • the new coating process as a rule requires only about 1 wt.% organic material, based on the matting agent, although less or more organic material can be employed according to the invention for the coating.
  • organic material based on the matting agent, although less or more organic material can be employed according to the invention for the coating.
  • concentrations of organic additive are therefore needed to allow the formation of soft sediments, which can readily be redissolved, in paints and lacquers.
  • 5 to 10 wt.% wax is needed to prevent the formation of hard sediments in water-based systems to a sufficient extent.
  • the process according to the invention therefore not only gives a cost advantage due to saving of material and lower process temperatures, but also increases the efficiency of the matting agent.
  • the efficiency of the material is higher, because the silicon dioxide content, which causes the matting, is higher. - 8 -
  • the urea-urethane derivative must in general be separated into individual molecules so that it has the maximum activity. This is typically achieved by dissolving it in solvents of moderate polarity.
  • the addition of the additive to the silica gel particles in the jet mill leads to deaggregation to very fine particles, regardless of the solvent.
  • These very fine particles of the organic component are bonded to the silica gel particles. This causes an inhomogeneous polarity of the particle surface and consequently only a loose agglomeration ( flocculation) during sediment formation.
  • the flocks are large enough to withstand the gravimetric forces in the sediment, and remain soft and, even after storage, readily dissolvable.
  • the matting agents according to the invention can therefore advantageously be used in water-based coatings, paints and lacquers and aqueous radiation-curing lacquer systems .
  • the pore volume of the particles was measured by adsorption of nitrogen using an ASAP 2400 nitrogen adsorption measuring instrument from Micro eritics .
  • the particle sizes were determined with the aid of the Malvern Mastersizer from Malvern Instruments Ltd.
  • the moisture content of the hydrogel was determined via the weight loss at a temperature of 160°C.
  • the moisture content of the xerogel was measured using a Karl-Fischer device. The percentages by weight stated relate to the weight of the end product (matting agent).
  • the carbon content was measured using a Leco SC 440 apparatus (D ⁇ sseldorf) and stated in per cent by weight, based on the silicon dioxide content in the end product. - 9 -
  • a silicic acid hydrogel having a moisture content of 65 wt.% was prepared and micronized in a jet mill operated with hot air.
  • the hot air temperature was 220°C and the amount introduced was 720 kg/h.
  • 2.6 1/h urea-urethane derivative BYK-410 commercial product from BYK Chemie GmbH Wesel
  • the resulting product had a particle size of 8 ⁇ m, a water content of 54.5% and a carbon content of 0.56 wt.% (corresponding to an additive concentration of about 0.7 wt.%).
  • a silicic acid hydrogel having a moisture content of 65 wt.% was micronized to a particle size of 8.0 ⁇ m and a water content of 56.3 wt.% in a jet mill with a hot air supply. In contrast to example 1, however, no coating was carried out.
  • the non-coated hydrogel matting agents (comparison example 1) formed a hard sediment which could no longer be dispersed by shaking. It was possible to remove the sediment from the bottom of the vessel only by using a spatula.
  • the hydrogel coated with BYK-410 (example 1) formed a sediment which could be redispersed very easily. The sediment already became detached from the bottom of the vessel by merely turning the vessel over.
  • a silica acid xerogel prepared by the sol-gel process and having a moisture content of about 1 wt . % and a particle size of 0.1 to 3 mm was mixed with BYK-410 in a Henschel mixer of the type FM 10L. 7.5 g of the organic compound were added to 750 g silica gel while stirring at 1,000 rpm for 10 minutes. When the addition had ended, mixing was continued for 10 minutes at 2,500 rpm. The mixture was micronized to a particle size of 5 ⁇ m in a fluidized bed jet mill of the type Alpine AFG 100.
  • the grinding conditions used here were:
  • a product having a particle size of 5.49 ⁇ m, a carbon content of 0.66 wt.% and a moisture content of 2.7 wt.% was obtained.
  • the product thus obtained had a particle size of 5.5 ⁇ m, a carbon content of ⁇ 0.2 wt.% and a moisture content of 1.34 wt.%.
  • a wax-coated comparison material was prepared on a production scale by grinding silicic acid xerogel in an air jet mill with simultaneous addition of wax into the jet mill.
  • the silica gel was fed in at 350 kg/h and the wax at 30 kg/h.
  • the other grinding conditions were:
  • a product having a particle size of 5.56 ⁇ m, a carbon content of 7.5 wt.% and a moisture content of 1.3 wt.% was obtained.
  • comparison example 2 and comparison example 3 were incorporated into 100 g Senosol Hydro-Glanzlack in the same manner as described under example 1 and comparison example 1.
  • the sedimentation of the particles was also investigated as in example 1. After 6 weeks, the consistency of the sediments was evaluated as follows .
  • Example 2 The product according to the invention formed a sediment which could be redispersed very easily. The sediment could already be detached from the bottom merely by turning the vessel over. - 12 -
  • Comparison example 2 The non-coated product formed a hard sediment which could be detached from the bottom again only using a spatula.
  • Comparison example 3 The product coated with wax formed a hard sediment which could be redispersed by vigorously shaking the vessel .
  • the comparison shows the clearly improved properties of a coating with 1 wt . % BYK-410 compared with a coating with 10 wt.% wax and non-coated matting agent.
  • comparison example 2 and comparison example 3 were incorporated into a conventional nitrocellulose paint (WACOCELL S 689).
  • 2 g of the matting agent were incorporated into 100 g nitrocellulose paint using a dissolver at 3,000 rpm for 10 minutes, the mixture was introduced into 100 ml vessels and these were closed and stored in the laboratory at room temperature for 6 weeks. After this time, the consistency of the sediments formed from the matting agent particles was investigated:
  • Example 2 The product coated according to the invention formed a hard sediment which was comparable to that of the product from comparison example 2.
  • Comparison example 2 The non-coated matting agent formed a hard sediment which could be dispersed only with great difficulty.
  • Comparison example 3 The dispersing agent coated with wax formed a sediment which could be redispersed very easily. The sediment could already be detached from the bottom by turning the vessel over. - 13 -

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Silicon Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

La présente invention concerne un agent de matité à base de silice (dioxyde de silicium). Le calibre des particules de silice se situe entre 2,5 et 20 νm. La teneur en eau est comprise entre 0 % et 65 % de la masse de l'agent de matité. L'ensemble est protégé par une couche d'un dérivé urée-uréthane, ou d'un mélange de dérivés urée-uréthane, à raison de 0,2 à 10 % de la masse.
PCT/EP1999/002160 1998-04-03 1999-03-30 Agents de matite a base de silice revetue WO1999051692A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU34187/99A AU3418799A (en) 1998-04-03 1999-03-30 Matting agents based on coated silicon dioxide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19816362.2 1998-04-03
DE19816362A DE19816362A1 (de) 1998-04-03 1998-04-03 Mattierungsmittel auf Basis von beschichtetem Siliciumdioxid

Publications (1)

Publication Number Publication Date
WO1999051692A1 true WO1999051692A1 (fr) 1999-10-14

Family

ID=7864398

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/002160 WO1999051692A1 (fr) 1998-04-03 1999-03-30 Agents de matite a base de silice revetue

Country Status (4)

Country Link
AU (1) AU3418799A (fr)
DE (1) DE19816362A1 (fr)
TW (1) TW500779B (fr)
WO (1) WO1999051692A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001066515A1 (fr) * 2000-03-02 2001-09-13 Asahi Kasei Kabushiki Kaisha Substance chromogene et materiau d'enregistrement
US6797771B2 (en) * 2000-02-02 2004-09-28 Basf Coatings Ag Aqueous composition that can be hardened physically, thermally or thermally and with actinic radiation and the derivatives and production thereof
RU2245873C2 (ru) * 2000-03-02 2005-02-10 Асахи Касеи Кабусики Кайся Новые цветообразующие композиции и записывающий материал
CN1330714C (zh) * 2005-01-18 2007-08-08 武汉理工大学 可诱导聚氯乙烯结晶的纳米二氧化硅制备方法
US7635662B2 (en) 1998-09-04 2009-12-22 Chemipro Kasei Kaisha, Ltd. Compound for color-producing composition, and recording material
CN101003499B (zh) * 2000-03-02 2011-01-19 Chemipro化成株式会社 生色组合物和记录材料
DE102009045109A1 (de) 2009-09-29 2011-03-31 Evonik Degussa Gmbh Oberflächenmodifizierte Semi-Gele
CN101585977B (zh) * 2009-06-12 2012-12-19 武汉理工大学 一种聚丙烯增强增韧改性剂的制备方法
WO2020159916A1 (fr) 2019-02-01 2020-08-06 W.R. Grace & Co.-Conn. Agents de matage à base de silice et leurs procédés de production et d'utilisation
WO2021041101A1 (fr) 2019-08-30 2021-03-04 W. R. Grace & Co.-Conn. Formulations matifiantes à base de silice et procédés pour les fabriquer et les utiliser
US11999857B2 (en) 2017-06-02 2024-06-04 W.R. Grace & Co.-Conn. Coated particles and methods of making and using the same
US12203006B2 (en) 2017-08-03 2025-01-21 W.R. Grace & Co.-Conn. Silica-based matting agents and methods of making and using the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE502004004410D1 (de) 2003-05-14 2007-09-06 Degussa Oberflächenmodifizierte Fällungskieselsäuren
US7560587B2 (en) * 2004-12-04 2009-07-14 Xerox Corporation Bis[urea-urethane] compounds

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314924A (en) * 1978-05-26 1982-02-09 Byk-Mallinckrodt Chemische Produkte Gmbh Thixotropic agent for use in coating compositions
US4857111A (en) * 1987-03-04 1989-08-15 Byk-Chemie Gmbh Thixotropic formulations, use of polycarboxylic acid amides to produce them, and silica coated with polycarboxylic acid amides
EP0384226A1 (fr) * 1989-02-15 1990-08-29 W.R. Grace & Co.-Conn. Agent mattant minéral en hydrogel
EP0442325A1 (fr) * 1990-02-14 1991-08-21 Grace GmbH Agent de matité à base de silice, procÀ©dé de fabrication et d'utilisation
WO1996034062A1 (fr) * 1995-04-26 1996-10-31 Grace Gmbh Agent de matite a base de silice agregee

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4032619C3 (de) * 1990-10-15 1998-01-08 Grace Gmbh Si0¶2¶-Mattierungsmittel, Verfahren zu dessen Herstellung und dessen Verwendung
JP3474330B2 (ja) * 1995-10-03 2003-12-08 Ｊｓｒ株式会社 反応性シリカ粒子、その製法および用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314924A (en) * 1978-05-26 1982-02-09 Byk-Mallinckrodt Chemische Produkte Gmbh Thixotropic agent for use in coating compositions
US4857111A (en) * 1987-03-04 1989-08-15 Byk-Chemie Gmbh Thixotropic formulations, use of polycarboxylic acid amides to produce them, and silica coated with polycarboxylic acid amides
EP0384226A1 (fr) * 1989-02-15 1990-08-29 W.R. Grace & Co.-Conn. Agent mattant minéral en hydrogel
EP0442325A1 (fr) * 1990-02-14 1991-08-21 Grace GmbH Agent de matité à base de silice, procÀ©dé de fabrication et d'utilisation
WO1996034062A1 (fr) * 1995-04-26 1996-10-31 Grace Gmbh Agent de matite a base de silice agregee

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7635662B2 (en) 1998-09-04 2009-12-22 Chemipro Kasei Kaisha, Ltd. Compound for color-producing composition, and recording material
US7807738B2 (en) 1998-09-04 2010-10-05 Chemipro Kasei Kaisha, Ltd. Compound for color-producing composition, and recording material
US6797771B2 (en) * 2000-02-02 2004-09-28 Basf Coatings Ag Aqueous composition that can be hardened physically, thermally or thermally and with actinic radiation and the derivatives and production thereof
AU779924B2 (en) * 2000-03-02 2005-02-17 Chemipro Kasei Kaisha, Limited Novel color former and recording material
WO2001066515A1 (fr) * 2000-03-02 2001-09-13 Asahi Kasei Kabushiki Kaisha Substance chromogene et materiau d'enregistrement
RU2245873C2 (ru) * 2000-03-02 2005-02-10 Асахи Касеи Кабусики Кайся Новые цветообразующие композиции и записывающий материал
CN101003499B (zh) * 2000-03-02 2011-01-19 Chemipro化成株式会社 生色组合物和记录材料
CN1330714C (zh) * 2005-01-18 2007-08-08 武汉理工大学 可诱导聚氯乙烯结晶的纳米二氧化硅制备方法
CN101585977B (zh) * 2009-06-12 2012-12-19 武汉理工大学 一种聚丙烯增强增韧改性剂的制备方法
DE102009045109A1 (de) 2009-09-29 2011-03-31 Evonik Degussa Gmbh Oberflächenmodifizierte Semi-Gele
WO2011038992A1 (fr) 2009-09-29 2011-04-07 Evonik Degussa Gmbh Semi-gels d'acide silicique modifiés en surface
US11999857B2 (en) 2017-06-02 2024-06-04 W.R. Grace & Co.-Conn. Coated particles and methods of making and using the same
US12203006B2 (en) 2017-08-03 2025-01-21 W.R. Grace & Co.-Conn. Silica-based matting agents and methods of making and using the same
WO2020159916A1 (fr) 2019-02-01 2020-08-06 W.R. Grace & Co.-Conn. Agents de matage à base de silice et leurs procédés de production et d'utilisation
WO2021041101A1 (fr) 2019-08-30 2021-03-04 W. R. Grace & Co.-Conn. Formulations matifiantes à base de silice et procédés pour les fabriquer et les utiliser

Also Published As

Publication number Publication date
DE19816362A1 (de) 1999-10-07
AU3418799A (en) 1999-10-25
TW500779B (en) 2002-09-01

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