CA1053395A - Process for the production of paint compositions - Google Patents
Process for the production of paint compositionsInfo
- Publication number
- CA1053395A CA1053395A CA191,688A CA191688A CA1053395A CA 1053395 A CA1053395 A CA 1053395A CA 191688 A CA191688 A CA 191688A CA 1053395 A CA1053395 A CA 1053395A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- polymer
- monomer
- pigment
- parts
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A paint composition comprising pigment particles coated with a polymer is produced which has improvements in uniformity of particle size and dispersion of pigment particles as compared with presently available paints. This paint composition is obtained by contacting a finely divided pigment with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bisulfite ions. The polymerization proceeds spontan-eously with the pigment particles and bisulfite ions acting as polymerization initiator.
A paint composition comprising pigment particles coated with a polymer is produced which has improvements in uniformity of particle size and dispersion of pigment particles as compared with presently available paints. This paint composition is obtained by contacting a finely divided pigment with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bisulfite ions. The polymerization proceeds spontan-eously with the pigment particles and bisulfite ions acting as polymerization initiator.
Description
S~3~5 This invention relates to an improved process for the preparation of paint compositions. ~lore particularly, the pres-ent invention relates to an improved process for preparing a paint composition composed of an emulsion containing polymer-coated pigment particles in the dispersed state.
There have heretofore been known a process for preparing a polymer composition comprising a pigment such as filler pigments, inorganic pigments, metal pigments and carbon black by utilizing a Friedel-Crafts catalyst (see Japanese Patent Publication No.
6985/62 to Continental Oil Company) and a process for preparing an emulsion by polymerizing a vinyl monomer in water in which a white inorganic pigment incorporated with an organic chelating agent is dispersed (see ~apanese Patent Publication No. 14584t~6 to Kobunshi-Kagaku Kogyo Kabushiki l~aisha).
However, since in each of these compositions comprising a pigment and a polymer, which are prepared according to these known processes, the pigment and polymer are in the merely mixed state, such undesired phenomena as heterogeneous dispersion of the pigment and non-uniformity of the particle size cannot be avoided.
20 Accordingly, when these compositions are used as paints, such un-desired defec~s as uneven color concentration and for~ation of pigment specks are brought about.
It is the object of this invention to provide a paint composition which overcomes the above defects and provides homo-geneous pigment particles in a uniformty dispersed state.
In accordance with this invention, the above object is achieved by contacting a finely divided pigment other than elemental carbon-containing material with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bi-30 sulfite ions (also called acid sulfite ions) in the absence of r additional polymerization initiators. The pigment particles themselves in combination with the bisulfite ions act as a
There have heretofore been known a process for preparing a polymer composition comprising a pigment such as filler pigments, inorganic pigments, metal pigments and carbon black by utilizing a Friedel-Crafts catalyst (see Japanese Patent Publication No.
6985/62 to Continental Oil Company) and a process for preparing an emulsion by polymerizing a vinyl monomer in water in which a white inorganic pigment incorporated with an organic chelating agent is dispersed (see ~apanese Patent Publication No. 14584t~6 to Kobunshi-Kagaku Kogyo Kabushiki l~aisha).
However, since in each of these compositions comprising a pigment and a polymer, which are prepared according to these known processes, the pigment and polymer are in the merely mixed state, such undesired phenomena as heterogeneous dispersion of the pigment and non-uniformity of the particle size cannot be avoided.
20 Accordingly, when these compositions are used as paints, such un-desired defec~s as uneven color concentration and for~ation of pigment specks are brought about.
It is the object of this invention to provide a paint composition which overcomes the above defects and provides homo-geneous pigment particles in a uniformty dispersed state.
In accordance with this invention, the above object is achieved by contacting a finely divided pigment other than elemental carbon-containing material with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bi-30 sulfite ions (also called acid sulfite ions) in the absence of r additional polymerization initiators. The pigment particles themselves in combination with the bisulfite ions act as a
2 ~
- ~ r ~5~3~5 polymerization initiator, and, the polymerization will proceed at room or slightly elevated temperatures. If desired, a polymer can be incorporated into the aqueous or alcoholic medium prior to the polymerization of the vinyl monomer, e.g. polyvinyl alcohol.
~ By the term "radical~polymerizable vinyl monomer" used in the instant specification and claims is meant a compound that can be vinyl-polymerized in the presence of a radical polymerization initiator to form a polymer.
The polymer-coated pigment obtained according to this t invention can be clearly distinguished from polymer-pigment compositions prepared by conventional processes due to the fact that the polymer is tightly bonded to the pigment surface and hence, the polymer-coated pigment can provide a very stable .
coating film. Further, in case a polymer is incorporated into the polymerization medium in advance, the resulting polymer-coated pigment is well fused with the polymer to form a homogeneous composition.
As the pigment, a regular commercial grade is normally ' used and it is preferable to use inorganic pigments such as chrome yellow, zinc yellow, barium yellow, white lead, prussian blue, barium sulfate, lead sulfate, zinc flower, titanium white, red iron oxide, chromium oxide and ultramarine. Metal-containing organic pigments can also be employed.
Any of monomers that can be vinyl-polymerized in the presence of a radical polymerization initiator can be used as the vinyl monomer in this invention. As the vinyl monomer there can be mentioned, for example, unsaturated carboxylic acids such as acrylic acid and methacrylic acid, salts and ;
esters of these unsaturated carboxylic acids, unsaturated nitriles such as acrylonitrile and methacrylonitriles, halogenated olefins .
~ 3 ~
~6)5~3~5 such as vinyl chloride and vinylidene chloride, aliphatic vinyl estess such as vinyl acetate and vinyl propionate, snd aromatic vinyl compounds such as styrene and divinyl benzene. These monomers are usually employed in amounts of 2 to 200 parts by weight per 100 parts by weight of the pigment, but these amounts can be increased depending on the intended use of the resulting composition.
As the reaction medium, water, alcohols such as methanol ar mixtures thereof can be used in the present invention. The presence of acid sulfite ions (HS03 ~ in the reaction medium is indispensable in this invention. This can be provided by addltion of sulfur dioxide, an aqueous solution of sulfurous acid, an acid sulfite such as ammonium acid sulfite or a combin-ation of a su~fite and a mineral acid. The amount of acid sulfite ions is chosen within a range of 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight, as calculated as sulfur dioxide per 100 parts by weight of the mono~er.
The paint composition obtained according to this invention can be used in the as-prepared emulsion state or various additives can be incorporated in the composition according to need. More-over, it is possible to separate only solid particles from the product and utilize same for powder painting, electros~atic painting and baking painting.
A coating film formed from the paint composition of this invention is excellent in strength and fixing properties and has excellent quality without uneven color concentration or pig-ment specks.
~ This invention will now be illustrated in more detail by reference to the following ~xamples.
5~3~5 Example 1 A 300-ml volume, three-neck flask equipped with a - -stirrer was charged with 20 g of titanium white, 100 g of a 5 % aqueous solution of polyvinyl alcohol and 50 g of methyl ` `~
acrylate and 0.5 g of a non-ionic surfactant was added to the mixture under agitation. Then 5 ml of a 1.0 N aqueous solution of sulfurous acid was added to the mixture and emulsion polymeri--æation was carried out at 60G.for 8 hours.
The so-obtained emulsion was coated as a paint on an aluminum plate to form a coating film having a film strength of 2.5 Kg/mm . The resulting film had good adhesion to the metal and good water resistance.
When the above procedures were repeated by employing potassium persulfate and hydrogen peroxide instead of the aqueous ~ ' solution of sulfurous acid, the resulting emulsion gave a film having a strength of 2.0 Kg/mm .
When the above emulsion obtained with use of the aqueous solution of sulfurous acid was filtered and the recovered solid was extracted with benzene for 24 hours, the polymer on the sur-face of the titanium white was not extracted whatsoever.
The so-recovered solid was incorporated into an acrylic ,~;
lacquer of the cellulose acetate butyrate type and the resulting composition was coated on a metal surface by spray coating.ACating film containing tightly bonded pigment particles could be obtained.
Example2 An autoclave equipped with a stirrer was charged with 5.0 Kg of red iron oxide powder, 2.5 l~g of vinyl chloride, 20 liters of water and 2 Kg of a 1~ aqueous solution of sulfurous acid and these were reacted at 50C. for 8 hours. The resulting reaction mixture was withdrawn from the autoclave and the unreacted monomer was removed by washing. The resulting slurry was filtered ;
i ~l~35~5 and the residue was washed wlth water and vacuum-dried at 100 C.
to obtain 6.72 Kg of a solid having a polymer content of 25.6 %.
The so-obtained solid was freeze-pulverized to a size of about 100 mesh and the pulverized solid was projected onto a vinyl butyral-treated slate plate by a Elame spray gun at a powder projection rate of 5 Kg/hr under a compressed air pressure of
- ~ r ~5~3~5 polymerization initiator, and, the polymerization will proceed at room or slightly elevated temperatures. If desired, a polymer can be incorporated into the aqueous or alcoholic medium prior to the polymerization of the vinyl monomer, e.g. polyvinyl alcohol.
~ By the term "radical~polymerizable vinyl monomer" used in the instant specification and claims is meant a compound that can be vinyl-polymerized in the presence of a radical polymerization initiator to form a polymer.
The polymer-coated pigment obtained according to this t invention can be clearly distinguished from polymer-pigment compositions prepared by conventional processes due to the fact that the polymer is tightly bonded to the pigment surface and hence, the polymer-coated pigment can provide a very stable .
coating film. Further, in case a polymer is incorporated into the polymerization medium in advance, the resulting polymer-coated pigment is well fused with the polymer to form a homogeneous composition.
As the pigment, a regular commercial grade is normally ' used and it is preferable to use inorganic pigments such as chrome yellow, zinc yellow, barium yellow, white lead, prussian blue, barium sulfate, lead sulfate, zinc flower, titanium white, red iron oxide, chromium oxide and ultramarine. Metal-containing organic pigments can also be employed.
Any of monomers that can be vinyl-polymerized in the presence of a radical polymerization initiator can be used as the vinyl monomer in this invention. As the vinyl monomer there can be mentioned, for example, unsaturated carboxylic acids such as acrylic acid and methacrylic acid, salts and ;
esters of these unsaturated carboxylic acids, unsaturated nitriles such as acrylonitrile and methacrylonitriles, halogenated olefins .
~ 3 ~
~6)5~3~5 such as vinyl chloride and vinylidene chloride, aliphatic vinyl estess such as vinyl acetate and vinyl propionate, snd aromatic vinyl compounds such as styrene and divinyl benzene. These monomers are usually employed in amounts of 2 to 200 parts by weight per 100 parts by weight of the pigment, but these amounts can be increased depending on the intended use of the resulting composition.
As the reaction medium, water, alcohols such as methanol ar mixtures thereof can be used in the present invention. The presence of acid sulfite ions (HS03 ~ in the reaction medium is indispensable in this invention. This can be provided by addltion of sulfur dioxide, an aqueous solution of sulfurous acid, an acid sulfite such as ammonium acid sulfite or a combin-ation of a su~fite and a mineral acid. The amount of acid sulfite ions is chosen within a range of 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight, as calculated as sulfur dioxide per 100 parts by weight of the mono~er.
The paint composition obtained according to this invention can be used in the as-prepared emulsion state or various additives can be incorporated in the composition according to need. More-over, it is possible to separate only solid particles from the product and utilize same for powder painting, electros~atic painting and baking painting.
A coating film formed from the paint composition of this invention is excellent in strength and fixing properties and has excellent quality without uneven color concentration or pig-ment specks.
~ This invention will now be illustrated in more detail by reference to the following ~xamples.
5~3~5 Example 1 A 300-ml volume, three-neck flask equipped with a - -stirrer was charged with 20 g of titanium white, 100 g of a 5 % aqueous solution of polyvinyl alcohol and 50 g of methyl ` `~
acrylate and 0.5 g of a non-ionic surfactant was added to the mixture under agitation. Then 5 ml of a 1.0 N aqueous solution of sulfurous acid was added to the mixture and emulsion polymeri--æation was carried out at 60G.for 8 hours.
The so-obtained emulsion was coated as a paint on an aluminum plate to form a coating film having a film strength of 2.5 Kg/mm . The resulting film had good adhesion to the metal and good water resistance.
When the above procedures were repeated by employing potassium persulfate and hydrogen peroxide instead of the aqueous ~ ' solution of sulfurous acid, the resulting emulsion gave a film having a strength of 2.0 Kg/mm .
When the above emulsion obtained with use of the aqueous solution of sulfurous acid was filtered and the recovered solid was extracted with benzene for 24 hours, the polymer on the sur-face of the titanium white was not extracted whatsoever.
The so-recovered solid was incorporated into an acrylic ,~;
lacquer of the cellulose acetate butyrate type and the resulting composition was coated on a metal surface by spray coating.ACating film containing tightly bonded pigment particles could be obtained.
Example2 An autoclave equipped with a stirrer was charged with 5.0 Kg of red iron oxide powder, 2.5 l~g of vinyl chloride, 20 liters of water and 2 Kg of a 1~ aqueous solution of sulfurous acid and these were reacted at 50C. for 8 hours. The resulting reaction mixture was withdrawn from the autoclave and the unreacted monomer was removed by washing. The resulting slurry was filtered ;
i ~l~35~5 and the residue was washed wlth water and vacuum-dried at 100 C.
to obtain 6.72 Kg of a solid having a polymer content of 25.6 %.
The so-obtained solid was freeze-pulverized to a size of about 100 mesh and the pulverized solid was projected onto a vinyl butyral-treated slate plate by a Elame spray gun at a powder projection rate of 5 Kg/hr under a compressed air pressure of
3 Kg/cm and a fuel gas pressure of 0.8 Kg/c~ . Then, the slate plate was post-treated at 200 C.for 10 minutes to obtain a water-resistant film in which the red iron oxide powder was uniformly 1~ dispersed.
- 6 - ~:
~ ''
- 6 - ~:
~ ''
Claims (11)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of paint emulsion compositions, which comprises contacting a finely divided pigment other than elemental carbon-containing material with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bisulfite ions in the absence of additional polymerization initiators, whereby the vinyl monomer is poly-merized and polymer-coated pigment particles are formed.
2. A process according to claim 1, wherein a polymer is incorporated into the reaction medium prior to polymerization of the monomer.
3. A process according to claim 2 wherein the polymer is polyvinyl alcohol.
4. A process according to claim 1, 2 or 3 wherein a sur-factant is incorporated into the reaction medium prior to polymer-ization of the monomer.
5. A process according to claim 1, 2 or 3 wherein about 2 to 200 parts by weight of monomer is used per 100 parts by weight of pigment.
6. A process according to claim 1, 2 or 3 wherein the monomer is selected unsaturated carboxylic acids and salts and esters thereof, unsaturated nitriles, halogenated olefins, aliphatic vinyl esters and aromatic vinyl compounds.
7. A process according to claim 1, 2 or 3, wherein the bisulfite ion is present in an amount of 0.01 to 100 parts by weight calculated as sulfur dioxide per 100 parts by weight of monomer.
8. A process according to claim 1, 2 or 3 wherein said pigment is selected from the group consisting of inorganic pigments comprising chrome yellow, zinc yellow, barium yellow, white lead, prussian blue, barium sulfate, lead sulfate, zinc flower, titanium white, red iron oxide, chromium oxide, ultra-marine, and metal-containing organic pigments.
9. A process according to claim 1, 2 or 3 wherein said medium is water, methanol or a mixture of water and methanol.
10. A process according to claim 1, 2 or 3 wherein said bisulfite ions are selected from the group consisting of sulfur dioxide, an aqueous solution of sulfurous acid, ammonium acid sulfite or a combination of a sulfite and a mineral acid.
11. A paint emulsion composition containing polymer-coated pigment particles in the dispersed state, said composition being obtained by mixing a finely divided pigment other than elemental carbon-containing material with a radical-polymerizable vinyl monomer in an aqueous or alcoholic medium containing bisulfite ions in the absence of additional polymerization initiators, and subjecting this mixture to emulsion polymerization.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1451873A JPS5345833B2 (en) | 1973-02-05 | 1973-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053395A true CA1053395A (en) | 1979-04-24 |
Family
ID=11863301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,688A Expired CA1053395A (en) | 1973-02-05 | 1974-02-04 | Process for the production of paint compositions |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5345833B2 (en) |
| CA (1) | CA1053395A (en) |
| DE (1) | DE2405249C3 (en) |
| FR (1) | FR2216335A1 (en) |
| IT (1) | IT1006243B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6031226B2 (en) * | 1973-09-26 | 1985-07-20 | 東ソー株式会社 | Method for producing acrylic powder coating composition for electrostatic coating |
| JPS5117929A (en) * | 1974-07-08 | 1976-02-13 | Sumitomo Bakelite Co | Anteiseio kairyoshita mukyukigurafutojugofukugotai |
| DE2559375A1 (en) * | 1975-12-31 | 1977-07-07 | Bayer Ag | PROCESS FOR THE MANUFACTURING OF PIGMENTS OF IMPROVED DISPERSIBILITY AND THEIR USE |
| US4330460A (en) * | 1980-04-14 | 1982-05-18 | Xerox Corporation | Process for preparing colored toner particles employing a halogen salt to inhibit the aqueous phase polymerization |
| JPS5875251A (en) * | 1981-10-28 | 1983-05-06 | Nec Corp | Malfunction detecting circuit |
| DE19633445C1 (en) * | 1996-08-20 | 1998-01-22 | Herberts Gmbh | Direct production of pigmented and/or filled optionally modified polycondensation resin batch |
| JP2000053713A (en) | 1998-03-17 | 2000-02-22 | Ciba Specialty Chem Holding Inc | Method for continuously producing polymer-based pigment compound |
| EP0943662B1 (en) * | 1998-03-17 | 2002-05-02 | Ciba SC Holding AG | Continuous process for preparing polymer based pigment preparations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE913825C (en) * | 1944-07-11 | 1954-06-21 | Hoechst Ag | Process for emulsion polymerization of unsaturated compounds |
| NL234595A (en) * | 1957-12-28 | |||
| US3054762A (en) * | 1958-12-29 | 1962-09-18 | Shawinigan Chem Ltd | Process for preparing emulsion paints by polymerizing monomer in presence of monomer |
-
1973
- 1973-02-05 JP JP1451873A patent/JPS5345833B2/ja not_active Expired
-
1974
- 1974-02-01 IT IT2012474A patent/IT1006243B/en active
- 1974-02-04 DE DE19742405249 patent/DE2405249C3/en not_active Expired
- 1974-02-04 CA CA191,688A patent/CA1053395A/en not_active Expired
- 1974-02-05 FR FR7403837A patent/FR2216335A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2216335A1 (en) | 1974-08-30 |
| JPS5345833B2 (en) | 1978-12-09 |
| DE2405249B2 (en) | 1978-08-17 |
| DE2405249A1 (en) | 1974-08-08 |
| DE2405249C3 (en) | 1982-04-08 |
| JPS49104926A (en) | 1974-10-04 |
| IT1006243B (en) | 1976-09-30 |
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