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WO2013012699A2 - Compositions de revêtement à base de polyuréthane - Google Patents

Compositions de revêtement à base de polyuréthane Download PDF

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Publication number
WO2013012699A2
WO2013012699A2 PCT/US2012/046600 US2012046600W WO2013012699A2 WO 2013012699 A2 WO2013012699 A2 WO 2013012699A2 US 2012046600 W US2012046600 W US 2012046600W WO 2013012699 A2 WO2013012699 A2 WO 2013012699A2
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
based coating
polyurethane based
present
amount
Prior art date
Application number
PCT/US2012/046600
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English (en)
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WO2013012699A3 (fr
Inventor
Vipulkumar H. PRAJAPATI
Original Assignee
3M Innovative Properties Company
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 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Publication of WO2013012699A2 publication Critical patent/WO2013012699A2/fr
Publication of WO2013012699A3 publication Critical patent/WO2013012699A3/fr

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Classifications

    • 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
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • 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
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38

Definitions

  • the present invention relates to novel polyurethane based coatings, particularly for selectively imparting excellent water vapour impermeability and in-can settling stability, in addition to low viscosity, for application in industrial coating.
  • the composition of the present invention is used particularly for protection of concrete and metal surfaces.
  • PU coatings are widely known for their versatility of application with many advantages over the conventional coating systems.
  • PU coatings can be divided into one pack and two pack systems, wherein the one pack system contains a dissolved fully reacted PU or blocked isocyanate, while the two pack system can contain various types of polyols, varying in functionality, chain length and backbone in one pack and isocyanate in the other pack. Both these systems can be further classified as solvent based, water based or solvent free systems. The solvent free
  • a frequently encountered problem with coating composition is that of the settling of paints over some period of storage thereby resulting in some of the pigments remaining at the bottom of the can/drum. Improper mixing affects the stoichiometry of the finished product and results in inconsistent & inferior performance on application. In case of sticky heavy settling, desired bits free consistency is not achieved even after considerable mixing during application, resulting in inferior performance.
  • a number of publications are known that deal with solvent free polyurethane compositions for application as a protective coating.
  • US 2007-185241 describes cured resin matrix with a plurality of bubbles which provide improved insulative properties and improved adhesion to overlying paint coatings which in turn offers protection against corrosion and acts as heat insulator.
  • US 2008-229976 discloses polyurea compositions and polyurethane compositions related to stain and fouling resistant coatings that provide durable, light weight coatings which exhibit oil- repellency, water-repellency, and stain resistance.
  • US 6977279 relates to solventless reactive system which cure at room temperature based on blocked polyisocyanates, primer amines, compounds with oxirane groups and 2,3 dimethyl-3,4,5,6- tetrahydropyridimine .
  • the objective of the present invention is to provide a cost effective coating which exhibits superior properties in terms of corrosion resistance, moisture impermeability, in-can settling stability and having low viscosity.
  • one embodiment of the present invention is to provide a polyurethane based coating composition having a base component and an activator as another component wherein the base component comprises polyols and ingredients such as catalyst, defoamer, molecular sieve and fillers; while the activator consists essentially of polyisocyanate.
  • the base component of the composition may comprise other ingredients such as pigments, additional polyols, amines and chain extenders.
  • the components of the coating composition interact synergistically to confer a unique combination of the physical and chemical properties to the resultant composition which make it superior to the state of the art compositions.
  • the instant coating composition comprises the individual components in the following concentration:
  • the base and an activator is in 3: 1 (v/v) proportion.
  • the polyol could be a diol, a triol, a higher polyol, or a mixture of one or more of the said polyols.
  • Some other additives such as pigments, chain extenders etc also may be used to control and modify the reaction process and performance characteristics of the polymer.
  • This invention also relates to a process for preparing the polyurethane based coating composition wherein the process comprises initially of preparing the base component and mixing the base with the activator in a suitable proportion to provide the coating composition for use in corrosion protection of metal and concrete structures.
  • This invention also relates to articles and surfaces coated with the instant coating composition.
  • Figure 1 shows a graph plotting the water vapour permeability of the standard coating composition of the invention.
  • Figure 2 shows a graph plotting the water vapour permeability of a coating composition without mica.
  • polyol may include two or more such polyols.
  • all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention pertains.
  • the coating composition of the present invention is a solvent free urethane based
  • composition comprising a base and an activator, wherein the base comprises a number of additives like polyols, defoamer, molecular sieve, filler, catalyst and other optional additives; while the activator consists essentially of polyisocyanate.
  • the polyols form an essential ingredient of the base component of the present invention.
  • a polyol is an ploymeric alcohol containing multiple hydroxyl groups.
  • polyols are defined as compounds with multiple hydroxyl functional groups available for organic reactions.
  • a molecule with two hydroxyl groups is a diol, one with three is a triol, one with four is a tetrol and so on.
  • Monomeric polyols such as glycerin, pentaerythritol, ethylene glycol and sucrose often serve as the starting point for polymeric polyols. These materials are often referred to as the "initiators" and reacted with propylene oxide or ethylene oxide to produce polymeric polyols.
  • Polymeric polyols could be polyether polyols, polyester polyols or OH terminated polyacrylics or combination of them.
  • the characteristics of polyols depends on are their molecular backbone, initiator, molecular weight, percentage primary hydroxyl groups, functionality, viscosity and so on.
  • Many polyols are polydispersive materials, being blends of two or more polyols each of specific molecular weights, to give intermediate molecular weight materials.
  • Natural oil polyols or saturated aliphatic polyester polyols with low viscosities at room temperatures are used in the production of polyurethanes.
  • Natural oil polyols also known as NOPs or biopolyols, are polyols derived from vegetable oils by several different techniques. The primary use for these materials is in the production of polyurethanes.
  • the most promising natural oils for the industrial development of biobased polyols are soybean oil, castor oil, palm oil, and canola oil.
  • Castor oil which is obtained from castor seed, is a triglyceride of fatty acid wherein 90% of the fatty acid chains are ricinoleic acid, has presence of OH functional group on 12 th carbon atom, which makes it polar and reactable, which is not the case with other seed oils.
  • castor polyols derived from castor oil possess long C chains with a functional unbranched "OH" group which provides flexibility on reaction with isocyanate to form the polyurethane bond.
  • the castor oil of BSS Grade or commercial grade castor oil More particularly, the castor polyol is Jagropol 115.
  • tri-functional oil-derived polyol having hydroxyl number ranges from 320 to 350 mg KOH/g containing both primary and secondary hydroxyl groups, which are completely miscible with a wide variety of natural oil polyols, demonstrate ability to rapidly build polyurethane cross-linked networks.
  • the trifunctional polyol is polypropylene ether polyol (Desmophen 1380BT).
  • Di primary diols also can be used as an ingredient of the base composition of the present invention.
  • Diols - alcohols that contain two reactable hydroxyl groups can be classified as linear/branched or aliphatic/aromatic diols.
  • 2-methyl 1,3 dipropane diol due to its unique branched structure (i.e) asymmetrical nature, conferred upon it due the presence of the odd number of carbon atoms between the two hydroxyl groups thus inhibiting close packaging thereby exhibiting greater transparency, weatherability, longer shelf life, aiding in suspension of heavy fillers/solids, decreased viscosity, resist settling over the resin when stored for long periods of the end use applications.
  • the 2-methyl 1,3 dipropane diol is MPDiol.
  • 1,4 butane diol is also a preferred diol.
  • Fillers in this invention serve multiple functions based on the type of filler used. Fillers may thicken the composition, support its structure, prevent sagging, increase volume and also enhance the technical properties of the composition.
  • Mica acts as filler providing a smooth consistency, improving the workability of the compound, and providing resistance to cracking. Mica's value is based on its unique lamellar shape, which forms compact packing in the dried film and hence reduces film impermeability.
  • mica functions as a pigment extender that facilitates suspension, reduces chalking, prevents shrinking and shearing of the paint film, increases resistance of the paint film to water penetration and weathering, and brightens the tone of colored pigments.
  • mica coated with titanium dioxide (TiC ⁇ ) results in a pigment that produces a reflective color depending on the thickness of the coating.
  • Ti0 2 acts as a white pigment providing opacity to the dried film.
  • Ti0 2 Anatyze or Rutile In addition to Ti0 2, carbon black such as 318M Black serves as a black pigment which in combination with the white pigment provides a grey colour to the composition.
  • Various pigments can be added for different color of the final composition.
  • fillers such as barium sulphate not only might serve as a white pigment but also modify the consistency and help in providing impact resistance to the application. Of preference is Barytes 2080.
  • One other filler used in these polyurethane compositions is Silica. Silica not only leads to cost reductions by increasing the bulk of the composition but also prevents sagging of the resin.
  • Catalysts are used to catalyse the polymerization of the polyol with the polyisocyanate.
  • Amine compounds and organo metallic complexes are used as catalysts.
  • amines such as tertiary amines, difunctional primary amines etc are used.
  • aromatic diamine such as diethyl toluenediamine which is commercially available under the name Ethacure 100.
  • the catalyst could be used in an amount of 0 to 5% depending on the mode of application by spray or brush.
  • the composition is devoid of catalyst.
  • the said composition without catalyst is suitable for application by brush also by increasing the usable life.
  • Defoamers are used to modify the characteristics of polyurethane composition by eliminating process defects like entrapped bubbles and surface defects such as pin holes and orange peelmarks, acting as air release and anti-foaming agents.
  • silicone free defoamers such as BYK 054 or BYK 535 or BYK 1794 or Foamex N.
  • Molecular sieves or moisture scavengers which contain tiny pores of a precise and uniform size are used as an adsorbent for gases and liquids.
  • highly effective moisture scavenger for coating systems that adsorbs practically only water.
  • isocyanate which is highly reactive to water.
  • micronized, highly porous, crystalline aluminosilicate with pore openings of approximately 3 A such as SYLOSIV A3 or Purmol 3ST or A4 with 4 A pore openings.
  • Paste forms of the molecular sieves P3 and P4 can also be used.
  • Chain extenders are low molecular weight hydroxyl and amine terminated compounds that play an important role in the polymer morphology of polyurethane chains.
  • the chain extender is an amine. More preferably the amine is polyetheramines such as Jeffamine D 400.
  • Pigments which could be used in the invention comprises synthetic iron oxides.
  • Preferred examples of pigments are Bayferrox Black 318M along with Titanium dioxide to create Gray color of the composition.
  • the base of the polyurethane based coating composition comprises 35 to 75 % of polyol mix which includes 0.5 to 5 % of trifunctional polyol and 1-10% of 2-methyl 1,3 dipropane diol, 3 to 25% of mica, 0.5 to 1.5 % of defoamer, 2 to 10 % of molecular sieve, and 0 to 5% of catalyst.
  • composition may optionally contain 0 to 5% of chain extender, 5 to 40% of barium sulphate, 5 to 40% of silica, 2 tol0% of titanium dioxide and 0.15 to 5% of color pigments.
  • Another major embodiment of the present invention is related to a process for preparing the polyurethane based coating composition wherein the process comprises of initially preparing the base component.
  • the base component is nothing but mixture of OH functional polyol components with molecular sieve, fillers, pigments, catalysts and additives.
  • the base component is prepared by dispersing the solid materials viz., pigments, fillers & other additives in polyols in high speed disperser (HSD) or twin shaft disperser and stabilizing the same with rest of the resin and additives.
  • HSD high speed disperser
  • the solid matters can be ground to finer to medium grind depending on the application requirement.
  • the base component is mixed with the activator in a suitable proportion to provide the coating composition for use in corrosion protection of metal and concrete structures.
  • the solvent free urethane coating of the invention is applied by plural feed spray equipment.
  • Most of the known solvent-free urethane compositions are high in viscosity and hence the base component is always heated in the range of 40 to 55°C to reduce the viscosity (viscosity reduces with increase in material temperature) to facilitate the ease of application. Since the viscosity of the instant composition is low, it can be easily applied without heating the base part at temperature above 30°C.
  • the same product can be made applicable by brush also by increasing the usable life. This needs removal of the catalyst from the composition.
  • the standard urethane coating composition of the invention has the following composition.
  • the composition comprises A) Base component and B) Activator.
  • Base component has the composition as shown in Table 1
  • the base component was prepared by dispersing the solid materials viz., pigments, fillers and other additives in polyols in high speed disperser (HSD) or twin shaft disperser and stabilizing the same with rest of the resin and additives.
  • HSD high speed disperser
  • the polyols, especially polyester polyol and some portion of castor oil were taken in the vessel followed by addition of defoamer under stirring.
  • the mix was stirred at slow speed and subsequently the fillers like barium sulfate, silica, mica, molecular sieve, titanium dioxide and pigments were added in sequence under stirring.
  • the speed of the HSD blade was adjusted such a way to ensure proper vortex formation.
  • the solids were dispersed at a tip speed of about 3 to 8 meter per seconds till the finish was achieved.
  • the composition was stabilized with remaining resin, polyols, amines and additives. Defoamer is used to take care of process generated air-entrapments. During processing, the composition was maintained below 60°C by circulating cooling water through the jacket of vessel. The composition was then filtered through filter and packed.
  • the second part of the composition viz., the activator, was prepared by packing the solvent free polyisocyanate under nitrogen blanketing environment.
  • the polyurethane based coating composition was obtained by mixing 3 parts of the base with 1 part of the activator, by volume.
  • Example 1 The product as obtained by Example 1 was subjected to tests for various performance parameters such as specific gravity, flowability, tensile strength, elongation, flexibility, abrasion resistance etc., at the Corrosion Science and Engineering Laboratory of Indian Institute of
  • Tables 2 and 3 show the details and results of the tests for various performance parameters respectively.
  • the polyurethane based coating composition of the present invention exhibited excellent performance parameters that it can be very effectively applied to concrete and metal surfaces.
  • An ambient condition stability test for the urethane coating composition of the present invention was performed in order to ensure that the product is stable under recommended storage conditions.
  • Accelerated stability study was conducted to predict the long-term stability in short period. In this field, 8 week accelerated stability translates in to over 1 year stability in actual storage conditions.
  • the material was packed in 200 ml or 500 ml cans, sealed and was kept at elevated temperature of 60°C for weeks. Four packs were kept for taking observations at the interval of 1 week, 2 week, 4 week and 8 weeks. The observations were taken for degree of settling or phase separation. The material was also tested for performance parameters. The experiment the details are shown in Table 6 and the observations are shown in Table 7. Ratings are as explained in Table 5. Table 6
  • the instant composition was tested to determine the resistance of the coating towards various chemicals in case of chemical splash, spillage of complete immersion.
  • Standard panels were coated with the coating composition, edge sealed and were dipped in the chemicals at 23°C and 50% humidity conditions.
  • the coating film was observed at regular intervals for any defects like blistering, delamination, cracking or peeling.
  • the coating was also tested for adhesion and hardness.
  • the instant coating composition was observed to have excellent chemical resistance against chemicals such as ammonium hydroxide 25% (v/v), citric acid 5% (v/v), methanol, sodium
  • the instant composition was tested for permeability towards water vapors following standard ASTM E96.
  • the testing was done with Water method. Distilled water was filled in standard payne permeability cup and the cured film of the coating, which was of same dimension as the cup, was put on the cup opening. The edges were sealed with suitable sealant. The assembly was then kept under controlled temperature and humidity conditions. The temperature was maintained at 23 +/- 1°C and the relative humidity was maintained at 50 +/- 2 %.
  • Rate of Permeation 0.0003 gms/24Hr
  • Table 9 shows the details of the test with a composition without mica and Figure 2 shows its graphical representation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition de revêtement à base de polyuréthane qui présente des propriétés supérieures en termes de stabilité, de résistance à la corrosion et de perméabilité à l'humidité, ladite composition de revêtement présentant une faible viscosité. La composition de revêtement à base de polyuréthane comprend une base et un activateur, le composant de base comprenant un polyol, une charge, un démoussant, un catalyseur et un tamis moléculaire et l'activateur comprenant un polyisocyanate. De préférence, le polyol comprend un polyol d'huile de ricin, du 2-méthyl-1,3-dipropanediol ou du 1,4-butanediol et la charge comprend du mica. Le mica, en plus d'être une charge, fonctionne également comme un diluant de pigment. Dans certains modes de réalisation, ladite composition est dépourvue de catalyseur. Ladite composition de revêtement est utile dans le revêtement de surfaces de béton et de métal.
PCT/US2012/046600 2011-07-15 2012-07-13 Compositions de revêtement à base de polyuréthane WO2013012699A2 (fr)

Applications Claiming Priority (2)

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IN2429CH2011 2011-07-15
IN2429/CHE/2011 2011-07-15

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WO2013012699A3 WO2013012699A3 (fr) 2013-04-11

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EP3218597B1 (fr) 2014-11-10 2019-03-27 Polytech A/S Matériau polyuréthane, son procédé de préparation et couche de protection pour pale d'éolienne
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WO2020190899A1 (fr) 2019-03-21 2020-09-24 DDP Specialty Electronic Materials US, Inc. Composition de revêtement résistant à l'eau
US20210009874A1 (en) * 2017-12-27 2021-01-14 Dow Global Technologies Llc Two-component solventless adhesive compositions for adhesion to metal and/or metallized substrates
CN112574661A (zh) * 2020-12-31 2021-03-30 郑州双塔涂料有限公司 一种双组份丙烯酸聚氨酯中涂漆及其制备方法
CN113773743A (zh) * 2021-09-29 2021-12-10 惠州市惠阳区嘉泰涂料有限公司 耐高温、耐老化型低voc聚氨酯防腐涂料及其制备方法
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