WO1995009209A1 - Compositions de revetement aqueuses reticulables - Google Patents

Compositions de revetement aqueuses reticulables Download PDF

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Publication number
WO1995009209A1
WO1995009209A1 PCT/AU1994/000599 AU9400599W WO9509209A1 WO 1995009209 A1 WO1995009209 A1 WO 1995009209A1 AU 9400599 W AU9400599 W AU 9400599W WO 9509209 A1 WO9509209 A1 WO 9509209A1
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WO
WIPO (PCT)
Prior art keywords
coating composition
acetoacetate
dispersion
paint
groups
Prior art date
Application number
PCT/AU1994/000599
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English (en)
Inventor
Algirdas Kazimieras Serelis
Craig David Meekings
Original Assignee
Ici Australia Operations Proprietary Limited
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 Ici Australia Operations Proprietary Limited filed Critical Ici Australia Operations Proprietary Limited
Priority to AU78048/94A priority Critical patent/AU678297B2/en
Publication of WO1995009209A1 publication Critical patent/WO1995009209A1/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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/062—Copolymers with monomers not covered by C09D133/06
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides

Definitions

  • This invention relates to crosslinkable binders for water-borne coatings and in particular to binders where crosslinking is provided by acetoacetate and amine functional groups.
  • Polymeric coatings for use on a variety of substrates for protective and decorative purposes are well known. When in liquid form prior to application they usually have volatile organic solvents or water as the liquid carrier phase which evaporates after application to leave a solid film of a coating on the substrate. It is also well known to improve the coating performance, for example, its hardness and solvent resistance by causing them to become crosslinked or cured after application to the substrate. These harder more solvent resistant properties are advantageous when abrasive or organic solvent containing household cleaners are used. To achieve crosslinking or curing it is known to employ crosslinkable coating compositions whereby the composition includes components which react to cause crosslinking after application.
  • Such reaction may be augmented or catalysed by the presence of atmospheric oxygen as in the case of alkyd coatings and these are widely used for decorative paints, particularly for trim paints where hard tough films are desirable.
  • these coatings usually have organic solvent as the carrier phase.
  • the crosslinkable binder may have reactive and co-reactive groups which covalently co- react to form a crosslinked coating.
  • Crosslinking reactions are of course not intended to take place to an unacceptable degree until after the composition is applied to the substrate.
  • crosslinkable paints that rely upon external agents such as atmospheric oxygen or moisture to trigger or catalyse the crosslinking reaction
  • can-stable one-pack products can be prepared.
  • the binders contain complementary reactive groups the pot life of these products is so short that the products can only be effectively used as a two-pack product where the complementary reactive groups are kept apart in separate packs until the packs are combined shortly before application to the substrate.
  • this is inconvenient and it is desirable to have one-pack products.
  • a potentially useful and known class of coating compositions comprises an acetoacetate functional polymer, e.g. an acrylic polymer or a polyester, and a polyamine.
  • acetoacetate functional polymer e.g. an acrylic polymer or a polyester
  • polyamine e.g. an acrylic polymer or a polyester
  • Such compositions are described, for example, in Journal of Coating Technology, Vol. 61 (771) pages 31-37, 1989, which involves crosslinkable polymers in organic solvents. In this article it is postulated that crosslinking occurs by means of enamine formation between the enolic acetoacetate groups and the amine groups.
  • compositions with acetoacetate and amine complementary reactive groups are restricted to two-pack compositions in organic solvents.
  • Aqueous or water-borne coatings are preferred from safety and environmental perspectives compared to coating compositions containing volatile organic solvents. Accordingly, water-borne coatings have been widely used for many years especially as decorative paints.
  • One common binder for this market area comprises a film-forming aqueous dispersion of thermoplastic polymer particles which after application and evaporation of water coalesce and form a continuous film. There is usually a compromise between the ability to coalesce and form a film and the ultimate hardness of the film. Soft particles or particles with a low glass transition temperature (Tg) coalesce well but compromise properties such as block resistance and mar resistance. This compromise may be improved by the use of minor amounts of volatile coalescents or plasticisers.
  • Tg glass transition temperature
  • compositions hence suffer from the disadvantages described previously of using volatile blocking groups.
  • the considerable efforts to obtain one-pack crosslinkable coating system are exemplified by the work described in this paper.
  • the authors report the unacceptability of non-blocked polyamines for one-pack can stability and also the unsuitability of aliphatic ketimines in water based coatings because of their moisture sensitivity.
  • US Patent 5,270,380 of Adamson et al discloses aqueous compositions where the dispersion polymer contains acetoacetate groups which are pre-reacted with complementary reactive groups attached to a modifying compound.
  • the object of this invention is to increase the open time of aqueous coating compositions. To achieve this objective it is important that the reaction occurs before the composition is applied and which is clearly not intended to further react after film formation.
  • This invention provides in one form a crosslinkable coating composition
  • a crosslinkable coating composition comprising an aqueous film-forming dispersion of addition polymer comprising acetoacetate functional groups and an essentially non volatile polyamine having at least two primary amine groups and wherein the mole ratio of acetoacetate to primary amine groups is between 1:4 and 40:1.
  • the acetoacetate groups are provided by copolymerising addition polymerisable monomers containing acetoacetate functional groups.
  • the acetoacetate groups are incorporated by polymerisation of a monomer selected from the group consisting of allyl acetoacetate, acetoacetoxyethyl methacrylate, acetoacetoxypropyl methacrylate and acetoacetoxybutyl methacrylate and the corresponding acrylates.
  • acetoacetate groups are incorporated by polymerisation of acetoacetoxyethyl methacrylate (AAEM) .
  • AAEM acetoacetoxyethyl methacrylate
  • the polyamine is a polyoxyalkylene polyamine.
  • the polyoxyalkylene polyamine has the alkylene selected from ethylene and propylene or mixtures thereof.
  • the aqueous dispersion is sterically stabilised and more preferably it has polyoxyalkylene chains, and most preferably polyoxyethylene chains that confer steric stability.
  • the mole ratio of acetoacetate to primary amine groups is between 1:1.5 and 15:1, more preferably between 2:1 and 8:1 and most preferably about 4:1.
  • the coating composition comprises a blend of soft and hard polymer particles.
  • the aqueous film forming dispersions of this invention are usually copolymers of the acetoacetate functional monomers and other addition polymerisable comonomers.
  • useful comonomers include alkyl acrylates and methacrylates where the alkyl group has 1 to 20 (and more preferably 1 to 8) carbon atoms, styrene, vinyl acetate, butadiene, acrylonitrile and simple or substituted olefins.
  • Monomers containing other functional groups such as hydroxyl or carboxyl groups may be used. However, we have found best results are achieved when carboxylic acid groups are kept to a minimum or absent as the presence of carboxyl groups tends to have an adverse effect on can stability.
  • the acid value of the disperse polymer should be less than lOmg KOH/g, more preferably less than 4mg KOH/g and most preferably less than 2mg KOH/g.
  • Minor amounts of functional monomers directed towards specific objectives such as adhesion promotion may also be incorporated.
  • the selection of comonomers and their relative proportions is based on well established principles in the art and generally balance properties such as exterior durability, toughness and hardness with cost.
  • the molecular weight of the copolymers is generally similar to known latexes and typically would be at least 40,000 (Mn) .
  • a light gelling structure in the particles is permitted in a similar fashion to the gel structure achieved by including minor amounts of polyfunctional acrylate or methacrylate monomers, provided that film formation is not unacceptably compromised.
  • the minimum film forming temperature (MFT) of the aqueous dispersion is usually in the range of 0 - 30°C which is similar to commercially available dispersions of aqueous film formers.
  • MFT's le addition polymerisable monomers are selected so that the Tg of the copolymer is approximately similar to the desired MFT.
  • particularly beneficial coatings may be achieved by combining at least two dispersions having different Tg's.
  • improved early film properties such as hardness are achieved when the combination of film forming dispersions of 44% of Tg -30°C and 56% of Tg +50°C is used.
  • acceptable results can be achieved by incorporating the acetoacetate functional groups into only one of the dispersions, the acetoacetate groups are preferred to be present in both dispersions for best results.
  • the composition may comprise a soft and hard dispersion where the hard dispersion does not of itself form a continuous film at the temperature of use but the blend of soft and hard does form such a film, optimally aided by a minor amount of volatile coalescent.
  • aqueous dispersions of the present invention may be prepared by known means such as emulsion polymerisation. However best results are achieved where the aqueous dispersion is prepared such that it is sterically stabilised.
  • sterically stabilised is an art recognised term in colloid science and means that in aqueous systems colloidal stability is conferred by the presence of a sheath of water soluble polymeric and uncharged oligomeric chains anchored to the particle surface.
  • sterically stabilised dispersions we mean that whilst other types of stability, such as anionic or cationic, may be present there is stability conferred by steric stabilisation.
  • steric stability is conferred using polyethylene oxide chains.
  • a convenient test to ascertain whether the dispersion is sterically stabilised or not is to increase the ionic concentration of the aqueous phase to such an extent that ionic stabilisation is nullified and then to assess the stability of the dispersion. If it remains stable under these conditions we regard it as sterically stabilised. It is believed that in this invention the use of sterically stabilised particles confers enhanced can stability and reduces premature crosslinking. It is believed that, in our preferred compositions, steric stabilisation of the particles by polyoxyalkylene chains contributes to good can stability when the polyamines are polyoxyalkylene polyamines.
  • compositions of the present invention are particularly suitable for gloss and semi-gloss paints.
  • these types of paints we have found it to be advantageous to achieve the desired gloss to use small particle size polymer dispersions, especially for the high Tg polymer dispersion where the binder consists of a mixture of low and high Tg dispersions.
  • the particle size should preferably be less than 200 nm in diameter, more preferably less than 150 nm and most preferably less than 100 nm.
  • Preferred paints have a gloss of at least 10 (60 head) and more preferably 40 (60 head).
  • polymer dispersions which have a core shell structure whereby the polymer composition at the outer shell of the particle differs from those towards the centre of the particle.
  • AAEM acetoacetate functionality
  • levels from 2-30% by weight of the disperse polymer confer useful properties.
  • levels of 4-20% and 5-12% give best results.
  • This monomer is relatively expensive and hence in practice its level is minimised consistent with achieving the extent and rate of crosslinking desired together with desired can stability.
  • stab lity equates to typical periods of time and temperature c editions that a product may be on the shelf before it is applied.
  • Accelerated testing at elevated temperatures, such as 50°C, over shorter periods of time provides a good basis to predict storage behaviour at ambient temperatures. In practice, if after storage at 50°C for 1 week the coating performs adequately. This is an accurate prediction of sufficient storage stability behaviour for practical applications.
  • the polyamine component is essentially non-volatile and has at least two primary amine groups.
  • essentially non-volatile we mean in normal use the polyamine component does not become introduced into the atmosphere. Generally this means the polyamine component has a vapour pressure less than 0.1 mm Hg at 25°C. This is the definition sometimes used by the paint industry to define compounds necessary for zero VOC compositions.
  • the reactivity of the polyamine is a factor that influences its volatility in practice enabling nominally volatile polyamines to be used provided they react before they significantly volatilise.
  • the polyamine contains polyoxyalkylene chains, especially ethylene and propylene.
  • the polyamine is water soluble and by this we mean it has a water solubility of at least lOOg/litre though preferably it should be fully miscible with water. This is surprising in the light of the Kim and Williams paper previously discussed where they found in their aqueous dispersion system that increased hydrophilicity led to poorer can stability.
  • polyamine is an ethoxylated polyamine of molecular weight 600 as supplied by Texaco under the trade name Jeffamine ED600.
  • suitable polyamines are - Jeffamine ED900, D400 and EDR148.
  • the mole ratio of acetoacetate functional groups in the disperse phase to primary amine groups is approximately 4:1, and this in practice means the weight ratio between the dispersion (NV) and polyamine (NV) is approximately 100:4.
  • NV dispersion
  • NV polyamine
  • 4:1 is the preferred ratio quite a wide range of ratios give acceptable coatings.
  • the best ratios depend on the polyamine used as well as the aqueous polymeric dispersion, but the best ratios can be readily ascertained by a series of ladder experiments that varies the ratios systematically.
  • Crosslinking of the films formed by the compositions of our invention is an essential feature. In practice crosslinking can be conveniently measured by solvent resistance, such as xylene "double rubs" as known in the art.
  • the binders of the present invention may be combined with pigments and other conventional paint additives to produce corresponding paints with desirable properties.
  • volatile plasticisers are not necessary and therefore the paint may be formulated to cc ply with the zero VOC requirement.
  • minor amounts of co-solvents that function as wet edge solvents volatile plasticisers and modifiers may be used and coating compositions that include these additives or modifiers are still regarded as aqueous coating compositions. Typically these additional volatile organic substances would not exceed 10% by weight of ti total compositions as applied. Whilst significant levels of volatile organic compounds are to be avoided the coating compositions of this invention are aqueous coatings provided water is the major portion of the volatile phase.
  • Stage A was charged to a reaction vessel equipped with stirrer, condenser, nitrogen blanket and feed facilities.
  • a stage was loaded to a dispersion vessel and premixed B stage slowly added with a gradual increase in stirrer speed. High speed dispersion was effected after 15 minutes. The stirrer speed was reduced and C stage was added slowly. D stage ingredients were consecutively added with continuous steady stirring which continued for a further 20 minutes. This paint was designated paint IB.
  • Paint, pigmented or unpigmented was tested by casting a film using a 175 micron doctor blade. Films were cast onto polypropylene panels. These films were then allowed to dry for 1 week at 25°C before being tested. Meanwhile a sample of the (fresh) paint was placed in a sealed vessel and aged in an oven at 50°C for 1 week.
  • the dry films were tested by rubbing with a soft cloth soaked in xylene. Rubs were performed by hand using a steady and even force. "Double rubs" (i.e. one forward and backward motion) were counted until a complete segment of the film had been removed. This figure was then recorded. All testing was performed using duplicate films and the mean figure quoted.
  • the difference between the double rub score of the first panel and that from the aged paint indicates the degree to which the paint retains its crosslinking potential. i.e. can stability.
  • a paint was prepared in a similar manner to that of Example 1 except that dispersion 1A was replaced with an identical dispersion save for the absence of the AAEM monomer (Dispersion 2).
  • the particle size was 85 nm and solids 51%. Slight adjustment to the monomer ratios was necessary to provide the same Tg of 9°C as in dispersion 1A.
  • the paint formulation was as follows.
  • This example showed no crosslinking, even when the fresh paint was tested.
  • This example illustrates the use of an acetoacetate monomer other than AAEM.
  • the preparative process of dispersion 1A was repeated except that the 10% AAEM was replaced with 6.6% of allyl acetoacetate monomer.
  • the particle size was 86 nm and solids were 49.6%.
  • This substitution provided an equal molar level of acetoacetate function groups to that in Example 1.
  • Minor adjustments to the methyl methacrylate and butyl acrylate monomers levels were necessary to provide the same theoretical Tg of 9°C as in dispersion 1A. Paint formulation from Example 2 was used.
  • This example illustrates a paint composition using a mixture of polymeric dispersions of differing Tg's.
  • This dispersion had a solids content of 51.5%, had a particle size of 107 nm, and was designated dispersion 4A.
  • This dispersion had a solids content of 51%, particle size 80 nm, and was designated dispersion 4B.
  • An unpigmented paint was prepared by blending 56 parts of dispersions 4A and 44 parts of dispersion 4B with the amine crosslinker from Example 1 to provide an acetoacetate to primary amine ratio of 4 to 1 which is the same ratio as from Example 1.
  • Example 5 This sample showed good crosslinking before and after storage. Furthermore, early film properties such as hardness were enhanced with this blend of dispersions when compared to the paint of Example 1.
  • Dispersion 1A 100 parts from Example 1 was combined with Jeffamine ED600 (1.64 parts) (Example 6) and Jeffamine ED600 (6.56 parts) (Example 7) by slow addition of the amine crosslinker to each of the dispersion samples under low speed stirring.
  • These unpigmented compositions were tested as in C from Example 1 to give the following results.
  • Example 9 which was a paint as in Example 1.
  • Example 6 was repeated with the amine crosslinkers and the results are set out below. The amounts of amine crosslinker were adjusted to maintain the 4:1 acetoacetate/primary amine ratio of Example 6.
  • This example illustrates the use of a polymeric dispersion prepared using anionic surfactants as well as non-ionic surfactants.
  • a polymeric dispersion of Tg -13°C was prepared as follows:
  • RK500 Polyoxyethylene hexyl 0.900 ether phosphate
  • a stage was loaded to a reaction vessel equipped with stirrer, nitrogen blanket and feed facilities. The charge was heated to 75°C. B stage was then added with stirring and the pH was adjusted (if necessary) to 9. C stage was added and at the completion of the exotherm D and E stages were both fed concurrently over four hours. F stage was added to E stage and dissolved in that part of E stage which had not been fed into the reaction vessel after 3 hours 24 minutes of the feeds. The temperature was maintained at 75°C throughout and for a further fifteen minutes at the conclusion of the feeds. Stages G, H and I were then added at 10 minute intervals.
  • the solids of this dispersion (11) was 49.5% and the particle size was 90 Nm.
  • a semi-gloss paint was prepared as in Example 1 with dispersion 11.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de revêtement aqueuse réticulable. Ladite composition contient un liant constitué d'une dispersion polymère d'addition comprenant des groupes à fonction acétoacétate combinée avec une amine de polyamine de polyoxyalkylène.
PCT/AU1994/000599 1993-09-29 1994-09-29 Compositions de revetement aqueuses reticulables WO1995009209A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU78048/94A AU678297B2 (en) 1993-09-29 1994-09-29 Cross-linkable aqueous coating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPM152593 1993-09-29
AUPM1525 1993-09-29

Publications (1)

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WO1995009209A1 true WO1995009209A1 (fr) 1995-04-06

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0744450A2 (fr) * 1995-05-24 1996-11-27 Rohm And Haas Company Compositions aqueuses contenant le polymére acétoacétate et l'amine multifuncionel
EP0778317A2 (fr) 1995-12-04 1997-06-11 Rohm And Haas Company Compositions aqueuses durcissables
WO1997045490A1 (fr) * 1996-05-28 1997-12-04 Eastman Chemical Company Melanges stables de polymeres a teneur en amino
US5891950A (en) * 1996-05-28 1999-04-06 Eastman Chemical Company Use of stable amino-functional latexes in water-based inks
US5962556A (en) * 1996-10-22 1999-10-05 Eastman Chemical Company Functional latexes resistant to hydrolysis
US6028155A (en) * 1997-05-21 2000-02-22 Eastman Chemical Company Surfactant-containing acetoacetoxy-functional and enamine-functional polymers
US6262169B1 (en) 1998-05-14 2001-07-17 Eastman Chemical Company Protonated amines for controlled crosslinking of latex polymers
US6512042B1 (en) 1996-12-18 2003-01-28 Rohm And Haas Company Waterborne crosslinkable coating compositions
US6660801B1 (en) 2000-04-20 2003-12-09 Rohm And Haas Company Coating composition with improved adhesion to friable surface
EP1529815A1 (fr) * 2003-11-10 2005-05-11 Rohm And Haas Company Dispersion aqueuse de polymère et son procédé d'utilisation
WO2006108570A1 (fr) * 2005-04-13 2006-10-19 Dsm Ip Assets B.V. Compositions aqueuses de revetement a base de vinyle
US7544733B2 (en) 1996-09-06 2009-06-09 Orica Australia Pty Ltd. Stain resistant water-borne coating composition
US20120264859A1 (en) * 2011-04-18 2012-10-18 Jianming Xu Copolymer dispersion for water whitening resistant coatings
US20160312047A1 (en) * 2015-04-21 2016-10-27 Rohm And Haas Company Co2 abating latex coating composition
US9499714B2 (en) 2013-03-15 2016-11-22 Ennis Paint, Inc. Controlled crosslinking of latex polymers with polyfunctional amines
US9796873B2 (en) 2016-02-02 2017-10-24 Ennis Paint, Inc. Linear polyglycidyl amine additives for controlled crosslinking of latex polymers
US10717800B2 (en) 2015-09-17 2020-07-21 Ennis Paint, Inc. Controlled crosslinking of latex polymers with polyfunctional amines
EP3907264A1 (fr) * 2020-05-06 2021-11-10 Henkel AG & Co. KGaA Composition adhésive durcissable pour applications de liaison à usages multiples
WO2023239912A1 (fr) * 2022-06-10 2023-12-14 Troy Technology Ii, Inc. Compositions de renforcement multifonctionnel à base de polyétheramine

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4987177A (en) * 1989-07-18 1991-01-22 E. I. Du Pont De Nemours And Company Coating composition of an acrylic polymer containing glycidyl groups and acetoacetoxy groups and an amino ester acrylic polymer
AU8970991A (en) * 1990-12-21 1992-06-25 Rohm And Haas Company Air curing polymer composition
EP0516074A1 (fr) * 1991-05-28 1992-12-02 Wacker-Chemie Gmbh Dispersions aqueuses de copolymères à groupes carbonyle, contenant des agents de réticulation aminoxy
US5270380A (en) * 1992-10-13 1993-12-14 Rohm And Haas Company Method for extending the open time of an aqueous coating composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4987177A (en) * 1989-07-18 1991-01-22 E. I. Du Pont De Nemours And Company Coating composition of an acrylic polymer containing glycidyl groups and acetoacetoxy groups and an amino ester acrylic polymer
AU8970991A (en) * 1990-12-21 1992-06-25 Rohm And Haas Company Air curing polymer composition
EP0516074A1 (fr) * 1991-05-28 1992-12-02 Wacker-Chemie Gmbh Dispersions aqueuses de copolymères à groupes carbonyle, contenant des agents de réticulation aminoxy
US5270380A (en) * 1992-10-13 1993-12-14 Rohm And Haas Company Method for extending the open time of an aqueous coating composition

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0744450A3 (fr) * 1995-05-24 1998-12-30 Rohm And Haas Company Compositions aqueuses contenant le polymére acétoacétate et l'amine multifuncionel
EP0744450A2 (fr) * 1995-05-24 1996-11-27 Rohm And Haas Company Compositions aqueuses contenant le polymére acétoacétate et l'amine multifuncionel
EP0778317A2 (fr) 1995-12-04 1997-06-11 Rohm And Haas Company Compositions aqueuses durcissables
WO1997045490A1 (fr) * 1996-05-28 1997-12-04 Eastman Chemical Company Melanges stables de polymeres a teneur en amino
US5891950A (en) * 1996-05-28 1999-04-06 Eastman Chemical Company Use of stable amino-functional latexes in water-based inks
US5998543A (en) * 1996-05-28 1999-12-07 Eastman Chemical Company Stable amino-containing polymer latex blends
US7544733B2 (en) 1996-09-06 2009-06-09 Orica Australia Pty Ltd. Stain resistant water-borne coating composition
US5962556A (en) * 1996-10-22 1999-10-05 Eastman Chemical Company Functional latexes resistant to hydrolysis
US6512042B1 (en) 1996-12-18 2003-01-28 Rohm And Haas Company Waterborne crosslinkable coating compositions
US6028155A (en) * 1997-05-21 2000-02-22 Eastman Chemical Company Surfactant-containing acetoacetoxy-functional and enamine-functional polymers
US6262169B1 (en) 1998-05-14 2001-07-17 Eastman Chemical Company Protonated amines for controlled crosslinking of latex polymers
US6942898B2 (en) 1999-05-07 2005-09-13 Rohm And Haas Company Coating composition with improved adhesion to friable surfaces
US6660801B1 (en) 2000-04-20 2003-12-09 Rohm And Haas Company Coating composition with improved adhesion to friable surface
EP1529815A1 (fr) * 2003-11-10 2005-05-11 Rohm And Haas Company Dispersion aqueuse de polymère et son procédé d'utilisation
WO2006108570A1 (fr) * 2005-04-13 2006-10-19 Dsm Ip Assets B.V. Compositions aqueuses de revetement a base de vinyle
US7833584B2 (en) 2005-04-13 2010-11-16 Dsm Ip Assets B.V. Aqueous vinyl coating compositions
US20120264859A1 (en) * 2011-04-18 2012-10-18 Jianming Xu Copolymer dispersion for water whitening resistant coatings
CN102746601A (zh) * 2011-04-18 2012-10-24 罗门哈斯公司 耐水白涂料用共聚物分散体
US8772386B2 (en) 2011-04-18 2014-07-08 Rohm And Haas Company Copolymer dispersion for water whitening resistant coatings
CN102746601B (zh) * 2011-04-18 2014-11-26 罗门哈斯公司 耐水白涂料用共聚物分散体
US10377878B2 (en) 2013-03-15 2019-08-13 Ennis Paint, Inc. Controlled crosslinking of latex polymers with polyfunctional amines
US9499714B2 (en) 2013-03-15 2016-11-22 Ennis Paint, Inc. Controlled crosslinking of latex polymers with polyfunctional amines
US20160312047A1 (en) * 2015-04-21 2016-10-27 Rohm And Haas Company Co2 abating latex coating composition
US10717800B2 (en) 2015-09-17 2020-07-21 Ennis Paint, Inc. Controlled crosslinking of latex polymers with polyfunctional amines
US9796873B2 (en) 2016-02-02 2017-10-24 Ennis Paint, Inc. Linear polyglycidyl amine additives for controlled crosslinking of latex polymers
US10442954B2 (en) 2016-02-02 2019-10-15 Ennis Paint, Inc Linear polyglycidyl amine additives for controlled crosslinking of latex polymers
EP3907264A1 (fr) * 2020-05-06 2021-11-10 Henkel AG & Co. KGaA Composition adhésive durcissable pour applications de liaison à usages multiples
WO2021223991A1 (fr) * 2020-05-06 2021-11-11 Henkel Ag & Co. Kgaa Composition adhésive durcissable pour applications de liaison multi-usage
US11939496B2 (en) 2020-05-06 2024-03-26 Henkel Ag & Co. Kgaa Curable adhesive composition for multi-purpose bonding applications
WO2023239912A1 (fr) * 2022-06-10 2023-12-14 Troy Technology Ii, Inc. Compositions de renforcement multifonctionnel à base de polyétheramine

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