WO1999032563A2 - Revetements de latex faiblement toxiques pour l'environnement - Google Patents

Revetements de latex faiblement toxiques pour l'environnement Download PDF

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Publication number
WO1999032563A2
WO1999032563A2 PCT/US1997/024224 US9724224W WO9932563A2 WO 1999032563 A2 WO1999032563 A2 WO 1999032563A2 US 9724224 W US9724224 W US 9724224W WO 9932563 A2 WO9932563 A2 WO 9932563A2
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WO
WIPO (PCT)
Prior art keywords
esters
ether
hydroxyl bearing
ethers
matter
Prior art date
Application number
PCT/US1997/024224
Other languages
English (en)
Other versions
WO1999032563A3 (fr
Inventor
Gerald Sugerman
Original Assignee
Gerald Sugerman
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 Gerald Sugerman filed Critical Gerald Sugerman
Priority to PCT/US1997/024224 priority Critical patent/WO1999032563A2/fr
Priority to CA002314975A priority patent/CA2314975A1/fr
Priority to AU60143/98A priority patent/AU6014398A/en
Priority to EP97954808A priority patent/EP1549142A4/fr
Priority to BR9714916-0A priority patent/BR9714916A/pt
Publication of WO1999032563A2 publication Critical patent/WO1999032563A2/fr
Publication of WO1999032563A3 publication Critical patent/WO1999032563A3/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
    • 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
    • C09D5/024—Emulsion paints including aerosols characterised by the additives

Definitions

  • This invention has the advantage of
  • this invention have vapor pressures below 0.1 mm Hg at 25°C,
  • 22 contain at least one basic nitrogen, and at least one carbon to
  • specific examples of such useful non-acryl and/or N-vinyl 6 ligands include those most preferable have a water solubility 1 exceeding 2% at 25°C.
  • Table III examples of such non- hydroxyl bearing unsaturated esters and ether and ether- esters as are useful in the practice of the instant invention are provided in Table III. These examples are intended to be illustrative rather than exhaustive of the scope of useful materials.
  • Table III (3A) trimethylol propane bis (2-methyl) -2-propenoate ester, mono vinyl ether (3B) 1,2, 3-propane triol tris 2-butenoate ester (3C) penta erethyritol 2-propenolato, tris 2-propenoate ester (3D) hexanoic acid 6-acetoxy, (2-propenoato) ethyl ester (3E) fumaric acid bis isodecyl ester (3F) maleic acid bis cinnamyl ester (3G) furoic acid vinyl ester (3H) 1,2, 3-hexanetriol 1,2-bis vinyl ether, phenyl carboxylate ester (3J) trimeric 2-butene-l,
  • amphoteric detergents and certain organometalics based on tetravalent titanium or zirconium. These last have been found to contribute significantly to substrate adhesion and improved corrosion resistance on wood, metalic and ceramic substrates, and to be particularly useful in maximizing color intensities of carbon black, azo and phthalocyanine based pigments.
  • Specific examples of the preferred types of hypersurfactants are given in Table V. These examples are intended to be illustrative rather than exhaustive of the scope of useful materials.
  • hydroxylated and non-hydroxyl bearing esters optionally in combination with partially esterified and/or etherified glycols, and or polyols, in place of either component (set) alone, (as is amply demonstrated in example No. 4.), or of unsaturated analogous unsaturated amides, for a portion of the aforementioned unsaturated ethers, esters or ether-esters disclosed above, and/or fluorination of one or more of the species of components heretofore described as necessary to the successful practice of this invention; however such non-critical modifications, and/or combinations of relevant species types, must be considered as within the scope of this disclosure.
  • Example #1 This example teaches the superiority of the present invention versus the prior art with respect to the productivity, VOC emissions, and performance quality in a masonry sealer application.
  • a masonry sealer formulation was prepared by the sequential dispersion of the indicated components (pigment dispersion times and grind quality achievement was noted) .
  • sealer efficacy was measured by weighing the dry casting, then impounding a 6" depth of water, or alternatively 6% salt solution, on such a casting for twenty four hours, then draining and weighing the drained casting. The weight percent of water, and independently that of 6% salt solution, adsorbed by said castings were used to determine sealer efficacy. The results of this study are given in Table No. 1.
  • Formulation in parts by weight; (in order of addition) water 200.0; neutralizer 1 , as shown; surfactant 3 , as shown, biocides 2 , 18.50; hydro ⁇ y ethyl cellulose, 5.00; potassium tris polyphosphate, 2.00; defoamer 2 , 1.00; coalescent 3 , as shown; ultramarine blue pigment, 0.25; rutile titanium dioxide, 200.0, American process zinc oxide, 25; platey talc, 250; water, 49.98; AC-625 Acrylic latex resin 3 , 352.0; defoamer 2 , 0.98; surfactant 0 , coalescent b , as shown,; water, 24.99; and sodium nitrite 2.30; thixotrope 4 , as shown (required) to adjust system viscosity to 85-90 KU at 75° F.
  • Formulation 1 2 3 4 5 neutralizer amp-95/1.98 1B/2.00 1H/1.80 1G/2.20 1D/1.78 surfactant (a) Tamol 850 7 /14.85 5A/1.80 5E/1.75 5K/1.55 5H/1.50 coalescent (a) Propylene glycol none 4J/4.50 none
  • This example teaches the superiority of the present invention versus the prior art with respect to the productivity, VOC emissions, and performance quality in a direct to metal, maintenance coating application.
  • Direct to metal coatings were prepared by the sequential dispersion of the indicated components (pigment dispersion times were noted) .
  • the resulting coating was spray applied to sandblasted smooth surface 24" X 8" carbon steel test panels at application rate of one gallon per 250 square feet. After 120 hours of drying @ 72° F and 85% humidity, edge sealing and scribing, the coatings' corrosion resistance performance were each measured by QUV cabinet exposure [cyclic exposure to UV radiation, 4% saline solution, and varying temperature (25°-80° C) ] .
  • Formulation in parts by weight (in order of addition) : water, 50.0; neutralizer, as shown; Surfactant 3 , as shown, biocide 1 , 4.00; oxidized polyethylene wax, 4.00; (disperse wax) polyurethane thixotrope 2 , as shown; defoamer 3 , 2.00; coalescent 3 , as shown, ultramarine blue pigment, 0.25; rutile titanium dioxide, 125; zinc aluminate 150; Acrylic latex resin 4 , 64.0; (disperse particulates to Hegman 7.5+) .
  • Formulation 1 2 3 4 5 6 neutralizer DMAMP-80 12.5 1A/4.00 1C/1.80 1E/2.20 1J/1.78 DMAMP- 80 5 /6.25 1A/ 2.00 surfactant (a) Triton CFloVlO.OO 5D/1.80 5F/1.75 5C/1.55 5J/1.50 Triton
  • Formulation 7 8 9 10 11 12 neutralizer DMAMP-80 5 /12.5 1A 4.00 1C/1.80 1E/2.20 1J/1.78 DMAMP 80 5 /6.25 surfactant (a) Triton CFloVlO.OO 5D/1.80 5F/1.75 5C/0.55 5J/1.50 Triton CFlO/5.00 surfactant (b) none none 5A/1.00 Triton none 5D/1.25 CF10 6 /2.C 1 thixotrope 2 15.00 5.00 5.50 8.70 5.30 9.32 coalescent (a) Dipropylene glycol PmPE 7 4B/12.00 4E/10.5 4K/8.25 PmPE 7 /22.3
  • Example #3 This example teaches the superiority of the present invention versus the prior art with respect to productivity, VOC emissions, and performance quality in a polyvinyl acetate based interior flat architectural paint application.
  • Interior flat paints were prepared by the sequential dispersion of the indicated components (pigment dispersion times, and dispersion efficacy were noted) .
  • the resulting coating was brush applied to unprimed drywall (gypsum sheet) @ 72° F and 80% humidity, coverage, stain removal, and scrubability performance were each measured after 7 days of drying 72+ ⁇ - 2°F @ 65-80% humidity.
  • Formulation in parts by weight; (in order of addition) water, 200.0; neutralizer 1 , as shown; surfactant 3 , as shown, biocides 2 , 1.00; hydroxy ethyl cellulose, as shown; potassium tris polyphosphate, as shown; defoamer 3 , 1.00; coalescent 3 , as shown; ultramarine blue pigment, 0.25; rutile titanium dioxide, 250.0, water washed clay 4 , 50.0; calcium carbonate 5 , as shown; diatomite 6 , 50.0; water, 49.98; PVA latex resin 7 , 352.0; defoamer 2 , 0.98; coalescent 0 , as shown ; water, 100 .0;and sodium nitrite 2.30; thixotrope 8 , as shown (required) to adjust system viscosity to 90- 100 KU at 75° F.
  • neutralizer 1 as shown
  • surfactant 3 as shown, biocides 2 , 1.00; hydroxy ethyl
  • Formulation 1 neutralizer 28% ammonia aq. 1B/2.00 1H/1.80 1G/2.20 1D/1.78 28% ammonia
  • HEC(QP-4400) 5.50 1.20 1.35 1.25 1.40 1.35 surfactant (a) Tamol 731/6.90 5E/1.80 5J/1.75 5C/1.55 5F/1.5 Tamol 731/6 Triton N101/3.31 Triton N101/3.31 coalescent (a) Propylene glycol 4A/6.00 4 F/7.00 4H/5.50 4E/7.00 4E/7.00
  • Formulation 8 10 neutralizer 28% ammonia aq. 1B/2.00 1H/1.80 1H/1.80
  • HEC HEC (QP-4400) 5.50 1.20 1.35 1.25 surfactant (s) Tamol 731/ 6.9 Tamol 731/ 3.9 5J/ 1.75 Tamol 731/ 6.9 Triton N101/ 3.31 5J/1.0 Triton N101/ 3. coalescent (a) Propylene glycol 4A/6.00 Propylene glycol 4H/5.50 51.95 51.95 calcite 50 100 125 150 coalescent (b) 4E/2.00 2A/ 26.4 3C/ 12.60 3F/ 18.50 thixotrope 8 3.5 3.0 3.1 2.7
  • Formulation 1 2 3 4 5 6 7
  • Part A neutralizer 28% 1A 1H 1H 1H IB IB ammonia aq.
  • Part B formulation Texanol 8.00 4.00 4.00 diethylene glycol 18.20 9.10 9.10 mono butyl ether 2A 12.05 6.00 6.00 6.00 6.00 2C 4.40 10.70 3B 4.20 6.00 4G 1.90 2.90 1.05 6.20 4J
  • Example #4 This example teaches the superiority of the present invention versus the prior art with respect to the productivity, VOC emissions, and performance quality in a force dried, clear, protective, two component acrylic latex cured - waterborne epoxy, wood cabinet coating.
  • Component A
  • PBW sodium nitrite 0.15 and defoamer (Patcote 519-Patco Coatings Inc.) were admixed with 95.85 PBW of (Acrylic latex-Maincote AE 58) , and said emulsion was subsequently mixed with 50 PBW of Component B, formulated by blending various additives, as shown, into 12.5 PBW of Genepoxy 370-H55- Daubert Chemical Co., and diluting as necessary with water to produce a total part B weight of 25 parts.
  • Thixatrope 1 was added, as required, to provide an initial mix nonvolatile reactive amines, in combination with hydroxyl bearing unsaturated esters and/or ethers and/or ether-esters, and/or non- hydroxyl bearing unsaturated esters and/or ethers and/or ether- esters and incompletely etherified and/or esterified oligomeric glycols and/or oligools as (partial or full) replacements for conventionally employed volatile amines and/or ammonia as neutralizers, and organic solvents as coalescents, respectively may be employed to substantially enhance the processability (pot life) , mechanical and chemical resistance properties ( abrasion and stain resistance respectfully) as well as attain VOC reduction in wood coatings.
  • a further benefit of the instant invention as applied to wood coatings is that unlike conventionally coalesced waterborne coatings, e.g. formulation D-l latex formulations based upon the teachings of this invention, e.g. formulations D-2 through D-7, do not cause significant grain rise, thereby virtually eliminating the necessity for intercoat sanding.
  • formulations D-3,D-5, and D-6 may provide considerable benefits relative to their conventional counterparts, such as Formulation No. 1; however, omission of one or more of the components of the combination herein disclosed leads to inferior results as compared to the inclusion of the full compliment.
  • Example #5 This example teaches the superiority of the present invention versus the prior art with respect to the productivity, VOC emissions, and performance quality in waterborne flexographic inks.
  • a latex flexographic ink formulation was prepared by the sequential dispersion of the indicated components (pigment dispersion times and grind quality achievement was noted) .
  • the resulting ink was applied via a #6 wire wound rod to bond paper, and permitted to dry. Dry time (to touch) was measured under conditions, of 72° F and 85% humidity. After 6 hours of drying @, 72° F and 85% humidity, heat seal resistance performance (face to face) was measured at 25 psig. and 2 seconds contact time) the results of this study are given in Table No. 5.
  • Formulation in parts by weight; (in order of addition) E-2350 resin 267; neutralizer, as shown; surfactant, as shown; Defo 1020 defoamer 4.00 Ultra Inc.; coalescent 3 , as shown; calcium lithol pigment 50% presscake, 400-Sun Chemical Corp.; Michemlube wax 5- Michelman Inc., water, as required in order to produce a viscosity of 27 seconds using a #2 Zahn cup.
  • Relative dry ink color intensities were measured by integrating thin film reflectance spectra at 300-600 urn wavelengths using a spectrophotometer after 48 hours of drying at the above conditions
  • Formulation neutralizer 28% ammonia aq, 1D/2.00 IH/1.40 2.00 surfactant Tamol 850/4.95 5A/1.80 5E/1.75 coalescent isopropanol/48 2A/10.5 2E/20.0 Texanol/24 3C/15.5 4H/5.5
  • Example #6 This example teaches the utility of the instant invention in the production of superior waterborne anti-scuff overprint coatings for graphic arts applications.
  • a 30% solution of water reducible styrene-acrylic copolymer resin in water was prepared by admixture of the indicated neutralizing agent-as shown, water, and Air Product Corp's Flexbond 28 resin.
  • Thirty parts by weight (PBW) of the preceding solution were admixed with 50 PBW of styrene- acrylic latex resin (Flexbond 285, Air Products Corp.), coalescent, and surfactant (s) -as shown, poly ethylene wax, 2 PBW, and sufficient water to dilute the system to 100 PBW.
  • the resulting coating was applied, in line on a high speed six color lithographic cold web press, to a solid four color print pattern, followed by in line infrared drying, and folding.
  • Formulation 2 neutralizer 28% ammonia/ 6.00 AMP 95 1 / 8. 00 AMP 95/ 8.00 coalescent (s) isopropanol/ 12 isopropanol/ 12 2G/ 4.50 surfactant Tamol 850/ 2.05 Tamol 850/ 2.05 5K/ 0.75
  • Formulation 5 neutralizer 1G/ 6.00 1G/ 6.00 1G/ 6.00 coalescent (s) 2G/ 4.50 2G/ 4.50 3C/ 3.65 4C/ 0.85 surfactant Tamol 850/ 2.05 5K/ 0.75 2K/ 0.75

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

L'invention concerne des associations d'amines réactives non volatiles et d'esters et/ou d'éthers et/ou d'éthers-esters insaturés hydroxylés (et/ou des associations d'esters et/ou d'éthers et/ou d'éthers-esters insaturés non hydroxyléas et de glycols et/ou d'oligools oligomères éthérifiés et/ou estérifiés hydroxylés saturés), utilisées pour remplacer respectivement les traditionnels amines volatiles et/ou l'ammoniac servant de neutralisants et les solvants organiques servant de coalescents. Il s'est avéré que ces associations permettent la production de revêtements, peintures, et encres à base de latex de copolymère acrylique et vinylique à teneur en composés organiques volatils faible à nulle. On peut encore obtenir une amélioration en substituant des hyper-tensioactifs aux traditionnels savons et/ou dispersants et/ou détergents, en association avec les amines réactives non volatiles précitées, notamment sous forme de dispersants particulaires dans des revêtements pigmentés et/ou renforcés.
PCT/US1997/024224 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement WO1999032563A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
PCT/US1997/024224 WO1999032563A2 (fr) 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement
CA002314975A CA2314975A1 (fr) 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement
AU60143/98A AU6014398A (en) 1997-12-19 1997-12-19 Low environmental toxicity latex coatings
EP97954808A EP1549142A4 (fr) 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement
BR9714916-0A BR9714916A (pt) 1997-12-19 1997-12-19 Cobertura de látex com baixo teor de toxicidade para o meio ambiente

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1997/024224 WO1999032563A2 (fr) 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement

Publications (2)

Publication Number Publication Date
WO1999032563A2 true WO1999032563A2 (fr) 1999-07-01
WO1999032563A3 WO1999032563A3 (fr) 2005-05-06

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PCT/US1997/024224 WO1999032563A2 (fr) 1997-12-19 1997-12-19 Revetements de latex faiblement toxiques pour l'environnement

Country Status (4)

Country Link
EP (1) EP1549142A4 (fr)
AU (1) AU6014398A (fr)
CA (1) CA2314975A1 (fr)
WO (1) WO1999032563A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004022653A2 (fr) * 2002-09-05 2004-03-18 Vocfree, Inc. Revetement a sechage rapide
US6762230B2 (en) 2001-02-22 2004-07-13 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
EP1620480A1 (fr) * 2003-04-03 2006-02-01 Vocfree, Inc. Systemes de latex coalescents exempts de composes organiques volatils
US7071364B2 (en) 2000-12-21 2006-07-04 Shell Oil Company Branched primary alcohol compositions and derivatives thereof
WO2008081036A1 (fr) * 2007-01-05 2008-07-10 Taminco Agents neutralisants amines pour peintures organiques à faible teneur en composés volatils
US7812079B2 (en) 2001-02-22 2010-10-12 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
CN102383334A (zh) * 2011-10-24 2012-03-21 吴江市天源塑胶有限公司 二氯乙烯水性涂料
US10835485B2 (en) 2011-01-24 2020-11-17 Basf Se Oral health improving compositions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343884A (en) * 1980-12-29 1982-08-10 Andrews Paper & Chemical Co., Inc. Diazotype developing process and acidic developer with amine base salt

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3954648A (en) * 1969-12-22 1976-05-04 Pennwalt Corporation Coatings removal composition containing an alkali metal hydroxide, an oxygenated organic solvent, and an amine
US5349026A (en) * 1992-11-20 1994-09-20 Rohm And Haas Company Reactive coalescents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343884A (en) * 1980-12-29 1982-08-10 Andrews Paper & Chemical Co., Inc. Diazotype developing process and acidic developer with amine base salt

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1549142A2 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7071364B2 (en) 2000-12-21 2006-07-04 Shell Oil Company Branched primary alcohol compositions and derivatives thereof
US7148375B2 (en) 2000-12-21 2006-12-12 Shell Oil Company Branched primary alcohol compositions and derivatives thereof
US7812079B2 (en) 2001-02-22 2010-10-12 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
US6762230B2 (en) 2001-02-22 2004-07-13 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
US8110624B2 (en) 2001-02-22 2012-02-07 The Valspar Corporation Coating compositions containing low VOC compounds
WO2004022653A3 (fr) * 2002-09-05 2004-04-22 Vocfree Inc Revetement a sechage rapide
WO2004022653A2 (fr) * 2002-09-05 2004-03-18 Vocfree, Inc. Revetement a sechage rapide
US7157505B2 (en) 2002-09-05 2007-01-02 Vocfree, Inc. Fast drying coatings
AU2003265905B2 (en) * 2002-09-05 2008-01-31 Vocfree, Inc. Fast drying coatings
EP1620480A1 (fr) * 2003-04-03 2006-02-01 Vocfree, Inc. Systemes de latex coalescents exempts de composes organiques volatils
EP1620480A4 (fr) * 2003-04-03 2008-04-23 Vocfree Inc Systemes de latex coalescents exempts de composes organiques volatils
WO2008081036A1 (fr) * 2007-01-05 2008-07-10 Taminco Agents neutralisants amines pour peintures organiques à faible teneur en composés volatils
US10835485B2 (en) 2011-01-24 2020-11-17 Basf Se Oral health improving compositions
CN102383334A (zh) * 2011-10-24 2012-03-21 吴江市天源塑胶有限公司 二氯乙烯水性涂料

Also Published As

Publication number Publication date
WO1999032563A3 (fr) 2005-05-06
AU6014398A (en) 1999-07-12
EP1549142A2 (fr) 2005-07-06
CA2314975A1 (fr) 1999-07-01
EP1549142A4 (fr) 2009-08-19

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