SE530420C2 - A waterborne binder composition and its use - Google Patents
A waterborne binder composition and its useInfo
- Publication number
- SE530420C2 SE530420C2 SE0601914A SE0601914A SE530420C2 SE 530420 C2 SE530420 C2 SE 530420C2 SE 0601914 A SE0601914 A SE 0601914A SE 0601914 A SE0601914 A SE 0601914A SE 530420 C2 SE530420 C2 SE 530420C2
- Authority
- SE
- Sweden
- Prior art keywords
- coalescing agent
- glycerol
- weight
- composition according
- triester
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 239000011230 binding agent Substances 0.000 title claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 66
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 54
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 claims description 32
- 150000005691 triesters Chemical class 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 22
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 150000005690 diesters Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
- 229940005605 valeric acid Drugs 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 239000000565 sealant Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 11
- 239000000975 dye Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ISJNRPUVOCDJQF-UHFFFAOYSA-N (1-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)CC(C)(C)C(O)OC(=O)C(C)C ISJNRPUVOCDJQF-UHFFFAOYSA-N 0.000 description 1
- REAAUFDFYPKMIR-UHFFFAOYSA-N 2,3-bis(2-methylpropanoyloxy)propyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCC(OC(=O)C(C)C)COC(=O)C(C)C REAAUFDFYPKMIR-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0622—Polyvinylalcohols, polyvinylacetates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0632—Polystyrenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/065—Polyurethanes
Description
530 420 Enligt föreliggande uppfinning har det helt oväntat blivit möjligt att producera en Vattenburen bindemedelskomposition innefattande ett vattendispergerbart polymert bindßmêdël 0011 ett koaliseringsmedel innefattande glyceryltiiestrar. Triestrarna i koaliseringsmedlet väljsiur en grupp bestående av tripropionin (triester av glycerol och propionsyra), tributyrin (triester av glycerol och butyrsyra), tri-isobutyrin (triester av glycerol och isobutyrsyra) eller trivalerin (triester av glycerol och valeriansyra) eller kombinationer av två eller flera av dessa. Förutom att vara väl förenliga med blandningar innehållande typiska vattenburna polymerdispersioner, förbättrar triestrarna i föreliggande uppfinning filrnbildiiingsegenskaper, vilket gör dem _ utmärkta som koaliseringsmedel i Vattenburen färg, lim och tätningsmedel. Som nämnts förut är koaliseringsmedlet i föreliggande uppfinning en triester till skillnad från andra esterbaserade koaliseringsmedel som används i vattenburna bindemedelsforrnuleringar vilka vanligtvis är monoestrar eller diestrar, t.ex. dikarboxylsyror förestrade med alkoholer eller dioler förestrade med syror. According to the present invention, it has quite unexpectedly become possible to produce a waterborne binder composition comprising a water-dispersible polymeric binder 0011 a coalescing agent comprising glyceryl thiesters. The triesters of the coalescing agent are selected from a group consisting of tripropionin (triester of glycerol and propionic acid), tributyrin (triester of glycerol and butyric acid), tri-isobutyrin (triester of glycerol and isobutyric acid) or trivalerine (triester of glycerol and valeric acid) or combinations fl era of these. In addition to being well compatible with mixtures containing typical waterborne polymer dispersions, the triesters of the present invention improve formation properties, making them excellent as coalescing agents in waterborne paint, adhesives and sealants. As mentioned previously, the coalescing agent of the present invention is a triester unlike other ester-based coalescing agents used in waterborne binder formulations which are usually monoesters or diesters, e.g. dicarboxylic acids esterified with alcohols or diols esterified with acids.
Experiment visar att triestrarna i uppfinningen är förenliga med många olika polymerdispersioner och att de effektivt sänker MFFT i vattenhaltiga polymerdispersioner.Experiments show that the triesters of the invention are compatible with many different polymer dispersions and that they effectively lower MFFT in aqueous polymer dispersions.
Dispersionskonceptet enligt uppfinningen inkluderar emulsioner, eftersom definitionen av en emulsion är en dispersion av små droppar av en vätska i en annan vätska. Förutom den förut nämnda höga reduceringseffekten av MFFT, god lagringsstabilitet och god törenlighet med polymerdispersioner, medför triestrama i föreliggande uppfinning minimala EHS- påverkningar. Trots sin lagringsstabilitet är triestrama biologiskt nedbrytbara, dvs. de orsakar minimala miljö- eller hälsoproblem. Triestrarna i föreliggande uppfinning klassas inte SOIII VOC-föreningar i Europa på grund av sin höga kokpunkt. Kombinationen av hög kokpunkt och hög effektivitet är mycket ovanlig för ett koaliseringsmedel. Vid användning som koaliseringsmedel i en Vattenburen bindemedelskomposition, möjliggör den ringa mjukgörande egenskapen hos föreliggande uppfinnings tiiestrar, bildandet av en hård film med en acceptabel hastighet på hårdhetsutvecklingen. Triestrama i föreliggande uppfinning är välkända föreningar som är kommersiellt tillgängliga, men som aldrig tidigare påtänkts som koaliseringsmedel.The dispersion concept of the invention includes emulsions, since the fi nition of an emulsion is a dispersion of droplets of one liquid in another liquid. In addition to the aforementioned high reduction effect of MFFT, good storage stability and good dryness with polymer dispersions, the triesters in the present invention have minimal EHS effects. Despite their storage stability, the triestrams are biodegradable, ie. they cause minimal environmental or health problems. The triesters of the present invention are not classified as SOIII VOC compounds in Europe due to their high boiling point. The combination of high boiling point and high efficiency is very unusual for a coalescing agent. When used as a coalescing agent in a waterborne binder composition, the slight emollient property of the present invention tester enables the formation of a hard film with an acceptable rate of hardness development. The triestrams of the present invention are well known compounds which are commercially available, but which have never before been intended as a coalescing agent.
Koaliseringsmedlet i denna uppfinning består av 75-l00%, företrädesvis 90-100 vikt-% av en eller flera triestrar av glycerol och en syra vald ur en grupp bestående av propionsyra, butyrsyra, isobutyrsyra och valeriansyra. Återstående delen av koaliseringsmedlet består av motsvarande monoestrar och diestrar av glycerol och ovanstående syror. Koaliseringsmedlet i 530 420 is föreliggande uppfinning kan innefatta ett eller flera kända koaliseringsmedel utöver triestern eller triestrarna. Det kända koaliseringsmedlet eller -medlen kan utgöra 1-50 vikt-% av det totala koaliseringsmedlet, företrädesvis 1-25%. Koaliseringsmedlet utgör 1-30 vikt-% av det fasta polymermaterialet, företrädesvis 2-20% eller 2-10%.The coalescing agent of this invention consists of 75-100%, preferably 90-100% by weight of one or three triesters of glycerol and an acid selected from the group consisting of propionic acid, butyric acid, isobutyric acid and valeric acid. The remaining part of the coalescing agent consists of the corresponding monoesters and diesters of glycerol and the above acids. The coalescing agent of the present invention may comprise one or more known coalescing agents in addition to the triester or triesters. The known coalescing agent or agents may constitute 1-50% by weight of the total coalescing agent, preferably 1-25%. The coalescing agent constitutes 1-30% by weight of the solid polymeric material, preferably 2-20% or 2-10%.
Bindemedlet i farg-, lim» eller tätningsmedelskompositionen i föreliggande uppfinning är en homo- eller sampolymer innefattande monomerenheter av akrylat, metakrylat, vinylacetat och/eller enheter av uretan eller uretan/urea. Typiska bindemedelspolymerer är styren-akrylat sampolymerer, akrylat-metakrylat sampolymerer, sampolymerer av vinylacetat och akrylat eller metakrylat, vinylacetat homopolymerer, vinylversatat homopolymerer och sampolymerer av etylen och vinylacetat eller vinylversatat. Således kan samma principiella typer av vattenhaltiga polymerer användas i vattenhaltiga fargformuleringar, lim och tätningsmedel.The binder in the paint, adhesive or sealant composition of the present invention is a homo- or copolymer comprising monomer units of acrylate, methacrylate, vinyl acetate and / or units of urethane or urethane / urea. Typical binder polymers are styrene-acrylate copolymers, acrylate-methacrylate copolymers, copolymers of vinyl acetate and acrylate or methacrylate, vinyl acetate homopolymers, vinyl-displaced homopolymers and copolymers of ethylene and vinyl acetate or vinyl-versated. Thus, the same basic types of aqueous polymers can be used in aqueous paint formulations, adhesives and sealants.
Förutom det vattendispergerbara polymera bindelmedlet och koaliseringsmedlet kan en fárgkomposition innehålla pigment, fyllmedel samt relevanta tillsatser, såsom skumdämpare, . pigmenterade vätningstillsatser och utj ämningshjälpmedel.In addition to the water-dispersible polymeric binder and coalescing agent, a paint composition may contain pigments, fillers and relevant additives, such as defoamers,. pigmented wetting additives and leveling aids.
Uppfinningen belyses ytterligare i utföringsexemplen nedan. Exemplen ska betraktas som illustrativa och inte på något sätt begränsande.The invention is further illustrated in the embodiments below. The examples are to be considered as illustrative and not restrictive in any way.
Exempel l, 2 och 3 belyser effekten av tripropionin som koaliseringsmedel i en dispersion av en akrylat homopolymer. Exempel 4 belyser effekten av tributyrin som koaliseringsmedel i en dispersion av samma sort. Exempel 5 belyser ettjärnförelsefiirsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande dispersion.Examples 1, 2 and 3 illustrate the effect of tripropionine as a coalescing agent in a dispersion of an acrylate homopolymer. Example 4 illustrates the effect of tributyrin as a coalescing agent in a dispersion of the same kind. Example 5 illustrates an iron test which shows the effect of a commercial coalescing agent in the corresponding dispersion.
Exempel 6 och 7 belyser effekten av tripropionin som koaliseringsmedel i en dispersion av en styren-akrylat sampolymer. Exempel 8 belyser ett jämförelseförsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande dispersion.Examples 6 and 7 illustrate the effect of tripropionine as a coalescing agent in a dispersion of a styrene-acrylate copolymer. Example 8 illustrates a comparative experiment showing the effect of a commercial coalescing agent in the corresponding dispersion.
Exempel 9, 10 och 11 belyser effekten av tripropionin som koaliseringsmedel i en dispersion av en styren-akrylat sampolymer. Exempel 12 belyser effekten av tributyrin som koaliseringsmedel i en dispersion av samma sort. Exempel 13 belyser ett järnförelseförsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande dispersion. 530 420 Exempel 14 och 15 belyser effekten av tripropionin som koaliseringsmedel i en dispersion av * en vinylacetat/vinyl -versatat sampolymer. Exempel 16 belyser ett jämfiårelseforsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande dispersion.Examples 9, 10 and 11 illustrate the effect of tripropionine as a coalescing agent in a dispersion of a styrene-acrylate copolymer. Example 12 illustrates the effect of tributyrin as a coalescing agent in a dispersion of the same kind. Example 13 illustrates an ironing test showing the effect of a commercial coalescing agent in the corresponding dispersion. Examples 14 and 15 illustrate the effect of tripropionine as a coalescing agent in a dispersion of a vinyl acetate / vinyl-translated copolymer. Example 16 illustrates a comparative experiment showing the effect of a commercial coalescing agent in the corresponding dispersion.
Exempel 17 och 18 belyser effekten av tripropionin som koaliseringsmedel i en dispersion av en Styren-akrylat sampolymer. Exempel 19 belyser effekten av tributyrin som koaliseringsmedel i en dispersion av samma sort. Exempel 20 belyser ett jämfórelsefórsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande dispersion.Examples 17 and 18 illustrate the effect of tripropionine as a coalescing agent in a dispersion of a styrene-acrylate copolymer. Example 19 illustrates the effect of tributyrin as a coalescing agent in a dispersion of the same kind. Example 20 illustrates a comparative experiment showing the effect of a commercial coalescing agent in the corresponding dispersion.
Exempel 21, 22 och 23 belyser tripropionins koaliseringsfórrnåga i en fargforrnulering innehållande en dispersion av en Styren-akrylat sampolymer som bindemedel. Exempel 24 belyser ett järnforelsetörsök som visar effekten av ett kommersiellt koaliseringsmedel i motsvarande fargformulering. Resultat visas i figur I .Examples 21, 22 and 23 illustrate the coalescence ability of tripropionin in a color formulation containing a dispersion of a styrene-acrylate copolymer as a binder. Example 24 illustrates an iron compound test showing the effect of a commercial coalescing agent in the corresponding color formulation. Results are shown in Figure I.
Exempel 1 l00g av en dispersion av en akrylat homopolymer, Finndisp A2002 (Forcit), med ett innehåll av fast polymermaterial på 45 víkt-% och en MFFT på 54°C blandades med 4,5 g tripropionin för att få en blandning innehållande 10% koaliseringsmedel (tillsatsen av koaliseringsmedel är beräknad på fast polymermaterial). Blandningen rordes om med hjälp av en propelleromrörare i 15 minuter och tilläts vila över natten innan testning. MF FT uppmättes till 19°C.Example 1100 g of a dispersion of an acrylate homopolymer, Finndisp A2002 (Forcit), having a solids polymer content of 45% by weight and an MFFT of 54 ° C were mixed with 4.5 g of tripropionin to give a mixture containing 10% coalescing agent (the addition of coalescing agent is calculated on solid polymeric material). The mixture was stirred with a propeller stirrer for 15 minutes and allowed to stand overnight before testing. MF FT was measured at 19 ° C.
Exempel 2 Förfarandet enligt exempel 1 upprepades förutom att mängden tripropionin som tillsattes var 6,75g (15%). MFF T uppmättes till 15°C.Example 2 The procedure of Example 1 was repeated except that the amount of tripropionin added was 6.75 g (15%). MFF T was measured at 15 ° C.
Exempel 3 Förfarandet enligt exempel 1 upprepades förutom att mängden tripropionin som tillsattes var 9,0g (20%). MFFT upprnättes till 4°C.Example 3 The procedure of Example 1 was repeated except that the amount of tripropionin added was 9.0 g (20%). MFFT was reached at 4 ° C.
Exempel 4 Förfarandet enligt exempel 1, 2 och 3 upprepades förutom att tributyrin i stället för tripropionin tillsattes dispersionen av akrylat homopolymeren. MFFT uppmättes till 24°C, °C respektive O°C. 530 420 Exempel 5 _ Förfarandet enligt exempel 1, 2 och 3 upprepades förutom att ett kommersiellt koaliseringsmedel, 2,2,4-trimetylpentandiol monoisobutyrat (NX795), tillsatteš istället .för tripropionin. MFFT uppmättes till 25°C, l4°C respektive 0°C.Example 4 The procedure of Examples 1, 2 and 3 was repeated except that tributyrin was added to the dispersion of the acrylate homopolymer instead of tripropionin. MFFT was measured at 24 ° C, ° C and 0 ° C, respectively. 530 420 Example 5 The procedure of Examples 1, 2 and 3 was repeated except that a commercial coalescing agent, 2,2,4-trimethylpentanediol monoisobutyrate (NX795), was added instead of tripropionin. MFFT was measured at 25 ° C, 14 ° C and 0 ° C, respectively.
Exempel 6 _ 100g av en dispersion av en styren-akrylat sampolymer, Finndisp A10 (Forcit), med ett innehåll av fast polymermaterial på 50 vikt-% och en MFFT på 18°C blandades med 1,00 g tripropionin for att få en blandning innehållande 2% koaliseringsmedel. Blandningen IÖIdGS om med hjälp av en propelleromrörare i 15 minuter och tilläts vila över natten innan testning.Example 6 - 100 g of a dispersion of a styrene-acrylate copolymer, Finndisp A10 (Forcit), with a solids polymer content of 50% by weight and an MFFT of 18 ° C was mixed with 1.00 g of tripropionin to obtain a mixture containing 2% coalescing agent. The mixture was recharged using a propeller stirrer for 15 minutes and allowed to stand overnight before testing.
MFFT uppmättes till 9°C.MFFT was measured at 9 ° C.
Exempel 7 Förfarandet enligt exempel 6 upprepades förutom att mängden tripropionin som tillsattes var 2,50g (5%). MF F T uppmättes till l°C.Example 7 The procedure of Example 6 was repeated except that the amount of tripropionin added was 2.50 g (5%). MF F T was measured at 1 ° C.
Exempel 8 Förfarandet enligt exempel 6 och 7 upprepades förutom att det kommersiella koaliseringsmedlet NX795 tillsattes istället för tripropioriin. MFF T uppmättes till 8°C respektive 0°C.Example 8 The procedure of Examples 6 and 7 was repeated except that the commercial coalescing agent NX795 was added instead of tripropioriine. MFF T was measured at 8 ° C and 0 ° C, respectively.
Exempel 9 100g av en dispersion av en styren-akrylat sampolymer, Pliotec 7104E (Eliokem), med ett innehåll av fast polymerrnaterial på 45 vilct-% och en MFFT på 60°C blandades med 4,50g tripropionin for att få en blandning innehållande 10% koaliseringsmedel. Blandningen rördes om med hjälp av en propelleronirörare i 15 minuter och tilläts vila över natten innan testning.Example 9 100 g of a dispersion of a styrene-acrylate copolymer, Pliotec 7104E (Eliokem), with a solids polymer content of 45% by weight and an MFFT of 60 ° C were mixed with 4.50 g of tripropionin to obtain a mixture containing % coalescing agent. The mixture was stirred using a propellerone stirrer for 15 minutes and allowed to stand overnight before testing.
MFFT uppmättes till 3 l°C.MFFT was measured at 3 l ° C.
Exempel 10 g Förfarandet enligt exempel 9 upprepades förutom att mängden tripropionin som tillsattes var 6,75g (15%). MFFT uppmättes till 12°C. 530 420 Exempel 11 Förfarandet enligt exempel 9 upprepades förutom att mängden tripropionin som tillsattes var 9,0g (20%). MF FT uppmättes till 0°C.Example 10 g The procedure of Example 9 was repeated except that the amount of tripropionin added was 6.75 g (15%). MFFT was measured at 12 ° C. 530 420 Example 11 The procedure of Example 9 was repeated except that the amount of tripropionin added was 9.0 g (20%). MF FT was measured at 0 ° C.
Exempel 12 Förfarandet enligt exempel 9, 10 och ll upprepades förutom att tributyrin i stället för tripropionin tillsattes dispersionen av en styren-akrylat sampolymer, MFF T uppmättcS till 24°C, 12°C respektive 0°C.Example 12 The procedure of Examples 9, 10 and 11 was repeated except that tributyrin instead of tripropionine was added to the dispersion of a styrene-acrylate copolymer, MFF T measured at 24 ° C, 12 ° C and 0 ° C, respectively.
Exempel 13 Förfarandet enligt exempel 9, 10 och ll upprepades förutom att det kommersiella koaliseringsmedlet NX7 95 tillsattes istället för tripropionin. MFFT uppmättes till 3 l°C, l7°C respektive 7°C.Example 13 The procedure of Examples 9, 10 and 11 was repeated except that the commercial coalescing agent NX7 95 was added instead of tripropionin. MFFT was measured at 31 ° C, 17 ° C and 7 ° C, respectively.
Exempel 14 1()Og av en dispersion av en vinylacetate-/vinyl- versatat sampolymer, Rhodopas AV-439 (Rhodia Iberlatex), med ett innehåll av fast polymermaterial på 55 vikt-% och en MFFT på 14°C blandades med l,l0g tripropionin för att få en blandning innehållande 2% koaliseringsmedel. Blandningen rördes om med hjälp av en propelleromrörare i 15 minuter och tilläts vila över natten innan testning. MFFT uppmättes till 9°C.Example 14 1 () Og of a dispersion of a vinyl acetate / vinyl versatate copolymer, Rhodopas AV-439 (Rhodia Iberlatex), having a solids polymer content of 55% by weight and an MFFT of 14 ° C was mixed with 1, 10g tripropionin to obtain a mixture containing 2% coalescing agent. The mixture was stirred using a propeller stirrer for 15 minutes and allowed to stand overnight before testing. MFFT was measured at 9 ° C.
Exempel 15 Förfarandet enligt exempel l4 upprepades förutom att mängden tripropionin som tillsattes var 2,75g (5%). MFFT uppmättes till 3°C.Example 15 The procedure of Example 14 was repeated except that the amount of tripropionin added was 2.75 g (5%). MFFT was measured at 3 ° C.
Exempel 16 F örfarandet enligt exempel 14 och 15 upprepades förutom att det kommersiella koaliseringsmedlet NX795 tillsattes istället för tripropionin. MFFT uppmättes till 7°C respektive 4°C.Example 16 The procedure of Examples 14 and 15 was repeated except that the commercial coalescing agent NX795 was added instead of tripropionin. MFFT was measured at 7 ° C and 4 ° C, respectively.
Exempel 17 l00g av en dispersion av en styren-akrylat sampolymer, Acronal 290 D (BASF), med ett innehåll av fast polymennaterial på 50 vikt-% och en MFF T på 20°C blandades med 1,00g tripropionin för att få en blandning innehållande 2% koaliseringsmedel. Blandningen rördes 530 420 om med hjälp av en propelleromrörare i 15 minuter och tilläts vila över natten innan testning.Example 17 100 g of a dispersion of a styrene-acrylate copolymer, Acronal 290 D (BASF), having a solids polymer content of 50% by weight and an MFF T of 20 ° C were mixed with 1.00 g of tripropionin to obtain a mixture containing 2% coalescing agent. The mixture was stirred with a propeller stirrer for 15 minutes and allowed to stand overnight before testing.
MFFT uppmättes till 13°C.MFFT was measured at 13 ° C.
Exempel 18 Förfarandet enligt exempel 17 upprepades förutom att mängden tripropionin som tillsattes var 2,sog (m). MFFT uppmanas :in 3°C.Example 18 The procedure of Example 17 was repeated except that the amount of tripropionin added was 2 suction (m). MFFT is requested: in 3 ° C.
Exempel 19 Förfarandet enligt exempel 17 och 18 upprepades .förutom att tributyrin i stället för tripropionin tillsattes dispersionen av styren-akrylat sampolymeren. MFFT uppmätteS 'till l0°C respektive 4°C.Example 19 The procedure of Examples 17 and 18 was repeated except that tributyrin was added to the dispersion of the styrene-acrylate copolymer instead of tripropionin. MFFT measured S 'at 10 ° C and 4 ° C, respectively.
Exempel 20 Förfarandet enligt exempel 17 och 18 upprepades förutom att det kommersiella koaliseringsmedlet NX795 tillsattes istället för tripropionin. MFFT uppmättes till 13°C respektive 5°C.Example 20 The procedure of Examples 17 and 18 was repeated except that the commercial coalescing agent NX795 was added instead of tripropionin. MFFT was measured at 13 ° C and 5 ° C, respectively.
Exempel 21 En glansig vit färg framställdes på konventionellt sätt för att testa tripropionins funktion som koaliseringsmedel i en färgformulering. Först blandades 37.23 viktdelar vatten, 36.74 viktdelar propylenglykol, 5.11 viktdelar av ett pigmentvätningsmedel, Orotan 1124 (Rohm & Haas) och 3.77 viktdelar av en skumdämpare, Byk 024 (Byk Chemie) i ett cylindriskt malningskärl, utrustat med en sönderdelare (kraftfull mekanisk omrörare utrustad med ett typiskt räfflat blandningsblad). Sönderdelaren startades och 253.65 viktdelar av pigmentet, Ti- Pure R900 (DuPont) tillsattes gradvis med sådan hastighet att tillsatserna kontinuerligt inblandades. När allt pigment var tillsatt, kördes sönderdelaren i hög hastighet i ungefär 15 minuter. Blandningshastigheten sänktes sedan och 620.44 viktdelar av en dispersion av en styren-akrylat sampolymer, Pliotec 7104E (Eliokem) tillsattes gradvis, varpå först 39.78 viktdelar av ett förtjockningsmedel, Acrysol R-2020 (Rohm & Haas) och sedan 3.28 viktdelar ammoniak tillsattes. Färgen blandades slutligen med en måttlig omrörningshastighet i 30 minuter för att försäkra total homogenisering.Example 21 A glossy white color was prepared in a conventional manner to test the function of tripropionin as a coalescing agent in a color formulation. First, 37.23 parts by weight of water, 36.74 parts by weight of propylene glycol, 5.11 parts by weight of a pigment wetting agent, Orotan 1124 (Rohm & Haas) and 3.77 parts by weight of a defoamer, Byk 024 (Byk Chemie) were mixed in a cylindrical grinding vessel equipped with a shredder (powerful mechanical stirrer). with a typical rake mixture blade). The disintegrator was started and 253.65 parts by weight of the pigment, Ti-Pure R900 (DuPont) was added gradually at such a rate that the additives were continuously mixed. When all the pigment was added, the decomposer was run at high speed for about 15 minutes. The mixing speed was then lowered and 620.44 parts by weight of a dispersion of a styrene-acrylate copolymer, Pliotec 7104E (Eliokem) was added gradually, then first 39.78 parts by weight of a thickener, Acrysol R-2020 (Rohm & Haas) and then 3.28 parts by weight of ammonia were added. The paint was finally mixed at a moderate stirring speed for 30 minutes to ensure total homogenization.
Koaliseringsmedlet som skulle testas blandades sedan in i fargblandningen, varpå mängden vatten justerades för att få ett innehåll av fast material på 46 vikt-%. För att få 10% 530 420 i 8 koaliseringsmedel av det fasta polymennaterialet tillsattes 2,58g tripropionin 0011 6,12% Vatten till fárgblandningen. 100 g prov av fargblandningen användes sedan för att testa koaliseringshjälpmedelseffekten.The coalescing agent to be tested was then mixed into the dye mixture, after which the amount of water was adjusted to obtain a solids content of 46% by weight. To obtain 10% 530,420 in 8 coalescing agents of the solid polymer material, 2.58 g of tripropionin 0011 6.12% Water was added to the dye mixture. 100 g of sample of the dye mixture was then used to test the coalescing aid effect.
MFFT uppmättes till 24°C.MFFT was measured at 24 ° C.
Exempel 22 Förfarandet enligt exempel 21 upprepades förutom att mängden tripropionin 0611 Vatten SOm tillsattes fargblandningen var 3,87g respektive 4,83g föratt få 15% koaliseringsmedel av det fasta polymermaterialet. Filmens hårdhet mättes med Koenig hårdhetstest, ett test baserat på en oscillerande pendel där energin absorberas av filmens elasticitet. Koenig hårdheten' bestäms genom den tid i sekunder det tar att minska pendelns oscillering. Högre Värde På Koenig hårdheten indikerar en hårdare yta. Hårdhetsresultaten visas i figur 1. MFFT uppmättes till 12°C.Example 22 The procedure of Example 21 was repeated except that the amount of tripropionine was added to the dye mixture was 3.87 g and 4.83 g, respectively, to obtain 15% coalescing agent of the solid polymeric material. The hardness of the film was measured with the Koenig hardness test, a test based on an oscillating pendulum where the energy is absorbed by the elasticity of the film. Koenig hardness' is determined by the time in seconds it takes to reduce the oscillation of the pendulum. Higher Value On Koenig hardness indicates a harder surface. The hardness results are shown in Figure 1. MFFT was measured at 12 ° C.
Exempel 23 Förfarandet enligt exempel 21 upprepades förutom att mängden tripropionin och vatten som I tillsattes fárgblandningen var 5,16g respektive 3,54g för att få 20% koaliseringsmedel av det fasta polymerrnaterialet. MFFT uppmättes till l°C.Example 23 The procedure of Example 21 was repeated except that the amount of tripropionin and water added to the dye mixture was 5.16 g and 3.54 g, respectively, to obtain 20% coalescing agent of the solid polymeric material. MFFT was measured at 1 ° C.
Exempel 24 Förfarandet enligt exempel 21, 22, 23 upprepades förutom att det kommersiella koaliseringsmedlet NX795 tillsattes istället för tripropionin. Filmens Koenig hårdhet uppmâttes för fargblandningen med 15% koaliseringsmedel, hårdhetsresultaten visas i figur 1.Example 24 The procedure of Examples 21, 22, 23 was repeated except that the commercial coalescing agent NX795 was added instead of tripropionin. The Koenig hardness of the film was measured for the dye mixture with 15% coalescing agent, the hardness results are shown in Figure 1.
MF FT uppmättes till 30°C, 16°C respektive 8°C.MF FT was measured at 30 ° C, 16 ° C and 8 ° C, respectively.
Enligt resultaten av Koenig hårdhetstest, figur 1, är hårdheten på fárgfilmema i exempel 22 och 24 ungefär lika. Testet utfördes vid 23(+-l) °C och 50(+-5) % rßläïíV fuktighet (RH)-According to the results of the Koenig hardness test, Figure 1, the hardness of the dyes in Examples 22 and 24 is approximately equal. The test was performed at 23 (+ - 1) ° C and 50 (+ - 5)% residual moisture (RH) -
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| PCT/SE2007/000541 WO2008054277A1 (en) | 2006-09-18 | 2007-06-05 | A waterborne binder composition and use thereof |
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| US8444758B2 (en) | 2006-10-19 | 2013-05-21 | Eastman Chemical Company | Low voc additives for extending the wet edge and open time of aqueous coatings |
| US20100240817A1 (en) * | 2009-03-18 | 2010-09-23 | Genovique Specialties Holdings Corporation | Aqueous Polymer Compositions Containing Glycerol Esters As Plasticizers |
| US8022127B2 (en) | 2009-03-24 | 2011-09-20 | Eastman Specialties Holdings Corporation | Plastisols containing glycerol esters as plasticizers |
| EP2284238B1 (en) * | 2009-08-14 | 2013-07-03 | Henkel AG & Co. KGaA | Waterborne adhesive with improved wet adhesion |
| WO2014064020A1 (en) | 2012-10-24 | 2014-05-01 | Akzo Nobel Chemicals International B.V. | Water-redispersible polymer powder comprising a triester |
| MX2018012082A (en) | 2016-04-07 | 2019-03-28 | Ascend Performance Mat Operations Llc | Tri-carboxylic compounds as low-voc coalescing agents and plasticizing agents. |
| WO2022132820A2 (en) * | 2020-12-14 | 2022-06-23 | Battelle Memorial Institute | Bio-based coalescing solvents |
| WO2022132812A1 (en) * | 2020-12-14 | 2022-06-23 | Battelle Memorial Institute | Soybean-based coalescing solvents |
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| GB567879A (en) * | 1943-02-01 | 1945-03-07 | Du Pont | Improvements in or relating to the stabilisation of vinyl esters |
| GB567464A (en) * | 1943-05-14 | 1945-02-15 | Ici Ltd | Stabilisation of vinyl esters |
| FR1155903A (en) * | 1955-06-29 | 1958-05-09 | Eastman Kodak Co | Process for the preparation of mixed triglyceride compositions, products obtained and their applications |
| US3074912A (en) * | 1960-08-12 | 1963-01-22 | Air Reduction | Stabilization of vinyl acetate |
| CH457835A (en) * | 1964-02-27 | 1968-06-15 | Du Pont | Stable aqueous dispersion suitable for coating purposes |
| US3524828A (en) * | 1964-03-31 | 1970-08-18 | Borden Inc | Composition for adhering plastic film to a vapor penetrable non-metallic substrate |
| US3522070A (en) * | 1965-01-21 | 1970-07-28 | Du Pont | Aqueous coating compositions containing dispersed submicron cellulosic polymer particles and the process of preparing said coating compositions |
| US3409623A (en) * | 1965-03-05 | 1968-11-05 | Acf Ind Inc | Chlorinated oxetane polymer coating composition |
| NL127901C (en) * | 1966-02-10 | |||
| US3451883A (en) * | 1966-08-09 | 1969-06-24 | Hercules Inc | Method for shaping a material impregnated with a nitrocellulose-plasticizer hydrosol and the resulting shaped article |
| GB1250614A (en) * | 1968-03-29 | 1971-10-20 | ||
| US3668158A (en) * | 1970-06-03 | 1972-06-06 | Borden Inc | Composition for adhering plastic film to a vapor penetrable non-metallic substrate |
| DE3855956T2 (en) * | 1987-01-13 | 1997-11-06 | Kao Corp | Use of a triglyceride compound as a hemolysis inhibitor |
| EP0533641A3 (en) * | 1991-08-19 | 1993-06-16 | Novis W. Smith Jr. | Coating composition for parts |
| DE4324474A1 (en) * | 1993-07-21 | 1995-01-26 | Henkel Kgaa | Use of selected polyvinyl acetate dispersions for the surface consolidation of sand and / or soil |
| US5445754A (en) * | 1994-03-28 | 1995-08-29 | P.S.A.M.S., Inc. | Water-based, thermal paint |
| US5416140A (en) * | 1994-06-10 | 1995-05-16 | Borden, Inc. | Cross-linkable thixotropic wood adhesive gel |
| CN1216774A (en) * | 1998-06-22 | 1999-05-19 | 李勇军 | Water-proof emulsion for roof |
| EP1313466A4 (en) * | 2000-08-02 | 2005-11-23 | Atossa Healthcare Inc | Bimodal emulsions of taxanes and butyrate polyalcohol esters |
| EP1413624B1 (en) * | 2002-10-22 | 2006-03-08 | Rohm and Haas Company | Tablet coating |
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