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WO 2017/137734 Al 17 August 2017 (17.08.2017) P O P C T

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WO 2017/137734 Al 17 August 2017 (17.08.2017) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/137734 Al 17 August 2017 (17.08.2017) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C09D 5/02 (2006.01) C08K 5/11 (2006.01) kind of national protection available): AE, AG, AL, AM, C09D 7/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, (21) Number: International Application DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/GB20 17/050302 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, (22) International Filing Date: KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, 8 February 2017 (08.02.2017) MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, (25) Filing Language: English RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, (26) Publication Language: English TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 1602 188.3 8 February 2016 (08.02.2016) GB (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: CHEMOXY INTERNATIONAL LIMITED GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, [GB/GB]; All Saints Refinery, Cargo Fleet Road, Middles TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, brough TS3 6AF (GB). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: STARK, Ian; c/o Chemoxy International Lim LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, ited, All Saints Refinery, Cargo Fleet Road, Middles SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, brough TS3 6AF (GB). TARBIT, Brian; c/o Chemoxy In GW, KM, ML, MR, NE, SN, TD, TG). ternational Limited, All Saints Refinery, Cargo Fleet Road, Middlesbrough TS3 6AF (GB). MITFORD, Rick; c/o Declarations under Rule 4.17 : Chemoxy International Limited, All Saints Refinery, Cargo — of inventorship (Rule 4.17(iv)) Fleet Road, Middlesbrough TS3 6AF (GB). STEPHEN¬ SON, Gavin; c/o Chemoxy International Limited, All Published: Saints Refinery, Cargo Fleet Road, Middlesbrough TS3 — with international search report (Art. 21(3)) 6AF (GB). (74) Agents: HGF LIMITED et al; 1 City Walk, Leeds, West Yorkshire LSI 1 9DX (GB). (54) Title: COALESCENTS (57) Abstract: This invention relates to the use of compounds derived from malic acid and other diacids as coalescents, e.g. in water based decorative latex paints. Coalescents [0001] This invention relates to the use of compounds derived from malic acid and other substituted diacids as coalescents, e.g. in water based decorative latex paints. BACKGROUND [0002] Coalescents are compounds which promote the formation of a uniform film upon application of a latex to a surface. When a latex containing a coalescent is deposited onto a surface, the coalescent softens the polymer particles in order to allow them to fuse (or coalesce) with each other. This contributes to their inter diffusion and increases the uniformity of the film. As the carrier solvent begins to evaporate, the volume of the wet coating layer begins to be reduced and the polymer particles begin to touch and loose shape. As the process goes on, agglomeration and inter-diffusion occurs and the dispersion inverts itself in the sense that the bulk of the film is a solid in which a minor component is now the original dispersion liquid, i.e. carrier solvent. The film forms and the coalescent slowly evaporates leaving a dry, hard polymer film. [0003] Many market leading coalescents are based on ethylene and propylene glycol ethers (e.g. dipropylene glycol n-butyl ether and ethylene glycol monophenyl ether;). These coalescents tend to release odour and volatile organic chemicals (VOCs), however regulatory legislation is driving a need for coalescents which release less odour and fewer VOCs. [0004] Other coalescents which are currently available, such as 2,2,3-trimethyM ,3- pentanediol monoisobutyrate () and 2,2,3-trimethyl-1,3-pentanediol diisobutyrate (), are not themselves odour free and can react to produce odourous by-products when applied to a surface in a latex. [0005] Certain compounds used in the methods of the invention are derived from malic acid, a readily available starting material. Other substituted diacids, e.g. 2-methylglutaratic acid are likewise readily available. [0006] A good coalescent generally interacts well with both the surface and the inner portions of the polymer particles. They generally also have low water solubility and low volatility. Low volatility may be linked to improved hardness characteristics of the resultant films. In any event, many countries legislation requires coalescents in products to have low volatility and odour. Coalescents generally allow or encourage the paint to undergo phase change at the optimum development stage and should provide a film which is resistant to wet abrasion. Coalescents generally are resistant to hydrolysis at or around neutral pH, thus staying intact during film formation, but are nevertheless fully biodegradable. The compounds of the invention typically exhibit some or all of these properties. [0007] It is an aim of certain embodiments of the invention to provide coalescents which are present in a reduced residual amount in formed films. Conversely, it is an aim of certain embodiments to provide coalescents that can chemically bind to the polymer (possibly reducing VOC emissions). It is an aim of certain embodiments to provide coalescents that.can bind to certain polymer(s), thus improving the properties of the film (e.g. making the film harder). [0008] It is an aim of certain embodiments of the invention to provide coalescents which have low or zero odour. Likewise, it is an aim of certain embodiments of the invention to provide coalescents which have low or zero emissions and/or low or very low toxicity. [0009] It is an aim of certain embodiments of the invention to produce coalescents having a low VOC rating, e.g. one which meets or exceeds one or more national or international standards at 1 January 2016. It is an aim of certain embodiments of the invention to provide coalescents which have a lower VOC rating than other compounds that have equivalent volatility, e.g. because the coalescent cross-links or otherwise chemically binds to the polymer. [0010] It is an aim of certain embodiments of the invention to provide coalescents which exhibit improved coalescent efficacy relative to prior art coalescents. Thus, film forming compositions of the invention may have lower minimum film forming temperatures than prior art compositions. Thus, film forming compositions of the invention may form harder films than prior art compositions. Thus, film forming compositions of the invention may form less tacky films than prior art compositions. The compounds of the invention may exhibit similar or even reduced coalescent efficacy relative to prior art coalescents but offer other benefits, e.g. they are more readily prepared or comply with legislative requirements in certain countries. [001 1] It is an aim of certain embodiments of the invention to provide coalescents which provide an effective coalescent effect when used in lower concentrations than existing products. [001 2] Certain embodiments of the invention satisfy some or all of the above aims. BRIEF SUMMARY OF THE DISCLOSURE [0013] In a first aspect of the invention is provided a film forming composition comprising: a polymer and at least one compound of formula (I), or a salt thereof: (I), 3 wherein R and R are each independently at each occurrence selected from H ,C 1-C25- Ci-C C 2 4 4 4 4 alkyl, 2 -haloalkyl, C2-C25-alkenyl, -C25 alkynyl, (CR R )m-aryl and (CR R )m- cycloalkyl; n is integer selected from 1 and 2 ; 2 X is independently at each occurrence selected from: C -C4 -alkyl and OR ; 2 R is independently at each occurrence selected from: H , C (0 )Ci -C25 -alkyl, C (0 )Ci -C25- 4 4 haloalkyl,C(0)C 2-C25-alkenyl, C(0)C 2-C25-alkynyl, C(0)(CR R )m-aryl, C(0)(CR R )m- 4 Ci-C Ci-C C cycloalkyl; C(0)(CR =CR )-aryl, 25-alkyl, 2 5-haloalkyl, C2-C25-alkenyl and 2-C25- alkynyl;R 4 is independently at each occurrence selected from: H , F , C i-C4-alkyl and CF3; m is an integer independently selected from: 0 , 1, 2 , 3 , 4 and 5 ; wherein each of the aforementioned alkyl, alkenyl, alkynyl, cycloalkyi and aryl (e.g. phenyl) groups, are optionally substituted, where chemically possible, by 1 to 3 substituents which are each independently at each occurrence selected from the group consisting of: oxo, a a a a fluoro, C0 2R , C(0)R , CONR R , Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkenyl, and C 1-C4- a haloalkyl; wherein R is independently at each occurrence selected from C 1- C 4 alkyl; provided that at least one of R1, R2 and R3 is not H . [0014] In an embodiment, , the compound of formula (I) may be a compound of formula (II): wherein R , R2 and R3 are as defined above for formula (I); [0015] Coalescents (i.e. the compounds of formula (I)) used in the compositions of the invention find particular application in latex based paints, which are typically emulsions of polymer in water, but can also be used in inks, varnishes, adhesives, coatings, fillers etc.
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