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(12) Patent Application Publication (10) Pub. No.: US 2016/0251798 A1 Van Rossum Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0251798 A1 Van Rossum Et Al US 2016025 1798A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0251798 A1 Van ROSSum et al. (43) Pub. Date: Sep. 1, 2016 (54) BONDINGAGENTS FOR PLASTSOLS Publication Classification CONTAINING DOTP OR DINCH (51) Int. Cl. (71) Applicant: Eastman Chemical Company, D6N3/00 (2006.01) Kingsport, TN (US) D6N3/06 (2006.01) (52) U.S. Cl. (72) Inventors: Ruud van Rossum, Vrouwenpolder CPC ................ D06N3/0059 (2013.01): D06N3/06 (NL); Cornelis Johannes Gerardus (2013.01): D06.N3/0077 (2013.01): D06N Maria Hermans, Heinkenszand (NL); 2203/048 (2013.01): D06N2201/02 (2013.01); Daniel Henry Bolton, Kingsport, TN D06N2201/0263 (2013.01) (US) (73) Assignee: Eastman Chemical Company, (57) ABSTRACT Kingsport, TN (US) A bonding composition for adhering PVC to fabric is dis (21) Appl. No.: 14/632,528 closed. The bonding composition contains isocyanurate and organophosphate at an organophosphate to isocyanurate (22) Filed: Feb. 26, 2015 weight ratio of 4:1 to 10:1. Patent Application Publication Sep. 1, 2016 Sheet 1 of 2 US 2016/025 1798 A1 Patent Application Publication Sep. 1, 2016 Sheet 2 of 2 US 2016/025 1798 A1 ::::::::::: US 2016/025 1798 A1 Sep. 1, 2016 BONDINGAGENTS FOR PLASTSOLS fabric. The composition comprises (a) isocyanurate and (b) CONTAINING DOTP OR DINCH organophosphate at an organophosphate to isocyanurate weight ratio of 4:1 to 10:1. FIELD OF THE INVENTION 0013. In another aspect, the present invention provides a coating composition. The coating composition comprises: 0001. The invention generally relates to compositions for 0014 (a) a plastisol comprising polyvinyl chloride pow bonding flexible PVC to synthetic fabric and to their use. der dispersed in a plasticizer comprising dioctyl terephthalate or 1.2-cyclohexane dicarboxylic acid diisononyl ester; and BACKGROUND OF THE INVENTION 00.15 (b) the bonding composition according to the inven 0002 There are many applications for polyvinyl chloride tion. (PVC) coated fabrics. These include tarpaulins, conveyor 0016. In yet another aspect, the present invention provides belts, geomembranes, marquees, roofing and cladding mate a process for coating a fabric. The process comprises: rials, protective clothing, floor coverings, and many others. 0017 (a) combining the bonding composition according Historically, natural fabrics were used in these applications, to the invention with a plastisol comprising polyvinyl chlo but the natural fabrics have now been substituted, in many ride powder dispersed in a plasticizer comprising dioctyl instances, with synthetic fibers. Compared to natural fibers, terephthalate or 1.2-cyclohexane dicarboxylic acid synthetic fibers have been found to offer improved strength, disononyl ester, and toughness, lightness, moisture resistance, resistance to 0018 (b) coating at least one side of a fabric with the microorganisms, and flexibility. mixture from step (a). 0003) Synthetic fibers, however, generally have smooth 0019. The present invention also provides for articles of monofilaments. PVC coatings tend to have poor mechanical manufacture comprising a fabric coated with the coating adhesion to Smooth Surfaces. To improve adhesion, a specific composition according to the invention. bonding agent can be added to the PVC coating Solution (often a plastisol) just prior to application. The bonding agent BRIEF DESCRIPTION OF THE DRAWINGS chemically bonds with the reactive groups of the fabric and 0020 FIG. 1 is a bar graph of the peel strength of various allows the PVC coating to adhere to the fabric. PVC formulations based on DINP plasticizer from Example 0004 Most bonding agents incorporate isocyanates. A 3. class of isocyanates is called isocyanurate. 0021 FIG. 2 is a bar graph of the peel strength of various 0005. It is common to incorporate into the bonding com PVC formulations based on DOTP plasticizer from Example position an ortho-phthalate carrier, for instance, dibutyl 4. phthalate, dioctyl phthalate, or diisononyl phthalate (DINP). However, even though using ortho-phthalate carriers is com DETAILED DESCRIPTION OF THE INVENTION mon, such use is often undesirable due to public opinion on 0022. It has been found, Surprisingly, that organophos the adverse health effect of phthalates. phates can improve the compatibility of bonding agents con 0006 Recently, there has been a movement away from taining isocyanurates with plastisols containing non-ortho using ortho-phthalate plasticizers. phthalate plasticizers. 0007 Alternatives to ortho-phthalate plasticizers include 0023 Thus, in one aspect, the present invention provides a dioctyl terephthalate (DOTP) (also known as diethylhexyl bonding composition for adhering polyvinyl chloride to fab terephthalate (DENT)), 1.2-cyclohexane dicarboxylic acid ric. The composition comprises: disononyl ester (DINCH), hydrogenated dioctyl phthalate 0024 (a) isocyanurate; and (DHEH), hydrogenated DOTP (DOCH), citrates, Mesa 0025 (b) organophosphate, mollR (alkylsulfonic acid ester with phenol), butyloctyl 0026 wherein the weight ratio of organophosphate to iso terephthalate (BOTP), and isononylbenzoate (INB). cyanurate ranges from 4:1 to 10:1. 0008. However, commercially available bonding agents 0027. The isocyanurate preferably comprises aromatic can show poor compatibility with ortho-phthalate free plas diisocyanate groups, such as 2,4-diisocyanatotoluene, 2.6- tisols. Poor compatibility can result in a very short pot life due diisocyanatotoluene, or mixtures thereof. In one embodi to rapidly increasing plastisol viscosity and gelation of the ment, the isocyanurate comprises 2,4-toluene diisocyanate plastisol shortly after adding the bonding agent. trimer (CAS #26603-7). 0009. Thus, there is a need for a bonding agent that shows 0028 Bonding agents containing isocyanurate are com good compatibility with ortho-phthalate free PVC plastisols. mercially available. Alternatively, the isocyanurate may be There is also a need for a bonding agent that, in addition to prepared by methods using catalysts known in the art. For showing good compatibility with ortho-phthalate free PVC example, isocyanurates can be produced by oligomerization, plastisols, can improve the adherence of the PVC to fabric, in particular trimerization, from diisocyanates. The diisocy especially synthetic fabric. anates normally used for this purpose include the isomeric 0010. The present invention addresses these needs as well diisocyanatotoluenes (TDI), composed mainly of 2,4-diiso as others, which will become apparent from the following cyanatotoluene (2,4-TDI) and 2,6-diisocyanatotoluene (2,6- description and the appended claims. TDI). These can easily be converted almost completely to isocyanurates. The isocyanurate may also be produced exclu SUMMARY OF THE INVENTION sively from 2,4-TDI. 0029. The isocyanurate may be prepared by treating the 0011 The invention is as set forth in the appended claims. toluene diisocyanate, either alone or in a suitable solvent, 0012 Briefly, in one aspect, the present invention provides with a basic catalyst Such as an aliphatic tertiary amine, a a bonding composition for adhering polyvinyl chloride to basic metallic compound Such as an alkali or alkaline earth US 2016/025 1798 A1 Sep. 1, 2016 metal oxide, hydroxide carbonate, alcoholate or phenate, an carbon atoms. Specific examples of Suitable organophos alkali metal salt of an enolizable compound or a metallic salt phates include tri-ethylhexyl phosphate, tricresyl phosphate, of a weak organic carboxylic acid. Co-catalysts may be used, isodecyl diphenyl phosphate, 2-ethylhexyl diphenyl phos Such as, for example, mono-N-Substituted carbamic esters in phate, or mixtures thereof. In one embodiment, the organo conjunction with basic metallic compounds. Catalysts con phosphate comprises tri-ethylhexyl phosphate. taining metallic salts of weak organic carboxylic acids, 0035. The amount of organophosphate in the bonding optionally in the presence of a mono-N-Substituted carbamic composition may range from 50 to 99.5% by weight, based on ester, can considerably reduce polymerization times. the total weight of the bonding composition. Other amounts 0030) Suitable solvents for preparing the isocyanurate of the organophosphate are possible. Such as from 75 to include Solvents that are inert towards isocyanates, and 99.5% by weight, 80 to 99.5% by weight, 85 to 99.5% by include, for example, esters such as ethyl acetate, butyl weight, 50 to 95% by weight, 75 to 95% by weight, 80 to 95% acetate, amyl acetate, diethyl phthalate, the acetate of the by weight, 85 to 95% by weight, 50 to 92% by weight, 75 to monoethyl ether of ethylene glycol, dimethyl phthalate, and 92% by weight, 80 to 92% by weight, 85 to 92% by weight, 50 butylbenzoate: ketones such as methyl isobutyl ketone; chlo to 90% by weight, 75 to 90% by weight, 80 to 90% by weight, roform; benzene: toluene; xylene; sulfur dioxide; butyrolac or 85 to 90% by weight. tone; monochlorobenzene; o-dichlorobenzene; ethers; or 0036. The weight ratio of organophosphate to isocyanu mixtures of Such solvents. rate in the bonding composition ranges from 4:1 to 10:1. In 0031. The preparation of isocyanurate may conveniently one embodiment, the weight ratio of organophosphate to be carried out by polymerizing the toluene diisocyanate with isocyanurate ranges from 4.5:1 to 10:1. In yet other embodi a suitable catalyst until the desired polymer has been ments, the weight ratio of organophosphate to isocyanurate obtained; further polymerization may then be prevented, for ranges from 5:1 to 10:1,
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