Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment V. Bojinov*, T. Konstantinova University of Chemical Technology and Metallurgy, Department of Organic Synthesis, 8 Kl. Ohridsky str., BG-1756 Sofia, Bulgaria Received 15 March 2002; received in revised form 19 April 2002; accepted 16 May 2002 Abstract The synthesis of new 1,8-naphthalimide dyes, containing hindered amine stabilizer fragment is reported. Two poly- merizable dyes, a combination between 1,8-naphthalimide and 2,2,6,6-tetramethylpiperidine, as well as three 1,8- naphthalimideintermediatesweresynthesizedingoodyieldsundervariablereactionconditions.Theabilityofthedyes for co-polymerization with vinyl monomers such as acrylonitrile was demonstrated. # 2002 Elsevier Science Ltd. All rights reserved. Keywords: Polymerizable fluorescent dyes containing stabilizer; 1,8-Naphthalimide; 4-Amino-2,2,6,6-tetramethylpiperidine; Co-polymerization 1. Introduction The chemical colouration of polymers repre- sents the possibility of obtaining polymers with a colour stable to solvents. In our earlier papers we synthesized different monomeric dyes and demon- stratedthepossibilityinherentlycolouredpolymers to be obtained [1–4]. On the other hand photo stability of polymers is of grate importance for theiruse[5].Thecovalentbondingofthestabilizer to the polymer chain provided a good stability to solvents and migration, improving their environ- mentalbehaviour,whichisofimportanceespecially for those applied to food and cosmetics [6]. We have reported before on the synthesis of different polymerizablestabilizersandtheirco-polymerization withstyreneandmethylmethacrylate[7–9].Inour earlier paper [10] we demonstrated the possibility for ‘‘one-step’’ colouration and stabilization of polystyrene using an unsaturated 1,3,5-triazine derivative, where a benzanthrone dye and a stabi- lizerwerecombinedinonemolecule. Derivatives of 1,8-naphthalimide are well known as dyes for mass colouration of polymers, markers in biomaterials and so on [11–14]. We synthesized before some unsaturated 1,8-naph- thalimide dyes capable to co-polymerize with dif- ferent monomers [3,15–19]. Bearing in mind these investigationsitwasofinteresttosynthesizesome new naphthalimide derivatives, where a polymer- izablegroupandastabilizertobecombinedinthe dye molecule. The molecule of 1,8-naphthalimide representsagoodpossibilityforsuchcombination. Thus,thiswastheobjectofthepresentstudy. 0143-7208/02/$ - see front matter # 2002 Elsevier Science Ltd. All rights reserved. PII:S0143-7208(02)00047-5 Dyes and Pigments 54 (2002) 239–245 www.elsevier.com/locate/dyepig * Correspondingauthor.Tel.:+359-2-6254-359;fax:+359- 291-76606. E-mail address: vlbojin@uctm.edu (V. Bojinov).