Police charged protesters who threw stones and bottles at officers and neighbours in Spanish cities in the fourth night of clashes after a rapper was jailed for glorifying terrorism and insulting royalty in his songs.
The nine-month sentence of Pablo Hasel, known for his fiercely anti-establishment raps, has galvanised a debate over freedom of expression in Spain, prompting the government to announce it would make speech laws less restrictive and sparking protests that, at times, turned violent.
Protesters on Friday threw projectiles at police and at neighbours who condemned them for the disturbances. Two banks and businesses were attacked in Barcelona. Police charged protesters in the northern Catalan city of Girona.
Spanish Prime Minister Pedro Sanchez condemned the violence which has marked protests during the past three nights.
"Democracy protects freedom of speech, including the expression of the most awful, absurd thoughts, but democracy never ever protects violence," he told an event, promising to "widen and improve freedom of speech".
During the past three nights police fired tear gas and foam bullets at demonstrators who set fire to rubbish bins and motorcycles and looted stores. There were also clashes in the capital Madrid and other cities.
Officials said three people were arrested in Barcelona on Friday. About 60 people have been arrested across Catalonia, where Barcelona earlier this week. One woman lost an eye during clashes in Barcelona, triggering calls from politicians to investigate police tactics.
Rights group Amnesty International called for legal changes in Spain, saying that anti-terrorism and gagging laws also unfairly limited people's right to demonstrate their disapproval in the streets.