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HONG KONG — Google’s problems in China just got worse.

As part of a broad campaign to tighten internal security, the Chinese government has draped a darker shroud over Internet communications in recent weeks, a situation that has made it more difficult for Google and its customers to do business.

Chinese exporters have struggled to place Google ads that appeal to overseas buyers. Biotechnology researchers in Beijing had trouble recalibrating a costly microscope this summer because they could not locate the online instructions to do so. And international companies have had difficulty exchanging Gmail messages among far-flung offices and setting up meetings on applications like Google Calendar.

“It’s a frustrating and annoying drain on productivity,” said Jeffrey Phillips, a U.S. energy executive who has lived in China for 14 years. “You’ve got people spending their time figuring out how to send a file instead of getting their work done.”

The pain is widespread. Two popular messaging services owned by South Korean companies, Line and Kakao Talk, were abruptly blocked this summer, as were other applications like Didi, Talk Box and Vower. U.S. giants like Twitter and Facebook have long been censored by China’s Great Firewall, a system of filters the government has spent lavishly on to control Internet traffic in and out of the country.

Alibaba, with its splashy New York IPO last week, dominates the market in China, along with Baidu, the Google of China, and Tencent, China’s top social-networking messaging service. The question becomes how much of China’s parade of restrictions and blockages is responsible for their success?

Even as Google and other big technology companies have lobbied heavily for an easing of the restrictions, Beijing’s broader scrutiny of multinationals has intensified. In late July, anti-monopoly investigators raided Microsoft offices in four Chinese cities to interrogate managers and copy large amounts of data from hard drives. Qualcomm, a big maker of computer chips and a holder of wireless technology patents, faces a separate anti-monopoly investigation.

The increasingly pervasive blocking of the Web, together with other problems like severe air pollution in China’s urban centers, has led some businesses to transfer employees to regional hubs with more open and speedier Internets, like Singapore. And more companies are considering similar moves.

“Companies overlooked Internet problems when the economy was booming,” said Shaun Rein, managing director of the China Market Research Group, a Shanghai consulting firm. “But now a lot of companies are asking whether they really need to be in China.”

As Alibaba’s initial public offering of stock in New York on Thursday demonstrated, China has produced many highly successful Web businesses. But many executives and researchers say that a number of homegrown Internet services are poor substitutes for the multinationals’ offerings.

Google’s troubles in China have been building up for years.

The company shut down its servers in mainland China in March 2010 to avoid online censorship and began directing users in China to obtain unfiltered results from its servers in Hong Kong. The Chinese government then began intermittently blocking the Hong Kong servers as well, notably by halting the ability to reach the site for up to 90 seconds if a user tried to enter anything on a very long list of banned Chinese characters, including those in national leaders’ names, and some English words.

Google began encrypting users’ searches and results all over the world early this year, partly in response to former National Security Agency contractor Edward J. Snowden’s disclosures about U.S. government surveillance. That shift by Google — using Internet addresses that start with “https” — made it harder for Chinese censors to determine who was pursuing the types of inquiries that they discourage.

But the Chinese government responded May 29 by blocking virtually all access to Google websites, instead of just imposing 90-second delays when banned search terms were used.

Experts initially interpreted the move as a security precaution ahead of the 25th anniversary of the Tiananmen Square crackdown on June 4. But the block has largely remained in place ever since.

In the meantime, Google’s business continues to erode. Its share of the Chinese search-engine market fell to 10.9 percent in the second quarter of this year, as the stepped-up blocking began to take effect — compared with one-third in 2009, when it still had servers there.

Google also hosts publicly available libraries of coding scripts and fonts on its servers, but China now blocks these libraries.

The chief technology officer at the startup said his company had resorted to creating its own libraries and hosting them on its own servers, wasting costly computing power and space.

“We have our own closed server in the office and host things there,” he said. “That’s not going to the cloud; it’s like going back to the early 2000s.”