Whats the reaction of glycols with HCL?

[Juan2011]

Hi All,
My customer has send me a sample for ink which they have problem while printing on PP coated paper. They observe some flakes coming out after printing. The try to add emulsifier which they dont get any improvement. They have two samples- one is standard which they dont have any problem and other one has problem. They wants to know the difference between the two sample. I did IR analysis and got OH bands form both the samples. The sample history of standard shows it has ammonia for formulation. The MS analysis shows presence of glycerol or glycols. I want to know weather the OH band is from Glycol or Ammonia. I am trying to add HCL acids to sample and will run an IR and got the same band. What I am trying to check is weather the sample with problem have ammonia or not. How can I get this ? I thought if the ammonia reacts with acid, the OH band will go or at least the intensity will reduce provided the glycols do not react with HCl. Does it make sense. I am not so good in organic chemistry and tried to google out about the reactions of glycol with HCl which I could not get an thing relevant. Can some organic chemistry people give me some light to this puzzle

[HW Mueller]

I would tell my customer to throw the bad ink out.
The OH band in the IR is not a method for analyzing ammonia/ammonium in a sample.
Glycol reaction with HCl depends on HCl concentration, solvent, co-reagents.