Unfortunately we don't support conditional comments for the time being. However this sounds like a very nice feature and I have logged it in our TODO list.
In case anyone else needs this functionality, here's how we implemented this using the following syntax:
Html.Telerik().StyleSheetRegistrar()
.DefaultGroup(group => group.Add("Site-ie6.css")
.Add("Page-ie6.css")
.Combined(true)
.ConditionalComment("if IE 6")
)
We extended IWebAssetItemMerger with a new method MergeWithConditionalComments which returns a dictionary<string,string> containing the stylesheet and conditional commment.
Finally, updated StyleSheetRegistrar with:
if (!mergedList.IsEmpty())
{
foreach (KeyValuePair<string,string> keyValue in mergedList)