Question

I want to create buttons like these:

In modern browsers the effect is created using inset box-shadow and filters.
For IE8 – pseudo-elements are chosen.
For IE7 – I use special tags wrapped in conditional comments.

Demo: (http://jsfiddle.net/8M5Tt/68/)

/**
 * Button w/o images
 */
html {
    font-size: 62.5%;
    }
body {
    font: normal 1em/1em Arial, Tahoma, Verdana, sans-serif;
    }
 
/* layout */
.btn {
    display: inline-block;
    height: 28px;
    border-width: 1px;
    border-style: solid;
    width: 170px;
    box-sizing: content-box;
    overflow: hidden;
    position: relative;
    z-index: 1;
    }
.btn {
    margin: 15px;
    }
.btn.btn_small {
    width: 130px;
    }

/* ie7 */
.lt-ie8 .btn .before,
.lt-ie8 .btn .after {
    position: absolute;
    right: -1px;
    left: -1px;
    display: block;
    height: 3px;
    }
.lt-ie8 .btn .before {
    top: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#80ffffff', endColorstr='#00ffffff',GradientType=0 );
    }
.lt-ie8 .btn .after {
    bottom: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#00ffffff', endColorstr='#80000000',GradientType=0 );
    }
/* /ie7 */

/* ie8 */
.ie8 .btn:before,
.ie8 .btn:after {
    content: ' ';
    z-index: 1;    
    position: absolute;
    right: -1px;
    left: -1px;
    display: block;
    height: 3px;
    }
.ie8 .btn:before {
    top: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#80ffffff', endColorstr='#00ffffff',GradientType=0 );
    }
.ie8 .btn:after {
    bottom: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#00ffffff', endColorstr='#80000000',GradientType=0 );
    }
/* /ie8 */

/* typo */
.btn {
    /* 28 / 14 = 2.57142857 */
    font: bold 14px/2 Arial, Helvetica, Tahoma, sans-serif;
    text-transform: uppercase;
    }
.btn:active {
    line-height: 2.4em;
    }

/* color */
.btn {
    background-color: #00cccc;
    color: #fff;
    border-color: #00a8a8;
    border-radius: 3px;
    cursor: pointer;
    box-shadow:
         1px  1px 4px rgba(255, 255, 255, 0.5) inset,            
        -1px -1px 4px rgba(000, 000, 000, 0.5) inset;
    }
.btn:hover {
    background-color: #00ebeb;
    }
.btn:active {
    box-shadow:
        -1px -1px 4px rgba(255, 255, 255, 0.5) inset,            
         1px  1px 4px rgba(000, 000, 000, 0.5) inset;
    }

/* green */
.btn_green {
    background-color: #009900;
    border-color: #009600;
    }
.btn_green:hover {
    background-color: #00c200;
    }

/* red */
.btn_red {
    background-color: #e00000;
    border-color: #c13d00;
    }
.btn_red:hover {
    background-color: #f00000;
    }

<!--
paulirish.com/2008/conditional-stylesheets-vs-css-hacks-answer-neither/
-->
<!--[if lt IE 7]> 
    <div class="no-js lt-ie9 lt-ie8 lt-ie7" lang="en">
<![endif]-->
<!--[if IE 7]>
    <div class="no-js lt-ie9 lt-ie8 ie7" lang="en">
<![endif]-->
<!--[if IE 8]>
    <div class="no-js lt-ie9 ie8" lang="en">
<![endif]-->
<!--[if gt IE 8]><!-->
    <div class="no-js no-ie" lang="en">
<!--<![endif]-->

<button class="btn btn_green btn_small ">
    Send
    <!--[if IE 7]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn">
    Buy
    <!--[if IE 7]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn btn_green">
    Activate
    <!--[if IE 7]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn btn_red">
    Delete
    <!--[if IE 7]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

</div>

Main Question: Why don’t filters work on pseudo elements in IE8?

---

Update:

I guess that filters do not work on css-generated content, despite the fact that it is not mentioned on this MSDN page.

I solved my problem in IE8 by applying filters to conditional elements like I do for IE7.

Final demo: (http://jsfiddle.net/matmuchrapna/8M5Tt/73/)

/**
 * Button w/o images
 */
html {
    font-size: 62.5%;
    }
body {
    font: normal 1em/1em Arial, Tahoma, Verdana, sans-serif;
    }
 
/* layout */
.btn {
    display: inline-block;
    height: 28px;
    border-width: 1px;
    border-style: solid;
    width: 170px;
    box-sizing: content-box;
    overflow: hidden;
    position: relative;
    z-index: 1;
    }
.btn {
    margin: 15px;
    }
.btn.btn_small {
    width: 130px;
    }

/* ie78 */
.lt-ie9 .btn .before,
.lt-ie9 .btn .after {
    position: absolute;
    right: -1px;
    left: -1px;
    display: block;
    height: 3px;
    }
.lt-ie9 .btn .before {
    top: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#80ffffff', endColorstr='#00ffffff',GradientType=0 );
    }
.lt-ie9 .btn .after {
    bottom: -1px;
    filter: progid:DXImageTransform.Microsoft.gradient( startColorstr='#00ffffff', endColorstr='#80000000',GradientType=0 );
    }
/* /ie78 */

/* typo */
.btn {
    /* 28 / 14 = 2.57142857 */
    font: bold 14px/2 Arial, Helvetica, Tahoma, sans-serif;
    text-transform: uppercase;
    }
.btn:active {
    line-height: 2.4em;
    }

/* color */
.btn {
    background-color: #00cccc;
    color: #fff;
    border-color: #00a8a8;
    border-radius: 3px;
    cursor: pointer;
    box-shadow:
         1px  1px 4px rgba(255, 255, 255, 0.5) inset,            
        -1px -1px 4px rgba(000, 000, 000, 0.5) inset;
    }
.btn:hover {
    background-color: #00ebeb;
    }
.btn:active {
    box-shadow:
        -1px -1px 4px rgba(255, 255, 255, 0.5) inset,            
         1px  1px 4px rgba(000, 000, 000, 0.5) inset;
    }

/* green */
.btn_green {
    background-color: #009900;
    border-color: #009600;
    }
.btn_green:hover {
    background-color: #00c200;
    }

/* red */
.btn_red {
    background-color: #e00000;
    border-color: #c13d00;
    }
.btn_red:hover {
    background-color: #f00000;
    }

<!--
paulirish.com/2008/conditional-stylesheets-vs-css-hacks-answer-neither/
-->
<!--[if lt IE 7]> 
    <div class="no-js lt-ie9 lt-ie8 lt-ie7" lang="en">
<![endif]-->
<!--[if IE 7]>
    <div class="no-js lt-ie9 lt-ie8 ie7" lang="en">
<![endif]-->
<!--[if IE 8]>
    <div class="no-js lt-ie9 ie8" lang="en">
<![endif]-->
<!--[if gt IE 8]><!-->
    <div class="no-js no-ie" lang="en">
<!--<![endif]-->

<button class="btn btn_green btn_small ">
    Send
    <!--[if lte IE 8]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn">
    Buy
    <!--[if lte IE 8]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn btn_green">
    Activate
    <!--[if lte IE 8]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

<button class="btn btn_red">
    Delete
    <!--[if lte IE 8]> <span class="before"> </span><span class="after"> </span> <![endif]-->
</button>

</div>

---

Update 2:

I solved my problem, but the main question is still unanswered:

“Why don’t filters work on pseudo elements in IE8?”

Started a bounty.

Update 3:
I created testcase only for filters(and also -ms-filter) on ie8:

But the filters still don’t want to work on pseudo-elements.

Update 4:
I think Scotts answer is closest to truth.

Answer 1

The question is “Why don’t filters work on pseudo elements in IE8?” The following is as close to a definitive answer as I can muster. It comes from the information on this page.

The gradient filter is a “procedural surface” (along with alphaimageloader). A procedural surface is defined so:

Procedural surfaces are colored surfaces that display between the
content of an object and the object’s background.

Read that carefully. It is essentially another “layer” you might say between the content of an object and that object’s background. Do you see the answer to the question? What is created by :before and :after… Yes! Content. Specifically as MSDN notes:

The ::before and ::after pseudo-elements specify the location of
content before and after an element in the document tree. The content
attribute, in conjunction with these pseudo-elements, specifies what
is inserted.

The generated content interacts with other boxes as if they were real
elements inserted just inside their associated element.

Now, if it is content that is generated, then it is not an “object” containing content, but the content itself (which happens to have some behavior similar to an element object that might contain content).

Thus, there is no “object” containing “content” (since it is content) between which the filter can place a procedural surface for content generated by a pseudo-element (i.e. “false element”). A gradient must be applied to the object, and then the procedural surface is placed between it and the content.