Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Patent
1994-08-16
1996-04-30
Berman, Susan W.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
522135, 522136, 522144, 522164, 522134, C08F 250, C08L 7702, C08L 7706
Patent
active
055126065
DESCRIPTION:
BRIEF SUMMARY
This invention relates to materials based on linear polyamides and to articles such as fibres and films produced from such materials, and in particular to materials and articles which are photo-crosslinkable.
The normal effect of radiation on polyamides is to cause degradation by breaking of the polymer chain. Although the use of a polymide in photo-crosslinkable materials is known, the polymide itself takes little or no part in the crosslinking, being only present as a support. In such materials the photo-crosslinking is produced by a photopolymerisable monomer containing, for example unsaturated groups as described in U.S. Pat. No. 4,144,073. An improvement can be effected by additionally providing unsaturated groups grafted onto the polymide backbone as described in U.S. Pat. No. 4,421,840.
Surprisingly, it has now been found that photo-crosslinking of polyamides can be effected by using a suitable photo-crosslinking agent without the necessity of the unsaturated photo-polymerisable groups being present.
According to one aspect of the present invention there is provided a photo-crosslinkable material comprising a linear polymide and a 2-substituted anthraquinone as photo-crosslinking agent.
According to a preferred aspect of the invention, the 2-substituted anthraquinone has the formula ##STR1## where X is selected from a group consisting of NHC(O)CH.dbd.CH.sub.2, OC(O)CH.dbd.CH.sub.2, OC(O)C(CH.sub.3).dbd.CH.sub.2 and NHC(O)C.sub.6 H.sub.5. substituted.
Preferably the 2-substituted anthraquinone is 2-acrylamidoanthraquinone (X.dbd.NHC(O)CH.dbd.CH.sub.2), or 2-acryloxyanthraquinone (X.dbd.OC(O)CH.dbd.CH.sub.2), or 2-benzoylaminoanthraquinone (X.dbd.NHC(O)C.sub.6 H.sub.5).
The photo-crosslinkable material may contain two or more of the 2-substituted anthraquinones or a mixture of one or more of the 2-substituted anthraquinones with one or more other photoinitiator materials.
Any polyamide may be used but poly(hexamethylene adipamide) (more commonly known as nylon 6.6) or polycaprolactam (more commonly known as nylon 6) is preferred.
According to a further aspect of the invention there is provided a solvent--cast film or a melt spun fibre comprising a polyamide having incorporated therein, or coated on the surface thereof, a 2-substituted anthraquinone.
The 2-substituted anthraquinone may be incorporated into the polymer before or during the melt spinning or may be applied to the surface of the fibre as a spin finish or during the dyeing process.
Photo-crosslinking may be effected using radiation from sources having emission maxima in the range 200 to 500 mm and especially in the range 400 to 500 mm. Such sources may be actinic or super actinic fluorescent tubes, mercury vapour lamps and xenon lamps.
Whilst the 2-substituted anthraquinones are known generally, compounds containing a (meth)acryloxy group in the 2-position are novel.
Hence, according to a further aspect of the invention, there is provided a photoiniator compound having the formula ##STR2## where R is hydrogen or a methyl group.
The invention will be illustrated by the following examples.
EXAMPLE 1
Nylon 6.6 chips (2% by weight) were dissolved in trifluoroethanol and 0.2% by weight 2-acrylamidoanthraquinone (AAAQ) added. A series of film samples was produced by spreading the resultant solution on glass plates and evaporating the solvent. Control samples not containing the AAAQ were also prepared.
The films were removed from the plates and irradiated for various times using a 400 watt mercury lamp.
The amount of gel formation, which is proportional to the degree of cross-linking, was determined by dissolving a sample in a fixed volume of formic acid, pouring the solution into a glass funnel containing a glass wool plug (the funnel and plug having been dried to constant weight) to filter out the undissolved gel, washing with a fixed volume of formic acid and again drying to constant weight. The results are shown in Table 1.
EXAMPLE 2
Example 1 was repeated except that 2-acryloxyanthraquinone (AOAQ) and 2-benzoylaminoanthraquinone (BOAAQ)
REFERENCES:
patent: 3591661 (1971-07-01), Rogers
patent: 4198241 (1980-04-01), Bronstert et al.
patent: 4767642 (1988-08-01), Shimizu et al.
patent: 4988664 (1991-01-01), Smith et al.
patent: 5283160 (1994-02-01), Allen et al.
Allen Norman S.
Hurley John P.
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