Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2000-07-26
2002-12-24
Boykin, Terressa M. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C442S059000, C528S193000, C528S194000, C428S364000, C428S373000
Reexamination Certificate
active
06498227
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a flame retardant. More particularly, it relates to a flame retardant useful as a fiber-treatment for imparting flame retardancy to polyester textile materials.
2. Description of the Prior Art
There have been proposed several fiber-treatments for imparting flame retardancy to polyester textile materials, for example, (1) an aqueous dispersion of hexabromocyclo-dodecane (JPN Patent Lay-open No.137377/1982), and (2) an aqueous dispersion comprising (A) a phosphorus-containing polyester composed of polycarboxylic components comprising a metal sulfonate group-containing aromatic dicarboxylic acid, (B) a water-soluble organic solvent and (C) water (JPN Patent Lay-open No.27741/1983).
The use of such a halogen-containing compound as in the above (1), however, has a problem of environmental pollution.
The use of such a phosphorus-containing polyester having a metal sulfonate group in the above (2) has no such problem, but is not always satisfied with respect to durability of flame retardancy.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a fiber-treatment capable of providing improved flame retardancy towards synthetic fiber comprising polyester.
It is another object of this invention to provide a halogen-free flame retardant for polyester-based synthetic fiber of improved durability.
It is still another object of the present invention to provide a flame resistant polyester-based textile material of improved resistances to washing and dry-cleaning.
It is yet another object of the present invention to provide a method for imparting flame retardancy to a polyester-based textile material through post-finishing.
Briefly, these and other objects of this invention as hereinafter will become more readily apparent have been attained broadly by: a fiber-treatment comprising a polyester obtained from (A) an aromatic dicarboxylic acid component, (B) a diol and (C) a phosphinic acid derivative represented by the formula (1).
In the formula (1), R
1
and R
2
are independently selected from the group consisting of hydrogen atom and hydrocarbyl groups containing 1-22 carbon atoms, or R
1
and R
2
are joined into a divalent group to form a ring together with the phosphorus and oxygen atoms; n is 0, 1 or 2; and Z is a monovalent succinic residue represented by
wherein R
3
is a hydrogen atom or an alkyl group containing 1-4 carbon atoms.
The aromatic dicarboxylic acid component (A) has no anionic group other than the carboxylic groups.
The molar ratio of (A)/(B)/(C) is 1/0.8-9/0.2-5.
The polyester has a weight-average molecular weight (hereinafter referred to as Kw) of about 500 to about 20,000.
The fiber-treatment is applied to synthetic fibers comprising polyester or textile materials therefrom to impart flame retardancy.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Suitable polyesters include ones obtainable by esterifying or transesterifying (A) an aromatic dicarboxylic acid or an ester-forming derivative thereof with the components (B) and (C).
Suitable aromatic dicarboxylic acids include ones represented by the general formula;
HOOC—Ar—COOH,
wherein Ar is a divalent aromatic hydrocarbon group containing 6-20 or more carbon atoms, which may contain one or more ether linkages or a sulfone group, for example, phenylene, alkyl-substituted phenylene, biphenylene, phenylmethylphenylene, naphthylene, phenoxyethoxyphenylene and phenylsulfonyl-phenylene groups.
Illustrative of suitable aromatic dicarboxylic acids are unsubstituted or alkyl-substituted benzenedicarboxylic acids, such as phthalic, isophthalic and terephthalic acids, toluenedicarboxylic acids, 4,4′-diphenyldicarboxylic acid, 4,4′-diphenylmethanedicarboxylic acid, 4,4′-diphenyl-sulfonedicarboxylic acid, diphenoxyethanedicarboxylic acids (such as 4,4, -dicarboxy-&agr;, &bgr;-diphenoxyethane), and naphthalenedicarboxylic acids (such 2,6- and 2,7-isomers).
Examples of suitable ester-forming derivatives include anhydrides, such as phthalic anhydride, lower alkyl (containing 1-4 carbon atoms; such as methyl and butyl) esters, such as dimethyl terephthalate, and acid halides (such as chlorides).
Among these, preferred are terephthalic acid and dimethyl terephthalate.
Suitable diols (B) include i) dihydric alcohols, for example, straight-chain and branched aliphatic diols, including alkylene glycols and alkenylene glycols, containing 2-12 carbon atoms, such as ethylene glycol, 1,2- and 1,3-propylene glycols, 1,4-butanediol, neopentyl glycol, 1,4-butenediol, 1,5-pentanediol and 1,6-hexanediol; cycloaliphatic diols containing 6-30 carbon atoms, such as 1,4-cyclohexane dimethanol and hydrogenated bisphenol A; and ii) oxyalkylated diols (including oxyalkylene diols and polyoxyalkylene diols), for example, alkylene oxide adducts of the above i), including polyalkylene glycols, such as diethylene glycol, dipropylene glycol, polyethylene glycols, polypropylene glycols and polytetramethylene glycols; and alkylene oxide adducts of dihydric phenols (monocyclic dihydric phenols, such as hydroquinone and alkyl-substituted hydroquinones having 1-4 alkyl groups containing 1-8 carbon atoms in each alkyl group; and bisphenols of the formula: HO—Ph—X—Ph—OH (wherein Ph is phenylene group, and X is direct linkage, alkylene, alkylidene or alkylene ether containing up to 8 carbon atoms, ether, sulfone, thioether or ketone linkage), such as bisphenol A, bisphenol F and bisphenol S); as well as combinations of two or more of these. Suitable alkylene oxides include ones containing 2-4 or more carbon atoms, for example, ethylene oxide, propylene oxide, 1,2-, 2,3-, 1,3- and 1,4-butylene oxides, and substituted alkylene oxides, such as styrene oxide and epichlorohydrin, as well as combinations of two or more of these alkylene oxides.
Molecular weight, as determined from hydroxyl number, of the diol (B) is not particularly restricted, but preferably not more than about 1,000 (particularly not more than about 500), in view of flame retarding effects of the resulting polyester.
Among these, preferred are dihydric alcohols, particularly alkylene glycols containing 2-10 carbon atoms. More preferred are alkylene glycols containing 2-6 carbon atoms, especially ethylene glycol.
In the general formula (1), suitable hydrocarbyl groups of R
1
and R
2
include i) straight-chain and branched alkyl groups containing 1-22 carbon atoms (preferably 1-6 carbon atoms), for example, methyl, ethyl, n- and i-propyl, n-, i-, sec- and t-butyl, n-pentyl, 3-methylbutyl, n-hexyl, 2-ethylbutyl, n- and i-heptyl, 2-ethylhexyl, n- and i-nonyl, n- and i-decyl, n-dodecyl, n-hexadecyl, n-octadecyl, n-icosyl and n-docosyl; ii) straight-chain and branched alkenyl groups containing 2-22 carbon atoms (preferably 2-6 carbon atoms), for example, vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 2-pentenyl, decenyl, dodecenyl, tridecenyl, hexa-decenyl, octadecenyl, icosenyl and docosenyl; cycloalkyl groups containing 5 or 6 carbon atoms, for example, cyclo-pentyl and cyclohexyl; aryl groups containing 6-14 carbon atoms, for example, phenyl, mono-, di-, tri- and tetra-alkyl-substituted phenyls (containing 1-8 carbon atoms in each alkyl group; such as tolyl, xylyl, mesityl, cumenyl and octylphenyl), biphenyl, naphthyl, anthryl and phenanthryl (preferably phenyl and biphenyl); aralkyl groups containing 1-4 carbon atoms in the alkylene group, preferably benzyl and phenethyl. Among hydrogen atom and these hydrocarbyl groups as R
1
and R
2
, preferred are hydrogen atom and lower alkyl groups, particularly methyl group, in view of flame retarding effects of the resulting polyester.
Suitable divalent group of joined R
1
and R
2
to form a ring together with the phosphorus and oxygen atoms include alkylene groups containing 2-44, preferably 2-12 carbon atoms, for example, polymethylene groups of the general formula:
—(CH
2
)x—
wherein x is an integer of 2-22 or more, preferably 3-12, (each of the methylene group may carry a lower alkyl substituent containing 1-4 carbon atoms), such as trimet
Boykin Terressa M.
Connolly Bove & Lodge & Hutz LLP
Sanyo Chemical Industries Ltd.
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