Furyl-2-methylidene UV absorbers and compositions incorporating the UV absorbers
First Claim
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1. A method of incorporating a UV absorber into a polyester resin, the method comprising:
- a) forming a reaction mixture substantially free of a titanium containing ester exchange catalyst compound and comprising;
a diol, a diacid component selected from the group consisting of dicarboxylic acids, dicarboxylic acid derivatives, and mixtures thereof, an antimony containing compound in an amount of less than 0.1% of the total weight of the reaction mixture, a phosphorus containing compound present in an amount of less than about 0.1% of the total weight of the reaction mixture, a metal containing compound selected from the group consisting of zinc containing compounds, manganese containing compounds, present in an amount from about 10 ppm to about 300 ppm, and a UV absorbing compound, wherein said UV absorbing compound comprises at least one furyl-2-methylidene radical of Formula I;
wherein the UV absorbing compound includes a polyester reactive group; and
b) polymerizing the reaction mixture in a polycondensation reaction system, the polycondensation reaction system having a first reaction chamber, a last reaction chamber, and one or more intermediate reaction chambers between the first reaction chamber and the last reaction chamber, wherein the reaction system is operated in series such that the reaction mixture is progressively polymerized in the first reaction chamber, the one or more intermediate reactions, and the last reaction chamber.
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Abstract
A method for efficiently incorporating a UV absorber into a polyester resin. The method includes forming a reaction mixture comprising a diol component, a diacid component selected from the group consisting of dicarboxylic acids, dicarboxylic acid derivatives, and mixtures thereof, an antimony containing compound, a phosphorus containing compound, a metal containing compound, and a UV absorber. The reaction mixture is polymerized in a polycondensation reaction system. In another embodiment of the present invention, the UV absorber is added while the reaction products from one reactor are transferred to the next reactor in the polycondensation reaction system. The present invention is also directed to novel UV absorbing compounds as well as articles made from the polyester resin.
81 Citations
64 Claims
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1. A method of incorporating a UV absorber into a polyester resin, the method comprising:
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a) forming a reaction mixture substantially free of a titanium containing ester exchange catalyst compound and comprising;
a diol, a diacid component selected from the group consisting of dicarboxylic acids, dicarboxylic acid derivatives, and mixtures thereof, an antimony containing compound in an amount of less than 0.1% of the total weight of the reaction mixture, a phosphorus containing compound present in an amount of less than about 0.1% of the total weight of the reaction mixture, a metal containing compound selected from the group consisting of zinc containing compounds, manganese containing compounds, present in an amount from about 10 ppm to about 300 ppm, and a UV absorbing compound, wherein said UV absorbing compound comprises at least one furyl-2-methylidene radical of Formula I;
wherein the UV absorbing compound includes a polyester reactive group; and
b) polymerizing the reaction mixture in a polycondensation reaction system, the polycondensation reaction system having a first reaction chamber, a last reaction chamber, and one or more intermediate reaction chambers between the first reaction chamber and the last reaction chamber, wherein the reaction system is operated in series such that the reaction mixture is progressively polymerized in the first reaction chamber, the one or more intermediate reactions, and the last reaction chamber. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19)
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20. A method of incorporating a UV absorber into a polyester resin, the method comprising:
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a) forming a reaction mixture comprising combining;
a diol, a diacid component selected from the group consisting of dicarboxylic acids, dicarboxylic acid derivatives, and mixtures thereof in a polycondensation reaction system comprising a series of reaction chambers designatable as reaction chamber RCi having a first reaction chamber designatable as reaction chamber RC1, a last reaction chamber designatable as reaction chamber RCk, and one or more intermediate reaction chambers b) successively polymerizing the reaction mixture in the multi-chamber reaction polymerization system wherein the reaction system is operated in series such that a reaction product designatable as product Pi from reaction chamber RCi is transportable to reaction chamber RCi+1 by a conduit designatable as conduit Ci connecting reaction chamber RCi to a reaction chamber RCi+1; and
c) adding the UV absorber to reaction product Pi as it is transported from reaction chamber RCi to reaction chamber RCi+1, wherein i and k are integer and k is the total number of reaction chambers. - View Dependent Claims (21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39)
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40. A polyester composition comprising:
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diacid residues;
diol residues;
UV absorber residues from a UV absorber having Formula I;
and wherein the UV absorbing compound includes a polyester reactive group;
antimony atoms present in an amount of less than 0.1%;
phosphorus atoms present in an amount of less than about 0.1%;
metal atoms selected from the group consisting of zinc, manganese, and mixtures thereof in an amount from about 10 ppm to about 300 ppm; and
optionally titanium atoms present in an amount of 0.0 to 5 ppm. - View Dependent Claims (41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62)
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63. A UV absorbing compound having the general Formula:
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wherein;
X is selected from the group consisting of oxygen, —
NH—
, and —
N(R′
)—
;
n is a whole number ranging from 2 to 4;
R1 is selected from the group consisting of —
CO2R3 and cyano;
R3 is selected from the group consisting of hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, —
(CHR′
—
CHR″
O—
)pCH2CH2R4, C3-C8-alkenyl, C3-C8-cycloalkyl, aryl and cyano;
R4 is selected from the group consisting of hydrogen, hydroxy, C1-C6-alkoxy, C1-C6-alkanoyloxy and aryloxy;
R′ and
R″
are independently selected from hydrogen and C1-C12-alkyl;
L1 is a di, tri, or tetravalent linking group, where the divalent radical is selected from the group consisting of C2-C12-alkylene, —
(CHR′
CHR″
O—
)pCHR′
CHR″
—
, C1-C2-alkylene-arylene-C1-C2-alkylene, —
CH2CH2O-arylene-OCH2CH2—
, and —
CH2-1,4-cyclohexylene-CH2—
;
where the trivalent and tetravalent radicals are selected from the group consisting of C3-C8 aliphatic hydrocarbon having three or four covalent bonds.- View Dependent Claims (64)
wherein;
X is selected from the group consisting of oxygen, —
NH—
, and —
N(R′
)—
;
n is 2; and
L2 is selected from the group consisting of C2-C6-alkylene, —
(CHR′
CHR″
O—
)pCHR′
CHR″
—
, and —
CH2-cyclohexane-1,4-diyl-CH2—
.
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Specification
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Current AssigneeEastman Chemical Company
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Original AssigneeEastman Chemical Company
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InventorsColhoun, Frederick Leslie, Weaver, Max Allen, Pearson, Jason Clay, Blakely, Dale Milton
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Application NumberUS10/855,612Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current524/111CPC Class CodesC08G 63/6856 Dicarboxylic acids and dihy...C08G 63/866 Antimony or compounds thereofC08K 5/1535 Five-membered ringsC08L 67/02 Polyesters derived from dic...
