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US 8,946,345 B2Granted
Method for the preparation of (polybutylene-co-adipate terephthalate) through the in situ phosphorus containing titanium based catalyst
AssigneeSaudi Basic Industries Corporation
InventorsHusnu Alp Alidedeoglu, Hareesh Shamroa Deshpande, Belinda Duckworth, Tukaram Gunale, Darshan Jayanna, Ganesh Kannan
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Abstract
Biodegradable compositions containing an aliphatic-aromatic copolyester derived from aromatic polyesters. Methods of making the compositions through an in situ phosphorus containing titanium based catalyst and articles made from the compositions.
Claims23
An aliphatic-aromatic copolyester that is a polymer reaction product in which an aliphatic-aromatic copolyester polymer is formed that comprises:
- (a) a dihydric alcohol group, which is a residue of a dihydric alcohol, selected from an ethylene glycol group, 1,2-propylene glycol group, 1,3-propylene glycol group, 1,2-butanediol group, 2,3-butanediol group, 1,4-butanediol group, tetramethyl cyclobutanediol, isosorbide groups, 1,3-cyclohexanedimethanol groups, 1,4-cyclohexanedimethanol groups, hexylene glycol groups, bio-derived diol groups, and combinations thereof;
- (b) an aromatic dicarboxylic acid group, which is a residue of an aromatic dicarboxylic acid, derived from a depolymerized aromatic polyester component selected from poly(ethylene terephthalate)s, poly(butylene terephthalate)s, poly(trimethylene terephthalate)s, and combinations thereof;
- and
- (c) an adipic acid group, which is a residue of adipic acid;
- wherein the reaction product further comprises an aromatic polyester residue selected from an isophthalic acid group, antimony-containing compounds, germanium-containing compounds, cobalt-containing compounds, tin, tin-containing compounds, titanium, titanium-containing compounds, aluminum, aluminum salts, alkaline salts, alkaline earth metal salts, phosphorus-containing compounds, sulfur-containing compounds, naphthalene dicarboxylic acid groups, epoxies, and combinations thereof;
- wherein the aliphatic-aromatic copolyester has a number average molecular weight of at least 20,000 Daltons and a polydispersity index from 2 to less than 6;
- wherein the reaction product further comprises titanium catalyst that is a product of a process comprising an in situ reaction of an organo-titanium catalyst and a color-reducing amount of a reactant selected from phosphorus-containing compounds, nitrogen-containing compounds, boron-containing compounds, and combinations thereof;
- wherein the aliphatic-aromatic copolyester is made by a process, carried out in the presence of the titanium catalyst, in which the adipic acid group is incorporated into the copolyester when the aromatic polyester component reacts with the first dihydric alcohol and the adipic acid;
- and
- wherein the copolyester obtains a Tm from 90° C. to 160° C. and a whiteness of at least L*=70.0 as determined by a colorimeter using D65 illumination.
7 more elements
An aliphatic-aromatic copolyester that is a polymer reaction product in which an aliphatic-aromatic copolyester polymer is formed comprises:
- (a) a dihydric alcohol group, which is a residue of a dihydric alcohol, selected from an ethylene glycol group, 1,2-propylene glycol group, 1,3-propylene glycol group, 1,2-butanediol group, 2,3-butanediol group, 1,4-butanediol group, tetramethyl cyclobutanediol, isosorbide groups, 1,3-cyclohexanedimethanol groups, 1,4-cyclohexanedimethanol groups, hexylene glycol groups, bio-derived diol groups, and combinations thereof;
- (b) an aromatic dicarboxylic acid group, which is a residue of an aromatic dicarboxylic acid, derived from a depolymerized aromatic polyester component selected from poly(ethylene terephthalate)s, poly(butylene terephthalate)s, poly(trimethylene terephthalate)s, and combinations thereof;
- and
- (c) an adipic acid group, which is a residue of adipic acid;
- wherein the reaction product further comprises an aromatic polyester residue selected from an isophthalic acid group, antimony-containing compounds, germanium-containing compounds, cobalt-containing compounds, tin, tin-containing compounds, titanium, titanium-containing compounds, aluminum, aluminum salts, alkaline salts, alkaline earth metal salts, phosphorus-containing compounds, sulfur-containing compounds, naphthalene dicarboxylic acid groups, epoxies, and combinations thereof,
- wherein the aliphatic-aromatic copolyester has a number average molecular weight of at least 20,000 Daltons and a polydispersity index from 2 to less than 6;
- wherein the reaction product further comprises a titanium catalyst comprising titanium and a color-reducing amount of a compound selected from phosphorus-containing compounds, boron-containing compounds, and combinations thereof;
- wherein the titanium catalyst is a product made by a process comprising an in situ reaction of a tetraisopropyl titanate and a reactant selected from
- (1) phosphorus-containing compounds, at a molar ratio of the phosphorus-containing compound:tetraisopropyl titanate from more than 0.5:1 to less than or equal to 3:1, and
- (2) boron-containing compounds, at a molar ratio of the boron-containing compound:tetraisopropyl titanate from more than 0.5:1 to less than or equal to 4:1, and
- (3) combinations thereof;
- wherein the reactant comprises acidic hydroxy groups that achieve complete conversion in the in situ reaction;
- wherein the aliphatic-aromatic copolyester is made by a process, carried out in the presence of the titanium catalyst, in which the adipic acid group is incorporated into the an aliphatic-aromatic copolyester polymer when the aromatic polyester component reacts with the first dihydric alcohol and the adipic acid;
- and
- wherein the copolyester obtains a Tm from 90° C. to 160° C. and a whiteness of at least L*=70.0 as determined by a colorimeter using D65 illumination.
12 more elements
Dependencies are inferred from the claim text.