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US 6,664,363 B1Granted
Low viscosity polyester polyols and methods for preparing same
AssigneeStepan Company
InventorJames A. Faunce
Life of this patent
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Abstract
The present invention relates to low viscosity aromatic polyester polyols having an average functionality of two and methods for preparing such polyols. In particular, the invention relates to low viscosity aromatic polyester polyols prepared by reacting a phthalic acid based material with diethylene glycol, a higher functional polyol having an average functionality of greater than two and a long chain alkyl acid, ester or oil. The resulting aromatic polyester polyol has an average functionality of two and has a lower dynamic viscosity as compared to the esterification product of a phthalic acid based material with diethylene glycol alone.
Claims16
A low viscosity aromatic polyester polyol comprising the inter-esterification product of
- (a) from about 20 to about 80 mole percent of at least one phthalic acid based material selected from the group consisting of phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, methyl esters of phthalic, isophthalic, or terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, and mixtures thereof;
- (b) from about 20 to about 80 mole percent of at least one low molecular weight aliphatic diol of the formula
- HO—R1—OH
- wherein R1 is a divalent radical selected from the group consisting of
- (i) alkylene radicals each containing from 2 through 12 carbon atoms;
- (ii) radicals of the formula —[CH2—R2—CH2]— wherein R2 is a radical selected from the group consisting of
- (iii) radicals of the formula
- —[(R3O)n—R3]—
- wherein R3 is an alkylene radical containing from 2-4 carbon atoms and n is an integer from 1 through 10;
- and mixtures thereof;
- (c) from about 0.1 to about 20 mole percent of a higher functional polyol selected from the group consisting of
- alkoxylated glycerine, sucrose, alkoxylated sucrose, methyl glucoside, alkoxylated methyl glucoside, glucose, alkoxylated glucose, fructose, alkoxylated fructose, alkoxylated sorbitol, lactose, alkoxylated lactose,
- and mixtures thereof;
- and
- (d) from about 0.1 to about 20 mole percent of at least one hydrophobic material characterized by
- (i) having an equivalent weight of about 130-1000;
- (ii) containing from about 8 to 60 carbon atoms;
- and
- (iii) containing at least one and not more than four radicals per molecule, which are selected from the group consisting of carboxyl, hydroxyl, and mixtures thereof;
- wherein the aromatic polyester polyol has an average functionality of about two.
17 more elements
A low viscosity aromatic polyester polyol comprising the inter-esterification product of
- (a) from about 20 to about 80 mole percent of at least one phthalic acid based material selected from the group consisting of phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, methyl esters of phthalic, isophthalic, or terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, and mixtures thereof;
- (b) from about 20 to about 80 mole percent of at least one low molecular weight aliphatic diol of the formula
- HO—R1—OH
- wherein R1 is a divalent radical selected from the group consisting of
- (i) alkylene radicals each containing from 2 through 12 carbon atoms;
- (ii) radicals of the formula —[CH2—R2—CH2]— wherein R2 is a radical selected from the group consisting of
- (iii) radicals of the formula
- —[(R3O)n—R3]—
- wherein R3 is an alkylene radical containing from 2-4 carbon atoms and n is an integer from 1 through 10;
- and mixtures thereof;
- (c) from about 0.1 to about 20 mole percent of a higher functional polyol selected from the group consisting of
- alkoxylated glycerine, sucrose, alkoxylated sucrose, methyl glucoside, alkoxylated methyl glucoside, glucose, alkoxylated glucose, fructose, alkoxylated fructose, alkoxylated sorbitol, lactose, alkoxylated lactose, and mixtures thereof;
- wherein (a), (b), and (c) are interesterified to form an intermediate polyester polyol, which is further esterified with
- (d) from about 0.1 to about 20 mole percent of at least one hydrophobic material characterized by
- (i) having an equivalent weight of about 130-1000;
- (ii) containing from about 8 to 60 carbon atoms;
- and
- (iii) containing at least one and not more than four radicals per molecule, which are selected from the group consisting of carboxyl, hydroxyl, and mixtures thereof;
- wherein the aromatic polyester polyol has an average functionality of about two.
16 more elements
A process for producing a low viscosity aromatic polyester polyol having an average functionality of about two, comprising inter-esterifying in any order
- (a) from about 20 to about 80 mole percent of at least one phthalic acid based material selected from the group consisting of phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, methyl esters of phthalic, isophthalic, or terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, and mixtures thereof;
- (b) from about 20 to about 80 mole percent of at least one low molecular weight aliphatic diol of the formula
- HO—R1—OH
- wherein R1 is a divalent radical selected from the group consisting of
- (i) alkylene radicals each containing from 2 through 12 carbon atoms;
- (ii) radicals of the formula —[CH2—R2—CH2]— wherein R2 is a radical selected from the group consisting of
- (iii) radicals of the formula
- —[(R3O)n—R3]—
- wherein R3 is an alkylene radical containing from 2-4 carbon atoms and n is an integer from 1 through 10;
- and or mixtures thereof;
- (c) from about 0.1 to about 20 mole percent of a higher functional polyol selected from the group consisting of
- alkoxylated glycerine, sucrose, alkoxylated sucrose, methyl glucoside, alkoxylated methyl glucoside, glucose, alkoxylated glucose, fructose, alkoxylated fructose, aorbitol, alkoxylated sorbitol, lactose, and alkoxylated lactose, and mixtures thereof;
- and
- (d) from about 0.1 to about 20 mole percent of at least one hydrophobic material characterized by
- (i) having an equivalent weight of about 130-1000;
- (ii) containing from about 8 to 60 carbon atoms;
- and
- (iii) containing at least one and not more than four radicals per molecule, which are selected from the group consisting of carboxyl, hydroxyl, and mixtures thereof.
15 more elements
A process for producing a low viscosity aromatic polyester polyol having an average functionality of about two, comprising inter-esterifying in any order
- (a) from about 20 to about 80 mole percent of at least one phthalic acid based material selected from the group consisting of phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, methyl esters of phthalic, isophthalic, or terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, and mixtures thereof;
- (b) from about 20 to about 80 mole percent of at least one low molecular weight aliphatic diol of the formula
- HO—R1—OH
- wherein R1 is a divalent radical selected from the group consisting of
- (i) alkylene radicals each containing from 2 through 12 carbon atoms;
- (ii) radicals of the formula —[CH2—R2—CH2]— wherein R2 is a radical selected from the group consisting of
- (iii) radicals of the formula
- —[(R3O)n—R3]—
- wherein R3 is an alkylene radical containing from 2-4 carbon atoms and n is an integer from 1 through 10;
- and mixtures thereof;
- (c) from about 0.1 to about 20 mole percent of a higher functional polyol selected from the group consisting of
- alkoxylated glycerine, sucrose, alkoxylated sucrose, methyl glucoside, alkoxylated methyl glucoside, glucose, alkoxylated glucose, fructose, alkoxylated fructose, alkoxylated sorbitol, lactose, alkoxylated lactose, and mixtures thereof;
- wherein (a), (b), and (c) are interesterified to form an intermediate polyester polyol, which is further esterified with
- (d) from about 0.1 to about 20 mole percent of at least one hydrophobic material characterized by
- (i) having an equivalent weight of about 130-1000;
- (ii) containing from about 8 to 60 carbon atoms;
- and
- (iii) containing at least one and not more than four radicals per molecule, which are selected from the group consisting of carboxyl, hydroxyl, and mixtures thereof.
15 more elements
Dependencies are inferred from the claim text.