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KR-102962605-B1 - Polyester impact modifier

KR102962605B1KR 102962605 B1KR102962605 B1KR 102962605B1KR-102962605-B1

Abstract

A polyester composed of the following is disclosed: (1) monomer repeating units of isosorbide in an amount of about 15 to about 40 weight%; (2) monomer repeating units of a dicarboxylic acid or anhydride in an amount of about 25 to about 60 weight%, e.g., succinic acid or anhydride; and (3) monomer repeating units of a polyhydric alcohol in an amount of about 10 to about 20 weight%, e.g., 1,3-propanediol. In some examples, the polymer may also comprise monomer repeating units of methyl nadic anhydride or nadic anhydride. A polymer composition comprising not only the polyester but also a biodegradable polymer selected from the group consisting of poly(lactic acid), poly(hydroxyalkanoate) and mixtures thereof is also disclosed.

Inventors

  • 터윌에거 아른 매튜
  • 듀리 카슨
  • 쿤두 망갈딥

Assignees

  • 데니머 아이피씨오 엘엘씨

Dates

Publication Date
20260512
Application Date
20220513
Priority Date
20220513

Claims (20)

  1. As a polyester comprising the following, 15 to 40 weight percent of monomer repeating units of isosorbide based on the total weight of the polyester; Monomeric repeating units of a dicarboxylic acid or anhydride in an amount of 25 to 60 weight% based on the total weight of the polyester; and 10 to 20 weight percent of monomer repeating units of polyhydric alcohol based on the total weight of the polyester, Having a weight-average molecular weight of at least 8,000 daltons as measured by ASTM D5296-05, Polyester comprising a mixture of the following (1) and (2) with a dicarboxylic acid or anhydride. (1) Succinic acid or succinic anhydride (2) Nadic anhydride or methyl nadic anhydride
  2. The polyester of claim 1, wherein the polyester comprises 25 to 35 weight% succinic acid or succinic anhydride and 10 to 25 weight% nadic anhydride or methyl nadic anhydride.
  3. A polyester selected from the group consisting of glycerin, ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, propylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, trimethylene glycol, 1,1,1-trimethylol ethane, 1,2,3-trimethylolpropane, methylpropanediol, pentaerythritol, and poly(oxyalkylene) polyols comprising monomer repeating units of ethylene oxide, propylene oxide, or butylene oxide, and mixtures thereof.
  4. A polyester according to claim 1, wherein the polyhydric alcohol is selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, methylpropanediol, and mixtures thereof.
  5. In claim 1, a polyester comprising 1,3-propanediol as the polyhydric alcohol.
  6. In claim 1, a polyester having a weight average molecular weight of 10,000 to 15,000 daltons as measured by ASTM D5296-05.
  7. A polymer composition comprising the following: A biodegradable polymer selected from the group consisting of poly(lactic acid), poly(hydroxyalkanoate) and mixtures thereof, in an amount of 50 to 95 weight%; and 5 to 50 weight% of impact-modified polyester, wherein the impact-modified polyester is: 15 to 40 weight percent of monomer repeating units of isosorbide based on the total weight of the polyester; Monomeric repeating units of a dicarboxylic acid or anhydride in an amount of 25 to 60 weight% based on the total weight of the polyester; and Based on the total weight of the polyester, it comprises 10 to 20 weight percent of monomer repeating units of polyhydric alcohol, and Polyester has a weight-average molecular weight of at least 8,000 daltons, as measured by ASTM D5296-05, and A polymer composition comprising a mixture of the following (1) and (2) of a dicarboxylic acid or anhydride. (1) Succinic acid or succinic anhydride (2) Nadic anhydride, methyl nadic anhydride, C36 dimeric acid, partially hydrogenated C36 dimeric acid, or a mixture thereof
  8. A polymer composition according to claim 7, wherein the polyester comprises 25 to 35 weight% succinic acid or succinic anhydride and 10 to 25 weight% nadic anhydride, methyl nadic anhydride, C36 dimeric acid, or partially hydrogenated C36 dimeric acid.
  9. A polymer composition according to claim 7, wherein the polyhydric alcohol is selected from the group consisting of glycerin, ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, propylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, trimethylene glycol, 1,1,1-trimethylol ethane, 1,2,3-trimethylolpropane, methylpropanediol, pentaerythritol, and poly(oxyalkylene) polyols comprising monomer repeating units of ethylene oxide, propylene oxide, or butylene oxide, and mixtures thereof.
  10. A polymer composition according to claim 7, wherein the polyhydric alcohol is selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, methylpropanediol, and mixtures thereof.
  11. In claim 7, a polymer composition in which the polyhydric alcohol comprises 1,3-propanediol.
  12. In claim 7, the impact-modified polyester is a polymer composition having a weight average molecular weight of 10,000 to 15,000 daltons as measured by ASTM D5296-05.
  13. A polymer composition according to claim 7, comprising 60 to 85 weight% of a biodegradable polymer and 5 to 30 weight% of an impact-modified polyester.
  14. In claim 7, the biodegradable polymer comprises a polymer composition including poly(lactic acid).
  15. A polymer composition according to claim 7, wherein the biodegradable polymer comprises at least one poly(hydroxyalkanoate).
  16. A polymer composition according to claim 15, wherein at least one poly(hydroxyalkanoate) comprises poly-3-hydroxybutyrate-co-3-hydroxyhexanoate ("P(3HB-co-3HHx)").
  17. A polymer composition according to claim 16, wherein P(3HB-co-3HHx) comprises 75 to 99 mol% hydroxybutyrate and 1 to 25 mol% hydroxyhexanoate.
  18. A polymer composition according to claim 16, wherein P(3HB-co-3HHx) comprises 93 to 98 mol% hydroxybutyrate and 2 to 7 mol% hydroxyhexanoate.
  19. A polymer composition according to claim 15, comprising a terpolymer in which at least one poly(hydroxyalkanoate) is composed of a monomer repeating unit of 75 to 99.8 mol% 3-hydroxybutyrate, a monomer repeating unit of 0.1 to 24.9 mol% 3-hydroxyhexanoate, and a monomer repeating unit of 0.1 to 24.9 mol% 3-hydroxyalkanoate having 5 to 12 carbon atoms.
  20. A polymer composition according to claim 15, wherein at least one poly(hydroxyalkanoate) has a weight average molecular weight of 50,000 daltons to 2.5 million daltons as measured by ASTM D5296-05.

Description

Polyester impact modifier The present disclosure relates to a polyester suitable for use as an impact modifier and a biodegradable polymer composition comprising such impact modifier. For decades, petroleum-based polymers such as polyethylene (PE), polypropylene (PP), or polyethylene terephthalate (PET) have been used in various applications. While these polymers can provide excellent strength, barrier, and/or printability properties, unfortunately, they do not easily decompose or break down after disposal, whether through landfill or household composting technologies. Consequently, films, bags, and other materials made from such polymers can remain in landfills for centuries after disposal. As a result, there is an increasing demand for alternative polymers that are biosource, biodegradable, and/or compostable. Examples of such polymers include poly(lactic acid) and poly(hydroxyalkanoates). While these biopolymers offer clear advantages in terms of biodegradability and/or compostability, it is typically desirable to blend various additives with the biopolymers to improve their physical properties. If the additive blended into the biopolymer is not biodegradable or/or compostable, the environmental benefits of the biopolymer are reduced. Consequently, it would be desirable to provide an additive for use with the biopolymer, such as incorporating poly(lactic acid) and poly(hydroxyalkanoate) which are themselves biodegradable and/or compostable. Examples The following non-limiting examples illustrate various additional aspects of the invention. Unless otherwise specified, temperatures are in degrees Celsius, and percentages are percentages of weight relative to the dry weight of the formulation. Example 1 800 grams of isosorbide and 5 grams of phosphoric acid were charged into a reaction flask equipped with a nitrogen inlet and a vacuum function. The reaction temperature was raised to 100°C, and three vacuum cycles were performed by drawing the contents of the flask under maximum vacuum and then releasing the vacuum using an inert gas such as nitrogen. Subsequently, 1279 grams of succinic acid were charged, and one or more vacuum cycles were performed. Next, the reactor temperature was raised to a maximum of 220°C, during which time water was distilled into the receiver. Once the generation of water slowed down, 416 grams of propanediol were charged into the reactor. The temperature was again slowly raised to a maximum of 210°C. Until the reaction was complete, 1 gram of tin (II) ethylhexanoate was added and a vacuum was applied. The material was maintained until a suitable molecular weight specification was obtained. Example 2 416 kg of isosorbide and 2.27 kg of phosphoric acid were charged into a 1514 L stainless steel reactor equipped with a nitrogen inlet and vacuum function. The reaction temperature was raised to 100°C, and three vacuum cycles were performed by drawing the contents of the reactor to maximum vacuum and then releasing the vacuum using an inert gas such as nitrogen. Subsequently, 590 kg of succinic acid was charged, and one or more vacuum cycles were performed. Next, the reactor temperature was raised to a maximum of 220°C, during which time water was distilled into the receiver. Once the generation of water slowed down, 216 kg of propanediol was charged into the reactor. The temperature was again slowly raised to a maximum of 210°C. Until the reaction was complete, 453 grams of tin (II) ethylhexanoate were added. The material was maintained until a suitable molecular weight specification was obtained. Example 3 575 grams of isosorbide, 888 grams of partially hydrogenated, distilled C36 dimeric acid, and 5 grams of phosphoric acid were charged into a reaction flask equipped with a nitrogen inlet and a vacuum function. The reaction temperature was raised to 100°C, and three vacuum cycles were performed by drawing the contents of the flask under maximum vacuum and then releasing the vacuum using an inert gas such as nitrogen. Subsequently, 733 grams of succinic acid were charged, and one or more vacuum cycles were performed. Next, the reactor temperature was raised to a maximum of 220°C, during which time water was distilled into the receiver. Once the generation of water slowed down, 299 grams of propanediol were charged into the reactor. The temperature was again slowly raised to a maximum of 220°C. Until the reaction was complete, 1 gram of tin(II) ethylhexanoate was added and a vacuum was applied. The material was maintained until a suitable molecular weight specification was obtained. Example 4 2,314 grams of polyester from Example 2 and 186 grams of methyl nadic anhydride were charged into a reaction flask equipped with a nitrogen inlet and a vacuum function. The reactor temperature was raised to a maximum of 220°C, during which time water was distilled into the receiver. At the end of the reaction, 0.63 grams of tin(II) ethylhexanoate were added. The material was maintained until a sui