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Aliphatic polycarbonate macropolyol and aliphatic polycarbonate-co-aromatic polyester macropolyol

Inactive Publication Date: 2016-06-23
LOTTE CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about a method for creating macropolyols, which are low-molecular-weight polymers or copolymers made from high-molecular-weight polymers or copolymers by adding alcohol compounds as chopping agents. These macropolyols have precise control over their molecular weights and unique polymer chain distributions. The macropolyols also have a specific number of terminal —OH groups, which make them useful as raw materials for various applications such as polyurethane, coating materials, and lubricating agents.

Problems solved by technology

However, the condensation reactions are slow and have limitations in obtaining high-molecular-weight polymers.

Method used

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  • Aliphatic polycarbonate macropolyol and aliphatic polycarbonate-co-aromatic polyester macropolyol
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  • Aliphatic polycarbonate macropolyol and aliphatic polycarbonate-co-aromatic polyester macropolyol

Examples

Experimental program
Comparison scheme
Effect test

examples 1-9

Condensation of Formula 1a (and Optionally Formula 1b or 1c) with DMC and Subsequent Chopping of the Condensation Product with One of Formulae 1b to 1h

[0050]First step: 1,4-Butanediol (Formula 1a) and optionally 1,5-pentanediol (Formula 1b) or 1,6-hexanediol (Formula 1c) were placed in a 3-neck flask such that the total number of moles was 111 mmol. The 1,5-pentanediol or 1,6-hexanediol was used in the amount of 0 or 10 mol %, as shown in Table 1. NaH (0.056 mmol, 0.05 mol %) was added to the flask to form HO(CH2)4O−Na+ and then 15.7 g (174 mmol) of dimethyl carbonate (DMC) was added thereto. A mechanical stirrer was connected to one neck of the flask, a manifold attached with a vacuum line and a nitrogen line was connected to another neck of the flask, and a distillation unit was connected to the remaining neck of the flask. After the reaction flask was immersed in a thermostatic bath at 120° C., the reaction was carried out for 1 h while distilling off formed methanol and a portio...

examples 10-21

Condensation of Formula 1a (and Optionally Formula 1c) with DMC and Subsequent Chopping of the Condensation Product with One of Formulae 2a to 2d

[0053]The first step of Examples 1-9 was repeated.

[0054]The second step of Examples 1-9 was repeated, except that a diol selected from Formulae 2a to 2d was used as a chopping agent. The experimental results are summarized in Table 2.

TABLE 2optionally Formula 1c) and dimethyl carbonate was chopped with one of Formulae 2a to 2d>Chopping agent,YieldaBefore chopping-After chopping-TgState after 1State after 7HOAOHZ(OH)a (15 mol %)(%)Mn (Mw / Mn)bMn (Mw / Mn)b(° C.)cdaydaysExample 101a2a8169000 (1.62)2200 (1.81)−49WaxWaxExample 111a2b8643200 (1.58)2100 (1.96)−45WaxWaxExample 121a2c8549900 (1.54)2000 (1.84)−57WaxWaxExample 131a2d8250000 (1.61)1300 (1.71)−41WaxWaxExample 141a + 1c2a8153000 (1.43)2100 (1.85)−50TransparentWax(95:5)oilExample 151a + 1c2b8787000 (1.63)2200 (1.87)−48TransparentSuspended(95:5)oiloilExample 161a + 1c2c8450000 (1.72)1000 (1....

examples 22-35

Condensation of Formula 1a and One of Formulae 1b to 1h with DMC and Subsequent Chopping of the Condensation Product with Formula 2a

[0056]First step: 1,4-Butanediol (Formula 1a) and an additional diol selected from Formulae 1b to 1h were placed in a 3-neck flask such that the total number of moles was 111 mmol. The additional diol was used in the amount of 5 mol % or 10 mol %, as shown in Table 1. NaH (0.056 mmol, 0.05 mol %) was added to the flask to form HO(CH2)4O−Na+ and then 15.7 g (174 mmol) of dimethyl carbonate (DMC) was added thereto. The subsequent procedure was carried out in the same manner as in Examples 1-9.

[0057]Second step: The triol of Formula 2a as a chopping agent was added to the condensation product obtained in the first step. The chopping agent was used in an amount of 15 mol % (4.43 g, 16.7 mmol), based on the diols initially added. The reaction was carried out for 3 h while slowly cooling to 150° C. from 190° C. Within 10 min from the beginning of the reaction...

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Abstract

Provided is an aliphatic polycarbonate macropolyol including —OAO— and Z(O—)a as repeating units. In the aliphatic polycarbonate macropolyol, the repeating units —OAO— and Z(O—)a are linked to each other via carbonyl (—C(O)—) linkers or are bonded to hydrogen to form terminal —OH groups. The number of moles of the terminal —OH groups is from aZ to aZ+0.2Z (where Z represents the number of moles of the repeating unit Z(O—)a). Further provided is an aliphatic polycarbonate-co-aromatic polyester macropolyol including —OAO— and Z(O—)a as repeating units. In the aliphatic polycarbonate-co-aromatic polyester macropolyol, the repeating units —OAO— and Z(O—)a are linked via carbonyl (—C(O)—) and —C(O)YC(O)— as linkers or are bonded to hydrogen to form terminal —OH groups.

Description

TECHNICAL FIELD[0001]The present invention relates to an aliphatic polycarbonate macropolyol, an aliphatic polycarbonate-co-aromatic polyester macropolyol, and methods for producing the macropolyols. More specifically, the present invention relates to an aliphatic polycarbonate-co-aromatic polyester macropolyol that can be utilized as a polyurethane raw material, a coating material, a lubricating agent, etc., and a method for producing the macropolyol.BACKGROUND ART[0002]Aliphatic polycarbonates are biodegradable eco-friendly polymers. The most suitable process for the mass production of aliphatic polycarbonates is the condensation of dimethyl carbonate (DMC) with diols. DMC have been produced from toxic phosgene. Efforts have been made to develop processes for the production of DMC using carbon monoxide or more environmentally friendly carbon dioxide instead of phosgene. The use of carbon monoxide or carbon dioxide enables the production of DMC on a large scale at low cost. There a...

Claims

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Application Information

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IPC IPC(8): C08G64/02C08G63/78C08G63/64C08G64/30
CPCC08G64/0208C08G63/64C08G63/78C08G64/305C08G18/44C08G64/42C09D175/06C08G63/82C08G64/02
Inventor LEE, BUN YEOULJEON, JONG YEOBPARK, JI HAELEE, JUNG JAEHWANG, EUN YEONG
Owner LOTTE CHEM CORP
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