CN111423567A - Polymer compound and method for producing same - Google Patents
Polymer compound and method for producing same Download PDFInfo
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- CN111423567A CN111423567A CN202010022863.4A CN202010022863A CN111423567A CN 111423567 A CN111423567 A CN 111423567A CN 202010022863 A CN202010022863 A CN 202010022863A CN 111423567 A CN111423567 A CN 111423567A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/826—Metals not provided for in groups C08G63/83 - C08G63/86
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Provided are a polymer compound and a method for preparing the same. The polymer compound includes the following chemical formula 1, in the chemical formula 1, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms. The preparation method of the macromolecular compound comprises the following steps: polymerizing a phthalate compound having the following chemical formula 4 with a diol compound having the following chemical formula 5 to produce a first polymer compound; and subjecting the first polymer compound to a polymerization reaction with a dicarboxylic acid compound having the following chemical formula 6 to produce a second polymer compound, wherein the second polymer compound is polymerizedIn chemical formulas 4 to 6, Ar represents a benzene ring, R1And R2Represents an alkyl group having 1 to 9 carbon atoms, and A and B each represents a hydrocarbon group having 2 to 9 carbon atoms. The polymer compound of the embodiment of the present invention may have excellent adhesiveness. For example, the polymer compound may have excellent hot-melt adhesiveness. [ chemical formula 1]
Description
Technical Field
The invention relates to a high molecular compound and a preparation method thereof.
Background
Various high molecular substances are known for use as binders. However, the conventional adhesive polymer cannot satisfy precise and uniform adhesion required in various technical fields and in the production processes of various products in recent years.
Disclosure of Invention
Technical problem to be solved by the invention
In order to solve the above problems, the present invention provides a polymer compound having excellent adhesiveness.
The invention provides a preparation method of the high molecular compound.
Other objects of the present invention will become apparent from the detailed description below.
Means for solving the problems
The polymer compound according to the embodiment of the present invention includes the following chemical formula 1,
[ chemical formula 1]
In the chemical formula 1, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms.
The method for producing a polymer compound according to an embodiment of the present invention includes the steps of: polymerizing a phthalate compound having the following chemical formula 4 with a diol compound having the following chemical formula 5 to produce a first polymer compound; and subjecting the first polymeric compound to a polymerization reaction with a dicarboxylic acid compound having the following chemical formula 6 to generate a second polymeric compound.
[ chemical formula 4]
R1OOC-Ar-COOR2
[ chemical formula 5]
HO-A-OH
[ chemical formula 6]
HOOC-B-COOH
In the chemical formulas 4 to 6, Ar represents a benzene ring, R1And R2Represents a carbon number of 1 to 9A and B each represent a hydrocarbon group having 2 to 9 carbon atoms.
Effects of the invention
The polymer compound of the embodiment of the present invention may have excellent adhesiveness. For example, the polymer compound may have excellent hot-melt adhesiveness.
Detailed Description
The present invention will be described in detail below with reference to examples. The objects, features and advantages of the present invention will be readily understood by the following examples. The present invention is not limited to the embodiments described herein, and may be embodied in other forms. The embodiments described herein are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art. Therefore, the present invention should not be limited by the following examples.
Although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish the elements from each other.
[ Polymer Compound ]
The polymer compound according to the embodiment of the present invention includes the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms.
In the chemical formula 1, -Ar-may represent
And
at least any one of them. Preferably, the polymer compound may contain both
And
in the polymer compound, when
Relative to the content of
When the amount is increased, the adhesion of the polymer compound is increased, but the melting point is lowered. Therefore, it can be determined in consideration of the adhesive force and melting point of the polymer compound
And
the content of (a).
And
the ratio of (A) to (B) may be 1:1 to 10: 1. Preferably, the first and second electrodes are formed of a metal,
and
the ratio of (A) to (B) may be 3:1 to 7: 1.
In the chemical formula 1, -A-may represent- (CH)2)a- (a is an integer of 2 to 9). For example, -A-may represent- (CH)2)2-、-(CH2)3-and- (CH)2)4-at least any one of. -B-may represent- (CH)2)b- (b is an integer of 2 to 9). For example, -B-may represent- (C H)2)2-and- (CH)2)4-at least any one of.
In the chemical formula 1, the molecular weight of the moiety of the following chemical formula 3 may be 1000 to 10000.
[ chemical formula 3]
The molecular weight of the polymer compound may be 100000 to 200000.
The polymer compound may have excellent adhesiveness. For example, the polymer compound may have excellent hot melt adhesiveness. The polymer compound may be used alone as a binder or in a mixture with other polymer compounds. For example, the polymer compound may be used as a hot melt adhesive, or may be used in a resin composition including an adhesive component.
[ Process for producing Polymer Compound ]
The method for preparing a polymer compound according to an embodiment of the present invention includes the steps of: subjecting a phthalate compound having the following chemical formula 4 and a diol compound having the following chemical formula 5 to a polymerization reaction (first polymerization reaction) to produce a first polymer compound; and subjecting the first polymer compound to a polymerization reaction (second polymerization reaction) with a dicarboxylic acid compound having the following chemical formula 6 to produce a second polymer compound.
[ chemical formula 4]
R1OOC-Ar-COOR2
[ chemical formula 5]
HO-A-OH
[ chemical formula 6]
HOOC-B-COOH
In the chemical formulas 4 to 6, Ar represents a benzene ring, R1And R2Represents an alkyl group having 1 to 9 carbon atoms, and A and B each represents a hydrocarbon group having 2 to 9 carbon atoms.
The method for producing a polymer compound further includes a step of performing a polymerization reaction (third polymerization reaction) for increasing the molecular weight of the second polymer compound.
In the chemical formulae 4 to 6, -Ar-may represent
And
at least any one of them. -A-may represent- (CH)2)a- (a is an integer of 2 to 9). For example, -A-may represent- (CH)2)2-、-(CH2)3-and- (CH)2)4-at least any one of. -B-may represent- (CH)2)b- (b is an integer of 2 to 9). For example, -B-may represent- (CH)2)2-and- (CH)2)4-at least one of.
The phthalate compound may comprise at least any one of a terephthalate compound and an isophthalate compound. Preferably, the phthalate compound may comprise both a terephthalate compound and an isophthalate compound. When the amount of the isophthalate compound is increased relative to the terephthalate compound, the adhesion of the resulting polymer compound increases, but the melting point decreases. Therefore, the amounts of the terephthalate compound and the isophthalate compound may be determined in consideration of the adhesive force and the melting point of the polymer compound. The molar ratio of the terephthalate compound to the isophthalate compound may be 1:1 to 10: 1. Preferably, the molar ratio of the terephthalate compound to the isophthalate compound may be 3:1 to 7: 1.
The phthalate compound may comprise at least any one of dimethyl terephthalate and dimethyl isophthalate. Preferably, the phthalate compound may comprise both dimethyl terephthalate and dimethyl isophthalate. The diol compound may include at least any one of ethylene glycol, propylene glycol, and butylene glycol. The dicarboxylic acid compound may include at least any one of succinic acid and adipic acid.
The diol compound is preferably added in an amount greater than the number of moles of the phthalate compound reacted so that no unreacted phthalate compound remains.
The first polymeric compound may have the following chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, Ar represents a benzene ring, and a represents a hydrocarbon group having 2 to 9 carbon atoms. -Ar-may represent
And
at least any one of them. -A-may represent- (CH)2)a- (a is an integer of 2 to 9). For example, -A-may represent- (CH)2)2-、-(CH2)3-and- (CH)2)4-at least any one of.
The first polymeric compound may include the following chemical formula 3, and the second polymeric compound may include the following chemical formula 1.
[ chemical formula 3]
[ chemical formula 1]
In the chemical formulas 1 and 3, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms. -Ar-may represent
And
at least any ofOne kind of the medicine. -A-may represent- (CH)2)a- (a is an integer of 2 to 9). For example, -A-may represent- (CH)2)2-、-(CH2)3-and- (CH)2)4-at least any one of. -B-may represent- (CH)2)b- (b is an integer of 2 to 9). For example, -B-may represent- (CH)2)2-and- (CH)2)4-at least any one of.
The step of forming the first polymeric compound may include the step of mixing the phthalate compound and the diol compound with a first catalyst, which may comprise Tetra-n-butyl titanate (TNBT).
The step of forming the second polymeric compound may include the step of mixing the first polymeric compound and the dicarboxylic acid compound with a second catalyst, which may include TNBT and triphenyl phosphate (TPP).
The step of performing polymerization for increasing the molecular weight of the second polymeric compound may include the step of mixing the second polymeric compound with a third catalyst, which may include T NBT, Zinc Acetate (ZA), and Trimethylphosphine (TMP).
The first to third polymerization reactions may be performed at 180 to 250 ℃. For example, the first polymerization reaction and the second polymerization reaction may be performed at 190 ℃, and the third polymerization reaction may be performed at 220 ℃. Also, the third polymerization reaction may be performed at 190 ℃ and then changed to be performed at 220 ℃.
The molecular weight of the first polymer compound may be 1000 to 10000, the molecular weight of the second polymer compound may be 10000 to 100000, and the molecular weight of the polymer compound may be 100000 to 200000.
[ preparation of Polymer Compound ]
The reactants 1, 4-butanediol, dimethyl terephthalate and dimethyl isophthalate and TNBT (Tetran-butyltantalate, TNBT) as a catalyst were sequentially added to the reactor. The dimethyl terephthalate and the dimethyl isophthalate were added at a molar ratio of 5: 1. The 1, 4-butanediol is preferably added in an amount greater than the number of moles of reacting with the dimethyl terephthalate and the dimethyl isophthalate so that no unreacted reactants of the dimethyl terephthalate and the dimethyl isophthalate remain. For example, 17.48kg and 3.5kg of the dimethyl terephthalate and 3.5kg of the dimethyl isophthalate were added, respectively, and 21.9kg of the 1, 4-butanediol was added. 27g of tetra-n-butyl titanate was added. The temperature of the reactor was set at 190 ℃ before the reactants and the catalyst were added.
The agitator in the reactor was started and the speed of the agitator was gradually increased to 100 rpm. The reactants undergo a polymerization reaction (first polymerization reaction) by the catalyst, and a first polymeric compound having the following chemical formula 7 is produced.
[ chemical formula 7]
In the chemical formula 7, -Ar-represents
And
the first polymeric compound includes the following chemical formula 8.
[ chemical formula 8]
In the chemical formula 8, -Ar-represents
And
the first polymeric compound may be an oligomer having a molecular weight of 1000 to 10000. The first polymer compound may be in a transparent liquid state at 190 ℃.
The reactants react to form the first polymeric compound while producing methanol. The methanol produced is discharged through a column connected to the top of the reactor. The amount of methanol discharged was confirmed by the column. The termination of the polymerization reaction can be determined by the amount of methanol removed and/or the temperature of the column.
After the polymerization reaction was terminated, adipic acid as a reactant and TPP (triphenylphoshate) and TNBT as a catalyst were sequentially added to the reactor, 10.52 kg of the adipic acid was added, 18g of the TPP was added, and 38g of the TNBT was added.
The agitator in the reactor was started and the speed of the agitator was gradually increased to 100 rpm. The first polymeric compound and the adipic acid are subjected to a polymerization reaction (second polymerization reaction) by the catalyst to generate a second polymeric compound comprising the following chemical formula 9.
[ chemical formula 9]
In the chemical formula 9, -Ar-represents
And
the second polymeric compound may have a molecular weight of 10000 to 100000.
Water is produced at the same time that the first polymeric compound and the adipic acid react to form the second polymeric compound. The produced water is discharged through a column connected to the top of the reactor. The discharge amount of the water can be confirmed by the column. The termination of the polymerization reaction can be determined by the amount of water removed and/or the temperature of the column.
After the polymerization reaction is terminated, za (zincate), tmp (trimethyphosphine) and TNBT are sequentially added as catalysts to the reactor. 18g of ZA, 25g of TMP and 38g of TNBT.
The agitator in the reactor was started and the speed of the agitator was gradually increased to 100 rpm. The second polymer compound undergoes a polymerization reaction (third polymerization reaction) by the catalyst, and the molecular weight increases, thereby producing a polymer compound. The polymer compound may include the chemical formula 9, and has a molecular weight of 100000 to 200000.
The molecular weight and melt index (MFI) of the polymer compound can be controlled by adjusting the rotation speed of the stirrer. For example, after the rotational speed of the agitator is decreased from 100rpm to 15rpm, it is increased to 35rpm and maintained, and then gradually increased to 95 rpm. Also, the temperature of the reactor may be changed from 190 ℃ to 220 ℃.
Unlike the preparation examples, the third polymerization reaction can be completed in an additional reactor. After 10 minutes from the addition of the catalyst to the reactor (first reactor), when the third polymerization reaction was stabilized, the mixture in the first reactor was transferred to another reactor (second reactor) connected to the first reactor. At this time, the rotation speed of the stirrer in the first reactor was reduced from 100rpm to 15 rpm. Before the mixture was transferred, unnecessary gas and the like in the second reactor were removed by a vacuum pump, and the temperature of the second reactor was set to 220 ℃. The molecular weight and MFI (melt flow index) of the polymer compound can be controlled by adjusting the rotation speed of the stirrer in the second reactor. For example, the rotational speed of the stirrer within the second reactor was maintained at 35rpm and gradually increased to 95rpm as the mixture was transferred to the second reactor.
Thus, specific embodiments of the present invention have been described. It will be appreciated by those skilled in the art that the present invention may be embodied in modified forms without departing from the essential characteristics thereof. Accordingly, the disclosed embodiments are to be considered in all respects only as illustrative and not restrictive. The scope of the invention is indicated in the claims, rather than the foregoing description, and all differences within the equivalent scope thereof should be construed as being included in the present invention.
Claims (18)
1. A polymer compound characterized by containing, as a main component,
comprising the following chemical formula 1,
[ chemical formula 1]
In the chemical formula 1, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms.
2. A polymer compound according to claim 1,
in the chemical formula 1, the first and second organic solvents,
-Ar-represents
And
at least one of the above-mentioned (a) and (b),
-A-represents- (CH)2)aWherein a is an integer of 2 to 9 inclusive,
-B-represents- (CH)2)b-, wherein b is an integer of 2 to 9.
3. A polymer compound according to claim 2,
4. A polymer compound according to claim 2,
-A-represents- (CH)2)2-、-(CH2)3-and- (CH)2)4At least any one of (a) to (b),
-B-represents- (CH)2)2-and- (CH)2)4-at least any one of.
5. A polymer compound according to claim 1,
in the chemical formula 1, the moiety of the following chemical formula 3 has a molecular weight of 1000 to 10000,
[ chemical formula 3]
6. A polymer compound according to claim 1,
the molecular weight of the high molecular compound is 100000-200000.
7. A polymer compound according to claim 1,
the polymer compound has hot-melt adhesiveness.
8. A method for producing a polymer compound, comprising the steps of:
polymerizing a phthalate compound having the following chemical formula 4 with a diol compound having the following chemical formula 5 to produce a first polymer compound; and
polymerizing the first polymeric compound with a dicarboxylic acid compound having the following chemical formula 6 to generate a second polymeric compound,
[ chemical formula 4]
R1OOC-Ar-COOR2
[ chemical formula 5]
HO-A-OH
[ chemical formula 6]
HOOC-B-COOH
In the chemical formulas 4 to 6, Ar represents a benzene ring, R1And R2Represents an alkyl group having 1 to 9 carbon atoms, and A and B each represents a hydrocarbon group having 2 to 9 carbon atoms.
9. A method for producing a polymer compound according to claim 8,
in the chemical formulae 4 to 6,
-Ar-represents
And
at least one of the above-mentioned (a) and (b),
-A-represents- (CH)2)aWherein a is an integer of 2 to 9 inclusive,
-B-represents- (CH)2)b-, wherein b is an integer of 2 to 9.
10. A method for producing a polymer compound according to claim 8,
the phthalate compound comprises a terephthalate compound and an isophthalate compound,
the molar ratio of the terephthalate compound to the isophthalate compound is 1: 1-10: 1.
11. A method for producing a polymer compound according to claim 8,
the first polymer compound has the following chemical formula 2,
[ chemical formula 2]
In the chemical formula 2, Ar represents a benzene ring, and a represents a hydrocarbon group having 2 to 9 carbon atoms.
12. A method for producing a polymer compound according to claim 8,
the first polymeric compound includes the following chemical formula 3,
the second polymer compound includes the following chemical formula 1,
[ chemical formula 3]
[ chemical formula 1]
In the chemical formulas 1 and 3, Ar represents a benzene ring, and A and B each represent a hydrocarbon group having 2 to 9 carbon atoms.
13. A method for producing a polymer compound according to claim 8,
the phthalate compound comprises at least one of dimethyl terephthalate and dimethyl isophthalate,
the diol compound contains at least one of ethylene glycol, propylene glycol, and butylene glycol,
the dicarboxylic acid compound comprises at least any one of succinic acid and adipic acid.
14. A method for producing a polymer compound according to claim 8,
the step of forming the first polymeric compound comprises:
a step of mixing the phthalate compound and the glycol compound with a first catalyst,
the first catalyst comprises TNBT.
15. A method for producing a polymer compound according to claim 8,
the step of generating the second polymeric compound comprises:
a step of mixing the first polymerization compound and the dicarboxylic acid compound with a second catalyst,
the second catalyst comprises TNBT and TPP.
16. The method for producing a polymer compound according to claim 8, further comprising a step of performing a polymerization reaction for increasing the molecular weight of the second polymer compound.
17. The method for producing a polymer compound according to claim 16, wherein the step of performing a polymerization reaction for increasing the molecular weight of the second polymer compound comprises,
a step of mixing the second polymer compound and a third catalyst,
the third catalyst comprises TNBT, ZA, and TMP.
18. A method for producing a polymer compound according to claim 16,
the first polymeric compound has a molecular weight of 1000 to 10000,
the molecular weight of the second polymer compound is 10000-100000,
the molecular weight of the high molecular compound is 100000-200000.
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| KR10-2019-0003241 | 2019-01-10 | ||
| KR1020190003241A KR102186639B1 (en) | 2019-01-10 | 2019-01-10 | Phthalate based polymer and method of manufacturing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101245230A (en) * | 2008-02-21 | 2008-08-20 | 上海天洋热熔胶有限公司 | Method for manufacturing linear copolyester hot melt adhesive |
| US20090227735A1 (en) * | 2008-03-07 | 2009-09-10 | Eastman Chemical Company | Miscible polyester blends and shrinkable films prepared therefrom |
| CN103987756A (en) * | 2011-12-19 | 2014-08-13 | 赢创工业集团股份有限公司 | Method for producing polyesters |
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| KR100366484B1 (en) * | 1999-12-11 | 2003-01-14 | 주식회사 이래화학 | Copolyester resin composition and a process of preparation thereof |
| KR20100082077A (en) * | 2009-01-08 | 2010-07-16 | 홍창일 | Adhisive resins for coating of steel plate |
| KR101068030B1 (en) * | 2011-06-03 | 2011-09-28 | 주식회사 지오솔테크 | Hydrolysis resistant and biodegradable aliphatic/aromatic copolyester resin composition |
| KR101464597B1 (en) * | 2012-08-31 | 2014-11-24 | 도레이케미칼 주식회사 | Heat-resistant Co-Polymerization Polyester and Preparing thereof |
| KR101637994B1 (en) * | 2016-01-18 | 2016-07-08 | 주식회사 수연 | Aromatic/aliphatic copolyester resin composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101245230A (en) * | 2008-02-21 | 2008-08-20 | 上海天洋热熔胶有限公司 | Method for manufacturing linear copolyester hot melt adhesive |
| US20090227735A1 (en) * | 2008-03-07 | 2009-09-10 | Eastman Chemical Company | Miscible polyester blends and shrinkable films prepared therefrom |
| CN103987756A (en) * | 2011-12-19 | 2014-08-13 | 赢创工业集团股份有限公司 | Method for producing polyesters |
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Application publication date: 20200717 |