CN106318305B - Preparation method of polyester hot melt adhesive for film making - Google Patents
Preparation method of polyester hot melt adhesive for film making Download PDFInfo
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- CN106318305B CN106318305B CN201610756738.XA CN201610756738A CN106318305B CN 106318305 B CN106318305 B CN 106318305B CN 201610756738 A CN201610756738 A CN 201610756738A CN 106318305 B CN106318305 B CN 106318305B
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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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- 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
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J7/00—Adhesives in the form of films or foils
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The polyester hot melt adhesive for film making and the preparation method thereof are characterized in that the polyester hot melt adhesive for film making comprises the following raw materials: dibasic acid consisting of a mixture of adipic acid, succinic acid, dodecanedioic acid and tridecanedioic acid, dihydric alcohol consisting of a mixture of 1, 4-butanediol and 1, 4-cyclohexanedimethanol, 1,2, 4-trimellitic anhydride, a catalyst and an antioxidant. The dibasic acids used in the invention are aliphatic acids, and the polyester hot melt adhesive product suitable for film making is finally synthesized by setting the proportion of the raw materials and adding a specific amount of 1,2, 4-trimellitic anhydride. The curing time of the polyester hot melt adhesive product prepared by the invention is obviously shortened, the Shore hardness is also obviously reduced, the transverse and longitudinal tensile strength of the product is also obviously improved after the product is made into a net film, and the market demand is met.
Description
Technical Field
The invention relates to a preparation method of a polyester hot melt adhesive, in particular to a preparation method of a polyester hot melt adhesive for film making.
Background
The net film-shaped hot melt adhesive is favored by hot melt compounding in the automobile industry due to the unique grid shape, low volatility and excellent bonding performance.
However, the curing time of the polyester for producing the net film-shaped hot melt adhesive is generally 120-180 s, and the curing time is long, so that the speed of net film production is slow, and the production efficiency is influenced; meanwhile, the Shore hardness of the existing polyester hot melt adhesive is high and is generally over 45HD, so that the flexibility of the prepared net-shaped hot melt adhesive product is relatively low; in addition, after the conventional polyester hot melt adhesive is produced and formed in a net film shape, the transverse and longitudinal tensile strength of the conventional polyester hot melt adhesive is lower, generally lower than 6N/cm, and the conventional polyester hot melt adhesive is easy to tear, so that the bonding effect of the net film hot melt adhesive product in practical application is influenced.
Therefore, how to prepare a polyester hot melt adhesive product with short curing time, low hardness and high transverse and longitudinal tensile strength after film preparation so as to better meet market demands becomes a problem to be solved.
Disclosure of Invention
The invention aims to solve the technical problems and provides a preparation method of a polyester hot melt adhesive for film production.
The technical scheme adopted by the invention is as follows: the polyester hot melt adhesive for film production comprises the following raw materials: dibasic acid consisting of a mixture of adipic acid, succinic acid, dodecanedioic acid and tridecanedioic acid, dihydric alcohol consisting of a mixture of 1, 4-butanediol and 1, 4-cyclohexanedimethanol, 1,2, 4-trimellitic anhydride, a catalyst and an antioxidant;
wherein the proportion of each raw material is as follows:
dibasic acid: the molar ratio of the dihydric alcohol is 1: 1.6;
adipic acid: succinic acid: dodecanedioic acid: the molar ratio of the tridecanoic acid is 1: 0.3-0.45: 0.1-0.3: 0.2 to 0.40;
1, 4-butanediol: the molar ratio of the 1, 4-cyclohexanedimethanol is 1: 0.68-0.85;
the addition amount of the 1,2, 4-trimellitic anhydride is 0.01 to 0.07 percent of the total mass of the dibasic acid;
the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.06-0.09% of the total mass of the dibasic acid;
the antioxidant is tris (2, 4-di-tert-butylphenyl) phosphite, and the addition amount thereof is 0.05-0.1% of the total mass of the dibasic acid.
A preparation method of polyester hot melt adhesive for film production comprises the following steps:
(1) adding dibasic acid consisting of a mixture of adipic acid, succinic acid, dodecanedioic acid and tridecanedioic acid, dihydric alcohol consisting of a mixture of 1, 4-butanediol and 1, 4-cyclohexanedimethanol, 1,2, 4-trimellitic anhydride and a catalyst into an esterification kettle according to a preset proportion for esterification reaction at the reaction temperature of 135-230 ℃, and finishing the esterification reaction when the distilled water amount of the esterification reaction is more than 97% of the theoretical water yield;
(2) adding a certain amount of antioxidant into the product obtained in the step (1), performing reduced pressure polycondensation reaction for 1.0h at the temperature of 240-245 ℃ and under the pressure of 40-45 Pa, finishing the polycondensation reaction, introducing nitrogen, relieving vacuum, and discharging while hot to obtain a polyester hot melt adhesive product for film making;
in the step (1), the molar ratio of each material is as follows:
dibasic acid: 1:1.6 of dihydric alcohol;
adipic acid: succinic acid: dodecanedioic acid: 1 of tridecanedioic acid: 0.3-0.45: 0.1-0.3: 0.2 to 0.40;
1, 4-butanediol: 1, 4-cyclohexanedimethanol is 1: 0.68-0.85;
the addition amount of the 1,2, 4-trimellitic anhydride is 0.01 to 0.07 percent of the total mass of the dibasic acid;
the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.06-0.09% of the total mass of the dibasic acid;
in the step (2), the antioxidant is tris (2, 4-di-tert-butylphenyl) phosphite, and the addition amount thereof is 0.05-0.1% of the total mass of the dibasic acid.
The innovation of the invention is that: aliphatic acid is selected as the dibasic acid, and a certain amount of 1,2, 4-trimellitic anhydride is added by setting the proportion of the raw materials to finally synthesize the polyester hot melt adhesive product suitable for film preparation. The curing time of the polyester hot melt adhesive product prepared by the invention is obviously shortened, the Shore hardness is also obviously reduced, the transverse and longitudinal tensile strength of the product is also obviously improved after the product is made into a net film, and the market demand is met.
Detailed Description
The present invention will be further illustrated by the following examples, but is not limited thereto.
Example 1
The polyester hot melt adhesive for film making comprises the following raw materials: 146.0000g (1.0000mol) of adipic acid, 35.4000g (0.3000mol) of succinic acid, 61.0000g (0.2500mol) of tridecanedioic acid, 23.0000g (0.1000mol) of dodecanedioic acid, 135.0000g (1.5000mol) of 1, 4-butanediol, 164.1600g (1.1400mol) of 1, 4-cyclohexanedimethanol, 0.1592g of tetrabutyl titanate, 0.0260g of 1,2, 4-trimellitic anhydride and 0.1592g of tris (2, 4-di-tert-butylphenyl) phosphite.
The preparation method of the polyester hot melt adhesive for film production comprises the following steps:
(1) adding dibasic acid, dihydric alcohol, tetrabutyl titanate and 1,2, 4-trimellitic anhydride into a 1L reaction kettle, gradually heating to 100 ℃, starting stirring, distilling off water when the temperature is close to 135 ℃, keeping the distillation temperature at 98-102 ℃, continuously heating to about 230 ℃, and finishing the esterification reaction when the water yield reaches more than 97% of the theoretical value;
(2) adding tris (2, 4-di-tert-butylphenyl) phosphite to carry out a reduced pressure polycondensation reaction, gradually increasing the temperature to 240 ℃, and keeping the temperature; and (3) gradually reducing the pressure in the reaction kettle to 40Pa, maintaining for 1.0 hour, completing polycondensation, introducing nitrogen, relieving vacuum, and discharging when the reaction kettle is hot to obtain the polyester hot melt adhesive product for film making.
The polyester hot melt adhesive for film formation prepared in example 1 was measured to have a DSC melting point of 97 ℃, a curing time of 76s, and a shore hardness of 24HD, and after the film hot melt adhesive was formed, the transverse and longitudinal tensile strengths were measured to be 13.4N/cm and 14.0N/cm, respectively.
Example 2
The polyester hot melt adhesive for film making comprises the following raw materials: 146.0000g (1.0000mol) of adipic acid, 41.3000g (0.3500mol) of succinic acid, 48.8000g (0.2000mol) of tridecanedioic acid, 69.0000g (0.3000mol) of dodecanedioic acid, 144.0000g (1.6000mol) of butanediol, 195.8400g (1.3600mol) of 1, 4-cyclohexanedimethanol, 0.2136g of tetrabutyl titanate, 0.0920g of 1,2, 4-trimellitic anhydride and 0.1526g of tris (2, 4-di-tert-butylphenyl) phosphite.
The preparation method of the polyester hot melt adhesive for film production comprises the following steps:
(1) adding dibasic acid, dihydric alcohol, tetrabutyl titanate and 1,2, 4-trimellitic anhydride into a 1L reaction kettle, gradually heating to 100 ℃, starting stirring, distilling off water when the temperature is close to 135 ℃, keeping the distillation temperature at 98-102 ℃, continuously heating to about 230 ℃, and finishing the esterification reaction when the water yield reaches more than 97% of the theoretical value;
(2) adding tris (2, 4-di-tert-butylphenyl) phosphite to carry out a reduced pressure polycondensation reaction, gradually increasing the temperature to 245 ℃, and keeping the temperature; and (3) gradually reducing the pressure in the reaction kettle to 45Pa, maintaining for 1.0 hour, completing polycondensation, introducing nitrogen, relieving vacuum, and discharging when the reaction kettle is hot to obtain the polyester hot melt adhesive product for film making.
The polyester hot melt adhesive for film formation prepared in example 2 was measured to have a DSC melting point of 95 ℃, a curing time of 63s, and a shore hardness of 25HD, and after the film hot melt adhesive was formed, the transverse and longitudinal tensile strengths were measured to be 14.3N/cm and 14.1N/cm, respectively.
Example 3
The polyester hot melt adhesive for film making comprises the following raw materials: 146.0000g (1.0000mol) of adipic acid, 47.2000g (0.4000mol) of succinic acid, 73.2000g (0.3000mol) of tridecanedioic acid, 46.0000g (0.2000mol) of dodecanedioic acid, 153.0000g (1.7000mol) of butanediol, 192.9600g (1.3400mol) of 1, 4-cyclohexanedimethanol, 0.2450g of tetrabutyl titanate, 0.1562g of 1,2, 4-trimellitic anhydride and 0.2343g of tris (2, 4-di-tert-butylphenyl) phosphite.
The preparation method of the polyester hot melt adhesive for film production comprises the following steps:
(1) adding dibasic acid, dihydric alcohol, tetrabutyl titanate and 1,2, 4-trimellitic anhydride into a 1L reaction kettle, gradually heating to 100 ℃, starting stirring, distilling off water when the temperature is close to 135 ℃, keeping the distillation temperature at 98-102 ℃, continuously heating to about 230 ℃, and finishing the esterification reaction when the water yield reaches more than 97% of the theoretical value;
(2) adding tris (2, 4-di-tert-butylphenyl) phosphite to carry out a reduced pressure polycondensation reaction, gradually increasing the temperature to 240 ℃, and keeping the temperature; and (3) gradually reducing the pressure in the reaction kettle to 45Pa, maintaining for 1.0 hour, completing polycondensation, introducing nitrogen, relieving vacuum, and discharging when the reaction kettle is hot to obtain the polyester hot melt adhesive product for film making.
The polyester hot melt adhesive for film formation prepared in example 3 was measured to have a DSC melting point of 100 ℃, a curing time of 55s, and a shore hardness of 20HD, and after the film hot melt adhesive was formed, the transverse and longitudinal tensile strengths thereof were measured to be 15.7N/cm and 15.2N/cm, respectively.
Example 4
The polyester hot melt adhesive for film making comprises the following raw materials: 146.0000g (1.0000mol) of adipic acid, 53.1000g (0.4500mol) of succinic acid, 97.6000g (0.4000mol) of tridecanedioic acid, 57.5000g (0.2500mol) of dodecanedioic acid, 180.0000g (2.0000mol) of butanediol, 195.8400g (1.3600mol) of 1, 4-cyclohexanedimethanol, 0.3187g of tetrabutyl titanate, 0.2479g of 1,2, 4-trimellitic anhydride and 0.1592g of tris (2, 4-di-tert-butylphenyl) phosphite.
The preparation method of the polyester hot melt adhesive for film production comprises the following steps:
(1) adding dibasic acid, dihydric alcohol, tetrabutyl titanate and 1,2, 4-trimellitic anhydride into a 1L reaction kettle, gradually heating to 100 ℃, starting stirring, distilling off water when the temperature is close to 135 ℃, keeping the distillation temperature at 98-102 ℃, continuously heating to about 230 ℃, and finishing the esterification reaction when the water yield reaches more than 97% of the theoretical value;
(2) adding tris (2, 4-di-tert-butylphenyl) phosphite to carry out a reduced pressure polycondensation reaction, gradually increasing the temperature to 245 ℃, and keeping the temperature; and (3) gradually reducing the pressure in the reaction kettle to 40Pa, maintaining for 1.0 hour, completing polycondensation, introducing nitrogen, relieving vacuum, and discharging when the reaction kettle is hot to obtain the polyester hot melt adhesive product for film making.
The polyester hot melt adhesive for film formation prepared in example 4 was measured to have a DSC melting point of 103 ℃, a curing time of 67s, and a shore hardness of 22HD, and after the film hot melt adhesive was prepared, the transverse and longitudinal tensile strengths were measured to be 14.7N/cm and 14.9N/cm, respectively.
When the products obtained in the above embodiments are subjected to performance tests, the melting point test refers to ISO 11357-.
Meanwhile, the inventors adjusted the addition amount of 1,2, 4-trimellitic anhydride with reference to the material ratios of the above examples 1 to 4. Tests show that under the condition that the mixture ratio of other raw materials is not changed, when the addition amount of the 1,2, 4-trimellitic anhydride is lower than a specified range, the polymerization reaction time is greatly prolonged to at least about 5.0h in the product synthesis process, and the curing time of the obtained product is also prolonged to more than 180 s; when the addition amount of the 1,2, 4-trimellitic anhydride exceeds the specified range, a crosslinking phenomenon will occur during the reaction, and the obtained product is an elastomer and has no adhesive property.
Therefore, the polyester hot melt adhesive product suitable for film making is finally synthesized by setting the mixture ratio of the raw materials, particularly the binary acid is aliphatic acid, and adding a specific amount of 1,2, 4-trimellitic anhydride. The polyester hot melt adhesive product prepared by the invention has a relatively low phase melting point of 95-103 ℃; the curing time is obviously shortened to 55-76 s; the Shore hardness is also obviously reduced to 20-25 HD; after the net film is manufactured, the transverse and longitudinal tensile strength of the net film is also obviously improved and is more than 13N/cm, and the market demand can be better met.
Claims (3)
1. The polyester hot melt adhesive for film production is characterized by comprising the following raw materials: dibasic acid consisting of a mixture of adipic acid, succinic acid, dodecanedioic acid and tridecanedioic acid, dihydric alcohol consisting of a mixture of 1, 4-butanediol and 1, 4-cyclohexanedimethanol, 1,2, 4-trimellitic anhydride, a catalyst and an antioxidant;
wherein the raw materials are respectively in the following proportions:
dibasic acid: the molar ratio of the dihydric alcohol is 1: 1.6;
adipic acid: succinic acid: dodecanedioic acid: the molar ratio of the tridecanoic acid is 1: 0.3-0.45: 0.1-0.3: 0.2 to 0.40;
1, 4-butanediol: the molar ratio of the 1, 4-cyclohexanedimethanol is 1: 0.68-0.85;
the addition amount of the 1,2, 4-trimellitic anhydride is 0.01 to 0.07 percent of the total mass of the dibasic acid;
the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.06% -0.09% of the total mass of the dibasic acid.
2. The polyester hot melt adhesive for film production according to claim 1, wherein the antioxidant is tris (2, 4-di-tert-butylphenyl) phosphite, and the amount thereof added is 0.05% to 0.1% of the total mass of the dibasic acid.
3. A preparation method of polyester hot melt adhesive for film production is characterized by comprising the following steps:
(1) adding dibasic acid consisting of a mixture of adipic acid, succinic acid, dodecanedioic acid and tridecanedioic acid, dihydric alcohol consisting of a mixture of 1, 4-butanediol and 1, 4-cyclohexanedimethanol, 1,2, 4-trimellitic anhydride and a catalyst into an esterification kettle according to a preset proportion for esterification reaction at the reaction temperature of 135-230 ℃, and finishing the esterification reaction when the distilled water amount of the esterification reaction is more than 97% of the theoretical water yield;
(2) adding a certain amount of antioxidant into the product obtained in the step (1), performing reduced pressure polycondensation reaction for 1.0h at the temperature of 240-245 ℃ and under the pressure of 40-45 Pa, finishing the polycondensation reaction, introducing nitrogen, relieving vacuum, and discharging while hot to obtain a polyester hot melt adhesive product for film making;
in the step (1), the mixture ratio of each material is as follows:
dibasic acid: the molar ratio of the dihydric alcohol is 1: 1.6;
adipic acid: succinic acid: dodecanedioic acid: the molar ratio of the tridecanoic acid is 1: 0.3-0.45: 0.1-0.3: 0.2 to 0.40;
1, 4-butanediol: the molar ratio of the 1, 4-cyclohexanedimethanol is 1: 0.68-0.85;
the addition amount of the 1,2, 4-trimellitic anhydride is 0.01-0.07% of the total mass of the dibasic acid;
the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.06% -0.09% of the total mass of the dibasic acid;
in the step (2), the antioxidant is tris (2, 4-di-tert-butylphenyl) phosphite, and the addition amount thereof is 0.05-0.1% of the total mass of the dibasic acid.
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| CN106928406B (en) * | 2017-03-20 | 2019-06-18 | 苏州长业材料技术有限公司 | A kind of adhesive polyester of adjustable viscosity and preparation method thereof |
| CN114685767A (en) * | 2020-12-31 | 2022-07-01 | 中国石油化工股份有限公司 | Polyester for adhesive, preparation method and use method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255443B1 (en) * | 1998-07-13 | 2001-07-03 | Ems Chemie Ag | Low-melting copolyester and copolyetherester hot-melt adhesives |
| CN101805578A (en) * | 2010-03-19 | 2010-08-18 | 苏州赛伍应用技术有限公司 | Polyester resin adhesive and use thereof in preparation of back protection film of solar cell |
| CN103468195A (en) * | 2013-09-26 | 2013-12-25 | 上海天洋热熔胶有限公司 | Preparation method of biodegradable polyester hot melt adhesive |
| CN104119829A (en) * | 2014-07-22 | 2014-10-29 | 昆山天洋热熔胶有限公司 | Preparation method of polyester hot melt adhesive with high viscosity and locally sensitive viscosity-temperature characteristics |
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2016
- 2016-08-30 CN CN201610756738.XA patent/CN106318305B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255443B1 (en) * | 1998-07-13 | 2001-07-03 | Ems Chemie Ag | Low-melting copolyester and copolyetherester hot-melt adhesives |
| CN101805578A (en) * | 2010-03-19 | 2010-08-18 | 苏州赛伍应用技术有限公司 | Polyester resin adhesive and use thereof in preparation of back protection film of solar cell |
| CN103468195A (en) * | 2013-09-26 | 2013-12-25 | 上海天洋热熔胶有限公司 | Preparation method of biodegradable polyester hot melt adhesive |
| CN104119829A (en) * | 2014-07-22 | 2014-10-29 | 昆山天洋热熔胶有限公司 | Preparation method of polyester hot melt adhesive with high viscosity and locally sensitive viscosity-temperature characteristics |
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Address after: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee after: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee after: Kunshan Tianyang New Material Co.,Ltd. Address before: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. |
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Address after: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee after: Tianyang New Material (Shanghai) Technology Co.,Ltd. Patentee after: Kunshan Tianyang New Material Co.,Ltd. Address before: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: Kunshan Tianyang New Material Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder |