KR101738356B1 - 에폭시 혹은 아크릴레이트기를 가지는 하이퍼브렌치드 폴리글리세롤을 포함하는 광경화형 조성물 및 이의 제조방법 - Google Patents
에폭시 혹은 아크릴레이트기를 가지는 하이퍼브렌치드 폴리글리세롤을 포함하는 광경화형 조성물 및 이의 제조방법 Download PDFInfo
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- KR101738356B1 KR101738356B1 KR1020160051792A KR20160051792A KR101738356B1 KR 101738356 B1 KR101738356 B1 KR 101738356B1 KR 1020160051792 A KR1020160051792 A KR 1020160051792A KR 20160051792 A KR20160051792 A KR 20160051792A KR 101738356 B1 KR101738356 B1 KR 101738356B1
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- hyperbranched polyglycerol
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- polyglycerol
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- 229920000223 polyglycerol Polymers 0.000 title claims abstract description 101
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 125000000524 functional group Chemical group 0.000 title claims description 30
- 239000004593 Epoxy Substances 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000011347 resin Substances 0.000 claims abstract description 30
- 229920005989 resin Polymers 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 14
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010146 3D printing Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000006735 epoxidation reaction Methods 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 239000011591 potassium Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 abstract description 17
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 230000009257 reactivity Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- REYHEHJHIFXNAL-UHFFFAOYSA-N butanoic acid;trifluoroborane Chemical compound FB(F)F.CCCC(O)=O REYHEHJHIFXNAL-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- -1 polymethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/24—Epihalohydrins
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
도 2는 아크릴레이트기가 도입된 하이퍼브렌치드 폴리글리세롤의 합성 결과로서 1H-NMR 데이터.
도 3은 적외선분광기 분석에 의한 레진의 경화거동을 보여주는 그래프.
Claims (6)
- 에폭시화 하이퍼브렌치드 폴리글리세롤의 아크릴레이트화 반응을 촉매 하에서 진행하여, 분자의 말단에 아래 화학식 1-1 또는 화학식 1-2로 표시되는 기능기, 아래 화학식 2-1 또는 화학식 2-2로 표시되는 기능기 또는 이들 모두를 포함하는 아크릴레이트화 하이퍼브렌치드 폴리글리세롤을 제조하는 아크릴레이트화단계;를 포함하여,
상기 아크릴레이트화 하이퍼브렌치드 폴리글리세롤을 포함하는 광경화형 하이퍼브렌치드 폴리글리세롤 조성물을 제조하는, 광경화형 하이퍼브렌치드 폴리글리세롤 조성물의 제조방법.
[화학식 1-1]
[화학식 1-2]
[화학식 2-1]
[화학식 2-2]
- 제1항에 있어서,
상기 아크릴레이트화 하이퍼브렌치드 폴리글리세롤은 25 ℃ 에서 점도가 800 cPs 이하인 액상이고, 광경화형 하이퍼브렌치드 폴리글리세롤 조성물의 제조방법.
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KR1020160051792A KR101738356B1 (ko) | 2016-04-27 | 2016-04-27 | 에폭시 혹은 아크릴레이트기를 가지는 하이퍼브렌치드 폴리글리세롤을 포함하는 광경화형 조성물 및 이의 제조방법 |
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KR1020160051792A KR101738356B1 (ko) | 2016-04-27 | 2016-04-27 | 에폭시 혹은 아크릴레이트기를 가지는 하이퍼브렌치드 폴리글리세롤을 포함하는 광경화형 조성물 및 이의 제조방법 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109777198A (zh) * | 2019-02-13 | 2019-05-21 | 新昌县高纤纺织有限公司 | 环保可溶性油墨及其制备工艺 |
KR20190142569A (ko) * | 2018-06-18 | 2019-12-27 | 숭실대학교산학협력단 | 폴리락틱산 강인화제용 조성물, 이를 통해 제조된 강인화성 폴리락틱산 공중합체 및 이의 제조방법 |
US20200291253A1 (en) * | 2019-03-12 | 2020-09-17 | Unist(Ulsan National Institute Of Science And Technology) | Ink composition for bioprinting and hydrogel formed from the same |
CN114149565A (zh) * | 2021-11-30 | 2022-03-08 | 江苏三木化工股份有限公司 | 一种可光固化的超支化聚氨酯-环氧丙烯酸酯的制备方法 |
WO2023128570A1 (ko) * | 2021-12-30 | 2023-07-06 | 주식회사 아이센스 | 고분자 재료의 표면 처리용 조성물, 키트 및 표면 처리 방법 |
-
2016
- 2016-04-27 KR KR1020160051792A patent/KR101738356B1/ko active Active
Non-Patent Citations (1)
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20190142569A (ko) * | 2018-06-18 | 2019-12-27 | 숭실대학교산학협력단 | 폴리락틱산 강인화제용 조성물, 이를 통해 제조된 강인화성 폴리락틱산 공중합체 및 이의 제조방법 |
KR102103011B1 (ko) | 2018-06-18 | 2020-04-22 | 숭실대학교산학협력단 | 폴리락틱산 강인화제용 조성물, 이를 통해 제조된 강인화성 폴리락틱산 공중합체 및 이의 제조방법 |
CN109777198A (zh) * | 2019-02-13 | 2019-05-21 | 新昌县高纤纺织有限公司 | 环保可溶性油墨及其制备工艺 |
US20200291253A1 (en) * | 2019-03-12 | 2020-09-17 | Unist(Ulsan National Institute Of Science And Technology) | Ink composition for bioprinting and hydrogel formed from the same |
KR20200109139A (ko) * | 2019-03-12 | 2020-09-22 | 울산과학기술원 | 바이오 프린팅용 잉크 조성물 및 그로부터 형성된 하이드로젤 |
KR102188574B1 (ko) * | 2019-03-12 | 2020-12-08 | 울산과학기술원 | 바이오 프린팅용 잉크 조성물 및 그로부터 형성된 하이드로젤 |
US11891529B2 (en) * | 2019-03-12 | 2024-02-06 | Unist(Ulsan National Institute Of Science And Technology) | Ink composition for bioprinting and hydrogel formed from the same |
CN114149565A (zh) * | 2021-11-30 | 2022-03-08 | 江苏三木化工股份有限公司 | 一种可光固化的超支化聚氨酯-环氧丙烯酸酯的制备方法 |
CN114149565B (zh) * | 2021-11-30 | 2023-04-25 | 江苏三木化工股份有限公司 | 一种可光固化的超支化聚氨酯-环氧丙烯酸酯的制备方法 |
WO2023128570A1 (ko) * | 2021-12-30 | 2023-07-06 | 주식회사 아이센스 | 고분자 재료의 표면 처리용 조성물, 키트 및 표면 처리 방법 |
KR20230102272A (ko) * | 2021-12-30 | 2023-07-07 | 주식회사 아이센스 | 고분자 재료의 표면 처리용 조성물, 키트 및 표면 처리 방법 |
KR102721932B1 (ko) | 2021-12-30 | 2024-10-25 | 주식회사 아이센스 | 고분자 재료의 표면 처리용 조성물, 키트 및 표면 처리 방법 |
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