KR101966756B1 - 광중합 아크릴계 시럽의 제조방법 - Google Patents
광중합 아크릴계 시럽의 제조방법 Download PDFInfo
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- KR101966756B1 KR101966756B1 KR1020170085675A KR20170085675A KR101966756B1 KR 101966756 B1 KR101966756 B1 KR 101966756B1 KR 1020170085675 A KR1020170085675 A KR 1020170085675A KR 20170085675 A KR20170085675 A KR 20170085675A KR 101966756 B1 KR101966756 B1 KR 101966756B1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000006188 syrup Substances 0.000 title claims abstract description 59
- 235000020357 syrup Nutrition 0.000 title claims abstract description 59
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 60
- 229910052760 oxygen Inorganic materials 0.000 claims description 60
- 239000001301 oxygen Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 37
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 15
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003999 initiator Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 15
- 238000012662 bulk polymerization Methods 0.000 description 15
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 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 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- -1 acryl Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
구분 | 실시예1 | 실시예2 | 실시예3 | 실시예4 | 비교예1 | |
중합개시제 | TPO | 200몰% | 105몰% |
|
200몰% | 10,000ppm |
100몰% 3회추가 | ||||||
819 | 200몰% | |||||
CTA | n-DDM | 0.25% | ||||
광중합조건 | 조도 | 40mW/㎠ | 5mW/㎠ | 40mW/㎠ | 40mW/㎠ | 40mW/㎠ |
광량 | 3,000mJ/㎠ | 200mJ/㎠ | 3,000mJ/㎠ | 3,000mJ/㎠ | 7,000mJ/㎠ | |
3,000mJ/㎠ |
구분 | 실시예1 | 실시예2 | 실시예3 | 실시예4 | 비교예1 |
중합전환율(%) | 22 | 20 | 26 | 80 | 35 |
점도(cps, 25℃) | 2,200 | 8,700 | 2,600 | 3,500 | 1,800 |
수평균분자량 (g/mole) | 490,000 | 840,000 | 430,000 | 180,000 | 220,000 |
다분산지수 | 2.21 | 1.79 | 2.55 | 3.83 | 3.42 |
열에 대한 저장안정성 | ○ | ○ | ○ | ○ | ○ |
광에 대한 저장안전성 | ○ | ○ | ○ | ○ | × |
색차 (b*/YI) | 0.07/0.11 | 0.08/0.13 | 0.13/0.24 | 0.09/0.14 | 2.08/2.13 |
Claims (11)
- (1) 1종 이상의 아크릴계단량체를 포함하는 조성물의 용존산소 몰수 대비 101몰% 이상 200몰% 이하의 광개시제를 첨가하여 200㎚ 이상 600㎚ 이하의 파장에서 200mJ/㎠ 이상 5,000mJ/㎠ 이하의 광량으로 조성물에 잔존 광개시제가 없도록 광중합시키는 단계; 및
(2) 광중합시킨 조성물에 매회 용존산소 몰수의 1몰% 이상 100몰% 이하의 광개시제를 추가하여 상기 광량 범위에서 1회 이상 광중합시켜 중합전환율을 증가시키는 단계;
를 포함하는 것을 특징으로 하는 아크릴계 시럽의 제조방법. - 삭제
- 삭제
- 제1항에 있어서,
상기 (1)단계에서 조성물의 용존산소가 5㎎/L 이하에서 중합시키는 것을 특징으로 하는 아크릴계 시럽 제조방법. - 삭제
- 제1항에 있어서,
상기 (2)단계를 1회 이상 4회 이하 수행하여 중합전환율이 20중량% 이상 80중량% 이하인 것을 특징으로 하는 아크릴계 시럽 제조방법. - 제1항에 있어서,
상기 아크릴계단량체를 포함하는 조성물 중 극성단량체의 비율이 0중량% 초과 25중량% 이하인 것을 특징으로 하는 아크릴계 시럽 제조방법. - 제1항에 있어서,
상기 1종 이상의 아크릴계단량체를 포함하는 조성물에는 사슬이동제가 더 포함되며, 상기 사슬이동제의 함량이 0중량% 초과 0.25중량% 이하인 것을 특징으로 하는 아크릴계 시럽 제조방법. - 제1항에 있어서,
상기 광개시제는 2,4,6-트리메틸벤조일-디페닐-포스핀옥사이드(TPO) 또는 페닐비스-(2,4,6-트리메틸벤조일)-포스핀옥사이드(Irgacure 819) 중에서 선택되거나 혼합하여 사용하는 것을 특징으로 하는 아크릴계 시럽 제조방법. - 제1항에 있어서,
상기 아크릴계시럽의 수평균분자량이 30,000g/mole 이상1,000,000g/mole 이하이고, 다분산지수가 1.5 이상 4.0 이하인 것을 특징으로 하는 아크릴계 시럽 제조방법. - 제1항에 있어서,
상기 아크릴계중합체의 25℃에서의 점도가 1,000cps 이상 10,000cps 이하인 것을 특징으로 하는 아크릴계 시럽 제조방법.
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KR1020170085675A KR101966756B1 (ko) | 2017-07-05 | 2017-07-05 | 광중합 아크릴계 시럽의 제조방법 |
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KR1020170085675A KR101966756B1 (ko) | 2017-07-05 | 2017-07-05 | 광중합 아크릴계 시럽의 제조방법 |
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KR20190005089A KR20190005089A (ko) | 2019-01-15 |
KR101966756B1 true KR101966756B1 (ko) | 2019-04-09 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005132962A (ja) | 2003-10-30 | 2005-05-26 | Soken Chem & Eng Co Ltd | (メタ)アクリル系重合体の製造方法 |
WO2013088889A1 (ja) | 2011-12-13 | 2013-06-20 | 昭和電工株式会社 | 透明両面粘着シートの製造方法、透明両面粘着シート |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09316114A (ja) * | 1996-05-29 | 1997-12-09 | Sekisui Chem Co Ltd | 光重合性組成物及びアクリル系粘着剤 |
KR101998654B1 (ko) * | 2014-09-29 | 2019-07-11 | 주식회사 엘지화학 | 아크릴 시럽의 제조방법 및 아크릴 시럽 |
KR101997581B1 (ko) * | 2015-10-01 | 2019-10-02 | 주식회사 엘지화학 | (메타)아크릴계 시럽의 제조방법 및 (메타)아크릴계 시럽 |
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2017
- 2017-07-05 KR KR1020170085675A patent/KR101966756B1/ko active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005132962A (ja) | 2003-10-30 | 2005-05-26 | Soken Chem & Eng Co Ltd | (メタ)アクリル系重合体の製造方法 |
WO2013088889A1 (ja) | 2011-12-13 | 2013-06-20 | 昭和電工株式会社 | 透明両面粘着シートの製造方法、透明両面粘着シート |
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