KR101679683B1 - 고탄성 폴리에스터 변성 우레탄 수지 및 이를 포함하는 클리어코트 조성물 - Google Patents
고탄성 폴리에스터 변성 우레탄 수지 및 이를 포함하는 클리어코트 조성물 Download PDFInfo
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- KR101679683B1 KR101679683B1 KR1020140188540A KR20140188540A KR101679683B1 KR 101679683 B1 KR101679683 B1 KR 101679683B1 KR 1020140188540 A KR1020140188540 A KR 1020140188540A KR 20140188540 A KR20140188540 A KR 20140188540A KR 101679683 B1 KR101679683 B1 KR 101679683B1
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- South Korea
- Prior art keywords
- polyester
- urethane resin
- weight
- modified urethane
- aliphatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003673 urethanes Chemical class 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 229920000728 polyester Polymers 0.000 title claims description 19
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 6
- 229920005989 resin Polymers 0.000 claims abstract description 48
- 239000011347 resin Substances 0.000 claims abstract description 48
- -1 aliphatic isocyanate Chemical class 0.000 claims abstract description 31
- 229920005862 polyol Polymers 0.000 claims abstract description 24
- 239000011247 coating layer Substances 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- LAWHHRXCBUNWFI-UHFFFAOYSA-N 2-pentylpropanedioic acid Chemical compound CCCCCC(C(O)=O)C(O)=O LAWHHRXCBUNWFI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 25
- 239000012948 isocyanate Substances 0.000 abstract description 11
- 239000004645 polyester resin Substances 0.000 abstract description 9
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- 125000002723 alicyclic group Chemical group 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
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- 230000000704 physical effect Effects 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
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- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SQQOYWYEAFEMSV-UHFFFAOYSA-N COC(C(OCNC1=NC(=NC(=N1)N)N)(OC)OC)CC(OC)(OC)OC Chemical compound COC(C(OCNC1=NC(=NC(=N1)N)N)(OC)OC)CC(OC)(OC)OC SQQOYWYEAFEMSV-UHFFFAOYSA-N 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
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- HADQPSVKQVPWCO-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methyl methanimidate Chemical compound NC1=NC(N)=NC(NCOC=N)=N1 HADQPSVKQVPWCO-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/906—Fiber or elastomer prepared from an isocyanate reactant
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Abstract
Description
Claims (12)
- 수지 구성 단위로서, (1) 지방족 다가 알코올과, 헥산디카르복시산 및 사이클로헥실디카르복시산의 조합으로부터 얻어지는 폴리에스터 유래 단위, (2) 카프로락톤 폴리올 유래 단위 및 (3) 지방족 디이소시아네이트 유래 단위를 포함하고,
30~200 mgKOH/g의 수산기가 및 1~50mgKOH/g의 산가를 갖는, 폴리에스터 변성 우레탄 수지. - 제1항에 있어서, 지방족 다가 알코올이 수산기를 2개 이상 갖는 탄소수 3 내지 12의 지방족 화합물 1종 이상인, 폴리에스터 변성 우레탄 수지.
- 제1항에 있어서, 지방족 다가 알코올이 프로판디올, 부탄디올, 네오펜틸 글리콜, 트리메틸올 프로판 및 이들의 조합으로부터 선택되는, 폴리에스터 변성 우레탄 수지.
- 삭제
- 삭제
- 제1항에 있어서, 지방족 디이소시아네이트가 2개의 이소시아네이트기를 갖는 탄소수 4 내지 20의 지방족 또는 지환족 탄화수소 화합물 1종 이상인, 폴리에스터 변성 우레탄 수지.
- 제1항에 있어서, 지방족 디이소시아네이트가 헥사메틸렌 디이소시아네이트, 이소포론 디이소시아네이트, 디사이클로헥실메탄 디이소시아네이트 및 이들의 조합으로부터 선택되는, 폴리에스터 변성 우레탄 수지.
- 삭제
- (a) 지방족 다가 알코올과, 헥산디카르복시산 및 사이클로헥실디카르복시산의 조합을 반응시켜 폴리에스터 중간체를 합성하는 단계; 및 (b) 상기 합성된 폴리에스터 중간체, 카프로락톤 폴리올 및 지방족 디이소시아네이트를 반응시켜 폴리에스터 변성 우레탄 수지를 합성하는 단계를 포함하고,
합성된 폴리에스터 변성 우레탄 수지는 30~200 mgKOH/g의 수산기가 및 1~50mgKOH/g의 산가를 갖는 것인,
폴리에스터 변성 우레탄 수지의 제조방법. - 조성물 총 100중량부를 기준으로, 제1항 내지 제3항, 제6항 및 제7항 중 어느 한 항의 폴리에스터 변성 우레탄 수지 5~30 중량부; 실란변성 아크릴 폴리올 수지 20~60 중량부; 경화제 5~30 중량부; 경화촉매 0.5~3 중량부; 및 용제 10~25 중량부를 포함하는 클리어코트 조성물.
- 제10항에 있어서, 실란변성 아크릴 폴리올 수지의 중량평균 분자량(Mw)이 5,000~10,000이고, 수산기가가 20~120 mgKOH/g이며, 유리전이온도가 10~80℃인, 클리어코트 조성물.
- 제10항의 클리어코트 조성물로부터 형성된 하나 이상의 코팅층을 포함하는 성형품.
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KR1020140188540A KR101679683B1 (ko) | 2014-12-24 | 2014-12-24 | 고탄성 폴리에스터 변성 우레탄 수지 및 이를 포함하는 클리어코트 조성물 |
JP2017534558A JP6454018B2 (ja) | 2014-12-24 | 2015-04-15 | 高弾性ポリエステル変性ウレタン樹脂及びこれを含むクリアコート組成物 |
CN201580070053.3A CN107108853B (zh) | 2014-12-24 | 2015-04-15 | 高弹性聚酯改性的氨基甲酸乙酯树脂及包含其的透明涂料组合物 |
PCT/KR2015/003764 WO2016104875A1 (ko) | 2014-12-24 | 2015-04-15 | 고탄성 폴리에스터 변성 우레탄 수지 및 이를 포함하는 클리어코트 조성물 |
EP15873403.8A EP3239204B1 (en) | 2014-12-24 | 2015-04-15 | Highly elastic polyester modified urethane resin, and clear coat composition containing same |
US15/539,248 US10239986B2 (en) | 2014-12-24 | 2015-04-15 | Highly elastic polyester modified urethane resin and clear coat composition containing same |
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KR102023353B1 (ko) * | 2017-09-29 | 2019-09-20 | 주식회사 케이씨씨 | 클리어코트 조성물 |
KR101944707B1 (ko) * | 2018-09-28 | 2019-02-01 | 박도선 | 차량의 판금도장방법 |
KR101944706B1 (ko) * | 2018-09-28 | 2019-04-17 | 박도선 | 차량의 보수도장방법 |
KR102557478B1 (ko) | 2020-12-10 | 2023-07-19 | 한국화학연구원 | 이황화 폴리우레탄 디올 부가물, 이를 포함하는 클리어코트 조성물 및 그 용도 |
KR102695447B1 (ko) * | 2021-12-02 | 2024-08-13 | (주)엘엑스하우시스 | 코팅 조성물 및 이를 이용한 시트 |
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US20180022858A1 (en) | 2018-01-25 |
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EP3239204B1 (en) | 2018-12-19 |
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