CN114651023A - 疏水改性环氧烷聚合物混合物 - Google Patents
疏水改性环氧烷聚合物混合物 Download PDFInfo
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- CN114651023A CN114651023A CN202080076456.XA CN202080076456A CN114651023A CN 114651023 A CN114651023 A CN 114651023A CN 202080076456 A CN202080076456 A CN 202080076456A CN 114651023 A CN114651023 A CN 114651023A
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- hydrophobic
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- alkylene oxide
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- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 47
- 229920002959 polymer blend Polymers 0.000 title claims description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 65
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 30
- 230000002209 hydrophobic effect Effects 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- PBJZAYSKNIIHMZ-UHFFFAOYSA-N ethyl carbamate;oxirane Chemical class C1CO1.CCOC(N)=O PBJZAYSKNIIHMZ-UHFFFAOYSA-N 0.000 claims description 14
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003335 secondary amines Chemical class 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- -1 benzyl (2-hydroxyethyl) amino Chemical group 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 claims description 4
- ALHBLRKLEOWQSK-UHFFFAOYSA-N 1-(dibenzylamino)-3-(2-ethylhexoxy)propan-2-ol Chemical compound C1(=CC=CC=C1)CN(CC(COCC(CCCC)CC)O)CC1=CC=CC=C1 ALHBLRKLEOWQSK-UHFFFAOYSA-N 0.000 claims description 3
- CVAAEKRJDXOUAL-UHFFFAOYSA-N 1-[benzyl(2-hydroxyethyl)amino]-3-butoxypropan-2-ol Chemical compound CCCCOCC(O)CN(CCO)CC1=CC=CC=C1 CVAAEKRJDXOUAL-UHFFFAOYSA-N 0.000 claims description 3
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 claims description 3
- VKWCWZFROPXPFK-UHFFFAOYSA-N 1-butan-2-yloxy-3-(dibenzylamino)propan-2-ol Chemical compound C1(=CC=CC=C1)CN(CC(COC(C)CC)O)CC1=CC=CC=C1 VKWCWZFROPXPFK-UHFFFAOYSA-N 0.000 claims description 3
- ZVFMAVXIWCBWRK-UHFFFAOYSA-N 2-(diheptylamino)ethanol Chemical compound CCCCCCCN(CCO)CCCCCCC ZVFMAVXIWCBWRK-UHFFFAOYSA-N 0.000 claims description 3
- FPHDWNIKZCZSLT-UHFFFAOYSA-N 2-(dihexylamino)ethanol Chemical compound CCCCCCN(CCO)CCCCCC FPHDWNIKZCZSLT-UHFFFAOYSA-N 0.000 claims description 3
- BIFHTUIYFKXCAU-UHFFFAOYSA-N 2-(dioctylamino)ethanol Chemical compound CCCCCCCCN(CCO)CCCCCCCC BIFHTUIYFKXCAU-UHFFFAOYSA-N 0.000 claims description 3
- IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 claims description 3
- WOUANPHGFPAJCA-UHFFFAOYSA-N 2-[benzyl(methyl)amino]ethanol Chemical compound OCCN(C)CC1=CC=CC=C1 WOUANPHGFPAJCA-UHFFFAOYSA-N 0.000 claims description 3
- FMFWSIARXFCACS-UHFFFAOYSA-N 2-[bis(2-ethylhexyl)amino]ethanol Chemical compound CCCCC(CC)CN(CCO)CC(CC)CCCC FMFWSIARXFCACS-UHFFFAOYSA-N 0.000 claims description 3
- DMPODMBXLRMZSP-UHFFFAOYSA-N 3-(dibutylamino)propan-1-ol Chemical compound CCCCN(CCCC)CCCO DMPODMBXLRMZSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 abstract description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 description 7
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- 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 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 235000012208 gluconic acid Nutrition 0.000 description 4
- 239000000174 gluconic acid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 3
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- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical class O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- SCBKAXLZFJBCTI-UHFFFAOYSA-N 1-[benzyl(2-hydroxyethyl)amino]-3-(2-ethylhexoxy)propan-2-ol Chemical compound CCCCC(CC)COCC(O)CN(CCO)CC1=CC=CC=C1 SCBKAXLZFJBCTI-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000008876 conformational transition Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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Abstract
本发明涉及一种组合物,该组合物包含第一和第二疏水改性环氧烷聚合物的混合物,其中所述第一疏水改性环氧烷聚合物用至少一个经仲胺或其盐、或叔胺或其盐功能化的第一疏水基团封端;并且其中所述第二疏水改性环氧烷聚合物用至少一个第二疏水基团结构I封端:其中R1、R2、m、和n如本文中所定义。本发明还涉及制备该组合物的方法。本发明的组合物提供了一种缔合型增稠剂,其在宽温度范围内具有良好的原样粘度和温度稳定性的平衡。
Description
背景技术
本发明涉及一种组合物,该组合物包含疏水改性环氧烷聚合物的混合物,更特别是,用不同的疏水基团封端的疏水改性环氧乙烷聚合物(HEUR)的混合物。
HEUR是一类缔合增稠剂,用于控制水性涂料配方的粘度。已知用烷基或芳族基团封端的HEUR是有效的增稠剂;然而,此类材料有两个缺点:首先,此类HEUR的水溶液通常需要助溶剂或环糊精来抑制原样粘度,即含有约15至30重量百分比的HEUR的水溶液的Brookfield粘度,低于10,000cps;如此低的粘度对于使HEUR更易于处理和泵入涂料配方中是必要的。其次,众所周知,用这些HEUR增稠的涂料会随温度升高而展现出不可接受的粘度大幅下降(ΔKU>25Krebs单位)。因此,本领域需要一种流变调节剂,其在没有助溶剂或其他添加剂的情况下显示出可接受的原样粘度,并且在涂料和其他涂布配方通常暴露的温度范围内具有伴随粘度稳定性。
发明内容
本发明通过提供一种组合物解决本领域的需求,该组合物包含第一和第二疏水改性环氧烷聚合物的混合物,其中所述第一疏水改性环氧烷聚合物用至少一个经仲胺或其盐、或叔胺或其盐功能化的第一疏水基团封端;并且其中所述第二疏水改性环氧烷聚合物用至少一个第二疏水基团结构I封端:
其中虚线表示结构I的疏水基团与所述环氧烷聚合物主链的连接点;其中R1是C1-C10-烷基;R2是C1-C6-烷基;m是5至40;n是0至50,条件是当m是5至9时,n是0至10。本发明的组合物提供了一种缔合型增稠剂,其在宽温度范围内具有优异的原样粘度和温度稳定性的平衡。
具体实施方式
本发明是一种组合物,该组合物包含第一和第二疏水改性环氧烷聚合物的混合物,其中第一疏水改性环氧烷聚合物用至少一个经仲胺或其盐、或叔胺或其盐功能化的第一疏水基团封端;并且其中第二疏水改性环氧烷聚合物用至少一个第二疏水基团结构I封端:
其中虚线表示结构I的疏水基团与所述环氧烷聚合物主链的连接点;其中R1是C1-C10-烷基;R2是C1-C6-烷基;m是5至40;n是0至50,条件是当m是5至9时,n是0至10。
优选地,R1为C1-C8烷基,更优选C2-C6-烷基;R2优选甲基或乙基;更优选甲基;m优选从10开始,更优选从12开始,优选至30,更优选至20;n优选为0至20,更优选0。
如本文中所使用,术语“环氧烷聚合物”是指水溶性聚氧化乙烯聚合物,以及水溶性聚氧化乙烯/聚氧化丙烯和聚氧化乙烯/聚氧化丁烯共聚物。优选地,环氧烷聚合物为环氧烷氨基甲酸酯聚合物,更优选地为环氧乙烷氨基甲酸酯聚合物。
水溶性聚烷二醇是指水溶性聚环氧乙烷、水溶性聚环氧乙烷/聚环氧丙烷共聚物和水溶性聚环氧乙烷/聚环氧丁烷共聚物。优选的水溶性聚环氧烷为聚乙二醇,尤其为重均分子量在4000,更优选6000并且最优选7000至20,000,更优选至12,000并且最优选至9000道尔顿(Dalton)的范围内的聚乙二醇。适合聚乙二醇的实例是商购自CARBOWAXTM8000聚乙二醇(陶氏化学公司(The Dow Chemical Company)(“陶氏”)或密歇根州米德兰陶氏附属公司(affiliate of Dow,Midland,MI)的商标)的PEG 8000。
二异氰酸酯的实例包含1,4-四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4-三甲基-1,6-二异氰酸酯基己烷、1,10-十亚甲基二异氰酸酯、4,4′-亚甲基双(异氰酸酯基环己烷)、二异氰酸1,4-环己二酯、1-异氰酸酯基-3-异氰酸酯基甲基-3,5,5-三甲基环己烷和间亚苯基二异氰酸酯及对亚苯基二异氰酸酯。
如本文中所用,术语“第一疏水基团”是指第一疏水化合物,不同之处在于与优选的环氧烷聚合物主链的异氰酸酯部分所反应的一个或多个基团结合的一个或多个氢原子。例如,如果用于形成第一疏水基团的第一疏水化合物是2-(二丁基氨基)乙醇,则第一疏水基团由下式表征:
其中虚线表示与环氧烷聚合物主链的连接点。例如,如果用于形成第一疏水基团的疏水化合物为2-(二丁氨基)乙胺,那么第一疏水基团的特征由下式表征:
在第一实例中,第一疏水化合物与例如异氰酸酯基反应以形成氨基甲酸酯;在第二实例中,第一疏水化合物与异氰酸酯基反应以形成脲。
游离碱形式的第一疏水基团优选具有从2、更优选从4、至12、更优选至10、最优选至8的范围内的计算的Log P(cLog P)。cLog P是使用ChemBioDraw Ultra13.0(PerkinElmer)确定的,它使用化学片段算法方法来评估基于其组成部分的分子的分配系数。
可用于产生第一疏水基团的化合物的实例包括2-(叔-丁基氨基)乙醇;2-(二丁基氨基)乙醇;2-(二辛基氨基)乙醇;2-(二庚氨基)乙醇;2-(双(2-乙基己基)氨基)乙醇(BEHAE,cLog P=6.75));2-(二己氨基)乙醇;3-(二丁基氨基)丙醇;2-(二丁基氨基)乙胺;3-(二丁基氨基)丙胺;N-苄基-N-甲基乙醇胺;1-(二丁胺)-2-丁醇;4-氨基-1-苄基-哌啶;1-(苄基(2-羟乙基)氨基)-3-烷氧基丙-2-醇诸如1-(苄基(2-羟乙基)氨基)-3-丁氧基丙-2-醇和1-(苄基(2-羟乙基)氨基)-3-(2-乙基己基)氧基丙-2-醇;1-[双(苯基甲基)氨基]-3-[(2-烷氧基]-2-丙醇诸如1-[双(苯基甲基)氨基]-3-[(2-丁基)氧基]-2-丙醇和1-[双(苯基甲基)氨基]-3-[(2-乙基己基)氧基]-2-丙醇;和以下类型的二苄基氨基聚环氧烷:
其中R3是甲基或乙基并且p为1至10。第一疏水基团被称为用于产生第一疏水基团的化合物的残余物。
尽管不受理论的束缚,但据信包含至少5个环氧丙烷基团(即m>5)的结构I疏水物在低温下倾向于塌缩(卷曲)并在分子内水平上缔合,但在更高的温度下会伸展(拉直)。这种构象转变是侧基疏水性增加的证据。随着温度升高,这些基团变得更加疏水,因此更易于与粘合剂发生分子间缔合,从而改善温度稳定性。
优选的疏水改性环氧烷氨基甲酸酯聚合物宜通过在适合反应条件下使以下物质接触而制备:a)水溶性聚亚烷基二醇;b)相对于聚亚烷基二醇,化学计量过量的二异氰酸酯;和c1的混合物)经仲胺或叔胺或季铵盐官能化的第一疏水化合物;和c2)结构Ia的第二疏水化合物,以形成疏水改性的环氧烷氨基甲酸酯聚合物,其中结构Ia的疏水化合物如下:
结构Ia的疏水化合物可以根据以下反应方案方便地制备:
结构I的疏水化合物是结构Ia的疏水化合物的残余物。结构Ia化合物的商业实例是UCONTMLB-285聚亚烷基二醇(LB-285,陶氏化学公司或其附属公司的商标),一种低聚聚环氧丙烷一元醇。
组分b)还可以是二氯甲烷、二溴甲烷、表氯醇或代替二异氰酸酯的氨基塑料。可以调整c1)和c2)的相对量以调整组合物的性质。当使用该优选方法时,该组合物包含环氧烷聚合物的混合物,优选环氧乙烷氨基甲酸酯聚合物,一个用两个第一疏水基团封端,一个用两个第二疏水基团封端,和一个用第一疏水基团和第二疏水基团封端。因此,在本发明的另一个方面,该组合物包含用两个第一疏水基团封端的第一疏水改性环氧烷聚合物;用两个结构I的第二疏水基团封端的第二疏水改性环氧烷聚合物,其中所述组合物还包含用第一和第二疏水基团封端的疏水改性环氧烷聚合物。
优选地,用第一疏水基团和第二疏水基团封端的HEUR与仅用第一疏水基团和仅被第二疏水基团封端的HEUR总和的摩尔:摩尔比在1:3至1:1的范围内;优选地,第一疏水基团与第二疏水基团的摩尔:摩尔比在15:85、更优选25:75至优选60:40、更优选至50:50的范围内。
或者,优选的组合物可以通过使摩尔过量的二异氰酸酯与聚亚烷基二醇预反应以制备具有剩余异氰酸酯基团的环氧烷-氨基甲酸酯聚合物主链,然后以任何顺序或同时与第一和第二疏水化合物反应来制备。
在制备本发明组合物的另一种但不太优选的方法中,组分a)、b)和c1)在反应条件下接触以形成用第一疏水基团封端的第一疏水改性环氧烷氨基甲酸酯聚合物。在单独的反应中,组分a)、b)和c2)在反应条件下接触以形成用第二疏水基团封端的第二疏水改性环氧烷氨基甲酸酯聚合物。然后,将第一和第二疏水改性的环氧烷氨基甲酸酯氧化物聚合物以预定比例组合。
本发明的组合物优选与水混合以形成水溶液。本发明的组合物适用于涂料配方,尤其着色涂料配方,并且可进一步包含其它组分,包括粘合剂、颜料、表面活性剂、聚结剂、消泡剂、不透明聚合物、和增量剂。
实施例
所有HEUR固体样品都以20%活性HEUR固体和2%葡萄糖酸溶解在水中。在以下实施例中,仅经封端剂LB-285或BEHAE官能化的HEUR是用于共混物实施例的中间体,以及用于用两种封端剂共同封端的HEUR的比较例的中间体。中间例1(比较例1)——仅用LB-285封端的HEUR的制备
将CARBOWAXTM8000聚乙二醇(陶氏化学公司或其附属公司的商标,PEG8000,1500g)在批式熔融反应器中在真空中加热到110℃维持2小时。将熔体冷却至100℃,然后将丁基化羟基甲苯(BHT,0.188g)和LB-285(301.61g)添加到反应器中。将混合物搅拌5分钟,然后将Desmodur W二环己基甲烷-4,4-二异氰酸酯(Des W,77.47g)添加到反应器中。将反应混合物搅拌5分钟,然后将辛酸铋(28%Bi,3.75g)加入到反应器中。将混合物在100℃搅拌10分钟,然后将所得熔融聚合物从反应器中取出并冷却。
中间例2(比较例2)——仅用BEHAE封端的HEUR的制备
在批式熔融反应器中在真空中将PEG 8000(1700g)加热到110℃维持2小时。将熔体冷却至100℃,然后将BHT(0.19g)和BEHAE(103.47g)添加到反应器中。将混合物搅拌5分钟,然后将Des W(94.95g)添加到反应器中。将反应混合物搅拌5分钟,然后将辛酸铋(28%Bi,4.75g)加入反应器中,并将所得混合物在100℃搅拌10分钟。将混合物在100℃搅拌10分钟,然后将所得熔融聚合物从反应器中取出并冷却。
实施例1–用LB-285和BEHAE共同封端的HEUR的制备
在批式熔融反应器中在真空中将PEG 800(1500g)加热到110℃维持2小时。将反应熔体冷却至100℃,然后将BHT(0.179g)、LB-285(266.86g)和BEHAE(16.6g)添加到反应器中。LB-285:BEHAE的摩尔:摩尔比为82:18。将混合物搅拌5分钟,然后将Des W(83.78g)添加到反应器中。将反应混合物搅拌5分钟,然后将辛酸铋(28%Bi,3.75g)加入反应器中,将所得混合物在100℃搅拌10分钟。将混合物在100℃搅拌10分钟,然后将所得熔融聚合物从反应器中取出并冷却。
实施例2-4–用不同水平的LB-285和BEHAE共同封端的HEUR的制备
基本上如实施例1的描述来制备共封端的HEUR,不同的是LB-285:BEHAE的摩尔:摩尔比不同。共同封端的HEUR和单独封端的HEUR的共混物按原样粘度进行评估,并在单独的评估中配制成涂料,评估粘度稳定性。使用Brookfield粘度计、#3转子、以30rpm测量原样粘度(cps)。ΔKU是使用Brookfield KU-1+粘度计或等效的KU粘度计测得的在38℃时测量的涂料的KU粘度与2℃时测量的涂料KU粘度之差。
表1示例了涂料配方并且表2示例了共同封端的HEUR对比仅使用LB-285或BEHAE封端的HEUR的性能。
表1–涂料配方
在下表2中,所有涂料均在25℃时增稠至KU=100和ICI=1.2泊;HEUR干lbs是指HEUR/100加仑涂料的总干lbs。摩尔%LB-285未显示,但计算为100–摩尔%BEHAE。原样粘度以cps为单位。低于10,000cps的原样粘度和在20至-20之间的ΔKU是可以接受的。按水和HEUR的重量计,HEUR水溶液(HEUR Aq.sol.)的固体含量是20重量百分比。按水、HEUR和葡糖酸的重量计,HEUR溶液还含有2重量百分比的葡糖酸。
表2–共同封端HEUR与单独封端HEUR的性质
示例5–单独封端的HEUR的共混物
中间实施例1干聚合物(5.84克)、中间实施例2干聚合物(2.16克)、水(30.4克)和葡糖酸(50%水溶液,1.6克)在室温下混合直至溶解和均匀。所得溶液的pH为2.77。来自中间实施例1的封端剂与来自中间实施例2的封端剂的摩尔:摩尔比为90:10。
实施例6-8–不同数量的单独封端HEUR的共混物
单独封端HEUR的共混物按实施例5中的描述制备,不同之处在于用量与表3中所示不同。
表3–单独封端HEUR的共混物
共混的HEUR的性质在表4中示出。
表4–单独封端HEUR的共混物的性质
表2和表4的数据表明,具有可接受的原样粘度和温度稳定性的HEUR可以通过将本文所述的用疏水化合物共同封端HEUR或通过共混不同的单独封端的HEUR来制备。尽管如此,共同封端的HEUR更容易制备,并且明显具有在优化组合中减少干磅负载的额外优势。
权利要求书(按照条约第19条的修改)
1.一种组合物,所述组合物包含第一和第二疏水改性的环氧烷聚合物的混合物,其中,所述第一疏水改性环氧烷聚合物用至少一个用仲胺或其盐、或叔胺或其盐官能化的第一疏水基团封端;并且其中所述第二疏水改性的环氧烷聚合物用至少一个第二疏水基团结构I封端:
其中虚线表示结构I的疏水基团与所述环氧烷聚合物主链的连接点;其中R1是C1-C10-烷基;R2是C1-C6-烷基;m是5至40;n是0至50,条件是当m是5至9时,n是0至10。
2.根据权利要求1所述的组合物,其中所述第一和第二疏水改性的环氧烷聚合物是疏水改性环氧乙烷氨基甲酸酯聚合物。
3.根据权利要求2所述的组合物,其中R1是C1-C8烷基;R2是甲基或乙基;m是10至30;n是0到20。
4.根据权利要求3所述的组合物,其中R1是C2-C6烷基;R2是甲基;m是12至20;并且n是0。
5.根据权利要求3所述的组合物,其中所述至少一个第一疏水基团具有在2至12的范围内的计算Log P。
6.根据权利要求4所述的组合物,其中所述至少一个第一疏水基团是选自于下列所组成的组的化合物的残余物:2-(叔-丁基氨基)乙醇;2-(二丁基氨基)乙醇;2-(二辛基氨基)乙醇;2-(二庚氨基)乙醇;2-(双(2-乙基己基)氨基)乙醇;2-(二己氨基)乙醇;3-(二丁基氨基)丙醇;2-(二丁基氨基)乙胺;3-(二丁基氨基)丙胺;N-苄基-N-甲基乙醇胺;1-(二丁胺)-2-丁醇;4-氨基-1-苄基-哌啶;1-(苄基(2-羟乙基)氨基)-3-丁氧基丙-2-醇;1-(苄基(2-羟乙基)氨基)-3-(2-乙基己基)氧基丙-2-醇;1-[双(苯基甲基)氨基]-3-[(2-丁基)氧基]-2-丙醇;1-[双(苯基甲基)氨基]-3-[(2-乙基己基)氧基]-2-丙醇;和以下类型的二苄基氨基聚环氧烷:
其中R3是甲基或乙基并且p,1至10。
7.根据权利要求2的组合物,其中所述第一疏水改性环氧乙烷氨基甲酸酯聚合物用两个第一疏水基团封端;并且所述第二疏水改性环氧乙烷氨基甲酸酯聚合物用结构I的两个第二疏水基团封端,其中所述组合物进一步包含用第一和第二疏水基团封端的疏水改性环氧乙烷氨基甲酸酯聚合物。
8.根据权利要求7所述的组合物,其中用第一疏水基团和第二疏水基团封端的所述疏水改性环氧乙烷氨基甲酸酯聚合物与仅用第一疏水基团和仅用第二疏水基团封端的所述疏水改性环氧乙烷氨基甲酸酯聚合物的摩尔:摩尔比在1:3至1:1的范围内,该组合物为水溶液形式;其中所述第一疏水基团具有在4至10的范围内的计算log P。
9.根据权利要求8所述的组合物,其中第一疏水基团与第二疏水基团的摩尔:摩尔比在25:75至50:50的范围内。
10.根据权利要求1至9中任一项所述的组合物,其进一步包含颜料、粘合剂和至少一种选自于下列所组成的组的其他成分:表面活性剂、聚结剂、消泡剂、不透明聚合物、和增量剂。
11.一种制备疏水改性环氧烷氨基甲酸酯聚合物共混物的方法,其包括以下步骤:在反应条件下,使a)水溶性聚亚烷基二醇;b)相对于聚亚烷基二醇,化学计量过量的二异氰酸酯;c1)经仲胺或叔胺或季铵盐官能化的第一疏水化合物;和c2)结构Ia的第二疏水化合物接触,以形成所述疏水改性环氧烷氨基甲酸酯聚合物,其中结构Ia的疏水化合物如下:
其中R1是C1-C10-烷基;R2是C1-C6-烷基;m是5至40;以及n是0至50,条件是当m是5到9时,n是0到10。
12.一种制备疏水改性环氧烷氨基甲酸酯聚合物共混物的方法,包括以下步骤:
1)在反应条件下,使a)水溶性聚亚烷基二醇;和b)相对于聚亚烷基二醇化学计量过量的二异氰酸酯接触以产生具有残余异氰酸酯基团的环氧烷氨基甲酸酯聚合物;然后
2)以任何顺序或同时使环氧烷氨基甲酸酯聚合物与c1)经仲胺或叔胺或季铵盐官能化的第一疏水化合物;和c2)结构Ia的第二疏水化合物接触,以形成疏水改性环氧烷氨基甲酸酯聚合物,其中结构Ia的疏水化合物如下:
其中R1是C1-C10-烷基;R2是C1-C6-烷基;m是5至40;以及n是0至50,条件是当m是5到9时,n是0到10。
Claims (12)
2.根据权利要求1所述的组合物,其中所述第一和第二疏水改性的环氧烷聚合物是疏水改性环氧乙烷氨基甲酸酯聚合物。
3.根据权利要求2所述的组合物,其中R1是C1-C8烷基;R2是甲基或乙基;m是10至30;n是0到20。
4.根据权利要求3所述的组合物,其中R1是C2-C6烷基;R2是甲基;m是12至20;并且n是0。
5.根据权利要求3所述的组合物,其中所述至少一个第一疏水基团具有在2至12的范围内的计算Log P。
6.根据权利要求4所述的组合物,其中所述至少一个第一疏水基团是选自于下列所组成的组的化合物的残余物:2-(叔-丁基氨基)乙醇;2-(二丁基氨基)乙醇;2-(二辛基氨基)乙醇;2-(二庚氨基)乙醇;2-(双(2-乙基己基)氨基)乙醇;2-(二己氨基)乙醇;3-(二丁基氨基)丙醇;2-(二丁基氨基)乙胺;3-(二丁基氨基)丙胺;N-苄基-N-甲基乙醇胺;1-(二丁胺)-2-丁醇;4-氨基-1-苄基-哌啶;1-(苄基(2-羟乙基)氨基)-3-丁氧基丙-2-醇;1-(苄基(2-羟乙基)氨基)-3-(2-乙基己基)氧基丙-2-醇;1-[双(苯基甲基)氨基]-3-[(2-丁基)氧基]-2-丙醇;1-[双(苯基甲基)氨基]-3-[(2-乙基己基)氧基]-2-丙醇;和以下类型的二苄基氨基聚环氧烷:
其中R3是甲基或乙基并且p为1至10。
7.根据权利要求2的组合物,其中所述第一疏水改性环氧乙烷氨基甲酸酯聚合物用两个第一疏水基团封端;并且所述第二疏水改性环氧乙烷氨基甲酸酯聚合物用结构I的两个第二疏水基团封端,其中所述组合物进一步包含用第一和第二疏水基团封端的疏水改性环氧乙烷氨基甲酸酯聚合物。
8.根据权利要求7所述的组合物,其中用第一疏水基团和第二疏水基团封端的所述疏水改性环氧乙烷氨基甲酸酯聚合物与仅用第一疏水基团和仅用第二疏水基团封端的所述疏水改性环氧乙烷氨基甲酸酯聚合物的摩尔:摩尔比在1:3至1:1的范围内,该组合物为水溶液形式;其中所述第一疏水基团具有在4至10的范围内的计算log P。
9.根据权利要求8所述的组合物,其中第一疏水基团与第二疏水基团的摩尔:摩尔比在25:75至50:50的范围内。
10.根据权利要求1至9中任一项所述的组合物,其进一步包含颜料、粘合剂和至少一种选自于下列所组成的组的其他组分:表面活性剂、聚结剂、消泡剂、不透明聚合物、和增量剂。
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US20220356351A1 (en) | 2022-11-10 |
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