JP2021522225A - 1つ又は2つの第二級アミノ基を有するジカルボン酸塩を含むポリウレタンの水分散液 - Google Patents
1つ又は2つの第二級アミノ基を有するジカルボン酸塩を含むポリウレタンの水分散液 Download PDFInfo
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- JP2021522225A JP2021522225A JP2020558877A JP2020558877A JP2021522225A JP 2021522225 A JP2021522225 A JP 2021522225A JP 2020558877 A JP2020558877 A JP 2020558877A JP 2020558877 A JP2020558877 A JP 2020558877A JP 2021522225 A JP2021522225 A JP 2021522225A
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- Prior art keywords
- polyurethane
- dicarboxylic acid
- aqueous dispersion
- acid salt
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 52
- 239000004814 polyurethane Substances 0.000 title claims abstract description 52
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 title claims abstract description 30
- 239000006185 dispersion Substances 0.000 title claims abstract description 28
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 150000002009 diols Chemical class 0.000 claims abstract description 33
- 239000012948 isocyanate Substances 0.000 claims abstract description 17
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 17
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- -1 veneer board Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000001767 cationic compounds Chemical class 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000002892 organic cations Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
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- 239000004566 building material Substances 0.000 claims description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
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- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 239000011087 paperboard Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 238000010586 diagram Methods 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
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- 239000000084 colloidal system Substances 0.000 description 6
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- 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 6
- 239000002245 particle Substances 0.000 description 6
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 0 CN=CCCN*NCCC=NC Chemical compound CN=CCCN*NCCC=NC 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
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- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
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- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
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- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
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- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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- C08G18/3228—Polyamines acyclic
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- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
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- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/50—Aqueous dispersion, e.g. containing polymers with a glass transition temperature (Tg) above 20°C
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Abstract
【選択図】なし
Description
上記ポリウレタンは、二官能又は多官能イソシアネート、ジオール、1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び場合により、更なる化合物を反応させることによって得られる。
X)二重結合及びカルボン酸基又はカルボン酸基に移行され得る基を有する化合物
を
Y)2つの第一級アミノ基を含む化合物
と反応させることによって合成し得る。
上記ポリウレタンは、二官能又は多官能イソシアネート、ジオール、少なくとも1つの第二級アミノ基を有するジカルボン酸、及び場合により、更なる化合物を反応させることによって得られる。
a)炭素原子数4〜30の二官能又は多官能イソシアネート、
b)ジオールであって、
b.1)ジオール(b)の総量に対して10〜100mol%の分子量が、500〜5000であり、
b.2)ジオール(b)の総量に対して0〜90mol%の分子量が、60〜500g/molである、ジオール、
c)1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び
d)場合により、少なくとも1つのイソシアネート基又は少なくとも1つのイソシアネート反応性基を有する化合物であって、化合物a)、b)、及びc)とは異なる化合物
を反応させることによって得られる。
A)が、イソシアネート基のモル量であり、
B)が、水酸基、及び付加反応でイソシアネートと反応可能な全ての他の官能基のモル量の合計である
A:B比が、0.5:1〜2:1、好ましくは0.8:1〜1.5、より好ましくは0.9:1〜1.2:1であるようなモル量で反応させる。極めて好ましくは、A:B比が、可能な限り1:1に近い。
I)化合物a)、b)、c)、及び場合により、d)を、有機溶媒中でポリウレタンと反応させ、
II)ポリウレタンを水に分散させ、ここで
イソシアネート反応性基として第一級又は第二級アミノ基を有する成分d)を、I)で反応させてもよく、又はステップIIの間か、若しくはステップIIの後に、部分的に、若しくは全てを加えてもよい、方法によって得られる。
H12MDI 1,1-メチレンビス[4-イソシアナト]シクロヘキサン
化合物II 式IIの化合物
DETA ジエチレントリアミン
PUD ポリウレタン分散液
Baxxodur(登録商標)PC136 各2molのアクリロニトリル及びIPDAの付加物
化合物IIの調製
化合物IIを用いたPUDの調製
アジピン酸、ネオペンチルグリコール、及び1,6-ヘキサンジオール(モル比1/1)(OH価56)から生成されたポリエステルジオール600g(0.30mol)、ブタノール出発ポリエチレンオキシド26.7g(0.014mol)、アセトン100g、並びにジラウリン酸ジブチル錫0.3gを容器にいれ、83℃で撹拌した。次に、89.8g(0.404mol)のIPDI及び106.7g(0.404mol)のH12MDIを加え、続けて、得られた混合物を、83℃で60分間撹拌した。次に、1,4-ブタンジオール27.0g(0.30mol)を加え、反応を更に120分間継続させた。この混合物にアセトン850gを加えて希釈した。得られた混合物のNCO含有率は、0.91重量%(計算上:0.93重量%)であると断定された。その後、実施例1の溶液73.1g(0.10molの化合物II)を加えた。10分後、水1300gを15分間以内に加えた。次に、5.8g(0.0562mol)のDETA及び2.7g(0.0159mol)のIPDAの混合物を加えた。最終的に、減圧下で蒸留法によってアセトンを除去した。
ジアミノ-モノカルボン酸を用いたPUDの調製(DE-A 2 034 479の開示に類似)
アジピン酸、ネオペンチルグリコール、及び1,6-ヘキサンジオール(モル比1/1)(OH価56)から生成されたポリエステルジオール600g(0.30mol)、ブタノール出発ポリエチレンオキシド26.7g(0.014mol)、アセトン100g、並びにジラウリン酸ジブチル錫0.3gを容器にいれ、83℃で撹拌した。次に、89.8g(0.404mol)のIPDI及び106.7g(0.404mol)のH12MDIを加え、続けて、得られた混合物を、83℃で60分間撹拌した。次に、1,4-ブタンジオール27.0g(0.30mol)を加え、反応を更に120分間継続させた。この混合物にアセトン850gを加えて希釈した。得られた混合物のNCO含有率は、0.93重量%(計算上:0.93重量%)であると断定された。その後、エチレンジアミンに対するアクリル酸ナトリウムの付加物42.0g(0.10mol)を加えた。10分後、水1300gを15分間以内に加えた。次に、5.8g(0.0562mol)のDETA及び2.7g(0.0159mol)のIPDAの混合物を加えた。最終的に、減圧下で蒸留法によってアセトンを除去した。
本発明は、以下の実施形態を包含する。
(実施形態1)
二官能又は多官能イソシアネート、ジオール、1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び場合により、更なる化合物を反応させることによって得られるポリウレタンの水分散液。
(実施形態2)
前記ジカルボン酸塩が、式I
(実施形態3)
Rが、脂環式環系を含む脂肪族炭化水素基を表す、実施形態2に記載の水分散液。
(実施形態4)
前記ジカルボン酸塩のカチオンがアルカリカチオンである、実施形態1から3のいずれか一項に記載の水分散液。
(実施形態5)
前記ジカルボン酸塩が、式II
(実施形態6)
前記ポリウレタンが、
a)炭素原子数4〜30の二官能又は多官能イソシアネート、
b)ジオールであって、
b.1)ジオール(b)の総量に対して10〜100mol%の分子量が、500〜5000であり、
b.2)ジオール(b)の総量に対して0〜90mol%の分子量が、60〜500g/molである、ジオール、
c)1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び
d)場合により、少なくとも1つのイソシアネート基又は少なくとも1つのイソシアネート反応性基を有する化合物であって、化合物a)、b)、及びc)とは異なる化合物
を反応させることによって得られる、実施形態1から5のいずれか一項に記載の水分散液。
(実施形態7)
前記ポリウレタンが、1つ又は2つの第二級アミノ基を有するジカルボン酸塩を、ポリウレタン1kg当たり0.01〜0.5molの量で含む、実施形態1から6のいずれか一項に記載の水分散液。
(実施形態8)
実施形態1から7のいずれか一項に記載の水分散液を製造する方法であって、
I)化合物a)、b)、c)、及び場合により、d)を、有機溶媒中でポリウレタンと反応させ、
II)ポリウレタンを水に分散させ、ここで
イソシアネート反応性基として第一級又は第二級アミノ基を有する成分d)を、I)で反応させてもよく、又はステップIIの間か、若しくはステップIIの後に、部分的に、若しくは全てを加えてもよい、方法。
(実施形態9)
木材、ベニヤ板、紙、板紙、ボール紙、布地、革、不織布、プラスチック表面、ガラス、セラミック、鉱物建材、非被覆金属、又は被覆金属のコーティング又は接着結合のための、実施形態1から8のいずれか一項に記載のポリウレタン分散液の使用。
(実施形態10)
式I
(実施形態11)
式II
Claims (11)
- 二官能又は多官能イソシアネート、ジオール、1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び場合により、更なる化合物を反応させることによって得られるポリウレタンの水分散液。
- Rが、脂環式環系を含む脂肪族炭化水素基を表す、請求項2に記載の水分散液。
- 前記ジカルボン酸塩のカチオンがアルカリカチオンである、請求項1から3のいずれか一項に記載の水分散液。
- 前記ポリウレタンが、
a)炭素原子数4〜30の二官能又は多官能イソシアネート、
b)ジオールであって、
b.1)ジオール(b)の総量に対して10〜100mol%の分子量が、500〜5000であり、
b.2)ジオール(b)の総量に対して0〜90mol%の分子量が、60〜500g/molである、ジオール、
c)1つ又は2つの第二級アミノ基を有するジカルボン酸塩、及び
d)場合により、少なくとも1つのイソシアネート基又は少なくとも1つのイソシアネート反応性基を有する化合物であって、化合物a)、b)、及びc)とは異なる化合物
を反応させることによって得られる、請求項1から5のいずれか一項に記載の水分散液。 - 前記ポリウレタンが、1つ又は2つの第二級アミノ基を有するジカルボン酸塩を、ポリウレタン1kg当たり0.01〜0.5molの量で含む、請求項1から6のいずれか一項に記載の水分散液。
- 請求項1から7のいずれか一項に記載の水分散液を製造する方法であって、
I)化合物a)、b)、c)、及び場合により、d)を、有機溶媒中でポリウレタンと反応させ、
II)ポリウレタンを水に分散させ、ここで
イソシアネート反応性基として第一級又は第二級アミノ基を有する成分d)を、I)で反応させてもよく、又はステップIIの間か、若しくはステップIIの後に、部分的に、若しくは全てを加えてもよい、方法。 - 木材、ベニヤ板、紙、板紙、ボール紙、布地、革、不織布、プラスチック表面、ガラス、セラミック、鉱物建材、非被覆金属、又は被覆金属のコーティング又は接着結合のための、請求項1から8のいずれか一項に記載のポリウレタン分散液の使用。
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PCT/EP2019/059586 WO2019206693A1 (en) | 2018-04-25 | 2019-04-15 | Aqueous dispersion of a polyurethane comprising a dicarboxylate with one or two secondary amino group |
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DE2034479A1 (de) | 1970-07-11 | 1972-01-13 | Bayer | Polyurethan Kunststoffe und Verfahren zu ihrer Herstellung |
DE2035732A1 (de) | 1970-07-18 | 1972-01-27 | Farbenfabriken Bayer AG, 5090 Le verkusen | N (Omega Ammo a/kan) Omega ammo a/kan sulfonsaure salze und ihre Verwendung als anio nische Aufbaukomponente bei der Herstellung von emulgatorfreien Polyurethandispersionen |
FR2345503A1 (fr) * | 1976-03-22 | 1977-10-21 | Oxy Metal Industries Corp | Compositions et procede pour l'enlevement d'alliages de nickel deposes par voie electrolytique |
DE19621027A1 (de) | 1996-05-24 | 1997-11-27 | Basf Ag | Verfahren zur Abtrennung flüchtiger organischer Komponenten aus Suspensionen oder Dispersionen |
DE19750186A1 (de) * | 1997-11-13 | 1999-05-20 | Bayer Ag | Hydrophilierungsmittel, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Dispergator für wäßrige Polyurethan-Dispersionen |
US5968494A (en) * | 1998-02-24 | 1999-10-19 | National Starch And Chemical Investment Holding Corporation | Polyurethanes with carboxylate functionality for hair fixative applications |
US6232406B1 (en) * | 1999-09-30 | 2001-05-15 | Replication Medical Inc. | Hydrogel and method of making |
EP2186841A1 (de) * | 2008-11-14 | 2010-05-19 | Bayer MaterialScience AG | Vernetzbare Polyurethan-Dispersionen |
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LAKSHMI MUTHUSUBRAMANIAN ET AL.: "Synthesis of Quinolines via Cyanoethylation", INDIAN JOURNAL OF CHEMISTRY SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICICAL CHEMISTRY, vol. 26, no. 12, JPN6023018132, 31 December 1987 (1987-12-31), pages 1192 - 1193, ISSN: 0005052409 * |
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WO2019206693A1 (en) | 2019-10-31 |
CN111971265A (zh) | 2020-11-20 |
AU2019259846A1 (en) | 2020-11-19 |
AU2019259846A2 (en) | 2020-11-26 |
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