EP2507279A2 - Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanes - Google Patents
Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanesInfo
- Publication number
- EP2507279A2 EP2507279A2 EP10782305A EP10782305A EP2507279A2 EP 2507279 A2 EP2507279 A2 EP 2507279A2 EP 10782305 A EP10782305 A EP 10782305A EP 10782305 A EP10782305 A EP 10782305A EP 2507279 A2 EP2507279 A2 EP 2507279A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- atoms
- radical
- reactive polyurethane
- reactive
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 125
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 98
- 239000004814 polyurethane Substances 0.000 title claims abstract description 97
- 150000004705 aldimines Chemical class 0.000 title claims abstract description 37
- 238000004140 cleaning Methods 0.000 title claims description 35
- 239000004831 Hot glue Substances 0.000 claims abstract description 24
- 239000012459 cleaning agent Substances 0.000 claims abstract description 13
- 239000003599 detergent Substances 0.000 claims description 56
- -1 Hydrocarbon radical Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229920005862 polyol Polymers 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001622 bismuth compounds Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000009434 installation Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 abstract description 32
- 230000001070 adhesive effect Effects 0.000 abstract description 32
- 230000000694 effects Effects 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000002829 reductive effect Effects 0.000 abstract description 2
- 150000001299 aldehydes Chemical class 0.000 description 35
- 150000001412 amines Chemical class 0.000 description 29
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YRDQAIWXWUHXPQ-UHFFFAOYSA-N (2,2-dimethyl-3-oxopropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)(C)C=O YRDQAIWXWUHXPQ-UHFFFAOYSA-N 0.000 description 6
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 6
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 230000009965 odorless effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 239000002981 blocking agent Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SQFCBBLSKSECMB-UHFFFAOYSA-N 2-(3-aminopropoxy)ethanol Chemical compound NCCCOCCO SQFCBBLSKSECMB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ASDQMECUMYIVBG-UHFFFAOYSA-N 2-[2-(2-aminoethoxy)ethoxy]ethanol Chemical compound NCCOCCOCCO ASDQMECUMYIVBG-UHFFFAOYSA-N 0.000 description 3
- DCZMLYRQHBZWLZ-UHFFFAOYSA-N 2-[2-(3-aminopropoxy)ethoxy]ethanol Chemical compound NCCCOCCOCCO DCZMLYRQHBZWLZ-UHFFFAOYSA-N 0.000 description 3
- SWESRARCMPPTGM-UHFFFAOYSA-N 2-[4-(2-aminoethyl)phenyl]ethanol Chemical compound NCCC1=CC=C(CCO)C=C1 SWESRARCMPPTGM-UHFFFAOYSA-N 0.000 description 3
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 3
- YFEAYNIMJBHJCM-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-ol Chemical compound CC1(C)CC(O)CC(C)(CN)C1 YFEAYNIMJBHJCM-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 3
- GSLKMTUWTDRKOT-UHFFFAOYSA-N 6-(3-aminopropoxy)hexan-1-ol Chemical compound NCCCOCCCCCCO GSLKMTUWTDRKOT-UHFFFAOYSA-N 0.000 description 3
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- FCZQPWVILDWRBN-UHFFFAOYSA-N n'-cyclohexylethane-1,2-diamine Chemical compound NCCNC1CCCCC1 FCZQPWVILDWRBN-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- SWVSKCPPMNGBGL-UHFFFAOYSA-N 10-aminodecan-1-ol Chemical compound NCCCCCCCCCCO SWVSKCPPMNGBGL-UHFFFAOYSA-N 0.000 description 2
- JMKBPENVULMVDP-UHFFFAOYSA-N 10-aminodecane-1-thiol Chemical compound NCCCCCCCCCCS JMKBPENVULMVDP-UHFFFAOYSA-N 0.000 description 2
- IIWXYWWVCBRBCJ-UHFFFAOYSA-N 12-aminododecan-1-ol Chemical compound NCCCCCCCCCCCCO IIWXYWWVCBRBCJ-UHFFFAOYSA-N 0.000 description 2
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 2
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- ANOPCGQVRXJHHD-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC21COC(CCCN)OC2 ANOPCGQVRXJHHD-UHFFFAOYSA-N 0.000 description 2
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 2
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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 2
- HVCYXOVITCKDCK-UHFFFAOYSA-N 4-piperidin-3-ylbutan-1-amine Chemical compound NCCCCC1CCCNC1 HVCYXOVITCKDCK-UHFFFAOYSA-N 0.000 description 2
- WYYXDSQOPIGZPU-UHFFFAOYSA-N 6-aminohexane-1-thiol Chemical compound NCCCCCCS WYYXDSQOPIGZPU-UHFFFAOYSA-N 0.000 description 2
- KYJSXYQQYWMITG-UHFFFAOYSA-N 7-aminoheptan-1-ol Chemical compound NCCCCCCCO KYJSXYQQYWMITG-UHFFFAOYSA-N 0.000 description 2
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- DPNYVVLIXCRDQZ-UHFFFAOYSA-N [5-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine [6-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine Chemical compound NCC1CC2CC1CC2CN.NCC1CC2CC(CN)C1C2 DPNYVVLIXCRDQZ-UHFFFAOYSA-N 0.000 description 2
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- 238000005575 aldol reaction Methods 0.000 description 2
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
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- 230000008901 benefit Effects 0.000 description 2
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- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
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- 230000008878 coupling Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000007278 cyanoethylation reaction Methods 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
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- IDWDEHYPSCTKFU-UHFFFAOYSA-N [3,5-bis(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC(CN)=CC(CN)=C1 IDWDEHYPSCTKFU-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DCFDVJPDXYGCOK-UHFFFAOYSA-N cyclohex-3-ene-1-carbaldehyde Chemical compound O=CC1CCC=CC1 DCFDVJPDXYGCOK-UHFFFAOYSA-N 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexane-carboxaldehyde Natural products O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- WQEXBUQDXKPVHR-PLNGDYQASA-N dimethyl (z)-2-methylbut-2-enedioate Chemical compound COC(=O)\C=C(\C)C(=O)OC WQEXBUQDXKPVHR-PLNGDYQASA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- GBTLMWXVQMOHRC-UHFFFAOYSA-N n'-(1-aminopentan-3-yl)-2-methylpentane-1,5-diamine Chemical compound NCCC(CC)NCCCC(C)CN GBTLMWXVQMOHRC-UHFFFAOYSA-N 0.000 description 1
- VDQVKPUWSIBXEI-UHFFFAOYSA-N n'-(2-ethylhexyl)ethane-1,2-diamine Chemical compound CCCCC(CC)CNCCN VDQVKPUWSIBXEI-UHFFFAOYSA-N 0.000 description 1
- XKXKBRKXBRLPNS-UHFFFAOYSA-N n'-(2-ethylhexyl)propane-1,3-diamine Chemical compound CCCCC(CC)CNCCCN XKXKBRKXBRLPNS-UHFFFAOYSA-N 0.000 description 1
- IRYWPHGCDAOHJJ-UHFFFAOYSA-N n'-(3-aminopropyl)-2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCNCCCN IRYWPHGCDAOHJJ-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- DFPGBRPWDZFIPP-UHFFFAOYSA-N n'-butylethane-1,2-diamine Chemical compound CCCCNCCN DFPGBRPWDZFIPP-UHFFFAOYSA-N 0.000 description 1
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 1
- ADKFRZBUXRKWDL-UHFFFAOYSA-N n'-hexylethane-1,2-diamine Chemical compound CCCCCCNCCN ADKFRZBUXRKWDL-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- LNCZHMKMWWUKHX-UHFFFAOYSA-N nonane-1,3-diamine Chemical compound CCCCCCC(N)CCN LNCZHMKMWWUKHX-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004588 polyurethane sealant Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002235 transmission spectroscopy Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- XJIAZXYLMDIWLU-UHFFFAOYSA-N undecane-1,1-diamine Chemical compound CCCCCCCCCCC(N)N XJIAZXYLMDIWLU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/40—Monoamines or polyamines; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/20—Industrial or commercial equipment, e.g. reactors, tubes or engines
Definitions
- the present invention relates to cleaning compositions for the purification of production and processing plants of reactive polyurethane compositions, in particular of reactive polyurethane hot-melt adhesives.
- Difficulty in processing is mainly in case of business interruptions, such as in the case of short-term mishaps or longer standstills overnight or over the weekend.
- the polyurethane composition remains immobile in the system and it can harden on surfaces, in particular on moving parts or nozzles of
- EP 0 544 058 A2 discloses a detergent composition which, in addition to a non-isocyanate-reactive polyurethane composition, contains a monofunctional alcohol.
- US 5,772,790 discloses a detergent composition which includes a monofunctional amine in addition to a non-curable polyurethane prepolymer.
- amines are hazardous to health and are toxicologically problematic because amines have a corrosive effect.
- the preferred fatty amines are problematic because they are extremely difficult to remove in the case of accidental contact, for example in an accident, with the eyes due to their surfactant character, especially before the corrosive effect arrives.
- working with low molecular weight amines is always associated with an unpleasant odor development.
- WO 2005/052104 A1 discloses a cleaning composition based on an amide or a monofunctional imide.
- Detergent blocked polyurethane composition must be completely removed in order to prevent adhesion problems, especially with respect to thermal stability of the bond. In order to prevent such problems, on the one hand, a process control system must be ensured and, on the other hand, the blocked polyurethane composition must be virtually completely replaced by new reactive polyurethane composition before being taken up again
- Object of the present invention is therefore to provide a detergent composition for the purification of manufacturing
- Processing plants of reactive polyurethane compositions provide that enables a cleaning in which the detergent composition blocked by polyurethane composition does not have to be disposed of completely, but that mixed fractions are also useful for reliable heat stable bonds.
- any fractions taken from the plant after purification could be mixed with the reactive polyurethane composition without problems and could be returned to the production and processing plants without adversely affecting the properties, in particular the thermal stability, of the bonds produced therewith.
- cleanings can be performed that in effect manage without disposing of materials.
- the absence or the at least greatly reduced quantities of waste are economically and ecologically particularly interesting.
- the present invention relates in a first aspect to the use of an aldimine of the formula (I) as a cleaning agent or as a constituent of a detergent composition for the cleaning of production and processing plants of reactive polyurethane compositions, in particular reactive polyurethane urethane hotmelt adhesives.
- Y 1 is a monovalent hydrocarbon radical having 1 to 32 C atoms which optionally contains at least one heteroatom, in particular oxygen in the form of ether, carbonyl or ester atoms.
- E is an (n + 1) -valent hydrocarbon radical having 2 to 12 C atoms, which optionally has at least one heteroatom,
- X stands for O, S or NR 8
- a monovalent hydrocarbon radical having 1 to 20 C atoms which optionally has at least one carboxylic acid ester, nitrile, nitro, phosphonic ester, sulfonic or sulfonic acid ester group,
- n 1, 2 or 3.
- reactive polyurethane composition refers to a polyurethane composition which has free isocyanate groups, in particular polyurethane polymers in the form of isocyanate groups. Isocyanate groups are "reactive", ie they react with water.
- polyurethane polymer encompasses all polymers which are prepared by the so-called diisocyanate-polyaddition process. [Polyurethan Solche] Such polyurethane polymers may contain, in addition to urethane or thiourethane groups, in particular also urea groups.
- polymer in the present document comprises on the one hand a
- the term also encompasses derivatives of such a collective of macromolecules from polyreactions, compounds which have been obtained by reactions, such as additions or substitutions, of functional groups on given macromolecules and which may be chemically uniform or chemically nonuniform.
- the term also includes so-called prepolymers, ie reactive oligomeric pre-adducts whose functional groups are involved in the construction of macromolecules.
- Substance names beginning with "poly” such as polyaldimine, polyamine, polyol or polyisocyanate in the present document refer to substances which formally contain two or more of the functional groups occurring in their name per molecule.
- an amino group in the form of an NH 2 group which is bonded to an organic radical refers to an amino group in which the nitrogen atom is bonded to two organic radicals, which may also be part of a ring together.
- secondary amino group refers to an amino group in which the nitrogen atom is bonded to two organic radicals, which may also be part of a ring together.
- active hydrogen in the present document denotes the hydrogen atom of a hydroxyl, a mercapto or a secondary or primary amino group.
- aliphatic is meant an amine and an isocyanate whose amino and isocyanate groups are each bound exclusively to aliphatic, cycloaliphatic or arylaliphatic radicals, correspondingly these groups are referred to as aliphatic amino and isocyanate groups.
- aromatic is meant an amine and an isocyanate whose amino and isocyanate groups are each bonded to an aromatic radical; correspondingly, these groups are referred to as aromatic amino and amino
- a “low-odor” substance is meant a substance whose smell of human individuals only to a small extent
- odor-free substance is understood to mean a substance that is inconceivable for most human individuals, ie that has no perceptible odor.
- room temperature in the present document is a
- R 1 and R 2 are each a methyl radical.
- n is the value 1.
- R 3 is a hydrogen atom or an alkyl, cycloalkyl, arylalkyl or alkoxycarbonyl radical having 1 to 12 C atoms;
- R 4 is a hydrocarbon radical having 1 to 30 carbon atoms, which optionally contains ether oxygen atoms.
- R 5 is either
- the aldimine of the formula (I) can be prepared from at least one sterically hindered aliphatic aldehyde A and at least one aliphatic amine B, corresponding to the formula [H 2 N] n -E-XH, which, in addition to one or more primary amino groups, also has one further reactive group. which is a hydroxyl group, a mercapto group or NH-R 8 .
- the aldehyde A is used here with respect to the primary amino groups of the amine B stoichiometrically or in stoichiometric excess
- condensation reactions are carried out in the presence of a solvent, by means of which the water formed during the reaction is removed azeotropically, but a preparation process without the use of solvents is preferred for the production of the aldimines of the formula (I) formed in the condensation water is removed directly by applying a vacuum from the reaction mixture.
- the solvent-free production makes it unnecessary to distil off the solvent after the preparation, which simplifies the manufacturing process.
- the aldimine is so free of solvent residues that could cause a disturbing odor.
- At least one sterically hindered ali hatischer aldehyde A of the formula (IV) is used.
- the aldehyde A is preferably odorless. Under one
- “Odorless” substance is understood to mean a substance that is so low in odor that it is not palpable to most human individuals, ie imperceptible to the nose.
- Embodiment Aldeh of the formula (IV a) is a.
- Aldehydes of the formula (IV a) provide ethers of aliphatic, aliphatic or cycloaliphatic 2,2-disubstituted 3-hydroxyaldehydes Alcohols of the formula HO-R 4 , for example fatty alcohols.
- Suitable 2,2-disubstituted 3-hydroxy aldehydes are in turn obtainable from aldol reactions, in particular crossed aldol reactions, between primary or secondary aliphatic aldehydes, in particular formaldehyde, and secondary aliphatic, secondary araliphatic or secondary cycloaliphatic aldehydes, such as, for example, 2-methylbutyraldehyde.
- 2-ethylbutyraldehyde 2-methylvaleraldehyde, 2-ethylcaproic aldehyde, cyclopentane-carboxaldehyde, cyclohexanecarboxaldehyde, 1,2,3,6-tetrahydrobenzaldehyde, 2-methyl-3-phenylpropionaldehyde, 2-phenylpropionaldehyde (hydratropaldehyde) or diphenylacetaldehyde.
- aldehydes of the formula (IV a) are 2,2-dimethyl-3- (2-ethylhexyloxy) -propanal, 2,2-dimethyl-3-lauroxy-propanal and 2,2-dimethyl-3-stearoxy-propanal ,
- Compounds of formula (IV b) are esters of 2,2-disubstituted 3-hydroxy aldehydes already described, such as 2,2-dimethyl-3-hydroxypropanal, 2-hydroxymethyl-2-methyl-butanal, 2-hydroxymethyl-2-ethyl - butanal, 2-hydroxymethyl-2-methyl-pentanal, 2-hydroxymethyl-2-ethyl-hexanal, 1-hydroxymethyl-cyclopentanecarboxaldehyde, 1-hydroxymethylcyclohexanecarboxaldehyde 1-hydroxymethylcyclohex-3-enarboxoxaldehyde, 2-hydroxymethyl- 2-methyl-3-phenyl-propanal, 3-hydroxy-2-methyl-2-phenyl-propanal and 3-hydroxy-2,2-diphenyl-propanal, with suitable carboxylic acids R 5 COOH.
- suitable carboxylic acids R 5 COOH are, on the one hand, aliphatic carboxylic acids, such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, 2-ethyl-caproic acid, capric acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, Nonadecanoic acid, arachidic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid, linolenic acid, elaeostearin acid, arachidonic acid, fatty acids from the technical saponification of natural oils and fats such as rapeseed oil, sunflower oil, linseed oil, olive oil, coconut oil, oil palm kernel oil and oil palm oil, as well as technical mixtures of fatty acids containing such acids.
- suitable carboxylic acids R 5 COOH are aromatic carboxylic acids, for example benzoic acid or the positionally isomeric toluenes, ethyl or isopropyl or tert-butyl or methoxy or nitrobenzoic acids.
- Preferred aldehydes of the formula (IVb) are 2,2-dimethyl-3-lauroyloxypropanal, 2,2-dimethyl-3-myristoyloxypropanal 2,2-dimethyl-3-palmitoyloxypropanal, 2,2-dimethyl-3- stearoyloxypropanal and 2,2-dimethyl-3-benzoyloxypropanal, as well as analogous esters of other 2,2-disubstituted 3-hydroxyaldehydes.
- R 5 is selected from the group consisting of phenyl and the Cn, C13, C15 and C17 alkyl groups.
- aliphatic hydroxyamines such as 2-aminoethanol, 2-methylaminoethanol, 1-amino-2-propanol, 3-amino-1-propanol, 4-amino-1-butanol, 4-amino-2-butanol, 2-amino-2- methylpropanol, 5-amino-1-pentanol, 6-amino-1-hexanol, 7-amino-1-heptanol, 8-amino-1-octanol, 10-amino-1-decanol, 12-amino-1-dodecanol, 4- (2-aminoethyl) -2-hydroxyethylbenzene, 3-amino-methyl-3,5,5-trimethylcyclohexanol; a primary amino-bearing derivatives of glycols such as diethylene glycol, dipropylene glycol, dibutylene glycol and higher oligomers and polymers of these glycols, for example 2- (2-a
- Aliphatic mercaptoamines such as 2-aminoethanethiol (cysteamine), 3-aminopropanethiol, 4-amino-1-butanethiol, 6-amino-1-hexanethiol, 8-amino-1-octanothiol, 10-amino-1-decanethiol , 12-amino-1-dodecanethiol; Aminothio sugars such as 2-amino-2-deoxy-6-thioglucose;
- - di- or polyhydric aliphatic amines which in addition to one or more primary amino groups carry a secondary amino group, such as N-methyl-1, 2-ethanediamine, N-ethyl-1, 2-ethanediamine, N-butyl-1, 2-ethanediamine , N-hexyl-1,2-ethanediamine, N- (2-ethylhexyl) -1, 2-ethanediamine, N-cyclohexyl-1,2-ethanediamine, 4-aminomethylpiperidine, 3- (4-aminobutyl) piperidine , N-aminoethyl-piperazine, diethylenetriamine (DETA), bis-hexamethylenetriamine (BHMT); Di- and triamines from the cyanoethylation or cyanobutylation of primary mono- and diamines, for example N-methyl-1,3-propanediamine, N-ethyl-1,3-propanediamine, N-butyl-1,3-propan
- Aminopentyl) -1,3-pentanediamine N5- (3-aminopropyl) -2-methyl-1,5-pentanediamine, N5- (3-amino-1-ethylpropyl) -2-methyl-1,5-pentanediamine and fatty diamines such as N-cocoalkyl-1,3-propanediamine, N-oleyl-1,3-propanediamine, N-oxyalkyl-1,3-propanediamine, N-tallowalkyl-1,3-propanediamine or N- (C16 -22-alkyl) - 1, 3-propanediamine, as for example under the trade name
- Duomeen® ® from Akzo Nobel are available; the products of the Michael-like addition of aliphatic primary di- or polyamines with acrylonitrile, maleic or fumaric diesters, citraconic diesters, acrylic and methacrylic acid esters and itaconic diesters, reacted in a molar ratio of 1: 1.
- Preferred aliphatic hydroxy and mercaptoamines are those in which the primary amino group of the hydroxyl or mercapto group by a chain of at least 5 atoms, or by a Ring, are separate, as for example in 5-amino-1-pentanol, 6-amino-1-hexanol, 7-amino-1-heptanol, 8-amino-1-octanol, 10-amino-1-decanol, 12-amino-1-dodecanol, 4- (2-aminoethyl) -2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethyl-cyclohexanol, 2- (2-aminoethoxy) -ethanol, triethylene glycol monoamine, a- (2-hydroxymethylethyl) -ro- (2-aminomethylethoxy) -poly (oxy (methyl-1,2-ethanediyl)), 3- (2-hydroxyethoxy)
- Preferred amine B of the formula [H 2 N] n -E-XH are, on the one hand, di- or polyhydric aliphatic amines which, in addition to one or more primary amino groups, carry a secondary amino group, in particular N-methyl-1,2-ethanediamine, N- Ethyl 1,2-ethanediamine, N-cyclohexyl-1,2-ethanediamine, N-methyl-1,3-propanediamine, N-ethyl-1,3-propanediamine, N-butyl-1,3-propanediamine, N-cyclohexyl-1,3-propanediamine, 4-aminomethylpiperidine, 3- (4-aminobutyl) piperidine, DETA, DPTA, BHMT and fatty diamines such as N-cocoalkyl-1,3-propanediamine, N-oleyl-1, 3-propanediamine, N-soyalkyl-1,3-propanediamine and N-tallowalkyl
- aliphatic hydroxy and mercaptoamines in which the primary amino group of the hydroxy or the mercapto group by a chain of at least 5 atoms, or by a ring, are separated, in particular 5-amino-1 - pentanol, 6-amino 1-hexanol and higher homologs thereof, 4- (2-aminoethyl) -2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 2- (2-aminoethoxy) ethanol, triethylene glycol monoamine and higher oligo and polymers thereof, 3- (2-hydroxyethoxy) propylamine, 3- (2- (2-hydroxyethoxy) ethoxy) propylamine, and 3- (6-hydroxyhexyloxy) propylamine.
- the amine B is selected from the group consisting of bis-hexamethylenetriamine (BHMT), N-cyclohexyl-1,2-ethanediamine, N-cyclohexyl-1,3-propanediamine, and 2- (2-aminoethoxy) -ethanol.
- BHMT bis-hexamethylenetriamine
- N-cyclohexyl-1,2-ethanediamine N-cyclohexyl-1,3-propanediamine
- 2- (2-aminoethoxy) -ethanol 2- (2-aminoethoxy
- the reaction between an aldehyde A and an amine B leads to hydroxyaldimines when amine B is a hydroxyamine; to mercaptoaldimines, when a mercaptoamine is used as amine B; to aminoaldimines, when as the amine B is a di- or polyvalent amine, which in addition to one or more primary amino groups is a secondary
- Carries amino groups is used.
- the aldimines of the formula (I) have a substituent NR 8 as substituent X.
- aldimines of the formula (I) in which X is the radical NR 8 and R 8 is a monovalent hydrocarbon radical of the formula (IX) or (IX ') are formed.
- R 9 is a radical which is selected from the group consisting of -COOR 13 , -CN, -NO 2, -PO (OR 13 ) 2 , -SO 2 R 13 and -SO 2OR 13 and R 10 represent a hydrogen atom or a radical selected from the group consisting of -R 13 , -COOR 13 and
- R 13 is a monovalent hydrocarbon radical having 1 to 20 C atoms.
- the amine C is an aliphatic amine having at least two primary amino groups.
- aliphatic primary amine refers to an aliphatic amine in which the amino group is a primary amino group.
- Suitable amines C of the formula [H 2 N] n -E-NH 2 are aliphatic polyamines such as ethylenediamine, 1, 2 and 1, 3-propanediamine, 2-methyl-1, 2-propanediamine, 2,2-dimethyl -1, 3-propanediamine, 1, 3- and 1, 4-butanediamine, 1, 3- and 1, 5-pentanediamine, 2-butyl-2-ethyl-1, 5-pentanediamine, 1, 6-hexamethylenediamine (HMDA), 2,2,4- and 2,4,4-trimethylhexamethylenediamine and mixtures thereof (TMD), 1, 7-heptanediamine, 1, 8-octanediamine, 2,4-dimethyl-1,8-octanediamine, 4 -Aminomethyl-1,8-octanediamine, 1,9-nonanediamine, 2-methyl-1,9-nonanediamine, 5-methyl-1,9-nonanediamine, 1,10-decanediamine, isodecanediamine, 1,
- H 12 MDA bis (4-amino-3-methylcyclohexyl) methane
- TMCDA 2,2,6-trimethylcyclohexane
- MXDA 1,3-xylylenediamine
- PXDA 4-xylylenediamine
- ether group containing aliphatic polyamines such as bis (2-aminoethyl) ether, 4,7-Dioxadecan- 1, 10-diamine, 4,9-dioxadodecane-1, 12-diamine and higher oligomers thereof, polyoxyalkylene polyannynes having theoretically two or three amino groups available (for example under the name Jeffamine ® manufactured by
- di- or triamines in which the primary amino groups are separated by a chain of at least 5 atoms, or by a ring, in particular 1, 5-diamino-2-methylpentane, 1, 6-hexamethylenediamine, 2,2 , 4- and 2,4,4-trimethylhexamethylenediamine and
- Maleic or fumaric diesters such as dimethyl maleate, diethyl maleate, butyl maleate, diethyl fumarate; Citraconic diesters such as dimethyl citraconate; Acrylic or methacrylic acid esters such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofuryl (meth) acrylate, isobornyl (meth) acrylate; Itaconic diesters such as dimethyl itaconate; Cinnamic acid esters such as methyl cinnamate; Vinylphosphonklarediester such as dimethyl vinylphosphonate; Vinylsulfonic acid esters, in particular vinylsulfonic acid aryl esters; vinyl sulfones; Vinyl nitriles such as acrylonitrile, 2-pentenenitrile or fumaronit
- the reaction of the aldehyde A with the amine C to the intermediate of the formula (VII) is carried out in a condensation reaction with elimination of water, as described above for the reaction of the aldehyde A with the amine B.
- the stoichiometry between the aldehyde A and the amine C is chosen so that at least 1 mol of amine C are used per mole of aldehyde A.
- a solvent-free preparation process is preferred, wherein the water formed during the condensation by means of application of
- Michael acceptor of the formula (VIII) takes place, for example, by mixing the intermediate product with a stoichiometric or slightly more than stoichiometric amount of the Michael acceptor of the formula (VIII) and mixing the mixture at from 20.degree Sales of the intermediate to the aldimine of the formula (I) is heated.
- the reaction is preferably carried out without the use of solvents.
- R 3 is preferably H.
- the substituent E preferably has 3 to 6 C-aromas.
- Preferred aldimines of the formula (I) are low in odor. Particularly preferred aldimines of the formula (I) are odorless.
- Y 1 is the radical of the formula (III a) and R 4 is a linear or branched alkyl radical having 6 to 30, in particular 1 1 to 30, carbon atoms.
- Y 1 is the radical of the formula (III b) and R 5 is a linear or branched alkyl radical having 6 to 30, in particular 1 1 to 30, carbon atoms.
- Particularly preferred aldimines of the formula (I) have the structure of -1) or (IIIb-2) or (IIIb-3) or (IIIb-4).
- aldimine of the formula (I) can be used alone as a cleaning agent or as a constituent of a detergent composition for reactive polyurethane compositions.
- Reactive polyurethane compositions have reactive NCO groups.
- the XH group reacts with the isocyanate groups of the reactive polyurethane compositions, i. the NCO groups are blocked so that the thus blocked polyurethane compositions have no free NCO groups.
- the aldimine of the formula (I) have only one group XH.
- crosslinking would take place in such a reaction with the isocyanate groups and purification would no longer be possible, but a similar type of bonding or curing would take place, as in the reaction of the reactive polyurethane compositions (without
- a detergent composition for the purification of manufacturing and processing plants of reactive polyurethane compositions, in particular reactive polyurethane hot melt adhesives represents a further aspect of the present invention.
- Such a detergent composition contains in particular
- At least one carrier A which carries no isocyanate-reactive functional groups.
- a “carrier” means polymers which are thermoplastic and contain the compound B in the
- the carrier A As a carrier A different materials come into question, but the carrier A must be thermoplastic and must not have isocyanate-reactive groups. Furthermore, the carrier A should advantageously at the application temperature with the reactive to be displaced
- Polyurethane hot melt adhesive comparable viscosity.
- a suitable non-reactive carrier A is in particular a blocked polyurethane prepolymer, a hydrocarbon resin, a blocked polyester, a blocked polyol or a copolymer of at least one the monomers which are selected from the group consisting of
- Suitable non-reactive polyurethanes are, for example, stoichiometrically blocked polyurethane prepolymers, which are provided with a
- Blocking agents are rendered inert.
- polyurethane prepolymers containing isocyanate groups can be blocked with blocking agents such as ⁇ -caprolactam or monofunctional alcohols or amines or mercaptans.
- OH prepolymers containing polyurethane prepolymers can be blocked by monofunctional isocyanates, in particular p-tosyl isocyanate.
- Polyurethane used which consists of the reactive to be displaced
- Polyurethane hot melt adhesive whose reactive isocyanate groups have been blocked with a monofunctional alcohol, amine, mercaptan, amide or imide.
- the carrier agent is the isocyanate-free reaction product of the previously described aldehyde of the formula (I) and of an isocyanate group-containing
- Polyurethane polymers in particular those of the reactive polyurethane composition to be purified.
- Such an isocyanate group-free reaction product is preferably carried out with a stoichiometric OH / NCO excess of aldehyde of the formula (I).
- a certain amount of unreacted aldehyde of the formula (I) remains present.
- etherified polyols are suitable.
- the polyol skeleton of this etherified polyol is in particular selected from the group comprising polyether polyols, polyester polyols, polycaprolactone polyols.
- these are dialkoxypolyalkoxydiols, preferably dimethoxypolyethyleneglycols or dimethoxypolypropyleneglycols, or alkoxy-polyesterpolyols.
- polyester polyols have neither free hydroxyl groups nor free carboxyl groups.
- Polyester polyols polycarbonate polyols, polyhydroxy-terminated polybutadiene polyols, polyether polyols, in particular polyoxyalkylene polyols, which are stoichiometrically blocked with a monofunctional isocyanate compound, so that neither free hydroxyl groups nor free carboxyl groups are present.
- carrier A Also suitable as carrier A are rosin, hydrocarbon resins, hydrogenated or non-hydrogenated terpene resins and petroleum resins.
- Suitable homo- or copolymers are thermoplastic homo- or
- EVA ethylene / vinyl acetate copolymers
- Ethylene / vinyl acetate copolymers have proven to be particularly suitable as carriers.
- the ethylene / vinyl acetate copolymers are distinguished above all by a low price and wide commercial availability. Contrary to the expert opinion, as it is expressed, for example, in EP 0 544 058 A2, it has been found that EVA is very miscible with polyurethane adhesives and is therefore suitable for use as a carrier material for a detergent composition.
- the carrier A advantageously has a glass transition temperature (T g ) which is lower than the application temperature of the detergent composition.
- T g glass transition temperature
- the carrier A is selected in particular such that the polarity of the carrier A is matched to that of the hot melt adhesive to be displaced. Because polyurethane hotmelt adhesives should preferably have polar character, this means that especially polar carriers A are preferred.
- the detergent composition further comprises a dye or a pigment.
- Dyes which are present in dissolved form in the vehicle A are preferably used. Such a dye makes it easier to visually judge whether and how much of the mixed fraction needs to be discarded.
- the detergent composition further contains a dye or a pigment to visually easily detect when the process of blocking the reactive polyurethane composition by the detergent composition is completed.
- the proportion of the carrier A should not be too high. It has been found that the proportion of the carrier A is advantageously not more than 50% by weight, in particular between 5 and 30% by weight, based on the detergent composition.
- the cleaning composition further comprises at least one catalyst for the reaction of the group HX with isocyanate, in particular an organotin compound and / or a bismuth compounds and / or a tertiary amine.
- organotin compounds are well known to the person skilled in the art, for example dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, dibutyltin diacetylacetonate or dioctyltin dilaurate.
- Such bismuth compounds are known to the person skilled in the art, for example bismuth trioctoate or bismuth tris (neodecanoate).
- the detergent composition may further contain fillers if desired. However, to avoid damage to equipment and equipment, these fillers should not be abrasive, as a rule. Detergent compositions containing no fillers are preferred.
- the detergent composition may optionally contain other ingredients such as plasticizers, stabilizers, in particular
- Heat stabilizers such as surfactants, as they occur in conventional detergents.
- plasticizers There are limits to the use of plasticizers. At high levels or certain types, there is the disadvantage that, due to migration effects, a softener-containing detergent composition will become greasy on storage and therefore difficult to handle.
- the optional ingredients of the detergent composition should be chosen so that they have no functional groups that do not react with isocyanates, especially at the cleaning temperature.
- the previously described aldimine of the formula (I) or the previously described detergent composition is particularly suitable for cleaning production and processing plants of reactive polyurethane compositions, in particular of reactive polyurethane hot-melt adhesives
- a further aspect of the present invention therefore relates to a process for purifying a preparation or application plant or an application device of reactive polyurethane compositions.
- the invention may relate to any reactive polyurethane composition as long as it has isocyanate groups.
- These reactive polyurethane compositions are particularly useful as adhesives or sealants or cast resin or coating.
- polyurethane reactive compositions based on isocyanate group-containing polyurethane polymers.
- isocyanate group-containing polyurethane polymers are prepared in a known manner from polyols and polyisocyanates.
- the present invention is important on the one hand for one-component reactive polyurethane sealants or adhesives based on polyurethane polymers containing isocyanate groups, which are applied at room temperature and cure with atmospheric moisture.
- sealants or adhesives are commercially available, for example, under the trademarks Sikaflex® or SikaTack® from Sika Nurse AG.
- the present invention is particularly important for one-component reactive polyurethane adhesives based on polyurethane polymers containing isocyanate groups, which are applied at a higher temperature and cure with atmospheric moisture.
- adhesives are also known as Warmmelt polyurethane adhesives (application temperature 50 ° to 80 ° C) or reactive polyurethane hotmelt adhesives (reactive polyurethane hotmelts) (application temperature greater than 80 ° C).
- Reactive polyurethane hotmelt adhesives reactive polyurethane hotmelts
- Such reactive polyurethane hot-melt adhesives are commercially available, for example, from Sika Automotive GmbH, Germany, under the trade name SikaMelt®.
- the aldehyde of formula (I), or the detergent composition at least for the time of cleaning at
- the aldehyde or the detergent composition can remain at the cleaning temperature for at least a few hours, in particular days, without the aldehyde or the detergent composition being decomposed or decomposed in substantial proportions.
- the aldehyde or the detergent composition is advantageously as free of water or moisture as possible. It should therefore be used in the production of dry or dried as possible raw materials and water-absorbing ingredients are omitted from the environment. Such a cleaning agent is extremely efficient, cost-effective and ecologically and work hygiene extremely beneficial.
- the detergent composition can be put into the proper dosage form as needed for the application.
- a dosage form in solid form is advantageous. It can be used as granules, for example
- the detergent composition is transferred directly after preparation from the melt in the application form.
- packaging used for the aldehyde or the detergent composition offers adequate protection and, in particular, should be moisture-impermeable.
- the addition in the system to be cleaned or the device to be cleaned should be done especially in hot melt adhesives in solid form or in the form of a melt. It is preferred if the detergent composition is in granulate or flake form.
- the cleaning temperature is usually the processing temperature of the reactive polyurethane hotmelt adhesive, typically 80 to 180 ° C, especially 90 to 150 ° C. However, it may be advantageous to carry out the cleaning at a higher temperature so that the reactive hot-melt polyurethane adhesive to be displaced becomes more viscous. However, due to the decomposition temperature of the polyurethane hot-melt adhesive or of the detergent composition, system-related upper limits are present which must not be exceeded under any circumstances.
- This time can either be determined visually, if the
- Detergent composition contains a suitably selected dye or pigment.
- this time can be determined by infrared absorption or transmission spectroscopy, namely when the IR band characteristic of the NCO group (2270 cm -1 ) has disappeared the particular specific reactive polyurethane composition in combination with fixed equipment parameters can be used for reliable blocking of a time previously determined for this combination
- the equipment thus cleaned or the apparatus thus cleaned can easily be left unused for a long time.
- Polyurethane composition is present. It has been shown by experience that a reliably usable mixed fraction should have a maximum of 30% by weight of aldimine of the formula (I) blocked polyurethane polymer. However, it is a great advantage of the present invention that these removed amount of the reactive polyurethane composition can be added without problems before being fed to the plant, so that virtually no waste is produced thanks to this recycling.
- the aldehyde of the formula (I) and the detergent composition is particularly suitable for cleaning processing plants and application equipment, in particular application equipment, reactive polyurethane compositions, in particular reactive polyurethane. Hot melt adhesives. Typically, these systems and devices have narrowing parts such as slots or nozzles, moving parts such as
- detergent compositions can also be used for cleaning installations in which reactive polyurethane compositions are produced.
- Infrared spectra were measured on a Perkin-Elmer 1600 FT-IR instrument (ZnSe crystal horizontal ATR measuring unit); the samples were applied undiluted as films. The absorption bands are given in wavenumbers (cm -1 ) (measurement window: 4000-650 cm -1 ).
- the viscosity was measured on a thermostatically controlled cone-plate viscometer Physica UM (cone diameter 20 mm, cone angle 1 °, cone tip-plate distance 0.05 mm, shear rate 10 to 1000 s -1 ).
- amine content The total content of aldimino groups and free amino groups in the compounds prepared ("amine content") was determined by titration (with 0.1 N HCIO 4 in glacial acetic acid, against crystal violet) and is always given in mmol NH 2 / g (even if it is not only primary amino groups are involved).
- IR: 3435br (OH), 2954sh, 2922, 2852, 1736 (CO), 1668 (C N), 1466, 1418, 1394, 1375, 1248, 1233, 1160, 1 127, 1062, 1022, 933, 893, 813, 721.
- An exemplary reactive hot melt polyurethane adhesive K1 was prepared as follows:
- the above-described reactive hot-melt adhesive K1 was applied via a roll application ICO WLA 1600 (ICO System, Germany).
- ICO WLA 1600 ICO System, Germany
- a graphitized roller a gap of less than 1 mm and an adhesive temperature of 145 ° C was used.
- the application speed was 6 m / min.
- the rotational speed of the doctor roller was 0.6 m / min.
- the tensile shear specimens were prepared by means of a mold: The adhesive was applied to a small piece of dried beech (100 mm x 25 mm x 5 mm) with a second such beech chip to a thickness of 1 mm and 20 mm overlap by means of a suitable mold in the shear shear test specimens. Compressed geometry and cured for 7 days at 23 ° C and 50% relative humidity.
- the supply of the adhesive K1 was separated for a short time, in each case per kg of the adhesive 200 g of the respective aldimine or the alcohol according to Table 1 supplied as a cleaning agent in the nip. It was continuously sampled to detect the disappearance of IR via IR
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10782305A EP2507279A2 (fr) | 2009-12-02 | 2010-11-26 | Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanes |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09177687A EP2330140A1 (fr) | 2009-12-02 | 2009-12-02 | Composition de nettoyage à base d'aldimines pour compositions réactives de polyuréthane. |
EP10782305A EP2507279A2 (fr) | 2009-12-02 | 2010-11-26 | Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanes |
PCT/EP2010/068267 WO2011067168A2 (fr) | 2009-12-02 | 2010-11-26 | Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanes |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2507279A2 true EP2507279A2 (fr) | 2012-10-10 |
Family
ID=42041530
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09177687A Withdrawn EP2330140A1 (fr) | 2009-12-02 | 2009-12-02 | Composition de nettoyage à base d'aldimines pour compositions réactives de polyuréthane. |
EP10782305A Withdrawn EP2507279A2 (fr) | 2009-12-02 | 2010-11-26 | Composition de nettoyage à l'aldimine pour des compositions réactives de polyuréthanes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09177687A Withdrawn EP2330140A1 (fr) | 2009-12-02 | 2009-12-02 | Composition de nettoyage à base d'aldimines pour compositions réactives de polyuréthane. |
Country Status (6)
Country | Link |
---|---|
US (1) | US8673089B2 (fr) |
EP (2) | EP2330140A1 (fr) |
KR (1) | KR20120127575A (fr) |
CN (1) | CN102648226A (fr) |
BR (1) | BR112012012989A2 (fr) |
WO (1) | WO2011067168A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102719325B (zh) * | 2012-06-26 | 2014-05-14 | 中国科学院理化技术研究所嘉兴工程中心 | 一种新型的反应型聚氨酯热熔胶清洗剂 |
CN102746488B (zh) * | 2012-07-18 | 2015-03-11 | 武汉工程大学 | 衣康酸二苯甲酯改性的多元胺固化剂及其制备方法 |
US20200172651A1 (en) * | 2017-07-20 | 2020-06-04 | Dic Corporation | Release agent for reactive hot melt resin |
CN110655900A (zh) * | 2019-10-24 | 2020-01-07 | 上海昀通电子科技有限公司 | 紫外光固化清洁胶、制备方法及其用途 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE9114780U1 (de) | 1991-11-27 | 1992-02-13 | H.B. Fuller Licensing & Financing, Inc., Wilmington, Del. | Reinigungscompound |
US5772790A (en) | 1996-06-26 | 1998-06-30 | Reichhold Chemicals, Inc. | Methods and compositions for removing HMPUR residues |
US20040028613A1 (en) | 2001-06-25 | 2004-02-12 | Nastech Pharmaceutical Company Inc | Dopamine agonist formulations for enhanced central nervous system delivery |
EP1384709A1 (fr) * | 2002-07-26 | 2004-01-28 | Sika Technology AG | Polyaldimines |
EP1535990A1 (fr) * | 2003-11-25 | 2005-06-01 | Sika Tivoli GmbH | Composition de nettoyage |
EP1770107A1 (fr) * | 2005-09-30 | 2007-04-04 | Sika Technology AG | Composition de polyuréthanne durcissant par l'humidité |
EP2017260A1 (fr) * | 2007-07-16 | 2009-01-21 | Sika Technology AG | Aldimine et aldimine contenant des compositions |
-
2009
- 2009-12-02 EP EP09177687A patent/EP2330140A1/fr not_active Withdrawn
-
2010
- 2010-11-26 KR KR1020127016019A patent/KR20120127575A/ko not_active Application Discontinuation
- 2010-11-26 CN CN2010800544833A patent/CN102648226A/zh active Pending
- 2010-11-26 WO PCT/EP2010/068267 patent/WO2011067168A2/fr active Application Filing
- 2010-11-26 BR BR112012012989A patent/BR112012012989A2/pt not_active IP Right Cessation
- 2010-11-26 US US13/513,466 patent/US8673089B2/en not_active Expired - Fee Related
- 2010-11-26 EP EP10782305A patent/EP2507279A2/fr not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO2011067168A2 * |
Also Published As
Publication number | Publication date |
---|---|
CN102648226A (zh) | 2012-08-22 |
WO2011067168A2 (fr) | 2011-06-09 |
US8673089B2 (en) | 2014-03-18 |
EP2330140A1 (fr) | 2011-06-08 |
KR20120127575A (ko) | 2012-11-22 |
US20120245069A1 (en) | 2012-09-27 |
BR112012012989A2 (pt) | 2019-09-24 |
WO2011067168A3 (fr) | 2011-11-10 |
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