DE2434953A1 - Waermestabile harze - Google Patents
Waermestabile harzeInfo
- Publication number
- DE2434953A1 DE2434953A1 DE2434953A DE2434953A DE2434953A1 DE 2434953 A1 DE2434953 A1 DE 2434953A1 DE 2434953 A DE2434953 A DE 2434953A DE 2434953 A DE2434953 A DE 2434953A DE 2434953 A1 DE2434953 A1 DE 2434953A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- bis
- group
- imine
- 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.)
- Ceased
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 85
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 2
- 150000002466 imines Chemical class 0.000 claims abstract description 38
- 239000000376 reactant Substances 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- -1 amino compound Chemical class 0.000 claims description 116
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229920001228 polyisocyanate Polymers 0.000 claims description 28
- 239000005056 polyisocyanate Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 11
- 229920006305 unsaturated polyester Polymers 0.000 claims description 10
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000000879 imine group Chemical group 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 150000001412 amines Chemical class 0.000 abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000010292 electrical insulation Methods 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 65
- 150000003254 radicals Chemical class 0.000 description 60
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 23
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 150000002009 diols Chemical class 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 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 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 201000006747 infectious mononucleosis Diseases 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- OVAMCIQDVMEHAG-UHFFFAOYSA-N n-benzhydryl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1C=NC(C=1C=CC=CC=1)C1=CC=CC=C1 OVAMCIQDVMEHAG-UHFFFAOYSA-N 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- PWMKGBSQKVTNNH-UHFFFAOYSA-N C(C=1C(O)=CC=CC=1)=C1CC(=C(C=C1)CC1=C(CC(C=C1)=CC=1C(O)=CC=CC=1)N)N Chemical compound C(C=1C(O)=CC=CC=1)=C1CC(=C(C=C1)CC1=C(CC(C=C1)=CC=1C(O)=CC=CC=1)N)N PWMKGBSQKVTNNH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 2
- 229920001744 Polyaldehyde Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004146 Propane-1,2-diol Substances 0.000 description 2
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Classifications
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- 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
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7326581A FR2278722A1 (fr) | 1973-07-19 | 1973-07-19 | Resines thermostables |
| FR7401916A FR2271250A2 (en) | 1974-01-21 | 1974-01-21 | Heat stable polymers based on maleimide cpd. - reacted with an amino cpd. and a carbonyl cpd. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2434953A1 true DE2434953A1 (de) | 1975-02-06 |
Family
ID=26217848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2434953A Ceased DE2434953A1 (de) | 1973-07-19 | 1974-07-19 | Waermestabile harze |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5054697A (https=) |
| AT (1) | AT343909B (https=) |
| BR (1) | BR7405955D0 (https=) |
| CA (1) | CA1052042A (https=) |
| CH (1) | CH592697A5 (https=) |
| DE (1) | DE2434953A1 (https=) |
| IT (1) | IT1017306B (https=) |
| LU (1) | LU70561A1 (https=) |
| NL (1) | NL7409399A (https=) |
| SE (1) | SE7409398L (https=) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039156A1 (en) * | 1980-04-22 | 1981-11-04 | Minnesota Mining And Manufacturing Company | One-part solvent-free thermosettable prepolymer composition |
| US8410066B2 (en) | 2009-05-01 | 2013-04-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
| US20150087759A1 (en) * | 2013-09-23 | 2015-03-26 | Milliken & Company | Thermoplastic polymer composition |
| US9109002B2 (en) | 2011-12-22 | 2015-08-18 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US9193845B2 (en) | 2013-09-23 | 2015-11-24 | Milliken & Company | Thermoplastic polymer composition |
| US9200142B2 (en) | 2013-09-23 | 2015-12-01 | Milliken & Company | Thermoplastic polymer composition |
| US9200144B2 (en) | 2013-09-23 | 2015-12-01 | Milliken & Company | Thermoplastic polymer composition |
| US9580575B2 (en) | 2013-09-23 | 2017-02-28 | Milliken & Company | Polyethylene articles |
| US9867841B2 (en) | 2012-12-07 | 2018-01-16 | Glycomimetics, Inc. | Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells |
| US10519181B2 (en) | 2014-12-03 | 2019-12-31 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| US11072625B2 (en) | 2016-10-07 | 2021-07-27 | Glycomimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| US11197877B2 (en) | 2017-03-15 | 2021-12-14 | Glycomimetics. Inc. | Galactopyranosyl-cyclohexyl derivauves as E-selectin antagonists |
| US11291678B2 (en) | 2016-03-02 | 2022-04-05 | Glycomimetics, Inc | Methods for the treatment and/or prevention of cardiovascular disease by inhibition of E-selectin |
| US11433086B2 (en) | 2016-08-08 | 2022-09-06 | Glycomimetics, Inc. | Combination of T-cell checkpoint inhibitors with inhibitors of e-selectin or CXCR4, or with heterobifunctional inhibitors of both E-selectin and CXCR4 |
| US11548908B2 (en) | 2017-12-29 | 2023-01-10 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| US11707474B2 (en) | 2018-03-05 | 2023-07-25 | Glycomimetics, Inc. | Methods for treating acute myeloid leukemia and related conditions |
| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03162450A (ja) * | 1989-11-21 | 1991-07-12 | Nitto Denko Corp | 熱硬化性樹脂組成物 |
| BR0010655A (pt) * | 1999-03-24 | 2002-02-13 | Anormed Inc | Compostos heterocìclicos para ligação ao receptor de quimiocina |
-
1974
- 1974-07-11 NL NL7409399A patent/NL7409399A/xx not_active Application Discontinuation
- 1974-07-15 JP JP49081043A patent/JPS5054697A/ja active Pending
- 1974-07-18 LU LU70561A patent/LU70561A1/xx unknown
- 1974-07-18 BR BR595574A patent/BR7405955D0/pt unknown
- 1974-07-18 SE SE7409398A patent/SE7409398L/ not_active Application Discontinuation
- 1974-07-18 CA CA205,245A patent/CA1052042A/fr not_active Expired
- 1974-07-18 CH CH991974A patent/CH592697A5/xx not_active IP Right Cessation
- 1974-07-19 DE DE2434953A patent/DE2434953A1/de not_active Ceased
- 1974-07-19 AT AT600074A patent/AT343909B/de not_active IP Right Cessation
- 1974-07-19 IT IT2537974A patent/IT1017306B/it active
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039156A1 (en) * | 1980-04-22 | 1981-11-04 | Minnesota Mining And Manufacturing Company | One-part solvent-free thermosettable prepolymer composition |
| US8410066B2 (en) | 2009-05-01 | 2013-04-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
| US9796745B2 (en) | 2011-12-22 | 2017-10-24 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US11987598B2 (en) | 2011-12-22 | 2024-05-21 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US9109002B2 (en) | 2011-12-22 | 2015-08-18 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US11332491B2 (en) | 2011-12-22 | 2022-05-17 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US10766916B2 (en) | 2011-12-22 | 2020-09-08 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US10526361B2 (en) | 2011-12-22 | 2020-01-07 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| US9867841B2 (en) | 2012-12-07 | 2018-01-16 | Glycomimetics, Inc. | Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells |
| US9193845B2 (en) | 2013-09-23 | 2015-11-24 | Milliken & Company | Thermoplastic polymer composition |
| US9200144B2 (en) | 2013-09-23 | 2015-12-01 | Milliken & Company | Thermoplastic polymer composition |
| US9200142B2 (en) | 2013-09-23 | 2015-12-01 | Milliken & Company | Thermoplastic polymer composition |
| US9580575B2 (en) | 2013-09-23 | 2017-02-28 | Milliken & Company | Polyethylene articles |
| US20150087759A1 (en) * | 2013-09-23 | 2015-03-26 | Milliken & Company | Thermoplastic polymer composition |
| US9120914B2 (en) | 2013-09-23 | 2015-09-01 | Milliken & Company | Thermoplastic polymer composition |
| US10519181B2 (en) | 2014-12-03 | 2019-12-31 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| US11291678B2 (en) | 2016-03-02 | 2022-04-05 | Glycomimetics, Inc | Methods for the treatment and/or prevention of cardiovascular disease by inhibition of E-selectin |
| US11433086B2 (en) | 2016-08-08 | 2022-09-06 | Glycomimetics, Inc. | Combination of T-cell checkpoint inhibitors with inhibitors of e-selectin or CXCR4, or with heterobifunctional inhibitors of both E-selectin and CXCR4 |
| US11072625B2 (en) | 2016-10-07 | 2021-07-27 | Glycomimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| US11780873B2 (en) | 2016-10-07 | 2023-10-10 | Glycomimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| US11878026B2 (en) | 2017-03-15 | 2024-01-23 | Glycomimetics, Inc. | Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists |
| US11197877B2 (en) | 2017-03-15 | 2021-12-14 | Glycomimetics. Inc. | Galactopyranosyl-cyclohexyl derivauves as E-selectin antagonists |
| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| US11548908B2 (en) | 2017-12-29 | 2023-01-10 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| US11707474B2 (en) | 2018-03-05 | 2023-07-25 | Glycomimetics, Inc. | Methods for treating acute myeloid leukemia and related conditions |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH592697A5 (https=) | 1977-11-15 |
| BR7405955D0 (pt) | 1975-05-13 |
| LU70561A1 (https=) | 1975-05-21 |
| JPS5054697A (https=) | 1975-05-14 |
| AT343909B (de) | 1978-06-26 |
| ATA600074A (de) | 1977-10-15 |
| CA1052042A (fr) | 1979-04-03 |
| NL7409399A (nl) | 1975-01-21 |
| IT1017306B (it) | 1977-07-20 |
| SE7409398L (https=) | 1975-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
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| 8131 | Rejection |