CA1262003A - Compositions aux polymeres sans solvant - Google Patents

Compositions aux polymeres sans solvant

Info

Publication number: CA1262003A
Authority: CA; Canada
Prior art keywords: moles; amine; component; diamine; solventless
Prior art date: 1984-03-26
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.): Expired

Application number

CA000488827A

Other languages

English (en)

Inventor

Gus Nichols

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1984-03-26

Filing date

1985-08-15

Publication date

1989-09-26

1984-03-26 Priority claimed from US06/593,591 external-priority patent/US4547562A/en

1985-08-15 Application filed by Individual filed Critical Individual

1989-09-26 Application granted granted Critical

1989-09-26 Publication of CA1262003A publication Critical patent/CA1262003A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 88
150000002118 epoxides Chemical class 0.000 claims abstract description 71
150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 34
229920000768 polyamine Polymers 0.000 claims abstract description 30
229920000058 polyacrylate Polymers 0.000 claims abstract description 22
238000007259 addition reaction Methods 0.000 claims abstract description 19
239000007795 chemical reaction product Substances 0.000 claims abstract description 12
229920000647 polyepoxide Polymers 0.000 claims abstract description 11
201000006747 infectious mononucleosis Diseases 0.000 claims description 91
-1 aluminum trihydrate Chemical class 0.000 claims description 86
239000007788 liquid Substances 0.000 claims description 64
238000002156 mixing Methods 0.000 claims description 61
150000001412 amines Chemical class 0.000 claims description 60
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 46
150000004985 diamines Chemical class 0.000 claims description 39
239000011521 glass Substances 0.000 claims description 36
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 33
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
229920001187 thermosetting polymer Polymers 0.000 claims description 27
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 21
239000004202 carbamide Substances 0.000 claims description 21
229940096522 trimethylolpropane triacrylate Drugs 0.000 claims description 21
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 20
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 19
239000003973 paint Substances 0.000 claims description 19
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
125000004386 diacrylate group Chemical group 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 14
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
150000008064 anhydrides Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
235000014113 dietary fatty acids Nutrition 0.000 claims description 12
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
239000000194 fatty acid Substances 0.000 claims description 12
229930195729 fatty acid Natural products 0.000 claims description 12
239000000539 dimer Substances 0.000 claims description 11
150000004665 fatty acids Chemical class 0.000 claims description 11
238000010438 heat treatment Methods 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 claims description 10
239000000049 pigment Substances 0.000 claims description 10
239000000377 silicon dioxide Substances 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
229940106691 bisphenol a Drugs 0.000 claims description 9
239000002131 composite material Substances 0.000 claims description 9
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
229910000071 diazene Inorganic materials 0.000 claims description 8
239000000975 dye Substances 0.000 claims description 8
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 7
239000000835 fiber Substances 0.000 claims description 7
150000002466 imines Chemical class 0.000 claims description 7
235000012239 silicon dioxide Nutrition 0.000 claims description 7
239000002023 wood Substances 0.000 claims description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
239000001361 adipic acid Substances 0.000 claims description 6
235000011037 adipic acid Nutrition 0.000 claims description 6
229910052782 aluminium Inorganic materials 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
239000000945 filler Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000003949 imides Chemical group 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
150000003141 primary amines Chemical class 0.000 claims description 6
238000005507 spraying Methods 0.000 claims description 6
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 5
239000004698 Polyethylene Substances 0.000 claims description 5
150000001408 amides Chemical group 0.000 claims description 5
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
235000013312 flour Nutrition 0.000 claims description 5
ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 5
229920003986 novolac Polymers 0.000 claims description 5
229920000573 polyethylene Polymers 0.000 claims description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
NTUYQCWDUQBNTK-UHFFFAOYSA-N 2-N,2-N,1,2,5,6-hexamethoxy-6-(methylideneamino)-1,3,5-triazine-2,4-diamine Chemical compound CON(C1(N(C(N(C(=N1)N)OC)(N=C)OC)OC)OC)OC NTUYQCWDUQBNTK-UHFFFAOYSA-N 0.000 claims description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
238000006482 condensation reaction Methods 0.000 claims description 4
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
229940043237 diethanolamine Drugs 0.000 claims description 4
230000009977 dual effect Effects 0.000 claims description 4
239000010439 graphite Substances 0.000 claims description 4
229910002804 graphite Inorganic materials 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
235000006408 oxalic acid Nutrition 0.000 claims description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
239000004814 polyurethane Substances 0.000 claims description 4
239000004576 sand Substances 0.000 claims description 4
150000003457 sulfones Chemical class 0.000 claims description 4
150000003573 thiols Chemical group 0.000 claims description 4
229960001124 trientine Drugs 0.000 claims description 4
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 claims description 3
VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 3
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
235000021355 Stearic acid Nutrition 0.000 claims description 3
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
239000000428 dust Substances 0.000 claims description 3
239000003365 glass fiber Substances 0.000 claims description 3
150000002825 nitriles Chemical group 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
150000003504 terephthalic acids Chemical class 0.000 claims description 3
239000010936 titanium Substances 0.000 claims description 3
229910052719 titanium Inorganic materials 0.000 claims description 3
LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 claims description 2
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 2
239000004606 Fillers/Extenders Substances 0.000 claims description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
239000005643 Pelargonic acid Substances 0.000 claims description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 claims description 2
229940031098 ethanolamine Drugs 0.000 claims description 2
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 2
150000002531 isophthalic acids Chemical class 0.000 claims description 2
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 claims description 2
QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 claims description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 claims description 2
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
229940113165 trimethylolpropane Drugs 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims 29
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims 2
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical class CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 claims 2
DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 claims 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 2
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
PBWHJRFXUPLZDS-UHFFFAOYSA-N (1-Ethylpropyl)benzene Chemical compound CCC(CC)C1=CC=CC=C1 PBWHJRFXUPLZDS-UHFFFAOYSA-N 0.000 claims 1
NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-UHFFFAOYSA-N 0.000 claims 1
QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
VEGUCZXWLYWJFN-UHFFFAOYSA-N 3-[(3-hydroxy-2-methylphenyl)methyl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1CC1=CC=CC(O)=C1C VEGUCZXWLYWJFN-UHFFFAOYSA-N 0.000 claims 1
WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 claims 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
XTDZADAXBMSVLD-UHFFFAOYSA-N 6-prop-2-enoyloxyhex-5-enyl prop-2-enoate Chemical compound C=CC(=O)OCCCCC=COC(=O)C=C XTDZADAXBMSVLD-UHFFFAOYSA-N 0.000 claims 1
229920005830 Polyurethane Foam Polymers 0.000 claims 1
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 claims 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 1
229930003836 cresol Natural products 0.000 claims 1
ACYMGUSQXQEHGA-UHFFFAOYSA-N cyclohex-2-en-1-amine Chemical compound NC1CCCC=C1 ACYMGUSQXQEHGA-UHFFFAOYSA-N 0.000 claims 1
150000001991 dicarboxylic acids Chemical class 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
229960004275 glycolic acid Drugs 0.000 claims 1
238000003475 lamination Methods 0.000 claims 1
229910044991 metal oxide Inorganic materials 0.000 claims 1
101150009274 nhr-1 gene Proteins 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
229920006327 polystyrene foam Polymers 0.000 claims 1
229940058401 polytetrafluoroethylene Drugs 0.000 claims 1
239000004810 polytetrafluoroethylene Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
239000001294 propane Substances 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
229920002379 silicone rubber Polymers 0.000 claims 1
239000004945 silicone rubber Substances 0.000 claims 1
DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 claims 1
150000003628 tricarboxylic acids Chemical class 0.000 claims 1
239000012463 white pigment Substances 0.000 claims 1
238000000576 coating method Methods 0.000 abstract description 17
238000000465 moulding Methods 0.000 abstract description 3
239000000306 component Substances 0.000 description 162
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 40
229940048053 acrylate Drugs 0.000 description 33
239000002904 solvent Substances 0.000 description 24
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 20
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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239000010941 cobalt Substances 0.000 description 1
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238000005336 cracking Methods 0.000 description 1
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230000036541 health Effects 0.000 description 1
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239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007689 inspection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
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YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
239000004761 kevlar Substances 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
230000007775 late Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
HZHRYYYIOGLPCB-UHFFFAOYSA-N n,n-bis(hydroxymethyl)prop-2-enamide Chemical compound OCN(CO)C(=O)C=C HZHRYYYIOGLPCB-UHFFFAOYSA-N 0.000 description 1
OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
AUCNMQYOQYTGPE-UHFFFAOYSA-N n-(hydroxymethyl)-n-methylprop-2-enamide Chemical compound OCN(C)C(=O)C=C AUCNMQYOQYTGPE-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
150000004780 naphthols Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical group CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
238000010422 painting Methods 0.000 description 1
239000000123 paper Substances 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
150000003097 polyterpenes Chemical class 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
OGOBWYZAVILZEC-UHFFFAOYSA-N propyl 2-hydroxyprop-2-enoate Chemical compound CCCOC(=O)C(O)=C OGOBWYZAVILZEC-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping Methods 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000013535 sea water Substances 0.000 description 1
239000000565 sealant Substances 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 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
229940014800 succinic anhydride Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000011269 tar Substances 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
239000013638 trimer Substances 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
235000013799 ultramarine blue Nutrition 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Polyethers (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Epoxy Resins (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Paints Or Removers (AREA)

CA000488827A 1984-03-26 1985-08-15 Compositions aux polymeres sans solvant Expired CA1262003A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/593,591 US4547562A (en)	1984-03-26	1984-03-26	Solventless polymeric composition comprising non arylamine, polyacrylate and epoxide
US593,591		1984-03-26

Publications (1)

Publication Number	Publication Date
CA1262003A true CA1262003A (fr)	1989-09-26

Family

ID=24375338

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000488827A Expired CA1262003A (fr)	1984-03-26	1985-08-15	Compositions aux polymeres sans solvant

Country Status (2)

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JP (1)	JPS6262810A (fr)
CA (1)	CA1262003A (fr)

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JP3598649B2 (ja) *	1996-05-07	2004-12-08	東洋インキ製造株式会社	硬化性樹脂組成物
JP3918269B2 (ja) *	1997-12-25	2007-05-23	凸版印刷株式会社	耐熱性低誘電率樹脂組成物とその製造方法、及びその耐熱性低誘電率樹脂組成物を用いた電子機器部品
KR101579276B1 (ko) *	2008-03-24	2015-12-21	아이카고교 가부시키가이샤	수지조성물, 하드코팅제, 필름 및 성형체의 제조방법
JP7456718B2 (ja) *	2015-10-28	2024-03-27	株式会社大林組	硬化性樹脂組成物の製造方法、硬化性樹脂組成物、硬化性樹脂建設資材の製造方法、及び、硬化性樹脂建設資材

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US3844916A (en) *	1972-09-18	1974-10-29	Desoto Inc	Radiation curable non-gelled michael addition reaction products
JPS51101100A (ja) *	1975-03-05	1976-09-07	Toa Gosei Chem Ind	Kokaseijushisoseibutsu
DE3479810D1 (en) *	1983-08-24	1989-10-26	Ciba Geigy Ag	Method of producing prepregs and composite materials reinforced therewith

1985
- 1985-08-15 CA CA000488827A patent/CA1262003A/fr not_active Expired
- 1985-09-10 JP JP19869685A patent/JPS6262810A/ja active Pending

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Publication number	Publication date
JPS6262810A (ja)	1987-03-19

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Date	Code	Title	Description
2006-09-26	MKEX	Expiry

Publication	Publication Date	Title
US4547562A (en)	1985-10-15	Solventless polymeric composition comprising non arylamine, polyacrylate and epoxide
US4675374A (en)	1987-06-23	Solventless polymeric composition reaction product of (1) adduct of amine and acrylate with (2) polyacrylate
RU2748977C2 (ru)	2021-06-02	Композиция эпоксидной смолы с низким уровнем выбросов
JP6795604B2 (ja)	2020-12-02	低排出エポキシ樹脂組成物用の硬化剤
US5319004A (en)	1994-06-07	Hardener for epoxy resins comprising reaction products of polyamidoamines, secondary polyamines and epoxy-polyol adducts
JP7638860B2 (ja)	2025-03-04	エポキシ樹脂用硬化剤
CN105939992B (zh)	2019-04-09	用于低排放环氧树脂产物的胺
CN112673042B (zh)	2024-03-22	用于固化包含烷基化胺的环氧树脂的促进剂
JP2022501462A (ja)	2022-01-06	エポキシ樹脂用硬化剤
CN110382587A (zh)	2019-10-25	用于制备低排放环氧树脂组合物的固化剂的方法
CA1064892A (fr)	1979-10-23	Produit de cure pour resines epoxydiques
CA3136397A1 (fr)	2020-12-17	Plancher d'epoxy auto-nivelant a base d'eau, non combustible
CN115427476B (zh)	2025-06-27	胺-环氧树脂加合物
JP7274422B2 (ja)	2023-05-16	低排出エポキシ樹脂組成物用の硬化剤
CA1262003A (fr)	1989-09-26	Compositions aux polymeres sans solvant
JP7809061B2 (ja)	2026-01-30	エポキシ樹脂コーティング用の硬化剤
EP4370578A1 (fr)	2024-05-22	Accélérateur pour résines époxy
CN115003725B (zh)	2025-06-27	胺-环氧树脂加合物
US4816576A (en)	1989-03-28	Sulphonic acid amidamines
JP2024503197A (ja)	2024-01-25	アルキル化ジアミンとノボラックエポキシ樹脂とのアダクト
Patel et al.	1998	Epoxy resins-polyamide coating system
Baraiya et al.	1998	Coating Properties of Di-and Tri-functional epoxy resin using novel epoxy based polyamide as curing agent
JPH10139861A (ja)	1998-05-26	水性エポキシド樹脂組成物
JPS63178124A (ja)	1988-07-22	アミン系硬化剤組成物