CA1091995A - Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof - Google Patents

Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof

Info

Publication number: CA1091995A
Authority: CA; Canada
Prior art keywords: carbon atoms; group; amine; vinyl; weight
Prior art date: 1975-10-01
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

CA261,499A

Other languages

English (en)

French (fr)

Inventor

Thomas R. Cassutt

James W. Messerly

Ronald L. Senderling

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.)

Goodrich Corp

Original Assignee

BF Goodrich Corp

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.)

1975-10-01

Filing date

1976-09-16

Publication date

1980-12-23

1976-09-16 Application filed by BF Goodrich Corp filed Critical BF Goodrich Corp

1980-12-23 Application granted granted Critical

1980-12-23 Publication of CA1091995A publication Critical patent/CA1091995A/en

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 76
239000007788 liquid Substances 0.000 title claims abstract description 62
239000003822 epoxy resin Substances 0.000 title claims abstract description 18
229920000647 polyepoxide Polymers 0.000 title claims abstract description 18
239000000203 mixture Substances 0.000 claims abstract description 55
239000011353 cycloaliphatic epoxy resin Substances 0.000 claims abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 108
-1 allyl ethers Chemical class 0.000 claims description 42
238000000034 method Methods 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 26
229920002554 vinyl polymer Polymers 0.000 claims description 26
150000001412 amines Chemical class 0.000 claims description 23
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 20
229930185605 Bisphenol Natural products 0.000 claims description 17
229920005989 resin Polymers 0.000 claims description 17
239000011347 resin Substances 0.000 claims description 17
125000001931 aliphatic group Chemical group 0.000 claims description 15
239000000178 monomer Substances 0.000 claims description 15
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
239000004593 Epoxy Substances 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 12
150000001993 dienes Chemical class 0.000 claims description 12
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 8
150000004982 aromatic amines Chemical class 0.000 claims description 8
150000002170 ethers Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
125000001118 alkylidene group Chemical group 0.000 claims description 7
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 7
125000003700 epoxy group Chemical group 0.000 claims description 7
MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 claims description 6
150000001253 acrylic acids Chemical class 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
150000005673 monoalkenes Chemical class 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000002723 alicyclic group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000009257 reactivity Effects 0.000 claims description 3
125000004386 diacrylate group Chemical group 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims 3
125000004103 aminoalkyl group Chemical group 0.000 claims 2
229960005141 piperazine Drugs 0.000 claims 2
239000004970 Chain extender Substances 0.000 abstract description 11
238000000576 coating method Methods 0.000 abstract description 10
239000004971 Cross linker Substances 0.000 abstract description 9
239000004615 ingredient Substances 0.000 abstract description 9
239000003795 chemical substances by application Substances 0.000 abstract description 8
239000000853 adhesive Substances 0.000 abstract description 7
230000001070 adhesive effect Effects 0.000 abstract description 7
IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 abstract description 6
239000011248 coating agent Substances 0.000 abstract description 6
238000013329 compounding Methods 0.000 abstract description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 16
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 16
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 description 14
239000000463 material Substances 0.000 description 12
239000002253 acid Substances 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
150000003335 secondary amines Chemical group 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
150000003141 primary amines Chemical class 0.000 description 10
238000002156 mixing Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229920000768 polyamine Polymers 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
229920001971 elastomer Polymers 0.000 description 6
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
229940052303 ethers for general anesthesia Drugs 0.000 description 6
239000000945 filler Substances 0.000 description 6
229920006122 polyamide resin Polymers 0.000 description 6
239000005060 rubber Substances 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000758 substrate Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000001491 aromatic compounds Chemical class 0.000 description 3
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 3
235000019241 carbon black Nutrition 0.000 description 3
239000006229 carbon black Substances 0.000 description 3
239000000539 dimer Substances 0.000 description 3
229920001084 poly(chloroprene) Polymers 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
229920001195 polyisoprene Polymers 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
KWVDRAXPOZQNKU-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)butyl]phenol Chemical compound C=1C=CC=C(O)C=1C(CCC)C1=CC=CC=C1O KWVDRAXPOZQNKU-UHFFFAOYSA-N 0.000 description 2
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 2
KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
229920000459 Nitrile rubber Polymers 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
230000003373 anti-fouling effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
230000001680 brushing effect Effects 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000011521 glass Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
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 2
238000010438 heat treatment Methods 0.000 description 2
QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
201000006747 infectious mononucleosis Diseases 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
AFZZYIJIWUTJFO-UHFFFAOYSA-N meta-diethylbenzene Natural products CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
150000004885 piperazines Chemical class 0.000 description 2
229920000120 polyethyl acrylate Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229910052976 metal sulfide Inorganic materials 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000010690 paraffinic oil Substances 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
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095574 propionic acid Drugs 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping 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
238000010526 radical polymerization reaction Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012763 reinforcing filler Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
238000007665 sagging Methods 0.000 description 1
238000005488 sandblasting Methods 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
125000005591 trimellitate group Chemical group 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229960000834 vinyl ether Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L57/06—Homopolymers or copolymers containing elements other than carbon and hydrogen
- C08L57/12—Homopolymers or copolymers containing elements other than carbon and hydrogen containing nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Epoxy Resins (AREA)
Paints Or Removers (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA261,499A 1975-10-01 1976-09-16 Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof Expired CA1091995A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US61863275A	1975-10-01	1975-10-01
US618,632		1975-10-01

Publications (1)

Publication Number	Publication Date
CA1091995A true CA1091995A (en)	1980-12-23

Family

ID=24478481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA261,499A Expired CA1091995A (en)	1975-10-01	1976-09-16	Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof

Country Status (6)

Country	Link
JP (1)	JPS5936929B2 (ja)
AU (1)	AU499219B2 (ja)
CA (1)	CA1091995A (ja)
DE (1)	DE2643504A1 (ja)
GB (1)	GB1545807A (ja)
NL (1)	NL7610824A (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57133117A (en) *	1981-02-10	1982-08-17	Nippon Kokan Kk <Nkk>	Epoxy mastic for molding in form
DE3639570A1 (de) *	1986-11-20	1988-06-01	Basf Lacke & Farben	Durch protonierung mit saeure wasserverduennbare bindemittel

1976
- 1976-09-16 CA CA261,499A patent/CA1091995A/en not_active Expired
- 1976-09-22 AU AU18000/76A patent/AU499219B2/en not_active Expired
- 1976-09-28 DE DE19762643504 patent/DE2643504A1/de not_active Withdrawn
- 1976-09-30 NL NL7610824A patent/NL7610824A/xx not_active Application Discontinuation
- 1976-09-30 JP JP11668876A patent/JPS5936929B2/ja not_active Expired
- 1976-10-01 GB GB4076076A patent/GB1545807A/en not_active Expired

Also Published As

Publication number	Publication date
AU499219B2 (en)	1979-04-12
JPS5936929B2 (ja)	1984-09-06
NL7610824A (nl)	1977-04-05
AU1800076A (en)	1978-04-06
GB1545807A (en)	1979-05-16
JPS5249300A (en)	1977-04-20
DE2643504A1 (de)	1977-04-14

Legal Events

Date	Code	Title	Description
1997-12-23	MKEX	Expiry

Publication	Publication Date	Title
US4260700A (en)	1981-04-07	Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof
US4055541A (en)	1977-10-25	Reaction products of non-cycloaliphatic epoxy resins and amine-terminated liquid polymers and process for preparation thereof
US4129670A (en)	1978-12-12	Reaction products of non-cycloaliphatic epoxy resins and amine-terminated liquid polymers and process for preparation thereof
US4507411A (en)	1985-03-26	Cross-linked polymer compositions and production thereof
US5229438A (en)	1993-07-20	Two-component epoxy resin compositions
US4323603A (en)	1982-04-06	Fluoroelastomer film compositions containing silane compounds and method for the preparation thereof
AU625109B2 (en)	1992-07-02	Adhesion method for silicon containing adhesives by using silicon containing vinyl polymer
US4423183A (en)	1983-12-27	Fluoroelastomer film compositions and solutions containing fatty polyamide curatives
US4421878A (en)	1983-12-20	Fluoroelastomer film compositions and solutions containing epoxy resin adducts
GB1602401A (en)	1981-11-11	Primers for adhering silicone materials to substrates
US6515094B2 (en)	2003-02-04	Silicone amino-epoxy cross-linking system
JP3078003B2 (ja)	2000-08-21	熱硬化性組成物
US4347268A (en)	1982-08-31	Novel fluoroelastomer film compositions containing vinyl copolymers and method for the preparation thereof
KR20070064583A (ko)	2007-06-21	수성 아스팔트 코팅 조성물
US4018847A (en)	1977-04-19	Flexible coating compositions
KR20120014426A (ko)	2012-02-17	1액형 수분산 에폭시 수지의 제조방법
JPH11343454A (ja)	1999-12-14	防食塗料組成物、塗膜、防食方法および船舶バラストタンク
CA1091995A (en)	1980-12-23	Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof
US4400482A (en)	1983-08-23	Novel fluoroelastomer film compositions containing silane compounds and method for the preparation thereof
US4447478A (en)	1984-05-08	Novel fluoroelastomer film compositions and method for the preparation thereof
CA1050186A (en)	1979-03-06	Adhesive polyalkadiene compositions
JP5667854B2 (ja)	2015-02-12	１液組成物
JP2843408B2 (ja)	1999-01-06	熱硬化性組成物およびそれを塗装した塗装物
JP3297854B2 (ja)	2002-07-02	下塗り塗料用組成物、及び該組成物を用いた塗装方法
JP2003221501A (ja)	2003-08-08	硬化性組成物