CA1111192A - Additifs d'epoxy - Google Patents

Additifs d'epoxy

Info

Publication number: CA1111192A
Authority: CA; Canada
Prior art keywords: radical; carbon atoms; hydrogen; composition; methyl
Prior art date: 1976-11-22
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

CA290,993A

Other languages

English (en)

Inventor

Heinz Schulze

Harold G. Waddill

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.)

Texaco Development Corp

Original Assignee

Texaco Development 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.)

1976-11-22

Filing date

1977-11-16

Publication date

1981-10-20

1976-11-22 Priority claimed from US05/743,878 external-priority patent/US4115361A/en

1976-11-22 Priority claimed from US05/743,817 external-priority patent/US4110310A/en

1976-11-22 Priority claimed from US05/743,814 external-priority patent/US4110309A/en

1976-11-22 Priority claimed from US05/743,815 external-priority patent/US4115360A/en

1977-11-16 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1981-10-20 Application granted granted Critical

1981-10-20 Publication of CA1111192A publication Critical patent/CA1111192A/fr

Status Expired legal-status Critical Current

Links

239000000654 additive Substances 0.000 title claims abstract description 86
239000004593 Epoxy Substances 0.000 title claims description 47
239000000203 mixture Substances 0.000 claims abstract description 107
239000003795 chemical substances by application Substances 0.000 claims abstract description 79
229920000647 polyepoxide Polymers 0.000 claims abstract description 57
239000003822 epoxy resin Substances 0.000 claims abstract description 38
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims abstract description 37
229960002317 succinimide Drugs 0.000 claims abstract description 15
125000003277 amino group Chemical group 0.000 claims abstract description 12
230000000996 additive effect Effects 0.000 claims description 60
-1 amine salt Chemical class 0.000 claims description 46
125000004432 carbon atom Chemical group C* 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
229920000768 polyamine Polymers 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000002877 alkyl aryl group Chemical group 0.000 claims description 13
150000002118 epoxides Chemical class 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 4
125000002993 cycloalkylene group Chemical group 0.000 claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims description 4
239000000194 fatty acid Substances 0.000 claims description 4
229930195729 fatty acid Natural products 0.000 claims description 4
150000004665 fatty acids Chemical class 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 abstract description 55
229920000570 polyether Polymers 0.000 abstract description 47
239000004721 Polyphenylene oxide Substances 0.000 abstract description 45
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract description 18
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 abstract description 12
125000003368 amide group Chemical group 0.000 abstract description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 description 52
229920005989 resin Polymers 0.000 description 47
239000011347 resin Substances 0.000 description 47
238000009472 formulation Methods 0.000 description 43
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 25
238000009740 moulding (composite fabrication) Methods 0.000 description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
150000004985 diamines Chemical class 0.000 description 22
230000001070 adhesive effect Effects 0.000 description 21
235000013877 carbamide Nutrition 0.000 description 21
239000000463 material Substances 0.000 description 20
WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 19
239000004202 carbamide Substances 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000000853 adhesive Substances 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000005266 casting Methods 0.000 description 9
239000000376 reactant Substances 0.000 description 9
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
229960005419 nitrogen Drugs 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
150000002513 isocyanates Chemical class 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
229920001451 polypropylene glycol Polymers 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229960001124 trientine Drugs 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
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 5
239000003054 catalyst Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
238000012360 testing method Methods 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000004411 aluminium Substances 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000758 substrate Substances 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
239000009261 D 400 Substances 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000007824 aliphatic compounds Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000000576 coating method Methods 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000000470 constituent Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000006268 reductive amination reaction Methods 0.000 description 3
239000007921 spray Substances 0.000 description 3
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 description 2
GPSDMAXHNMFLRZ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;propan-1-amine Chemical compound CCCN.CCCN.OCCOCCO GPSDMAXHNMFLRZ-UHFFFAOYSA-N 0.000 description 2
KUPATLIWLHOFKT-UHFFFAOYSA-N 2-[2-[2-(2-aminoethoxy)propoxy]propoxy]ethanamine Chemical compound NCCOC(C)COC(C)COCCN KUPATLIWLHOFKT-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
150000007945 N-acyl ureas Chemical class 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000007872 degassing Methods 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012530 fluid Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229920003986 novolac Polymers 0.000 description 2
125000005702 oxyalkylene group Chemical group 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
230000036647 reaction Effects 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
230000035939 shock Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 1
AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
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 1
CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
OORDEDRRTSWSRC-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] acetate Chemical compound CC(=O)OCC(CO)(CO)CO OORDEDRRTSWSRC-UHFFFAOYSA-N 0.000 description 1
BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
229940053198 antiepileptics succinimide derivative Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000003796 beauty Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
239000000539 dimer Substances 0.000 description 1
WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
238000004382 potting Methods 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
239000000565 sealant Substances 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000013638 trimer Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Adhesives Or Adhesive Processes (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA290,993A 1976-11-22 1977-11-16 Additifs d'epoxy Expired CA1111192A (fr)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US743,878		1976-11-22
US05/743,878 US4115361A (en)	1976-11-22	1976-11-22	Polyether urea epoxy additives
US743,817		1976-11-22
US05/743,817 US4110310A (en)	1976-11-22	1976-11-22	Polyether diamide epoxy additives
US743,814		1976-11-22
US05/743,814 US4110309A (en)	1976-11-22	1976-11-22	Polyether diureide epoxy additives
US05/743,815 US4115360A (en)	1976-11-22	1976-11-22	Polyether urea epoxy additives
US743,815		1976-11-22

Publications (1)

Publication Number	Publication Date
CA1111192A true CA1111192A (fr)	1981-10-20

Family

ID=27505627

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,993A Expired CA1111192A (fr)	1976-11-22	1977-11-16	Additifs d'epoxy

Country Status (8)

Country	Link
JP (1)	JPS5365399A (fr)
AR (1)	AR224228A1 (fr)
AU (1)	AU505211B2 (fr)
BR (1)	BR7707718A (fr)
CA (1)	CA1111192A (fr)
FR (1)	FR2371483A1 (fr)
GB (1)	GB1556797A (fr)
MX (1)	MX6229E (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1577093A (en) *	1977-06-30	1980-10-15	Texaco Development Corp	Bis ureide of a polyoxyalkylene polyamine as an epoxy additive
BR8807710A (pt) *	1987-09-21	1990-08-07	Dow Chemical Co	Polieteres amino-funcionais contendo moleculas de ureia, biureto, tioureia, ditiobiureto, tioamida e/ou amida em sua cadeia principal,e pre-polimeros de uretana/ureia e polimeros produzidos a partir desses pre-polimeros
US4837295A (en) *	1988-03-04	1989-06-06	Loctite Corporation	Epoxy-amine compositions employing unsaturated imides
EP1546227B1 (fr) *	2002-08-30	2009-12-23	Huntsman Petrochemical Corporation	Agents a base de polyamine de polyether et melanges associes
US7666954B2 (en)	2006-10-20	2010-02-23	Air Products And Chemicals, Inc.	Epoxy resin amine curing agent of N,N′-dimethyl secondary diamine polymer
JP2009256583A (ja) *	2007-09-28	2009-11-05	Sumitomo Bakelite Co Ltd	液状エポキシ樹脂組成物およびそれを用いた半導体装置
WO2009085662A2 (fr)	2007-12-27	2009-07-09	3M Innovative Properties Company	Adhésifs autocollants à base d'urée
US9296933B2 (en)	2009-05-15	2016-03-29	3M Innovative Properties Company	Urethane-based pressure sensitive adhesives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1694139A1 (de) *	1967-03-16	1971-07-22	Hoechst Ag	Verwendung von gehaerteten Epoxidharzen als schwingungsdaempfendes Material
US4002598A (en) *	1975-03-06	1977-01-11	Texaco Development Corporation	Polyether urea epoxy curing agent

1977
- 1977-10-20 GB GB4362977A patent/GB1556797A/en not_active Expired
- 1977-10-28 AU AU30151/77A patent/AU505211B2/en not_active Expired
- 1977-10-31 AR AR26980577A patent/AR224228A1/es active
- 1977-11-16 CA CA290,993A patent/CA1111192A/fr not_active Expired
- 1977-11-21 BR BR7707718A patent/BR7707718A/pt unknown
- 1977-11-21 FR FR7734859A patent/FR2371483A1/fr active Granted
- 1977-11-21 MX MX657277U patent/MX6229E/es unknown
- 1977-11-22 JP JP13955177A patent/JPS5365399A/ja active Granted

Also Published As

Publication number	Publication date
AU505211B2 (en)	1979-11-15
BR7707718A (pt)	1978-07-18
FR2371483A1 (fr)	1978-06-16
AR224228A1 (es)	1981-11-13
JPS5365399A (en)	1978-06-10
MX6229E (es)	1984-12-28
AU3015177A (en)	1979-06-21
FR2371483B1 (fr)	1984-05-25
JPS5529086B2 (fr)	1980-08-01
GB1556797A (en)	1979-11-28

Legal Events

Date	Code	Title	Description
1998-10-20	MKEX	Expiry

Publication	Publication Date	Title
US4122069A (en)	1978-10-24	Polyether dihydroxyalkyl carbamate epoxy additive for epoxy resins
US4115361A (en)	1978-09-19	Polyether urea epoxy additives
US4115360A (en)	1978-09-19	Polyether urea epoxy additives
US4178426A (en)	1979-12-11	Epoxy resin compositions
US4581422A (en)	1986-04-08	Epoxy resin composition containing a curing agent which is a reaction product of cyanoguanidine, formaldehyde and an amine
US4146700A (en)	1979-03-27	Diamides of polyoxyalkylenepolyamine-urea condensates as epoxy resin additives
US5422042A (en)	1995-06-06	Imidazolidone polyetheramine strength enhancing additives of epoxy resin systems
US4162358A (en)	1979-07-24	Polyaromatic amine curing agents for epoxy resins
US5025100A (en)	1991-06-18	Liquid amine terminated derivatives of diglycidyl ethers
US4147857A (en)	1979-04-03	Epoxy cure with polyamine-polyether succinimide systems
JPH0418419A (ja)	1992-01-22	アミノ基を末端基とするポリアミド
GB2031431A (en)	1980-04-23	Novel epoxy curing agent
US4011281A (en)	1977-03-08	Polyether thiourea epoxy curing agents
US4110309A (en)	1978-08-29	Polyether diureide epoxy additives
US4403078A (en)	1983-09-06	Epoxy resin composition
US4139524A (en)	1979-02-13	Bis ureide of a polyoxyalkylene polyamine as an epoxy additive
US4187367A (en)	1980-02-05	Epoxy resins with improved adhesion and peel strength
US4116938A (en)	1978-09-26	Polyether diureide epoxy additives
CA1325308C (fr)	1993-12-14	Compose codurcisseurs de type oxamidoamine dans des adhesifs epoxydiques thermodurcissables
US4581423A (en)	1986-04-08	Epoxy resin composition containing a curing agent which is a reaction product of hydantoins, formaldehyde and an amine
US4533719A (en)	1985-08-06	Epoxy resins with increased flexibility
US4110310A (en)	1978-08-29	Polyether diamide epoxy additives
US5091574A (en)	1992-02-25	Polyoxyethylene diamine derivatives of diglycidyl ethers
CA1325860C (fr)	1994-01-04	Agents codurcissants de type amidoamine dans des adhesifs thermodurcissables
CA1111067A (fr)	1981-10-20	Bis-ureides de polyamines de polyoxyalkylenes servant comme additifs pour resines epoxydes