CA1255040A - Liquid polysulphide/polyepoxide copolymers - Google Patents
Liquid polysulphide/polyepoxide copolymersInfo
- Publication number
- CA1255040A CA1255040A CA000486937A CA486937A CA1255040A CA 1255040 A CA1255040 A CA 1255040A CA 000486937 A CA000486937 A CA 000486937A CA 486937 A CA486937 A CA 486937A CA 1255040 A CA1255040 A CA 1255040A
- Authority
- CA
- Canada
- Prior art keywords
- epoxy
- mercaptan
- polymer
- liquid
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 62
- 229920001021 polysulfide Polymers 0.000 title claims description 48
- 229920000647 polyepoxide Polymers 0.000 title claims description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 97
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 239000004593 Epoxy Substances 0.000 claims abstract description 63
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 238000007259 addition reaction Methods 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 23
- 239000003822 epoxy resin Substances 0.000 claims description 22
- 125000003700 epoxy group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 150000002118 epoxides Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- 229920001400 block copolymer Polymers 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000036647 reaction Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 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 45
- 239000000047 product Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 13
- 125000000466 oxiranyl group Chemical group 0.000 description 13
- 238000003860 storage Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 238000007654 immersion Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 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 8
- 239000000565 sealant Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 229960001124 trientine Drugs 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- -1 coatings Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920003319 Araldite® Polymers 0.000 description 3
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 3
- 239000004567 concrete Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920006334 epoxy coating Polymers 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229940032007 methylethyl ketone Drugs 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000003442 weekly effect Effects 0.000 description 3
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 2
- 241000905957 Channa melasoma Species 0.000 description 2
- 241000984642 Cura Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000282337 Nasua nasua Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 229920001079 Thiokol (polymer) Polymers 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 241000517645 Abra Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001527806 Iti Species 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 241001233279 Scalopus Species 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000010210 aluminium Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- QPNQLKYHJADYKG-UHFFFAOYSA-N carbamothioylsulfanyl n-methylcarbamodithioate Chemical compound CNC(=S)SSC(N)=S QPNQLKYHJADYKG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8419036 | 1984-07-26 | ||
| GB848419036A GB8419036D0 (en) | 1984-07-26 | 1984-07-26 | Liquid copolymers |
| GB8517361 | 1985-07-09 | ||
| GB08517361A GB2162189B (en) | 1984-07-26 | 1985-07-09 | Curable liquid compositions of epoxy-and mercaptan-terminated polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1255040A true CA1255040A (en) | 1989-05-30 |
Family
ID=26288027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000486937A Expired CA1255040A (en) | 1984-07-26 | 1985-07-17 | Liquid polysulphide/polyepoxide copolymers |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS63314233A (forum.php) |
| AU (1) | AU577398B2 (forum.php) |
| CA (1) | CA1255040A (forum.php) |
| DK (1) | DK339785A (forum.php) |
| IN (1) | IN164412B (forum.php) |
| NO (1) | NO164779C (forum.php) |
| NZ (1) | NZ212727A (forum.php) |
| PT (1) | PT80850B (forum.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100685952B1 (ko) | 2002-03-19 | 2007-02-23 | 엘지.필립스 엘시디 주식회사 | 액정표시소자용 기판, 액정표시소자 및 그 제조방법 |
| DE10320543B4 (de) * | 2003-05-07 | 2006-02-02 | Thioplast Chemicals Gmbh & Co.Kg | Verfahren zur Herstellung von Präpolymeren auf der Basis von Polysulfiden und Polyepoxiden |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789958A (en) * | 1951-10-30 | 1957-04-23 | Thiokol Chemical Corp | Resinous reaction products of polyepoxides and polysulfide polymers and methods of making the same |
| GB787022A (en) * | 1952-12-20 | 1957-11-27 | Minnesota Mining & Mfg | Improvements in or relating to self-hardening, liquid resinous compositions and articles having the resinous composition bonded thereto |
| US3914288A (en) * | 1969-01-02 | 1975-10-21 | Ciba Geigy Ag | Reaction products of polyepoxides, mercaptoalkanoic acid esters and amines |
-
1985
- 1985-07-12 NZ NZ212727A patent/NZ212727A/xx unknown
- 1985-07-17 CA CA000486937A patent/CA1255040A/en not_active Expired
- 1985-07-17 IN IN564/DEL/85A patent/IN164412B/en unknown
- 1985-07-19 AU AU45180/85A patent/AU577398B2/en not_active Ceased
- 1985-07-23 PT PT80850A patent/PT80850B/pt not_active IP Right Cessation
- 1985-07-24 NO NO852951A patent/NO164779C/no unknown
- 1985-07-25 DK DK339785A patent/DK339785A/da not_active Application Discontinuation
-
1988
- 1988-06-01 JP JP63135360A patent/JPS63314233A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK339785D0 (da) | 1985-07-25 |
| JPS63314233A (ja) | 1988-12-22 |
| IN164412B (forum.php) | 1989-03-18 |
| NO164779C (no) | 1990-11-14 |
| DK339785A (da) | 1986-01-27 |
| JPH0432087B2 (forum.php) | 1992-05-28 |
| PT80850B (pt) | 1987-09-30 |
| AU4518085A (en) | 1986-01-30 |
| NO164779B (no) | 1990-08-06 |
| PT80850A (en) | 1985-08-01 |
| NZ212727A (en) | 1988-09-29 |
| NO852951L (no) | 1986-01-27 |
| AU577398B2 (en) | 1988-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |