CA2052224C - Accelerateurs du durcissement de resines du type resole phenolique - Google Patents

Accelerateurs du durcissement de resines du type resole phenolique

Info

Publication number: CA2052224C
Authority: CA; Canada
Prior art keywords: group; resin; composition; member selected; weight
Prior art date: 1990-11-21
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 - Fee Related

Application number

CA 2052224

Other languages

English (en)

Other versions

CA2052224A1 (fr

Inventor

Arthur Harry Gerber

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.)

Hexion Inc

Original Assignee

Borden Chemical Inc

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.)

1990-11-21

Filing date

1991-09-25

Publication date

1998-01-20

1990-11-21 Priority claimed from US07/616,879 external-priority patent/US5182346A/en

1991-09-25 Application filed by Borden Chemical Inc filed Critical Borden Chemical Inc

1992-05-22 Publication of CA2052224A1 publication Critical patent/CA2052224A1/fr

1998-01-20 Application granted granted Critical

1998-01-20 Publication of CA2052224C publication Critical patent/CA2052224C/fr

2011-09-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 215
239000011347 resin Substances 0.000 title claims abstract description 215
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 195
229920003987 resole Polymers 0.000 title claims abstract description 89
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 309
239000000203 mixture Substances 0.000 claims abstract description 243
239000000395 magnesium oxide Substances 0.000 claims abstract description 145
239000003795 chemical substances by application Substances 0.000 claims abstract description 116
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 92
239000011777 magnesium Substances 0.000 claims abstract description 92
229910052749 magnesium Inorganic materials 0.000 claims abstract description 92
150000002148 esters Chemical class 0.000 claims abstract description 91
238000000034 method Methods 0.000 claims abstract description 65
150000001875 compounds Chemical class 0.000 claims abstract description 48
-1 phosphite anions Chemical class 0.000 claims abstract description 47
239000000347 magnesium hydroxide Substances 0.000 claims abstract description 33
229910001862 magnesium hydroxide Inorganic materials 0.000 claims abstract description 33
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims abstract description 31
239000000463 material Substances 0.000 claims abstract description 22
150000001412 amines Chemical class 0.000 claims abstract description 19
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims abstract description 19
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 18
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 14
229910002651 NO3 Inorganic materials 0.000 claims abstract description 13
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 13
239000002738 chelating agent Substances 0.000 claims abstract description 9
239000004848 polyfunctional curative Substances 0.000 claims description 80
125000000217 alkyl group Chemical group 0.000 claims description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 46
150000001450 anions Chemical class 0.000 claims description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 43
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 29
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 26
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 23
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 23
239000011575 calcium Chemical group 0.000 claims description 23
229910052791 calcium Inorganic materials 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 20
239000004576 sand Substances 0.000 claims description 20
239000007983 Tris buffer Substances 0.000 claims description 19
239000011230 binding agent Substances 0.000 claims description 19
229910052808 lithium carbonate Inorganic materials 0.000 claims description 19
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 18
239000000292 calcium oxide Substances 0.000 claims description 16
229920001568 phenolic resin Polymers 0.000 claims description 16
239000007787 solid Substances 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
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 claims description 14
239000011734 sodium Substances 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 13
229910052708 sodium Inorganic materials 0.000 claims description 12
LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 10
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 10
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 10
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 10
239000000377 silicon dioxide Substances 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
150000002596 lactones Chemical class 0.000 claims description 9
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 9
239000002245 particle Substances 0.000 claims description 9
229910052700 potassium Inorganic materials 0.000 claims description 9
239000011591 potassium Chemical group 0.000 claims description 9
239000000843 powder Substances 0.000 claims description 9
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
239000007859 condensation product Substances 0.000 claims description 8
239000000945 filler Substances 0.000 claims description 8
239000005011 phenolic resin Substances 0.000 claims description 8
229910000077 silane Inorganic materials 0.000 claims description 8
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 7
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
229910052782 aluminium Inorganic materials 0.000 claims description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
238000002156 mixing Methods 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 6
239000010439 graphite Substances 0.000 claims description 6
229910002804 graphite Inorganic materials 0.000 claims description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
239000010459 dolomite Substances 0.000 claims description 5
229910000514 dolomite Inorganic materials 0.000 claims description 5
239000000835 fiber Substances 0.000 claims description 5
239000011342 resin composition Substances 0.000 claims description 5
239000010703 silicon Substances 0.000 claims description 5
229910052710 silicon Inorganic materials 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
239000000920 calcium hydroxide Substances 0.000 claims description 4
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 4
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
229910010271 silicon carbide Inorganic materials 0.000 claims description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
229910052582 BN Inorganic materials 0.000 claims description 3
PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 3
229910052581 Si3N4 Inorganic materials 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
239000002318 adhesion promoter Substances 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
229910001570 bauxite Inorganic materials 0.000 claims description 3
239000010450 olivine Substances 0.000 claims description 3
229910052609 olivine Inorganic materials 0.000 claims description 3
239000010453 quartz Substances 0.000 claims description 3
HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 3
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 3
229910052845 zircon Inorganic materials 0.000 claims description 3
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
229940043430 calcium compound Drugs 0.000 claims description 2
150000001674 calcium compounds Chemical class 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
229910052744 lithium Inorganic materials 0.000 claims 3
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
230000001133 acceleration Effects 0.000 abstract description 3
150000003512 tertiary amines Chemical class 0.000 abstract 1
235000012245 magnesium oxide Nutrition 0.000 description 132
235000013824 polyphenols Nutrition 0.000 description 76
239000000654 additive Substances 0.000 description 40
230000000694 effects Effects 0.000 description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
230000000996 additive effect Effects 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
235000012255 calcium oxide Nutrition 0.000 description 15
239000002986 polymer concrete Substances 0.000 description 13
239000003513 alkali Substances 0.000 description 12
238000001723 curing Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 11
238000001879 gelation Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
230000007423 decrease Effects 0.000 description 8
239000011521 glass Substances 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 7
239000004567 concrete Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000002609 medium Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
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 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000003607 modifier Substances 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
150000004756 silanes Chemical class 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 5
229940044170 formate Drugs 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
238000005063 solubilization Methods 0.000 description 5
230000007928 solubilization Effects 0.000 description 5
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 4
239000011449 brick Substances 0.000 description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
239000001087 glyceryl triacetate Substances 0.000 description 4
235000013773 glyceryl triacetate Nutrition 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
150000004679 hydroxides Chemical class 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
239000011823 monolithic refractory Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
230000008569 process Effects 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
239000011775 sodium fluoride Substances 0.000 description 4
235000013024 sodium fluoride Nutrition 0.000 description 4
229960002622 triacetin Drugs 0.000 description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
235000005979 Citrus limon Nutrition 0.000 description 3
244000131522 Citrus pyriformis Species 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
229940106691 bisphenol a Drugs 0.000 description 3
229930188620 butyrolactone Natural products 0.000 description 3
239000004568 cement Substances 0.000 description 3
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
XHNFSESZQMTMQJ-UHFFFAOYSA-M sodium;2,3-diacetyloxypropyl acetate;fluoride Chemical compound [F-].[Na+].CC(=O)OCC(OC(C)=O)COC(C)=O XHNFSESZQMTMQJ-UHFFFAOYSA-M 0.000 description 1
LUXPBRXUQDESHT-UHFFFAOYSA-M sodium;ethyl 2-hydroxypropanoate;chloride Chemical compound [Na+].[Cl-].CCOC(=O)C(C)O LUXPBRXUQDESHT-UHFFFAOYSA-M 0.000 description 1
AQMNWCRSESPIJM-UHFFFAOYSA-N sodium;phosphenic acid Chemical compound [Na+].O[P+]([O-])=O AQMNWCRSESPIJM-UHFFFAOYSA-N 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 description 1
ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
CENHPXAQKISCGD-UHFFFAOYSA-N trioxathietane 4,4-dioxide Chemical compound O=S1(=O)OOO1 CENHPXAQKISCGD-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000002699 waste material Substances 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Phenolic Resins Or Amino Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA 2052224 1990-11-21 1991-09-25 Accelerateurs du durcissement de resines du type resole phenolique Expired - Fee Related CA2052224C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US616,879		1990-11-21
US07/616,879 US5182346A (en)	1990-08-02	1990-11-21	Accelerators for curing phenolic resole resins

Publications (2)

Publication Number	Publication Date
CA2052224A1 CA2052224A1 (fr)	1992-05-22
CA2052224C true CA2052224C (fr)	1998-01-20

Family

ID=24471355

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2052224 Expired - Fee Related CA2052224C (fr)	1990-11-21	1991-09-25	Accelerateurs du durcissement de resines du type resole phenolique

Country Status (4)

Country	Link
JP (1)	JPH0762104B2 (fr)
BR (1)	BR9103262A (fr)
CA (1)	CA2052224C (fr)
MY (1)	MY131202A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6232368B1 (en) *	1999-10-12	2001-05-15	Borden Chemical, Inc.	Ester cured binders
JP2014098081A (ja) *	2012-11-14	2014-05-29	Dic Corp	熱硬化型樹脂組成物及び繊維強化複合材料
TWI747741B (zh) *	2021-02-20	2021-11-21	中國鋼鐵股份有限公司	熱固型高爐灌漿材料

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2869194A (en)	1956-09-26	1959-01-20	Dow Chemical Co	Auto-hardening phenol-formaldehyde composition and method of preparing shell molds therefrom

1991
- 1991-07-30 BR BR919103262A patent/BR9103262A/pt not_active Application Discontinuation
- 1991-09-25 CA CA 2052224 patent/CA2052224C/fr not_active Expired - Fee Related
- 1991-11-21 JP JP35425091A patent/JPH0762104B2/ja not_active Expired - Lifetime
- 1991-11-21 MY MYPI9102156 patent/MY131202A/en unknown

Also Published As

Publication number	Publication date
JPH04300948A (ja)	1992-10-23
MY131202A (en)	2007-07-31
BR9103262A (pt)	1992-08-04
CA2052224A1 (fr)	1992-05-22
JPH0762104B2 (ja)	1995-07-05

Legal Events

Date	Code	Title	Description
1993-07-06	EEER	Examination request
1999-09-27	MKLA	Lapsed

Publication	Publication Date	Title
US5096983A (en)	1992-03-17	Method for making a phenolic resole resin composition having extended work life
US5182346A (en)	1993-01-26	Accelerators for curing phenolic resole resins
US5294649A (en)	1994-03-15	Accelerators for curing phenolic resole resins
CA1337882C (fr)	1996-01-02	Composition a base de resole, renfermant du lithium, utilisee pour l'obtention d'articles refractaires de forme determinee, et d'autres articles durcis
US5214111A (en)	1993-05-25	Retarders for curing phenolic resole resins
US5262495A (en)	1993-11-16	Retarders for curing phenolic resole resins containing an aggregate material
US5223554A (en)	1993-06-29	Accelerators for curing phenolic resole resins
EP0469785B1 (fr)	1995-01-11	Agent retardateur pour le durcissement des résines résols
CA2052224C (fr)	1998-01-20	Accelerateurs du durcissement de resines du type resole phenolique
US5179177A (en)	1993-01-12	Method for retarding ambient temperature hardening of a phenolic resin composition
US5334675A (en)	1994-08-02	Latent acid curable compositions
US5214079A (en)	1993-05-25	Accelerators for curing phenolic resole resins
CA2087659A1 (fr)	1994-05-05	Compositions de liant durcissant a la temperature ambiante
US5208274A (en)	1993-05-04	Retarders for hardening phenolic resins
US20030153648A1 (en)	2003-08-14	High surface area magnesia curing agent
AU636077B2 (en)	1993-04-08	Extended mix life magnesia refractory aggregates for brick and gunning mixes
EP0469786B1 (fr)	1995-01-25	Magnésie ayant une grande surface spécifique pour le durcissement des résines phénoliques
CA2046060C (fr)	1997-09-23	Retardateurs de polymerisation de resines phenoliques
US5145887A (en)	1992-09-08	High surface area magnesia as hardener for phenolic resins
US4036806A (en)	1977-07-19	Molding compounds