JPS5845144A - 縮合生成物およびその塩の製造方法 - Google Patents

縮合生成物およびその塩の製造方法

Info

Publication number: JPS5845144A
Authority: JP; Japan
Prior art keywords: acid; condensation product; moles; formaldehyde; sulfonic acid
Prior art date: 1981-08-19
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.): Granted

Application number

JP14319182A

Other languages

English (en)

Japanese (ja)

Other versions

JPH041005B2 (fr

Inventor

ジヨン・ジ−・パパロス

ア−パツド・サボリイ

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.)

Diamond Shamrock Corp

Original Assignee

Diamond Shamrock 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.)

1981-08-19

Filing date

1982-08-18

Publication date

1983-03-16

1982-08-18 Application filed by Diamond Shamrock Corp filed Critical Diamond Shamrock Corp

1983-03-16 Publication of JPS5845144A publication Critical patent/JPS5845144A/ja

1992-01-09 Publication of JPH041005B2 publication Critical patent/JPH041005B2/ja

Status Granted legal-status Critical Current

Links

WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 138
239000007859 condensation product Substances 0.000 title claims description 73
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 title claims description 30
229940044654 phenolsulfonic acid Drugs 0.000 title claims description 28
239000002253 acid Substances 0.000 claims description 106
239000004568 cement Substances 0.000 claims description 54
239000002002 slurry Substances 0.000 claims description 42
238000000034 method Methods 0.000 claims description 40
-1 aryl sulfonic acid Chemical compound 0.000 claims description 34
239000000047 product Substances 0.000 claims description 33
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
150000002989 phenols Chemical class 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 13
238000009833 condensation Methods 0.000 claims description 13
230000005494 condensation Effects 0.000 claims description 13
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 10
239000013066 combination product Substances 0.000 claims description 8
229940127555 combination product Drugs 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000011701 zinc Substances 0.000 claims description 8
239000004576 sand Substances 0.000 claims description 7
150000003457 sulfones Chemical class 0.000 claims description 7
JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 claims description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 6
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 6
230000003472 neutralizing effect Effects 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 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 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
150000003460 sulfonic acids Chemical class 0.000 claims description 3
XDESGXRLUIHEJT-UHFFFAOYSA-N 2,3,4-tribenzylphenol Chemical compound C=1C=CC=CC=1CC1=C(CC=2C=CC=CC=2)C(O)=CC=C1CC1=CC=CC=C1 XDESGXRLUIHEJT-UHFFFAOYSA-N 0.000 claims description 2
PGEBXGLGFFYYFX-UHFFFAOYSA-N 2,3-dibenzylphenol Chemical compound C=1C=CC=CC=1CC=1C(O)=CC=CC=1CC1=CC=CC=C1 PGEBXGLGFFYYFX-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
229910052788 barium Inorganic materials 0.000 claims description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
239000002270 dispersing agent Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 14
150000007513 acids Chemical class 0.000 description 13
239000000243 solution Substances 0.000 description 13
238000006277 sulfonation reaction Methods 0.000 description 13
239000008186 active pharmaceutical agent Substances 0.000 description 10
238000006386 neutralization reaction Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000013505 freshwater Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
239000012467 final product Substances 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
229910021511 zinc hydroxide Inorganic materials 0.000 description 3
229940007718 zinc hydroxide Drugs 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000005362 aryl sulfone group Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 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
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229920002401 polyacrylamide Polymers 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000004575 stone Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
239000002344 surface layer Substances 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
238000004448 titration Methods 0.000 description 2
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 1
UUCHLIAGHZJJER-UHFFFAOYSA-N 1,2-diethylnaphthalene Chemical compound C1=CC=CC2=C(CC)C(CC)=CC=C21 UUCHLIAGHZJJER-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
JMEAQNQEOMCBGB-UHFFFAOYSA-N 1-(2-methylpropyl)-4-[4-(2-methylpropyl)phenyl]benzene Chemical group C1=CC(CC(C)C)=CC=C1C1=CC=C(CC(C)C)C=C1 JMEAQNQEOMCBGB-UHFFFAOYSA-N 0.000 description 1
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
URGSMJLDEFDWNX-UHFFFAOYSA-N 1-butylnaphthalene Chemical compound C1=CC=C2C(CCCC)=CC=CC2=C1 URGSMJLDEFDWNX-UHFFFAOYSA-N 0.000 description 1
ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 1
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
AWLDTWVEFFLZOO-UHFFFAOYSA-N 1-phenyloctan-2-ol Chemical compound CCCCCCC(O)CC1=CC=CC=C1 AWLDTWVEFFLZOO-UHFFFAOYSA-N 0.000 description 1
BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
HMAMGXMFMCAOPV-UHFFFAOYSA-N 1-propylnaphthalene Chemical compound C1=CC=C2C(CCC)=CC=CC2=C1 HMAMGXMFMCAOPV-UHFFFAOYSA-N 0.000 description 1
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 1
ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 1
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
DYXBPOGHFMDEDL-UHFFFAOYSA-N 2-naphthalen-2-ylphenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 DYXBPOGHFMDEDL-UHFFFAOYSA-N 0.000 description 1
GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
244000024671 Brassica kaber Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000951471 Citrus junos Species 0.000 description 1
241000218691 Cupressaceae Species 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
241000102542 Kara Species 0.000 description 1
229910019440 Mg(OH) Inorganic materials 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
241000861914 Plecoglossus altivelis Species 0.000 description 1
241000212342 Sium Species 0.000 description 1
102100023185 Transcriptional repressor scratch 1 Human genes 0.000 description 1
101710171414 Transcriptional repressor scratch 1 Proteins 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
BWZOPYPOZJBVLQ-UHFFFAOYSA-K aluminium glycinate Chemical compound O[Al+]O.NCC([O-])=O BWZOPYPOZJBVLQ-UHFFFAOYSA-K 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
MVJQKEVFNNPCRB-UHFFFAOYSA-N azanium acetate tetrahydrate Chemical compound O.O.O.O.C(C)(=O)[O-].[NH4+] MVJQKEVFNNPCRB-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
230000007123 defense Effects 0.000 description 1
229910003460 diamond Inorganic materials 0.000 description 1
239000010432 diamond Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
239000011396 hydraulic cement Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
229940102253 isopropanolamine Drugs 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011268 mixed slurry Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000003129 oil well Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000002245 particle 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
239000004014 plasticizer Substances 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

JP14319182A 1981-08-19 1982-08-18 縮合生成物およびその塩の製造方法 Granted JPS5845144A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US29433781A	1981-08-19	1981-08-19
US294337		1981-08-19
US396698		1982-07-09

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3256048A Division JPH059050A (ja)	1981-08-19	1991-06-25	スラリーの製造方法

Publications (2)

Publication Number	Publication Date
JPS5845144A true JPS5845144A (ja)	1983-03-16
JPH041005B2 JPH041005B2 (fr)	1992-01-09

Family

ID=23132977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14319182A Granted JPS5845144A (ja)	1981-08-19	1982-08-18	縮合生成物およびその塩の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5845144A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6246946A (ja) *	1985-08-23	1987-02-28	ヘミ−・リンツ・アクチエンゲゼルシヤフト	水溶性のナフタリンスルホン酸―ホルムアルデヒド縮合生成物の塩を無機結合剤の混和剤として使用する方法
JPS6483579A (en) *	1987-09-25	1989-03-29	Nippon Catalytic Chem Ind	Surface treating agent for mortar-concrete

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5634719A (en) *	1979-08-30	1981-04-07	Bayer Ag	Phenollformaldehyde polycondensate and its manufacture

1982
- 1982-08-18 JP JP14319182A patent/JPS5845144A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5634719A (en) *	1979-08-30	1981-04-07	Bayer Ag	Phenollformaldehyde polycondensate and its manufacture

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6246946A (ja) *	1985-08-23	1987-02-28	ヘミ−・リンツ・アクチエンゲゼルシヤフト	水溶性のナフタリンスルホン酸―ホルムアルデヒド縮合生成物の塩を無機結合剤の混和剤として使用する方法
JPS6483579A (en) *	1987-09-25	1989-03-29	Nippon Catalytic Chem Ind	Surface treating agent for mortar-concrete

Also Published As

Publication number	Publication date
JPH041005B2 (fr)	1992-01-09

Publication	Publication Date	Title
DK169431B1 (da)	1994-10-31	Salte af vandopløselige naphthalen-sulfonsyre-formaldehyd-kondensater til anvendelse som tilsætningsstoffer til uorganiske bindemidler
US2141569A (en)	1938-12-27	Concrete and hydraulic cement
FI78894B (fi)	1989-06-30	Dispergeringsmedel foer salthaltiga system.
FI62675C (fi)	1983-02-10	Preparat bestaoende av lignosulfonater och ett foerfarande foer framstaellning av detsamma
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CA1133179A (fr)	1982-10-05	Additif pour liants inorganiques
JPH0555459B2 (fr)	1993-08-17
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US3954677A (en)	1976-05-04	Sulfonated aromatic-formaldehyde condensation products
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JPS5845144A - 縮合生成物およびその塩の製造方法 - Google Patents

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Applications Claiming Priority (3)

Related Child Applications (1)

Publications (2)

Family

ID=23132977

Family Applications (1)

Country Status (1)

Cited By (2)

Citations (1)

Patent Citations (1)

Cited By (2)

Also Published As

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