CA1170823A - Compositions a base de glycol renfermant du silane modifie au phosphore - Google Patents

Compositions a base de glycol renfermant du silane modifie au phosphore

Info

Publication number: CA1170823A
Authority: CA; Canada
Prior art keywords: glycol; carbons; composition; alkali metal; propyl
Prior art date: 1982-11-25
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

CA000416421A

Other languages

English (en)

Inventor

Robert T. Jernigan

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1982-11-25

Filing date

1982-11-25

Publication date

1984-07-17

1982-11-25 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1982-11-25 Priority to CA000416421A priority Critical patent/CA1170823A/fr

1984-07-17 Application granted granted Critical

1984-07-17 Publication of CA1170823A publication Critical patent/CA1170823A/fr

Status Expired legal-status Critical Current

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 94
239000000203 mixture Substances 0.000 title claims abstract description 51
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 35
150000004756 silanes Chemical class 0.000 title description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000002947 alkylene group Chemical group 0.000 claims abstract description 11
229910052910 alkali metal silicate Inorganic materials 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
-1 alkylene glycol ether Chemical compound 0.000 claims description 37
238000005260 corrosion Methods 0.000 claims description 18
230000007797 corrosion Effects 0.000 claims description 18
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 14
239000003112 inhibitor Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
239000012141 concentrate Substances 0.000 abstract description 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
239000000499 gel Substances 0.000 description 18
239000000243 solution Substances 0.000 description 16
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
239000000654 additive Substances 0.000 description 7
150000004760 silicates Chemical class 0.000 description 6
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
230000002528 anti-freeze Effects 0.000 description 5
230000008569 process Effects 0.000 description 5
LUVQNLSOWISBKA-UHFFFAOYSA-N trimethoxy-[3-[methoxy(methyl)phosphoryl]oxypropyl]silane Chemical compound CO[Si](OC)(OC)CCCOP(C)(=O)OC LUVQNLSOWISBKA-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 4
150000002334 glycols Chemical class 0.000 description 4
YACKEPLHDIMKIO-UHFFFAOYSA-L methylphosphonate(2-) Chemical compound CP([O-])([O-])=O YACKEPLHDIMKIO-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
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
229910019142 PO4 Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910021538 borax Inorganic materials 0.000 description 3
150000001642 boronic acid derivatives Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
229940113120 dipropylene glycol Drugs 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000002823 nitrates Chemical class 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000010344 sodium nitrate Nutrition 0.000 description 3
239000004317 sodium nitrate Substances 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
239000004328 sodium tetraborate Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KEZYHIPQRGTUDU-UHFFFAOYSA-N 2-[dithiocarboxy(methyl)amino]acetic acid Chemical compound SC(=S)N(C)CC(O)=O KEZYHIPQRGTUDU-UHFFFAOYSA-N 0.000 description 2
CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
239000004115 Sodium Silicate Substances 0.000 description 2
230000032683 aging Effects 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003518 caustics Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000002826 coolant Substances 0.000 description 2
GHZKGHQGPXBWSN-UHFFFAOYSA-N methyl(propan-2-yloxy)phosphinic acid Chemical compound CC(C)OP(C)(O)=O GHZKGHQGPXBWSN-UHFFFAOYSA-N 0.000 description 2
150000002826 nitrites Chemical class 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
229910052911 sodium silicate Inorganic materials 0.000 description 2
QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
NNRAOBUKHNZQFX-UHFFFAOYSA-N 2H-benzotriazole-4-thiol Chemical class SC1=CC=CC2=C1NN=N2 NNRAOBUKHNZQFX-UHFFFAOYSA-N 0.000 description 1
COCUVLZAOFRNKA-UHFFFAOYSA-N 3-[3-[dimethoxy(methyl)silyl]propoxy-methylphosphoryl]oxypropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCOP(C)(=O)OCCC[Si](C)(OC)OC COCUVLZAOFRNKA-UHFFFAOYSA-N 0.000 description 1
OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
KNLIOLPZPCWVSQ-UHFFFAOYSA-N CO[Si](CCCC(CCC[Si](OC)(OC)OC)OP(O)=O)(OC)OC Chemical compound CO[Si](CCCC(CCC[Si](OC)(OC)OC)OP(O)=O)(OC)OC KNLIOLPZPCWVSQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FZQSLXQPHPOTHG-UHFFFAOYSA-N [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 Chemical compound [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 FZQSLXQPHPOTHG-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005600 alkyl phosphonate group Chemical group 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
IJHZPJUEZFWKSJ-UHFFFAOYSA-N diethoxy-[3-[methoxy(methyl)phosphoryl]oxypropyl]-methylsilane Chemical compound CCO[Si](C)(OCC)CCCOP(C)(=O)OC IJHZPJUEZFWKSJ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
PAZHGORSDKKUPI-UHFFFAOYSA-N lithium metasilicate Chemical compound [Li+].[Li+].[O-][Si]([O-])=O PAZHGORSDKKUPI-UHFFFAOYSA-N 0.000 description 1
229910052912 lithium silicate Inorganic materials 0.000 description 1
230000005291 magnetic effect Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
229910052913 potassium silicate Inorganic materials 0.000 description 1
235000019353 potassium silicate Nutrition 0.000 description 1
JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
125000005625 siliconate group Chemical group 0.000 description 1
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
BFEPURQOPWHCLT-UHFFFAOYSA-N trimethoxy-[3-[methyl(3-trimethoxysilylpropoxy)phosphoryl]oxypropyl]silane Chemical compound CO[Si](OC)(OC)CCCOP(C)(=O)OCCC[Si](OC)(OC)OC BFEPURQOPWHCLT-UHFFFAOYSA-N 0.000 description 1
HEJRESUTIKCCLE-UHFFFAOYSA-N trimethoxy-[4-[methyl(4-trimethoxysilylbutoxy)phosphoryl]oxybutyl]silane Chemical compound CO[Si](OC)(OC)CCCCOP(C)(=O)OCCCC[Si](OC)(OC)OC HEJRESUTIKCCLE-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

Landscapes

Preventing Corrosion Or Incrustation Of Metals (AREA)

CA000416421A 1982-11-25 1982-11-25 Compositions a base de glycol renfermant du silane modifie au phosphore Expired CA1170823A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000416421A CA1170823A (fr)	1982-11-25	1982-11-25	Compositions a base de glycol renfermant du silane modifie au phosphore

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000416421A CA1170823A (fr)	1982-11-25	1982-11-25	Compositions a base de glycol renfermant du silane modifie au phosphore

Publications (1)

Publication Number	Publication Date
CA1170823A true CA1170823A (fr)	1984-07-17

Family

ID=4124028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000416421A Expired CA1170823A (fr)	1982-11-25	1982-11-25	Compositions a base de glycol renfermant du silane modifie au phosphore

Country Status (1)

Country	Link
CA (1)	CA1170823A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9868902B2 (en)	2014-07-17	2018-01-16	Soulbrain Co., Ltd.	Composition for etching

1982
- 1982-11-25 CA CA000416421A patent/CA1170823A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9868902B2 (en)	2014-07-17	2018-01-16	Soulbrain Co., Ltd.	Composition for etching
US10465112B2 (en)	2014-07-17	2019-11-05	Soulbrain Co., Ltd.	Composition for etching

Legal Events

Date	Code	Title	Description
2001-07-18	MKEC	Expiry (correction)
2002-11-25	MKEX	Expiry

Publication	Publication Date	Title
US4772408A (en)	1988-09-20	Silicate-containing antifreeze with phosphonate silane stabilizer
US4370255A (en)	1983-01-25	Stabilization of aqueous silicates using alkali siliconates of silylalkyl phosphonates
US4333843A (en)	1982-06-08	Glycol compositions containing a hydrolyzate of an organo phosphorus-silicon compound
CA1173228A (fr)	1984-08-28	Stabilisation de silicates au moyen de sels de siliconates a substitution et qui contiennent de l'azote ou du soufre
US5000866A (en)	1991-03-19	Antifreeze compositions containing alkane tetracarboxylic acid for use with hard water
US4287077A (en)	1981-09-01	Glycol compositions containing an ether modified silicone to inhibit gelling
US4367154A (en)	1983-01-04	Glycol compositions containing a phosphorous-modified silane
US4965385A (en)	1990-10-23	Organosilane stabilizers for inorganic silicates in antifreezer/coolant compositions
EP0111013B1 (fr)	1986-07-23	Compositions de glycol contenant un silane modifié par du phosphore
US4775415A (en)	1988-10-04	Alcohol-based aluminum corrosion inhibitor compositions comprising polysilyl compounds
CA1170823A (fr)	1984-07-17	Compositions a base de glycol renfermant du silane modifie au phosphore
US4701277A (en)	1987-10-20	Silicate-containing antifreeze with carboxy-substituted organosilicon stabilizer
CA1143925A (fr)	1983-04-05	Stabilisation de silicates aqueux grace a des siliconates d'alcalis de phosphonates de silylalkyle
US4676919A (en)	1987-06-30	Low pH-buffered silicon/silicate antifreeze concentrates
US4462921A (en)	1984-07-31	Siloxane stabilizers for inorganic silicates in antifreeze/coolant formulations
US4466896A (en)	1984-08-21	Ethylenediamine triacetic acid siloxane stabilizers for inorganic silicates in antifreeze/coolant formulations
JPS6352037B2 (fr)	1988-10-17
US4707286A (en)	1987-11-17	Coolant stabilizer
US2212992A (en)	1940-08-27	Antiknock fuel
US5087717A (en)	1992-02-11	Organosilane stabilizers for inorganic silicates in antifreezer/coolant compositions
US4485025A (en)	1984-11-27	Polyalkylpolyalkoxypolysiloxane stabilizers for inorganic silicates in antifreeze/coolant formulations
EP0029728B1 (fr)	1985-03-13	Compositions de glycol contenant un silicone modifié par un éther
EP0189833A1 (fr)	1986-08-06	Utilisation de l'acide méthylène azélaique comme inhibiteur de corrosion
US4767599A (en)	1988-08-30	Silicate-containing antifreeze with carboxy-substituted organosilicon stabilizer
US4643839A (en)	1987-02-17	Silicone reaction products and glycol compositions containing the products