CA2309887C - Inhibiteurs de corrosion a base de neo-acid - Google Patents

Inhibiteurs de corrosion a base de neo-acid Download PDF

Info

Publication number: CA2309887C
Authority: CA; Canada
Prior art keywords: neo; mono; corrosion inhibitor; acid; antifreeze coolant
Prior art date: 1995-12-05
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 - Lifetime

Application number

CA002309887A

Other languages

English (en)

Other versions

CA2309887A1 (fr

Inventor

Aleksei V. Gershun

William C. Mercer

Peter M. Woyciesjes

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.)

Prestone Products Corp USA

Original Assignee

Prestone Products Corp USA

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.)

1995-12-05

Filing date

1996-11-22

Publication date

2002-02-12

1995-12-05 Priority claimed from US08/567,639 external-priority patent/US5741436A/en

1996-11-22 Application filed by Prestone Products Corp USA filed Critical Prestone Products Corp USA

1996-11-22 Priority claimed from CA 2238174 external-priority patent/CA2238174C/fr

1997-06-12 Publication of CA2309887A1 publication Critical patent/CA2309887A1/fr

2002-02-12 Application granted granted Critical

2002-02-12 Publication of CA2309887C publication Critical patent/CA2309887C/fr

2016-11-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000007797 corrosion Effects 0.000 title claims abstract description 106
238000005260 corrosion Methods 0.000 title claims abstract description 106
239000003112 inhibitor Substances 0.000 title claims abstract description 87
239000000203 mixture Substances 0.000 claims abstract description 72
230000002528 anti-freeze Effects 0.000 claims abstract description 54
239000002826 coolant Substances 0.000 claims abstract description 48
YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims abstract description 42
150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 30
238000009472 formulation Methods 0.000 claims description 45
239000012141 concentrate Substances 0.000 claims description 40
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
-1 or isomer Chemical class 0.000 claims description 14
VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
238000007710 freezing Methods 0.000 claims description 9
230000008014 freezing Effects 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
230000000994 depressogenic effect Effects 0.000 claims description 8
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 7
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
150000003852 triazoles Chemical class 0.000 claims description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
150000001642 boronic acid derivatives Chemical class 0.000 claims description 5
150000002826 nitrites Chemical class 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 4
CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 claims description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
150000002823 nitrates Chemical class 0.000 claims description 4
235000021317 phosphate Nutrition 0.000 claims description 4
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
150000004760 silicates Chemical class 0.000 claims description 4
150000003557 thiazoles Chemical class 0.000 claims 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 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
239000012964 benzotriazole Substances 0.000 claims description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
159000000001 potassium salts Chemical class 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
229910052751 metal Inorganic materials 0.000 abstract description 19
239000002184 metal Substances 0.000 abstract description 19
150000007524 organic acids Chemical class 0.000 abstract description 13
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002253 acid Substances 0.000 description 17
229910052782 aluminium Inorganic materials 0.000 description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
238000000034 method Methods 0.000 description 8
HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 6
238000002485 combustion reaction Methods 0.000 description 6
TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
230000002195 synergetic effect Effects 0.000 description 5
UZHQHNDRVITJPL-UHFFFAOYSA-N 5,6-dimethoxy-1h-indole-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1NC(C(O)=O)=C2 UZHQHNDRVITJPL-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
229910045601 alloy Inorganic materials 0.000 description 3
239000000956 alloy Substances 0.000 description 3
239000002518 antifoaming agent Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000012530 fluid Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910000838 Al alloy Inorganic materials 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000013529 heat transfer fluid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000006174 pH buffer Substances 0.000 description 2
230000010287 polarization Effects 0.000 description 2
239000002455 scale inhibitor Substances 0.000 description 2
230000009919 sequestration Effects 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
CQPFMGBJSMSXLP-ZAGWXBKKSA-M Acid orange 7 Chemical compound OC1=C(C2=CC=CC=C2C=C1)/N=N/C1=CC=C(C=C1)S(=O)(=O)[O-].[Na+] CQPFMGBJSMSXLP-ZAGWXBKKSA-M 0.000 description 1
108010053481 Antifreeze Proteins Proteins 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000594011 Leuciscus leuciscus Species 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000010951 brass Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000013329 compounding Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000002173 cutting fluid Substances 0.000 description 1
239000010730 cutting oil Substances 0.000 description 1
NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 1
NRZDMKVYRRMFRR-UHFFFAOYSA-L disodium;4-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzene-1,3-dicarboxylate;chloride Chemical compound [Na+].[Na+].[Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(C([O-])=O)C=C1C([O-])=O NRZDMKVYRRMFRR-UHFFFAOYSA-L 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000008233 hard water Substances 0.000 description 1
KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000009533 lab test Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
229910000679 solder Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000007655 standard test method Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Landscapes

Preventing Corrosion Or Incrustation Of Metals (AREA)

CA002309887A 1995-12-05 1996-11-22 Inhibiteurs de corrosion a base de neo-acid Expired - Lifetime CA2309887C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/567,639		1995-12-05
US08/567,639 US5741436A (en)	1995-12-05	1995-12-05	Antifreeze concentrates and compositions comprising neodecanoic acid corrosion inhibitors
CA 2238174 CA2238174C (fr)	1995-12-05	1996-11-22	Inhibiteurs de corrosion a base de neo-acid

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2238174 Division CA2238174C (fr)	1995-12-05	1996-11-22	Inhibiteurs de corrosion a base de neo-acid

Publications (2)

Publication Number	Publication Date
CA2309887A1 CA2309887A1 (fr)	1997-06-12
CA2309887C true CA2309887C (fr)	2002-02-12

Family

ID=25680224

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002309887A Expired - Lifetime CA2309887C (fr)	1995-12-05	1996-11-22	Inhibiteurs de corrosion a base de neo-acid

Country Status (1)

Country	Link
CA (1)	CA2309887C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114634746B (zh) *	2022-02-14	2022-10-25	烟台大学	荧光自示警和缓蚀自修复纳米防腐涂层及制备方法

1996
- 1996-11-22 CA CA002309887A patent/CA2309887C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2309887A1 (fr)	1997-06-12

Legal Events

Date	Code	Title	Description
2000-07-19	EEER	Examination request
2017-01-24	MKEX	Expiry	Effective date: 20161122

Publication	Publication Date	Title
EP0865474B1 (fr)	2000-07-05	Inhibiteurs de corrosion a base de neo-acid
US4587028A (en)	1986-05-06	Non-silicate antifreeze formulations
EP0251480B1 (fr)	1992-01-02	Composition d'antigel/réfrigérant inhibée contre la corrosion
KR100630848B1 (ko)	2006-10-09	카복실산 및 시클로헥센산 부식 방지제를 포함하는 부동액 조성물
US4873011A (en)	1989-10-10	Antifreeze corrosion inhibitor composition for aluminum engines and radiators
IL121093A (en)	2002-07-25	Silicate-, borate and nitrate-free antifreeze concentrates and coolant compositions comprising them
US5242621A (en)	1993-09-07	Combinations of alkanoic hydrocarbyl dicarboxylic and carbocyclic alkanoic acids or salts useful as heat transfer fluid corrosion inhibitors
JPH0195179A (ja)	1989-04-13	腐食抑制不凍液配合物
AU2019204001A1 (en)	2019-06-27	Extended operation engine coolant composition
WO1999024524A1 (fr)	1999-05-20	Composition antigel exempte de silicate
US6235217B1 (en)	2001-05-22	Monocarboxylic acid based antifreeze composition
KR930002766B1 (ko)	1993-04-10	억제된 알킬렌 글리콜 냉각제 및 냉각법
MXPA01008616A (es)	2002-07-02	Composicion anticongelante basada en acido monocarboxilico para motores diesel.
JP3686120B2 (ja)	2005-08-24	不凍液用組成物
CA2309887C (fr)	2002-02-12	Inhibiteurs de corrosion a base de neo-acid
CA2238174C (fr)	2000-06-27	Inhibiteurs de corrosion a base de neo-acid
WO1986000918A1 (fr)	1986-02-13	Antigel contenant une pseudo-huile
HK1016210B (en)	2001-03-23	Neoacid corrosion inhibitors
JP3651939B2 (ja)	2005-05-25	不凍液組成物
SA97170544B1 (ar)	2006-03-15	مواد مركزة مضادة للتجمد وتركيبات تشتمل على حمض ديكانويك مستحدث neo-decanoic acid كمواد مانعه للصدأ
MXPA00004372A (en)	2001-12-04	Silicate free antifreeze composition
HK1219495B (en)	2021-04-01	Extended operation engine coolant composition