KR101074725B1 - 보레이트 에스테르 윤활 첨가제 - Google Patents
보레이트 에스테르 윤활 첨가제 Download PDFInfo
- Publication number
- KR101074725B1 KR101074725B1 KR1020057022125A KR20057022125A KR101074725B1 KR 101074725 B1 KR101074725 B1 KR 101074725B1 KR 1020057022125 A KR1020057022125 A KR 1020057022125A KR 20057022125 A KR20057022125 A KR 20057022125A KR 101074725 B1 KR101074725 B1 KR 101074725B1
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- South Korea
- Prior art keywords
- butyl
- sub
- tert
- compound
- carbon atoms
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- 239000003879 lubricant additive Substances 0.000 title description 2
- 239000000654 additive Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- -1 boronate compound Chemical class 0.000 claims description 118
- 239000000203 mixture Substances 0.000 claims description 48
- 239000003921 oil Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000314 lubricant Substances 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical group C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims description 2
- 125000005645 linoleyl group Chemical group 0.000 claims description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000446 fuel Substances 0.000 abstract description 15
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 239000010687 lubricating oil Substances 0.000 abstract description 9
- 125000004464 hydroxyphenyl group Chemical group 0.000 abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
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- 150000001412 amines Chemical class 0.000 description 12
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 9
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- 229910019142 PO4 Inorganic materials 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- 235000021317 phosphate Nutrition 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 7
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- 239000011701 zinc Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 239000007866 anti-wear additive Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 0 *C(Cc1cc(*)cc(*)n1)OB(O*)[Al] Chemical compound *C(Cc1cc(*)cc(*)n1)OB(O*)[Al] 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
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- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
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Abstract
본 발명은 하기 일반식(I) 및 (II)의 보레이트 또는 보로네이트 화합물에 관한 것이다:
상기 식에서,
R1, R2 및 R3는 독립적으로 수소, 직쇄 또는 측쇄 C1-C24 알킬, 직쇄 또는 측쇄 C2-C24 알케닐, C5-C12 시클로알킬, C6-C10 아릴, C7-C15 아르알킬, C7-C15 알크아릴이고;
Ar은 치환 또는 비치환된 C6-C10 아릴이고; 그리고
R4 및 R5는 독립적으로 R1에 대해 정의한 바와 같고, 히드록시페닐 또는 알킬화 히드록시페닐일 수 있거나, 또는
R4 및 R5는 -OBO-기와 함께 치환 또는 비치환된 5 또는 6-원 고리를 형성한다.
보레이트 및 보로네이트 화합물은 내마모, 극압, 및 윤활유 및 연료용 마모 개선 첨가제로서 유용하다.
보레이트, 보로네이트, 윤활유
Description
본 발명은 붕산 또는 보론산, 2-히드록시에틸피리딘 및 히드로카르빌 알코올로부터 유도된 보레이트 및 보로네이트 에스테르를 제공한다. 본 발명의 보레이트 및 보로네이트 에스테르는 윤활유 및 연료에 대한 무회(ashless), 사실상 무인(phosphorus-free) 및 무황(sulfur-free) 내마모, 극압 마찰 개선 첨가제를 제공한다.
미국 특허 제 4,382,006호에서는 유기 작동액에 대한 마찰 개선 첨가제로서 유용한 에톡실화 아민 및 그의 보레이트 유도체에 대해서 기재하고 있다. 미국 특허 제 4,406,802호에서는 혼합된 알코올, 아미드, 아민, 히드록시 에스테르, 에톡실화 아민, 에톡실화 아미드 및 히드록시알킬, 히드록시알케닐알킬 또는 알케닐이미다졸린의 보레이트에 대해서 기재하고 있다.
미국 특허 제 4,389,322호에서는 마찰 감소 첨가제로서 에톡실화 아미드 및 그의 보레이트 부생물에 대해서 기재하고 있다. 미국 특허 제 4,568,472호에서는 혼합된 에톡실화 아민 및 아미드, 히드록시알킬 이미다졸린, 가수분해된 히드록시알킬 이미다졸린 및 히드록시에스테르의 보레이트인 윤활 매체용 다기능성 첨가제를 제공한다.
미국 특허 제 4,492,642호에서는 보레이팅제를 암모니아화 하이드로카르빌 에폭시드와 반응시켜 얻어진 생성물인 윤활제 첨가제에 대해서 기재하고 있다.
미국 특허 제 4,892,670호에서는 일급 아민 또는 암모니아를 알킬렌 옥사이드나 에폭시드와 반응시키고, 동시에 또는 후속적으로 중간체를 붕산과 반응시킴으로써 제조되는 붕소-함유 헤테로사이클 화합물에 대해 기재하고 있다. 이 화합물들은 윤활 조성물에 적합한 내마모 첨가제이다.
미국 특허 제 4,741,848호에서는 히드록시 치환된 에스테르, 아미드 또는 이미드를 붕산, 삼산화 붕소, 붕소 할로겐화물, 붕소 아미드 또는 붕소 에스테르와 반응시켜 제조된 붕소-함유 화합물에 대해 기재하고 있다. 붕소 화합물들은 윤활제 및 연료 첨가제로서 사용된다.
Yao, J. 및 Dong, J. Lubr . Eng . 1995, 51(6), 475-8 그리고 Zheng, Z., et al., Wear 1998, 222, 135-144)는 분자 구조에 질소를 함유하는 알킬 보레이트에 대해서 기재하고 있다.
2-히드록시에틸피리딘, 붕산 또는 보론산과 히드로카르빌 알코올로부터 유도된 보레이트 및 보로네이트 에스테르는 윤활유 및 연료에 대해 우수한 내마모, 극압, 및 마찰 개선 첨가제를 제공한 것으로 밝혀졌다.
하기 일반식(I) 및 (II)의 보레이트 및 보로네이트에 대해서 기술한다:
상기 식에서,
R1, R2 및 R3는 독립적으로 수소, 직쇄 또는 측쇄 C1-C24 알킬, 직쇄 또는 측쇄 C2-C24 알케닐, C5-C12 시클로알킬, C6-C10 아릴, C7-C15 아르알킬, C7-C15 알크아릴이고;
Ar은 치환 또는 비치환된 C6-C10 아릴이고; 그리고
R4 및 R5는 독립적으로 R1에 대해 정의한 바와 같고, 히드록시페닐 또는 알킬화 히드록시페닐일 수 있거나, 또는
R4 및 R5는 -OBO-기와 함께 치환 또는 비치환된 5 또는 6-원 고리를 형성한다.
예를 들면, R1, R2, R3, R4 및 R5는 독립적으로 수소, 직쇄 또는 측쇄 C1-C24 알킬, C6-C10 아릴, 또는 C7-C15 알크아릴이다.
예를 들면, R4 및 R5는 독립적으로 n-부틸, sec-부틸, t-부틸, n-도데실, n-옥타데실, n-옥틸, 이소옥틸, 올레일, 스테아릴, n-테트라데실, 1-헥사데실, 리놀레일, 리놀레닐, 피틸, 미리실, 라우릴, 미리스틸, 세틸, 베헤닐, 페닐, 카테칠, 알킬화 페닐 또는 알킬화 히드록시페닐이다.
R4 및 R5는 -OBO-기와 함께 치환 또는 비치환된 5 또는 6-원 고리를 형성할 때, 그 치환체의 예로는 C1-C6 알킬 또는 히드록시가 있다. 고리는 1∼4개의 기로 치환될 수 있다.
알킬은 직쇄 또는 측쇄이고, 그 예로는 메틸, 에틸, n-프로필, 이소-프로필, n-부틸, 이소부틸, 2차-부틸, n-부틸, n-펜틸, 이소펜틸, n-헥실, n-헵틸, 3-헵틸, n-옥틸, 2-에틸헥실, n-노닐, n-데실, 운데실, n-도데실, 트리데실, n-테트라데실, 펜타데실, n-헥사데실, n-옥타데실, n-아이코실, 헵타데실, 2-에틸부틸, 1-메틸펜틸, 1,3-디메틸부틸, 1,1,3,3-테트라메틸ㄹ부틸, 1-메틸헥실, 이소헵틸, 1-메틸헵틸, 1,1,3-트리메틸헥실 및 1-메틸운데실이 있다.
알케닐은 직쇄 또는 측쇄이고, 일킬의 불포화물이며, 그 예로는 알릴, 프로프-2-에닐, 부트-2-에닐, 2-메틸-프로프-2-에닐, 펜트-2-에닐, 헥사-2,4-디에닐, 데스-10-에닐 또는 아이코스-2-에닐이 있다.
시클로알킬의 예로는 시클로펜틸, 메틸시클로펜틸, 디메틸시클로펜틸, 시클로헥실, 메틸시클로헥실, 디메틸시클로헥실, 트리메틸시클로헥실, 3급 부틸시클로헥실, 시클로데실, 아다만틸, 시클로도데실, 시클로헵틸 또는 시클로옥틸이 있다.
아르알킬의 예로는 벤질, 알파-메틸벤질, 알파,알파-디메틸벤질 또는 2-페닐에틸이 있다.
아릴의 예로는 페닐 또는 나프틸이 있다. 치환된 아릴의 예로는 1∼4의 C1-C6 알킬 또는 히드록시기로 치환된 아릴이다.
알크아릴의 예는 o-, m- 또는 p-메틸페닐, 2,3-디메틸페닐, 2,4-디메틸페닐, 2,5-디메틸페닐, 2,6-디메틸페닐, 3,4-디메틸페닐, 3,5-디메틸페닐, 2-메틸-6-에틸페닐, 4-t-부틸페닐, 2-에틸페닐, 2,6-디에틸페닐, 2,4-디-t-부틸페닐 또는 2,6-디-t-부틸-4-메틸페닐이다.
히드록시페닐의 예는 3-히드록시페닐이다.
알킬화 히드록시페닐의 예는 모노- 또는 디-알킬화 3-히드록시페닐, 이를테면 2-메틸-3-히드록시페닐, 4-메틸-3-히드록시페닐, 2-에틸-3-히드록시페닐, 4-에틸-3-히드록시페닐, 2-t-부틸-3-히드록시페닐, 4-t-부틸-3-히드록시페닐, 2-헥실-3-히드록시페닐, 4-헥실-3-히드록시페닐, 2,4-디메틸-3-히드록시페닐, 2-메틸-4-t-부틸-3-히드록시페닐, 및 기타 대응하는 디알킬화 형태이다. 즉, 본 화합물은 레조르시놀 또는 알킬화 레조르시놀로 제조될 수 있다.
바람직한 실시예에 따라, 본 발명은 디-n-도세스-1-일-2-(피리드-2-일)에틸 보레이트, n-옥타데스-1-일-2-(피리드-2-일)에틸 페닐보로네이트, n-옥트-1-일-2-(피리드-2-일)에틸 페닐보로네이트 및 n-올레-1-일-2-(피리드-2-일)에틸 페닐보로네이트로 이루어진 군으로부터 선택된 일반식(I) 또는 (II)의 화합물에 관한 것이다.
본 발명의 화합물은 이를테면 2-히드록시에틸피리딘, 붕산 또는 보론산과 하이드로카르빌 알코올의 반응에 의해 제조된다. 예를 들면, 본 발명의 보레이트는, 물이 공비적으로 제거되는 조건 하에서 2-히드록시에틸피리딘과 붕산 및 하이드로카르빌 알코올 2 당량의 반응에 의해 제조된다. 통상적인 방법에서는, 물이 공비적으로 제거되는 조건 하의 불활성 용매 중에서 1 당량의 2-(2-히드록시에틸)피리딘, 2 당량의 알칸올(예, 직쇄 또는 측쇄 C4-C18 알코올) 및 1 당량의 붕산이 함께 가열된다.
보로네이트도 마찬가지로 이를테면 2-(2-히드록시에틸)피리딘, 아릴보론산 및 1 당량의 알칸올을 물을 제거하는 조건 하에서 반응함으로 제조된다.
양호한 구체예에 따라 알칸올의 혼합물이 사용될 수 있다.
이용되는 용매는 이를테면 톨루엔, 크실렌 등이 있다. 적당한 조건 하에서는 반응이 용매 없이 실시될 수도 있다.
하이드로카르빌 알코올의 예는 1-부탄올, sec-부탄올, t-부탄올, 1-도데칸올, 1-옥타데칸올, 1-옥탄올, 이소옥탄올, 올레일 알코올, 스테아르산 알코올, 1-테트라데칸올, 1-헥사데칸올, 리놀레일 알코올, 리놀레닐 알코올, 피톨, 미리실 알 코올, 라우릴 알코올, 미리스틸 알코올, 세틸 알코올, 베헤닐 알코올, 페놀, 카테콜, 알킬화 페놀, 알킬화 레조르시놀, 에틸렌 글리콜, 프로필렌 글리콜 등이 있다.
아릴보론산의 예는 페닐보론산 등이 있다.
본 발명의 목적은 하기 성분 a) 및 b)를 포함하는 내마모 개선 특성을 갖는 윤활제 조성물을 제공하는 데 있다:
a) 윤활유 및
b) R1, R2, R3, R4 및 R5가 상기 정의한 바와 같은 일반식(I) 또는 (II)을 갖는, 내마모 유효량의 화합물 1 이상.
본 발명에 따른 륜활유는 이를테면 내연기관에 이용되는 것들이다. 본 발명의 윤활유는 필요한 윤활 점도를 갖는다. 오일의 예는 무기유이거나 합성유 및 그의 혼합물이다.
그리스나 기타 고체 윤활제도 또한 본 발명에 따른 윤활유이다.
합성 탄화수소 오일은 삼합체와 옥탄 및 데센의 사합체와 같은 올레핀 중합체 그리고 세탄과 같은 장쇄 알칸을 포함한다. 이들 합성 오일은 1) 약 2∼20의 탄소 원자를 갖는 모노카르복시산의 펜타에리트리톨 에스테르와 같은 에스테르 오일, 2) 폴리글리콜 에테르, 3) 폴리아세탈 및 4) 실옥산 액과 혼합될 수 있다. 합성 에스테르 중에서 유용한 것은 폴리카르복시산과 일가 알코올로 이루어진 것이다. 예를 들면 펜타에리트리톨 또는 이와 디- 및 트리펜타에리트리톨과의 혼합물로 이루어진 에스테르 액, 탄소수 1∼20을 갖는 지방족 모노카르복시산, 또는 이러한 산의 혼합물이 있다. 다른 예로는 탄소수 1∼20을 갖는 지방족 모노카르복시산과 트리메틸올프로판으로 이루어진 에스테르 액, 또는 이러한 산들의 혼합물이 있다.
본 발명에 따른 윤활유의 예로는 원유, 공업용 윤활유, 절삭유, 금속 작동액 및 그리스가 있다.
본 발명에 따른 보레이트 및 보로네이트 첨가제의 또 다른 용도는 연료, 이를테면 윤활 특성이 요구되는 특정 항공 연료 등이다. 연료는 이를테면 모터 가솔린, 디젤 연료 또는 연료 오일과 같은 탄화수소성 석유 증류물이다. 알코올, 에테르, 유기-니트로 화합물 등(예, 메탄올, 에탄올, 디에틸 에테르, 메틸 에틸 에테르, 니트로메탄)과 같은 비탄화수소성 물질을 포함하는 액체 연료 조성물은 옥수수, 알팔파, 이판암 및 석탄과 같은 식물성 또는 무기 소스로부터 유도된 액체 연료와 같이 본 발명의 범위 내에 있다. 1 이상의 탄화수소성 연료와 1 이상의 비탄화수소성 물질의 혼합물인 연료가 또한 고려될 수 있다. 이러한 혼합물의 예로는 가솔린과 에탄올의 조합물 및 디젤 연료와 에테르의 조합물이 있다.
본 발명의 첨가제는 오일에 극압, 내마모 및 내마찰 감소성을 제공하고, 연소 시에 자동차에서 종래의 촉매 전환제에 대해 무해하다.
본 발명의 첨가제는 조성물의 총 중량의 약 0.01∼20 중량%의 양으로 오일 조성물에 존재하는 것이 유리하다. 예를 들면, 보레이트와 보로네이트는 조성물의 총 중량 기준으로 약 0.05∼15 중량%, 약 0.1∼10 중량%, 약 0.2∼5 중량% 존재한다. 예를 들면, 보레이트와 보로네이트는 조성물의 총 중량 기준으로, 약 0.1∼20 중량%, 약 0.1∼15 중량%, 약 0.1∼5 중량% 존재한다.
해상 디젤 엔진용 윤할 조성물과 같이 극악 조건 하에서 작동되는 윤활 조성물에서, 본 발명의 첨가제는 윤활 조성물의 총 중량의 약 30 중량% 이하 또는 그 이상으로 존재할 수 있다는 것도 고려된다.
본 발명의 첨가제는 연료를 기준으로 약 1∼50,000 ppm 수준으로 연료 조성물에 존재하는 것이 유리하다. 예를 들면 첨가제는 연료를 기준으로 약 4ppm∼5,000 ppm 존재한다.
본 발명에 따라 안정화된 윤활유는 이들 배합물의 기본 특성을 더 개선하기 위해서 첨가되는 기타 첨가제를 더 포함할 수 있다. 이들 첨가제는 산화방지제, 금속 탈활성화제, 방청제, 부식 방지제, 점도 지수 향상제, 극압제, 유동점 억제제, 고체 윤활제, 분산제, 세제, 소포제, 색상 안정화제, 고압 첨가제, 해유화제(demulsifier), 내마모 첨가제 및 마찰계수를 감소시키는 첨가제를 포함한다. 이러한 첨가제는 윤활유를 기준으로 각각 0.01∼10.0 중량% 범위의 통상적인 양으로 부가된다.
추가의 첨가제의 예는 다음과 같다:
1. 산화방지제의 예:
1.1. 알킬화 모노페놀, 예를들어 2,6-디-삼차-부틸-4-메틸페놀, 2-부틸-4,6-디메틸페놀, 2,6-디-삼차-부틸-4-에틸페놀, 2,6-디-삼차-부틸-4-n-부틸페놀, 2,6-디-삼차-부틸-4-이소부틸페놀, 2,6-디-시클로펜틸-4-메틸페놀, 2-(α-메틸시클로헥실)- 4,6-디메틸페놀, 2,6-디-옥타데실-4-메틸페놀, 2,4,6-트리시클로헥실페놀, 2,6-디-삼차-부틸-4-메톡시메틸페놀, 직쇄 또는 측쇄에서 분지된 노닐페놀 예컨대, 2,6-디 -노닐-4-메틸페놀, 2,4-디메틸-6-(1'-메틸-운데스-1'-일)-페놀, 2,4-디메틸-6-(1'-메틸헵타데스-1'-일)-페놀, 2,4-디메틸-6-(1'-메틸트리데스-1'-일)-페놀 또는 이들의 혼합물.
1.2. 알킬티오메틸페놀, 예를들어 2,4-디-옥틸티오메틸-6-삼차-부틸페놀, 2,4-디-옥틸티오메틸-6-메틸페놀, 2,4-디옥틸티오메틸-6-에틸페놀, 또는 2,6-디-도데실티오메틸- 4-노닐페놀.
1.3. 히드로퀴논 및 알킬화 히드로퀴논, 예를들어 2,6-디-삼차-부틸-4-메톡시페놀, 2,5-디-삼차-부틸-히드로퀴논, 2,5-디-삼차-아밀히드로퀴논, 2,6-디페닐-4-옥타데실옥시페놀, 2,6-디-삼차-부틸-히드로퀴논, 2,5-디-삼차-부틸-4-히드록시아니솔, 3,5-디-삼차-부틸-4-히드록시아니솔, 3,5-디-삼차-부틸-4-히드록시페닐 스테아레이트, 또는 비스(3,5-디-삼차-부틸-4-히드록시페닐)아디페이트.
1.4. 토코페롤, 예를 들어 α-토코페놀, β-토코페놀, γ-토코페놀, δ-토코페놀 및 이들의 혼합물 (비타민E)
1.5. 히드록시화 티오디페닐 에테르, 예를들어 2,2'-티오비스(6-삼차-부틸-4-메틸페놀), 2,2'-티오비스(4-옥틸페놀), 4,4'-티오비스(6-삼차-부틸-3-메틸페놀), 4,4'-티오비스(6-삼차-부틸-2-메틸페놀), 4,4'-티오비스(3,6-디-이차-아밀페놀), 또는 4,4'-비스 (2,6-디메틸-4-히드록시페닐)디술피드.
1.6. 알킬리덴 비스페놀, 예를들어 2,2'-메틸렌비스(6-삼차-부틸-4-메틸페놀), 2,2'-메틸렌비스(6-삼차-부틸-4-에틸페놀), 2,2'-메틸렌비스[4-메틸-6-(α-메틸시클로헥실)-페놀], 2,2'-메틸렌비스(4-메틸-6-시클로헥실페놀), 2,2'-메틸렌비스(6- 노닐-4-메틸페놀), 2,2'-메틸렌비스(4,6-디-삼차-부틸페놀), 2,2'-에틸리덴비스(4,6-디-삼차-부틸페놀), 2,2'-에틸리덴비스(6-삼차-부틸-4-이소부틸페놀), 2,2'-메틸렌비 스[6-(α-메틸벤질)-4-노닐페놀], 2,2'-메틸렌비스[6-(α,α-디메틸벤질)-4-노닐페놀], 4,4'-메틸렌비스(2,6-디-삼차-부틸페놀), 4,4'-메틸렌비스(6-삼차-부틸-2-메틸페놀), 1,1-비스(5-삼차-부틸-4-히드록시-2-메틸페닐)부탄, 2,6-비스(3-삼차-부틸-5-메틸-2-히드록시벤질)-4-메틸페놀, 1,1,3-트리스(5-삼차-부틸-4-히드록시-2-메틸페닐)부탄, 1,1-비스(5-삼차-부틸-4-히드록시-2-메틸-페닐)-3-n-도데실머캅토부탄, 에틸렌 글리콜 비스[3,3-비스(3'-삼차-부틸-4'-히드록시페닐)부티레이트], 비스(3-삼차-부틸-4-히드록시-5-메틸-페닐)디시클로펜타디엔, 비스[2-(3'-삼차-부틸-2'-히드록시-5'-메틸벤질)-6-삼차-부틸-4-메틸페닐]테레프탈레이트, 1,1-비스-(3,5-디메틸-2-히드록시페닐)부탄, 2,2-비스(3,5-디-삼차-부틸-4-히드록시페닐)-프로판, 2,2-비스 (5-삼차-부틸-4-히드록시-2-메틸페닐)-4-n-도데실머캅토부탄, 또는 1,1,5,5-테트라(5-삼차-부틸-4-히드록시-2-메틸페닐)펜탄.
1.7. O-, N- 및 S-벤질 화합물, 예를들어 3,5,3',5'-테트라-삼차-부틸-4,4'-디히드록시-디벤질 에테르, 옥타데실-4-히드록시-3,5-디메틸벤질머캅토아세테이트, 트리데실-4-히드록시-3,5-디-삼차-부틸벤질머캅토아세테이트, 트리스(3,5-디-삼차-부틸-4-히드록시벤질)아민, 비스(4-삼차-부틸-3-히드록시-2,6-디메틸벤질)디티오테레프탈레이트, 비스(3,5-디-삼차-부틸-4-히드록시벤질)술피드, 또는 이소옥틸-3,5-디-삼차-부틸-4-히드록시벤질 머캅토아세테이트.
1.8. 히드록시벤질화 말로네이트, 예를들어 디옥타데실-2,2-비스(3,5-디-삼차-부틸 -2-히드록시벤질)말로네이트, 디-옥타데실-2-(3-삼차-부틸-4-히드록시-5-메틸벤질)-말로네이트, 디-도데실머캅토에틸-2,2-비스(3,5-디-삼차-부틸-4-히드록시벤질)말로네이트, 또는 비스-[4-(1,1,3,3-테트라메틸부틸)페닐]-2,2-비스(3,5-디-삼차-부틸-4-히드록시벤질)말로네이트.
1.9. 방향족 히드록시벤질 화합물, 예를들어 1,3,5-트리스(3,5-디-삼차-부틸-4-히드록시벤질)-2,4,6-트리메틸벤젠, 1,4-비스(3,5-디-삼차-부틸-4-히드록시벤질)-2,3,5, 6-테트라메틸벤젠, 또는 2,4,6-트리스(3,5-디-삼차-부틸-4-히드록시벤질)페놀.
1.10. 트리아진 화합물, 예를들어 2,4-비스옥틸머캅토-6-(3,5-디-삼차-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-삼차-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-삼차-부틸-4-히드록시페녹시)-1,3,5-트리아진, 2,4,6-트리스(3,5-디-삼차-부틸-4-히드록시페녹시)-1,2,3-트리아진, 1,3,5-트리스(3,5-디-삼차-부틸-4-히드록시벤질)이소시아누레이트, 1,3,5-트리스(4-삼차-부틸-3-히드록시-2,6-디메틸벤질)이소시아누레이트, 2,4,6-트리스(3,5-디-삼차-부틸-4-히드록시페닐에틸)-1,3,5-트리아진, 1,3,5-트리스(3,5-디-삼차-부틸-4-히드록시페닐프로피오닐)헥사히드로-1,3,5-트리아진, 또는 1,3,5-트리스 (3,5-디시클로헥실-4-히드록시벤질)이소시아누레이트.
1.11. 벤질포스포네이트, 예컨대 디메틸-2,5-디-삼차-부틸-4-히드록시벤질 포스포네이트, 디에틸-3,5-디-삼차-부틸-4-히드록시벤질포스포네이트, 디옥타데실-3,5-디-삼차-부틸-4-히드록시벤질포스포네이트, 디옥타데실-5-삼차-부틸-4-히드록시-3-메 틸벤질 포스포네이트, 또는 3,5-디-삼차-부틸-4-히드록시벤질-포스폰산 모노에틸 에스테르의 칼슘 염.
1.12. 아실아미노페놀, 예를들어 4-히드록시라우르아닐리드, 4-히드록시스테아르아닐리드, 또는 옥틸 N-(3,5-디-삼차-부틸-4-히드록시페닐)카르바메이트.
1.13. 1가 또는 다가 알코올, 예컨대 메탄올, 에탄올, n-옥탄올, 이소옥탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥살아미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판, 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄, 이를테면 코코넛유, 평지씨유, 해바라기씨유 또는 콜자유의 천연 트리글리세리드를 기본으로 한 글리세롤 또는 에스테르 교환 생성물과 β-(3,5-디-삼차-부틸-4- 히드록시페닐 )-프로피온산의 에스테르.
1.14. β-(3,5-디- 삼차-부틸 -4- 히드록시페닐 )프로피온산의 아미드, 예를들어 N,N'-비스(3,5-디-삼차-부틸-4-히드록시페닐프로피온산)헥사메틸렌디아민, N,N'-비스(3,5-디-삼차-부틸-4-히드록시페닐피로피오닐)트리메틸렌디아민, 또는 N,N'-비스(3,5-디-삼차-부틸-4-히드록시-페닐프오피오닐)히드라진.
1.15. 아스코르브산 (비타민 C)
1.16. 아민형 산화방지제, 예컨대 N,N'-디-이소프로필-p-페닐렌디아민, N,N'-디-이차-부틸-p-페닐렌디아민, N,N'-비스(1,4-디메틸펜틸)-p-페닐렌디아민, N,N'-비스 (1-에틸-3-메틸펜틸)-p-페닐렌디아민, N,N'-비스(1-메틸헵틸)-p-페닐렌디아민, N,N'- 디시클로헥실-p-페닐렌디아민, N,N'-디페닐-p-페닐렌디아민, N,N'-비스(2-나프틸)-p-페닐렌디아민, N-이소프로필-N'-페닐-p-페닐렌디아민, N-(1,3-디메틸부틸)-N'-페닐 -p-페닐렌디아민, N-(1-메틸헵틸)-N'-페닐-p-페닐렌디아민, N-시클로헥실-N'-페닐-p-페닐렌디아민, 4-(p-톨루엔술파모일)-디페닐아민, N,N'-디메틸-N,N'-디-이차-부틸 -p-페닐렌디아민, 디페닐아민, N-알릴디페닐아민, 4-이소프로폭시디페닐아민, N-페닐-1-나프틸아민, N-(4-삼차-옥틸페닐)-1-나프틸아민, N-페닐-2-나프틸아민, 옥틸화 디페닐아민, 예컨대, p,p'-디-삼차-옥틸디페닐아민, 4-n-부틸아미노페놀, 4-부티릴아미노페놀, 4-노난오일아미노-페놀, 4-도데칸오일아미노페놀, 4-옥타데칸오일아미노페놀, 비스(4-메톡시페닐)아민, 2,6-디-삼차-부틸-4-디메틸아미노메틸페놀, 2,4'-디-아미노디페닐메탄, 4,4'-디아미노디페닐메탄, N,N,N',N'-테트라메틸-4,4'-디-아미노디페닐메탄, 1,2-비스[(2-메틸페닐)아미노]에탄, 1,2-비스(페닐아미노)프로판, (o-톨릴)비구아니드, 비스[4-(1',3'-디메틸부틸)페닐]아민, 삼차-옥틸화 N-페닐-1-나프틸아민, 모노- 및 디알킬화 삼차-부틸/삼차-옥틸디페닐아민의 혼합물, 모노- 및 디알킬화 노닐디페닐아민의 혼합물, 모노- 및 디알킬화 노닐디페닐아민의 혼합물, 모노- 및 디알킬화 도데실디페닐아민의 혼합물, 모노- 및 디알킬화 이소프로필/이소헥실페닐아민의 혼합물, 모노- 및 디알킬화 삼차-부틸디페닐아민의 혼합물, 2,3-디-히드로-3,3-디메틸-4H-1,4-벤조티아진, 페노티아진, 모노 및 디알킬화 삼차-부틸/삼차-옥틸페노타이진의 혼합물, 모노- 및 디알킬화 삼차-옥틸-페노티아진의 혼합물, N-알릴페노티아진, N,N,N',N'-테트라페닐-1,4-디아 미노부트-2-엔, N,N-비스(2,2,6,6-테트라메틸-피페리드-4-일-헥사메틸렌디아민, 비스(2,2,6,6-테트라메틸피페리드-4-일)세바케이트, 또는 2,2,6,6-테트라메틸피페리딘-4-온, 2,2,6,6-테트라메틸피페리딘-4-올.
1.17. 지방족 또는 방향족 포스파이트, 티오디프로피온산 또는 티오디아세트산의 에스테르 또는 디카르밤산 또는 디티오인산의 염, 2,2,12,12-테트라메틸-5,9-디히드록시-3,7,11-트리티아트리데칸 및 2,2,15,15-테트라메틸-5,12-디히드록시-3,7,10,14-테트라티아헥사데칸.
2. 구리와 같은 금속
탈활성화제
:
2.1. 벤조트리아졸 및 그의 유도체: 4- 또는 5-알킬벤조트리아졸(예컨대 톨루트리아졸) 및 그의 유도체, 4,5,6,7-테트라히드로벤조트리아졸, 5,5'-메틸렌비스벤조트리아졸; 벤조트리아졸 또는 톨루트리아졸의 만니히 염기, 예컨대 1-[디(2-에틸헥실아미노메틸)]톨루트리아졸 및 1-[디(2-에틸헥실)아미노메틸]벤조트리아졸; 알콕시알킬벤조트리아졸, 예컨대 1-(노닐옥시메틸)벤조트리아졸, 1-(1-부톡시에틸)벤조트리아졸 및 1-(1-시클로헥실옥시부틸)톨루트리아졸.
2.2. 1,2,4- 트리아졸 및 그의 유도체: 3-알킬(또는 아릴)-1,2,4-트리아졸, 1,2,4-트리아졸의 만니히 염기, 예컨대 1-[디(2-에틸헥실아미노메틸]-1,2,4-트리아졸; 알콕시알킬-1,2,4-트리아졸, 예컨대 1-(1-부톡시에틸)-1,2,4-트리아졸; 아세틸화된 3-아미노-1,2,4-트리아졸.
2.3. 이미다졸 유도체: 4,4'-메틸렌비스(2-운데실-5-메틸이미다졸), 비스[(N-메틸)이미다졸-2-일]카르비놀 옥틸 에테르
2.4. 황-함유 헤테로시클릭 화합물: 2-머캅토벤조트리아졸, 2,5-디머캅토-1,3,4-티아디아졸, 2,5-디머캅토벤조티아디아졸 및 그의 유도체; 3,5-비스[디(2-에틸헥실)아미노메틸]-1,3,4-티아디아졸린-2-온.
2.5 아미노 화합물: 살리실리덴프로필렌디아민, 살리실아미노구아니딘 및 그의 염.
3.
방청제의
예:
3.1. 유기 산 , 그의 에스테르, 금속 염, 아민 염 및 무수물: 예컨대 알킬- 및 알케닐숙신산 및 특히 이들과 알코올, 디올 또는 히드록시카르복시산과의 부분 에스테르, 알킬- 및 알케닐숙신산, 4-노닐페녹시아세트산, 알콕시- 및 알콕시에톡시카르복시산, 예컨대 도데실옥시아세트산, 도데실옥시(에톡시)아세트산 및 그의 아민 염의 부분 아미드, 또한 N-올레일사르코신, 소르비탄 모노올레에이트, 납 나프테네이트, 알케닐숙신 무수물, 예컨대 도데실숙신 무수물, 2-(2-카르복시에틸)-1-도데실-3-메틸글리세롤 및 그의 염, 특히 나트륨 염 및 트리에탄올아민 염.
3.2. 질소-함유 화합물:
3.2.1. 일차, 이차 또는 삼차 지방족 및 시클로지방족 아민 및 유기 및 무기 산의 아민 염, 예컨대 오일-용해성 알킬암모늄 카르복실레이트, 및 또한 1-[N,N-비스-(2-히드록시에틸)아미노]-3-(4-노닐페녹시)프로판-2-올.
3.2.2. 헤테로시클릭 화합물, 예컨대 치환된 이미다졸린 및 옥사졸린, 예컨대 2-헵타데세닐-1-(2-히드록시에틸)이미다졸린.
3.3. 인-함유 화합물, 예컨대 인산 부분 에스테르 또는 포스폰산 부분 에스테르의 아민 염, 아연 디알킬디티오포스페이트.
3.4 황-함유 화합물: 바륨 디노닐나프탈렌술포네이트, 칼슘 석유 술포네이트, 알킬티오-치환된 지방족 카르복시산, 지방족 2-술포카르복시산의 에스테르 및 그의 염.
3.5 글리세롤 유도체: 글리세롤 모노올레이트, 1-(알킬페녹시)-3-(2-히드록시에틸)글리세린, 1-(알킬페녹시)-3-(2,3-디히드록시프로필)글리세린, 2-카르복시알킬-1,3-디알킬글리세린.
4. 점도 지수 향상제: 폴리아크릴레이트, 폴리메타크릴레이트, 비닐피롤리돈/메타크릴레이트 공중합체, 폴리비닐피롤리돈, 폴리부텐, 올레핀 공중합체, 스티렌/아크릴레이트 공중합체, 폴리에테르.
5. 유동점 억제제: 폴리메타크릴레이트, 알킬화된 나프탈렌 유도체.
6. 분산제 /계면활성제: 폴리부테닐숙신아미드 또는 -이미드, 폴리부테닐포스폰산 유도체, 염기성 마그네슘, 칼슘 및 바륨 술포네이트 및 페놀레이트 및 살리실레이트.
7. 소포제: 실리콘 오일 및 폴리메토크릴렌.
8. 해유화제: 폴리에테르폴리올 및 디노닐나프탈렌술포네이트.
9. 마찰 개선제: 지방산 및 그 유도체(즉, 글리세롤 모노올레이트와 같은 지방 산의 천연 에스테르), 아미드, 이미드 및 아민(즉, 올레일아민), 황 함유 유기 몰리브덴 디티오카르바메이트, 황-인 함유 유기몰리브덴 디티오포스페이트, 분산제를 기본으로 한 황-질소 함유 유기 몰리브덴 화합물, 몰리브덴 카르복실레이트 염, 몰리브덴-아민 복합체, 몰리브덴 아민/알코올/아미드 복합체 및 몰리브덴 클러스터 화합물, TeflonTM 및 몰리브덴 이황화물.
10. 추가 내마모 첨가제:
10.1 황- 및/또는 인- 및/또는 할로겐-함유 화합물, 예를 들면 황화 올레핀 및 식물성 기름, 아연 디알킬디티오포스페이트, 트리톨일 포스페이트, 트리크레실 포스페이트, 염화 파라핀, 알킬 및 아릴 디- 및 트리-황화물, 모노- 및 디-알킬 포스페이트의 아민염, 메틸포스폰산의 아민염, 디에탄올아미노메틸톨일트리아졸, 디(2-에틸헥실)-아미노메틸톨일트리아졸, 2,5-디메르캅토-1,3,4-티아디아졸의 유도체, 에틸((비스이소프로필옥시포스피노티오일)티오)프로피오네이트, 트리페닐 티오포스페이트(트리페닐포스포로티오에이트), 트리스(알킬페닐)포스포로티오에이트 및 이들의 혼합물(예, 트리스(이소노닐페닐)포스포로티오에이트), 디페닐모노노닐페닐 포스포로티오에이트, 이소부틸페닐 디페닐 포스포로티오에이트, 3-히드록시-1,3-티아포스페탄 3-옥시드의 도데실아민염, 트리티오포스포릭산 5,5,5-트리스-이소옥틸 2-아세테이트, 2-메르캅토벤조티아졸의 유도체, 예를 들면 1-(N,N-비스(2-에틸헥실)아미노메틸)-2-메르캅토-1H-1,3-벤조티아졸 또는 에톡시카르보닐 5-옥틸디티오카르바메이트.
10.2 디히드로카르빌 디티오포스페이트 금속 염, 여기서 금속은 알루미늄, 납, 주석, 망간, 코발트, 니켈, 아연 또는 구리이고, 아연이 가장 많이 사용된다. 아연 염(아연 디알킬 디티오포스페이트)은 다음 식으로 나타내진다:
상기 식에서, R 및 R'는 독립적으로 C1-C20 알킬, C3-C20 알케닐, C5-C12 시클로알킬, C7-C13 아르알킬 또는 C6-C10 아릴이고, 예를 들면 R 및 R'는 독립적으로 C1-C12 알킬이다.
10.3 내마모 첨가제: 본 명세서에서 참고로 하는 미국특허 4,584,021; 5,798,321; 5,750,478; 5,801,130; 4,191,666; 4,720,288; 4,025,288; 4,025,583 및 WO 095/20592에 기재된 것; 아민, 예를 들면 본 명세서에서 참고로 하는 4,267,063에 기재된 에틸렌 디아민, 디에틸렌 트리아민, 트리에틸렌 테트라아민, 테트라에틸렌 펜타아민, 펜타에틸렌 헥사아민, 노나에틸렌 데카아민 및 아릴 아민과 같은 폴리알킬렌 아민; 특히 아민 및 혼합된 모노- 및 디-산 포스페이트를 포함하는 아민 포스페이트의 염; 하기 일반식을 갖는 모노- 및 디-산 포스페이트 아민:
상기 식에서,
R27은 수소, 1 이상의 C1-C6 알콕시기, 포화 비환식 또는 지환족기로 치환되거 나 비치환된 C1-C25 선형 또는 측쇄 알킬, 또는 아릴이고;
R28는 1 이상의 C1-C6 알콕시기, 포화 또는 불포화 비환식 또는 지환족기로 치환되거나 비치환된 C1-C25 선형 또는 측쇄 알킬, 또는 아릴이고;
R29는 수소, C1-C25 선형 또는 측쇄 알킬, 포화 비환식 또는 지환족기, 또는 아릴이고; 그리고 수소 또는 C1-C12 선형 또는 측쇄 알킬이고;
R30 및 R31은 서로 독립적으로 C1-C25 선형 또는 측쇄 알킬, 포화 또는 불포화 비환식 또는 지환족기 또는 아릴이다. 바람직하게는, R27 및 R28은 선형 또는 측쇄 C1-C12 알킬이고; 그리고 R29, R30 및 R31는 선형 또는 측쇄 C1-C18 알킬이다.
양호한 구체예에 따라서, Irgalube®349(시바 스페셜티 케미칼스)는 특히 가혹한 군사 훈련 규정을 만족하도록 기본 오일의 마모 성능을 촉진함으로써 매우 유용한 것으로 밝혀졌다. Irgalube®349는 다음 일반식을 갖는다:
상기 식에서, R33은 n-헥실이고, R34는 C11-C14 측쇄 알킬이고, 그리고 x=1일 때, y=2이고; x=2일 때 y=1이고; Irgalube®349는 아민 포스페이트의 혼합물, CAS # 80939-62-4이다.
10.4 기타 공지된 내마모 첨가제는 하기 일반식(I)의 화합물이다:
상기 식에서,
R1 및 R2는 서로 독립적으로 C3-C18 알킬, C5-C12 시클로알킬, C5-C6 시클로알킬메틸, C9-C10 비시클로알킬메틸, C9-C10 트리시클로알킬메틸, 페닐 또는 C7-C24 알킬페닐 또는 함께 (CH3)2C(CH2)2이고,
R3는 수소 또는 메틸이다.
양호한 구체예에 따라서, Irgalube®353, 디알킬 디티오포스페이트 에스테르, CAS # 268567-32-4가 사용된다.
본 발명의 연료 조성물은 보레이트 및 보로네이트 첨가제 이외에 본 분야에서 공지된 기타 첨가제를 함유할 수 있다. 이들은 테트라알킬 납 화합물과 같은 앤티노킹제, 할로알칸(예, 에틸렌 디클로라이드 및 에틸렌 디브로마이드)과 같은 납 제거제, 트리아릴 포스페이트와 같은 퇴적 방지 또는 개선제, 염료, 세탄 개선제, 2,6-디-t-부틸-4-메틸페놀과 같은 산화방지제, 알킬화 숙신산 및 무수물과 같은 방청제, 정균제(bacteriostatic agent), 검 억제제, 금속 탈활성화제, 해유화제, 구리 실린더 윤활제 및 서리 제거제(anti-icing agent)를 포함한다.
본 발명의 보레이트 및 보로네이트는 공지의 방법으로 윤활유에 도입될 수 있다. 화합물들은 오일에 쉽게 용해할 수 있다. 이들은 윤활유에 직접 첨가될 수 있거나, 또는 사실상 불활성인, 나프타, 벤젠, 톨루엔, 크실렌과 같은 통상의 액체 유기 희석제 또는 통상의 액체오일 또는 연료와 함께 희석되어 첨가 농축액 또는 매스터 뱃치를 형성할 수 있다. 이들 농축액은 약 10∼90 중량%의 첨가제를 일반적으로 함유하고 1 이상의 기타 추가 첨가제를 함유할 수 있다. 본 발명의 보레이트 및 보로네이트는 첨가 패키지의 일부로서 도입될 수 있다.
본 발명은 다음 실시예에 의해 더욱 예증된다.
실시예
1
디-n-도데스-1-일-2-(피리드-2-일)에틸 보레이트
환류 응축기가 달린 Dean-Stark 관과 자석 교반 봉이 구비된 500 ml-유리 반응 용기에 2-(2-히드록시에틸)피리딘 12.3g, 1-도데칸올 37.2g, 붕산 6.2g, 및 톨루엔 250 ml를 넣는다. 혼합물을 환류하에 5 시간 동안 교반 및 가열한다. 이 때 약 5 ml의 물이 제거되고 에스테르가 형성된다. 용액을 여과하여 흐림을 제거하고, 용매를 진공 증류에 의해 제거하면, 맑고 엷은 황색 오일로서 보레이트 에스테르가 얻어진다.
실시예
2
n-옥타데스-1-일-2-(피리드-2-일)에틸 페닐보로네이트
환류 응축기가 달린 Dean-Stark 관과 자석 교반 봉이 구비된 200 ml-유리 반응 용기에 2-(2-히드록시에틸)피리딘 5.69 ml, 1-옥타데칸올 13.7g, 페닐보론산 6.29g, 및 톨루엔 150 ml를 넣는다. 혼합물을 환류하에 16 시간 동안 교반 및 가열한다. 이 때 약 1.8 ml의 물이 제거되고 에스테르가 형성된다. 용액을 여과하여 흐림을 제거하고, 용매를 진공 증류에 의해 제거하면, 냉각 시 왁스 물질로 고화되는 엷은 황색 오일 23.4g이 얻어진다.
실시예
3
n-옥트-1-일-(피리드-2-일)에틸 페닐보로네이트
환류 응축기가 달린 Dean-Stark 관과 자석 교반 봉이 구비된 200 ml-유리 반응 용기에 2-(2-히드록시에틸)피리딘 5.69ml, 1-옥탄올 7.96g, 페닐보론산 6.29g, 및 톨루엔 150 ml를 넣는다. 혼합물을 환류하에 16 시간 동안 교반 및 가열한다. 이 때 약 1.8 ml의 물이 제거되고 에스테르가 형성된다. 용액을 여과하여 흐림을 제거하고, 용매를 진공 증류에 의해 제거하면, 점성질의 어두운 황색 오일 16g이 얻어진다.
실시예
4
n-올레-1-일-(피리드-2-일)에틸 페닐보로네이트
환류 응축기가 달린 Dean-Stark 관과 자석 교반 봉이 구비된 200 ml-유리 반응 용기에 2-(2-히드록시에틸)피리딘 5.69 ml, 올레일 알코올 18.6 ml, 페닐보론산 6.29g, 및 톨루엔 150 ml를 넣는다. 혼합물을 환류하에 16 시간 동안 교반 및 가열한다. 이 때 약 1.8 ml의 물이 제거되고 에스테르가 형성된다. 용매를 진공 증류에 의해 제거하면, 점성질의 어두운 황색 오일 24g이 얻어진다.
실시예
5
디-n-옥트-1-일-(피리드-2-일)에틸 보레이트
환류 응축기가 달린 Dean-Stark 관과 자석 교반 봉이 구비된 2000 ml-유리 반응 용기에 2-(2-히드록시에틸)피리딘 75.0 g, 1-옥탄올 158.7 g, 붕산 61.8g, 및 톨루엔 1500 ml를 넣는다. 혼합물을 환류하에 18 시간 동안 교반 및 가열한다. 이 때 약 33 ml의 물이 제거되고 에스테르가 형성된다. 용액을 여과하여 흐림을 제거하고, 용매를 진공 증류에 의해 제거하고, 생성된 오일을 유리 프릿트를 통해 여과하여 맑고 엷은 황색 오일로서 보레이트 에스테르를 얻는다.
실시예
6
내마모성
고정 핀(500 x 500 μ)이 회전 디스크를 유지하고 일정 온도에서 가해지는 고정 하중을 갖고 Pin-on-Disc 부착으로 변형된 PCS Instruments Mini-Traction Machine 상에서 내마모성을 측정한다. 핀으로부터의 재료 손실로 인해, 핀의 이동으로 마모를 측정한다. 시험 오일은 내마모 첨가제가 포함되지 않는 것을 제외하고 충분히 배합된 제로 S, 매우 낮은 P 자동차 엔진오일이다. 반응 시험 조건은 10N 하중, 오일 온도 100℃이다. 마모 자료는 60분 동안 기록되고, 평균 마모 속도는 마모 곡선의 선형 하향 기울기로서 기록된다. 첨가제는 배합된 오일을 기본으로 한 중량%로 기록된다.
| 오일 | 마모 속도 |
| 대조용 (내마모 첨가제 없음) | 279 m/h |
| + 1.2% ZDDP | 3.0 m/h |
| +1% 실시예 1의 화합물 | 5.7 m/h |
ZDDP는 아연 디알킬 디티오포스페이트-2차 ZDDP는 1.2%에서 0.1%p를 제공한다.
실시예
7
4개의 볼
내마모
시험
본 발명에 따른 보레이트 에스테르의 내마모성은 시험 오일에서 1.0 중량%의 레벨에서 시험된다. 시험 오일은 내마모 첨가제가 배합물에 포함되지 않는 것을 제외하고 충분히 배합된, 인이 없고, S가 매우 낮은 자동차 엔진오일이다. 내마모성은 40 kg(392 N) 하중을 이용하여 ASTM D 1472 시험 조건 하에서 Four-Ball Wear Test법으로 측정한다. 시험을 2회 실시하고, 시험 결과, 평균 마모 상처 직경(Average Wear Scar Diameter)(mm)를 기록한다. 시험 결과 수치는 첨가제의 효과가 증가함에 따라 감소한다.
| 시험 화합물 | 마모 상처 직경 |
| 시험 오일 (내마모 첨가제 없음) | 0.675 |
| 시험 오일 (1% 화합물 실시예 1) | 0.65 |
| 시험 오일 (1% 화합물 실시예 5) | 0.615 |
| 시험 오일 (1% Zn DDP) | 0.61 |
Claims (10)
- 하기 일반식(I) 및 (II)로 이루어진 군으로부터 선택된 보레이트 또는 보로네이트 화합물:(I)
(II)
상기 식에서,R1, R2 및 R3는 수소이고;Ar은 페닐이며; 그리고R4 및 R5는 독립적으로 탄소수 1 내지 24의 직쇄 또는 측쇄 알킬, 탄소수 2 내지 24의 직쇄 또는 측쇄 알케닐이다. - 제 1항에 있어서, R4 및 R5가 탄소수 1 내지 24의 직쇄 또는 측쇄 알킬인 일반식(I) 또는 (II)의 화합물.
- 제 1항에 있어서, R4 및 R5가 독립적으로 n-부틸, sec-부틸, t-부틸, n-도데실, n-옥타데실, n-옥틸, 이소옥틸, 올레일, 스테아릴, n-테트라데실, 1-헥사데실, 리놀레일, 리놀레닐, 피틸, 미리실, 라우릴, 미리스틸, 세틸, 베헤닐, 페닐 또는 카테칠인 일반식(I) 또는 (II)의 화합물.
- 제 1항에 있어서, 디-n-도세스-1-일-2-(피리드-2-일)에틸 보레이트, n-옥타데스-1-일-2-(피리드-2-일)에틸 페닐보로네이트, n-옥트-1-일-2-(피리드-2-일)에틸 페닐보로네이트 및 n-올레-1-일-2-(피리드-2-일)에틸 페닐보로네이트로 이루어진 군으로부터 선택된 일반식(I) 또는 (II)의 화합물.
- 하기 성분 a) 및 b)를 포함하는 윤활제 조성물:a) 윤활유 및b) 제 1항에 따른 일반식(I) 또는 (II)을 갖는, 조성물의 총 중량 기준으로 0.05∼15 중량%의 화합물 1 이상.
- 제 5항에 있어서, 윤활유가 합성 유 또는 합성 및 무기유의 혼합물인 윤활제 조성물.
- 제 5항에 있어서, 윤활유가 그리스 또는 기타 고체 윤활제인 윤활제 조성물.
- 제 5항에 있어서, 성분 b)가 조성물 총 중량 기준으로 0.2∼5 중량% 존재하는 윤활제 조성물.
- 제 5항에 있어서, 산화방지제, 금속 탈활성화제, 방청제, 부식 방지제, 점도 지수 향상제, 극압제, 유동점 억제제, 고체 윤활제, 분산제, 세제, 소포제, 색상 안정화제, 고압 첨가제, 해유화제, 내마모 첨가제 및 마찰계수를 감소시키는 첨가제로 이루어진 군으로부터 선택되는 첨가제를 더 포함하는 윤활제 조성물.
- 제 5항에 있어서, 성분 a)가 액체오일이고, 성분 b)가 조성물 총 중량 기준으로 10∼90 중량% 존재하는 첨가 농축액인 윤활제 조성물.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47239003P | 2003-05-21 | 2003-05-21 | |
| US60/472,390 | 2003-05-21 | ||
| PCT/EP2004/050763 WO2004104146A1 (en) | 2003-05-21 | 2004-05-12 | Borate ester lubricant additives |
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| Publication Number | Publication Date |
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| KR20060003119A KR20060003119A (ko) | 2006-01-09 |
| KR101074725B1 true KR101074725B1 (ko) | 2011-10-19 |
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| US (1) | US7291581B2 (ko) |
| EP (1) | EP1625193B1 (ko) |
| JP (1) | JP4838133B2 (ko) |
| KR (1) | KR101074725B1 (ko) |
| CN (1) | CN100350025C (ko) |
| AT (1) | ATE475703T1 (ko) |
| CA (1) | CA2524340C (ko) |
| DE (1) | DE602004028358D1 (ko) |
| MY (1) | MY136312A (ko) |
| SA (1) | SA04250281B1 (ko) |
| TW (1) | TWI357441B (ko) |
| WO (1) | WO2004104146A1 (ko) |
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| US8507417B2 (en) * | 2006-03-07 | 2013-08-13 | Exxonmobil Research And Engineering Company | Organomolybdenum-boron additives |
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| JP5379361B2 (ja) | 2007-08-08 | 2013-12-25 | 出光興産株式会社 | 耐摩耗剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
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| CN104178248A (zh) * | 2013-05-27 | 2014-12-03 | 天津市泽畅科技有限公司 | 一种添加在发动机油中的沉积物控制剂 |
| CN103601748B (zh) * | 2013-10-17 | 2016-11-02 | 上海交通大学 | 羟烷基化杂环硼酸酯及其制备方法、用途 |
| US9309205B2 (en) | 2013-10-28 | 2016-04-12 | Wincom, Inc. | Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures |
| FR3016887B1 (fr) * | 2014-01-27 | 2016-02-05 | Total Marketing Services | Compositions lubrifiantes comprenant des copolymeres thermoassociatifs et echangeables |
| FR3016885B1 (fr) * | 2014-01-27 | 2017-08-18 | Total Marketing Services | Copolymeres thermoassociatifs et echangeables, compositions les comprenant |
| JP2018500443A (ja) * | 2014-12-29 | 2018-01-11 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | 潤滑グリースのための相乗的なさび止め剤の組合せ |
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- 2004-05-12 CN CNB2004800135198A patent/CN100350025C/zh not_active Expired - Fee Related
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| Publication number | Publication date |
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| CA2524340C (en) | 2013-08-20 |
| KR20060003119A (ko) | 2006-01-09 |
| EP1625193B1 (en) | 2010-07-28 |
| CN1791664A (zh) | 2006-06-21 |
| US7291581B2 (en) | 2007-11-06 |
| DE602004028358D1 (de) | 2010-09-09 |
| SA04250281B1 (ar) | 2008-09-02 |
| ATE475703T1 (de) | 2010-08-15 |
| JP4838133B2 (ja) | 2011-12-14 |
| MY136312A (en) | 2008-09-30 |
| CN100350025C (zh) | 2007-11-21 |
| TWI357441B (en) | 2012-02-01 |
| EP1625193A1 (en) | 2006-02-15 |
| WO2004104146A1 (en) | 2004-12-02 |
| JP2007503456A (ja) | 2007-02-22 |
| TW200500456A (en) | 2005-01-01 |
| CA2524340A1 (en) | 2004-12-02 |
| US20040235681A1 (en) | 2004-11-25 |
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