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10/15/12

CN Ch bin du nhn

10/15/12

CN Ch bin du nhn

D ha tan trong du v khng phn ng vi du. Khng hoc t tan trong nc. Khng nh hng n tc dng nh ha ca du.

Khng b phn hy bi nc v kim loi.


Khng gy n mn kim loi. Khng b bc hi nhit lm vic.

Khng lm tng tnh ht m ca du.


Hot tnh c th kim tra c. Khng hoc t c, r tin, d kim.
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1.1 C ch phn ng oxy ha du: c ch gc qua 3 giai on Khi mo: xy ra chm v i hi nng lng

RH + O2

R* + HO2*

Lan truyn: xy ra nhanh, phn ng chui


R* + O2 ROO* or R* + O2 + RH ROO* + RH ROOH + R* HO2* + RH H2O2 + R*
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ROOH + R*

Phn nhnh chui


ROOH RO* + HO* 2ROOH RO* + ROO* + H2O RO* + RH ROH + R* .....

Kt thc:
R* + R* R-R ROO* + R* ROOR ROO* + ROO* R,O + R,,OH + O2

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CN Ch bin du nhn

S c mt ca cc ion kim loi l tc nhn cho qu trnh pht trin mch v khi mo. Giai on khi mo:
M(n+1)+ + RH Mn+ + O2 Mn+ M(n+1)+ + H+ + O2* + R*

Giai on pht trin mch:

M(n+1)+ + ROOH Mn+ + ROOH


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Mn+ + H+ M(n+1)+ OH*

+ ROO* + RO*
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Phn ng to axit t xeton v anhydrit to thnh axit nhit > 120oC


O ROO R C H -ROOH O 2 R C OOH 2 R O C OH + O2 R C O O2 R O RH C OO - R

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1.2 Ph gia chng oxy ha: Cht c ch gc t do Cht phn hy hydroperoxyt

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CN Ch bin du nhn

Cht c ch gc t do:

C ch hot ng: lm chm giai on lan truyn


Thay phn ng:

ROO*
Bng phn ng:

RH

ROOH

+ R*

ROO*
Hp cht phenol

+ InH

ROOH

In*

C hai dng cht c ch c bn:

Hp cht amin thm 10/15/12

CN Ch bin du nhn

C hai dng cht c ch c bn: Hp cht phenol

Hp cht amin thm

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Loi ph gia

Tn ph gia

Cng thc ha hc
CH3 OH CH3 C CH3 CH3
OH H3C CH3 C(CH3)3

2,6 diter butyl paracresol

CH3

C CH3

CH3

Cc dn xut ca phenol 4,6 diankyl phenol

(CH3)3C HO (CH3)3C
OH (CH3)3C CH2 OH

C(CH3)3 CH2 OH C(CH3)3

C(CH3)3

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CH3

CH3

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C ch hot ng ca ph gia chng oxy ha gc phenol


OH k1 O*

RH +

2,6-di-t-butyl-4-methylphenol k2
R* + O2 ROO*

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C ch hot ng ca ph gia chng oxy ha gc phenol


OH + ROO* O*

+ ROOH

O*

O + ROO* *

O Heat OOR

+ RO* + CH3* O

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C ch hot ng ca ph gia chng oxy ha gc phenol


O* O*

OH

+ CH3 CH3

+ CH3 CH2

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Loi ph gia

Tn ph gia

Cng thc ha hc
H R N R

Diankylphenylamin

Diankylphenyl Alphanaptylamin Cc dn xut ca amin thm

H R N R

Phenyl Alphanaptylamin

H N

H3C

CH NH

CH3

Diamin thm
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H3C

HN CH CH3

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Ph gia gc amin Ph gia diphenylamin


+ HNO3
Benzen

NO2 + H2
Nitrobenzen

catalyst

NH2
Anilin

H
Catalyst

NH2
Anilin
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N
Diphenylamin
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Ph gia gc amin Ph gia alkyldiphenylamin


H
C8 C8 olefin C8 C9 olefin

H N
C4 + C8 olefin C4, C8

H N
C4, C8

C9 olefin + Styren

H
C9

H
C9 St, C8

C8, St

H N
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H N
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C ch hot ng ca ph gia chng oxy ha gc amin thm


H R*, RO*, ROO* R N R

N*

+ RH, ROH, ROOH

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C ch hot ng ca ph gia chng oxy ha gc amin thm O*


R N
*

ROO*

N ROO*

R +RO*

OR N + ROO* O* R N ROO O - RO* R O -ROR R

ON +

R OOR

N=O+O

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C ch hot ng ca ph gia chng oxy ha gc amin thm O*


R N R

OR N* + R

OR R N + *

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C ch hot ng ca ph gia chng oxy ha gc amin thm


CHRR O* R N R RRHC* R O N R

H R N R +

R C=O R

120oC

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C ch hot ng ca ph gia chng oxy ha gc amin O* thm H


R N R + R C* R CRR

OH R N + ROO* O* R N R + ROOH R + R C = CR R

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S kt hp gia hai loi ph gia gc phenol v amin thm


OH

N*

O* H

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S kt hp gia hai loi ph gia gc phenol v amin thm


RO*, ROO* ROH, ROOH

H R N R R N* R

O*

OH

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Mechanism of synergism between ADPA and hindered phenol CN Ch bin du nhn

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Ph gia ph hy hydroperoxit ROOH

Hp cht alkylsunfit Hp cht alkylphosphit Dithiophosphate

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Ph gia ph hy peroxit ca alkylsunfit


O CH3 (CH2)x CH CH (CH2)2 C O CH2 (CH2)x S S CH3 CH3

CH3 (CH2)x CH CH (CH2)2 C O CH2 (CH2)x O Sulfurized ester

CH3 (CH2)x CH CH (CH2)x S S

CH3

CH3 (CH2)x CH CH (CH2)x Sulfurized olefin


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CH3

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Ph gia ph hy peroxit ca alkylsunfit

CH2

CH2

Dibenzyl sulfide
OH R (S)x HO Dialkylphenol sulfide
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C ch ph hy peroxit ca alkylsunfit
ROOH R S R -ROH R" R' C S R H2C H O RSOH + H2C = CR'R" ROOH - ROH RH + SO2 ROOH - ROH

RSO2H ROOH - ROH

RSO3H ROSO3H H2O Decompose more hydroperoxides H2SO4 ROOH ROOR R2C=O
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Ph gia ph hy peroxit ca alkylsunfit

O S R S R N R C S R S S R C N R R N C S C C C C O Dithiocarbamate ester R O R C O R

Bis (disubstituted dithiocarbamate

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C ch ph hy peroxit ca alkylphosphite

R"O* P(OR')2 R"OO*

R R"O P(OR')2 + O R"O P(OR')2 + R

O*

O*

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Cht phn hy hydroperoxyt : km dialkyldithiophosphate (ZDDP) Km Dialkyldithiophosphate c iu ch bi Herbert C. Freuner S


4 ROH + P2S5 S 2 RO RO P SH + ZnO RO RO 2 (RO)2PSH S P S
2

H2S

Zn

H2O

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C ch hot ng ca ph gia ph hy hydroperoxyt ca ZDDP


S 4 (RO)2PS
2

S Zn + R,OOH (RO)2PS
2

Zn4O

R,OH

S + (RO)2PS
2

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C ch hot ng ca ph gia ph hy hydroperoxyt ca ZDDP


S (RO)2PS* + R,OOH S (RO)2PSH S (RO)2PS
2

+ R,OO*

S 2 (RO)PSH + R,OOH

R,OH

H2O

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C ch hot ng ca ph gia ph hy hydroperoxyt ca ZDDP


S (RO)PS Zn
2

S + R,OO* R,OO-

+ (RO)2PSZn+ + (RO)2PS*

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C ch hot ng ca ph gia ph hy hydroperoxyt ZDDP


RO RO S P S Zn S S P OR OR

RO2* R-O-O RO RO S* P S Zn S S P OR RO2* RO RO S P S S S P OR RO OR R-O-O RO S: P


*

S P S Zn S

OR OR

OR + 2 RO2+ Zn2+

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Tnh a nng ca ph gia: c ch gc t do v phn hy hydroperoxyt


(CH3)3C HO (CH3)3C
(CH3)3C HO (CH3)3C CH2CH2 - C - O - CH2CH2 - S - CH2CH2 - O - C - CH2CH2 O O

CH2 - S - CH2 - O - C - O - C13H37 O


C(CH3)3 OH C(CH3)3

2,2 thioetylen bis [3-(3,5- di-tert butyl 4 hydroxyphenyl) propionate


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Vai tr:

Hp ph ln cc cn bn v li ko chng ra khi b mt m chng bm dnh, gi chng trng thi l lng trong khi du.
Hp cht: l cc hp cht c kim c cc. Cc kim loi thng dng l Ca, Mg, Na, Ba. C 4 h ph gia ty ra: Sunfonat. Phenolat. Salixylat.
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Photphonat.

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2.1 Sunfonat tng hp:


Phng php iu ch: Sunfo ha alkyl benzen:

SO3H + SO3 or Oleum R


SO3H + NaOH R
SO3Na 2 R
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R
SO3Na +H2O R
SO3 Ca + 2NaCl R
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2

+ CaCl2

Sunfonat trung tnh

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Sunfonat kim cao:


SO3H R M(OH)2 O S R MCl2 SO3Na R O S R
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O O M O S O R

CO2

xMCO3 O O M O S O M = Ca, Mg, Ba R


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Sunfonat ca kim loi Ca hoc Mg v cu trc Mixen ca ph gia ty ra kim cao:

O
++

++

S O O S O

O Ca O
+ +
+

M
+

M
++

M (MCO3)n M M M
++

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2.2 Alkyl phenolate iu ch


OH OH

CH2O OH

Methylene-coupled R = C6 to C12 alkylphenol x=1-3


OH S or SCl2 (S)x R R OH

R Alkyl phenol

Sunfua coupled alkylphenol or phenol sulfide


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Alkyl phenolate kim cao iu ch


OH Y R R OH Base R CO2 Y = S, CH2 M = Ca, Mg x MCO3 O M Y R
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M Y

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2.3 Alkyl salixylat


OH KOH CO2 OH COOK HCl OH COOH + KCl R

Alkylphnol
OH

potassium alkylsalicylate alkylsalicylic acid


OH COOK + CaCl2 COO Ca + 2KCl

R
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R
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Alkyl salixylat kim cao


OH O C O M O O C OH

R CO2

OH

O C

O MCO3 O M O C

OH

R
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M = Ca, Mg
CN Ch bin du nhn

R
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2.4 Ph gia ty ra hn hp Hn hp ca: Phenol sunfurit v salixylat Phenol sunfurit v sunfonat Mi hn hp th hin tnh cht ca cc hp cht ring l.

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2.5 hp cht phosphonate


O R P O O M R S P O O M R O P O S O P R

M O

Metal phosphonate

Metal thiophosphate

Metal thiopyrophosphate

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2.5 hp cht phosphonate


Synthesis of alkenylphosphonic acide
R R R R Phosphorus pentasulfide R R + P 2S5 R R R R R R P2 S5 R R R

Polyisobutylene - P2S5 adduct H2O

S R R R R Polyisobutenylphosphonic acid CN Ch bin du nhn R P OH OH

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2.5 hp cht phosphonate


S R R R R R1 Polyisobutenyl phosphonic acid P OH OH R1 Base R R R

S P R O OH M O

S P OH R R1 or S R R R

R R R R R1 P O O O

Divalent metal salt of Polyisobutenylphosphonic acid (soap)


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Hp cht phosphate kim cao


S R R R R R1 Base S R R R R R1
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S O OH M O P OH R R1 CO2 S P OH R R1
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R R R

x MCO3 O OH M O

R R R

3.1 Chc nng: Ngn nga hoc lm chm qu trnh to cn v lng ng trong iu kin hot ng nhit thp.

Lm yu lc cu kt gia cc tiu phn ring bit vi nhau, to iu kin lm tan r cc kt ta xp v cc khi kt t tng tiu phn c th tn ti nh mt thc th ring.

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3.2 c trng: L cc polyme hu c C cha nhm O hoc N Khng cha kim loi. ph gia khng tro. Tn ti di 3 dng:

ankenyl polyamin suxinimit

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Cu trc chung ca ph gia phn tn

Phn phn cc, N, O, P

Nhm ni

Phn u du: nhm alkyl

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3.3 C ch hot ng

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3.4 Ph gia ankenyl polyamin suxinimit Tng hp ph gia ankenyl polyamin suxinimit Giai on 1: tng hp ankenyl suxinic anhydrit (PIBSA):
O O O Maleic Anhydride Polyisobutylene
10/15/12

O + Heat R or Cl2 O Polyisobutenyl Succinic Anhydride


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3.4 Ph gia ankenyl polyamin suxinimit Giai on 2: trung ha bng 1 polyamide to succinimide
O R O + H2N - (CH2CH2NH)x - NH2 O PIBSA Polyamine R O
N - (CH2CH2NH)x - NH2

+ H2O

Mono succinimide

O 2 PIBSA + Polyamide R NH N O + H2O


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x

O N O R

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3.5 Ph gia ester Succinate: Tng hp ester Succinate:


OH R, O PIB O O + HOH2C R C R, CH2OH O R, O PIB O O R C CH2 + 2H2O CH2 C PIBSA Polyhydric Alcohol R CH2 OH Polyisobutenylsuccinate Ester CH2

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3.5 Ph gia ester Succinate: Este succinate: C ch hot ng: nh succinimide u nhc im: Km bn nhit so vi succinimide Kh nng phn tn km hn succinimide c s dng hn hp vi succinimide

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3.6 Ph gia ankenyl polyamin phenol: Tng hp ph gia ankenyl polyamin phenol:
OH OH

+ Polyisobutylene (PIB)

Acid

PIB Polyisobutylphenol

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3.6 Ph gia ankenyl polyamin phenol:


OH + CH2O + PIB H2N H N NH2

NH2 OH CH2 N H PIB NH

NH2 NH CH2 N H PIB OH CH2 N H NH

NH2

OH CH2 N H

H N

OH N H CH2

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PIB

CN Ch bin du nhn PIB

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3.7 Ph gia ester phosphate: Tng hp ph gia ester phosphate:


Polyisobutylene + P2O5 Adduct

H2O

S Polyisobutenyl P OH OH or Polyisobutenyl

S P OH OH

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3.7 Ph gia ester phosphate: Tng hp ph gia ester phosphate:


S S PIB P OH Polyisobutenylthio phosphonic Acid OH + O CH3 Propylene Oxide Bis - hydroxypropyl Polyisobutenylthiophosphonate PIB P CH3 OCH2CH OH OH

OCH2CH

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3.8 Ph gia polyethylene:


CH3 ( CH2 CH2 )m CH CH2 n + N 4 - Vinylpyridine Radical Initiator CH3 CH2 CH2 m C CH2

Ethylene Propylene Copolymer

CH3 CH CH2 n-1

N
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3.8 Ph gia polyacrylate:


CH3 n H 2C = C COOR + CH3 CH2 = C C O OCH2CH2N CH3 CH3

Alkyl Methacrylate

Dimethylaminoethyl Radical Initiator Methacrylate

CH3 CH2 C CH2

CH3 C CH2

COOR C CH3 CH3 x

COOR n-x O C OCH2CH2N

CH3

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3.8 Ph gia copolyme styren anhydrit maleic:


CH CH2 O CH C O CH C O n + ROH + H2N N R R

Styrene maleic anhydride polymer

CH

CH2 O

CH C NH

CH C OR O n

N R
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R
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Ti sao phi dng ph gia chng ng?

Thnh phn ca du khong:


Aromat: 5-10% Naphten: 20-30% Parafin: 60-70% Parafin

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4.1 Chc nng ca ph gia chng ng PPD


Gii hn s tng kch thc Ngn cn s kt t ca cc tinh th

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4.2 Cc polyme c chc nng lm gim nhit ng c


CH3 CH2 CH
*

CH2 CH C O
n

CH2 C C O O R n

R
n

R n

Polyalkylnaphtalene Polystyrene alkyl (R = C14, .... , C24)

Polyacrylate

Polymethacrylate alkyl

CH O C O CH3
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CH2 O
n

CH CH C C O O R
m

CH

CH2 O R
n

CH CH C C O O R
m

R O

R O

Copolymer acrylate vinyl fumarate alkyl

Copolymer styrene maleic alkyl


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4.2 Cc polyme c chc nng lm gim nhit ng c


OH

Alkyl phenol mch di

O C O

R R R

Este ca dialkylary ca axit phtalic


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C O

O R
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4.3 nh hng ca PPD n kh nng hot ng nhit thp ca du PPD khng lm thay i im vn c ca du

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5.1 c tnh:
L cc polyme (c trng lng phn t ln v mch di) tan c trong du c tc dng lm gim s thay i nht ca du theo nhit .

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nhit thp cc polyme co cm li khng lm nh hng n nht.

nhit cao, cc polyme dui ra lm tng nht ca du so vi cng nhit .


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5.2 Cc loi ph gia ci thin ch s nht Polyme hydrocacbon


CH2 CH2
n

CH2

CH CH3
m

Copolyme etylen-protylen

CH3 CH2 C CH3


n

Polyisobutylen

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5.2 Cc loi ph gia ci thin ch s nht Polyme este


CH CH2 CH C OR
n

CH O C OR
m

CH3

C C OR

CH2 O

CH3 C C OR CH2 O CH2 CH2 CH2 CH CH3

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5.2 Cc loi ph gia ci thin ch s nht

CH3 C C OR CH2 O
n

CH C OR O

CH C OR O
m

CH3 C C OR CH2 O
n

CH O C N R

CH C O
m

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6.1 Vai tr ca ph gia chng to bt

Chng li tc dng ph ca ph gia ty ra


Duy tr nht ca mng du: qu nhiu bt kh lm gim kh nng bi trn Trnh mi mn do hin tng kh xm thc: ci thin s tch khng kh Trnh s st p sut du khi bm Trnh mt mt du do s trn
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6.2 C ch ph bt ca ph gia

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6.2 C ch ph bt ca ph gia

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6.2 C ch ph bt ca ph gia

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6.2 C ch ph bt ca ph gia

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6.3 c trng ca ph gia: Ha tan t trong du: hp cht c cc ha tan phn tn trong du: c nhnh di

C sc cng b mt nh hn so vi du
6.4 Cc hp cht ph bin: polymetylsiloxan
CH3 H3 C Si CH3
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R1 O Si R2 O
n

CH3 Si CH3
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CH3

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7.1 Vai tr ca ph gia th ng ha kim loi: Hp ph ln b mt kim loi to thnh mt mng bo v, ngn cn hot tnh xc tc.

Hnh thnh phc cht ( phc Chelat) ngn cn s tip xc


trc tip gia b mt kim loi vi du bi trn.

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7.2 Cc loi ph gia th ng ha kim loi


OH CH N CH2 CH3

N N N
HO N CH2 CH2 N CH

N - salixilidenetylamin OH CH

H benzotriazole

N, N - disalixilidenetylamin

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7.3 C ch hot ng ca ph gia th ng ha kim loi

Function of benzotriazole as film forming agent

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7.3 C ch hot ng ca ph gia th ng ha kim loi Function of N,N-disalicylidene-propylenediamine as chelating agent

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8.1 Vai tr ca ph gia c ch g: Ngn cn s tip xc ca nc vi b mt kim loi (hp ph trn b mt kim loi v tc dng nh mng ngn chng m)

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8.2 Cc loi ph gia c ch g:

H19C9

C9H19

Ca2+

OO Zinc naphthenates

Zn2+
2

SO3-

dinonylnaphthenesulfonates

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8.2 Cc loi ph gia c ch g:


O
H3C O O 4-Nonylphenoxyacetic OH

CH CH2

C C O

OH OH

Alkylated succinic acids

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9.1 Vai tr ca ph gia c ch n mn: Cc ph gia ny hp ph ln b mt kim loi to thnh mt mng bo v. Mng bo v ny s dnh cht ln b mt kim

loi trnh b trc ra bi cht phn tn hoc ty ra

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9.2 Cc loi ph gia c ch n mn:

CH3 S S P S H3C C CH2 Pinene photphosunfua R S S P R S

Limonene sunfua

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9.3 C ch hot ng ca ph gia c ch n mn:

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10.1 Vai tr ca cc ph gia tribologie: Gim mi mn cc chi tit c kh do tip xc: ko di thi gian lm vic ca thit b Gim ma st: tit kim nng lng, nhin liu Bin tnh ma st: ti u ha hot ng ca thit b (khi

thay i vn tc trong hp, phanh du)

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10.1 Vai tr ca cc ph gia tribologie:

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10.2 Cc ph gia tribologie: Ph gia chng mi mn (Antiwear Additives) Ph gia cc p (Extreme Pressure Additives) Ph gia bin tnh ma st (Friction Modifiers Additives)

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94

10.3 Cc loi ph gia chng mi mn v cc p


Ph gia ZDDP Ph gia alkyl sunfua

Ph gia phosphat
O O P O O

Triphenylphosphorothionate (TPPT)
10/15/12 CN Ch bin du nhn 95

10.4 C ch hot ng ca ph gia cc p

10/15/12

CN Ch bin du nhn

96

10.5 Ph gia bin tnh ma st: C ch hot ng ca ph gia cc p: xem gia hai b mt mt vt liu rn.

molybdenum disulfide

graphite

fluorinated graphite

10/15/12

CN Ch bin du nhn

97

10.5 Ph gia bin tnh ma st: C ch hot ng ca ph gia cc p: Cho HPVL hoc HPHH bng cc hp cht c cc: Ru mch di

Amine, amide bo
Ester bo

Acide bo

10/15/12

CN Ch bin du nhn

98

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