Vol.4Vol.4

1.

2.

2.1

2.2

2.3

3.

4.

2

3

3

8

16

21

21

2 3

1.

1)

Rp

Rp Rp,max

ktkp

- Rp- Rp,max

2.

A Bis-GMA/

TEGDMA TEGDMA

Rp 2)Bis-GMA TEGDMA

Rp DMPA

1,3-7) (1) (2 3)

(4) (5) (6)

1Rp-- Rp,max

Rp s-

1

Rp,max

O

OO O

O

R

O

OO N

H

R

O

O

ONH

OR

O

A-OCO-R, 1

N-(R-NCO-A, 2)

A-OCN-R, 3

A--OCO, 4

O

OO

O

O

4 5

A-OCN-R (3)A--OCO

(4) A- (6) EGDA (8) HDDA (9)

8,7)

9)

EGDA (8) HDDA (9) A-OCO-R (1,

R = CH(CH3)2) Rp EGDA (8) HDDA (9) Rp

15%A-OCO- (4)

A--OCO (4)

10)

Rp OCH2CH2O 11)Ph-NCO-A (10) --Ph-NCO-A--Me (11) A--Me-NCO-Ph (12)

,-Ph-NCO-A-,-Me2 (13),-Ph-NCO-A-,-Me2 (15)

Rp,max ,-Ph-NCO- A-,-Me2 (14) Rp Ph-NCO-A (10) 20% Rp,max 1/4 CH2

Ph-NCO-A (10)

R-NCO-A (2) A-OCN-R (3)

Rp,max RA (7, R = C4H91.0 < RA (7, R = C6H5, 1.87 < A-OCO-R (1, R = C2H5, 2.17 < A--OCO (4, 12.4 < A- (6, 13.6

12)

Rp Rp CH2=CHCOO- 1 2

A-NCO-R (2)

=RC6F5

C6H4OCH3-p Rp kp kt 13)

b)% % csRp,maxa) (s-1)

1

A-OCO-R1, R = CH(CH3)2

A-OCN-R3, R = CH(CH3)2

A--OCO4

A-6

EGDA8

HDDA9

2

7

40

6

1

3

5

2

4

3

10

18

-

90

15

96

100

100

-

-

360

-

50

250

a) DMPA (0.5 wt%), UV (500 mW/cm2) (25 m)

b)

c) Persoz

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

N-Ph-NCO-A, 10

N--Ph-NCO-A--Me, 11)

N--Ph-NCO-A--Me, 12

N-,-Ph-NCO-A-,-Me2, 13

N-,-Ph-NCO-A-,-Me2, 14)

N-,-Ph-NCO-A-,-Me2, 15)

R = H F OCH3 F

FF

FF

F OCH3

F H3CO

O

ONH

O

O

O

O

O

A-OCN-CC, 5

O

ON O

O

A- , 6

O

OR

RA, 7

O

OO

O

EDGA, 8

HDDA, 9

O

OO

O

6 7

14)A-OCN-R (3, R = C6H5)

Rp

5 wt% 1,4-

DMPA15)

A-OCO-R (1)R-NCO-A (2) A--OCO (4)

RA (7, R = C6H13) RA (7) Rp , R = CH2CH2OH < R = CH2CH2CH2CH2OH < R = CH2CH2CO2H

RA7, R = C6H13

15)

NH

Rp Rp Rp Rp

16) 13, 17)

A-OCO-R (1R = C2H5) R-NCO-A (2R = C4H9) HDDA

(9) RA (7, R = CH(C6H5)C(O)OCH3)

Tg - HDDA (9)

8)

(50/50 wt/wt) Rp,max (s-1) A- (6) > R-NCO-A (2, R = CH(CH3)2) >> RA (7, R = CH2CH2OCH(CH3)2 > A-OCO-R (1, R = CH(CH3)2) > RA (7, R = CH2CH2C(O)OCH(CH3)2)

Rp,max (6) = 1.4Rp,max (2, R = CH(CH3)2) = 7.3Rp,max (7, R = CH2CH2OCH(CH3)2) = 11.0Rp,max (1, R = CH(CH3)2) = 14.6Rp,max7, R = CH2CH2C(O)OCH(CH3)2) 7)

UV Rp (s-1) UV UV

2a)

A-OCO-R (1, R = C2H5)

A-OCN-R (3, R = C6H5)

A--OCO (4)

RA (7, R = C6H13)

HDDA (9)

HDDA (9)

0.34 0.03

0.36 0.08

0.35 0.05

0.35 0.01

0.10 0.02

0.40 0.03

0.09 0.02

0.38 0.03

0.16 0.02

0.007 0.002

0.05 0.02

0.08 0.02

0.25 0.03

0.40 0.03

0.35 0.03

0.03 0.01

0.07 0.02

0.15 0.03

a) [DMPA] = 0.1 wt% = 5 mW/cm2

Rpb) Rp

3 Rp a)

RA (7, R = C6H13)

A-OCO-R (1, R = C2H5)

A--OCO (4)

R-NCO-A (2, R = C6H5)

R-NCO-A (2, R = CH2C6H5)

R-NCO-A (2, R = C4H9)

RA (7, R = CH2C6H5)

RA (7, R = CH2CH2OH)

RA (7, R = CH2CH2OCH3)

RA (7, R = CH2CH2CH2CH2OH)

RA (7, R = CH2CH2CO2H)

1.0

9.8 0.2

12.7 0.3

56.4 5.2

19.6 0.3

16.9 0.3

4.0 0.1

10.3 0.6

2.2 0.2

5.5 0.1

16.9 0.3

1.0

2.5 0.2

5.2 0.5

3.0 0.2

3.0 0.3

2.7 0.2

1.6 0.2

2.8 0.2

2.2 0.2

2.0 0.1

3.0 0.2

a) [DMPA] = 0.5 wt%, = 10 mW/cm2

b) 5 wt%

4

3.9-4.7

3.4-4.4

5.0-6.2

2.2-3.3

4.7-5.7

2.6-3.3

2.9-3.3

1.6-2.0

1.8-2.4

2.3-5.7

4.9-5.5

8 9

Bis-GMA A-OCO-R (1, R = C6H5Rp,max = 0.017 0.003 s-1) A- (16Rp,max = 0.030 0.001 s-1) Bis-GMA/TEGDMA (70/30 wt/wt) Rp,max = 0.0009 0.0004 s-1 18)

A-OCN- (17)

19)

NaCl 20 2 NaCl

IR NH CHC=O C=C

0.1 wt% DMPA

Rp 20 0.9

IR

20, 21)

R-NCO-A (2) A-OCN-R (3)

Rp R1 R2 9)

9) 22) Rp > > >- >

Rp 23)

O

OO

O

N

O

A- , 16

O

ONH

O

O

O

O

O

ONH

O

OO

O

(A-OCN- , 17)

O

OR2

R1

OOH O

O O

O

O

O

O

OR2 =

R1 = C2H5, C3H7, (CH3)2CH, C4H9, (CH3)3C, C6H5CH2

- (OCO)

O

O

NH

N- (NCO)

NH

O

O

(OCN)

NH

O

NH

(NCN)

1.0

0.8

0.6

0.4

0.2

0

0 10 20 30 40

(a)

(b)

(c)(d)

(e)

(f)

(g)

2Rp: -NCO-MA (18, a) MA-OCO- (19, b)RMA (32, R = (CH2)3OH, c)RMA (32, R = CH2C(O)CH2C(O)CH3, d)

HDDMA (33, e)RMA (32, R = C3H7, f )RMA (32, R = C4H9, g ) ( [DMPA] = 0.1 wt%,

= 5 mW/cm2, 25

10 11

R2 0.60 R1 = C2H5

< < < - OCO > OCN R1 = NCO > OCN > OCOTm

9)

3MA--OCO (24) RMA (32)

0

0.8

0.6

0.4

0.2

050 100 150 200

MA--OCO (24)

RMA (32, R = n -t - )

O

OO N

H

O

O

OO O

O

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

O

OO N

H

O

O O

O

O

O

OCD2 CD2

CD O

O

O

O

N--NCO-MA, 18

MA-OCO- , 19

N-n-n--NCO-MA, 20

N--NCO-MA, 21

N-n-n--NCO-MA, 22

N-t-t--NCO-MA, 23

MA--OCO, 24

-d5(MA--OCO-d5, 25

N--NCO-MA, 26

MA-OCO- , 27

O

OO O

O

O

OO N

H

O

RMA, 32

HDDMA, 33

O

OO

O

OR

O

MA-NCN- , 30

MA-OCN- , 31

O

ONH

NH

O

O

ONH

O

O

t-MA-OCN-t- , 28

MA-OCN- , 29

O

ONH

O

O

O

ONH

O

O

Tm ()R1 R25Rp,max Tm

-NCO-MA (18)

MA-OCO- (19)

MA-OCN- (31)

-NCO- MA (26)

MA-OCO- (27)

MA-OCN- (29)

MA-NCN- (30)

RMA (32, R = C4H9)

-

NCO

OCO

OCN

NCO

OCO

OCN

NCN

-

Rp,maxa) (s-1)

0.012 (25)

0.0114 (25)

0.009 (50)

0.045 (25)

0.009 (25)

0.028 (25)

0.082 (75)

0.0006 (25)

28

< 25

43

59

< 25

< 25

70

< 25

a) [DMPA] = 0.1 wt %, = 5 mW/cm2

12 13

R1R2Rp2567-NCO-MA (26) -NCO-MA (18, 20-23) -NCO-MA (26) 25

6725

67-NCO-MA (26

Rp,max (67) = 0.045 s-1)MA-NCN- (30, Rp,max (75) = 0.082 s-1MA-NCN- (30)(75)

-NCO-MA (26) (60)

9)

R1Rp > > > > - >> >

MA-NCO-R1Rp (26) > t - (23) > (21) > n- (22) > (18), n- (20) > > Rp,max0.60-NCO-MA (26)

9)

MA--OCO (24)

5%RMA (31, R = C6H13)

15)MA--OCO (24)

Rp

2567

NHIRNH

Rp9)

24)RA (7, R = CH2CH2OH)

25Rp,max802.5OHRp,maxRA (7, R = CH2CH2OH) 2540%80%

22)

(NHC(O)O)

(OC(O)O)MA

OCO (24)Rp22)

-NCO-MA (18)255067Rp()259)-25, 5 mW/cm2, 0.1

wt% DMPARpMA--OCO (24) > t --NCO-MA (23) > n --NCO-MA (22) > -NCO-MA (18) > n--NCO-MA (20)MA--OCO (24< t --NCO-MA23< n -NCO-MA (20) -NCO-MA (18) < MA-NCO-n- (22)

22)

403020100

1.0

0.8

0.6

0.4

0.2

0

(a)

(b)

(c)

(d)

4MA--OCO (24) a5%b

RMA (32, R = C6H13cd-

[DMPA] = 0.5 wt% = 10 mW/cm225

5RA (7, R = CH2CH2OH)Rp,max[DMPA] = 1 wt%

0.06

0.04

0.02

0

0.08

20 30 40 50 60 70 80 90

Rp,

max (s-

1)

14 15

CH2=C(CH3)COO O

(NCO) NH (OCN)

Tm -NCO-MA (18) 28MA-OCN- (23) 43-NCO-MA (26) 59MA-OCN- (29)

< 25 Tm

-NCN-MA (30)Tm = 70-NCO-MA (26) Tm = 59

9)

11)MA--OCO (24) MA--OCO-d5 (25) Rp 50 80 0.77MA--OCO (24) 0.73MA

OCO-d5 (25) 25) CH2-

Rp MA- -OCO

(24) MA--OCO-d5 (25)

DMPA

C6H5C(O)

R1 -NCO-MA (21) t --NCO-MA (23) t -

RMA (23, R = ) HDDMA (33, 50 wt%)

MA-NCN- (30) MA-OCN- (29) MA-OCN-t - (28) MA-OCN- (29) > MA-OCN-t - (28) > MA-NCN- (30) 22)MA-OCN-t - (28) MA-NCN- (30) -

Bis-GMA/MA- (34) (70/30 wt/wt, 70 wt% 4 m

) 18)Bis-GMA/TEGDMA Rp 0.013 0.004 s-1 0.50 0.03 Bis-GMA/MA- (34) Rp 0.040 0.002 s-1 0.63 0.03 Bis-GMA/MA-OCO- (35) Rp 0.020 0.004 s-1 0.55 0.01 Bis-GMA/ MA- (34)

Bis-GMA/TEGDMA MA-OCO-35

70 wt% 4 m Bis-GMA/

MA (34) (70/30 wt/wt) Tg 140 3 56 5 ) Bis- GMA/TEGDMA (70/30 wt/wt) 144 8 100 6)

Bis-GMA/MA-OCO- (35) (70/30 wt/wt) Tg (116 1 65 8) Tg - Tg Bis-GMA/MA- (34)

Tg 26)

6MA--OCO (24) -

[DMPA] = 0.1 wt%, = 5 mW/cm2

67

25

15

1.0

0.8

0.6

0.4

0.2

02010 300

NH

N

N

O

H

N

N

O

H

H H

N

N

O

H

H

O

NH

O

N

O

H

O

N

O

HO

N

O

H

H N

O

O

7: () ()

16 17

RMA (32, R = C3H7) -NCO-MA (18) Rp,max 12 7 2

-NCO-MA (36) RMA (32, R = C3H7) 84

MA-OCN-CC (37)

Tm 67 MA-OCN-CC (37) > MA-OCN- (38) > MA-OCO- (35) > MA

OCO (24)MA-OCN- (29) > HDDMA (33) 22)MA-OCN-CC (37)

0.8 HDDMA (33) 0.6 MA--OCO (24) 0.75

MA-OCN-CC (37) Rp 25 6725> 0.967 0.6522)MA-OCN-CC (37) 67

HDDMA (33)

67 25 25 0.66 67 0.75

Rp 524) MA--OCO (24)

MA-OCN-CC (37) (25)

22) 0.45

(25)

kt/kp[M] 25

25 67

22)

MA-OCN-CC (37) MA-OCN- (38)

Tg MA-OCN-CC (37) MA-OCN- (38)

MA-OCN-CC (37)

50/50 wt/wtMA-OCN-t - (28) MA-NCN- (30) MA-OCN-t - (28)MA-NCN- (30) > MA-OCN-CC (37) > -OCN-MA (29) MA-OCN-CC (37) MA-OCN-t - (28) 5 22).

MA-OCN- (39)

Bis-GMA Rp 37UV (365 nm) Rp 10 MA-OCN- (39) Bis-GMA

O

ONH

O

O

O

OO

O

O

O

OO

O

N

O

O

ONH

O

O

O

O O

O

OO

O

NH

MA- , 34

MA-OCO- , 35

N--NCO-MA, 36

MA-OCN-CC, 37

MA-OCN- , 38

0 50 100 150 200 250

1.0

0.8

0.6

0.4

0.2

0

MA-OCN-CC (37), 25

HDDMA (33), 67

MA-OCN-CC (37), 67

HDDMA (33), 25

8MA-OCN-CC (37)HDDMA (33)2567-

[DMPA] = 0.1 wt% = 5 mW/cm2

18 19

TEGDMA

11 4.4% Bis-GMA/TEGDMA (70/30 wt/wt)

6.4% Bis-GMA/TEGD

MA-OCN- (39) Bis-GMA TEGDMA

18)

10Bis-GMA

-

ONH

ON

O

O

O

(MA-OCN- , 39)

9Bis-GMA37

-([DMPA] = 0.1 wt% = 5.0 mW/cm2

1.0

0.8

0.6

0.4

0.2

0

0 50 100 150 200 250 300

Bis-GMA/MA-OCN- (39)(70/30 wt/wt)

Bis-GMA/MA-OCO- (34)(70/30 wt/wt)

Bis-GMA/TEGDMA (70/30 wt/wt)

0.8

0.6

0.4

0.2

0

0 5 10 15 20

Bis-GMA/MA-OCN- (39) (70/30 wt/wt)

Bis-GMA/ MA-OCO- (35)(70/30 wt/wt)

Bis-GMA/TEGDMA (70/30 wt/wt)

11Bis-GMA25

70/30 wt/wt([DMPA] = 0.1 wt% = 0.1 mW/cm2

%

6.4

4.8

3.2

1.6

0

2 4 6 8 10 120

Bis-GMA/TEGDMA (70/30 wt/wt)

Bis-GMA/MA-OCN- (39)(70/30 wt/wt)

Bis-GMA/MA-OCO- (35)(70/30 wt/wt)

20 21

18)

Bis-GMA/MA-OCN- (39)

Bis-GMA/TEGDMA

Bis-GMA/MA-OCN- (39) Bis-GMA

DEGDMA

DMA (Dynamic mechanical analysis)

-50-150

18)

3.

-

Rp

11)

12, 16)

17, 13)

MA-OCN-CC (37) DMPA CH3SO3H, 400

ppmRp 27) 28) Rp

Rp

4.

Rp

Rp

a,b)

%

%%

c)

MPaTg

Rp,max (s-1)

6Bis-GMA (70/30 wt/wt)

a) [Bis-GMA] = 51.8-56.6 mol%

b) (MA) (A)

c) ISO/DIS40493

TEGDMA

A-OCO-R (1, R = C6H5)

MA-OCO- (35)

MA-OCN- (39)

A- (16)

0.645 0.009

0.813 0.002

0.720 0.006

0.858 0.005

0.929 0.007

0.009 0.0004

0.0017 0.003

0.011 0.002

0.032 0.002

0.030 0.001

6.02 0.15

5.47 0.20

4.01 0.27

4.22 0.47

5.21 0.36

105.1 2.8

89.5 0.7

97.3 3.1

121.0 0.6

106.5 0.8

92.6 0.08

95.8 3.0

88.1 5.0

79.9 4.0

80.3 6.6

7.2 2.0

7.7 0.2

8.5 0.3

6.9 1.3

6.2 1.9

a) DMA DMA

7Bis-GMA (70/30 wt/wt)DMA

a) (MA) (A)

TEGDMA

A-OCO-R (1, R = C6H5)

MA-OCO- (35)

MA-OCN- (39)

A- (16)

0.622

0.768

0.694

0.815

0.910

0.648

0.801

0.739

0.840

0.918

0.815

0.883

0.921

0.913

0.944

)Decker C, Elzaouk B, Decker D: Kinetic study of ultrafast photopolymerization reactions. J. Macromol. Sci.-Pure Appl. Chem., A33: 173-190, 1996.

)Lovell LG, Stansbury JW, Syrpes DC, Bowman CN: Effects of composition and reactivity on the reaction kinetics of dimethacrylate/dimethacrylate copolymerizations. Macromolecules, 32: 3913-3921, 1999.

)Decker C, Moussa K: A new class of highly reactive acrylic monomers, 1. Light-induced polymerization. Makromol. Rapid Commun., 11: 159-167, 1990.

)Decker C, Moussa K: A new class of highly reactive acrylic monomers, 2. Light-induced copolymerization with difunctional oligomers. Makromol. Chem., 192: 507-522, 1991.

)Moussa K, Decker C: Light-induced polymerization of new highly reactive acrylic monomers. J. Polym. Sci., Part A: Polym. Chem., 31: 2197-2203, 1993.

)Decker C, Moussa K: Photopolymerisation de monomeres multifonctionnels-IV. Acrylates a structure carbamate ou oxazolidone. Eur. Polym. J., 27: 403-411, 1991.

)Decker C, Moussa K: Photopolymerisation de monomeres multifonctionnels-V. Resines polyurethannes-acrylates. Eur. Polym. J., 27: 881-889, 1991.

)Kilambi H, Reddy SK, Schneidewind L, Lee TY, Stansbury JW, Bowman CN: Design, development, and evaluation of monovinyl acrylates characterized by secondary functionalities as reactive diluents to diacrylates. Macromolecules, 40: 6112-6118, 2007.

)Berchtold KA, Nie J, Stansbury JW, Hacioglu B, Beckel ER, Bowman CN: Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization: steady-state evaluation. Macromolecules, 37: 3165-3179, 2004.

10)D'Alerio GF, Huemmer T: Preparation and polymerization of some vinyl monomers containing the 2-oxo-1,3-dioxolane group. J. Polym. Sci., Part A: Polym. Chem., 5: 307-321, 1967.

11)Beckel ER, Stansbury JW, Bowman CN: Effect of aliphatic spacer substitution on the reactivity of phenyl carbamate acrylate monomers. Macromolecules, 38: 3093-098, 2005.

12)Jansen JFGA, Dias AA, Dorschu M, Coussens B: Fast monomers: Factors affecting the inherent reactivity of acrylate monomers in photoinitiated acrylate polymerization. Macromolecules, 36: 3861-3873, 2003.

13)Beckel ER, Nie J, Stansbury JW, Bowman CN: Effect of aryl substituents on the reactivity of phenyl carbamate acrylate monomers. Macromolecules, 37: 4062-4069, 2004.

14)Kilambi H, Reddy SK, Schneidewind L, Stansbury JW, Bowman CN: Copolymerization and dark polymerization studies for photopolymerization of novel acrylic monomers. Polymer, 48: 2014-2021, 2007.

15)Kilambi H, Stansbury JW, Bowman CN: Deconvoluting the impact of intermolecular and intramolecular interactions on the polymerization kinetics of ultrarapid mono(meth)acrylates. Macromolecules, 40: 47-54, 2007.

16)Jansen JFGA, Dias AA, Dorschu M, Coussens B: Effect of dipole moment on the maximum rate of photoinitiated acrylate polymerizations. Macromolecules, 35: 7529-7531, 2002.

17)Kilambi H, Beckel ER, Berchtod KA, Stanbury JW, Bowman CN: Influence of molecular dipole on monoacrylate monomer reactivity. Polymer, 46: 4735-4742, 2005.

18)Lu H, Stansbury JW, Nie J, Berchtold KA, Bowman CN: Development of highly reactive mono-(meth)acrylates as reactive diluents for dimethacrylate-based dental resin systems. Biomaterials, 26: 1329-1336, 2005.

19)Berchtold KA, Hacioglu B, Nie J, Cramer NB, Stanbury JW, Bowman CN: Rapid solid-state photopolymerization of cyclic acetal-containing acrylates. Macromolecules, 42: 2433-2437, 2009.

20)Matsumoto A, Yokoi K: Control of molecular weight of the polymers produced during the crystalline-state photopolymerization of diethyl cis,cis-muconate as studied by gel permeation chromatography and scanning electron micrography. J. Polym. Sci., Part A-1: Polym. Chem., 36: 3147-3155, 1998.

21)Matsumoto A, Odani T: Topochemical polymerization of diene monomers in the crystalline state to control the stereochemistry of the polymers. In Controlled/living radical polymerization: Progress in ATRP, NMP, and RAFT, K. Matyjaszewski ed. ACS Symposium Series 768, American Chemical Society, Washington D. C., pp. 93-106.

22)Berchtold KA, Nie J, Stansbury JW, Bowman CN: Reactivity of monovinyl (meth)acrylates containing cyclic carbonates. Macromolecules, 41: 9035-9043, 2008.

23)Bowman CN, Berchtold KA: (Meth)acrylic acid and (meth)acrylamide monomers comprising cyclic acetal/thioacetal groups, polymerizable compositions, and polymers obtained. US Pat. Appl. 2004/0249098 A1.

24)Lee TY, Roper TM, Jonsson ES, Guymon CA, Hoyle CE: Influence of hydrogen bonding on photopolymerization rate of hydroxyalkyl acrylates. Macromolecules, 37: 3659-3665, 2004.

25)Bowman CN, Stansbury JW, Berchtold KA, Nie J: (Meth)arcrylic and (meth)acrylamide monomers, polymerizable compositions, and polymers obtained. US Pat. 7,498,3942009.

26)Kilambi H, Cramer NB, Schneidewind LH, Shah P, Stanbury JW, Bowman CN: Evaluation of highly reactive mono-methacrylates as reactive diluents for BisGMA-based dental composites. Dent. Mater., 25: 33-38, 2009.

27)Beckel ER, Stansbury JW, Bowman CN: Evaluation of a potential ionic contribution to the polymerization of highly reactive (meth)acrylate monomers. Macromolecules, 38: 9474-9481, 2005.

28)Kilambi H, Konopka D, Stansbury JW, Bowman CN: Factors affecting the sensitivity to acid inhibition in novel acrylates characterized by secondary functionalities. J. Polym. Sci., Part A: Polym. Chem., 45: 1287-1295, 2007.

.Yamada B, Zetterlund PB, "General chemistry of radical polymerization". In: Handbook of radical polymerization, Matyjaszewski K, Davis TP, eds, Wiley-Interscience, New York, pp. 117-186, 2003.

.Zetterlund PB, Yamazoe H, Yamada B, Hill DJT, Pomery PJ, Macromolecules, 34: 7686-7691, 2001.

.Yamada B, Azukizawa M, Yamazoe H, Hill DJT, Pomery PJ, Polymer, 41: 5611-5618, 2000.

.Yamada B, Kageoka M, Otsu T, Macromolecules, 25: 4828-4831, 1992.

.Yamada B, Kageoka M, Otsu T, Macromolecules, 24: 5234-5236, 1991.

.Yamada B, Yoshikawa E, Shiraishi K, Miura H, Otsu T, Polymer, 32: 1892-1896, 1991.

404

4

134

144

163

167176 ()

193

221

ESR

2010722

Vol.1 200910

Vol.2 220102

Vol.3 20103

Vol.4 220107